One on ones — 7 top tips

Chris Poel
River Island Tech
Published in
4 min readSep 30, 2021

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A number of us have one-on-ones that could be better. Should be better. Will be better! But before we get into it, you have to first understand a few dirty secrets about 1–2–1s:

Photo by Jopwell from Pexels
  1. Your report must understand your motivations and values in order that they’re able to feel safe when raising topics with you. This is about relationship building after all. Therefore, if you haven’t got a shared vision with your report, your 1–2–1s aren’t going to be very effective. Good people follow vision not words. If you don’t provide a strong, engaging vision reports are going to be in the personal survival mode of ‘us vs them’, ‘me vs you’, paper-trail ass covering politics.
  2. One on ones should be scheduled because that makes them a real actionable thing in the weekly calendar that your reports can easily nag you about when you have clashes. You will have clashes, so if your reports don’t nag you your relationship with them sucks. If you hired them well, you should hired someone better than you, so what are you doing wrong?

OK, and so those are 2 free tips. Now onto what I wanted to say, and what I cover in the crib sheet I myself use for my one on ones:

Set an agenda

This is a business meeting, not a jolly, so as with all business meetings, set an agenda. Set this agenda:

  • The 1st third is for them to talk about whatever they like. Let them know they can talk about whatever they like. You get to talk about whatever you like next, but right now you want to build a relationship, so let your report be your report. Take notes.
  • The 2nd third is for you, so ask the burning questions you‘ve wanted to ask for the past couple of days at this point, not before. Not before. This is not your meeting.
  • The 3rd third is for you both to talk about the future (hopes and truths).

Ignore the agenda (for a while at least)

If your reports take over the whole meeting, let them. If you have reports talking too much it’s probable that you don’t actively listen. Start actively listening. If the report continues to talk through the entire agenda week on week maybe it’s them. Coach them by telling them “Hey, next time, so I can get some stuff from you in these meetings would you mind if we watch the clock and get a little closer to the agenda?”.
Let’s be honest though, you can ask them about stuff at any time, right? How often do your reports get to do the same with you, without being made to (or just) feeling uncomfortable about doing so?

Write notes during or immediately after each 1–2–1s

Look for patterns and breaks in patterns: for example ask the same opening question with the same energy with every time, log the reply every time, and you’ll be able to spot outliers. You can’t standardise the entire 1–2–1, but you can have the same opening. It gets the meeting started, takes the pressure off you, stops you from ever kicking off the meeting on a tactical footing. It starts every 1–2–1 about the direct, rather than you. Pick one and use it forever:

  • “How’s it going”
    If the response you logged was “great” 9 times, and then the 10th entry says “alright”, you‘ll spot it’
  • “How are you, today”
  • “How are things?”
  • “What’s going on?”

Write down the topics your report raises to you

Look at their list and diff it against the list of topics you want/expect them to focus on.
Q. Are the topics they raise demonstrating that they’re at the right (high/low) level? Are you setting them straight?
Q. Are they spending their time where you want them to? Are you setting them straight?

Actively listen

Don’t be listening out for problems to solve, people that do that see problems everywhere. Instead, in this meeting see the potential for a good conversation, first lead by them, then by you. Remember, this is a relationship building business meeting; everything you need to know will be within or between the words your report provides to you, so actively listen.

In the first third of the meeting consider yourself as a humble, encouraging sounding board. Bear in mind that in order to think one must often talk. This is why freedom of speech and language is so important: it’s only with these freedoms that your reports are able to think through their thoughts.

So, just as you’d tell a junior engineer not to immediately look for the root cause of a problem before exploring all the data, so too should you not treat your report’s first statement as the end of a conversation, to which the root cause must immediately be sought. A person’s first thought is the beginning of the good conversation you want to achieve.

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Chris Poel
River Island Tech

After a life of startups, and then financial services (to prove he could play ‘grown-ups’), Chris is now Head of Development at River Island