My Manager Doesn't Understand Me. Are You Sure?

"My manager doesn't understand what I'm saying."

I've heard this sentence many times. After meetings, in 1:1s, in channels the manager isn't in. I've said it myself, more than once.

These days I hear it from both sides. I'm a lead: I report to an engineering manager, and six engineers across three teams work with me. Some days I'm the one shouting that something ahead looks wrong. Other days I'm the one who hears the shout and keeps the course anyway.

Sitting in both seats has made one thing clearer to me. This sentence is rarely a diagnosis. It's usually a conclusion we reach too early, and this post is about what to do before reaching it.

One sentence, three different problems

When we say "my manager doesn't get it," one of three things has usually happened:

1. The signal didn't land. The manager didn't hear what we said with the clarity or priority it needed. Maybe it got lost among ten other problems. Maybe we didn't say it well.
2. The signal landed, but the decision went another way. The manager understood exactly what we meant and reached a different conclusion, using information we don't have.
3. The signal landed, and the decision is wrong. This happens too. Managers are people.

From the outside, all three look the same: we raised something and nothing changed. But each one calls for a different response.

Mistake the first case for the third, and you get frustrated with your manager instead of improving how you communicate. Mistake the second for the third, and you stop trusting a decision that may have been right.

The first two cases come from two asymmetries that exist in almost every organization:

• Attention asymmetry. The higher you go, the more problems land on one person's desk, and the smaller each problem's share of their attention.
• Information asymmetry. Every seat sees part of the map. Engineers see the ground in detail. Managers see a wider picture, including constraints they sometimes can't talk about.

So how do you tell which case you're in?

Scout or soldier?

In The Scout Mindset, Julia Galef describes two ways of reasoning. The soldier mindset treats reasoning like combat: defend the beliefs you like, attack the ones you don't. The scout mindset treats it like reconnaissance. The goal is an accurate map of the territory, even when the map is inconvenient.

"My manager doesn't understand" is a very comfortable story for the soldier. It protects our ego, puts the blame somewhere else, and asks nothing of us. The scout asks a different question: which of the three cases is this?

Here's a simple test I find useful:

Can my manager restate my concern in a way I'd agree with? Can I explain their decision in a way they'd agree with?

If the answer to the first question is no, you're probably in case one. If both answers are yes and you still disagree, the issue is disagreement, not understanding. That calls for a different conversation.

Case one: when the signal doesn't land

Let's look at it from the other side of the table.

Each engineer I work with might hit one or two blockers a day, and it's natural for them to expect me to have an answer for each. But with six people across three teams, my desk collects several times that, plus whatever my own manager needs from me. My manager's desk is busier still.

So if I expect my manager to be available all day, I'm asking for more of a limited resource than actually exists. If I get something like an hour a day with them, the useful question is simple: what deserves that hour?

For any problem, I have four options:

• Solve: handle it myself, and update them later if it matters.
• Share: make sure they know, without asking them to act.
• Escalate: ask for a decision or help now.
• Defer: park it for a specific time and look at it together then.

I think learning to make this call is one of the things that makes people reliable in the human chain of an organization. Your manager learns that when you escalate, it's real. And when you stay quiet, you've got it handled.

Eisenhower, from your manager's desk

The Eisenhower matrix is a well-known prioritization tool: sort work into four boxes by urgency and importance. Most people use it for their own desk. I'd suggest drawing it from your manager's desk instead.

That shift is the whole point. Something urgent and important to me might not even make the "important" row once it sits next to ten bigger problems on my manager's desk. Seeing things from the other side stops being general advice and becomes a tool.

The matrix has two gaps, though:

• It doesn't say whose decision it is. A problem can be urgent while the decision right sits with someone else. So it needs one more question next to it: is this mine to decide?
• "Important" is exactly where our information is incomplete. I might misjudge how much something matters because I can't see part of the map. The matrix itself needs a scout mindset. If you're unsure how important something is, share that uncertainty, briefly.

What does speaking up "at the right volume" look like?

A few years ago, we were in the middle of a large migration, and I was worried about the risks of the move. I raised it with my manager, and they changed course. Our work got much easier afterwards.

Looking back, I don't think it worked only because the concern was valid. Three things helped:

• I brought data and reasoning, not just a feeling.
• I raised it early, before changing course got expensive.
• I kept it short, so my manager understood the risk in the middle of a thousand other things.

You can turn this into a simple template for raising a concern:

1. What did I see?
2. Why does it matter? What happens if we do nothing?
3. What data or evidence do I have?
4. What have I tried, or what do I propose?
5. What do I need from you, and by when?

A warning with these five parts gets noticed even on the busiest desk. A warning that only says "this is really bad" hands the work of understanding it to the person with the least time.

Case two: the iceberg on the other side of the ship

There's an analogy I often use with my team. I call it the sailor mindset.

