This post is part of the “Where Leadership Gets Hard” series—based on over 25 years of coaching leaders through real problems. No theory, just what I’ve seen work.
Here’s a sentence that stops me in coaching sessions more often than it probably should.
“He hadn’t asked for a raise in about five years. But once he finally asked for it, the company quickly agreed in.” — Senior PM, reflecting on his own long silence
Five years. The coachee said it matter-of-factly, like he was reporting the weather. But stop and think about it. Five years of working hard, watching peers get raises, wondering why he wasn’t, assuming his boss was withholding — and then, the moment he finally asked, the company gave him most of what he wanted.
The organization wasn’t withholding. The organization was unaware.
I see this pattern constantly. A coachee carries a grievance for years — about compensation, about title, about scope, about a promotion path that never materialized. They assume the people above them know what they want and are deliberately not giving it to them. When they finally make the ask, they discover the bosses didn’t know. Sometimes the bosses say yes on the spot.
Why We Don’t Ask
Most leaders are strangely reluctant to ask for what they want. They’ll walk through fire for their team, fight for their direct reports’ promotions, lobby for their peers’ bonuses — but when it comes to their own needs, they fall silent. Three things are usually going on.
First, there’s a belief that if you deserve it, they’ll give it to you. That’s a lovely theory, but it’s not how most organizations work. Organizations respond to the squeaky wheel, and your quiet competence is not squeaking.
Second, there’s a fear of seeming ungrateful or entitled. Leaders don’t want to be the person making it about themselves. The irony is that their unwillingness to advocate for themselves usually doesn’t come across as humility — it comes across as a lack of ambition, which hurts them in ways they don’t see.
Third, there’s the fear of hearing no. If you ask and they say no, you now have to deal with the data. Not asking lets you keep the story that the company would have said yes, if only you’d asked. It’s a subtle form of self-protection.
How to Ask
The ask doesn’t need to be dramatic. It doesn’t need a grand speech. It usually sounds something like this: “I’ve been thinking about my path here. I’d like to talk about what would need to be true for me to be promoted to X in the next twelve months. Can we schedule thirty minutes to discuss?”
That’s it. A clear ask, a clear timeline, a clear invitation to respond. Then you let the other person respond. You don’t preempt their answer. You don’t apologize for asking. You don’t soften it into a vague musing that they can ignore.
Some bosses will say yes, and some will say no. Some will say, “Let me think about it.” All three are better than five years of silent accumulation, because all three give you information you can act on.
The Accumulated Cost
Here’s the thing I wish more leaders understood. Unspoken asks don’t stay unspoken. They come out sideways — as resentment, as disengagement, as the moment when a leader finally decides they’re done and walks out. By the time the walk-out happens, the boss is shocked. “I had no idea.” And that was the whole problem.
Say it earlier. Say it clearly. Give your organization a chance to meet you.
What have you been quietly waiting for someone to offer you — and what would happen if you just asked?
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