One of the most frustrating dynamics I see in leadership is the slow, silent build of tension that comes from miscommunication. The leader thinks they’ve been clear. The team member thinks they’re doing what was asked. But something’s misaligned, and it shows up in delays, missed expectations, or that subtle but unmistakable sense of disappointment.
It’s easy to write these moments off as personality clashes or performance issues. But more often than not, what’s really happening is a breakdown in communication that started with the best intentions. A leader wanted to keep things positive. A conversation felt too awkward to fully finish. So they softened the edges, hoping the message would still land.
This is how we end up choosing agreeableness over clarity.
And then, when things don’t go the way we imagined, we’re confused. Or worse, resentful.
But clarity doesn’t have to mean conflict. Being honest and direct isn’t the same thing as being harsh. In fact, if you’re trying to build a culture of accountability and growth, clarity is one of the kindest things you can offer.
Jerry Colonna, the author of Reboot (how many of you have heard me rave about this book??), offers a set of questions I come back to often when working through these kinds of breakdowns. They’re deceptively simple, and incredibly useful if you’re willing to answer them honestly:
- What am I not saying that needs to be said?
- What am I saying that’s not being heard?
- What’s being said that I’m not hearing?
These three questions cover almost every direction a communication breakdown can take. They help us spot the places where we’ve avoided being honest. Where we’ve overestimated how clearly we communicated. Or where we’ve stopped listening altogether.
Claire Hughes Johnson, the former COO of Stripe, offers a related reminder: “Make the implicit explicit.” Don’t assume people know what you mean. Don’t assume they understand your tone, your timeline, or your definition of success. Spell it out. Say it clearly. And don’t wait until a problem arises to make the expectations visible.
This doesn’t mean micromanaging or turning every conversation into a checklist. It just means you stop expecting people to read between the lines — especially when the cost of a misunderstanding is high.
When I work with clients who feel like they’re saying the same thing over and over without results, I often give them this framework to work from. It’s not elegant, but it’s effective:
Clear expectations + honest feedback + reciprocal curiosity = communication that actually works.
Start by asking whether the expectations were ever clearly stated in the first place. Not just vaguely mentioned in a meeting or implied in a task, but clearly outlined, with timing, quality standards, and measurable outcomes.
Then look at the feedback. Are you sharing it while it’s still useful? Or are you waiting until the issue is big enough to justify the discomfort of having the conversation?
And finally, consider whether you’re listening with the same energy you’re expecting from others. Are you open to the possibility that something important is being said…even if you don’t want to hear it?
Clear communication isn’t just about talking. It’s about making sure the message was understood, acted on, and aligned with reality on both sides.
Being agreeable might keep the peace in the moment, but it usually creates more confusion and resentment over time. Being clear might feel uncomfortable upfront, but it’s what allows trust and progress to actually grow.
So if something’s not landing — if the results aren’t matching your words — start by asking the hard questions. And then commit to saying the thing that needs to be said, in a way that leaves no one guessing.