How to do the one on one conversations

I have been a manager in engineering for quite some time and I feel comfortable about having conversations with people in general but when I started doing frequent 1:1s I still felt it was quite a challenge.

How could I create enough value from these conversations? Spending time with me had to be at least as valuable as spending that time with the team on engineering. How would I know what to talk about and how to find the right topics when things are going well?

As we all know, you learn from your experiences and now I feel comfortable with the tool and how found my way to do them in a way that creates value for me and the people I work with. I have also learned that the amount of trust you can build and the level of insights you can get from doing these 1:1s are amazing and the time investment is totally worth it.

The structure

Frequency

In my current work environment I have a small set of managers and engineers that reports to me and I meet some of them on a weekly basis and some of them on a bi-weekly basis for a 1:1 session. The frequency and length of 1:1s have varied for me depending on the needs of the individual.

Sometimes someone is going through a tough period or needs lots of support for other reasons and then weekly is valuable since you keep the momentum up. In some specific cases I meet even more often for a short period of time to give support or frequent feedback on a specific topic.

For more senior people, or when everything is going smoothly, bi-weekly is often sufficient. And at any point, if we in a 1:1 find that we don’t have anything important to talk about, we end the meeting early since time is valuable and we should spend it on the right things. When deciding what is important you need to keep in mind that even small talk can be important in building a strong relationship why you need to make sure to have time for that.

Agenda or no agenda?

My basic approach is that the person that I am coaching sets the agenda why I always start with the question “what should we talk about today“. If I have things I would like to talk about I would add them to the list of things the person wants to talk about. If the number of items is more than we can cover in our time slot I would make sure we prioritize the agenda together before we start.

Sometimes I have important things that I want to bring up in a 1:1 and if preparations i needed I would announce that before (I would like us to talk a bit about … in our next 1:1) so that the person is aware of of the topic and able to prepare.

When we have a bigger topic that we need more focused time to work on together I would either use a scheduled 1:1 or book a new session for this topic. It is not unusual that we discover topics in a 1:1 session and decide to focus on digging deeper into that topic in the next session. Examples of topics for this kind of focused session could be around motivation, a deeper issue with a colleague, need for support around a specific work task, assessing where the individual is placed according to the career framework or to defined new goals for the individual growth.

Notes or no notes

I find it useful to have some short notes from the 1:1 sessions and I think that they should be shared between the individual and the manager. The reason I think the sharing part is important is because the 1:1s are not owned by the manager, they are own by both of you why it makes sense that you share the notes. As the manager I take more ownership on (trying to) keep up with the notes as a “service” to the other person but both of you should be able to add things to the notes.

The value I get from the notes are when we might want to go back to something we talked about before and we wonder how long ago it could be, or if we don’t remember exactly what it was about. They can also be used for inspiration when putting together feedback for a longer period in time. Sometimes I have given feedback in the 1:1 that I want to make sure is received and accepted by the other person, and then I could write the notes and make sure that the other person is agreeing on that the notes are a good summary of what was said.

I usually have a document that is shared between me and the other person and in that doc we (most often I) write short notes, add pictures of notes I have been taking on paper or on the whiteboard during the session. For me personally it does not feel good writing notes on a computer during the 1:1 session since I think it is hard to have a close and deep conversation with a computer screen between us but I know that setting works well for other people.

Most of us live a busy working life and I have to admit that there are times where I get behind on the notes taking even though I am doing the “uploading pictures approach”. Even if that happens from time to time I find it useful to have the ambition of always taking notes and then accept that I will sometimes fail on it.

Things to talk about

The topics for the 1:1s vary over time but there are two things that I always ask:

• How are you doing? How are things?
• What should we talk about today?

I always start with the how are you doing question, not because it is a good conversation starter but because I really care. And if someone is not doing well that is the most important topic to cover why we should start there. Sometimes people say that “things are ok” and then I ask a bit more what that means since ok can be good, bad and everything in between.

What should we talk about today? As described in the agenda section I think it is important to give room for people to set the agenda (in some places it is actually expected that people should set the agenda and drive their own growth). Sometimes people are struggling with finding the topics and even if I think you should cancel a meeting if you don’t have anything you need to talk about it is too easy to end at this point. 1:1s is a good place to support growth and uncover improvement opportunities why we need to do some digging before calling it the day. Some questions that might help revealing interesting topics could be:

• How are things in your team?
• Are you feeling challenged? What have you learned this week?
• What are you looking forward to the most? What things that we have coming do you think will be most fun?
• When did you have most fun last week? When did you feel bored or frustrated recently?
• Which of your accomplishments last week are you most proud of?

