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.

The anatomy of a mistake and the response

I made a mistake today.

We love biking outdoors and take our bikes on a bike rack. I’ve done this many times over the past couple of years with no issues.

Today, I wanted to take 3 out of the 4 bikes for a tune up. Out of habit, I put the 4th bike in as well. It is newer and didn’t need a tune up. So I did find myself wondering why I was doing it. I ignored that impulse and put it on the rack.

Except I didn’t. I fastened the back wheel but didn’t fasten the front. A complete miss.

As we started driving, I noticed the bike jump as we went on a speed bump near our place. My instinct was to stop the car and check. But this had happened before and we were going to stop in 5 minutes anyway. So I ignored that instinct. A miss.

It ended up falling off the stand somewhere on the way and we ended up with damaged brakes and a flat tire. On a new bike that didn’t need to be on the journey.

An unnecessary mistake that was both expensive and stupid.

A few reflections –

(1) I start by being harsh (terming these kinds of mistakes stupid/moronic) and then remind myself to be kind. I find this middle path to be productive as it channels the emotion from the harshness into a constructive, forward looking, learning.

(2) Listen to your instincts. Especially in situations where we’re better safe than sorry.

(3) It is so much easier to break stuff vs. build.

(4) It could definitely been much worse. If this had been an adult bike, the damage could have been a lot more. Similarly, if the frame was affected, the bike would have been irreparable.

(5) Consciousness and focus in our daily activities matter. It helps to be present.

(6) It is a huge consolation that it is a problem that can be solved with money vs. a health problem for example.

(7) There’s a very positive philosophical idea that any bad thing that happens just helps prevent something worse. :-) It helps ensure I’m internalizing the learning and moving on with that tinge of positivity.

(8) There’s so much to learn from our experiences in life. Reflecting on a mistake like this one never fails to drive that home.

The S&P 500 – shifting horizons

The S&P 500 index 5 day view shows 3% decline and a bunch of volatility.

The 6 month view shows a ~17% decline along with more volatility.

The 5 year view shows a 61% gain and a clear march to recent highs with a few visible blips along the way.

The 20 year view puts all the above blips in perspective.

A couple of life lessons.

What feels like a big problem to us today is likely not a big deal in the grand scheme of things.

It is hard to judge progress over short intervals.

Zooming out often puts things in perspective.

Ups and downs are an integral part of this life – in our days, weeks, and even in the stock market. Keep calm and carry on.

15 minutes for a quick chat?

I’ve realized over the years that a message along the lines of – “got 15 minutes for a quick chat?” – that feels even a touch out-of-the-blue from a colleague means –

(a) They’re leaving the company (or in a rare case have a very good offer) (60%)

(b) They’re becoming a parent and going on mat/pat leave (30%)

(c) Other – e.g., they were annoyed by something did or need quick help with something personal (10%)

Number translations

I shared a note yesterday from “Making Numbers Count” by Chip Heath and Karla Starr that helped demonstrate that we don’t have an intuitive understanding of big numbers. The example – a million seconds is 12 days from now, a billion seconds however is 32 years from now – definitely helps make that point.

The key takeaway they keep driving home in the book is that the path to making numbers count is to “translate” them to ideas that are easier to understand. Here are a few that resonated with me.

The fastest human, Usain Bolt, would be beaten in a 100m dash by a Rhino by 2s and would be close to a Chimpanzee. he wouldn’t be close to a Cheetah or an Ostrich.

If cows were a country, they’d be #4 in Carbon emissions. They emit more than Saudi Arabia or Australia.

Apple market cap wealth is greater than 150 out of 171 countries. (or at least was – until recently :-))

If California were a country, it’s GDP would be more than all but 5 countries in the world.

Six sigma is 3.4 defects per millions. That means baking 2 decent chocolate chip cookies every day and going 37 years before baking one without a defect.

If everyone ate as much meat as a person in America, we would need to use every bit of land on the planet and add an extra Africa and Australia to meet the demand 

Imagine your (US) tax payment is visualized as employment over the course of a year. It would mean working 2 weeks for social security, 2 weeks for Medicare and Medicaid, 5 days on national debt, 1.5 weeks for Defence, then most of the rest of the year would be government payroll, 6 hours for “SNAP” (Nutrition assistance), 12 minutes to National Parks, and 2 mins to NASA.

Translations make abstract numbers accessible.

Million seconds, billion seconds

A million seconds is 12 days from now.

A billion seconds?

32 years.

That difference surprised me as it wasn’t what I expected. A billion is significantly bigger than I had imagined.

Chip Heath and Karla Starr use this example in “Making Numbers Count” to drive home the point that we don’t have an intuitive understanding of big numbers. The implication is that we need to make the effort to always put numbers in context for the people we’re presenting to.

It is a point well made.

Investing truisms

Amidst the ongoing market meltdown, there were some emotional stories shared in the Reddit among investors in the ill-fated terraUSD Stablecoin. Many talked about losing significant amounts – including house down payments and life savings. Some threads speak of folks contemplating suicide.

Reading the thread reminded me of two investing truisms. The first is that everybody looks like a genius in a bull market. When the tide is in, we don’t have to paddle.

And the second is that we can afford to not be great at investing. But it is very costly to be bad at it.

A good reminder to all of us to stay safe out there.

Integrity and momentum

Our integrity is our ability to make and keep commitments.

The fascinating thing about integrity is the way it accelerates the good and the bad. If we keep one commitment, we feel the momentum to keep the next. And the next. Until it becomes unthinkable to break a commitment.

And vice versa.

The implication is that the simplest way to build our integrity is to keep a small commitment – e.g., I will sleep 7 hours today. The momentum from that will build onto bigger commitments – e.g., I will do a strength workout every weekday – before we know it.

The related opposite implication is that we ought to be very careful about making exceptions on our values/principles. As the late Clay Christensen put it beautifully, we’ll all discover before long that life is an unending stream of extenuating circumstances.