Leadership in the Moments That Matter
“Teenagers!”
As if that single word could capture the swirl of thinking, behaviour, emotion, and becoming that unfolds in those years.
It can’t, of course. More often, it’s an expression of our own frustration—a signal about ourselves, not them. Maybe we’re starting with the wrong frame entirely.
What if, instead of trying to get them to understand what we’re saying—asking, demanding, explaining—we did the opposite?
Perhaps we have the jobs backwards.
Maybe we’ve got the jobs backwards.
We assume it’s their role to understand our world: our rules, our urgency, our perspective. But what if our real work is not getting them to understand us, but committing to understand them?
How might we respond, lead, or parent differently if we chose that frame?
Crucial Connections
A few years ago, a friend and client was offered the chance to lead a multi-hundred-million-dollar transformation project. She would have been a remarkable leader for that change, but she declined. Her reason has stayed with me ever since:
“This is an important time. If I lose connection with my daughters now, I may not have it when we need it most in the coming years.”
If we can’t connect when life is easy—over dishes, messy bedrooms, Nerf darts, homework—how can we hope to connect when it gets harder? When bullying, relationships, money, work, and the deeper questions of identity come forward?
The short answer: we can’t. Not for lack of effort, but for missed opportunities to build and sustain connection along the way.
Keep What’s Easy, Easy—Even When It Feels Hard
The easy moments must be kept easy.
The surest way I know is to replace “you need to understand me” with “help me understand you.”
That’s the job: to help them help us understand, not the other way around.
Of course, there’s bedtime, brushing teeth, eating vegetables (or anything at all), doing homework, getting out the door for activities. But what’s really going on with them that makes all this feel hard? Only they can answer that question.
And I’m pretty sure this frame works at work, too.
Don’t Make Them Go Away Faster
A woman working at a client’s customer service counter was raising her voice with someone who clearly didn’t speak much English. After the customer left, a coworker tried to help:
> “You know that when someone doesn’t speak English, talking louder doesn’t help them understand.”
Her reply:
> “I know, but it makes them go away faster!”
Communication and Relationship Are Primary
The task can wait.
First, connect. Ask how someone’s family is doing. Share a story about an upcoming surprise birthday, or a kid’s recovery, or last night’s game. The work goes better when the relationships work.
It’s worth two minutes to lean in, to listen, to understand—when things are easy.
Because when things get hard—a project goes sideways, tech fails, revenue drops, stress rises—it’s too late to connect. The small opportunities we’ve either taken or missed will come back to help, or haunt.
It’s the same as kids grow up, experience big emotional states, and stake their independence. That independence will serve them well, even if it feels hard for us in the moment.
There’s a deeper leadership lesson here:
Connection is the work—at home, at work, wherever humans gather.
When we attend to the small moments, we build the capacity for the hard ones.
– Gerrett
This was originally published on Substack in my Human Systems Playground. But I’ve decided to bring all my writing home here.
