One of the questions I get most often — not from executives, but from the people around them — goes something like this:
I can see that something isn’t working. I think my leader needs to hear it. But I don’t know how to bring it up without making things worse or putting myself at risk.
It’s a real dilemma. The people closest to the work often have the clearest view of what’s going wrong in a team’s culture, communication, or leadership dynamics. And they’re also the most exposed when they speak up about it.
So how do you raise a concern when you don’t have the authority to change it?
The first thing I’d ask is this: Do you actually want it to be different? And once you’ve answered that: What are you willing to do to make it different?
That sounds like an obvious set of questions, but they are shockingly seldom asked so directly, and when they are, they are typically answered at a high level.
To be clear, wanting things to be different and being willing to do something about it are not the same. If you’re not prepared to take any action that carries risk, the conversation ends there — and that’s a legitimate answer. Not every situation is worth the exposure (you know, that whole “hill to die on” thing).
But if you do want it to be different, and you’re willing to do something about it, here’s the approach I recommend most often.
Don’t lead with your opinion. Lead with curiosity — and with an outside resource.
Find an article, a book, a framework, a piece of content that speaks to what you’re observing. Something that names the dynamic without pointing a finger at any individual. Then go to your leader and say something like: I came across this and thought it was really applicable to some of what we’re navigating as a team. Would you be interested in reading it?
That question — “would you be interested?” — does something important. It creates an invitation rather than an accusation. It gives your leader the option to engage without feeling cornered.
Most people, when approached with genuine curiosity rather than judgment, will say yes. And that yes opens a door that a direct confrontation would have closed.
From there, you can have a real conversation. You can ask: What do you think? Does any of this resonate with where we are? You can share your perspective in response to the content rather than as a critique of the person. The dynamic is entirely different.
There’s a related question you could ask as well: Would you want to know if I felt something wasn’t working? That’s usually a disarming question because most leaders — even those with blind spots — will find their curiosity piqued and say yes. And that yes becomes implicit permission for the conversation that follows, which is still one of curiosity, not judgment.
I want to be honest about something, though.
Not every workplace is safe enough for this kind of courage. And a fair risk assessment matters.
If your leader has demonstrated that they’re not open to feedback, that they retaliate against people who raise concerns, that they’re deeply entrenched in denial — then the calculus changes. The potential benefit of speaking up may be genuinely smaller than the risk of what follows. In that case, choosing not to act isn’t weakness. It’s wisdom.
But it also might mean something worth sitting with: if the environment is so unsafe that an honest, well-intentioned concern can’t be raised without serious risk, that’s important information about where you are. And whether you’re willing to stay there is a question only you can answer.
For most people, in most organizations, the situation isn’t that extreme. There’s more room than people assume. And the leaders who most need to hear something are often more open to it than their direct reports expect — especially when it’s offered with curiosity instead of judgment.
Be curious, not judgmental. Lead with a question, not a verdict. And give your leader the chance to surprise you.
Photo by Daniele Levis Pelusi on Unsplash
