Here are two facts that you probably already know. First: one-on-ones are regularly occurring meetings between a manager and a subordinate, that happen at consistently-scheduled intervals. Second: one-on-ones are an absolute pain to do.
This second fact leads logically from the first. If a typical one-on-one meeting takes 30 minutes every week, or an hour every month, you’re basically spending that amount of time multiplied the number of direct reports you have — for the regular interval that you’ve set! When I ran a twelve person team, I had to spend twelve hours a month doing one-on-ones. That was a lot of hours — and it wasn’t sustainable on top of my normal startup workload.
(I eventually found a manager for half of the team, and turned that manager into my direct report — thus cutting my responsibility down from twelve to eight. But more on that for another day).
The truth is that the pain of doing one-on-ones will persist throughout your entire management career, for as long as you opt to do one-on-ones. Regardless of how small your team is, or how short you arrange your one-on-one meetings to last, you’re going to spend a lot of your time as a manager in these meetings with your subordinates. And there’s simply no way around it! You can’t have a good one-on-one meeting in a short period of time, in the same way that you can’t grow a relationship with a friend over a handful of 30-minute meetings each year.
The answer that some managers have to this quandary is simple: they stop doing one-on-ones. Or do they do them when it’s convenient to do so, and proceed to skip doing them whenever a crunch period occurs.
So it’s worth asking: why is this much pain necessary? If one-on-ones are so time consuming, why do them in the first place?
Five Good Reasons
I’ve read a lot of management articles over the years, and nearly all of them skip past the ‘why’ and jump straight to the ‘how’ when it comes to doing one-on-ones.
But this is odd to me. My experience training new managers suggests that it’s important to spend some time on the why, because one-on-ones are not an obviously necessary thing to do. To put this another way: when training a new manager, it is obvious to them that delegation is important, that training is necessary, and that prioritisation is valuable. These are things that they have to do as a manager anyway, even without being prompted; your training merely serves to teach them better ways of doing things they’re already forced to do.
But if you never teach your managers to do one-on-ones, it is not clear at all that one-on-ones are necessary to the practice of management. Indeed, for most managers in other industries outside tech, one-on-one meetings are rarely — if ever — part of the typical manager’s handbook.
I believe that you should always articulate why doing one-on-one meetings are important, what purpose they serve, and when it is reasonable to stop doing them. Not doing so is stupid: one-on-ones incur such a huge time cost that it’s important to justify their necessity.
So let's look at five major reasons.
1. Prevent Blowups
Preventing blowups are my raison d’etre for doing one-on-ones. It's the first reason I tell my managers when I begin teaching one-on-ones to them; it's also amongst the first things I say when I take a direct report out for our first one-on-one together.
One-on-ones prevent blowups — otherwise known as work emergencies. Blowups affect the entire team. If I stop doing one-on-ones regularly, sooner or later a preventable blowup would occur, and I would have decreased the output of my team.
To understand why this is the case, we need to make a short diversion to the origins — and original intentions — of the one-on-one meeting.
One-on-ones were originally introduced by then-Intel CEO Andy Grove in his book High Output Management — though the practice had probably spread out from Intel to other companies in Silicon Valley during the ’growth phase’ of the semiconductor industry.
In High Output Management, Grove wrote that the ‘one-on-one is a meeting between a supervisor and a subordinate, and it is the principal way their business relationship is maintained’ ... and that the primary purpose of the one-on-one was that of ‘mutual teaching and information exchange’. The subordinate would be able to retrieve context and gain feedback and know-how from their manager, and the manager would be able to retrieve information about what the subordinate is doing, and what they are concerned about.
This all sounds very nice and happy and theoretically useful, so let me sharpen it up for you: think of the last three work emergencies that you had to tend to as a manager in your company. It could be anything: one of your subordinates leaving you, a customer blowing up at a bad deployment, a server going down. In a startup, work emergencies are the name of the game.
Now, think of whether these work emergencies could have been prevented had you gained the appropriate information beforehand. The odds are good that you could have prevented the blowup from happening in at least one of the last three work emergencies this way.
This then implies that a manager should thoughtfully curate the sources of information he or she has — in order to prevent blowups from happening. The one-on-one meeting is a key tool in the pursuit of this goal.
During a one-on-one, your most important task is to listen for potential signals or hints that a problem might lie right across the horizon, all prepped to blow. These signals and hints are often innocent remarks or observations made by your subordinates.
“It’s odd that Jane hasn’t contacted us about the last deployment”, or “I’m feeling nervous about our current client.” may sound like innocent utterances to the external observer, but should read like BIG WARNING SIGNS for the manager to probe further.
Remember, the manager’s job is to increase the output of their team. Letting perfectly preventable blowups happen is one of the things that separates the bad managers from the good ones. The one-on-one remains one of the richest sources of information you have at your disposal; not doing them is to give up a major tool in the effective manager’s toolbox.
