Don't Skip 1 on 1s

Regular 1:1s are an exercise in banking trust.

I was recently asked for advice about 1:1s:

Sometimes I struggle to fill the time of 1:1s with my direct reports. With some of my reports the conversation flows naturally, or they drive the conversation by talking about what they’re working on or the problems they’re facing, but for other reports the conversations are often full of silence. I’m often waiting for them to say something but they don’t.

Should I be expected to drive the content of these 1:1s? And if they regularly don’t have anything to say, what do you think if I instead made them elective/ad-hoc?

Short answer: Keep regular 1:1s. A weekly 1:1 1 is critical to building trust and context, and elective 1:1s are unlikely to be used until there’s a fire. A regular 1:1 allows you to smell those fires ahead of time, which is a critical part of the job. And yes, you are expected to drive the content in the absence of the other person doing so.

The importance of regularly scheduled 1:1s are rooted in a few lessons:

  1. Regular availability is critical for a healthy management relationship. 2 The best way to understand someone - their context, their motives, their preferences - is to spend consistent time together. The times I’ve felt most frustrated by a manager is when I felt unacknowledged due to a persistent lack of responsiveness. Regularly rescheduling or cancelling 1:1s, regardless of the reason, unavoidably communicates that someone is not a priority. 3 The currency of challenging management conversations is trust, and the backbone of that trust is being available and responsive.
  2. Management calamity often snowballs quickly. A pattern I’ve seen often is that when people are upset about something, they stay quiet until it reaches a breaking point, after which their frustration spirals. It is much harder to bring someone back to a good place post-spiral than pre-spiral.

The currency of trust

While I don’t love characterizing management relationship as transactional, what I mean by “the currency of trust” is that management behaviors either “bank” or “spend” trust. You bank trust when you demonstrate behaviors that show a report you’re in their corner: sponsoring them for an opportunity, helping them navigate a case for promotion, or supporting them through challenging circumstances. You spend trust when you deliver bad news: the constraints of a difficult economic environment during comp time, the need to delegate some unglamorous glue work, or sharing some critical feedback. The good reception of bad news is often predicated on how much the receiver of that news trusts the intentions and character of the deliverer of that news. Regular, good faith 1:1s are an exercise in banking trust.

Don’t offer to cancel

Something I’ve learned not to say to a report: “Hey I don’t have anything to talk about today, are you good to cancel?”

While it’s dependent upon personality, I find that in most cases the power dynamics implicit in reporting structures means that it’s likely a report will say yes to this request, even if they do have something to talk about. Consequently I’ve developed a personal rule to never preemptively offer to cancel a 1:1.

I think the same question in the other direction is fine. And if in the course of conversation we run out of things to talk about and mutually agree to end early, that’s also fine. But I want to leave either situation confident that I’ve given the opportunity for the other person to voice what’s on their mind.

Driving content

While many reports will drive the content of 1:1s without prompting, some don’t. It just happens. And in these cases the responsibility of driving content falls on the manager. Assuming you’re going to manage a variety of personalities across a career, this is a skill worth cultivating.

When conversations go stale in 1:1s, a common reason is that the topics at hand are too limited in scope or time horizon: “the work is chugging along and nothing is wrong right now.” To break from that my strategy is similar to my strategy for conducting interviews: ask a lot of questions. I zoom in: how they feel projects are going, what skills they’re developing, what the pain points are, what could go better, etc. I zoom out: how their work aligns to career goals, feelings about changes in team/company strategy, what their growth areas are, etc. I share my own opinions of things I’m excited about or disappointed by and ask for their takes. And I do my best to actively listen so I can follow up to any responses with new questions.

It can also be helpful to set expectations around 1:1s via a framework of topics. Jean-Michel Lemieux, the ex-CTO of Shopify, shared his framework on Twitter where he splits topics for meeting with his reports into three general categories:

  1. 25% Boss: Keep accountable for goals, quality, and growth
  2. 50% Peer: Bring decisions and get my feedback, let’s brainstorm. I’ll share what I’m up to as well.
  3. 25% Work for you: Given your goals, how can I help you?

I’ve literally pasted the tweeted graphic at the top of 1:1 docs. Not because I expect to follow it to a tee, but because it serves as a reminder to both me and my report about the type of topics we should be bringing to our recurring meeting.


  1. The context of this advice is direct reports, not skip-levels. I’m less prescriptive about skip-levels because I think recurring skip-level 1:1s can become untenable depending on the size of your org and personal bandwidth. If you can’t sustain scheduled skip levels, other patterns like Office Hours, Lean Coffee or org/group/seniority-level meetings can be useful mechanisms to build community and solicit feedback. 

  2. “Regular availability is critical for a healthy management relationship.” 

  3. Conflicts happen, and when they do I make sure to apologize and include a note for the rescheduled event (versus simply rescheduling without context). I think the gesture goes a long way towards acknowledging the two-sided commitment of meeting regularly with someone. 

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