Most business owners I work with tell me their one-to-ones are going well.
“We talk openly.” “My team knows they can raise anything.” “There’s a good rapport.” Then I ask: “What’s the last thing someone told you that you didn’t want to hear, or you suspected that they left it all to the last minute because of fear of how you’d respond?”
The silence or change in body language tells me everything.
Because here’s what actually happens in many one-to-ones:
Your direct report comes prepared with updates. They share progress on projects. They mention some challenges, but only the easy ones. They ask for resources and for your decision on a project.
You feel informed. You feel engaged. You feel like you’re leading well.
However, it’s vital to recognise that the emotional tone you set as a leader can heavily influence the type of updates you receive. If team members sense a tense or unwelcoming mood, they might hold back the more complex or critical issues, focusing instead on positive or uncomplicated updates.
By being aware of your own emotional resonance, you can encourage a more honest and thorough flow of information.
And you both leave the meeting having successfully avoided the most critical conversation: what’s really, really happening that they have not mentioned.
Happens all the time.
One of the department heads raises a concern once. You’re busy, you’re preoccupied, and you don’t have the energy to really attend to it there and then, and you respond with: “Let’s park that for now”
They raise it again. This time, you’re more definitive: “I’ve been thinking about it, just leave it with me.” They don’t raise it a third time. Not because the problem went away. Because they learned the answer.
Six months later, when the project fails or the person quits, you’re surprised. You say: “Why didn’t they tell me sooner?” They did. You didn’t hear it as a warning; you heard it as an update.
What makes this expensive
The problems people stop raising don’t disappear. They mature. That pricing strategy you insisted on? It’s now three-quarters of disappointing revenue—perhaps costing the company hundreds of thousands in lost potential.
That staff bottleneck they mentioned? It’s now a client service crisis—leading to client attrition and revenue losses that could total in the high five figures.
That team dynamic they flagged gently? It’s now more than one person leaving, with resignation letters on your desk, costing you substantial recruitment fees and affecting team morale.
The cost isn’t just the failed initiative. It’s the erosion of their trust in you to handle matters when they need to be handled and fear that they will ultimately be blamed.
This erosion of trust could mean reputational damage, which, while hard to quantify precisely, could impact sales by an estimated 10-15% as team effectiveness drops and word spreads. Because once people learn that specific topics aren’t welcome, they stop bringing you problems altogether.
They bring you only what they think you want to hear. Because once people learn that certain topics aren’t welcome, they stop bringing you problems altogether. They bring you only what they think you want to hear.
And you, as the owner, are the last to realise you’re making decisions without all of the relevant information. The signal to look for
If your one-to-ones feel comfortable—consistently comfortable—that’s not necessarily good news.
Here’s the thing:
When was the last time someone in a one-to-one said something that made you think not only about the impact on the business, but also about your sales and the reputation of your business?
When was the last time you left a meeting thinking and admitting to yourself: “I should have dealt with that sooner or listened.”?
When was the last time someone challenged you or had the courage to not tiptoe around you on something you cared about, and you thanked them for it?
If you can’t answer those questions, your one-to-ones aren’t working. The question that changes everything. Instead of asking “How are things going?” try this: “What am I not seeing that you are?”
Then wait. Actually wait.
Don’t fill the silence. Don’t explain. Don’t defend and don’t criticise or blame. Most people need 30 seconds of uncomfortable quiet to shift from “what’s safe to say” to “what’s true,” and this will depend on how you have responded in the past, whether it’s really safe to be blunt, and whether you really listen.
If they still don’t answer honestly, until it’s too late, it tells you the cost of candour is still too high in your team, and you created that culture.
But if you ask this question consistently, and you genuinely receive what they say without penalty, you’ll start getting the information you actually need.
Not the information that makes you comfortable. The information that makes you effective and empowers them. Because the difference between well-informed leadership and expensive surprises isn’t the quality of your decisions. It’s the quality of truth you’re working with.
And that truth doesn’t flow upward automatically. You have to make it safe, repeatedly, until people believe you mean it.
Otherwise, your one-to-ones are just weekly confirmations that everything’s fine.
Right until it isn’t.
Until we meet
Morton
Most organisations need external challenge before a crisis forces it. Someone who can name what everyone sees but no one will say. I work with CEOs during transformation as an external strategic voice with no dependency on approval. Message me if you’re navigating change and open to a fresh perspective: value@mortonpatterson.com
