What I Learned About Building High-Connective Experiences For Founders This Past Year
Five things I learned about connection after one year at Hampton.
I’ve been at Hampton for a little over a year. Time flies! I came in with one mandate: own and grow the Core Group experience.
Before I tell you more about that, let me tell you about Hampton and what Core Groups are.
Hampton is a network for high-growth founders. At the heart of the membership is our Core Group product: monthly sessions where 8-10 founders, led by a trained Moderator, come together and work through their biggest professional and personal challenges. It’s a place where a founder can say the things they can’t say to their team, their board, or their spouse: the deal that’s falling apart, the co-founder they need to let go, the fact that they hit the number everyone wanted and still feel imposter syndrome, etc.
Core Groups are a place where founders have conversations they can’t have anywhere else that sharpen every decision they make everywhere else.
Everything I do on a day to day basis is in service of making Core Groups feel safe enough for those conversations to happen.
I’ve spent a good chunk of my life in connective spaces: on retreats, in therapy, in coaching… and I walked into Hampton with strong instincts about what makes connective spaces work. A lot of those instincts were right. Some were incomplete. The gift of this year was that a lot of my underlying instincts hardened into principles I can name, teach, and design around. A connectivity playbook, if you will.
Amongst all these principles, there’s a clear through-line: the fastest way to build a high-connection space is to ask more of people, not less. Commitment is the precursor to everything else. You’ve often got to commit deeply to something uncomfortable to get the real, can’t-find-this-anywhere-else kind of value. As Obama said in his 2014 State of the Union, and an oft-quoted line in my household:
“Nothing in life that’s worth anything is easy.”
So what are my hardened principles for building connective, group experiences?
Connection matters most at moments of inflection.
People crave connection most when they’re standing at a moment of inflection… right when the ground is shifting under them.
For Hampton founders, in business it’s selling the company, fundraising a round, stepping back from the thing you built. In personal life, it’s a move, a marriage, a new baby, a loss. Those are the moments when people go looking for connection beyond the relationships they already have.
It’s why segmenting connective group experiences around a shared inflection point is so powerful and long-lasting.
It’s not just about clearing a bar of accomplishment, or being in the same place at the same time. It’s about catching people in the window where they’re most open, most in flux, most in need of a room that gets it.
When you design for the moment of inflection, the connection almost builds itself. And it’s incredibly sticky.
The more specific and formative that moment is, the stronger the connection, and the more likely it outlasts the moment itself. It’s why people still have a college group chat or why new parent groups are so powerful.
Formative inflection points yield everlasting connection.
The professional and the personal go hand in hand.
Founders come to Hampton for business results, the same way people seek out coaching for support with their professional goals. The difference is mostly scale. In coaching, the goal is usually individual: I want the promotion, the raise, etc. At Hampton, it’s company-wide: sell the business, hire the exec team, 3x the company.
But here’s the mistake I see people make: treating the business goal and the personal one as two separate things. They almost never are.
I’ve seen this a lot in my own coaching work. It’s one of the reasons I start with a very integrated discovery process. I don’t just ask people what their professional goals are. I ask what their personal goals are, because I don’t believe the two can be seen or treated in isolation: If you’re trying to become a Chief Product Officer, what’s happening in your personal life that might block you from getting there?
Underneath the professional hurdle, there’s almost always something more personal. A pattern. A fear. A story someone tells themselves that keeps them from making a clear decision. The professional reason gets them in the door. Yet, the personal work is what actually keeps people coming back. Because when you understand the underlying pattern thats impacting your professional decisions, you can see how it impacts all decisions and behaviors in your life, not just the issues that show up in your work.
Pretending that professional and personal are separate is exactly what keeps people stuck. They are intertwined and they feed information back and forth that’s crucial to grow in both facets of your life.
Go deep first, not last
Hampton Core Groups start by going deep, fast. On day one, before founders know a single thing about each other, we ask them to share their 5% moments: the highest 5% and the lowest 5% of their life. No business, no numbers, nothing performative. We go really deep, really quickly, to unmask the most pivotal parts of their life, because when they do that early, they build trust. Coming from a business frame it feels a little unexpected, and quite uncomfortable. That’s the point. We’d rather push them to say the thing rather than let them perform politeness for six months.
Going deep first is about unmasking. Founders walk in wearing the version of themselves that raised the round and closed the customer, and that version is exactly the one that can’t be helped, because it isn’t allowed to have problems. The whole game is getting the mask off early. Not oversharing, just naming the real thing.
Related reading on unmasking:
Depth isn’t the reward you earn at the end of a relationship. It’s the on-ramp.
Ask people for something real on day one and and you signal that this is a place where real is allowed and necessary for real change. High-growth founders are starving for that. They have plenty of rooms where they can be impressive. They have almost none where they can be honest.
Spoiler alert: It’s not just a founder thing.
Presence is not a nice-to-have. It’s the whole thing.
When I started at Hampton, Core Groups were mostly virtual. We’ve since flipped it: the majority of our Groups now meet in person. That was not a small logistical tweak. It was one of the hardest operational lifts I’ve ever been part of. So why do it?
You cannot manufacture the thing that happens when people are in a room together, phones down.
Think about it: we barely have tech-free spaces anymore, where you sit for an hour, two hours, three hours with no screen at all.
Those in person experiences are the meat. But like a good meal, you need more than a main dish. You need the apps and side dishes: the dinner after, the text thread that lights up at 11pm, to complete the meal.
Think about the strongest groups in your own life. The in person time is important but the connections were strengthened because there was connective tissue between in person time that kept the energy flowing.
Anchor groups on in person connection but don’t discount how important the in-between moments are to strengthen the bonds.
You don’t need answers. You need someone to ask you the right questions.
Someone shares a problem, you want to solve it. You have advice. You may have even lived the exact thing they’re living. But copying and pasting what worked for you onto someone else is, more often than not, the wrong answer.
The people in these rooms are not short on answers. They’re some of the most capable operators alive, drowning in advice. What they’re missing is almost never the answer. It’s the right question.
So we take a no-coaching approach. When a founder brings a hard thing to the group, the move is not to fix it. It’s to ask the question that lets them find their own way through. Advice makes people dependent on you. A good question makes them more capable in the moment and in the future.
I apply the same to my coaching practice. I rarely tell people what to do - in fact, I rarely share my adjacent experiences with clients. I find that the best results come from asking my clients the right questions. Not because I don’t have related experiences, or because I’m trying to gate keep, but because we get to better answers for them when we stay in their world vs. muddling my experiences with theirs.
The highest form of support in a room like this isn’t the smartest thing you can say. It’s the space you hold to ask the right questions.
Stick with questions, always.
Connection is something you can design on purpose, and you do it by asking more of people, not less.
So ask for a lot.
And, guess what, you shall receive long lasting connection.
Cheers to one year 🥂
I’m Jori Bell, VP of Core at Hampton. I’m also a Coach for Product Leaders.