Just as with a retrospective, your mentoring sessions and meetings will leave people more satisfied if you check-in with them first. If you allocate time to find out where people are coming from and consider how they like to learn, you’ll find that it benefits everyone in the room and lets your work relationships bloom.

I ran a rather unconventional session at conferences this year: A collaborative workshop that imparts kanban principles through building an assembly line to makes great tasting coffee - The Coffee Kanban Session (read more about it here).

In all of those workshops, there were plenty of people who have never used an AeroPress before but were eager to learn how to use it. I went ahead and showed it to them, but not without asking them about how they’d like to learn it first. This is just like how I collaborate whenever I’m mentoring someone in a workplace setting.


You’re in a situation where your goal is to share knowledge or facilitate decisions. You want to make the best out of the time ahead and are keen to know three things:

  • where people are coming from in terms of their prior experience
  • what their preferred style of learning is
  • and of course how they position their personal boundaries.


As a mentor and leader, it’s always worth understanding your colleagues as individuals, with their own aspirations and distinctive experience. Not taking the time to learn about both will leave you imposing your way of teaching onto them. In the long run, this would take away a valuable feedback channel for you, not just because you don’t evolve yourself, but also because your authority prevents someone from speaking their mind, especially if something doesn’t go as planned.


Before you start working with someone - in particular if it’s the first time, sit down with them and do a check-in. Ask them how they’d like to work and make sure to share your opinion too. Be careful with your authority, though. Always leave enough room for your counterpart to share their opinion as well. After all, as the saying goes:

“Everyone you meet knows something you don’t know but need to know. Learn from them.” 1

For example, if you’re about to start a Pair Programming session, make sure that both of you are aware of the different modes and choose one together!

We could do “Ping-Pong” pairing, where we switch every time we have a red test, or we could switch between Driving and Navigating every 15 minutes. What would you like to do?

In other situations, I noticed that a lot of the times I do a check-in with someone, their answer will fall into one of the following categories:

“Let’s take some time upfront to discuss”

☕ This means explaining everything about making a coffee with an AeroPress first.

I like this one because I myself appreciate knowing what’s about to happen. Preparing a meeting in this way will create greater alignment and helps making expectations transparent.

“Let’s just learn as we go”

☕ Get the filter paper, let’s make a mess and have some coffee!

This is how the meeting would probably happen without a check-in. I understand this as a sign that the other person is confident to raise questions while we’re working. In this case, I advise to always find room for a retrospective (remember, Everything Needs A Retrospective) so we can revisit our modus operandi.

“You do it and I’ll ask questions”

☕ Forget your muscle memory of making hundreds of coffees - explain as you go!

In my experience, this response can be an indicator for the person being a bit intimidated by the task or the overall situation. In a mentoring situation, I might inquire about their personal goal for the meeting. In any case, complying with this request means taking things slow and providing enough space for questions and for revisiting fundamentals.

Whatever they reply, make sure to keep it in mind and try to accommodate their wishes - it will make for a much better session. Also remember that this is a two-way-street: If you have a preferred way of going about things, it’s best if it’s shared with everyone else!

From the Toolbox is a compilation of small practices, tools and life-hacks I collected over the years.

  1. Attributed to several people, e.g. C.G. Jung or H. Jackson Brown Jr.