<![CDATA[annie riley's newsletter ✨: Podcast]]>https://annieriley.substack.com/s/best-manager-ever-podcasthttps://substackcdn.com/image/fetch/$s_!iveX!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fee494f57-30a8-40eb-9494-5b40d4159520_1000x1000.pngannie riley's newsletter ✨: Podcasthttps://annieriley.substack.com/s/best-manager-ever-podcastSubstackSun, 12 Jul 2026 09:57:37 GMT<![CDATA[Best Manager Ever: Jared Erondu]]>https://annieriley.substack.com/p/best-manager-ever-jared-eronduhttps://annieriley.substack.com/p/best-manager-ever-jared-eronduWed, 10 Dec 2025 12:48:04 GMTJared Erondu is a seasoned design and startup leader, and is currently the Head of Design at early-stage startup Span. Jared spent eight years at Lattice, where he went from a solo designer pulling all-nighters in the early days to leading a 50-person design organization, with stints as GM and Head of Marketing as the company scaled. Earlier in his career, he was a design leader at Teespring and Omada Health.

Jared is known for his design mentorship and community-building, and is an active advisor and angel investor.

Listen Now

In this episode, you’ll learn:

  • How to build a selective “sh*t umbrella” over your team

  • The right way to communicate destabilizing intel

  • How to recondition your mindset for “hard mode” leadership

  • How to build a bench of resources to support yourself

  • The best way to recruit exceptional talent

  • Why managing your own mindset is the ultimate leadership unlock

Direct reports praise Jared for:

  • Bringing steadiness to chaos and challenges

  • Setting (and holding!) and exceptionally high bar

  • Thoughtful, astute observations about people and team dynamics

  • Great at coaching and championing the team

  • Long-term relationship building

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Build a “sh*t umbrella” over your team, and then poke holes in it - Cover your team with a “shit umbrella” to protect them and help them focus. But then poke specific holes in the umbrella to decide what you’ll allow through. Allow information that will help them with clarity and stability, and protect them from details that will be destabilizing.

  • Explain WHY as you make changes - Make the changes required to lead— even when it’s hard. But always explain why the change is happening, so your team understands the goals and rationale. In the absence of clear context from you, direct reports will make up stories (it’s human nature!)— which may or may not be accurate.

  • Know when and how to shift into leadership “hard mode” - When you face turbulent moments, shift your leadership mindset. Invest in your well-being to manage your energy. Change your operating cadence to meet the needs of the moment. Don’t expect the normal ways of working to get it done during abnormal moments.

  • Bespoke communication stands out - Jared is thoughtful and deliberate about bespoke communication, both in recruiting and when sharing information with his team. In the age of AI slop, tailored communication stands out. To replicate his success, take a moment to pause. Ask yourself what you need to share, with whom, and at what time.

  • Your bar is the lowest quality work product that goes out the door - The gravitational pull will always be towards atrophy so when you’re trying to push great products, you need to fight against that negative force. Can you delay that as long as possible, by holding up the bar as much as possible?

  • Have the humility to seek advice - Have the humility to admit someone is great at something and the extra humility to seek out their advice. Mentors are experts at a particular skill or topic, and you can reach out to them as needed. Coaches are long-term partners who share accountability for successes and failures. Build a bench of both to support yourself through the challenges of startup leadership.

🔍 Where to find Jared

🙏🏻 Thank you

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Best Manager Ever: Dana Lawson]]>https://annieriley.substack.com/p/best-manager-ever-dana-lawsonhttps://annieriley.substack.com/p/best-manager-ever-dana-lawsonWed, 03 Dec 2025 18:51:45 GMTDana Lawson is the CTO of Netlify, and was previously the VP of Engineering at Github and Director of Engineering at New Relic, Heptio, InVision (acquired by Miro), and more. Dana has a diverse background, starting her career in the military and working across different stages and industries. Only 8% of the world’s CTOs are women— and Dana’s one of the best!

Listen Now

In this episode, you’ll learn:

  1. How to combat imposter syndrome– even at the highest levels

  2. Why management is a role change (and not a new level or status)

  3. How to manage friends and former peers

  4. Why great managers should think like a detective

  5. How to handle interpersonal drama on your team

Direct reports describe Dana as:

  • Empowering and supportive

  • A great sponsor and confidence builder

  • Transparent, honest, and clear

  • Compassionate and kind

  • Drama-free

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Look at management as a change in role (not status) - When you transition from peer to manager, it’s not about suddenly being “above” anyone. It’s simply a shift in responsibility and roles. It’s not about hierarchy — it’s about taking on a different job that focuses on enabling others rather than producing the work yourself.

  • “Am I informed, or intimidated?” - When imposter syndrome overclouds the rational mind, the key is to go back and check whether you’re informed about a particular issue or topic. If you’re not informed, then put in the work to get informed. If you are well informed and still second guessing yourself, then it’s the imposter syndrome talking. Take a deep breath and remind yourself of everything you’ve been through to work through the intimidation.

  • Stop pretending you’re not friends - Relationship dynamics change when you go from peer to manager. Avoid falling into the most common traps: (1) Overcorrecting into cold “professionalism”, or (2) Remaining overly casual to avoid the change altogether. Instead, keep the friendship but dial up the honesty, open communication, boundaries, and mutual respect.

  • Think like a detective - Look for opportunities to make the business more efficient and effective. Treat everything you see as a “clue” about the system. Investigate what’s really going on and what solutions might exist. Make guesses and iterate based on what you try and learn.

  • Empathy and directness are antidotes for drama - When drama comes up, people most likely want to be heard. Listen to what they have to say and try to empathize with their perspective. Giving them space is not the same as endorsing or agreeing with them.

🔍Where to find Dana

📚 Referenced

🙏🏻 Gratitude

📈 Build your own leadership playbook

🤝 Stay in touch

✨ If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Best Manager Ever is a production of Fort Light and Now It’s Hear.

Thanks for reading Fort Light! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Best Manager Ever: Patrick Reynolds]]>https://annieriley.substack.com/p/best-manager-ever-patrick-reynoldshttps://annieriley.substack.com/p/best-manager-ever-patrick-reynoldsWed, 19 Nov 2025 17:06:26 GMTPatrick Reynolds is the Co-Founder and Head of Product at Office Hours, an expert marketplace. Patrick started his career as a software engineer, before becoming a self-taught designer and making the leap into product roles. Prior to co-founding Office Hours, Patrick worked at Affirm, Adobe, and several other early-stage startups and scaling companies.

Listen Now

In this episode, you’ll learn:

  1. The difference between leadership and management

  2. How to prime yourself so it’s easy to spot opportunities to support your team

  3. The difference between a culture that inspires ambition vs. enforces it

  4. How to consume content for maximum ROI

  5. The best way to spot (and stop!) perfectionism

Direct reports love working for Patrick, and they describe him as:

  • The most thoughtful, caring leader in big and small ways

  • The most prolific consumer of content, with near-constant references to podcasts, books, and blog posts that build his own knowledge and frameworks

  • Measured and clear – even in times of chaos and rapid growth

  • Maintaining a high bar of excellence for himself and the whole org

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Look for opportunities to create special moments - You need to look for little moments to help out the team, including removing friction and showing care. It’s impossible to know which moments will have a positive impact, so be consistent in how you show up.

  • Create a system to document notes for your team - Write down little things that happen along the way. Don’t rely on your memory to retain details, because you will likely forget. Use whatever system works for you, whether that’s a shared 1:1 doc for mutual notes, a private “shadow doc” for feedback and gift ideas, or whatever is most helpful.

