In any training there is always that one amazing point that you take from it that blows your mind…

Why have I not been doing this for years?

It was right in front of me all along.

That makes total and complete sense.

For me, this was years ago when I had just become a Software Manager and the suggestion that I have One on One meetings with my team every month to see how things were going.


But there it was, the replacement for quarterly reviews that would across as a surprise, the time to have each member of the team individually vent to me while I suggested ways to help them and/or took those concerns higher up the line.

I quickly learned what made a One on One very useful…

  • Don’t do it in a formal setting – most times I would go for a walk to a coffee shop with people or just around the building so we could get some air and separate from the office – if the mood was tense, this helped break things up
  • Write it down… later – You have a brain, use it, after each review block off some time so you can write down what was just discussed, but don’t do it while with them – this allows for the mood to be free-flowing and not formal
  • It’s not about the work – it’s about the individual, what’s on them, where are they struggling, where do you see them needing to focus more – avoid getting into releases and deliverables and instead talk about their work as it relates to a piece of the project – “What you are working on is going to x value to the end product”

In it’s most simplest terms, the One on One is about them, not you and this is where it becomes a little trickier because you are doing way more listening then you (me) are probably use to.  Over time the goal should be to add small probing questions and save your answers (yes at sometimes long-winded) for follow-ups with the individual.

Some Questions I like to pose during One on Ones;

  • What are you currently doing?
  • Is that what you want to be doing?
  • Is that work challenging you?
  • How can I help you get to where you want to be?
  • What can I do more/less of to support you?

Nothing mind blowing there, but definitely enough to open the doors to communication and discussion.  You might find when you start having a One On One that some people are reserved in their communication and it could take between 3 – 4 months for them to open up, but the more you do it, the more they will talk and that’s what you want.

The other bonus piece to One on Ones is that they are a good indicator to how far you are scaling towards as an individual to your team.  If you have a team of 20, you are close to blocking off a week a month to have these conversations with your team.  This isn’t bad, but in my very humble opinion, that might cause some extra stress on you as you to try to find that extra time somewhere else and you start to push through your One on Ones at a quicker pace to get back your time.  In that sense, they become an indicator that your team is growing too large and perhaps you can’t meet with everyone as you would like.  I’ve found over time that the perfect size to engage with people in One on Ones is somewhere to be between 5 – 10, it’s manageable, doable and not a scheduling nightmare on you or your team.  They can be a great signal to you in how you and/or your groups need to adapt to successfully keep moving forward.

As you  might have gathered, a One on One is not a Performance Review, those are different and should be treated very differently, the magic of the One on One is that it is not this, BUT it has the power to make those sessions a walk in the park when they do occur.

With that, I hope you take the time to have some One on Ones with your family this XMAS have a great holiday.


Want more? Check out my book Code Your Way Up – available as an eBook or Paperback on Amazon (CAN and US).  I’m also the co-host of the Remotely Prepared podcast.


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