Another tool I think is awesome and use frequently is the barometer exercise, it is a super simple tool that can reveal super interesting topic that we did not find in other conversations. I believe what is making the exercise powerful is that it talks about trends that open up thoughts around worries and excitements in a natural way and by asking about what you could do to impact the movement just a little bit it is easy to identify concrete actions that will help us move in the right direction.

Questions I generally ask somewhere in our conversations where we discuss a topic when we talk about different things are:

• What do you think we should do about this? Do you have any ideas around how to handle this situation? Can you do something to improve this? This is about giving room for people to explore a problem to understand it and to identify potential solutions and actions that could help solving the problem.
• What did you learn from that experience? This is the classic continuous improvement question. Helps reflection around behaviors, growth and to identify needs for tech improvements .
• How would you like me to help you? What kind of support do you need from me? I am using this question more and more and I think the reason for that might be that I previously felt like I should know what to do without asking. I have realized that asking this question is really helpful for me to understand the expectations but also for the person to reflect upon what kind of support he/she needs.

When someone has a problem

It is common that people bring up problems they are experiencing in their 1:1s. This is a great opportunity for you as a manager to support them and you need to pick the right strategy for doing giving that support. If the person is unexperienced you will probably have to do more active guiding through the conversation and also likely in the end give advise about what they should do. When working with more experienced people you might take a more lean back coaching approach and let them find their path with some gentle guidance from you.

To give you an example of what a conversation around a problem could look like you can picture yourself in a 1:1 with a person that is experiencing collaboration problems with a colleague.

• Understanding the problem from different dimensions
  • Why is this a problem for you?
  • Is this a problem for the other person as well? How do you think the other person see the situation?
  • Are others involved or affected by this problem?
• Understanding how a good situation would look
  • If you would do something about this problem; What would be best possible outcome?
  • What would be the best possible outcome from the other person’s view?
  • Would there be any side effects of this positive outcome?
• Understanding if there are any risks by taking action on the problem
  • What would be the worst possible outcome?
  • What would be the worst possible outcome from the other person’s view?
  • Would there be any side effects of this negative outcome?
• Getting into solution space
  • Do you see any steps you could take to come closer to the outcome you would like?

What I try to achieve with these different set of questions are to broaden the perspective to make sure to see things from the “other side” as well and to understand if it is a good idea to act on fixing the problem or not.

Covering the technology aspect

The 1:1s need to cover all aspects of an engineers life and technology questions can be covered when going through day to day challenges, growth goals in technology, new frameworks that the person would like to introduce or knowledge sharing. I don’t find 1:1s as the best tools to do mentoring or discuss about code and most often that kind of hands on support has been better provided in the team context than in the 1:1s.

One thing I did recently with an engineer I am working with was to walk through a few examples of code changes that he had done and was proud of. I found that exercise super interesting and valuable since I got to see the actual code and more importantly heard him describe the change, why he had taken the decisions he took and what he liked about it. It was also a good opportunity for me to get a better picture of how things are connected and the challenges we have which is also helpful. Going forward I will make sure to do these kind of sessions from time to time since it really helps broadening the picture and is a great addition to the other activities we do in the 1:1s.

What you do as a manager in the 1:1s

Importance of listening

• You need to make the person comfortable by showing that you are interested in what they are going to say.
• You need to give space for the person to think things through. Even when you might feel that the silence is awkward.
• You need to be curious about learning more about the person and about finding new insights that helps the both of you to understand the behaviors and beliefs that the person hold
• Even when you disagree you need to have an open mindset and truly listen to understand the persons perspective before coming with your own argument. This is important because you want to show that you are interested in hearing their opinions and because you then can give your arguments including the perspective that the person brought up.

The 1:1 situation is totally focused on the other person and you really need to use your listening skills to get good value out of them. This is your opportunity to really understand what the individuals are thinking, help them find a good way forward and for you to understand how you can support them on their journey.

This post about communication has a section about active listening if you want to read more on that topic.

Adjusting your style depending on situation

The greatness of 1:1s is that they are so easily adjustable to suit the needs of every individual. This is important since all of us are unique and we have our own ways of learning and communicating and as a leader you want to create a situation where the individual can be at their best.

One part of this is to adjust the setting and your communication style to fit the person. It could be about deciding on topic before hand to enable preparation for a person that needs more time to thing things through. It could also be about your style in the conversation, how much you guide the conversation with leading questions and how much space you give for the person to come up with the answers themselves.