  • Separate the process of curating content from consuming it - You can basically get a master’s degree using free podcasts, blog posts, and books. Expand your knowledge and build your own toolkit by consuming content deliberately. Separate the process from finding and curating content from the experience of consuming it so you can make the most of little moments to learn– whether on your commute, walking to/from meetings, or doing household chores.

  • Perfectionism is a dangerous trap - There’s a big difference between having a high bar and being a perfectionist. You can tell that you’re veering into perfectionism if fear and control are present. Perfectionism is a curse with no upside, and is the enemy of iteration and learning.

  • Approach leadership as a craft - Just like functional expertise, management is a craft and a skillset that gets built over time. Approach long days, setbacks, and learning moments as an opportunity to hone your craft.

🔍Where to find Patrick

🙏🏻 Gratitude

📚Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Best Manager Ever: Sophie Ruddock]]>https://annieriley.substack.com/p/best-manager-ever-sophie-ruddockhttps://annieriley.substack.com/p/best-manager-ever-sophie-ruddockWed, 12 Nov 2025 16:12:14 GMTSophie Ruddock is a seasoned operations and scaling leader. She’s currently the COO of Empathy, a mission-driven startup building support for life’s toughest moments of personal loss and tragedy.

Before joining Empathy, Sophie built her reputation at Multiverse, where she joined as employee #8 and grew from an IC to the global COO leading a 600-person org. She launched and led the company’s North America expansion to drive apprenticeship programs across Fortune 500 firms.

Listen Now

You’ll learn:

  1. The mindset shift required to scale yourself, along with your company and team

  2. What “radical ownership” really looks like

  3. The power of asking “what would it take?” instead of “is it possible?”

  4. How to earn the right to dissent

  5. How to show up for your team through crisis and loss

  6. Why the best leaders make themselves obsolete (and why that’s so hard!)

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Founder mindset is radical ownership and self-preservation - Sophie defines the “founder mindset” as radical ownership— taking full responsibility for outcomes at any level. But she’s quick to note that ownership doesn’t mean overwork. True leadership balances accountability with sustainability, knowing when to put your own oxygen mask on first.

  • Ask “what would it take?” instead of “is it possible?” - This is the mindset shift that takes doubt and turns it into action. Progress starts with curiosity, not constraints.

  • Fill holes, don’t just point them out - Great leaders build the trust to challenge well. Invest early in relationships so your feedback and contrarian ideas are heard as commitment to the mission, not criticism of others. Earn the right to be a dissenting voice, and offer solutions with the dissent.

  • Lead with humanity during life’s hardest moments - When team members face personal crisis, the approach is simple: prioritize people first, processes later. Offering space, flexibility, and genuine care builds loyalty and trust that no policy can manufacture— and strengthens the team for the long run.

  • Measure your leadership success by how little you’re needed - The true test of leadership isn’t how much your team relies on you, but how well they perform when you’re not in the room. When the people you’ve hired grow into senior roles, it’s proof that empowering others is the best approach for scaling your impact (and your legacy as a leader!).

🔍Where to find Sophie

🙏🏻Gratitude

📚Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨ If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Behavioral Science As A Leadership Tool]]>https://annieriley.substack.com/p/behavioral-science-as-a-leadershiphttps://annieriley.substack.com/p/behavioral-science-as-a-leadershipWed, 05 Nov 2025 17:12:28 GMTToday we’re trying something new on the podcast— it’s our first-ever expert interview! We LOVE sharing our leadership profiles, *and* we’ve heard it would be helpful to dig into specific topics, skills, and questions with experts who bring deep expertise and advice. Think authors, professors, and coaches. I hope you like this conversation, and this new format! I’d love to hear your feedback on this format— so please hit reply to share what you think, plus any topics or questions that you’d like to learn about. Enjoy! 💫

Listen Now

Matt Wallaert is a seasoned startup operator and applied behavioral scientist. He left his PhD program to make the leap from academia into the world of startups and tech. He’s currently the CXO at Oceans, and previously held leadership roles at Clover Health, LendingTree, Microsoft, frog design, and more.

In this episode, you’ll learn:

  1. Why all management is really applied behavioral science in action

  2. The “SIDE” framework — a simple, science-based way to drive lasting change in yourself, your team, and your company

  3. Why focusing on pressures (not people!) unlocks real behavior change

  4. How to make feedback more concrete, observable, and measurable

  5. How to run an entire behavioral science experiment in a single 1:1 meeting.

  6. Why science is the ultimate empathy engine

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Management is applied behavioral science - At the core of the job, every manager is in the business of behavior change— whether that’s influencing customers or coaching teams. Leadership is a science: experiment-driven, evidence-based, and focused on what people actually do, not what we wish they’d do.

  • The SIDE framework (Strategy, Insights, Design, Evaluation) - This is the simple four-step framework that turns behavioral science into action. Define the exact behavior you want (Strategy), understand why it’s not happening yet (Insights), design small interventions to shift pressures (Design), and test what works before scaling (Evaluation).

  • Focus on pressures, not people - Instead of labeling people as “lazy” or “unmotivated,” great managers look at the promoting and inhibiting pressures shaping behavior. Don’t focus on trying to change people. Instead, focus on what you can change— their environment to make the right behavior easier and the wrong behavior harder.

  • Make goals observable and measurable - Abstract values like “candor” or “collaboration” only work when translated into specific, observable actions. Ask: What does this look like in practice? Then measure those moments to build the culture and team norms you want.

  • Focus on pressures, not the behavior itself - Don’t focus on the behavior you’re trying to change– instead focus on changing the pressures that are influencing the behavior. What are the pressures that reinforce or incentivize the behavior, and what are the pressures that reduce or inhibit the behavior you want? You’ll want to experiment with both for all types of behavior.

  • This is a mindset and a muscle - Focus on incorporating this into your work in small ways to start. You can practice with yourself, or in a single 1:1. Share the framework with the team so you can use it together. Over time, the habit and muscle will become stronger.

  • Science unlocks empathy - Behavioral science is about more than data— it’s about understanding people as rational actors responding to their world. By seeing behavior as the product of pressures, not personality, leaders cultivate empathy, fairness, and more effective problem-solving across teams.

🔍 Where to find Matt

  • LinkedIn: https://www.linkedin.com/in/mattwallaert/

  • X: https://x.com/mattwallaert

  • Instagram: https://www.instagram.com/mattwallaert/

  • Book: https://www.amazon.com/Start-at-End-Matt-Wallaert-audiobook/dp/B07S389VL1/

  • Course: Free at LearnAppliedBeSci.com

🙏🏻 Gratitude

  • Thanks to the fabulous Mark Munro for the introduction to Matt!

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for reading! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Best Manager Ever: Amy Yamner Jenkins ]]>https://annieriley.substack.com/p/best-manager-ever-amy-yamner-jenkinshttps://annieriley.substack.com/p/best-manager-ever-amy-yamner-jenkinsWed, 22 Oct 2025 14:27:35 GMTAmy Yamner Jenkins is the COO at Meadow, an early-stage fintech startup working to change the financial experience for students and universities. Amy started her career as a classroom teacher, and pivoted into startups after working at NewSchools Venture Fund. Before Meadow, she was part of the building and scaling teams at Outschool and Education Elements.

Listen Now

This is an extra special episode for me, because Amy’s one of *my* best managers ever. I LOVED working with Amy at Outschool— she gave me tons of room to do my best work, served as a thought partner, and helped advocate and secure resources for my work. I learned so much from her then, and I’m delighted to have her as a mentor and friend to this day. 💖 It was fun unpacking our work together in this episode, and it’s a joy to share her wisdom with this Best Manager Ever community.

