5. One-on-Ones: How to Prevent Blowups From Happening

One-on-ones are regularly occurring meetings between a manager and a subordinate that happen at consistently-scheduled intervals. They are the last technique we’ll explore in the Starter Manager Guide.

Before we continue, I’d like to deal with the elephant in the room: as far as management techniques go, one-on-ones are a bit unusual.

Outside of the tech industry, a manager may go through their entire career and never once have to do a one-on-one. And it is obvious why this is the case if you spend a bit of time to think about it: a manager has to do delegation and training, may find value in prioritisation, and will definitely deal with performance reviews. They also do a dozen other things that are commonly associated with management: for instance, running meetings, synchronising functions across teams, setting targets, and recruiting new members. But one-on-ones are not a natural activity; left to themselves, most managers won’t think of doing an hour-long meeting with each member of their team at regularly spaced intervals.

So why am I including it in this guide?

The answer is that one-on-ones are a powerful tool that enables you to catch problems before they happen.

Most guides about one-on-ones don’t state this outright. They say that one-on-ones are ‘an important tool for information architecture’, or that ‘one-on-ones build trust and engagement between a leader and their team’ … or they show you all the big, successful companies that practice one-on-ones to try and convince you that you should start doing them.

All of these reasons are true and good (well, except for the last one), but they fail to communicate a sense of critical urgency. If you are a manager in a startup, you’re probably already very busy. Why in the world would you start doing a new activity that will burn up so much of your time?

The answer is simple: done right, one-on-ones are a tool that will allow you to prevent problems from happening to your team. With one-on-ones, you won’t be caught by surprise when a subordinate hands in their resignation. You are alerted when a potential problem might derail your team’s work months in advance. And you will find yourself capable of motivating your subordinates, because you’d have taken the time — during your one-on-ones! — to get to know them as people.

These benefits justify the huge time costs.

It is often said that good managers will — paradoxically — give you the idea that they aren’t doing much. The reason this is the case is because they’ve spent all their time preventing the alternate futures in which problems blow up and work emergencies cause people to work late into the night.

One-on-ones are a big part of how good managers make this happen.

A Short History of the One-on-One

I believe strongly in reducing management techniques to first principles, so that you may understand how to apply them to your unique situation. This is particularly important in startups, because successful startups change as they grow. To do this, we need to take a short detour to the origins of the one-on-one.

The one-on-one meeting was created at Intel, and popularised by its onetime chairman and CEO Andy Grove.  Grove defined the one-on-one meeting as follows:

At Intel, a one-on-one is a meeting between a supervisor and a subordinate, and it is the principal way their business relationship is maintained. Its main purpose is the mutual teaching and exchange of information. By talking about specific problems and situations, the supervisor teaches the subordinate his skills and know-how, and suggests ways to approach things. At the same time, the subordinate provides the supervisor with detailed information about what he is doing and what he is concerned about.

Grove argued that the one-on-one was a core management tool for managers at Intel. My experience adopting Grove's one-on-one style has confirmed nearly everything he says about the tool; it really is as useful as he says it is. Today, the one-on-one meeting is standard practice amongst tech companies like Google and Facebook. But it is applicable outside the tech industry, as Grove originally suggested, and as I will soon argue.

I've given some thought over the past couple of years as to why the one-on-one meeting has been so effective. My current conclusion is that it is effective because it amplifies the two levers a manager has for influencing people: motivation and training.

Objections to the One-on-One

“But wait!” I hear you cry, “Why is it necessary to have one-on-one meetings with my subordinates, when I already see them every day?”

The answer is that the form of the one-on-one allows for a different function to emerge. Interactions with your subordinates are influenced by the setting in which the interaction occurs. The kinds of information you exchange in a staff meeting or in a problem-solving meeting are very different from the less formal work environment of the one-on-one.

The one-on-one, then, serves as an important channel for information gathering and building trust with your subordinates. It’s surprising how often information falls through the cracks during daily work, and how slow it is to build trust via daily execution. The one-on-one exists to service both.

I’ll give you an example: a few years ago, I was working closely with a team of engineers on a project that was due for deployment after the Chinese New Year. When I say ‘closely’ here, I mean that I was also an individual contributor on the project, in addition to being manager; I was meeting together, programming alongside, and coordinating with my team for close to 2 months. The project was at risk of being late, so I skipped doing my one-on-ones for those 2 months, reasoning that my time was better spent programming.

