“I don’t believe in one-on-ones.”
When I heard Airbnb CEO Brian Chesky say that, I immediately leaned in because I have spent years telling leaders almost the opposite.
I believe some of a leader’s strongest moments can happen in a one-on-one.
Historically, we have thought about the one-on-one as a check-in with a direct report: What’s happening? What are you working through? Where are you stuck? What do you need from me? But I have always thought those 20 or 30 minutes could be much more than a status meeting. It is prime time for two people to enter each other’s worlds. The leader gets to understand what the employee is seeing and experiencing, and the employee gets access to how the leader is thinking, what they are noticing, and what they may be seeing in that person’s leadership that the person cannot yet see for themselves.
That is why Chesky’s argument challenged me.
He described the traditional one-on-one as a flawed model and said something that stayed with me: “You become like their therapist.”
Now this gets interesting.
A few years ago, Harvard Business Review published an article called “Helping an Employee in Distress.” The authors, counseling psychologist Kiran Bhatti and Cambridge leadership professor Thomas Roulet, made an argument that initially surprised me. Managers should not become therapists, they said, but they should understand some of the basic practices associated with cognitive behavioral therapy, or CBT.
Think about where leadership has moved.
We are asking managers to understand emotional intelligence, psychological safety, employee well-being, motivation, burnout, anxiety and the behavioral patterns that may affect performance. HBR’s argument wasn’t that managers should diagnose people or provide therapy. In fact, they explicitly warned against that. Their point was that managers are often on the front line. They see changes in behavior. They hear what employees are struggling with. They may be the first person an employee approaches.
So on one hand, we are telling managers: You are not a therapist, but you need greater capacity to understand the human being sitting across from you.
And on the other hand, Chesky is warning: Be careful. Your one-on-one can turn you into the therapist.
I don’t think those ideas necessarily contradict each other.
I think they expose a tension in modern leadership that we don’t talk about enough.
What exactly are we asking managers to hold?
I still want a leader to notice when someone isn’t themselves. I want them to listen. I want them to understand enough about human behavior to recognize when fear, anxiety, confidence or something happening outside of work may be affecting the person sitting across from them. I want enough trust in that relationship for someone to say, “I’m struggling.”
But I also don’t want the leader to become responsible for carrying everything.
And there was another part of Chesky’s argument that took this beyond employee well-being for me.
He questioned what happens when people routinely bring things into a one-on-one that should actually be discussed with the larger group.
That one made me think.
How many leaders leave a team meeting and then spend the next several hours or several days having the real meeting?
One person calls afterward and tells you what they didn’t say in the room. Someone else wants clarification. Another person disagrees with the decision but waited until everyone left to tell you. Someone brings you information that the rest of the team probably needs to know.
Eventually the leader becomes the only person holding all of the pieces.
And now we aren’t talking about whether one-on-ones are good or bad anymore.
We are talking about how information moves through an organization. We are talking about trust. We are talking about decision-making, ownership, voice, boundaries and whether the people sitting around the leadership table are actually operating as a team.
I still believe in the one-on-one.
I believe there are conversations that should happen privately. I believe there are moments when a leader needs to close the laptop, forget the agenda and simply ask, “How are you doing?” I believe there are things an employee may need to tell a leader that don’t belong in a group meeting.
But Chesky made me question something I hadn’t questioned enough before:
What is happening in our one-on-ones that shouldn’t be happening there?
Maybe something belongs with the entire leadership team. Maybe something belongs with HR. Maybe something belongs with a mental-health professional. Maybe something belongs with the employee to work through and own. And maybe something is being whispered privately because the organization has not created an environment where people feel they can say what actually needs to be said when everyone is in the room.
That last one should get our attention.
So I’m not ready to give up the one-on-one.
But I am ready to ask a harder question about it:
After your leadership meeting ends, how much of the real meeting happens afterward?
If the answer is “a lot,” the problem may not be your one-on-ones.
It may be telling you something about your organization.