Last week I was in Miami and I met with three people: a former coworker who had recently moved, a past client I’d worked with for years, and a new contact from the Chief of Staff Association. I wasn’t trying to pitch or impress. I just wanted to connect.
All three conversations were worthwhile. Each has the potential to become a real relationship.
But one of them stayed with me.
In that conversation, we didn’t just talk, we shared. Truly personal stories about family dynamics, strained friendships, and the heartbreak of watching people we love make decisions we know aren’t good for them. Real hardship. Honest vulnerability. It wasn’t planned or forced. It just happened. And it required something from me: to show up fully, listen deeply and be completely present.
That’s when I realized something I hadn’t put into words before: presence is what unlocks connection. I didn’t need history or shared work. I needed to show up. And so did they.
That moment sparked the question I’ve been chasing ever since:
What actually makes a relationship real?
Turning Point
For the past few months, I’ve been navigating a thoughtful search looking for the right opportunity to support a bold, visionary principal. The process has been intentional and surprisingly revealing.
Everyone kept saying “leverage your network” or “build relationships.” I knew what they meant but the more I tried, the more awkward it felt. Every conversation started to feel like a sales pitch… and people could smell my desperation. Heck, I could smell it. And let’s be honest, nobody likes that smell.
So I stopped selling. I started focusing on connection instead. And as I paid closer attention, I began to notice a pattern: some conversations felt effortless, energizing and even enriching. Others felt transactional or flat.
And the answer was pretty clear.
The Relationship Equation
A real relationship requires three things:
Miss even one, and you don’t have a relationship. You have something else. A contact, a transaction or a well-intentioned dead end.
Here’s what each part means and how I got there:
Two people.A relationship requires full presence from both people. One person, one focus. It’s not about how many people you know, it’s about showing up fully, with intention, for the one who’s across from you. Quality over quantity. One-sided effort isn’t a relationship, it’s outreach.
Shared values.You don’t need shared thinking. In fact, disagreement can deepen a relationship. But you do need shared values: a relational gravity that holds things together.
My best friend and I don’t share the same political views, but we deeply respect and care for each other’s opinion. She’s changed my mind more than once. Without shared values you start second guessing every interaction. Trust cracks and connections thin.
Mutual desire.This was the piece I hadn’t named before. Desire is what turns a connection into a relationship. It’s what gets both people on the relation-ship (ha) and rowing 🛶 in the same direction.
While planning an event for CREW DC, I worked alongside two incredible women. And while all three of us contributed, the relationships I built with each of them happened one at a time through side conversations, shared ownership and the kind of mutual investment that builds trust. It wasn’t just teamwork. It was a personal buy-in. We each chose to show up not just for the task, but for each other.
That’s mutual desire. It’s the motion in the ship. It’s what turns proximity into partnership.
When to Use the Relationship Equation
This isn’t a framework to apply to every person you meet.
It’s a gut-check for those moments when something feels… off. When you’re not sure what’s missing. When you keep showing up to a connection that never quite clicks. Or when a relationship that once felt strong starts to fade, and you can’t quite name why.
That’s when you ask:
Are we both showing up?
Do we share the same values, even unspoken ones like mutual respect?
Do we both want this connection to continue?
If one of those pieces is missing, that doesn’t mean you have to walk away. But it does explain the friction. It gives you language for what you’re feeling.
The relationship equation helps you pause, reflect, and get clear so you can stop forcing something that isn’t mutual, or deepen something that is.
What If It’s Not Mutual?
If relationships are core to being a great Chief, what happens when you can’t build one? When you try and the other person just doesn’t meet you there?
That’s a hard question. And if you’re anything like me or like most self-aware, high-achieving, relationship-oriented Chiefs (aka, my people!) you’ll probably take that friction personally.
But here’s the truth: it doesn’t mean you’ve failed.
You don’t need a deep relationship with everyone. That’s not realistic or even necessary. You can show up with clarity, respect, and openness. But you can’t force mutual desire. You can't make someone want to be on the ship.
Sometimes, a working connection is enough.
Your job is to make the system work whether through deep trust or graceful distance.
Not every connection becomes a relationship.Not every relationship needs to be deep.And that’s okay.
Your Lever for Effectiveness
Why does of all this matter to a Chief of Staff? Because if there’s one skill that makes or breaks your effectiveness, it’s this:
Your ability to build meaningful relationships across an organization.
Not just with your principal. With department heads, program leads, assistants, client contacts and even skeptics. It’s not just a business advantage, it’s the quiet operating system behind everything you do.
If you’re a Chief taking a closer look at your relationships, ask yourself:
Where am I strong?
Where am I forcing something?
Where might something real be waiting to deepen?
This is just the first piece of the puzzle. The second piece involves strengthening the relationships you’ve got, by understanding…
There are levels to relationships.
There are ways to deepen them faster.
There are things to avoid.
I’ll share those next.