Why I Want My Team to Tear My Strategy Apart
The best product teams disagree. Here's how to make it safe to do so.
Last week, after a strategy meeting, someone on the team privately apologized for critiquing the work I prepared for the meeting. She felt like she was too blunt and perhaps critical of my work. I assured her she was exactly where I wanted her to be:
It was from that interaction that this Substack post was born…
Here’s what happened
I scheduled a strategy meeting last week with a plan I vetted thoroughly. I’m experimenting with evolving our product, and I had built the plan out in preparation for the meeting. The strategy, the sequencing, the rollout. I was ready to talk next steps and owners.
Instead, we spent 90% of the meeting unpacking my strategy.
Are we optimizing for the wrong thing?
How do we not burn our customers?
What exactly are we asking people to walk into, and are we being honest with them about it?
Every one of those questions poked a hole in assumptions I had made, mostly solo.
Younger me would have gotten defensive. She would have heard all of that as “your strategy is bad” - then "you are bad” - and spent the meeting defending the plan. I know this because I used to do exactly that. All. The. Time.
Older me has learned something different.
Dissent doesn’t mean your strategy is bad.
It means your strategy isn’t strong enough.
Yet.
The reality - in the workplace and in many relationships - is that agreement is comfortable. Because it can feel good. And often in the workplace, we treat perfect agreement like it’s the goal. Everyone nods, the meeting ends early, we all feel good. But teams that agree don’t produce the best work. They produce good enough results. And good enough results are a surefire way to build a product that doesn’t differentiate. It’s what kills a business, really.
The best ideas don’t come from building alone. And they definitely don’t come from a room where no one is willing to push.
My take: It is lazy to agree. It is competitive and excellent to dissent.
One of my teammates said it perfectly: “Our strategy is sound. I just want us to poke holes, not to derail us, but so that first message lands.” That is the whole point. She wasn’t tearing down the direction. She was making it strong enough to survive contact with real customers.
By the end, I wasn’t deflated. I had clearer next steps. Every dissenting opinion had turned into a named non-goal or a risk we now knew to prepare for going in. I left with a better plan than the one I walked in with, precisely because no one let me keep the one I walked in with.
How to dissent
A team doesn’t magically become one that welcomes dissent. You have to build the muscle, and you have to make it safe to invite dissent.
Model It
Radical candor gets a bad rap. But, it’s useful. And, one of the most effective ways I’ve taught dissent is by modeling it as a leader. Take my counterpart and I at Hampton. We are the dearest of friends and also go toe-to-toe regularly, disagreeing and challenging each other in front of our teams. It might even be uncomfortable to watch. But, we don’t do this for sport. We do this because we both care deeply and want to get to the best outcomes possible. Often we’ll come to a disagree and commit moment, which helps us move quickly not for the sake of it but to learn faster.
As a leader, demonstrating the type of behavior that you want to see from your team is step one.
Pre-empt it.
One of the most powerful tools I’ve used in years of product development is a pre-mortem.
A pre-mortem is an exercise where a team imagines that a project or initiative has completely failed, and then works backward to identify the causes of that failure.
How does it work?
Before we commit to a plan, we imagine it’s six months later and the whole thing failed. We outline all the reasons it failed.
Then we work backward: why did it fail? What did we miss?
Instead of defending the plan, everyone is suddenly motivated to find its weak spots, because naming the failure is the game.
It turns this is a great idea into here are the five ways this could fall apart and here’s what we’ll do about each one.
The dissent stops feeling like a personal attack and starts feeling like insurance.
Reflect on it.
No one is a bigger champion than me for a team retrospective. Two things we do at Hampton that amp up the candor on retrospectives are meeting ratings and a Hampton exercise I conceived of called, The Gap.
Meeting ratings
This we borrow from EOS. At the end of a meeting, all participants rate the meeting on a scale of 1-10. It sounds almost too simple. But its something I’ve never done before. In real time, if forces everyone to be real and reflect on what’s working and what’s not. It looks something like this:
The exercise forces us to think about how to do better in the moment. Real time feedback is the best kind of feedback. It invites candor and ensures that everyone has a low-stakes way to signal something was off. Further, it holds all of us accountable for making the time worth it. Meetings are expensive. So they better be worth it.
Related: The art of an inexpensive meeting
The Gap
Last year, we introduced a reflection exercise at the end of every Core Group meeting called The Gap. The best groups run it comprehensively at the end of every meeting.
How it works: Members go around the room and each person answers one question in a single sentence: Did this session reach its highest level, and if not, what was the gap?
No fixing. No defending. No debating. Just one honest observation, said out loud, before anyone leaves the room.
Our strongest groups can say uncomfortable things to one another like: I feel like you steamrolled me today or I didn’t feel like I got answers to my problem or even, I didn’t like how you moderated the meeting today. Members who use this tool know that real time feedback help the space get stronger so that these sessions are valuable. These are busy founders after all.
Without The Gap, problems in a group stay invisible until they become crises. The members who feel unheard say nothing, and the sessions that stayed surface-level are good enough because no one named what was missing. The Gap makes naming conflict or dissent the norm. And it makes the best groups even stronger. Because, dissent isn’t bad. Like I said before:
It is lazy to not say anything. It is competitive and excellent to dissent.
All of these tools do the same thing underneath. They make candor the expectation, not the exception. They normalize directness so that it’s not about protecting feelings. It’s about protecting the customer experience.
Importantly this all works when and only when dissent is delivered with respect.
When I look at my strategic plan from last week, I still love the plan I walked in with. But, I love the plan I walked out with more.
We don’t build great things alone. We build great things together, will differing ideas and opinions.
The next time your team nods along and the meeting ends early, don’t celebrate.
Invite a challenge and see how your projects get even better.
I’m Jori Bell, VP of Core at Hampton. I’m also a Coach for Product Leaders. If you’re working on building a team that tells you the truth, I’d love to hear from you.