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Before You Ask Your Boss, Ask Yourself These Five Questions
Asking for help isn’t the problem. Asking before you’ve done your own thinking is.
The Instinct Check
Your boss is holding up the work
Your project is stuck waiting on something your boss owes you, and the deadline isn’t moving.
The situation
You’re leading a project with a firm deadline. Your part is ready to move, except for one thing: a decision and a draft your boss said they’d have to you last week.
You sent a reminder. They replied, “Yep, on it.” That was five days ago.
Now your team is asking when they can start the next phase, and you don’t have an answer.
Let’s check that instinct.
What are you noticing?
- “Yep, on it” might mean on it. It might mean buried. You don’t know which yet.
- Your boss may not see the downstream impact: the team waiting, the timeline, the next phase.
- “The deliverable” is easy to put off. “One decision by Thursday” is much harder to ignore.
- There’s a power dynamic here, and it may be pushing you to hint instead of ask.
- Some of the work might be able to move forward without them. Have you checked?
Ask one more question
What is the smallest, clearest thing I could ask for that would get the work moving again?
The Instinct Check
- NoticeNotice the gap between “on it” and what’s actually happening. Then notice what you’ve been doing about it.
- UnderstandZoom out. What else is your boss carrying right now, and where does this realistically sit on their list?
- DecideSeparate what only they can decide from what you could reasonably move forward on yourself.
- ActMake one specific ask, with the cost of waiting and a proposed next step. Make it easy to say yes.
Adapt your instinct
- If your boss is fast-moving and big-picture
- A quick, specific ask is useful. A long recap isn’t. Lead with the decision you need and when you need it.
- If your boss is detail-oriented
- Context is useful. Urgency without explanation isn’t. Show them what’s ready, what’s waiting on them, and why it matters.
- If you tend to avoid friction with people senior to you
- Politeness is useful. Being vague isn’t. You can be respectful and still be clear about what waiting is costing.
What I’d do
I have questions. Not about your boss. About the ask.
When something is stuck with someone senior, our instinct is usually to remind them again. Politely. Then slightly less politely. But if the first reminder didn’t work, the second one probably won’t either, because nothing about the request has changed.
So here’s where my brain goes: what exactly is stuck? Is it the whole draft, or one decision inside it? A lot of the time, the thing your boss is avoiding isn’t the work. It’s one hard call buried in the work. If you can find that call and bring it to them on its own, you’ve made their job much smaller.
Then I’d make the cost visible. Not as a complaint. As information they probably don’t have.
Something like: “I know you’ve got a lot on your plate right now. The team is ready to start the next phase, and we’re waiting on the decision about the vendor. If I can get that by Thursday, we stay on schedule. Want me to put together two options so you can pick one?”
That one message does a few things. It’s specific. It names the impact. It gives a date. And it offers to do some of the lifting.
One thing I wouldn’t do is quietly work around them on a decision that’s actually theirs. You might be right, and it can still cost you trust. If it’s your call, make it. If it’s theirs, make it easy for them to make.
And if this keeps happening, that’s a different conversation. A worthwhile one, about how the two of you work together.
The Good Instinct
Don’t ask your boss for the whole thing. Ask for the next decision.
Next step
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Should I Escalate This?
Something landed on your desk and you’re not sure whether it’s yours to handle or something to take upstairs. This one-page worksheet helps you think it through before you ask, so you either own it with confidence or escalate with a clear ask.
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