“Just Ask If You’re Unsure” Is a Lazy Management Myth
“History Doesn’t Repeat Itself, but It Often Rhymes”
For someone like me working in tech I have to say this Mark Twain quote hits hard.
When I’ve had a couple of tricky starts to jobs, and managers have often appended the same passive aggressive trash to the end of a conversation. They’ve confirmed with me that I’ve understood with a simple:
“Just ask if you’re unsure”
It sounds reasonable. Supportive, even. Yet this is the sort of thing managers say when they want to signal psychological safety without doing any actual work, and manage to deliver the opposite of that.
I got asked just this question in my job just after covid where I didn’t pass probation, and my most recent position where I struggled to pass probation. What did I do? In both cases I did an impression of a nodding dog and said I understood when I did nothing of the sort.
One time that worked, one time it didn’t.
The Issue
I’ve heard technical managers and people managers use the “Just ask if you’re unsure” defensive question.
The idea is simple. If you don’t understand something, you need to ask. If you’re blocked simply speak up. The result is that if you are confused, well it’s on you to resolve that because you’re the one that doesn’t understand.
People don’t seem to get it that this advice doesn’t seem to help anyone. Which makes me think that nobody actually cares if their advice fails to help, it’s the performative action of giving the advice which matters, and brings the intended result for the advice-giver. You might well be burnt by this advice a few times until you get it.
The issue is this.
You cannot ask if you’re unsure if you don’t know that you’re unsure.
We all know this. Understanding isn’t binary, and although “I get it” is some distance away from “I don’t get it” there are almost infinite gradations between the two. One of those is the most dangerous, and it’s very difficult to move on from it.
“I think I get it”
Which is where the pits of hell reside. It might lead to mistaken architectural decisions that quickly harden into production bugs. It might lead to business logic that will result in a production incident early one Sunday morning. Not because anyone deliberately implements the wrong thing, not because anyone is careless but because they misunderstood the level of complexity involved.
You may not know that a message is incomplete. A receiver cannot know that an explanation is missing three critical assumptions, but that’s exactly what “just ask if you’re unsure” means. The onus is on you to know some details that by definition you cannot know.
So how exactly are you going to be able to say that you’re unsure about some details (when you don’t know the detail to ask about). How is this even possible?
The Cost of Asking
“Just ask” also ignores the social economics of modern tech teams.
Every question has a price:
You interrupt someone.
You expose ignorance.
You risk being seen as slow, needy, or not senior enough.
You might not even get a response, as everyone ignores you for something “more important” to do and unblocking you doesn’t come into the equation.
I know that asking too many questions is quietly remembered. A new member of staff at our place shared that they just blew $3000 on Cursor credits to avoid asking questions on Slack. This is a very very real use case, and what really happened.
They’ll do well though. Because performance reviews and phrases like needs more independence or could unblock themselves faster won’t be a problem that they have to face.
The logical thing to do is to hedge. Wait. Then try again. Simply hammer Google, hammer AI and guess. When that doesn’t work (and in the end with sufficient complexity it won’t) the response is often silence. If you’re lucky you’ll get a thumbs-up emoji, or a “works for me” comment from someone who doesn’t even have the project open.
This is where mistakes come from, and is the origin story of plenty of bugs and problems in production.
Slack Is the Defeatist Communication Strategy
When I joined Revolut I couldn’t get my dev environment set up correctly. Honestly I wasn’t familiar with how things worked in a big company and simply couldn’t get things running by myself.
My solution? Post in Slack. No response. Wait. Then try again later, phrased more politely. Still nothing.
Throughout the long waiting period I hit Stack Overflow. Pre-AI that’s all we had, and I really wanted things to work, and worked hard at it. Those posts never explained what was going on, and even now using AI I learn nothing from the process. Docs don’t help at work, and when there are issues the whole team moves on, satisfied that things work.
Eventually they brute-force it, cargo-culting fixes from Stack Overflow until the build passes. Nobody ever explains why it failed. Nobody updates the docs. The team moves on, satisfied that “they should have asked”.
They did ask. It didn’t help anything.
The problem wasn’t uncertainty. It was absence.
The Burden Is Always on the Wrong Person
“Just ask if you’re unsure” quietly shifts responsibility in one direction only.
It absolves the sender from:
• Checking understanding
• Calibrating complexity
• Providing context
• Following up
If something goes wrong later, the post-hoc explanation is ready-made:
“Well, they should have asked”
It’s a perfect defence. Unfalsifiable. Convenient. And completely useless as a learning mechanism.
Good communication isn’t reactive. It doesn’t rely on the listener detecting invisible gaps in their own understanding.
Real Clarity Is Proactive
The teams that actually work well don’t rely on this mantra.
They:
• Over-explain by default
• State assumptions explicitly
• Invite questions after explaining, not instead of explaining
• Check understanding without making it awkward
• Notice when silence is a problem, not a sign of competence
They understand that confusion often only becomes visible after someone has confidently gone in the wrong direction.
Asking Isn’t the Problem
The real issue isn’t that people don’t ask.
It’s that we pretend communication failure is an individual flaw rather than a systemic one.
“Just ask if you’re unsure” sounds supportive, but in practice it’s a shrug. A way of saying I’ve done my part without ever verifying that you actually have.
And if your system depends on people knowing exactly when they don’t understand something — congratulations. You’ve built a system that fails silently, at scale.
Which, come to think of it, is very on-brand for modern tech.
About The Author
Professional Software Developer “The Secret Developer” can be found on Twitter @TheSDeveloper.
The Secret Developer feels tired with all this. Very tired.