I eventually decided to have a single round of one-on-ones with my team before the Chinese New Year holidays. And I learnt something shocking: we were at risk of messing up the deployment, due to the differences in holiday lengths between Singapore and Vietnam!

What had happened was this: in Vietnam, the holidays for the new year were a week long. The holidays in Singapore, in contrast, lasted only two days. It was common for employees in Vietnam to extend their new year vacations up to two weeks, due to family obligations — which was what the most senior engineer on this project had decided to do. That meant that he wouldn’t be around for the project deployment. It also meant that there would be nobody else who could support the project during the deployment —  few other people understood the project as well as he did.

It turned out that a few of my subordinates knew this was a risk, but the hustle and bustle of day-to-day execution prevented them from voicing their concerns. Only in the space of the one-on-one meeting did I hear about these worries, when we could take a step back to discuss the overall situation. What was even more remarkable was that I had been heavily involved in this project — and saw everyone on a daily basis! Yet, despite my closeness to the project (or perhaps because of it) I had completely missed this crucial bit of information.

Shortly after this event I reassigned members of my team to prevent our deployment from turning into a real problem. But all of this could have been avoided had I done my one-on-ones. It would have given me the information necessary to plan for this very situation weeks in advance, causing no disruption to our team. I learnt an important lesson from this: when a manager skips her one-on-ones, eventually, she is the one who pays.

The Principles of a One-on-One

Before I provide a generic template for a one-on-one, I want to talk about the principles that underlie this technique. This is because the ideal structure is whatever works for you, in your specific industry.

The principles behind a one-on-one meeting are simple. First, the main goal of the meeting is information transfer.

As a manager, your goal is to pick up information on problems in your organisation today, as well as information that signals what might be a problem tomorrow. This implies that you should leave a good part of the meeting open-ended. Make sure, while you are on ‘information exchange mode’, that your subordinate speaks more than you do — at least 70% of the time. How you do this is simple: focus your attention to asking questions more than speaking your mind. Take notes on what your subordinate says.

Very often, a subordinate will say something that is indicative of a problem, or is interesting information to you, without knowing that it is valuable. This is because you as manager will have more organisational context than she does. Your job, then, is to watch out for these signals and dig deeper in order to properly evaluate such new information.

What does the subordinate get out of information exchange? The answer is a shared information and cultural base. A subordinate often has questions about the bigger picture: for instance, she might have questions about the company’s history, or about its current competitive situation, or perhaps your leadership’s future direction. You, in turn, can communicate little tidbits that in aggregate make up the backbone of your company’s culture.

If you find that your subordinate isn’t very curious — feel free to offer broader, contextual information yourself. This helps to put their work in context, and informs them of the broader direction they are contributing to.

(No surprise, then, that the one-on-one is one of the most effective mediums through which company culture is spread.)

The second principle regarding one-on-ones is that it serves to build context and trust between manager and subordinate. Your subordinate is more than her work; the one-on-one is the medium through which you may learn more about her person — her hopes, dreams, and fears. The one-on-one is also an opportunity to share with her some of the challenges you face as her manager, with regard to the broader organisation. This sharing provides the foundation for trust during your team’s daily execution.

The third principle regarding one-on-ones  is that the meeting should be regularly scheduled. Set aside a recurring calendar event, and stick to it.

Regularity is powerful! If your subordinate knows that one-on-ones happen like clockwork every month, she will have a natural checkpoint to raise issues or fears she has. Otherwise, you’ll find that your subordinates will keep silent on burning issues for longer than you expect, as it’ll take them more energy to schedule a meeting or to bring it up in your erratic one-on-one schedule.

How often should you run your one-on-ones?

Companies like Google have one-on-ones every two weeks. I ran my one-on-ones once every month. Grove recommends that managers in Intel schedule their one-on-ones according to the overall task-relevant maturity of the subordinate — inexperienced subordinates warrant more frequent one-on-ones, while more experienced subordinates could be met with once every quarter. In order to prevent meetings from being skipped, Grove recommends scheduling the date and time of the next one-on-one at the end of the current one. That way, any interruptions such as vacations and crunch periods would be taken into account. These are all worthy options, but the point is that you should figure out what works for you.

How do you do this? This is simple: adjust according to the number of nasty surprises that occur! If you find that too many work emergencies continue to occur — that is, problems where you could have prevented had you done a timely one-on-one — then increase the frequency of your practice. You want to find a sweet spot that alerts you to just the right amount of potential blow-ups that matches the natural rhythms of your company and industry.

