I was expecting it to be this way. But it wasn’t.
We’ve all said it. About a job we took that turned into something else entirely. A leader we believed in who disappointed us. A team member we invested in who didn’t deliver. A role we were promised that quietly became unrecognizable. A relationship we poured ourselves into that couldn’t hold the weight of everything we never said.
It is the human condition. We move toward things with a picture in our heads — of how it will feel, what it will look like, who we will be inside of it. And when reality doesn’t match the picture, we call it a disappointment. A betrayal. A failure.
But before we name it any of those things, we should ask the harder question.
Why were you expecting that?
Because most of the time the honest answer is uncomfortable. Nobody told you. You heard what you wanted to hear. You assumed they assumed. Everyone was so eager to get started that nobody stopped long enough to have the one conversation that would have made everything that followed make sense.
The expectation was never declared. So it was never confirmed. And the gap between what you pictured and what actually existed quietly became the distance between you and everything you were hoping for.
Before we arrived, the vineyard sent a questionnaire.
Did we want to simply enjoy the wine, or did we want the full education? The background of the owner, the winemaker, the vintage, the varietals. Were we students of the craft or were we there to relax?
We wanted all of it. And because they asked, they knew. The experience was exactly what we came for.
I was in Paso Robles with a friend who writes about wine for a living, and tasting rooms roll out the red carpet for people in the industry. I was a grateful beneficiary of that. But only one vineyard sent the questionnaire. The rest went through their scripts and adapted when they figured out who they were talking to. It wasn’t seamless. It wasn’t the same.
One question changed everything.
I keep thinking about how rare that was. And I keep thinking about what it costs when nobody asks.
Gallup reported that U.S. employee engagement fell to its lowest level in a decade in 2024 — only 31% of employees engaged, matching figures last seen in 2014. Globally, the numbers are worse. Engagement dropped to 21%, costing the world economy an estimated $438 billion in lost productivity. We talk about this as a culture problem, a compensation problem, a post-pandemic problem. We roll out initiatives and ping-pong tables and flexible Fridays.
But what if a significant piece of it is simpler and harder than any of that? What if much of that disengagement traces back to expectations that were never spoken — on either side of the desk?
Airbnb CEO Brian Chesky has been public about his leadership philosophy in a way most executives aren’t. He stays close to the work, involved in the details, not interested in handing off and stepping back. He’s told people straight out: if you want to be autonomous, start your own company. You can agree or disagree with that. But you cannot say you didn’t know what you were signing up for. He declared himself. Upfront. Without apology.
Most leaders don’t do that. They hire for skill and assume alignment. They onboard for process and assume culture will sort itself out. They manage in their heads and assume their people can read them.
They can’t.
A friend of mine owns a company and hired someone with the understanding that he would obtain the certification required for his role. He hasn’t. And now she can’t fire him because the expectation was never put in writing. He’s dead weight. She’s frustrated. And the whole situation could have been avoided with one direct conversation at the start.
Another friend was hired as a consultant. Weeks in, the company told him they wanted him to pivot to sales. He’s not a salesperson. It’s not his wheelhouse and it’s not what he signed up for. He quit. The company lost a good person over a conversation that should have happened before the offer letter was signed.
And then there’s the one I hear most often from employees after a keynote, when they pull me aside and drop their voice. They got their annual review and the negative feedback — the thing that’s now on record, the thing that affects their trajectory — was something nobody ever talked to them about. Expectations they didn’t know existed. Standards that were never communicated. We expect people to read our minds and then hold them accountable for failing to do so.
Gallup specifically flagged a decline in one of the most fundamental elements of engagement: clarity of expectations within a role. That’s not a ping-pong table problem. That’s a conversation problem.
The most disengaged employees I’ve ever encountered weren’t lazy. They were lost. They walked in the door with a version of the job in their head — what they’d be doing, how they’d be led, what success would look like — and nobody ever confirmed or challenged that picture. So they performed a version of themselves that didn’t quite fit, for a leader who never said who they actually were, inside an organization that assumed silence meant alignment.
It never does.
Before the declaration comes the excavation. Before you can set clear expectations with your team, you have to be honest with yourself about who you are as a leader. How you work. What you need. What you won’t tolerate. What success actually looks like in your organization — not the version in the handbook, but the real one.
And then you have to say it out loud. Before someone takes the job. Before the project starts. Before the review, not during it.
That vineyard asked one question and changed the entire experience.
What if you did the same?
