Facilitating team events – feat. icebergs, smiles, tears, and intensity

A note for new subscribers: This post is part of a series on my notes on technology product management (this is what I do for a living). You might notice that these posts often link to older posts in the series on LinkedIn even though they are all available on this blog. That is intended for folks who only want to follow future product management related posts. Finally, for all those of you who don’t build tech products for a living, I believe many of these notes have broader applicability. And I hope you find that to be the case as well…


A quick overview of what we’ve covered on “Notes on Product Management” so far – 


A healthy product team has 3 elements that come together – context, communication, and trust. Communication is the lifeblood of this trifecta as it helps both establish and maintain context and trust.

The more the trust and the context, the lesser we need to communicate. But, given how often we have turnover in teams, it is a good rule to default to over-communication to ensure shared context and trust.

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While shared context – powered by good communication – is best done consistently in the office and help maintain trust, they rarely help accelerate the building of trust. Intense experiences do that. And while teams go through intense experiences from time to time when they’re in the trenches, these are the exceptions that prove the rule.

My belief is that in-person team events outside the office are the most powerful way to accelerate the process of building trust. As a result, I think these events shouldn’t spend a lot of time attempting to converge on strategy or roadmaps. Those context-building activities can be done in the office with a good meeting. It is worth inserting activities that encourage divergent thinking – e.g., a brainstorm – on the agenda to get juices flowing. But, for teams that don’t operate with high levels of trust, I think the sole focus of team events should be to build trust.

How do you know if your team operates with high levels of trust? I don’t think there is an easy metric to measure this. Employee feedback/voice surveys can point to it. My experience is that this is in the category of “you just know.” It is easy for folks on the team to be honest about what they’re struggling with, conversations about scope flow easily, and so on. If you are operating with high levels of trust, you feel it.

With that said, there are 2 kinds of team events – those that go above the iceberg and those that go below the iceberg.

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I. Above the iceberg – fun but don’t do a great job building trust

The purpose of “above the iceberg” events is for the team to spend time together outside the office. 

What’s great: Helpful first activity for a new team or a large group to break the ice, easy to organize as there are so many places you can go to.

What’s not great: They don’t accelerate trust or deep bonds. 

What they require: Light prep and cash/a decent budget. :-)

 How to prepare – 2 ingredients of good “Above the iceberg” events:

(1) Moderately intense activity: Good activities often involve some form of lightweight competition.

(2) Space to talk: This can either be during or after the activity

There are a whole host of activities that do a good job here – bowling, bocce ball, a good dinner, picnic, mini golf, hikes, and so on. These activities combine a moderately intense activity with space to talk.  

Other activities dial up the intensity – e.g., go-karting, laser tag, escape rooms, fencing, virtual reality game – and need to be complemented with a nice lunch or a lightweight activity elsewhere to enable conversation.

Such activities are needed from time to time – they just work much better for brand new teams or teams that already operate with high levels of trust. 

II. Below the iceberg – these build trust by facilitating meaningful conversations

Most teams end up organizing a series of “Above the iceberg” events when a “Below the iceberg” event is actually what they need. The purpose of these events is to facilitate conversation that enables the team to REALLY get to know each other. These go beyond surface introductions to help people understand what makes them tick.

As I’ve shared before, they accelerate the creation of trust – and in rare cases, mistrust. Either way, you’re going to see acceleration.

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What’s great: They do a fantastic job building trust.

What’s not great: They can be intense (which isn’t for everyone) and require significant preparation to ensure they’re hitting the right notes depending on the stage of the team.

What they require: A great location, vulnerability from the leader and facilitator (if they’re different people).

How to prepare – decide what kind of event you want: Below is a menu of example conversations that range from –

(a) Lightweight to intense: While lightweight events can be done in the office, the “great location” requirement still holds. These can’t be done well in the typical window-less conference room. You’ll need to either find an outdoor location or at least find a great room with a view where you can rearrange the furniture and ideally sit in a circle. 

The intensity mentioned here is emotional and not necessarily correlated with the preparation required. 

(b) Smiles to tears: Some types of conversations inspire smiles, others inspire tears. There’s no right answer here – you just have to pick based on your leadership style, the stage of the team, and so on. 

I’ve shared example conversations/activities in each box. This is not an exhaustive list by any means. Instead, they’re meant to illustrate various kinds of activities and conversations. Most great events involve getting to know what really drives others on the team and some form of sharing genuine appreciation.

Once again, there is no right way to do these – you just have to pick one that works based on what you’re going for.

The only truth is that the more the intensity and the tears, the deeper the bonds. :-)

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3 lessons I’ve learnt about these “below-the-iceberg” events over the years – 

(1) You set the tone. If you’re the facilitator, I can’t say this enough. The more intense the experience, the more vulnerable you have to be willing to be.

(2) Don’t enforce time for more intense activities. Great activities can sometimes take hours. Exercises that involve sharing gratitude nearly always go long. That’s okay.

For example, I’ve been part of an activity with a group of 15 folks that took 7 hours. Similarly, there was another with 7 folks that took us 3 hours. Everyone had something to say about every other person. It took time. But it was so memorable.

(3) The environment has to be just right. Location, mood, external stressors, and size of the group all contribute to the right environment. Sometimes, despite our best attempts, it doesn’t quite work. And in other times, everything just slides into place.

I was recently in an event where we didn’t plan for this sort of a conversation. It just clicked into gear around a fireplace – inspired by a great location, good food, and a good mood. When that happens, you just have to learn to recognize and go with it.

All this said, it is worth putting in the effort to create a great environment. Done right, the effect of such events on the relationships and trust within the team is magical.