What To Do When Your Boss Keeps Asking “Stupid” Questions
Are you sick of being treated like a human chatbot? Here’s what to try instead.
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The Letter
“Jenn, my boss is constantly coming to me with questions they should know the answer to, and I’m sick of it. Sometimes I feel like they are totally unqualified to do their job. What should I do?”
Why This Situation Feels So Frustrating
Well, that’s super frustrating. And my response might be a bit frustrating, too.
Because the reality is:
- Your boss might be unqualified
- Or overwhelmed
- Or disorganized
- Or getting pressure from their boss
- Or… all of the above
You’ll probably never know for sure.
And regardless, your boss’s qualifications (or lack thereof) aren’t really your problem to solve.
Your real problem: your boss is leaning heavily on you—and you’re sick of it.
If I had to guess, this dynamic bothers you because it:
- Disrupts your workflow
- Feels like a waste of time
- Is a waste of time and drains your capacity
- Makes you answer “stupid questions” from someone who likely earns more than you
Totally fair.
A Reality Check About Leadership
I know you know this, but it’s worth saying:
- It’s not a leader’s job to know everything.
- It is a leader’s job to make sure everything gets done.
Many leaders are expected to manage the big picture—not memorize every detail.
So yes, it’s common to hear questions like:
- “What’s the background here?”
- “What’s the risk?”
- “What’s our recommendation?”
- “Where is that slide deck from the last report out?”
Common? Yes.
Enjoyable or fulfilling for you? Not exactly.
What to Do Instead: Stop Being the “Human Chatbot”
If your boss constantly asks questions they “should know,” here’s a smarter approach:
Build a System Instead
Create a one-page “Decisions + FAQs” document.
Include things like:
- Common questions with standard answers
- Key dates and deadlines
- Important stakeholder meetings
- Links to presentations or internal communications
Tailor it to what you get asked most often.
How to Introduce It to Your Boss
Keep it simple and proactive:
“I put together a one-pager so we don’t have to reinvent this every week. I’ll keep it updated.”
No drama. No blame. Just solutions.
Why This Works
This small shift does a lot of heavy lifting:
- Reduces constant interruptions
- Streamlines communication
- Saves time for both of you
- Makes key information easy to find
- Positions you as someone who improves messy situations
Yes, it’s a little extra effort upfront.
But it pays off fast—and makes your work life way less annoying.
A Slightly Petty (But Honest) Bonus
Let’s be real for a second:
This is also one more example of how you can rise above the chaos and quietly demonstrate your value.
Think of it as proof of how great you are compared to your boss. 😏
Try It and See What Happens
Give it a shot and see how it changes the dynamic.
- Does your boss ask fewer questions?
- Do you feel less interrupted?
- Do you gain a little more control over your time?
That’s the goal.
Let’s Learn Together
That’s my take—what’s yours?
Drop your advice in the comments. Let’s learn from each other.
Got a sticky workplace situation? Send it my way and we’ll tackle it in a future post.
And as always—happy improving.