In this episode, you’ll learn:

  1. Why connection and context should always come before the content

  2. A simple 2x2 framework to build a consistent feedback practice

  3. Why the real work begins after the feedback convo

  4. How to notice and combat bias— especially in hiring

  5. Which words to ban from your leadership vocabulary

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Connection and context before content - Always invest in the relationship and share context about why something is important, before diving into what you want the team to do. Too often, we go straight to what we want to say, and skip the important steps of connecting and sharing context.

  • Don’t just operate in your default mode - Take a flexible approach for different direct reports. Be open to changing your approach where needed. Calibrate changes over time across different folks on the team, and take an iterative approach to learn what’s working with whom.

  • Bring feedback into interviewing - Exchanging feedback during the interview process gives you a strong signal for what work together will actually feel like. It’s less about giving feedback about their performance in the interviews, and more about talking through a work product (for example, reviewing a first version of their take-home deliverable and talking through it together).

  • Lean on a feedback framework - You’ll want to find a simple feedback framework that works for you (just like Amy’s 2x2 framework!), especially if your startup doesn’t have a company-wide feedback process. A simple framework helps build an ongoing, regular cadence of reflection and live feedback with your team— instead of falling into the trap of making feedback an “event” that happens just a few times per year.

  • Feedback is the start of the work - The real work starts once the feedback is exchanged. As a leader, you want to be clear about requests for your team. You also need to be clear about your own commitments to change (or not) and to follow through on those commitments over time.

🔍 Where to find Amy

🙏🏻 Gratitude

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨ If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on Apple or Spotify— this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for reading Fort Light! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Best Manager Ever: Adam Fishman ]]>https://annieriley.substack.com/p/best-manager-ever-adam-fishmanhttps://annieriley.substack.com/p/best-manager-ever-adam-fishmanWed, 15 Oct 2025 14:57:34 GMTAdam Fishman is an advisor and board member with 20+ years of experience building and leading startup teams. Adam was on the early team at Lyft, where he served as Head of Growth, before moving on to lead Product & Growth teams at Patreon and Imperfect Foods. Adam has been an advisor and fractional leader at ResortPass, Mozilla, HelpScout, Peerspace and more. He shares insights in the FishmanAF newsletter and is the creator and host of the Startup Dad podcast, where he talks about parenting from the perspective of dads who also happen to be founders, operators, and investors.

Listen Now

In this episode you’ll learn:

  1. The real job of a manager

  2. Why it’s important to set mutual expectations

  3. How to get more honest feedback from your direct reports

  4. What to do when you receive feedback that stings— and how Adam learned that lesson the hard way

  5. Predictions for how AI will impact product leadership roles

  6. How to know when (and if) a portfolio career is right for you

🎧 Listen now wherever you get podcasts: Apple | Spotify

Direct reports love working for Adam, and describe him as:

  • High trust and empowering– including giving the team room to make mistakes

  • A generative leader who comes from a place of “yes, and…”

  • Ambitious and rigorous

  • Making work fun, lighthearted, and goofy

Some takeaways:

  • A manager’s #1 job is to get the most out of people. Management isn’t about politicking, retention perks, or just making people feel good— it’s about helping your team perform at their absolute best. You’re building a championship team, not collecting friends.

  • Seek real feedback (don’t just be open to it) - The fastest way to grow as a leader is to get rich, honest input from your team. Don’t settle for the vague “Do you have any feedback for me?” Instead, create multiple feedback channels and ask specific questions about the things you actually want to improve. Invite critical feedback directly— it’s the only way you’ll get better.

  • When feedback stings, don’t defend. When you get tough feedback, your instinct might be to explain, justify, or promise a fix on the spot. Resist it. Instead: thank the person, ask clarifying questions, write it down, and then pause. Give yourself a night to process before deciding what to do with it. That reflection time is what turns painful feedback into lasting growth.

  • Invest in your own growth. Adam learned so much by “getting it wrong” early and then working with a leadership coach for years, practicing hard conversations, and pattern-matching over time. Rising leaders should view management as a skill that requires reps, reflection, and sometimes external coaching support .

  • Lead the way with AI - In this new AI era, a manager’s role is evolving, not disappearing. The job is increasingly about setting strategy and modeling the behaviors we want to see. That means experimenting with AI yourself, building with it, and openly discussing its impact on the team. Leaders who use AI to unlock leverage and clarity will help their teams thrive.

🔍 Where to find Adam

🙏🏻 Gratitude

📚Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe to stay in touch and support our work

]]><![CDATA[Best Manager Ever: Lauren Gold]]>https://annieriley.substack.com/p/best-manager-ever-lauren-goldhttps://annieriley.substack.com/p/best-manager-ever-lauren-goldWed, 08 Oct 2025 11:28:32 GMTLauren Gold is the Chief Customer Officer at Kustomer, an AI-powered customer service platform. Lauren built her reputation as an early employee at Yext, where she started as one of the very first GTM team members and grew to an SVP role leading a team of 60+ and managing over $400M in revenue.

Listen Now

Lauren’s team describes her as:

  • Delivering support and accountability– without ever micromanaging

  • Coaching and empowering problem-solving, not diving in and fixing

  • Invested in their growth and development

  • Proactive, clear, and honest communication

  • Exceptional at building a connected, fun team culture

In this episode, you’ll learn:

  1. How to be in the weeds without micromanaging

  2. Why you should be concerned when teammates go quiet– and what to do about it

  3. The difference between transparency and over-communication

  4. How to be a leader– regardless of your title

  5. The three questions you should ask yourself in every role

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Silence is a sign of struggle. When someone on your team goes quiet, it can be a sign of insecurity, overwhelm, or hidden risks. High-achieving, ambitious employees often withdraw when they feel they’re falling short, because they don’t want to be exposed. Seek them out. Approach them with inquiry to understand what’s really happening. Normalize problem solving and supporting together

  • Leadership is about how you operate, not your title. Do you take ownership? Do you lift up others? Do teammates see you as a problem solver? Leadership starts with influence, role modeling, and mindset– not titles or hierarchy.

  • Transparency and over-communication are NOT the same thing. Transparency is good, but proactive over-communication is even better. Whether it’s cascading insights from leadership meetings or clarifying priorities, Lauren stresses that clear, repeated communication builds alignment and trust. In fast-moving startups, silence leaves room for insecurity, anxiety, and disengagement.

  • Ask yourself three core questions. Rising leaders can use this as a compass to gauge whether they’re in the right role, stretching enough, and maintaining the energy that inspires their team. Come back to these three questions:

    • Am I learning?

    • Am I contributing?

    • Am I having fun?

🔍 Where to find Lauren

🙏🏻 Gratitude

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

PS - If you prefer to not receive posts about podcast episodes, just head to your Substack settings and opt out of the “podcast” section. No judgies!

Thanks for being here! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Best Manager Ever: Charlie Coglianese]]>https://annieriley.substack.com/p/best-manager-ever-charlie-coglianesehttps://annieriley.substack.com/p/best-manager-ever-charlie-coglianeseWed, 01 Oct 2025 15:09:23 GMTCharlie Coglianese is the CTO of Paloma, an edtech startup using AI to improve student learning outcomes.

Listen Now

Charlie started his career in finance, before making the leap into startups. He was the Founder & CEO of a startup called Schoolrunner, which was acquired by SchoolMint. Charlie served as the CTO at SchoolMint post-acquisition before returning to early-stage building in his current role.