How long should each one-on-one meeting be? Because of their nature, and the potential to touch on deep, important issues, I am convinced that one-on-ones should be at least an hour long to be effective. But that said, my friends in larger tech companies report good results from doing one-on-ones for 30 minutes per session once every two weeks (essentially doubling the frequency and halving the length). The right answer here is — again! — to try it out yourself and see which fits your context best.

Last, but not least, who should prepare for the one-on-ones? Regardless of whether you do an hour every month, or 30 minutes every two weeks, one-on-ones will take up a lot of your time! If you have seven subordinates, this takes up at least seven hours of your time per month!

This is why the one-on-one should be the subordinate’s meeting. The subordinate should prepare the agenda for each one-on-one, and the manager should merely send a reminder to remind the subordinate to prepare for their meeting before it happens.

This lightens the load on the manager considerably.

Doing the One-on-One

By now I've hopefully convinced you that one-on-one meetings are an indispensable tool in a manager's toolbox.

I personally believe that every manager, regardless of industry, should do one-on-one meetings on a regular basis at a frequency that fits their specific company. The benefits are too great to ignore. But if I've failed to convince you that this is indispensable, then I hope I've at least convinced you that this is worth trying.

In this section, I’ll cover how I do my one-on-ones, segue into a general one-on-one structure, and finally spend some time talking about how to start doing one-on-ones if you work in a company that hasn’t done them before.

How I do my One-on-Ones

At the start of every month, I would schedule one-on-one meetings with everyone on my team. These are usually Google calendar invites, sent after quickly chat with them.

We would walk out to a nearby cafe, and I would buy coffee for both of us. The location was chosen to take us out of the environment of the office; and my buying coffee set the tone that this was a more informal meeting.

Then, the content:

  1. We would start with information exchange, a free-flow segment where I would open with “so how was your previous month?”. We would then segue to his opinions on his current work, on what was happening in the company, for his worries, achievements, and fears in the past month. I would note whatever he said that seemed interesting (or indicative of potential problems), and I would answer any questions he had about the company at large. Occasionally, I would share some information about the company's broader direction or coming challenges, if there were any that might affect him. This segment would last roughly a third of our allotted time.
  2. I would spend the next third of our time getting to know him as a person. This involved asking about his background, his hobbies, his family, his life philosophy and whatever else we chanced to talk about. Occasionally I would have subordinates who had similar interests (board games, programming languages, Judo), and we would talk about those. If my subordinate was reluctant to open up, I would open up to him on my personal background, or the current challenges I faced in our company.
  3. The last third of the one-on-one would be spent on his professional development. I would discuss what I thought he did particularly well the previous month, as well as provide feedback for the work that I thought was done badly. Finally, we would discuss what skills he wanted to learn in the coming month, and I would note down our discussion for follow-up. Sometimes, when he didn't have a good idea of what to learn next, I would offer a particular challenge that I knew would be coming up, or I would nudge him to focus on something he had not done badly in in the past. I would explain to him why I thought the skill was valuable, and how it would help him in his broader career outside of our current company.

There are a couple of things I would like to draw your attention to.

My structure is deeply tied to my personal preferences. I was and am willing to criticise my friends, so I had no problems making friends with my subordinates. This is a personal management style, and it might not work for you. If it doesn't, it wouldn’t do to make friends with your subordinates. Instead, experiment to find your own ideal management style; the goal here is to achieve trust, regardless of friendship.

Second, I made notes throughout each one-on-one meeting, and filed those notes for reference later. My notes served as a mandatory tool for keeping track of follow-ups actions or problems. Taking notes is logical: after all, when you discover potential problems, you should write these things down for your attention later; whatever you do, don’t trust your memory!

Third and last, I should note that not all jobs and not all companies allow the manager to take charge of her subordinates's career growth. If you do not have the luxury of taking charge of your subordinate’s growth, you should focus on the core of one-on-ones: that is, the two-way exchange of information, as well as building trust by getting to know your subordinates.

An alternative format

This was a format that worked for me, due to the specific nature of my company. Is there a more generic format to follow? Indeed there is; the best generic one-on-one structure I’ve found has the following shape:

  1. First third: the subordinate’s time — whatever she wants to talk about.
  2. Second third: the manager’s time — task-relevant feedback, or broader work-related information you’d like to share.
  3. Third third: career development — the manager may impart some relevant career advice, or there could be a broad-ranging discussion about the company or industry.