It is a lot about coaching

The 1:1s are a great place for you to help the person you are working with learn more about themselves or how to move forward with their problem.

I am working on a post on how I do coaching and what I have learned from my coaching experiences. When that post is in place it will be linked from here.

Pitfalls that I have experienced

When thinking back at 1:1s I have had and feedback I have gotten there are a few things that I continuously reflect upon around the 1:1s I have with the people I am the manager of.

Constant coaching mode

It is often a good thing to drive conversation by asking questions. Techniques like “the 5 whys” are powerful to dig deep and get to the bottom of questions but it is important that you choose to answer with a question when that is appropriate and that you choose to answer with and answer when that is appropriate. Examples where it might be relevant to provide an answer instead of a coaching question:

• when the individual needs your support in finding the right answer
• when the person could benefit from not having to come up with the answer. If every conversation is about identifying problems in yuor surroundings and the answer is “what can you do about it” it might feel good if someone else sometimes takes over the burden of finding that answer.

Acting on less important problems

In a coaching 1:1 you might discover issues in the team that we might benefit from fixing and it is very easy to go directly from discovery into solution space just because you can. One thing that is easy to forget before investing energy in digging deeper in this problem we have discovered we need to make sure that it is the right thing to do. We need to think about the current focus in the team, other improvements that are already being driven and actions we have decided on in retros to make sure that this problem that we just discovered is important for us to focus on right now.

If the problem is critical enough it will always be the right thing to try and fix it but otherwise it is important to look at the holistic picture before going forward.

Be too focused on seeing the bright side of things

I am an optimistic person that always try and find the good sides of things and focus more on moving forward than being sad about the past. I believe that it is important to try and improve things instead of getting stuck in being disappointed in how bad things are (even if those feelings are super natural and I also struggle with that at times).

One consequence of this that I am now working actively on is to make sure that I give enough space for the person to express the “bad side of things” before moving into seeing the more positive aspects. This is important to make sure not to miss improvement opportunities but also to make the other person that is experiencing things as bad to feel heard and listened to since that is important for that person to be able to join me in the solution space looking forward.

How to know if the 1:1s are working

The generic answer to this question is that the 1:1s are working when both you and the other person gets enough value out of them. To answer that question you need to go back to the question of why we are doing 1:1s in the first place.

For me as the manager the 1:1s are a tool for me to understand what a person needs support with, identify ways to support those needs and provide coaching support when that is relevant. For the individual the high level goal with 1:1 can be to bring up problems/concerns/questions and ask for support when needed. When I start working with a new person I usually ask what they would like us to talk about in 1:1s and if there is something in particular that they want us to cover in those sessions.

When you feel like the 1:1s have become a bit lame

Sometimes I end up feeling like the 1:1s are not delivering as much value any longer. It might get hard to find juicy topics to talk about and you might end up cancelling them, ending early or just chit chat to let time pass (this does not mean that I believe that chit chat is not valuable, it can be super valuable to bond and build a relationship, but some chit chat are not like that but more about not being silent).

What I have been doing a few times when being in this kind of situation is to do a retro/set expectations session around the 1:1s. We have together explored topics like:

• What is working well in our 1:1s
• What is not working well in our 1:1s
• What is it that we want to get out of them
• Which actions should we take to improve them and get the value that we are after

Doing this kind of session has been a good way to re-start the 1:1s and get new energy and more value out of the tool.

The powerful ending question

Something I try to do in the end of my 1:1s is to ask some “continuous improvement questions”. I alternate between these questions depending on which kind of session it was and how much time we have left. I don’t ask it every time since that might be tiresome for the other person and sometimes we don’t have any time left.

Some of the questions I might ask are:

• How did you experience this 1:1? This will give me an answer that tells me if the whole experience was good/meh/bad but not give that much input on how I should tweak the session to increase the value.
• What do you think I should change in our next 1:1 to increase the value? Similar to the question above you will get a good feeling for the whole experience but you are also more likely to get ideas for improvement.
• What value did you get out of this 1:1? This question will give you a picture of what kind of value your 1:1s are giving to the other person and if that is inline with the value you are expecting. If you suspect they are not delivering enough value, the answer could be a great conversation opener around what value each of you are expecting and how to get there.

In Short

If you are curious about the person you are working with and are truly interested in understand their perspective and find ways for you to support them – that is a really good start for successful 1:1s.