Direct reports know Charlie for:

  • Proactively investing in his team’s career growth

  • Challenging and pushing his team

  • Bringing clarity, alongside deep care

  • Creating opportunities for “productive struggle”

In this episode, you’ll learn:

  1. The benefits of taking on smaller tasks so your team can do more

  2. Why you should be creating “productive struggle” opportunities for direct reports

  3. New perspective on empathizing with your founders

  4. The importance of honesty in building high-performing teams

  5. How to spot talent based on trajectory, not just results

🎧Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Keep people on your team interested and challenged - this isn’t about a path to another job or title, but about making sure your team is learning, growing, and finding excitement at work

  • You can take on lower-end tasks if it means freeing up the team to pursue more interesting and exciting responsibilities

  • We sprint, and then we walk. You can’t expect to sprint for the whole game– even if you’re the very best. Instead, you need to prioritize to make the sprints *worth it*, and then create breaks that give you moments to “walk”

  • Leaders can’t just dictate tasks, you need to *convince* others to go on the journey with you. Clarity of goals and mission will help, and you can’t skip the step of being courageous and honest.

  • Every team smells like its leader, so make sure you’re working on your own gaps and setting clear intentions for the type of culture you aim to build.

  • Productive struggle is important for growth. Make sure you’re creating opportunities for productive struggle on the team, and be ok with your team being uncomfortable. Learn the signs so you can spot productive vs. unproductive struggle, and jump in to help if the challenge becomes unproductive.

🔍 Where to find Charlie

🙏🏻 Gratitude

  • Thanks also to Charlie’s team for the feedback and stories about your work together: Sam Genduso & Scot Kerr

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Best Manager Ever: Karin Simelaro]]>https://annieriley.substack.com/p/best-manager-ever-karin-simelarohttps://annieriley.substack.com/p/best-manager-ever-karin-simelaroWed, 24 Sep 2025 11:45:28 GMTKarin Simelaro is the Chief Revenue Officer at SchoolAI, an AI platform that supports teacher and student success. Previously, Karin served as the Revenue leader at BrainPOP, Pathful, and Seesaw. She was an early employee at Nearpod, where started as the first field sales rep when the company was <30 people and around $10M ARR, and ultimately grew the business to over $100M ARR and a successful exit.

Listen Now

Karin is known by current and past direct reports for her:

  • High expectations for herself and others

  • Boundless, contagious energy and productivity

  • Transparency and openness

  • Fierce competitiveness and ambition

  • Deep connection with her team

In this episode, you’ll learn:

  1. How to evaluate performance amid the uncertainty of early-stage building using the “REKS” framework

  2. Why you should be doing a weekly “coffee and contemplation”

  3. How to act like an owner of the business— whether you’re an IC or C-level

  4. The best way to use AI to prepare, clarify, and communicate your thoughts

🎧 Listen wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Setting expectations is the most important leadership skill across all companies, no matter the size and stage. Define your “WGLL”— aka what good looks like (pronounced wiggle for funsies!)— and repeat it as often as possible. Clear expectations give the team comfort, and help them understand how to be successful.

  • The REKS framework is a useful way to evaluate performance, especially in the earliest stages when there’s so much uncertainty:

    • Results - What was achieved?

    • Effort - This is the one thing you can control in early-stage environments! So was it there, or not?

    • Knowledge - Are you missing some key information that you need to perform?

    • Skills - Is there a skill you’re lacking or could be doing better?

  • “Coffee & Contemplation” is an important weekly exercise— for us as individuals and across the team. Share notes across the team so leaders can understand trends across the org.

  • Use AI as a thought partner to help process and clarify your own thinking. You can dump all your thoughts into an AI tool, either via voice or writing. And then use the tool to refine and share your thoughts.

  • Be an owner for your piece of the business. This is about understanding what’s happening, what’s working (and what isn’t!), and why. You must have full command over your piece of the business, no matter the scope or size.

🔍 Where to find Karin

🙏🏻 Gratitude

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, we’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for reading Fort Light! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Best Manager Ever: Darius Contractor]]>https://annieriley.substack.com/p/best-manager-ever-darius-contractorhttps://annieriley.substack.com/p/best-manager-ever-darius-contractorWed, 17 Sep 2025 14:08:07 GMTDarius Contractor is the Chief Growth Officer at Otter.ai. Darius has had a long and impactful career in the startup and tech worlds. Prior to Otter.ai, he led engineering, growth and product teams at Vendr, Airtable, Facebook, Dropbox, Bebo and more. In addition to his full-time role, he’s also an investor and advisor in multiple companies and funds.

Listen Now

Darius’s direct reports love working with him, and describe him as:

  • A great leader who balances ambition and high expectations with fun and humanity

  • Extremely supportive of their growth, needs, and goals

  • An exceptional communicator– using analogies and frameworks that make concepts more memorable and work more fun

You’ll learn:

  1. The SEEN framework for career development

  2. How to help your team prepare for the next next job they want

  3. The importance of designing roles like dinner plates

  4. The zipper analogy to identify and fix misalignment

  5. How to balance performance with humanity

  6. How frameworks and analogies help make concepts stick

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Aim to grow your team by 20% each year - People can’t scale as fast as companies, so expect people to grow by an average of 20% each year. If you push too little below 20%, they get bored and leave. If you push too much beyond that, they’ll get overwhelmed. Aim for the sweet spot and calibrate for each person.

  • Only hire a new layer when you can get meaningfully better talent - You want to hire someone above your team when you can get someone at least 50% better than your current team, and ideally closer to 2x better. Otherwise, spend your energy developing the person on your team to do the job.

  • Use the SEEN framework for career development – Aim to hit at least two of these in a role, and aligning all four can create supercharged opportunities that keep top talent motivated and retained:

    • Strengths

    • Excitements

    • Edges/ growth areas

    • Needs of the company

  • Design jobs like a balanced dinner plate - A great role offers a mix of things, and managers should strategically shape roles to include competence, challenge and enjoyment. When you evaluate the “dinner plate” or role as a whole, the majority of the plate must align to the needs of the company:

    • 30-70% - things you’re already good at (confidence & value delivery)

    • 10-50% - stretch opportunities (challenge and grow)

    • 20-40% enjoyable work (keeps motivation high)

  • 1:1 meetings matter - Darius prioritizes one-hour 1:1s to go deep, coach, build relationships, and handle live issues. Whether your 1:1 meetings are one hour or ad hoc, you need enough meaningful communication to establish trust and enable growth

  • Analogies and frameworks make lessons memorable - Darius is known for using analogies to make concepts stick and feel fun. These analogies bring humor and levity to balance high expectations and keeping things joyful on his team.

  • Balance humanity and performance - Great managers don’t choose between a positive team culture and getting results. Darius blends compassion, humor, and personal connection with ambition, rigor, and accountability. Validate what’s real for individuals and the business, and then find a reasonable center point.

🔍 Where to find Darius

🙏🏻 Gratitude

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨ If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for your time today! Subscribe for free to receive more leadership lessons

]]><![CDATA[Best Manager Ever: Stevie Case]]>https://annieriley.substack.com/p/best-manager-ever-stevie-casehttps://annieriley.substack.com/p/best-manager-ever-stevie-caseWed, 10 Sep 2025 11:46:13 GMT

Stevie Case is the Chief Revenue Officer at Vanta. Stevie started her career as the world’s first female pro gamer, and then found her way into the tech and startup world through a self-described “crooked path”. Prior to Vanta, Stevie had a successful chapter at Twilio, where she started as an individual contributor and then grew to be the VP of Mid-Market Sales.

Stevie is an inspiring leader, and I hope you’ll enjoy learning from her as much as I did!

