Startups | 13 min read

How to run 1:1 meetings that work for 2

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As an Engineering Manager it’s not always obvious where to allocate time for maximum impact.

Time spent in 1:1 discussion with my direct reports is the highest leverage time in my calendar and it’s the de-facto place I go to every week to see where I can make a difference. For 30 minutes of time I get the opportunity to amplify the work of somebody on my team by an order of magnitude for a sustained period. Multiply that out by my team size and compound that over 52 to get a feel for the kind of impact effective 1:1’s can have on team success over 12 months.

This week I will spend 35% of my time in 1:1 meetings. When I started allocating this kind of time I was deeply dissatisfied with the return on investment. Sometimes I’d leave happy, only later to discover that my directions weren’t clearly understood. Sometimes I’d forget what I’d said last week. Sometimes I’d spent 30 minutes shooting the shit. Sometimes we’d rehash things discussed in planning. Sometimes we were talking at a time when we really should have been doing.

When two people chat, each person will leave with their own perspective on what that conversation was about.

Over the past few months fueled by ideas from people like Andy Grove and Jeff Caselden I’ve been tinkering to try improve the impact of my 1:1 time. Here are some things I’ve found to be important.

Know why you’re meeting

You need buy in from your report that the 1:1 meeting will not only be a valuable use of her time but an essential component to her success at your company. You should spend at least the first couple of 1:1 sessions imparting your philosophy. I find it useful to appeal to the self interest of the team member at first. Let them know what you can offer them directly. Typically this means career development, growth opportunities and guidance. The goal here is to get your team member to take the 1:1 slot seriously – and not consider it an interruption to otherwise more important things. You might need to repeat this exercise many times.

If you’re a brand new manager, on a new team, or new to the company it might be worth inverting this completely to start. Let them know how they can help you so that you can eventually help them.

Clarify ownership

Ownership of 1:1s and associated work is a little tricky. One non-negotiable is that the time belongs first and foremost to the person you’re managing. Regardless of what you want to talk about, always give your report first choice on the agenda. This means they should turn up with an agenda – I think that’s also important. Chatting for three minutes about what to chat about is a really good use of the first three minutes.

I personally prefer to own the scheduling and notes by default. This can be flexible though, as long as things are clear. As with much management work, identifying ownership and expectations up front is a useful exercise in avoiding misspent time.

Scope the meeting

You want to be really open initially, so avoid explicit scoping in the first few meetings. 1:1s are the right place to talk about career goals, expectations and to give performance feedback. They are the right place to gather feedback on you, others or the company and to get in tune with satisfaction levels. They are one setting in which you can identify potential blockers or ways in which you can help as a manager.

They are the wrong place to discover project status, to understand what that person is currently working on, or to assign ownership on roadmap work. You should discover project state and assign ownership to work elsewhere. If these things come up they should be directly related to the experience of the problem rather than a process of discovery for you. They might want or need help or direction on something. In that case it’s in scope.

A large part of your role as manager is identifying the right people to solve a problem and linking those people together. You’ll probably come across things that are legitimately in scope for somebody to raise with you, but are out of scope for you to deal with directly. If there’s a difficult personal problem, it’s worth understanding where you can help, where the limits of your remit and ability to help are and what options you might have to get additional forms of support – either for you or for your report.

Be prepared

People complain a lot about meetings. Unfortunately I haven’t discovered a more high bandwidth, high leverage way of sharing knowledge than a face to face meeting. What I think actually bothers people is bad meetings. Bad meetings are the bar across the industry right now. There are a few reasons for that. One is lack of preparation, which I genuinely don’t understand. There’s no excuse: Get your shit together and get it done on time. If for a genuine reason you’re not prepared, cancel the meeting. Don’t go through the motions.

As a manager, safety is your responsibility.

To help with preparation there are two note sets that I maintain per person on my team. The first is a feedback diary. A simple bank of short, constructive and positive feedback that I note down over the week. The second is meeting notes. I jot down what we chatted about in bullet point form and identify actions as well as owners for those actions. A good cadence on this means 1:1 prep requires very little overhead. I typically spend 10 minutes per 1:1 sorting this stuff out.

There are some 1:1s that require more than 10 minutes preparation. In difficult performance review situations I like to spend at least 30 minutes with a peer running through what I want to say and how I’m going to say it, to sanity check my position and identify flaws in my reasoning. I’ve found this really useful. More often than not it’s the thing you don’t identify up front that becomes the primary issue, but the act of running through things with somebody else crystallises my thinking and makes it easier for me to think on the fly. I think of this as a kind of code review for managers. Not only a chance to leverage the collective experience but a chance to share context and understanding across the management team.

Follow up

When two people chat each person will leave with their own perspective on what that conversation was about. Depending on many things, those two individuals who think they are completely aligned will in reality range from somewhat aligned to totally misaligned.

To help us get in sync, at the end of each 1:1 I jot down the key points of the discussion as I understood them, note down the key next steps and the owners of those and send that email to my team member. For a small investment of time this has some great upsides, including:

  • I crystalise my understanding of what was important about that conversation by writing it down.
  • I sanity check this against the other person’s understanding.
  • I give the other person the opportunity to clarify my misunderstanding or to identify their own.
  • What’s expected of everyone next is crystal clear.
  • Over time I build a great set of useful notes.

