Issue 86: I thought we had a deal.

ISSUE 86

27 MAY 2026 | READ ONLINE

Hi Reader,

I just booked a trip. Ten flights in total.

I know.

It probably took me fifteen hours (researching, comparing, rerouting, compromising on dates that neither of us loved) before I finally hit confirm. And somewhere in the middle of all of that, I realized something that should have been obvious from the start.

My husband and I had both agreed on the same trip. We did not want the same trip.

I wanted a beach. Preferably a yoga retreat. Preferably in Bali. He wanted to cycle. He wanted to be with friends. I wanted stillness. He wanted movement. I needed rest. He needed company.

We couldn't even align on dates. My calendar said one thing. His said something else. And for a while, the conversation kept circling back to the same impasse, restated in slightly different words, neither of us quite willing to let go of the version of the trip we had imagined.

We got there. It's booked. But it took more conversations than I expected, more compromises than I wanted, and a quiet decision on my part to let the Bali yoga retreat be an idea for another time.

Here's the thing I keep thinking about.

I thought we were aligned. We talked about the trip. We both said yes. I assumed that because we'd agreed to go somewhere, we'd agreed on what going somewhere meant.

We hadn't.

And this is not just a holiday story.

I've experienced versions of this in business, too. Situations where I was certain an agreement had been reached with a colleague, only to find them coming back and shifting the terms. Changing the scope. Moving the goalposts. Each time, genuinely surprised that I was surprised.

It took me a while to understand what was happening. For me, when I commit to something, that commitment is fixed. It's a promise. I will do the thing. For them, I think it was something more fluid. More of an intention, an idea, a direction. Not wrong, exactly. Just a different relationship with the word 'yes'.

Neither of us was lying. We were just working from different definitions of agreement.

Turns out, this is everywhere.

A January 2026 article in Harvard Business Review found that strategic misalignment is widespread and persistent in organizations, even when leadership teams believe they are fully aligned. The problem isn't usually dishonesty. It's that alignment is assumed rather than built. Leaders mistake the absence of disagreement for the presence of shared understanding.

A 2025 study published in Frontiers in Behavioral Economics explored why people keep (or break) their promises. The finding that caught my attention was that when responsibility for a broken commitment is undeniable, promise-keeping is high. But when people can find a plausible excuse that protects their self-image, a significant number will walk away from a commitment they genuinely made. Not out of malice. Out of the very human need to feel okay about themselves.

And a 2025 paper in Business Ethics: A European Review found that broken promises damage trust trajectories over time. The research showed that team trust climate can buffer some of the impact, but only if the relational foundation is already strong. Once trust starts to erode, it doesn't naturally restore itself.

In other words, the problem isn't always that someone lied. The problem is that alignment wasn't as robust as we thought, and commitment means different things to different people.

This doesn't make it less frustrating. I want to be clear about that.

When you've given your word and expect others to honor theirs, discovering they were working from a looser definition is genuinely hard. I struggle with it. The misalignment feels like a breach, even when no breach was intended.

But here's the reframe that's been helping me.

Assuming alignment isn't the same as creating it.

Most of us walk away from a conversation thinking we've landed somewhere, when actually we've only begun. Real alignment (the kind that's still there when things get hard or complicated) takes more than one conversation, more than a nodded yes, more than a shared calendar invite. It takes the less comfortable conversation about what we each actually mean.

A 2025 Springer Nature study on cognitive flexibility in leadership found that the ability to consider multiple perspectives and adjust your approach in response to new information is a distinguishing characteristic of effective leaders. Not rigidity disguised as integrity. Flexibility in service of what matters.

Letting go of Bali was not giving up on rest. It was choosing the relationship over the itinerary.

Sometimes, the most aligned thing you can do is revisit the question.

A Small Experiment for This Week

Option A: The alignment audit

Think of one relationship where you believe you're aligned. Then ask: when did you last actually test that assumption?

Have the two-minute conversation. Not "are we good?" but "what does good look like to you right now?" You might be more aligned than you think. Or you might catch a drift before it becomes a gap.

Option B: The definition check

Think of a recent agreement that felt solid to you but fuzzy in practice.

Ask yourself: What did I mean when I said yes? What might they have meant?

Not to assign blame. Just to understand. Because most misalignment isn't malicious. It's two people using the same word to mean different things, walking away certain they've agreed.

Naming the gap is the first step to closing it.

I'll let you know how the trip goes.