Listen Now

Direct reports love working with Stevie because of her:

  • Generative, empowering leadership style

  • Fierce and inspiring competitiveness, drive, and ambition

  • Ability to integrate ambition and competition with joy, fun, and silliness

  • Support and care for her team— as leaders and people

In this episode, you’ll learn:

  1. How Stevie has moved between IC and manager roles in her career (and why!)

  2. What a manager’s real job is— according to Stevie

  3. Why your direct reports are not your “first team”

  4. How Stevie vetted Christina as a potential CEO and boss

  5. How Stevie’s communication style has evolved as she’s become more senior and Vanta has scaled

  6. Why you should prioritize sharing your own story on LinkedIn, even amid a busy startup schedule

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Being a manager is NOT the only way to move up – When Stevie joined Twilio, she deliberately took a less senior IC role to learn the business and make an impact… which ultimately helped her advance to VP over time.

  • Your job is to help direct reports operate independently - Your job is not to control the outcomes of your team’s work, or to make sure that you get perfect results every time. Instead, your goal is to get out of the way and allow your team to run. Mistakes and failures are inevitable parts of the process, so accept them now. Focus on helping your team scale as leaders who can operate without you.

  • If your team is off track, turn the blame towards yourself - If multiple team members are off track or making bizarre suggestions, then the blame is on you. Their confusion is mostly likely because you haven't been clear about priorities and guardrails. If you get very clear about priorities, then you create the conditions for them to run within those guardrails… and set yourself up to say “yes” to their suggestions.

  • Your first team is not your direct reports— it’s your peers - Invest in building a “first team” that feels connected, trusting, and constructive. Your “first team” performance is important for your success individually, but also for your direct reports’ success too.

  • Work with people whom you genuinely respect, like, and trust. There are a lot of smart and capable leaders out there, but you need to find the ones whom you want to be around, learn from, and support to have lasting, thriving work relationships.

  • Saying the harsh truth is a key skill for managing up - Stevie is known for a clear, direct, transparent communication style. And yet she still works to build her communication skills, and makes a deliberate effort to say the hard truth when needed. If you can build the skill of speaking the truth in a clear and constructive way, then you become invaluable to your own manager.

🔍 Where to find Stevie

🙏🏻 Gratitude

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a quick rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • Reach out to sponsor an episode or podcast club: sponsor@fortlight.com

Thanks for being here! Subscribe to receive new posts and support my work.

]]><![CDATA[🎙️Welcome to Best Manager Ever Season 3]]>https://annieriley.substack.com/p/welcome-to-best-manager-ever-seasonhttps://annieriley.substack.com/p/welcome-to-best-manager-ever-seasonWed, 03 Sep 2025 12:54:26 GMTHi there - Annie here. I’m excited to share that Best Manager Ever Season 3 is out in the world today! 🎉

I’m super proud of this season and am delighted to share it with you!

This show is for every ambitious operator who wants to build winning teams, drive exceptional results, and be the type of leader that teammates never forget.

I want this podcast to feel like an expert mentor in your pocket— where you can just show up, hit play, and get valuable insights that help you feel stronger and perform your best.

Check out all the details below, and please reach out with questions, feedback, or suggestions for how we can make the show even better for you.

Thanks for your time and support of the show! ✨
Annie Riley

Check Out The Trailer

Here’s what you can expect from Season 3:

  • Honest stories about mistakes and lessons learned based on lived experience (no theory or hypotheticals!)

  • Trustworthy insights from leaders who are endorsed by their teams as the best manager they’ve ever worked for

  • Actionable advice that you can apply immediately

  • Startup-specific lessons to help you manage in a fast-paced, high-stakes, resource-constrained, uncertain contexts

  • Inspiring conversations that share the human side of leadership— not just rehearsed success stories

And for the first time ever, we’re featuring interviews with select experts who go deep on leadership topics that matter most, including authors, professors, and leadership coaches. Adding this new format is a fun experiment, so I’ll be curious to hear your feedback.

Here are just a few of the amazing guests you’ll learn from this season:

New episodes drop every Wednesday, starting September 10th.

🎧 Listen wherever you get podcasts. Don’t forget to subscribe on your fav podcast app so you never miss an episode (including Apple & Spotify).

Listen Now

If you’re enjoying the show and have a few moments to support on this big launch day, we’d so appreciate your help to spread the word:

  • Engage with this LinkedIn post

  • Subscribe to the show on your fav podcast app

  • Leave a rating or review on Apple and Spotify

  • Leave a ❤️ on this Substack post

I appreciate your support and am grateful to have you in our corner!

Best Manager Ever is a production of Fort Light and Now It’s Hear.

If you know an amazing leader who’d be a good fit for the show, nominate them here.

If there’s a leadership topic that you’d like us to cover on the show, hit reply and let me know— I’d love to hear from you!

If you’re interested in sponsoring an episode, reach out: sponsor@fortlight.com.

Thanks for being here! Subscribe to stay updated on podcast episodes and other startup leadership lessons

PS - If you prefer to skip the podcast episode announcements but want to stay in the loop about other Fort Light lessons and updates, just head over to your Substack account, select “manage subscription,” and toggle off podcast notifications. No judgies :)

]]><![CDATA[Standout Lessons from Best Manager Ever Season 2]]>https://annieriley.substack.com/p/standout-lessons-from-best-managerhttps://annieriley.substack.com/p/standout-lessons-from-best-managerWed, 25 Jun 2025 18:10:10 GMT

Listen Now

🎧 Listen now wherever you get podcasts: Apple | Spotify

Top takeaways:

Thanks for reading Fort Light! Subscribe for free to receive new posts and support my work.

  • Hire people who scare you – When you meet a candidate and can’t imagine the limits of their capabilities, hire them immediately. Look for a caliber of talent where you’d be delighted to report to them down the line. This will raise the bar on the team, and allow everyone to do the very best work of your careers. As a bonus, it will help you build a longstanding, valuable network that pays dividends long after this job ends.

  • Conventional approach = conventional results - If you’re looking for the most common way of doing things, you will inevitably end up with common results. If you notice yourself seeking answers externally and indiscriminately implementing playbooks, that’s a signal to think more critically. Ask yourself, “what’s the job to be done here?” And then coach yourself (and your team!) to surface unconventional ways of doing things— this is more fun, and creates space for unconventional results.

  • Proactively seek out dissent and concerns - You can’t just be open to dissent. You also need to proactively seek out disagreements, surface concerns, and tackle awkward conversations head-on. Set the expectation that disagreement is only constructive when it’s discussed openly in the room (vs. via backchannels and side Slacking)

  • Development is part of the job - Growing yourself is a fundamental part of the job, and NOT something extra. You need to be diligent and committed to development on the job. If you’re a manager, then it's your job to do this for yourself— and to help your team! Empower your team to prioritize their development, and connect them with opportunities to grow.

  • Our work can be bigger than the work itself - Find moments of joy, connection, meaning, and fun along the way. When we invest in management and leadership, it becomes about something bigger than the work… and the work and connections become a bigger part of our lives and journeys.

🙏🏻 Gratitude

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for reading! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Sruthi Lanka: Hire People That Scare You]]>https://annieriley.substack.com/p/sruthi-lanka-hire-people-that-scarehttps://annieriley.substack.com/p/sruthi-lanka-hire-people-that-scareWed, 18 Jun 2025 12:47:47 GMT

Listen Now

Sruthi Lanka is the CFO of Public.com. Sruthi started her career as an engineer building products at Goldman Sachs, before becoming an investment banker. She moved into startups in 2017 after a successful career in finance, and became the VP of Strategic Finance at MoneyLion, where she helped scale the company from early-stage through SPAC IPO.

Sruthi joined Public in 2020, and has been dedicated to building ever since.