What is important when you implement your one-on-ones is that you adhere to the principles behind them. Remember that the one-on-one is not a status update! Your one-on-one meetings are supposed to be an unfiltered, free-form exchange of information. If in doubt, ensure that you speak for less than 30% of the time.  If your subordinate is overly quiet, it is your job to ask questions.

How to start doing one-on-ones

To start doing one-on-ones, I teach all my managers to do the same thing.

First, contact your subordinate and schedule a slot with her for an hour in the near future. You don't have to explain everything at this point, you may simply say something like “Hey Jane, would you be free for an hour next week? I'd like to schedule a one-on-one meeting with you. It’s something I'm doing with the rest of the team as well, and I would like it to be a regular thing. We'll be talking about work in general, the problems you face as you're doing your work, and what I may do to help you do your job better.”

This opening is short, sweet, and provides just enough context to explain why the one-on-one might be useful to your subordinate. It also reassures her that this is not a meeting to discuss problems with her performance (which is scary!) but a regular thing that will happen with the rest of the team.

During the first one-on-one, open the session with an explanation of your structure. Explain that it would be done regularly (whatever interval that works for you), that it would be at least an hour each time, and then explain the structure you have decided on. Be sure to explain the benefits of the structure to both of you — that is, explain how the one-on-one will help both you and her do your jobs better. That way, your subordinate will not see the one-on-one meeting as a waste of her time.

The success or failure of a one-on-one depends greatly on building trust with your team. Here the trappings of systems fall away and the nature of inter-personal relationships dominate. Your subordinates will remember if you promise something and don't follow through. Your subordinates will stop trusting you if you do not say what you mean, or if you use information they give you in confidence in bad ways. Last, but not least, your subordinates will regard one-on-one meetings as useless wastes of their time if you do not act on the problems they bring to you.

This last bit is important: you don't have to act on every problem a subordinate tells you about during the one-on-one, but you need to have made an effort, or have a good explanation for why you won't act on it.

Last, but not least, I suggest getting coffee. Because coffee makes everything better.

Bonus: The Three Types of One-on-Ones You’ll Experience

I’ve sometimes heard from managers that they don’t really know what to expect from one-on-one meetings, since they’re more personal (and informal!) than they’ve experienced, and they’re less structured than other types of work-oriented meetings.

When you start doing one-on-one meetings, assuming that you do them correctly, you’ll quickly find that there are only three broad types of one-on-ones that you’ll experience. They are:

  1. The normal update (everything is fine!)
  2. The rant (something is up)
  3. The explosion (something has gone really, really wrong)

This section will tell you what to do and what to expect for each, because that will take some of the fear out of doing your one-on-ones. (Hat tip to Rands, who came up with these three categories in his seminal blog post).

The normal update

The normal update is by far the most common one-on-one you’ll experience. We’ve already covered the principles for doing a normal update earlier in this chapter, so I won’t repeat them here.

As a reminder, however, the goal is to gain information — which means listening carefully and probing widely! This means you should be asking questions, and letting your subordinate speak at least 70% of the time.

The rant

The rant is when your subordinate needs to vent about something that sucks. It could be that Joe from customer support is incompetent and should be fired. Or maybe the new hire is making deploys 10x harder.  Or maybe the hiring process itself is horribly broken.

Your subordinate is ranting because she feels deep pain, and that pain is coming to a head during your one-on-one.  Your job during the rant is simple: listen.  It’s tempting to jump in with a solution. It’s especially tempting to butt in when the cause of your subordinate’s angst is a misalignment, that is, a misunderstanding that happened weeks or months in the past. “I’ll just jump right in, and set her straight, and it’ll all be fine!”

Right? Wrong.

The rant is an emotional response to a problem. The problem itself isn’t the issue; the issue is the emotions that have pent up in your subordinate. Your job as a good manager is to let her vent it all out.

Two techniques come in handy here. I first came across them in Chris Voss’s Never Split The Difference, and they’ve both been really useful. The first technique is called the mirror. When your subordinate is ranting, keep her going by repeating what she is saying back to her in the form of a question. For instance, if she says “I can’t stand Andy, he’s full of shit and he takes up so much of our time during staff meetings!” You say, in a non-judgmental tone: “Takes up so much of our time?”

