If you told me I could only keep one meeting on my calendar — not client calls, not strategy sessions, not all-hands — I’d keep the weekly 1:1.
That might sound underwhelming. The 1:1 doesn’t have the energy of a brainstorm or the urgency of a pipeline review. It’s just thirty minutes, one person, once a week. But I’ve come to believe it’s the single highest-leverage activity available to anyone who manages people. And I didn’t always think this.
How I Used to Do It
For the first year of running PipelineRoad, I didn’t do 1:1s at all. The team was small — just me, Bruno, and a couple of contractors — and we talked constantly. Slack messages, quick calls, async updates. I figured the information was flowing. Why add another meeting?
The answer became obvious around month fourteen, when Alfredo told me — during his notice period at his previous role, before he’d even officially joined us — that he’d almost not taken the job because he wasn’t sure I valued his strategic thinking. He thought I saw him as an executor.
That floored me. I thought of Alfredo as one of the most strategic people I knew. I’d told other people that. I just hadn’t told him. Not directly. Not in a way that landed.
A ten-minute conversation could have prevented weeks of uncertainty on his end. That was the moment I started taking 1:1s seriously.
The Format I’ve Landed On
I’ve tried a lot of 1:1 structures. Fully agenda-driven. Completely open-ended. Alternating between personal and professional topics. Using templates. Using nothing.
Here’s where I’ve landed, and it’s simple enough that it actually happens consistently.
Their agenda first. The first half of every 1:1 belongs to the other person. Whatever they want to talk about — a blocker, an idea, a frustration, career stuff, nothing at all. If they show up and say “I don’t have anything this week,” I’ll ask a question or two, but I don’t fill the space with my agenda. Their silence is data too.
My observations second. The back half is where I share what I’ve noticed. Not a performance review. More like: “I saw how you handled the Prodeal revision this week — the way you pushed back on scope was exactly right.” Or: “I noticed the CabFare deliverable was late. Walk me through what happened.” Specific. Recent. Tied to something real.
One forward-looking question. I always end with some version of: “What’s one thing I can do to make next week better for you?” The answers are usually small and practical. Move a deadline. Clarify a priority. Make an introduction. Sometimes the answer is “nothing, we’re good.” That’s fine too.
The whole thing takes thirty minutes. Sometimes twenty. Rarely more than forty.
What 1:1s Actually Prevent
The biggest value of a consistent 1:1 isn’t what happens in the meeting. It’s what doesn’t happen outside of it.
Problems compound when they’re not discussed. A small misalignment about priorities becomes a missed deadline becomes a frustrated team member becomes a resignation. That chain takes weeks to play out, but it starts with a gap that a five-minute conversation could have closed.
I’ve had team members bring up concerns in 1:1s that they never would have raised in a group setting. Andre once told me he was feeling creatively stifled because every brief he received was too prescriptive. He didn’t want to say that in a team meeting because he thought it would sound like he was criticizing the process — a process that Bruno and I had built. In a 1:1, he felt safe enough to say it. We loosened the briefs. His work got better immediately.
Mikael used a 1:1 to tell me he was thinking about going freelance. Not as a threat — as a genuine, vulnerable admission that he was weighing his options. Because he told me early, we had time to restructure his role in a way that addressed what he was missing. If he’d waited until his mind was made up, we would have lost him.
These aren’t dramatic stories. They’re quiet ones. And that’s the point. 1:1s work in the margins. They catch things early. They keep the relationship current.
The Mistakes I See
I talk to a lot of founders and managers, and the 1:1 mistakes are remarkably consistent.
Canceling when things get busy. This is the most common and the most damaging. When you cancel a 1:1 because you have a client fire or a board meeting or you’re just swamped, you send a message: this meeting is optional. This relationship is lower priority than whatever else is happening. Cancel enough times and people stop bringing things to the 1:1 because they’ve learned it’s unreliable.
I’ve missed exactly two 1:1s in the last year, both for genuine emergencies, and I rescheduled within twenty-four hours each time. That consistency is the whole game.
Using it as a status update. If your 1:1 is just a verbal version of a project tracker, you’re wasting the time. Status updates belong in async tools. The 1:1 is for the things that don’t fit in a Slack message — the nuance, the context, the feelings beneath the facts.
Talking more than listening. I have a bad habit of jumping in with solutions before the other person has finished describing the problem. I’ve gotten better at this, but it took conscious effort. The rule I use: don’t offer a solution until you’ve asked at least two follow-up questions. Usually, by the second question, they’ve figured out their own answer, which is better than mine would have been anyway.
Making it evaluative. The 1:1 is not a weekly performance review. The moment people feel like they’re being graded, they stop being honest. I never use words like “feedback” in the meeting itself. I just talk about what I’ve noticed, what’s working, what I’m curious about. The framing matters more than the content.
Why Founders Specifically Should Do This
There’s a particular version of this advice that applies to founders and small-team leaders, which is: nobody else is going to do this for you.
In a larger company, there are layers of management. HR exists. People have peers and mentors and skip-levels. In a team of five or eight or twelve, the founder is often the only person who can provide this kind of consistent, dedicated attention.
And founders are terrible at it. I can say this because I was terrible at it. Founders are wired for external — clients, sales, product, market. The internal stuff — culture, morale, individual development — feels soft and unmeasurable and easy to postpone.
But here’s what I’ve learned: the quality of your team’s output is a direct function of the quality of your relationship with each team member. Not the team as a whole — each individual person. And that relationship is built in the 1:1, week after week, through showing up, listening, and being honest.
The Compound Effect
The thing about 1:1s is that any single meeting is unremarkable. Thirty minutes, a few topics, maybe an insight or two. If you evaluated the ROI of one individual 1:1, you’d probably conclude it wasn’t worth the time.
But fifty 1:1s over a year with the same person? That’s a relationship. That’s a foundation of trust that lets you have hard conversations when you need to. That lets someone tell you they’re struggling before it becomes a crisis. That lets you push someone toward growth they wouldn’t have pursued on their own.
I can draw a straight line from my weekly 1:1s to the stability of our team. We have low turnover. We have high engagement. People tell me things early. When there’s a problem, it surfaces fast. None of that happened because of a clever incentive structure or a generous benefits package. It happened because we talk, consistently, one-on-one, every week.
It’s the least glamorous leadership practice I know. It’s also the most effective.