⏱ Read time: 5 minutes
I’ve been having a lot of conversations lately with people considering new opportunities: some job searching, some talking to recruiters, and some just thinking about what they want to do next.
The recurring question we end up talking through is: What’s the best way to think clearly about choosing your next opportunity?
People often start with things like company logo, employer brand, job title, company size or stage, vertical sector, or a specific hot category. (Hello, foundation model companies and AI-native companies.) I’ve considered these lenses too at different points in my career. They matter, but they mostly describe the external shape of an opportunity.
Sometimes there are real constraints: you need the job, compensation matters, family reality matters. I’ve been there.
But I’ve also found that I make better decisions when I start from the inside out — asking what it’ll feel like to do the work, with these people, at this point in my career, and how it might help me learn and grow.
This frame is personal, and meant as an idea starter, not a prescription. It’s just something that has worked well for me.
Here are the three questions I ask and think about:
The Product: Am I excited by what we’re building?
The Team: Do I want to build it with these people?
The Growth: Will this opportunity stretch me or help me grow?
Here’s how I think about each one.
1. The Product: Am I excited by what we’re building?
What are we building, and how interested am I in the idea of working on it every day?
The last thing I want is to work incredibly hard, look up, and realize: “Hey, this thing I’m building is actually not that interesting or meaningful to me.”
I’ve always wanted to feel fired up by the actual product, problem, or mission. How interested would I be day to day? Do I already use it? Would I use it? When I explain it to someone in my family, what’s their reaction? Do they understand why it matters? Would they use it?
As my kids got older, their reactions became an increasingly useful sanity check. It helped me see whether I was living in reality outside the normal tech bubble.
Headspace is a good example. Before I ever had a conversation about working there, I had used the product for years and benefited from it. So when I went through the interview process, I already knew the product from the inside out as a user. I’d seen different versions of it over time. I understood what it did well, where it had evolved, and why it mattered. That made the opportunity feel very real to me. It was something I was genuinely interested in being part of.
2. The Team: Do I want to build ‘the thing’ with these people?
Jeff Weiner has a people framework I’ve always liked: look for people who can dream big, get shit done, and know how to have fun. The best part of that advice is that you have to have all three.
When I’m considering an opportunity, I try to imagine what it would feel like to work with this group day to day on a hard problem. That includes the manager I’d be working with, the cross-functional partners, the people who might report to me, and the broader group around the work. What are they like? How do they think? How do they treat each other? Would I enjoy problem solving with them?
For me, fun shows up here. So does judgment. So do kindness, generosity, commitment, and the basic energy of the group. I’ve had the good fortune to work with outstanding teams at Yahoo, LinkedIn, and Facebook/Meta — people who were extremely talented, kind, committed, and generous. Years later, I’m still close with many of them.
When you work with someone multiple times, across multiple companies or chapters of your career, that usually tells you something. Those are the kinds of people I’m looking for when I evaluate any opportunity.
I do some research, of course. I pay attention during interviews. I listen for how people talk about the work, the team, and the problems they’re trying to solve.
But a lot of this also comes down to feel. Would hard work with these people feel energizing or draining?
3. The Growth: Will this opportunity stretch me or help me grow?
The best opportunities make me better in some meaningful way. That might mean bigger scope, role progression, learning a new domain, helping solve a transformation problem at a company, building a new skill or muscle, or financial upside. But this question also evolves depending on the season of a career.
Sometimes the stretch is about taking on a larger role. Sometimes it is about learning a whole new industry. That happened for me when I joined Headspace and Included Health after years working on information and media products, social, and video experiences. Healthcare was different: complex and new to me in ways that made both opportunities interesting.
Sometimes it can be about joining a company or team that needs to go through a transformation, and asking whether I can help a team make progress there, fix things and improve. Both Headspace and Included Health also fit this lens for me. They were different than working at large internet companies, where operations, give or take, are working pretty well.
Compensation and equity matter for sure. I think about those things and get advice on them when considering new roles. Public company equity, pre-IPO equity, salary, and financial upside are all real inputs. I don’t discount those.
But for me, they usually sit inside the broader question: Will this opportunity help me learn, grow, contribute, and become better than I was before?
Use these as a practical gut check, not a rigid decision matrix.
If you’re looking at opportunities — or even just thinking through what you want to do next — they can help you double check what you’re optimizing for.
The TL;DR: Don’t just ask how the opportunity looks from the outside. Ask what it will ask of you, who you’ll be around, and whether it will help you grow.
As you’re thinking things through, try to answer the three questions honestly. The weakest answer may tell you where to look harder.
👋 Hi, I’m Jeff. I coach senior product leaders through the moments their playbook stops working — drawing on 25+ years building at LinkedIn, Facebook, Headspace, and Included Health. If that’s you or someone you know, ping me.