The alumni mindset
Issue 281: The long game of team building
The word alumni is most affiliated with the collegiate system. University alumni groups connect students who matriculated many years apart—people who never overlapped, yet share a common thread: memories, values, and culture. The concept applies well to professional alumni networks as well.
Over the years, alumni groups have formed in technology companies, too. They are the whisper networks where former employees stay connected to help each other out—whether through referrals, co-investing, or something else entirely. A former colleague texts you about a role before it’s posted. Someone gives you a heads-up that a company isn’t what it seems. An old teammate asks if you want in on a deal. These moments don’t come from LinkedIn—they come from trust built over years.
When I build teams, I have one simple goal: become a thriving alumni group. A network of talent often takes care of everything else when it comes to goals and desired successes. Why? Because where you choose to be an alum has a lasting impact. It shapes the legacy you leave behind and cannot be unwritten. It’s an asset of social capital you can deploy for yourself and others. And it builds the enduring relationship graph you want.
Impact beyond tenure
When you leave a company, it might feel like the end. In reality, it’s another chapter of a different relationship. Saying farewell can be complex, and there are certainly instances where being a thriving alum isn’t important to you. However, I believe many tenures continue in other ways. Whether you have a stake in the company (figuratively or literally), your time there will forever be a chapter in your career. You don’t have to be the one on Wall Street striking the ticker bell on IPO day to say, “I contributed to this.”
You can have a huge impact as an alum. I’ve hopped on dozens of calls with people considering Replit and Webflow. Even though I’m no longer at either company, I’m a big believer in the mission, know many wonderful people still there, and am happy to share my perspective with people who are discerning.
But it goes beyond reference calls. I’ve written recommendations that helped former teammates land roles. I’ve made introductions that turned into hires or partnerships. I’ve been in conversations where someone questioned a company’s direction, and I could offer context that changed their view. Sometimes the impact is simply defending the work you did together when others weren’t in the room.
Shared familiarity
Alumni groups are built on shared familiarity. In work and life, there’s a benefit to having people who share experiences like yours. They’re not identical to you, but immediately relatable. For a leader, this might mean bringing in people you’ve worked with before. The goal isn’t to be exclusive or assume the old playbook works—but there are known patterns that accelerate the work.
I’ve had designers I’ve worked with at two different companies. They hit the ground running, knowing what I expect. More importantly, they integrate with the rest of the team fluidly. I’ve also been on the receiving end: when I was at Webflow, there was a huge concentration of Airbnb, Slack, and Dropbox alumni who joined. The Airbnb brought an approach to product storytelling. From the Slack alumni, I absorbed how they thought about platform ecosystems. The Dropbox folks brought rigor to design systems and craft. I never worked at those companies, but I learned from their playbooks through the people who lived them.
Familiarity can become insularity. If you only hire people you’ve worked with, you risk groupthink and blind spots. That’s not the goal of the alumni network. It’s to blend known patterns with fresh perspectives. The best teams I’ve built had a mix of familiar faces and people who challenged how we’d always done things.
Making time
Relationships need tending. As you build them, you can deploy them for good. Over the break, I had the opportunity to catch up with one of my first managers from 20 years ago. We had coffee at the Suncadia Resort in Cle Elum and reconnected. Two decades ago, she was investing in me when I had nothing to offer in return. Now I finally can. We discussed what she’s working on, I made a couple of introductions, and she gave me advice on something I’d been mulling over. The ledger doesn’t matter anymore—it just feels like how it should work.
People often ask me, “How do you have time to stay connected with your network?” The truth is, I don’t have time—I make time to nurture it. Find small pockets. At Atlassian, people often schedule 15-minute meetings. You can’t always afford 30-minute blocks, but 15 minutes isn’t as obtrusive. Take a moment to make a quick call to catch up.
Last month, I had a 15-minute call with a former report. She was weighing two job offers and wanted a gut check. We discussed the trade-offs, I shared my knowledge about one of the companies, and she made her decision. It was a 15-minute call to catch up and assist her.
Recap
Building a thriving alumni group is an ongoing practice, not a one-time initiative. It takes years, if not decades, to get right. One of the joys of my current role is working with alumni not only from my own tenures (Webflow and Replit) but also from networks at Microsoft, Meta, and Dropbox (again!).
Two things to consider: if you’re on a team right now, look around—these are your future alumni. And if you haven’t reached out to a former colleague in a while, send them a note. You don’t need a reason. That’s the whole point.
Hyperlinks + notes
A Forty-Year Career by Will Larson — on how investing in people compounds over a long career
How Will You Measure Your Life? by Clay Christensen — on choosing the right yardstick for success
‘A new era of software development’: Claude Code has Seattle engineers buzzing as AI coding hits new phase — A great event hosted by my friend Lucas Dickey. It’s exciting to see this energy back in Seattle again
Mobile Apps on Replit: Idea to App Store in Minutes — Anyone who has dealt with app store submissions knows what a breakthrough this is; congrats Replit!