If you have been doing one-on-ones with your employees (or your boss), you might have experienced a certain kind of conversations. They drag along awkwardly, or feel a bit shallow. You do not make progress on anything meaningful. Instead, the conversation is little more than a status update. But status updates are not what one-on-ones are for, because you could have those “out in the open”, without meeting privately. The real value of one-on-ones is to make progress on the employee’s long-term goals, to build rapport, to identify problems that keep the employee from reaching her full potential, to toss half-baked ideas around, and so on.

If all of this does not happen during a one-on-one, the conversation can feel a bit strange and forced. This is especially true if the same patterns with roughly the same questions keep coming up over several conversations, without much feeling of any kind of progress. Let’s look at a (part of a) “shallow” one-on-one between Sophie, an engineering manager, and Mike, one of her engineers:

Sophie: “Hello Mike. How is everything going?”

Mike: “Pretty good. We still have quite a bit to do to finish the current sprint, but I think we can manage it.”

Sophie: “Let me quickly go over the notes from last time. So, we talked about improving the percentage of reviewed code in your team. I hear that this has really picked up.”

Mike: “Yes, we are doing code reviews for every commit that goes into the core package, at least, and for most commits to the other packages. I think it has improved our code quality a lot.”

Sophie: “That sounds good.”

Mike: “Yeah, and we were also able to increase our test coverage. We added the relevant Sonar graphs to our dashboard so that everybody can see them all the time, or at least once a day or so. It’s motivating to have that, and to see the coverage grow over time, as well as the technical debt shrink.”

Sophie: “That’s a good idea. I have the feeling that you keep improving as a team.”

Mike: “Yes, we look at inefficiencies regularly, and try to find solutions for them.”

Sophie: “So what would you say is the biggest pain point at the moment about working here?”

Mike: “Hm, to me, it is probably the noise level. I find it too high sometimes, but I also don’t want to wear headphones all the time.”

Sophie: “Yeah, I know. I find it annoying myself sometimes. If I find it is unnecessarily loud, I sometimes go and ask a few people to take their conversation or phone call to a meeting room. Maybe you can start doing the same.”

Mike: “Yes, I can try.”

Sophie: “Do you feel the workload can be handled well by the team?”

Mike: “Yes, I would say it can. Over the last two weeks, our backlog has been growing slightly, but that was rather due to the brainstorming session that we held. A couple of tickets came out as a result of that. Overall, I am certain we have increased our productivity over the past months. We have been pairing a lot, and everybody knows about our hairy topics at least to some degree now. Also, our estimates have become very accurate.”

Sophie: “Sounds good. What about you, personally? How are you currently feeling about coming to work here?”

Mike: “Good. Really, I like it. I like my team, I like the work that we do. I think we are making good progress.”

Sophie: “Do you have enough opportunities to learn?”

Mike: “Yes, again and again. At the beginning of the year, there were a lot of new things we started using, and I learned a great deal there. We started using SaltStack to provision our infrastructure, and I had to read up on OAuth. Recently, it has been a bit quieter, so I had time to grab a book.”

Sophie: “Oh, what are you reading?”

Mike: “The ‘Principles of Package Design’ book that some people recommended.”

Sophie: “Ah, right, Paul and Evan said it was useful, as well. I haven’t read it yet, but I want to.”

Let’s pause here for a second. This is all fine and dandy, but there is not much in this conversation so far that justifies a private meeting in a booked conference room. It’s mainly status: Current sprint almost finished, backlog size stable, atmosphere on the team good, doing more pair programming than before.

To give Sophie credit, she does try to bring up the topic of Mike’s personal development by asking if he thinks he has enough opportunities to learn. She also looks for ways that the organization can improve (“biggest pain point”). However, these questions do not yield that much follow-up discussion, and the conversation is a lot like question, answer, question, answer, without anything like a natural conversation flow. Mike seems pretty satisfied with the overall situation, has no real complaints, and does not seem particularly eager to talk about himself so much.

Ways out

At this point, it would be good to have some questions and techniques to get Mike to open up a little bit. Many software engineers are introverts and feel a bit uncomfortable with this kind of undivided attention from their manager, so you have to break through the surface with them and go a bit deeper.

Of course, I am not the first to write about this situation. Rands’ famous The Update, The Vent, and The Disaster recommends three ways to turn a status-heavy conversation into a different direction:

1. Have some prepared points to talk about.
2. Do a mini-performance review.
3. Talk about a current problem that you are facing.

Holding up the mirror

I want to focus on the first suggestion of those three, the prepared points. Specifically, Jason Evanish compiled a great list of questions that you can use for this purpose. The list is divided into categories like Short Term Goals, Long Term Goals, etc. Let’s pick something easy to start manoeuvering out of the dull grey of mere status update. Sophie will encourage Mike to take a look in the mirror by asking him to do some self-assessment:

Sophie: “What do you think are the key skills for your role?”

Mike: “Hm, the key skills… I think thoroughness is very important, so that you don’t deliver half-finished solutions and toss things back and forth with QA. Then, let me think… When you have to diagnose some defect, and it’s urgent, it is important to be able to focus under pressure, and keep a cool head.”

Sophie: “How would you rate yourself for thoroughness, and for focusing under pressure?”

Mike: (smiles) “Ha, I had a feeling this would come. Well, thoroughness… I think I am doing pretty good there. I really think through most aspects of my solutions, and write good tests, as well. Few of my tickets ever come back to me. But debugging under time pressure, I have to say, is not one of my favourite occupations. I cannot think very well when I know that every second counts. I think my strength is planning ahead, not fixing things after the fact.”

