Normalizing your first one-on-one meeting

Your first one-on-one meeting can be somewhat harder than the ones that follow. Just like meeting any human being for the first time, your first one-on-one could unfold in a multitude of different ways. You might be lucky enough to immediately gel with your direct report. The conversation flows and away you go. Or the conversation may fall flat. Is there a method to normalize this first meeting so that it works better for both parties?

If you’ve started your managerial role in a new organization, you will not know your direct reports intimately, which may make it challenging to judge the right level of formality to bring into the meeting. On the one hand, you’re their manager, but on the other, you need to be their ally. You don’t want to be too serious as you may risk causing alienation. However, being too jovial might come across as strange depending on the person and the existing culture of the organization.

Even if you’ve been promoted from within, that doesn’t necessarily mean that these meetings are going to be any easier. In fact, they could be more awkward because your relationship between you and your colleagues could be changing. Close peers may now be subordinates, and this is a strange and potentially difficult change to navigate through, especially if you and your peers have become good friends. This is starting to get complicated isn’t it? What should you do?

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 outline their wants and needs from the relationship. This exercise is called contracting, and you’re going to learn how to do it.


When preparing for your first one-on-one, explain that you’re going to do a short exercise to understand how you can best support your direct report as their manager. How you prepare is up to you to decide. You could leave it until the meeting to reveal the questions, or you could forward them to each of your direct reports ahead of time so that they can consider them carefully. With time, I’ve gravitated toward the latter, since the quality of content tends to be higher.

Remember that both of you should be answering each of these questions in relation to one another. This isn’t a one-way exercise. You support each other in your relationship. With the questions at hand, spend your first one-on-one working through them with each other. With a bit of luck, you’ll find that:

  • You will have both discussed what you hope, want, and need openly in a structured way that does not make either party feel uncomfortable.

  • You’ll have begun your relationship by talking candidly, which should set the tone for further interactions.

  • You’ll have plenty of material to talk about going forward.

Let’s have a look at each of the questions. They’re the same ones that I use in my own contracting sessions. However, they should only serve as a guide. If you want to change them to suit you, then by all means, do so!

1. Which areas would you like the most support with?

The first question is a broad one. It’s broad on purpose because each of you may need support in potentially any area. For example, you as a manager may need help from your senior engineer to better understand the technical challenges that the team faces in their technology stack. They may need more help in promoting their own architectural ideas within the team and beyond. As well as technical challenges, there may be interpersonal issues that require support, such as being able to work better with difficult colleagues in their team or working on self-confidence in debate and discussion.

Resist the urge to suggest areas yourself if they are struggling to come up with them. Seeing as you are their manager, they may assume you’re suggesting them for some purpose and agree with you when in reality all they needed was some more time for those answers to unfold. Simply say it’s fine not to have clear ideas right now, but you’re there for them at any time they need you. Also, make sure that you note everything down in your shared document as you talk. Now, it’s on to the next question.

2. How would you like to receive feedback and support?

This is about working out how the other person likes to operate. Everyone’s personality is different, so it’s important that you both feel comfortable with the manner in which you interact.

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