When We Stop Talking About The Same Thing
There’s a particular kind of discomfort that happens in the middle of a conversation when you suddenly realize you and the other person hasn’t been talking about the same thing at all, maybe for minutes, maybe for days. You’ve been using the same words, nodding at the same moments, but meaning completely different things.
In social conversation, this is awkward. In a founding team, it’s existential.
Sensemaking as Survival Skill
Sensemaking is the process through which people give meaning to ambiguous situations, and it’s fundamentally social. We don’t figure out what things mean in isolation, we figure it out together, through conversation and shared interpretation.
For established organizations with stable routines, a lot of this has already been done. There’s institutional memory, shared frameworks, established ways of interpreting what’s happening. New situations get sorted into familiar categories.
But startups are operating in genuine, absolute ambiguity. Customer feedback is usually mixed, so does that mean the product is wrong or the positioning is off or you’re talking to the wrong customers? When a partnership conversation slows down, is it just because enterprise sales cycles are long or because the value proposition is not landing as it should? When someone quits, is it due to the normal chaos of startup life or because the culture is problematic?
There’s no objective answer to any of these questions (and to most questions in early-stage ventures). The answer emerges through collective interpretation. Your team looks at the same messy reality and together constructs a story about what it means and what you should do about it.
When this process works, it’s extraordinary. You develop a collective mind, the capacity to interpret situations similarly, because you’ve built shared interpretive frameworks through practice. When sensemaking works well, you can move fast because your team is roughly aligned on what signals mean.
But when it breaks down, it’s catastrophic in a very specific way.
Dying by Interpretive Drift
When interpretations start drifting away, the process is quite subtle, especially because nobody wakes up decided to interpret reality differently from their colleagues. It happens gradually, through a thousand tiny divergences that compound.
Each of you have a conversation with a different early customer, a different advisor, a different investor, or a different partner. Every time you tell your story to to your team, you emphasize different aspects of what made sense to you. Over time, you and your co-founders develop slightly different mental models of who the customer is, what the product should be, and how to get there. You internalized different narratives about what kind of company you should be building.
The gap widens so slowly you don’t feel it, until one day you’re in a strategy meeting and realize you have fundamentally different views of what the company is trying to do. The shared reality you thought you were building together turns out to have been two separate realities running in parallel, occasionally synchronized but increasingly divergent.
What We Lose When We Stop Making Sense Together
If interpretive drift is hard to spot, lack of coordination is not, and it is a clear sign of broken sensemaking. You can’t coordinate action if you’re not aligned on what the action is for. Someone builds a feature that makes sense for their interpretation of the customer; someone else is confused why we’re prioritizing that when what we really need is (their interpretation). It's not a matter of working harder, because both are doing their best based on their understanding, but what they are doing is pointing to slightly different directions.
Decision-making also gets harder where there is not cohesive sensemaking. Strategic choice become a battle because you’re not just disagreeing about the decision, you’re also disagreeing about the framing, the criteria, what even counts as success. These aren’t debates that can be resolved through data or discussion because you’re not actually in the same conversation.
Eventually, trust breaks downs as well, because when someone makes a decision that seems obviously wrong to you, it’s hard not to question their judgment. When your carefully reasoned argument seems to miss the point entirely for them, it’s hard not to feel dismissed or misunderstood. Neither person is trying to be difficult, you’re just living in slightly different realities.
This is dangerous because it compounds, and the less aligned your sensemaking becomes, the harder it is to become coordinated again. The less trust you have, the less willing you are to surface the interpretive differences that might let you realize what is actually happening.
The Labor of Collective Sensemaking
So what does it look like when teams do this well?
They develop practices that force alignment.
They have recurring conversations where they step back from execution and explicitly talk about interpretation. “What are we learning from these customer conversations?” Not just sharing data, but comparing how they’re making sense of it. “What did that investor feedback mean?” Really checking if everybody is drawing the same conclusions.
A good way to check for divergences is creating documents like strategy plans, customer personas, OKRs, and vision boards, because you might think you agree until you try to write it down together and realize you mean different things with the same words.
To build collective sensemaking, sharing experiences instead of only dividing and conquering is important. While having different people talking to different customers is more efficient, you should occasionally go together to the same meeting, because shared observation creates shared interpretive raw material (sharing the summary made by your AI note-taker does not count).
Another good point of attention: vague language. Make a real effort to remove yourself from this territory and define what you mean by common terms such as “product-market fit", “success", “rapid growth", or “exit". Abstraction is where interpretive drift hides.
The Practice of Shared Attention
What I keep returning to: sensemaking is a practice of shared attention. Not just paying attention to the same things, but attending together, comparing what you’re seeing, building interpretive frameworks that let you mean roughly the same things by the same words.
It’s difficult work. It requires vulnerability, so you can admit when you’re uncertain, when your interpretation might be wrong, when you don’t understand what the other person means. It requires patience to slow down enough to actually check alignment instead of assuming it. And it requires trust, so you are able to believe the other person is trying to make sense together with you, not trying to win an argument or impose their reality.
But it’s also the work that makes organizing possible. Before you can build anything together, you have to construct some shared understanding of what you’re building and why. And you have to keep reconstructing it, because understanding isn’t stable, it evolves as you learn and act and encounter new information.
The company is what you make sense of together. When sensemaking breaks down, everything else follows. The shared reality is the organization.
That’s the work. Not glamorous, barely visible, but essential in a way that nothing else is.