What to Talk About and How to Do It

With the initial one-to-ones handled by the contracting exercise, you have a clear structure for those initial meetings. But what about the next meeting and every meeting after that, forever more?

I tend to use some simple repeating patterns for content. First off, it’s essential that you prepare. I have a recurring to-do list item that repeats on the day of each direct report’s one-to-one reminding me to spend some time before the meeting putting the agenda in order. If I haven’t already noted down some items to talk about, then I’ll have a think and pre-fill the agenda with some items. These can be anything from:

• Observations from the past week, either about their work or the team’s. These can be good or bad observations, or even just areas where I’d like to probe a bit further and find out more.

• A deep dive into a project or piece of architecture that they’re working on.

• Updates that will be interesting for my staff, such as what has recently gone on in any other meetings that I’m part of, or in my case, anything my own manager has told me, such as relevant things discussed at the last board meeting.

• Coaching. We’ll learn more about coaching in Chapter 9, ​How to Win Friends and Influence People​. You can help your staff pick through their own problems.

But even if you have fantastic content to cover every week, you can still get your one-to-ones very wrong if you don’t approach them in the correct way.

It’s Their Meeting, Not Yours

Despite the fact that your one-to-ones are your best chance to positively impact your staff each week, the paradoxical stance that you must adopt is that the meeting is theirs, not yours. What this means is that you must “keep the thought bubble over their head” for as much of the meeting as possible. Do this by asking leading questions, nudging the conversation in particular directions, and most of all, by listening. It’s not your job to direct the conversation or pontificate in this meeting; it’s your job to absorb and guide.

Try and get your direct reports to do 70% of the talking. If you feel like solving their problem for them, don’t. Ask another question and let them arrive at the conclusion themselves. This is an art that takes some practice, although some are naturally good at this with little to no training.

You can achieve this by asking lots of leading questions, rather than providing all of the answers. For example:

• “How has your work been going this week?”
• “What are you working on today?”
• “Tell me about those production issues we had last week.”
• “Do you think that we’re measuring our uptime well enough?”
• “How are you feeling about our deadline in June?”
• “How best could we ensure that we’ve got all of the right metrics being logged ahead of time?”

Although seemingly convoluted, leading questions work well. They encourage good discussion, and they can be used whether you actually know the answer or not! Use them to your advantage.

Silence Is Golden

Don’t feel like you’ve got to fill every moment of airtime with conversation. I’ve found that time and time again if you let the dialog unfold and stay relatively quiet using subtle prompts, the best parts of the conversation are to be found. For example, if your direct report is discussing some issues that happened in the previous week, letting the conversation tail off without replying can help surface an issue: “…and that’s the problem, I guess. I just have no idea why they aren’t helping us more.”

Once again, this is why this is their meeting and not yours: let them dig into their mind and surface the issues that really matter to them. They’ll know.

Updates: The Boring Part

One-to-ones are not status update meetings. Don’t make iterating through the tasks that your staff are working on the primary purpose. Ideally there’s already another place where you could find out this information if you wanted to, such as the team’s tickets. However, there will always be some element of updates in these meetings from both sides.

But updates should not be the core element of the meeting. They’re an aside. I’ve been in one-to-one meetings in the past where my manager has walked through a checklist of the tasks that are in flight and asked me for updates on each of them. This doesn’t progress your relationship, fails to focus on personal development, and most of all, is extremely boring.

You can make updates more interesting by being creative. Instead of just nodding and listening to what they’ve been doing, why not probe deeper by asking some questions?

• “How could we deploy that into production quicker?”
• “Is this the correct technical approach? What are some alternatives?”
• “Have you seen any open source software that could solve that problem for us?”

You may have absolutely no idea of the answers to any of these questions, but they work well for stimulating discussion. Keep updates to the bare minimum required, though. Free up most of the space to talk about wider issues around the work and their personal development. You’ll both be happier for it.

Pulling the Andon Cord

Particular directions that the conversation can go in your one-to-ones may make the other person feel uncomfortable. This can happen for a multitude of reasons: either a subject is too personal, too off topic, or requires the support of someone that is better placed to address it. In his book Toyota Kata, Mike Rother details how production lines at the automobile manufacturer would have multiple cords that should be pulled by any worker as soon as they noticed a defect. This was called the Andon Cord: the word andon means sign or signal. It would stop the whole production operation so that leaders could solve the problem, and then production would resume. You could implement your own metaphorical Andon Cord in your one-to-ones. If either party is uncomfortable with the current topic, you can stop the conversation and enquire as to why. Once that’s resolved, you can continue.

Ideas for Topics of Conversation

If you have a particularly quiet direct report, or if you’re just looking to mix up the material a bit, then here’s a whole bunch of example topics that you’re welcome to use for yourself.

• Architecture deep dives: At irregular intervals, I find it fun to ask my direct report to take me through the latest architecture of some part of the system that we’re working on. I ask questions about various parts in terms of speed, resilience, redundancy, and so on. This sometimes highlights some weak points, but mostly I get a chance to better understand the work and the part of the infrastructure that it belongs to.

• Process deep dives: How many steps does it take to get something done, such as releasing code to production? Why is that? Could those steps be reduced, and if so, how? Could any processes be removed completely?

• A relevant article you’ve seen: I typically read a bunch of technology sites, such as Hacker News. If there’s something interesting I’ve seen—either as a subject or as an open source project—I’ll talk about it. We can discuss what we’re doing in that area, if anything, and try to pick it apart. You’ll find these discussions always find their way back to what you’re working on.

• Teaching: Once you’ve finished this book, you’ll have a whole host of topics to talk through with your direct reports. If you share them, then they’ll be able to see more of the world through your eyes. For example, have they ever thought about delegation and how they could factor that into how they share work with less senior staff so they can learn new skills?

• The department or company direction: What do they think? Do they feel confident in where the company is going, or do they have reservations? If so, why is that? Is there anything that you could do to help?

• Collecting feedback: Has anyone on the team been particularly helpful recently? Gathering this and then delivering it to that person is a simple task but can make people feel appreciated.

• Sharing a task you’re working on: People are always interested in what their managers are working on, so why not go through it together? Are you writing a job description, discussing the roadmap with your Product Manager, or working on some code of your own? Open the lid on the box and get their opinions. They’ll appreciate you sharing and will often have some valuable input.

That’s just a sample of some things that you can explore in your one-to-ones—in theory the list is endless. However, the connecting themes are sharing, building trust, and thinking through technical and interpersonal problems. As long as you’re spending some time on one or more of those things, you’re having a valuable one-to-one.