The First Three One on ones

How To Start Managing People – The First 3 One-on-Ones

When I joined Contentful in 2018 I found myself in a new country, a new type of company and in a new team. I’d been an established engineering manager by then, but starting out in an entirely new environment was still really stressful. One major source of stress was having to form all those new relationships with my new direct reports. How do I even start? How do I build trust? What should we even talk about in our first sessions together?

Many managers are anxious about starting to manage new engineers – be it a new teammate in an established team, or taking on a new team or a new job. They want to create meaningful, trusting relationships, but don’t know how to start.

By the end of this article, you’ll have three tangible ideas of what to talk about in your first few one-on-ones. I’ll give you topics, talking points and templates.

(If you’re interested in what one-on-ones are about in general, read “The basics of one-on-ones”)

Each individual and situation might need a different approach. Make sure you learn about different leadership styles and when to apply which.

Firstly, agree on a schedule

It’s very tempting for busy managers to fit 1:1s in their Swiss cheese-like calendar, but some engineers actually care about the timing. Be a good partner and ask your engineers about their preferences – you’ll be surprised. Some of them prefer a specific session length, days of the week or even time of the day. Always ask, never assume. This is one of the first impressions you’ll give your new reports—remember, you’re to serve them, not the other way around.

The first one-on-one – setting the scene

set the scene

The first one-on-one – setting the scene

If you’re lucky, you’ll have already had a handover session with the previous manager and the engineer, so you have a high-level understanding of their journey.

Regardless, start the first 1:1 with introductions. Talk about your respective career journeys, experience, aspirations. Take notes, there’s a good chance you’ll already hear a couple of points you’ll want to talk more about later.

Now, avoid being formal here. You’re setting the tone with each 1:1 session, and you want a friendly atmosphere. Be sure to be relatable, share personal stories and throw in some fun. This is not an interview. Use your judgment of what flies and what doesn’t, e.g., you can even try an icebreaker if you’re sure it won’t come out as cringe.

The second important topic for your first session is to ask for expectations from your direct report. Ask them about what worked for them with previous managers and what hadn’t. Let them talk about how they see your role and how you can help them the best. Here’s an example set of questions for your first one-on-one:

  • How should we use these sessions together?
  • What are your expectations towards your managers?
  • What worked well with your past managers?
  • What didn’t work well?
  • What are some things I should never miss doing?
  • What are some things I should never do?

The second one-on-one – the state of affairs

state of affairs

The second one-on-one – the state of affairs

Use your second session with your new direct report for a deep-dive on how they think things are going in the team, in the org and in the company. This, done well, can become a treasure trove for you as a manager. You’ll hear useful information about the following (and potentially more):

  1. What’s important for your engineer
  2. What’s going well in the team
  3. What’s going well in the organization
  4. What are some troubles in the team
  5. What are some troubles in the organization

Do this with each of your direct reports (and peers/supervisors!) so you can identify patters and weigh topics.

Here’s the set of questions I use (parts shamelessly stolen from other leaders):

  • What has been going well so far?
  • What has been frustrating?
  • What impediments do you have to doing your job?
  • Where is the greatest friction in delivery right now?
  • Are there active conflicts going on?
  • How do you feel about the organizational structure we work in?
  • How often is progress hanging on decisions outside the team?
  • Do you feel like you’ve been learning on the job?
  • Is there training you wish you had?
  • If you had a magic wand and could change one thing only, what would it be?
  • What would you most like to accomplish at this company? What are your personal goals for your time here?
  • What are the things you are hoping I don’t change?
  • What are the things you secretly hope I do change?
  • What are the good things about this organization we should build on?
  • If you were me, what would you do first?
  • Why isn’t the organization doing better?
  • What will be our greatest challenge?
  • What is the best thing I can do for you?

The third one-on-one – the career check-in

career check in
The third one-on-one – the career check-in

During your third session, it’s time to see where your direct report is in terms of their career – in general in their journey and as well in a more concrete way in the company and in their current role. Meeting them only the third time might feel a bit early to talk about career, but trust me on this. You want to start the discussion as early as you can for two reasons: first, it will always take more time to turn this into an actionable discussion than you’d be comfortable with, and second, you need to communicate early that your engineers’ growth is a priority for you.

The outcome of this discussion – or rather, these discussions, as it will surely take more than one session. This is to understand your engineer’s career journey in past jobs, in the current job, to learn about their aspirations (or the lack of it!). You’ll also have a first shot at seeing whether their current setup is supporting them in reaching their career goals. It’ll give you future career talks and goal setting a good foundation. After this, you can start thinking about what opportunities, guidance, coaching and training they need.

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