Imagine the company is a ship. You're a sailor and your manager is the captain. You're both on the same ship, trying to reach the same place. You're standing on one side of the deck and you spot a rock in the distance. The reasonable thing is to shout, so the captain hears and changes course.

Sometimes the captain hears you and keeps going.

That's when it's tempting to decide the captain is a fool who'll sink everyone. But maybe on the other side of the ship, where you can't see, there's a bigger iceberg. Turning away from your rock would have meant hitting something far worse.

When I was the captain

Not long ago, I had a talented mid-level engineer who, as I saw it, was stuck in a loop. They weren't growing, and they were waiting for others to open the way. They seemed to see choice and impact as things other people had.

I deliberately put more pressure on them, to push them out of that shell. I wanted them to see that they were responsible for their own growth, and to shift their expectations and actions from visible but low-value work to work that actually mattered.

The senior engineer on that team was worried. They told me several times that I wasn't paying attention to this person. From where they stood, the warning made sense: a teammate was under pressure, and their lead seemed to be doing nothing about it.

I heard it, and I didn't change course. A few months later, we saw the results. That engineer became the owner of a service and did really well with it. Only then did the plan become clear to both of them.

Two things stay with me from that:

• I couldn't explain the plan up front. The whole point was for them to realize they owned their growth. Explaining it early would have broken the plan. Some icebergs can't be shown in the moment.
• The senior's feedback wasn't wasted. It didn't change the course, but it made me watch much more closely for pressure turning into burnout. A warning that doesn't change a ship's direction can still change how it's steered.

Before concluding that the captain got it wrong, the scout asks one more question:

What would I need to know for this decision to make sense?

If you can come up with at least one reasonable answer, case two is a real possibility. If you honestly can't, it may be time to ask directly, instead of sitting alone with a negative guess.

The sailor mindset: speak up, then commit

So what's the sailor's job? I think it has two parts.

First, speak up. Clearly, precisely, and at the right volume. Staying silent in front of a rock you can see isn't loyalty; it's negligence. The migration story shows that sometimes the warning is exactly what changes the course.

Second, once you've been heard, respect the decision. Let the person responsible for the whole ship make the final call. Commit to it, even if you disagreed. Don't undermine it behind their back, and don't restart the same argument every week.

Respecting a decision doesn't mean switching off your judgment, though. What's worth evaluating is the captain's pattern over time, more than any single call:

• When they can, do they explain their reasoning?
• When they can't, do they at least say there's context they can't share yet?
• Do they close the loop later and explain why?
• Do they take your feedback seriously, even when they don't change course?

If the answer is mostly yes, you have a good manager, and that's worth staying for. If you keep seeing decisions made without any defensible logic, out of nothing but personal preference, it may be time to rethink your own path.

Where this model breaks

Every analogy breaks somewhere, and this one is no exception.

The Titanic did receive iceberg warnings. Several ice warnings reached the ship, and it kept going at speed. The Challenger disaster is another well-known case: engineers warned about how a component would behave in cold weather, and the launch went ahead. "Speak up, then commit" isn't a universal law.

I think this model works for ordinary, reversible decisions, which covers most of what we decide day to day. When user safety, ethics, legal issues, or irreversible harm are on the line, saying it once isn't enough. That's when other routes matter: putting it in writing, going one level up, or using the organization's formal channels.

Blind deference is also a soldier mindset. "My manager must know something" can be just as comfortable a story as "my manager is an idiot." This time it's a way to avoid conflict. A real scout assumes neither.

The captain has obligations too. This model doesn't only ask things of sailors. A captain who never explains, never closes the loop, and leaves feedback unanswered is teaching the crew that shouting is pointless. And a ship whose sailors have gone quiet won't see the rocks in time.

Before you say "they don't get it"

Next time the sentence is on the tip of your tongue, ask yourself:

1. Did I say it with data, briefly, and early enough?
2. Is this actually urgent and important on my manager's desk, or only on mine?
3. Is this decision mine or theirs?
4. Can my manager restate my concern in a way I'd agree with?
5. Can I explain their decision in a way they'd agree with?
6. What would I need to know for this decision to make sense? If I don't know, have I asked?
7. Is this decision reversible, or is something at stake where saying it once isn't enough?

Back to that sentence

"My manager doesn't understand" is sometimes true. But more often, I think, there's a better question hiding behind it:

What am I not seeing, and how easy did I make it to hear me?

The first half makes us humbler. The second half makes us more effective. And a sailor who has both is the one every captain wants on deck.

What about you? Have you been sure your manager was wrong, then later found the iceberg on the other side of the ship? Or were you actually right? I'd like to hear it.

Further reading

• Julia Galef, The Scout Mindset: Why Some People See Things Clearly and Others Don't, Portfolio/Penguin, 2021.