Fort Light

🎙️Best Manager Ever Season 2 is HERE, and I'm super excited to kick off new episodes with Anthony Sottile, VP of Partner Success at FreeWill. Anthony’s team loves working with him, and it's easy to see why -- he models resourcefulness, proactively reaches out to support, brings humor and play, and rewards both what they accomplish and how they show up. A few of my top takeaways from this convo with Anthony: 1️⃣ Failure provides focus - Instead of trying to avoid failures, use them as learning moments to improve and refocus  2️⃣ Celebrate big and small  - Find ways to celebrate wins with your team, whether it’s a big tradition like Anthony’s “Ozcars” ceremony 🏆 or a good ol’ party parrot conga line (IYKYK 🦜) 3️⃣ Recognize more than just results - Outcomes matter, and so does *how* we get there. Reward behaviors you want to reinforce, like overcoming challenges, embodying values, and uplifting others 🎧 You can listen to the episode linked in comments, and check out more detailed takeaways in our Substack. What’s a leadership lesson from Anthony that stood out to you? Reach out or drop it in the comments – I’d love to hear! --- Big thanks to Anthony for joining us, and to his team for the nomination, plus great stories and feedback: Virginia Fay Pack, Nick Kim-Skenderian, and Kelly Jo Drey. --- Best Manager Ever is a production of Fort Light and Now It's Hear. Thank you to my partner in crime and producer Alexis Elizabeth Ramdaou for everything -- I'm super proud to launch season 2 with you! 💕 ⭐ If you enjoyed this episode, remember to subscribe and leave us a review on your fav podcast app. It’s the best way to stay updated about future episodes, and helps us reach new listeners who might benefit from the show.

If you’re job hunting, you’re probably looking for both: (1) an amazing manager and (2) a company that truly invests in its people. The good news is, we know some of those at Fort Light 🙃, where we have the good fortune of working with leaders and companies that don’t just talk a big game about leadership and culture -- they actively invest in it and build it into their work. I'd like to highlight exciting opportunities in our network, with leaders and organizations that are serious about growing their business and their people. ✨This week, check out our friends at Office Hours. Office Hours is building game-changing tools for the knowledge economy, and they’re hiring across multiple roles and functions. One standout, entry-level opportunity: Their Client Solutions Architect roles in NYC and SF, reporting to Anna Bennett and Andrew Y. Sommer -- both Fort Light alums and engaged members of our community. Having worked with Anna and Andrew firsthand, they are thoughtful, driven managers who care deeply about their teams *and* results. If you’re looking for a new company where leadership and culture truly matter, any role at Office Hours could be a great fit. PS: I’ve also been a customer of Office Hours and highly recommend checking out their platform -- whether for your own research, or as an expert sharing your insights. 🔗 I’ll drop their jobs page in the comments, in case you or someone you know is looking!

A few weeks ago, I participated in a 2-day coaching/leadership program hosted by Fort Light. As I reflect on the sessions, I want to share a big, big thank you to Annie Riley, Dr. George Philip LeBourdais, Diane Loviglio, and Arup Chakrabarti for creating such a wonderful experience. A few things that stood out to me: 🤍 The thoughtfulness of the program's design 📓 The practical application of tools and frameworks to real startup challenges 🔍 The depth of self-reflection facilitated It was also such a refreshing opportunity to step out of the day-to-day and get to know a lovely group of people from different industries and areas of the startup world. For any startup operator or non-founder exec looking to to learn new skills (for work & life) and to level up on leading/scaling, I highly recommend checking out Fort Light! I am grateful to have had the chance to join this cohort and I can't wait to be a part of the Fort Light community in the years to come.

👋🏻 Hey there Fort Light alums and community members -- We're hosting our first-ever quarterly skills refresher tomorrow, March 3rd. This will be a space to sharpen your skills, workshop live challenges, and reconnect with the community. This session is all about big assumptions and mindset work, and will be a great chance to revisit the frameworks from our coaching cohort and put them into practice. If you've completed a Fort Light cohort, you're invited! RSVP via the link in comments, and I'd love to see you there ✨

💡 5 things I learned from my Fort Light cohort 1️⃣ Big assumptions form our core. We all have big assumptions that affect how we show up at work. Naming and understanding these are foundational to developing as a leader. 2️⃣ Emotions are data 📊 Rather than treating negative emotions as bugaboos, we can approach them with curiosity and ask, what signal is this emotion illuminating for me? 3️⃣ Unclear expectations are premeditated resentments. There's nothing worse than a moving (or invisible!) goal post, so I need to remove any "blur words" from my asks and make sure I am clear. 4️⃣ Start with curiosity 🤔 In feedback conversations, expectation setting meetings, and social contracting, I can examine my judgements and leave them at the door. and my personal favorite .... 5️⃣ Hold the lemons 🍋 There's so much power in just giving others space when they are struggling with something. Before I jump into problem solving mode, I can sit with them and "hold the lemons" before rushing to "make lemonade." So incredibly grateful to Annie Riley and the Fort Light team for running such an excellent cohort. I'm excited to continue learning in the next 10 weeks and applying these tactics at work!