(This sounds a bit stupid in writing, but it really works. If you don’t believe me, you should try it the next time you’re talking to a person who’s passionately going on about something. They won’t even notice that you’re parroting them.)

This helps both her, and you. By repeating her exact words back to her, you let her know that you are actively listening. This allows her to continue her rant, which is good! Secondly, by picking which words to repeat, you are able to drill deep into the source of your subordinate’s frustrations — without reacting to the emotional content of the rant. You’ll want to know: how long has this problem been an issue? How bad is it? Is this a process problem, or a miscommunication problem? Is your subordinate the only person who shares this opinion?

The second technique is the ‘label their pain’ technique. As your subordinate is ranting, you label their emotions back to them. For instance, to play off the earlier example with ‘full-of-shit Andy’, a response could be: “Oh. Wow. It seems you’ve been feeling this way for some time.”

As with all inter-personal interactions, how you say this matters just as much as the content. You should say this slowly and calmly, and with sincerity. Your subordinate is lashing out in emotion. The goal here is to show that you care, and that you are listening intently by labelling the content of their pain.

What does this accomplish? ‘Labelling their pain’ helps defuse the emotional anger that drives some of this pent up anger. People rant because they want to be heard. Labelling their pain — actively and repeatedly! — helps tell them that you hear them loud and clear.

It’s important to note that you shouldn’t be faking this at any point. You really do need to care, and you really do need to put yourself in your subordinate’s shoes for this to work.  A short, demonstrative snippet:

Her: “I can’t stand Andy, he’s full of shit and he takes up so much of our time during staff meetings!”

Me: “Oh. Wow. From the way you’re saying that, it seems that your anger runs quite deep on this. What’s up?”

Her: “I have half a dozen tasks to finish this week, and the bloody staff meeting dragged on for 2 hours on Monday. This didn’t use to happen until Andy got here. Someone should just tell him to shut up!”

Me: “You must be frustrated that the staff meeting is eating into your development time. Your deadlines haven’t moved, right?”

Her: “Yes! Which is so ridiculous! And …”

This rant continues for some time, but you can see how a combination of the two techniques might allow us to make progress. Use mirroring to dig deeper, and use empathetic labelling of her pain to help her to vent her frustration. Only when her emotions are fully vented can we begin to deal with solutions for the cause of the rant.

The Explosion

The explosion is incredibly, incredibly rare. In the past three years, I’ve only experienced it once, and it came during a period of high stress, as a direct result of a monumental mistake that management made. The explosion always starts as a rant. The same rules at the beginning of a rant will apply — but you’ll know things are different if the rant doesn’t conclude.

There are two types of rant endings: the first where the rant ends once the emotions are all vented and your subordinate is satisfied (no solutions needed!) and the second where the rant ends and you can rationally discuss solutions to the problem. Rants tend to go in circles, until the emotions are all vented. Explosions don’t — they become attacks.

You know how in a hurricane, winds start building slowly before they whip up cars, and houses, and trees and glass? Well, something similar happens with an explosion. Your subordinate begins the meeting with a rant in order to build herself up to something explosive. You’ll know something is up when there’s an acceleration to the vitriol.

What you have to do in this situation is simple: Don’t. Make. Things. Worse.

Getting angry makes things worse. Replying to the content of your subordinate’s anger makes things worse. If your subordinate attacks you personally, don’t react to it. Just keep mirroring, and labelling their pain, and listening. If you’re unsure how you’d react, keep silent, but show that you are taking it all in.

At the end of the disaster, thank your subordinate for being frank with you. It goes without saying that a disaster will take longer than a rant. If the attack portion of the disaster has ended, my recommendation is to step away from the meeting and meet again after some time has passed, so that cooler heads may prevail. You may discuss solutions then. But no sooner.

The thing you should understand is that the disaster has happened for a reason: some series of mistakes has driven your subordinate up to the edge, and exploding at you is the only solution they can think of to make things change. It is an action of last resort — but this last fact is a good thing. It means they still care.

In a well managed organisation, you’re not going to experience the explosion as much. But if you do receive it, it’s better to have the explosion than to have your subordinate simmer in anger.

Keep that in mind, but remember: explosions are really, really rare. Rants and normal updates will make up more than 99% of your weekly one-on-ones. There’s nothing to be afraid of when it comes to doing one-on-ones — it’s merely yet another technique that you may deploy as part of the rhythm of company execution.

Chapter 6: Where To Go From Here →