one on ones

The basics of one on one sessions

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It’s frustrating for many because this is one of the leadership areas where you don’t have a step-by-step guide, it takes a fairly long time to form a good one on one structure with each peer and by nature it’s dynamic – very different conversations will be necessary for different scenarios. My goal with this post is to write about my experience and my personal best practices that worked for me on both sides of this relationship – as an engineer and as an engineering manager. I’ll also mention some common pitfalls to avoid.

The purpose of one on one sessions

1:1s have many purposes, such as:

  • Building trust and rapport between you and your direct report
  • Depending on the efficiency of communication in the company, it’s a great time to discuss important changes, news, events AND get feedback on them. While you’ll do it with the whole team, 1:1s can have a different setting and your direct reports might be more open than in a group setting
  • Your direct reports getting feedback from you (e.g. it’s a bad idea in general (except for some rare cases) to give constructive criticism in a group setting). While hopefully you’re praising your peers in front of others, 1:1s are a great opportunity to repeat that praise, making it feel more personal
  • You getting feedback from your direct reports
  • Discussing your direct reports’ growth, setting goals and checkin in on them – while this might feel like reporting, 1:1s are actually a great fit for discussing personal goals
  • Showing that you care for your peers. Do ask them about their wellbeing in general. Show them you’re here to support them
  • Get aligned on topics such as (random examples, there are way more)
  • Company / team goals, mission, vision
  • Future of the team (hiring, etc.)
  • Engineers’ role in the hiring loop
  • Onboarding check-in for new hires
  • Share your mindset, way of thinking and let your peers challenge it

What to avoid:

  • Status report 1:1s – it’s very easy to fall into this habit because it’s natural due to the relationship between you and it’s a great time filler. It won’t serve the purposes of the 1:1s and most status updates are topics for the whole team anyway, not two people behind closed doors.
  • Mostly you driving the session – try to get your direct reports into the habit of ‘owning’ the 1:1s. It’s not easy but you can get there, e.g. nudge them to come with topics prepared. You can remind them 1-2 days before the session.

Who ‘owns’ one on one?

This is a tricky part – while the 1:1s are mainly for your direct reports you’re still accountable for making sure they get what they want (and need!) from it. What that means is that you’re not doing a great job here unless they feel it’s beneficial for them, that they can open up to you, ask help, give feedback, bring up sensitive problems. What makes the assessment really hard is that every person and situation is different (and chages over time!) – some peers will be naturally more open because of their nature and past experiences, others might need a lot of time to feel comfortable and trust you. The thing is, in all cases it’s your responsibility to do everything you can to make 1:1s a good experience for your direct reports. I admit it’s really hard or even impossible in some cases. Be prepared to fail a lot. Ask for feedback. Talk to other managers about it. Ask for advice. Use your own experience from ‘the other side of the table’.

What to avoid:

Blaming it on your direct reports – it might be nobody’s fault if someone won’t open up – or it might be yours. Don’t blame it on the other person who “didn’t even want to be there”. Remember, it’s primarily your job to make it work.

Skipping “cringy” one on ones – from time to time these sessions can get “weird”, you won’t feel much progress but keep having them, keep trying different approaches, different topics, different formats (meeting room vs. cafe vs. walking 1:1s vs lunch together, etc.)

Skipping the rapport building part of 1:1s – it’s easy to fall into the routine of a rigid, quick check-in with no real content and no trust-building, especially with peers you have a hard time getting close to. This is almost as if you’re not having the 1:1 in the first place. Prepare, bring different topics to the table, try, try, try.

Timing of one-on-ones

I’ve seen and tried different varieties of length and cadence of 1:1s, the common thing in all is predictable regularity. Currently I’m blocking a 1 hour session with all my engineers each week – same time & place for each. Your schedule might not allow such a setup, my advice is to prefer frequency over length (but of course a 1 minute checkin is not a 1:1), mainly because it supports building rapport and it gives you more flexibility – it’s better to skip a weekly 1:1 and still meet after 2 weeks than skipping a biweekly one and meeting after a month. Treat the blocked time as dynamic – it’s fine to finish earlier (sometimes much earlier) if you have nothing more to talk about.

What to avoid:

Regularly missing your 1:1s – it’s OK to skip or move around a few of these sessions but make sure you do your best to make it predictable and regular for your direct reports. If you don’t, you risk being seen as reliable and people might feel you’re not there when they need you.

Filling out the time just for the sake of keeping the length of the 1:1 – it’s perfectly fine to finish after 15 minutes. If you don’t have more topics (be sure to double-check though!) just let it go. It is to be expected anyway if you’re meeting frequently.

A list of random example topics for the one-on-one sessions

One on one topics

in no particular order

  • Feedback for the manager
  • Feedback for the direct report
  • Setting personal developmental goals
  • Checking in on progress towards goals and the validity/priority of the goals (do they still make sense?)
  • Highlighting opportunities to progress towards goals (e.g. “someone needs to figure out whether we should go with PostgreSQL or MySQL – does it sound interesting to you?”)
  • News from upper management (even if only reiterating on them)
  • Feedback/opinion on the news/changes from the previous topic
  • “Are you happy here? What could we do to make you happier?”
  • “What are the biggest roadblocks for you / for the team?”
  • “Does the company’s vision make sense to you?”
  • “What would you like to change in our 1:1s?”
  • “Is the company / your team / your role supporting you in reaching your goals?”
  • Hiring plans for the team / for the company / for the stack
  • “What do you think of how person X acted in that certain situation? Do you understand their reasons? If you didn’t like that, have you given them feedback?”
  • “How can I help you?”
  • “How do you think we are in terms of tech debt? Do you feel you are getting enough time and support to deal with it?
  • “You’ve been paged a lot lately, are you getting enough rest? Feel free to stay home tomorrow. Do we need to change anything in our on-call structure?”
  • “We’ll be starting a new project in about a month – I think you’d do a great job leading it, what do you think?”

Well, that’s it for an introduction to the topic, stay tuned to more specific tips and tricks in follow-up articles – in the meantime, this is an amazing article about one on ones if you’d like to read more.


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