Her team describes her as the most strategic, innovative, and supportive manager they’ve ever worked for. Just a few of the highlights they shared about Sruthi:

  • A visionary leader, who sets a clear direction for the business

  • The most connected, “in touch” exec

  • A deeply caring manager, who’s invested in the growth of her team

  • Fun, joyful leader to be around– even when stakes are high

  • An innovator one step ahead of tools and industry trends

You’ll learn about:

  1. Hiring a high-caliber team— at a talent level that scares you ;)

  2. Running lean on headcount, but not on investment

  3. Staying one step ahead on innovations and industry trends

  4. Leading through metrics and growth levers

  5. Partnering well across finance and operations

  6. Building new skills outside of your functional area to become more effective

  7. Leading with both competence and connection

🎧 Listen wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Hire people who scare you - If you’re interviewing someone and can't imagine the limits of their capabilities, then hire them immediately! Resist the urge to hire folks you can control. Instead, optimize for excellence and hire people who could take your job. Invest time in finding these people, instead of rushing the process. Once they are hired, give them TONS of responsibility and autonomy to enable a big impact.

  • Run lean on people, not on investment - A lean team allows people to do the best work of their lives. To make a lean team work well, hire people who bring multiple skillsets and make sure you’re investing in the tools, automations, and support they need to do their job well.

  • Figure out the formula for your business, and focus on drivers - Find the simplest, most elegant equation that drives your business (and remember that simple is not easy!). Even the most aggressive numbers have structured formulas behind them. Do the work to understand the formula and the levers, and focus on how you and your team can make an impact.

  • Lead with curiosity and build skills outside your immediate area - This is the best way to develop context, collaborate well with other teams, and build a deeper understanding of the overall business. Build your skills, grow your impact, and level up in your career.

  • Combine competence and connection - Show up with excellence, and build authentic connections at work. Find work environments where it’s possible to do both. Everyone deserves to find joy at work, so if you’re not experiencing it, then ask yourself if it’s possible to align your personal values with the culture. It’s about living a full life, and doing your best work.

🔍 Where to find Sruthi

🙏🏻 Gratitude

📚 Referenced

  • Goldman Sachs: https://www.goldmansachs.com/

  • MoneyLion: https://www.moneylion.com/

  • RBC: https://www.rbccm.com/

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe so you never miss an update.

]]><![CDATA[Asheesh Birla: Embracing Risk and Cultivating Talent]]>https://annieriley.substack.com/p/asheesh-birla-embracing-risk-andhttps://annieriley.substack.com/p/asheesh-birla-embracing-risk-andWed, 11 Jun 2025 15:40:33 GMT

Listen Now

Asheesh Birla is an investor, advisor, and board member. Asheesh joined Ripple in 2013 when the team was still under ten people. He had an amazing run building Ripple for almost a decade–– leading the product team, and wearing many different hats as the company scaled. Asheesh was such an important member of the team that the founders asked him to join the board, and he continues to serve as a Ripple board member today.

Asheesh’s team knows him for:

  • Visionary leadership

  • Setting a high bar for himself and the team

  • An intensity and passion for work

  • Positive energy, humor, and fun

  • A commitment to coaching and development– for himself and his team

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • When you ask your team for something, be willing to do it 2x - As the leader, your behavior sets the tone. There will be moments when you need to ask your team for intensity. You need to be willing to live up to those expectations yourself— and more!

  • Set clear expectations during the hiring process - It can be tempting to emphasize all the benefits. But instead of selling perks, focus on how you plan to win (including working harder than anyone else). This will attract a certain type of person… and persuade folks who don’t want that to go elsewhere.

  • Hiring your team is just the starting line - You need to approach hiring as the starting line, not the finish line. Put in the time and energy to develop and retain your team over time, even when things are busy.

  • Developing talent is about investing and divesting - You develop a strong, high-performing culture by managing talent in two ways. First, promote and invest in the people you want to retain. And then, you also need to part ways with folks who are not working out.

  • Let your team shadow your work - Letting your team shadow your work and meetings is one of the best, most efficient ways to help them learn. You give them access to new conversations, skills, and relationships, simply by letting them tag along to work you’re already doing.

  • More startups should invest in coaching for the team - Coaching can be such a useful resource for team members. More startups should invest in coaching for high-potential employees, and not just the founders.

  • Add a little sweetness to bitter things - Difficulties, challenges, and hard decisions are inevitable. When you need to make a tough call or endure something unpleasant, add a little sweetness to that bitter thing— whether that’s bringing pastries to the 7am meeting, or whatever works for your team :)

🔍 Where to find Asheesh

🙏🏻 Gratitude

📚 Referenced

  • Ripple: https://ripple.com/

  • Chris Larsen: https://x.com/chrislarsensf

  • Brad Garlinghouse: https://x.com/bgarlinghouse/

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe for free to receive updates.

]]><![CDATA[Lauren Rhode: Grit, Teamwork & Humility]]>https://annieriley.substack.com/p/lauren-rhode-grit-teamwork-and-humilityhttps://annieriley.substack.com/p/lauren-rhode-grit-teamwork-and-humilityWed, 04 Jun 2025 12:14:46 GMTA quick heads up that we just launched a new community (!) for managers and team leads at startups to learn and connect with each other, and with experienced coaches and exec-level leaders from different functions and companies. Learn more here, and reach out if you’d like to get involved— or even better, share it with a high-potential leader on your team whom you’d like to invest in.

Listen Now

Lauren Rhode is currently the VP of Sales at Webflow, and she’s had several interesting chapters to her career. Lauren got her start in public service, working at the department of defense. She’s also an avid rugby player and coach, and traveled around the world competing for Team USA. She started her tech career in product, before discovering her knack for sales. Before Webflow, Lauren helped scale Bablestreet (formerly Vertical Knowledge) and Anaplan.

Lauren’s team shared amazing things about working with her, including just some of her strengths:

  • Setting the tone for performance, work ethic, and speed

  • Deliberate and empathetic thoughtfulness

  • Deep, collaborative support for her team

  • Creating warm and collaborative virtual interactions

You’ll learn:

  1. How Lauren’s varied career experiences inform her leadership style

  2. Principles for management and leadership

  3. The dangers of (mis)perceiving that anyone “has it all together”

  4. Discipline as a leadership skill

  5. Aligning schedules to key priorities

  6. The importance of preparation for performance and collaboration

  7. Tips for creating collaborative, human virtual interactions

  8. How to deal with leadership transitions in scaling companies

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Grit, teamwork, and humility - These are key lessons from competing at the highest levels of rugby and leading teams. Discipline is critical for being proactive and setting yourself up for success. Teams win or fail as a collective, and are greater than the sum of individual parts. And no matter how hard we work, there will always be setbacks— so we stay humble and try to learn from challenges.

  • Aim to capture the win and learning - Ideally you want to achieve both the win and the learning. But sometimes it’s not possible to get both. Even if you don’t win, it can still be a victory if the lesson contributes to your learning.

  • There are no silver bullets, and no one is perfect - Things will inevitably go awry, even for seasoned leaders like Lauren who project so much confidence, competence, and togetherness. The perception that anyone is perfect is dangerous. Expect setbacks, and be compassionate with yourself when they come up. The key is coming back to the discipline, and bouncing back after challenges.

  • Balance out high-pressure moments - There will always be more work to do, and there are moments that require all hands on deck. Take advantage of opportunities to move a little slower, in order to balance out the moments that require you to sprint.

  • Set your priorities, and align your schedule - Be clear about your top priorities, and make sure your calendar reflects those priorities. If the schedule is not aligned with the most important things, then it’s up to you to rearrange your calendar.

  • Act as the CEO of your domain - You’re in charge of yourself and your work. Discover your autonomy, purpose, and mastery to find intrinsic motivation, and to control what you can (while letting go of things you can’t control).