🌉 I'm super happy to be back in SF this week (where it's over 40 degrees - hallelujah!) and am hosting a Fort Light "Leadership Lessons" gathering this Thursday, Feb 13th. We have an awesome crew assembled, and a few spots remain for high-potential, non-founder startup leaders who are excited about learning, growing, and connecting with peers and mentors from different companies. If this sounds interesting for yourself or a rising star leader on your team, reach out and we'll share more details! You can DM us, or I'll link the nomination form in the comments. It'll be a fun one -- hope to see you there!

Quick update: Today we're launching the Fort Light newsletter. If you're a startup leader navigating the challenges of building, managing and leading teams, I'd love for you to join me there. The world doesn't need just another newsletter, but I hope this can be a place where non-founder startup leaders can feel understood, supported, and challenged to grow and learn. Personally, my goals are to get better at writing and to share the lessons being discussed behind the closed doors of our group coaching cohorts and community events so we can help more fellow operators. If you have suggestions for topics and questions that we should cover, I'd love to hear them. Excited to connect and learn together in this new way. More soon!

💫 Today (2/4) is the last day to apply for our next Fort Light SF in-person group coaching cohort 🌉 . Startup founders and execs: If you have a high-potential leader on your team, here’s a quick story for you. One week before our most recent NYC cohort, I met an awesome CTO. We chatted, and when I mentioned our program, he immediately thought of a product leader on his team. He sent her the website and said: “This looks like a great fit for you -- I’d love to support you in doing this.” She applied that night. We interviewed the next day. With her manager’s support, she cleared her calendar and joined the cohort, where she gained insights and skills that she brought back into her company immediately. 🔹 Why share this? Because the top concern I hear from high-potential leaders who apply is they're too scared to ask their manager for the time and resources to join. They worry about falling behind in work, and don’t want to be a “squeaky wheel”. But when a founder or exec actively encourages them? That’s when they feel supported to invest in themselves, and their growth accelerates along with their impact at the company. So, if you have a high-performing leader on your team and you want to invest in them, send them this post. See if they’re interested. Even if they don’t join our cohort, the conversation will go a long way. I’ll drop the nomination form and application link in the comments. If you have any questions, let’s chat -- I’d love to add 1-2 more amazing leaders to this small, high-impact group.

Have you ever been reluctant to say no to your team? Maybe you say yes to things you don't *really* want to, or just delay making a decision? You might even have a good reason for this -- because you think saying "no" might squash the team's motivation or cause friction in the relationship? In the latest episode of Best Manager Ever, Amanda Richardson shares why making a quick decision is better than dragging things along, and how delivering a clear "no" is usually the kind choice. This episode shares Amanda's playbook for communication and accountability, along with other leadership lessons from her experience as the CEO of CoderPad and in product leadership roles at HotelTonight, Prezi and more. It's a must listen for any leader, and especially for folks who notice themselves shying away from conflict. 🎧 Check out the episode wherever you get podcasts, and I'll link to it below. We'd love to hear your takeaways, so please reach out or join the conversation in the comments. --- ⭐ Best Manager Ever is a production of Fort Light and Now It's Hear. This conversation with Amanda is the final episode of season 1 (!) -- if you enjoy it, we'd so appreciate you leaving a rating or review on your fav podcast platform or sharing with a friend who could benefit from Amanda's wisdom.

⏰ Tomorrow, 1/22 is the LAST DAY to apply for the next Fort Light virtual cohort! With Fort Light, leaders change their trajectory and access a supportive network of high-performing peers and experienced mentors to help them win, grow, and thrive on the rollercoaster of startup life. Our small group cohorts are a good fit for self-motivated, non-founder startup leaders who want to level up their skills and accelerate their rate of learning. We'll workshop live challenges and learn the interpersonal and self-management skills needed to build strong, winning startup teams across different functions and companies. Most members tell us the program is nothing like they expected -- in the best way possible ;) Submit an application via the link in comments by EOD tomorrow, Jan 22nd to be considered for the cohort starting next week, and DM me with any questions.