Sophie: “Can you use this strength in your work here?”

Mike: “Of planning ahead? Hm… To some degree, I would say. Within a limited frame. I mean, I plan my tasks out so that I know how to best approach them, in which order, and so on. But this is not what most people would call planning.”

Sophie: “Would you like to do planning on a larger scale? Like writing design documents?”

Mike: “Yeah, I think this would be interesting. I would definitely want to try it.”

Wow, what just happened? Sophie asked about the key skills that were, in Mike’s opinion, required for his role. Through clever follow-up questions, she found out that Mike is not fully happy with one aspect of his job (fixing things under time pressure), but would like to use a different strength more (planning ahead). This is an opportunity for Sophie to gradually redefine Mike’s role to match his talents better - which is one of the absolutely most important tasks of a manager.

As an aside, it is not necessary and probably not possible to have a solution ready for every vague wish for role redefinition. If somebody wants to move into management, you cannot just promote them. But it is a good idea to keep these preferences in the back of your head in case an opportunity turns up.

Checking for happiness

In the first dialogue above, Sophie asked Mike for his biggest pain point about working in this company. This is a good way of soliciting for individual things that could be improved. However, they do not tell you if the employee is satisfied overall, or not. Sometimes, employees do not even know that they are becoming unhappy, because this can be a very gradual process. You, as a manager, can probe for early warning signs. Sophie does this by being brisk about it:

Sophie: “What would make you leave this job for another?”

Mike: “Hm… I think I would really enjoy working with artificial intelligence, or Natural Language Processing. Those were my favourite fields in university, but I could never really get back to them. There are not that many jobs that require these skills.”

Being open about the fact that neither you nor your employee are likely to stick around until you retire is a good thing, because it increases honesty and trust between you. However, in this case, Sophie can probably not just come up with an AI research project to make Mike happy, so she checks for warning signs a different way:

Sophie: “Imagine it’s Sunday night. You had a great weekend, and you will go back to work on the next morning. How do you feel about it?”

Mike: “Good. I’m looking forward to working with my team.”

Okay, no obvious warning signs. Sophie tries to get Mike to talk a bit more by asking for something more specific:

Sophie: “Can you tell me about a time when you enjoyed working here the most?”

Mike: “Let me think. When I figured out the new bot detection mechanism with John and Stella. That was really cool. We had a challenging problem, we worked pretty autonomously, and we all learned quite a bit. I also felt the trust that the company had in us to come up with a working solution, and that was very motivating.”

Sophie: “Do you think such an enjoyable experience could be repeated more often?”

Mike: “Maybe, yes. I think that sometimes we are seen as mere implementers instead of people who contribute their creativity and find solutions.”

Sophie: “Do you have an example where you would have liked to give more input?”

Mike: “Oh, certainly. For example, the handling and the user experience of the new reporting module seemed to me all done and set in stone when I first saw the concept. I think we would have arrived at a better solution together. In fact, I had some ideas for improving the handling, but couldn’t get them in, because nobody seemed to be willing to take another round on that.”

These few questions unearthed, in a very short time, some interesting anecdotes about Mike’s motivation, and about things that might be going wrong in the company. It seems that developers’ input is not asked for in a lot of cases. Mike therefore gives an important hint at a potential dysfunction in the organization, and Sophie should ask herself - and others - if this is a well-founded complaint.

What’s on your mind?

Besides self-reflection, employee happiness, and organizational improvement, it can be a good idea to create some space for an informal exchange on non-work related topics. Maybe Sophie noticed that Mike has been kind of down lately, and interacting with others less than usual. He hasn’t brought this up by himself, so she asks.

Sophie: “I have the impression that something is worrying you. If you don’t want to talk about it, that’s fine of course. But if you do, I will gladly listen.”

Mike: “Yes, there is something. My girlfriend and I are breaking up, and I have to find a new flat. That’s pretty painful at the moment, and I am nowhere near finding a new flat, which doesn’t make it easier.”

Sophie: “I see. I’m sorry to hear that. Is there anything I can do to support you? Do you want to take a couple of days off to look for a flat?”

Mike: “It’s not exactly the best time to leave the team, but on the other hand…” (pauses)

Sophie: “I just know I would not be fully productive if I was worrying about a breakup and finding a flat. So maybe it’s better to fully concentrate on that for a short while, and try to go back to normal once it has been solved.”

Mike: “Yeah, maybe you are right. But I will do some work from home in between.”

Sophie: “I will leave that up to you. Just don’t forget to find a new flat.”

Mike: “All right, thanks, Sophie.”

Sophie now knows why Mike is behaving differently, and can adapt her expectations towards him, or temporarily reshuffle her teams so that all deadlines are met.

Rotation and preparation

The dialogues above are just some examples of how you can steer a one-on-one in a million different directions. Jason’s list is a great resource for opening questions. The important thing, however, are your follow-up questions. They are your tool to establish a natural conversation flow, so that the meeting does not feel like an interrogation.

In consecutive one-on-ones, vary with the topics you cover, and the questions that you choose. For example, do not try to talk about long-term goals every single time, or you will sound like a parent preaching to her children to think about the future. Use your notes from previous meetings to establish a good topic rotation, and to prepare a couple of questions for the next meeting. If all else fails, do it like the German coast guard and ask them what they are sinking about.

Time investment

This blog post took me about 8 hours to write. Some of it happened in a vacation park in the lovely Zeeland province during not so lovely weather.

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