One-to-Ones

You’re going to be spending a lot of time in one-to-ones, so it’s in your best interest to be able to do them confidently, comfortably, and to get the most out of them. there is a vast difference between having an unprepared chat and having a meaningful, focused one-to-one.

Month in, month out

One-to-one meetings form the core of the professional relationship you have with your staff. They are the point during in which you both give up your time to be together. High-quality one-to-one meetings build high-quality relationships. They allow you to engage with your staff on a deep, personal level. A steady cadence and regularity are key for these meetings. It brings predictability into your relationship, demonstrating that you’re there for your staff month in, month out.

How to Prepare for One-to-Ones

Setup a recurring bi-weekly or monthly meeting booked in with your direct reports. Don’t move them around unless absolutely necessary: you’ll want to have a predictable, safe, regular touchpoint with your staff that they can rely on. The second piece of preparation you’ll need to implement is a rolling agenda that guides your meetings. The easiest way that I’ve found to do this is by using a shareable document. If you MS Teams, you can setup the integrated meeting notes like I do. A private document is a great way of recording what is discussed within your one-to- ones and capturing actions that either you or your staff have to do.

Contracting: Your First One-to-Ones

Your first one-to-one meeting can be somewhat harder than the ones that follow. Rather than risking your new relationship with your staff getting off to the wrong start, there’s a useful exercise that you can both follow that allows both parties to openly talk about what they expect from one another and then outline their wants and needs from the relationship. This exercise is called contracting.

What is Contracting?

Contracting is simply a set of questions that you can work through in your first one-to-one that provokes conversation about what is expected from you and your direct reports. These expectations come from both sides of the relationship. The contracting exercise forms a wrapper in which you can talk about each other’s needs in a structured and safe way, promoting candid and transparent conversation that should continue into the future.

1. Which Areas Would You Like the Most Support With?
2. How Would You Like to Receive Feedback and Support?
3. What Could Be a Challenge of Us Working Together?
4. How Might We Know if the Support I’m Offering Isn’t Going Well?
5. How Confidential Is the Content of Our Meetings?

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.

1. 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.
2. A deep dive into a project or piece of architecture that they’re working on.
3. 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 top-level leadership meeting.
4. Coaching.

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. 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. 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/month.”
• “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?”

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 rela- tively quiet using subtle prompts, the best parts of the conversation are to be found. nce 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. However, there will always be some element of updates in these meetings from both sides. You can make updates more interesting by probing deeper and 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?”

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.

1. 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.
2. 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?
3. A relevant article you’ve seen: I typically read a bunch of technology sites, to understand what’s relevant in the technology, framework and language world. 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.
4. Teaching: a whole host of tips 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?
5. 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?
6. 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.
7. 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.

How to Take Notes and Assign Actions

Throughout the one-to-one, it’s useful to jot down notes and assign actions in the shared document. Review the actions at the end of the meeting.
I use a bullet point format to arrange information, and actions are always in bold font.
When you assign actions to yourself, make sure that you put them on your to-do list to action. There’s nothing better than having a manager who actu- ally acts on the things that you bring up in your one-to-ones. You’ll be sur- prised how many people I talk to that feel that their manager doesn’t.

And finally remember: You Are Not a Therapist!

As a diligent, caring manager who is excellent at listening, you may experience your one-to-one sessions turning into therapy sessions for your staff.
If you feel that your staff primarily use your sessions to vent with no solutions proposed, or to talk about in-depth personal issues that aren’t related to work, or if you begin to notice signs that you think that your staff are going through difficult times or may be mentally unwell, the best thing that you can do is to raise your concern and ask whether they would be interested in talking to a qualified independent third party. If you’re in a company of reasonable size, you may have an HR department that can help. Seek help from your own manager, too, about what to do.

What’s Next?

There you have it: you have everything you need for great one-to-one meetings with your staff. As you spend more one-to-one time with your staff, you’ll begin to understand their individual personalities, motivations, and desires.