  • Be clear with the vision and flexible with the details - Within the big picture vision, create the space and creativity to decide how to get things done. Have strong beliefs, but hold them loosely so you can be flexible and adaptable based on setbacks or new information. This can apply to work and life!

  • Have conversations in the room - Encourage honest, open dialogue during live conversations. Lauren doesn’t tolerate 1:1 side conversations or back-channeling. Instead, she creates the space and expectation that dissent must be shared openly in conversation.

  • Consider how you show up virtually - Too often, we check our humanity at the door in virtual meetings and Slack. In virtual meetings, notice how your body language is showing up and choose to lean in. In Slack, give acknowledgement that you’re present and engaged. Little things can go a LONG way here!

  • Leadership transitions have a silver lining - Accept that leadership transitions are part of startup life. Remember that layers can be added at any time, and bring a mindset that you are working yourself out of a job. Build as much as you can, and be willing to share and hand things off. As much as possible, use these transitions as a learning opportunity.

🔍 Where to find Lauren

🙏🏻 Gratitude

📚Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe for free to receive new posts and support my work.

]]><![CDATA[Leanna Nazzisi: From Part-Time to Power Player ]]>https://annieriley.substack.com/p/leanna-nazzisi-from-part-time-tohttps://annieriley.substack.com/p/leanna-nazzisi-from-part-time-toWed, 28 May 2025 17:22:03 GMTA quick heads up that we have space in a few upcoming Fort Light cohorts for high-potential managers and team leads at startups (Series A through growth stage). We cover the interpersonal skills required to build high-performing teams, as well as the inner work needed to win and thrive on the rollercoaster of startup life. Learn more here, and reach out if you’d like to explore— either for yourself, or for a rising star leader on your team whom you’d like to invest in: info@fortlight.com.

Listen Now

Leanna Nazzisi is the Senior Director of Customer Experience at Victoria Beckham Beauty, a clean, cruelty-free, digital-first makeup and skincare brand founded by the one and only Victoria Beckham (!).

Leanna launched her startup career as a seasonal contractor with Birchbox, where she rose through the ranks to become a senior CX leader as the company scaled. She also had a chapter as a customer success leader during Zendesk’s growth stage.

Leanna is known as an exceptionally strong leader and CX wizard. She was nominated by her team, several of whom followed her from Birchbox to VBB. Her team knows her as:

  • Proactively eliciting ideas and really listening

  • Matching the business needs with the strengths and needs of the individuals on the team

  • Building a sense of trust and authenticity

  • Creating a culture of transparency, honesty, and clarity

  • Balancing high-level strategy with detailed execution

You’ll learn:

  1. How Leanna went from a part-time seasonal contractor to the leader of a global CX org for a top beauty brand

  2. Strategies for managing former peers and friends

  3. How to create a consistent team-wide mindset

  4. The importance of proactive, exceptional customer experience

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Pursue roles where you love the product - Leanna has moved up in her career by working for companies where she loved the product. This is such a cheatcode for job seekers!

  • If you’re moving up, others can too - Leanna rose through the ranks, and has managed folks who are more experienced than her or were previously peers. She viewed her own rise as a signal that there are also opportunities for others, and took on the responsibility of connecting her team with those opportunities.

  • Don’t skip the foundation - If you’re leading a function, then you need to be familiar with the day-to-day mechanics of that group. For example, CX leaders need to be trained as an agent first. If you don’t understand the basics, you’ll never know what needs to be improved.

  • Customer experience is a mindset - CX is not about giving things away for free – it’s about a memorable, valuable experience. If you’re building a team, think about the attitude and mindset that you want to instill, and then hire and coach towards that.

  • Trust your team to co-create the plan – If you hire the right people and trust their experience, you can share big ideas and get their insights to punch up the plans. Your team will be more motivated and engaged when they understand the plan, and are bought in from the beginning.

  • Support teams have the real scoop - If someone knows the juicy details about what’s going on with customers, it’s the support team. No matter what function you lead, get curious and ask the support team about what they are seeing, thinking, and feeling.

  • Aim for the right level of discomfort - Changes inevitably bring discomfort. As the leader, it’s your job to understand the root of the discomfort. This helps you understand what (if anything) you want to do about it.

  • Tackle the awkwardness head-on - Be transparent and address the elephant in the room. Acknowledge any weirdness, and talk about what can be done to make things less awkward. This is particularly important if you start managing someone who is a friend or was a peer.

  • Managers are responsible for your team's growth - It's your job to share information about what is available at the company and to make team members feel valued. If someone is putting in notice without your knowledge, it’s a huge miss.

  • Go all-in on the most important problems - If you tackle one major problem at a time, then it helps the team prioritize. It can reduce stress and help the team focus. And then it’s your job as the leader to communicate those priorities to the rest of the org.

  • Pick an area to shine - Leanna was able to stand out as an IC by focusing on the data. Find your top priority, and make it something that is interesting and enjoyable to you. Then become excellent at that, and make sure to share your knowledge across the org so you can become known for it.

  • Education, Convenience, Connection - These are Leanna’s pillars for the CX team. She applies these principles to her customers, as well as to her team internally.

🔍 Where to find Leanna

🙏🏻 Gratitude

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨ If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe to make sure you never miss an update

]]><![CDATA[Amit Shah: Harnessing Energy, Gratitude & Learning]]>https://annieriley.substack.com/p/amit-shah-harnessing-energy-gratitudehttps://annieriley.substack.com/p/amit-shah-harnessing-energy-gratitudeWed, 21 May 2025 12:20:45 GMTWe’re launching a new community for managers and team leads at startups (Series A through growth stage). This will be a unique space for high-potential leaders to connect, grow, and thrive— alongside talented peers and seasoned mentors like our Best Manager Ever guests. I’m super excited about this and hope you’ll check it out! Founding member pricing is available before the 6/1 launch. More details and apply: https://www.fortlight.com/community

Listen Now

Amit Shah is the COO of Virta Health, where he’s built the company from a team of ~30 to over 800 colleagues working to reverse obesity and diabetes. Amit is beloved by his direct reports for his enthusiasm, passion, and deep care for Virta’s team and members.

Prior to Virta, Amit started his career in management consulting, launched a solar company in rural India, and worked at Paladina (a startup within DaVita Health).

Amit’s Virta team raves about working for him for so many reasons, but here are just a few of the things that stood out:

  • Relentless enthusiasm, energy, and passion for the Virta team and mission

  • Deep commitment to learning, improving, and growing

  • Reporting on learning and development progress like business metrics

  • Balancing detailed execution with big-picture thinking

  • Authentic care, loyalty, and protection for his team

In this episode, Amit is super generous about sharing lessons learned and displays the openness, humility, and growth mindset that his team knows and loves him for. You’ll learn:

  1. Amit’s leadership journey and key lessons along the way

  2. How to build a gratitude practice that supports your team – and yourself

  3. The importance of emotional awareness and regulation in leadership

  4. Energy management habits and practices

  5. A process to take charge of feedback, learning, and growth

  6. The relationship between execution and strategy in startups

  7. Mistakes and lessons learned along the journey of building Virta

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • To build your leadership style, consider your experience as a direct report - We’ve all been managed before, and you can decide how you’d like to show up by looking back on your own experience as a direct report to different managers. Try to replicate things that worked well, and avoid the things that didn’t.

  • You can’t pour from an empty cup - If your energy is depleted, it becomes impossible to pour into other people— including your team and customers. Identify the things that support and sustain your energy as a leader, and incorporate those practices consistently.