Create and maintain a safe environment

It’s incredibly difficult to have a successful team if your team members don’t trust you. It’s incredibly difficult for them to trust you if you don’t create a safe environment for them to express themselves. The most insightful and useful 1:1 conversations happen when everyone feels safe. It’s not easy to create safety, especially when the stakes are high and people are out of their comfort zones. There’s a whole book on this. I boil it down to:

  • Let people talk, in whatever manner they want, using whatever natural tone or language that allows them to express themselves. This might not be enjoyable for you, but, remember, it’s not about you.
  • If people close off, get defensive or nervous looking they’re probably feeling unsafe. You should pay really close attention and step back at this point. Anything talked about from here on will be low value until you’re both feeling safe again.
  • Unless you get direct and explicit agreement otherwise, what’s said in 1:1s should remain in 1:1s. If Mary expresses a weak desire to move teams and without permission you tell John this and John mentions it to Mary and Peter then you need to find a new team for Mary. Mary’s going to find it very hard to trust you with much from then on. Game over.

It’s worth remembering that as a manager safety is your responsibility. It might even be your primary concern. I’ve been in 1:1s where managers have lost their temper, where they have burst into soliloquy or pontification at the slightest sense of disagreement. When that happens my back goes up. Good luck understanding what I’m really thinking from that point on. I try to remember this when working with my team.

In the aftermath of a 1:1 gone bad I’ve heard managers pawn off the seriousness of the situation with “My intentions were good”. It’s very hard to prove what your intentions were, even to yourself. Also, nobody cares about your intentions. People don’t experience intentions they experience outcomes. If you mistime a tackle in rugby and end up around the opposing player’s neck it’s your fault. Your intentions are irrelevant because the consequences for the player are severe. Even if your intentions were golden you’re leaving the field of play and your teammates behind for 10 minutes, or 10 weeks, depending on the outcome. Team member safety is your responsibility – no excuses. Create and maintain a safe environment.

Schedule effectively – but be flexible

By default I schedule 30 minute meetings with five minutes either side for prep, notes and follow up, so 40 mins per 1:1. I fix this time on a weekly cadence creating an open opportunity to chat and a predictable rhythm. That’s my starting position. Sticking to this schedule as much as possible and giving enough notice at a reschedule is really important. People that rely on you like you to be predictable.

1:1 time is the most valuable time a manager has to have impact.

I’ve found it more important, however, to be really flexible. If you’re only starting to draw out the really useful feedback at minute 25, or something of critical importance comes up in minute 27 the absolute worst thing you can do is indicate you’ve something else to be doing next and there’s a chance you’ll be late. This will be a judgement call but my point here is don’t live by the clock. There are some places you’ll go in 1:1s where you’ll want to stay for an extended period right then and if you interrupt that flow you’ll literally never get back there. So be flexible. Whoever you’ve scheduled next will appreciate this when it’s their turn.

Another reason the bar for meeting quality in our industry is so low is timing of meetings. It’s naive to schedule a meeting, get a ‘yes’ in reply and then to assume that ‘yes’ will continue to apply right up to the start of the meeting.

There are so many reasons why exactly now might not be a good time. I manage engineers. There’s a point of flow in an engineer’s day that they spend most of the rest of the day chasing. It’s the uber productive time where they’re in deep work. It’s the place where they add millions of dollars of value. There is a study that shows when engineers move from that place it takes 20 minutes to get back there. This assumes they will get back there. In practice and with even the best of intentions there might be two hours of elapsed time before that 20 minute process starts. It might be home time then. As a manager, flexibility is part of your job description. I like to open each 1:1 with “Is now still a good time?”. It’s really important to create a predictable schedule but it’s even more important not to be beholden to it.

Adapt your style

I’m inclined to avoid more specific recommendations like “listen more than you talk” or “always ask another question”. In different situations with different people applying these kind of principles has ended up with me listening very attentively to complete silence or irritating an engineer by coming across as a professional socratic questioner and little else. The key point here is be present, use your judgement and adapt your style to the person, the context and the general mood.

Learning and iterating

Over the past few months I’ve found that by following these guidelines:

  • Performance reviews are easier.
  • Joint understanding of expectations of me are becoming clearer.
  • Joint understanding of expectations of my reports are becoming clearer.
  • Post-feedback behavioural changes are more noticeable.
  • Post-feedback tasks are getting done.
  • Indirect feedback on my performance as a manager has become more positive.

There are always areas to improve, but I’ve found the below to be common challenges to watch out for:

  • Concurrent note taking and active listening is challenging.
  • As an alignment mechanism, emails aren’t perfect as they can often go unread. I haven’t explicitly measured this, but I would guess that the read rate on my follow up emails can be 50-60%.
  • Maintaining safety is a difficult art. Sometimes concentrating on total safety can dull the outcomes of otherwise interesting conversations. This is probably because I’m not practiced enough at it yet and it’s tricky to learn something new and engage at full-tilt at the same time. To mitigate for now I’m investing in my apology mechanism 😀
  • I mostly take 10 minutes extra per engineer for prep, notes and follow up. Sometimes it takes me 20 minutes. Scaled up across seven engineers weekly this is a significant difference. I’m exploring ways to make this more efficient and ensure alignment post-meeting.
  • I still haven’t figured out if it’s better to batch 1:1s together in an afternoon to minimise context switching or to spread them out over a few afternoons to optimise for energy. A “1:1 day” sounds like a good idea, but sometimes I’m lacking in energy at the end of the day, which is bad news for the team member in the 4.30pm slot.

Chatting to other engineering managers around Intercom it’s clear that there is no single effective shape or system for 1:1s. Certain formats and systems work better for different people – I understand and learn by reading and writing notes, but others might find this torturous.

What is clear is that 1:1 time is the most valuable time a manager has to have impact. Whatever mechanism or system you use it’s worth understanding if you’re using that time optimally. Since this time is so high-leverage, even minor tweaks can yield significant, compounding results.