2. Build Trust With Your Subordinates
It’s no secret that trust is key to being an effective manager. If your subordinates don’t trust you, or believe that you have their best interests at heart, you’re almost certainly not going to be an effective manager.
The one-on-one is a major avenue with which you can build this trust. It should be no surprise to you that you can’t trust someone without knowing who they are as a person — where they come from, how they see the world, what they have as hopes, dreams and fears. You can’t usually talk about such things in the rush of day-to-day execution, so the one-on-one remains the primary avenue with which to pursue the growth of your relationship to the team.
When I first started doing one-on-ones, I gave myself two objectives for each meeting I held. First: that I would spend 70% of the time listening instead of talking. And second: that I must learn at least one new thing about each subordinate after each one-on-one session.
This rule served me very well: the ’70% listening’ rule taught me tools and techniques for drawing out information and identifying potential blowups, and the ‘learn one new thing’ rule taught me to understand my subordinates as human beings.
You might think that you know your subordinates and teammates because “you see them everyday”. But there’s a difference between ‘working with’ and ‘knowing’, and the one-on-one is how you bridge the gap.
3. Give and Receive Feedback
It took me a long while to realise the importance of this, but giving and receiving feedback is the bedrock through which a manager increases the output of the team. Without the one-on-one, meeting the avenues a manager has to give and receive feedback is limited at best.
Sure, programmers and designers ‘give feedback’ via code reviews and design critiques. If you’re a marketer, you give feedback based on the results of the tail end of a marketing campaign. But these forms of feedback are execution-bound, and laser-focused on the work that’s just wrapped up. They aren’t high-level, and they don’t allow you the space to focus on patterns that may supercharge your subordinates growth.
Here’s an example: say that your subordinate Jane has a habit of misalignment, especially during the requirements-gathering stage of a task. You’ve observed three separate occasions over the past few months where Jane took an existing set of requirements, dove into them without asking for clarification or guidance, and emerged a week later with a slightly-wrong implementation. In all three cases your team had to take a hit on productivity as they worked to fix Jane’s work.
What are you going to do about this? Most managers would give feedback after each incident, and then maybe pull Jane aside and tell her off after the third or fourth time. Jane might take this the wrong way, and learn to resent meetings where her manager — you — pull her out of her work.
The answer to this predicament is the one-on-one meeting. If there was a regularly scheduled meeting where you and Jane may talk, there would be an opportunity for you to establish a regular cadence of feedback and improvement. You would be able to check the bad habit early, and work with Jane over a series of months to gently correct the behaviour.
4. Spread Culture
I won’t spend that much time on this, because I believe that culture is a higher-level management skill. But if you’ve reached the stage where you can start worrying about your team’s culture, the one-on-one meeting will most likely be where you’ll do your heavy-lifting.
Cultural exists primarily in the minds of the individuals that make up a group. If you want to mould culture, you’ll need an avenue for feedback on the actions you take. The one-on-one meeting is — again — the best avenue for such feedback: it allows you to read the efficacy of your cultural efforts through individual conversations with each member of your team.
The point here isn’t that one-on-ones are necessary for retrieving feedback. It is that a regularly scheduled, private meeting between manager and subordinate enables all sorts of opportunities, especially when it’s held at a cadence regular enough to be useful to both.
5. Hold On to Your Subordinates
The last major reason for doing one-on-ones is something I don’t necessarily agree with, but that I’m including because I know managers who believe in this as strongly as you or I might believe in gravity.
The average tenure for a tech industry worker in Silicon Valley has gone down to about a year per role. In Vietnam, where no minimum employment norms exist, the average employment period for a new hire might well be shorter than that.
If you do one-on-ones every month, a hire with average tenure at your startup will only meet you for 12 meetings before leaving. I know managers who believe that this isn’t nearly enough; they switch to 30 minutes every two weeks, or some variation thereof. It is their hope that such attention will compel new hires to stick around for longer.
The key argument is this: a one-on-one builds trust and helps your subordinates with their growth. If you do one-on-ones more frequently, you should be able to help a subordinate with their career goals. One-on-ones are thus seen as the primary means for some managers to increase retention.
I don’t fully agree with this because I think the nature of retention is more complex, and better left to a separate post. But I do believe there is a kernel of truth here. As average company tenure goes down across the industry, you should keep in mind that you have far fewer opportunities for direct connection when it comes to doing one-on-ones.
Each one-on-one becomes more precious, and that’s something we should all pay attention to.
I hope I’ve given you several compelling reasons for doing one-on-ones. I’ve opened this post with the frank assessment that one-on-ones incur a huge time cost, and I admit that there’s not much you can do to reduce that cost.
What I can hope to do, however, is to help you see that there are compelling reasons for incurring these costs. It’s no accident, after all, that a large portion of the tech industry has moved to adopt one-on-ones as a basic management habit. And I’ll wager that any organisation with managers that do one-on-ones will be far more effective than an organisation that doesn’t.