  • Build a practice of gratitude and praise with your team - This makes things more positive for everyone! It’s all about picking a practice that works for you, whether that’s sharing a win of the week, building a habit of saying thank you, or whatever works for you. It feels good for you as the leader, and it creates more grace when it’s time to talk about things that aren’t working well.

  • Pay into the relationship bank account proactively - A healthy relationship has a 5:1 ratio of positive to critical feedback. Invest in the relationship bank account with your team members proactively and deliberately via gratitude, praise, and positive feedback.

  • Be mindful of interactions as you get more senior - As the company grows and you get more senior, many team members will get fewer firsthand interactions with you— which means every interaction matters so much more for how they experience and understand you. Be deliberate and thoughtful (but don’t overthink this!).

  • Notice your negative patterns - We all have moments when we’re not showing up as our best selves. Become familiar with your triggers and patterns. Review your calendar in advance to mitigate challenging moments that might pop up, and set yourself up for success.

  • Name emotions in the moment - Negative emotions like anger, frustration and disappointment are normal parts of life and work. When they come up, name them to yourself, and disclose them to trusted colleagues. Labeling specific emotions allows us to process the feeling, and clues them into what’s happening for us— so they don’t need to guess.

  • Pause > Disclosure > Why - This is a 3-step process to sharing emotions, especially negative ones! First, take a pause and notice what’s coming up for you. Then, disclose it— whether it’s a thought or emotion. Finally, explain why it’s happening for you, to open the door to a productive conversation.

  • Run your own feedback process - You don’t need a HR-approved performance process to collect feedback and set goals for yourself. You can ask questions of your team to gather input, evaluate how you’re doing, and set priorities for what to focus on.

  • Share your development goals - If you’re going to ask the team to spend time giving you feedback, then you need to share what you heard and what you plan to do about it. Disclose what you’re working on, so that your team can support, hold you accountable, and give you some credit for it. This is also a great way to lead by example, when you’re asking the team to improve their own skills.

  • Let people know what you WON’T get better at - The team will give more grace if they know you won’t make meaningful improvement in a certain area. Everyone knows you can only prioritize a finite number of things, and it’s much better to understand what’s not a top priority, instead of perceiving that you don’t know or care that about the issue.

  • Leadership is a craft you can improve - Just like you can improve your cycling time or learn a new language, you can hone the craft of leadership! Think about leadership as behaviors and skills, instead of an innate thing.

  • Execution is a muscle that informs strategy - Leaders often spend too much time shifting strategy, instead of improving their execution. If you stay focused on improving and iterating on execution, you make strides and capture learnings that inform strategic decisions.

  • Be kind to yourself on the journey of learning - Sometimes we miss the mark. It’s a normal part of the human experience. No one gets it right all the time. Learn from missteps, and move forward.

🔍 Where to find Amit

🙏🏻 Gratitude

📚 Referenced

📈 Build your own leadership playbook

🤝 Stay in touch

✨If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this helps us spread the word about the show!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

🎙️ Best Manager Ever is a production of Fort Light and Now It’s Hear.

Thanks for being here! Subscribe to get future updates

]]><![CDATA[Liz Ludwig: Building Momentum]]>https://annieriley.substack.com/p/liz-ludwig-building-momentumhttps://annieriley.substack.com/p/liz-ludwig-building-momentumWed, 14 May 2025 15:39:51 GMTThis Friday May 16th from 9-10am PT, we’re hosting a free virtual workshop focused on managing up effectively— especially on the rollercoaster of startup life. We’ll share lessons learned from senior operators and workshop live challenges with peers and mentors in an interactive session. Come join us!

🔗 Details and RSVP.

Listen Now

Liz Ludwig is the co-founder of Takes, an app for sports fans to interact over live games. Liz started her career working in Fortune 500 companies, before moving into the startup world. She has a track record of success building and scaling marketing orgs at Sungevity, OhmConnect, and more.

Liz’s team raves about working for her. Here are just a few of her strengths:

  • Building meaningful relationships with her team that outlast the role

  • Creating momentum and excitement

  • Cutting through the noise and prioritizing the most important things

In this episode, you’ll learn:

  1. How to turn ambiguity into a management advantage

  2. The importance of hiring and firing fast— especially in early-stage building

  3. How to help direct reports find their best role

  4. Tactics for smooth team transitions

  5. Communication strategies and skills

  6. Advice based on Liz’s transition from operator to founder

🎧 Listen now wherever you get podcasts: Apple | Spotify

Some takeaways:

  • Ambiguity can be a management advantage - Early-stage environments have a LOT of uncertainty and very few “policies”. Use this as an advantage, instead of an obstacle. It gives you a lot of room to lead however you want and need to.

  • Get your team to understand the potential - When you’re building at the early stage, it’s not possible to predict how things will go or what career trajectories will look like. But if you can communicate a clear vision and hire people who believe in it, then the right people will run through walls to make things happen.

  • Hire folks who balance out your strengths - Figure out your strengths and patterns, and then hire people who complement that. For example, if you’re not super into details, hire people who are more detail-oriented.

  • Give new hires a quick win - Pick a project for a new hire to do in their first few weeks that you know they will crush. This makes everyone feel great, and creates momentum for the new hire.

  • Hire fast, and fire fast - Early-stage hiring requires you to hire people quickly, and fire folks fast when it’s not working. Learn about their motivation and passion, and understand how they think about adding value to the business. Then make decisions based on those.

  • Ask your team “how do you think this is going?” - People will tell YOU if it’s not working out. If someone is flailing, they know it. Ask the right questions and create the space to tease out how things are going.

  • The golden rule is a useful guide - Ask yourself “what would I want from a manager in this situation?”. Then use it as a guide for your own actions.

  • Helping your team with an exit can build long-term trust - You have your own relationship with direct reports outside of the role, and parting ways in the short-term doesn’t mean they are permanently exiting your orbit. Think of an exit as helping them transition to the right place for them.

  • Alternate filters for 1:1 conversations - As a leader, you can use 1:1 meetings to discuss many different things. Change up the topics across those meetings, whether it’s unblocking projects or talking about big-picture life goals.

  • Ask your team to help design their backfill - When someone is leaving a position, ask them what their backfill should look like, including the job description, structure, and hiring profile. You get the benefit of their perspective, and build the relationship with the direct report.

  • Take signals from others about how to communicate - People have different preferences and styles, and you need to adjust your approach based on who you’re working with. When in doubt, have a conversation about communication preferences and negotiate how you’ll partner together.

  • Address the elephant in the room - You need to constantly check for alignment by repeating the goals, and checking for concerns and disagreement. The team is inside the room, and fighting forces outside the room.

  • Mentors are out there, but it’s on you to make the ask - Keep up your network, even while you’re in intense jobs. And along the way, find mentors who can share their wisdom and help you grow. Most people are happy to help – you just need to ask, and be flexible with when and how it happens.

  • Empathize up with your founders - Remember the business feels even more personal to them, and their identity is wrapped up in the outcome. Try to empathize with their challenges, and know they might take over sometimes… it’s about them, not you.

🔍 Where to find Liz

🙏🏻 Gratitude

📈 Build your own leadership playbook

🤝 Stay in touch

Best Manager Ever is a production of Fort Light and Now It’s Hear.

✨ If you enjoy this episode, I’d so appreciate your support:

  • Subscribe on your favorite podcast app so you never miss an episode

  • Leave us a rating or review on your fav podcast app — this is super helpful for spreading the word!

  • If you’ve worked for an amazing leader who’d make a great guest for the show, nominate them here: https://dub.sh/BMENominate

  • To explore sponsoring a future episode, reach out: sponsor@fortlight.com

Thanks for being here! Subscribe for more leadership lessons

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