Today, I’d like to talk about a practice I introduced to the people I managed just a few weeks after joining Shipup. I didn’t know it would turn out to be something so useful.

The idea is pretty simple actually: Your direct report sends you something they consider worth sharing with you (can be a blog post, book chapter, video, podcast, …) and a few related questions they have in mind a few days before you meet together. On the D day, you share your opinion about it and try to answer the questions that go with it.

For the session after, you switch roles: You choose the resource & questions and your report will be in charge of expressing their opinion about them.

The context

Before going into more details, let me rewind a little bit. Eight months ago, I joined Shipup as the VP of Engineering. As you can probably guess, one of the key things for me was to create a strong relationship between me and the people I manage.

We had of course several touchpoints during the first weeks: introduction sessions, onboarding sessions, and various operational work syncs. Additionally, I quickly took over the biweekly 1:1 meetings that our CTO was doing previously.

However, I felt quickly it was not enough to know each other on a deeper level: the way we each think, what we value, what are the experiences we’ve gone through, etc… I know these things take time, and I’m a rather patient person, but I was convinced that it would be beneficial to accelerate these learnings.

So I started to think about it with a specific framing in mind: It shouldn’t cost too much time (calendars are always quite full the first few weeks), it should remain informal (should be an open discussion: no judgment, no objectives, etc.), with the idea of getting to know each other on a deeper level.

The practice in details

So I came up with the idea of discussing a topic, free choice but still work-related with the starting point being something that you recently came across and found interesting to share.

It was partially influenced by a previous experiment I tried during the lockdown, which was inspired by this learning practice session: https://philippe.bourgau.net/growth-mindset-coaching-turn-remote-work-commutes-into-team-learning/

I’ve ended up with this format:

• Frequency: Bi-weekly, alternating roles each session
• Duration: 30 minutes, no more
• Location: Office or remote. Both work well and I think it’s a good opportunity for remote sessions
• Preparation: The resource has to be sent at least a few days before in order to have time to think about it (we store the resource link and the questions on a Notion page)
• Any topic you find interesting

Here are two examples I took from our archives to illustrate the practice in a more concrete way:

Example 1:

• Direction: Manager → Report
• Related questions:
  ⇒ Do you think this model is useful?
  ⇒ Would you add something to the pyramid? A new layer, a new check?
  ⇒ What are the things we don’t check enough IYO?

Example 2:

• Direction: Report → Manager
• Related questions:
  ⇒ We’ve been introducing new processes and also updating existing processes: how do we make sure there isn’t a feeling of “too much, too soon”?
  ⇒ It seems like we do most of the things mentioned in the article except the testing step and instead opt for a do it and refine; do you think some of the processes we’ve updated or added could have benefited from a testing phase?

The benefits

After a few dozen of sessions, it turns out that this practice not only reach the initial objective but brought other benefits, some of which I was not really expecting.

Sharing related experiences

Stating the obvious here, one of the values of hiring an engineering leader is bringing their experience to the company. Some of these past experiences could help to either improve something in the company or avoid big mistakes. There were a few sessions where the topic of the day reminded me of something I’ve seen or experienced in the past and it was often interesting discussing it and explaining the positive and/or negative sides of it.

Forcing yourself to know more about a topic

One of the advantages of sharing the topic & questions in advance is having time to read it, of course, but also to think about it. A few times, I’ve realized that for some topics, my mind was not as clear about it as I thought. When this is happening, it’s best to put your ideas in order and dig deeper into the topic to come up with a clear opinion on it. That feeling of needing to master a subject is something I had already encountered when teaching a specific topic or preparing for an interview, and I find it interesting to have the need to feel this once again in a new way.

Bringing interesting topics that wouldn’t surface otherwise

Usually, the topics you discuss in your reports are the “fresh” ones: The things that did or did not go well in the last sprint, the last production issues, the most recent individual or team victories…

I’m enjoying the fact that our sharing sessions bring out discussions that would otherwise not happen because no recent related events touched on that specific topic. This is clearly what I was looking for when introducing the practice, finding a way to broaden the discussions and make them happen earlier, rather than just waiting for them to magically appear.

Finding out what kind of topics resonate with everyone

I think my initial idea of alternating the role of the sharer and the opinion giver was to reinforce the informal side of the practice, putting the hierarchical relationship aside and trying to share equally. Now that I’m thinking again about it, the other benefit I see in the rotation is that it eases to find out what are the topics particularly resonate with everyone. All sessions are not equal, and it’s interesting to see which topics lead to powerful conversations, versus the topics that end with “well, interesting indeed, but not too much to say/do about it”. Having a top management role at Shipup, I imagine it would be quite hard to know what caught the eyes of your team without this practice.

Taking the pulse of a given topic

It’s always surprising to see that some of the practices and ideas I had difficulty implementing or conveying in past experiences were easy to do in a new environment, and conversely things that I’ve initially considered as quick wins were in fact much more difficult to implement. Even though the practice of sharing ideas is not targeted for this end, I’ve used it sometimes to take the pulse of a process improvement, a practice, a principle, or whatever idea I felt wouldn’t be easy to bring. Starting to discuss it in an informal way, with open questions has helped me to evaluate my current feelings, see what precautions to take, or just to plant a seed and see how it grows 🌱

Finding coaching opportunities

Even though it didn’t happen much during our sessions, I guess it’s pretty easy to imagine a discussion leading to a coaching opportunity. A question you asked didn’t have a clear answer or didn’t have any experience could lead to an ad-hoc coaching session when you particularly focus on a topic.

Reinforcing a culture of learning & sharing

Even if it was not an explicit “rule“ when introducing the practice, most of the resources we select come from the reading habits we’ve developed. Learning & sharing is a pillar of our engineering culture, everyone on the team has allocated time for that, and this practice is another way to reinforce that culture.

Works particularly well in a remote context

It can be hard to get the same value for a specific practice depending on if it’s done in the office or remotely. As the practice doesn’t require specific tooling and is basically a discussion, doing it remotely is particularly suited. You often see blog posts advocating for creating a virtual water cooler or any other idea to re-create informal discussions or build relationships in a remote environment, which makes this one a good candidate as well.

How long will it last?

I was not initially sure how useful the practice would be and after a few dozens of sessions, it looks like the value we get from these sessions is still high.

The fact that the content is shared in advance, people are prepared, and actively try to replan sessions (rather than canceling) says a lot. The sessions are always enjoyable and there is a sense of serendipity happening that is interesting to live.

The good thing is that, even if it started just between myself and the team’s managers, the practice could be done between any level of employee.