It’s easy to think you’re being clear as the business grows and you hire more people, but a lot of the stuff still lives in your head and nobody else can see it.
I’ve been there, and it’s frustrating.
That’s why I asked executive coach and adviser Kathy Wu Brady to write about how to get aligned with your team and clear confusion before it turns into culture.
Kathy is a 2x CEO and COO, writes the Lead Without Limits newsletter, and works with leaders on fixing themselves before they start trying to fix everyone else. 👇🏻
Where confusion starts
When teams start missing things or doing work twice, the problem often starts earlier than you think.
The instruction sounded clear enough in the room. But once the work got moving, it turned out not to be clear at all.
That’s because capable people still need to know what’s actually being asked of them.
You thought you were clear
If you are a leader, especially early in your career, there is a bias a lot of organisations push on you: sound more confident than you feel.
I got that advice in my mid-twenties, just after stepping into my first executive role at a large media company.
My boss told me I would be more effective if I answered questions with more confidence and fewer caveats. What I heard was simple: stop sounding uncertain.
When I pushed back and said, what if I don’t know the answer, what if I’m not sure, he said to come off as sure. That’s what people expect.
What happens next is harder to notice. You get used to sounding certain, and after a while you stop checking whether people understood what you meant in the way you thought they would.
That’s where the question starts to matter. Instead of asking yourself whether you said it clearly, ask what the other person actually heard.
The team fills in the gaps
This problem doesn’t stop with the leader. It moves through the team as well.
In some teams, people learn quite quickly that asking too many questions makes them look slow or unsure. After a while, they stop asking and just try to keep up.
That’s one of the biggest gaps inside a team. People start acting as if they should already know what the leader meant and move forward without needing much else.
Something else happens as well. People learn to talk about what is going fine and stay quiet about the rest. Anything messy, unclear, or unfinished gets left unsaid.
Over time, fear starts shaping what people say and what they hold back. The team gets less honest about what is not working, and problems stay untouched for longer than they should.
Where the damage shows up
This starts in a very ordinary way. Someone gives direction too quickly, assumes it was clear enough, and moves on.
I know because I was one of those leaders. My to-do list was so long it could not be done in a day, sometimes not even in a year.
In a startup environment, it can feel like the whole organisation is sitting on your shoulders. When that pressure builds, speed feels like the only sensible response because everyone is waiting on you.
That’s when the direction goes out too quickly and some of the detail gets lost.
The team feels the rush as much as they hear the words, so people stop looking for more context and move ahead with whatever they think they understood.
Then it spreads. One unclear conversation becomes several, and by the time it reaches vendors or partners, people are already working from different versions of the same expectation.
You start seeing work repeated, and people get frustrated with each other because they don’t realise they’re working on the same thing.
After a while, trust starts to go because nobody is completely sure what was meant to happen or who was meant to do it.
You don’t need a weak team for that to happen. It can happen with good people when the expectation was never as clear as everyone thought.
Most “clarifying” makes it worse
One of the biggest mistakes you can make at this point is deciding for yourself what needs clarifying instead of finding out what the other person actually took from it.
You can try to fix the problem by explaining more, but that does not always help.
Sometimes you answer the original question, add extra detail around it, and leave people more confused than they were to begin with.
Or you can say a lot more and still leave the real point untouched. What matters is whether you dealt with the part that had actually gone wrong.
That’s why the better question is not did I say it clearly? Ask what the other person actually heard.
The other mistake is treating clarification like another announcement. It works much better when it becomes a conversation.
Support is not control
Not everyone on your team needs the same level of oversight.
A newer team member who is still learning the role usually needs more check-ins. Someone experienced and motivated can work with much lighter ones.
I think about it as an 80/20 problem. For someone who needs more support, I might stay close to roughly 80% of the work in progress. For someone stronger and more self-directed, maybe 20%.
The numbers are not really the point. The point is that different people need different levels of support, and a lot of leaders forget that.
The next part gets missed a lot. Don’t just tell people when you will check in. Ask what helps them do the work well.
People don’t all need the same thing. One person may prefer to give updates in writing, while someone else works better by talking things through.
Someone learning something new might need a daily check-in for a while, and another person may find that amount of contact suffocating.
You don’t have to follow every preference, but it helps to understand what makes the work easier for each person to do well.
What will make a difference is building a way of working that gives people the support they actually need.
Silence is not alignment
When nobody has any questions, don’t assume that means things are clear. More often, people don’t feel safe enough to say what’s not making sense yet.
If everyone walks away from an important conversation saying “that was fine” or “sounds good,” and nobody has anything they want to push on, that should worry you.
A team that’s really thinking something through will want to test at least one part of it. They might ask what happens if this goes wrong, or whether something has been missed.
The same thing applies in one-to-ones. If you want the real answer, give people a heads-up that you want their honest read on something specific, and be clear about what you are asking. Then ask and pause.
It’s easy to rush in and fill the silence too quickly. Leave it there for a moment, and that’s usually when people say what they really think.
Start where the cost is highest
Start with one or two things, not ten.
Sit down and ask where the biggest gap is right now. You don’t need the full picture straight away. Focus on the area where unclear expectations are causing the most trouble or wasting the most time.
Write it down, be honest about what is not working, and then do the part most leaders resist by naming it openly with your team.
You don’t have to have it figured out. You can say: I’m not sure I’ve been setting clear enough expectations in this area. I want to do better, and I’d like to understand what you need.
That kind of honesty doesn’t weaken your authority. It gives people room to tell you what is actually getting in the way.
Then get specific about the gap. Are you clear on the outcome but vague on how people should get there? Or have you been clear on behaviour without explaining why it matters? Start there.
Build in one way of checking this and actually use it, starting with the area that matters most and the team closest to it.
Change shows up in the work first
You’ll feel the difference before you can measure it properly.
People start saying sooner when something is unclear, and problems get picked up before they have had time to spread.
That’s the first sign things are getting clearer. The team spends less time cleaning up confusion later because more of it gets dealt with properly at the start.
👤 Kathy Wu Brady is an executive coach and adviser, a 2x CEO and 2x COO, and the writer behind Lead Without Limits. She has spent 20 years launching, scaling, and reshaping businesses across five industries, and now helps leaders make clearer decisions and lead with more courage. Connect with Kathy on LinkedIn
🤜🤛 More teamwork from Millennial Masters
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Asking people what they actually heard is great advice! It’s strange how many senior leaders recommend always projecting certainty. I’ve always found it best to just be honest when I don’t know something. People often start making the wrong assumptions when you sound too certain, which just creates more problems later on.
i keep seeing this play out. even when things feel clear in the moment, they don’t stay clear for long anymore.
tools change, priorities shift and AI gets added somewhere… and people end up working off slightly different versions again.
so at the end it’s not just ‘did people understand’, but it’s also how fast that understanding goes stale.
feels like you have to keep re-checking way more than before.