Managing Up

How to Work With Your Boss

A lot of what I know about management, I learned from managers who were doing it poorly.

And that’s because the lessons that stay with you are the ones you feel.

When you work for someone who communicates poorly, who never explains the reasoning behind a decision, who leaves you outside the thinking and then expects your commitment to the outcome, you experience the consequences directly. You carry that learning with you more than anything you read in a book on leadership.

I learned to be direct in my own communication because I sat through years of speeches that taught me nothing. Long, vague, theoretical, convoluted. I remember the boredom clearly. At some point I decided I would never put a room through that. Short statements. Clear messages. Simple terminology. Concrete examples. Precise vocabulary.

Hence why I tell young professionals to pay close attention to how their manager and situations make them feel, and to take notes.

In the relationship with a boss you will learn more from the failings than from the qualities, for the simple reason that you live the failings. The qualities you admire from a distance, while the flaws you absorb.

That is the first half of it. The second half is what you do with the relationship while you are inside it.

The most common mistake I see is treating the manager as a fixed condition to be endured.

A more useful approach is to make the relationship explicitly about mutual interest. If you sit in someone’s team, you have a genuine stake in that team performing, and so does your manager. Starting from that shared interest changes the tone of every difficult conversation you will have with them.

When a junior employee wants to raise something, the framing that works is a request for help rather than an assessment of their manager’s performance. Grading your boss rarely ends well.

What you can say instead is this: I want to be as useful as possible to you and to the team, and if you did this, or gave me that, I would deliver more. Let me help you help me.

The tone carries the message. Said as a criticism, it invites defensiveness. Said as a request for input, it is easy to accept and constructive to act on. I have seen this work with the most difficult and least approachable managers, because it removes the threat from the conversation. You are asking them to help you become more productive for them.

From the other side of the desk, the same principle applies in reverse. When I had to give someone difficult feedback, I began by restating why they were there. If I did not want you in my team, you would not be in my team. You are here, and I take responsibility for that. Everything I am about to tell you exists so that you succeed, because your success will also be mine.

Once that is established, people absorb criticism differently. The objective has been named, the relationship has been confirmed, and what follows lands as an instruction rather than a verdict.

On feedback itself, there is a distinction worth understanding early. When someone is young, they need encouragement. I needed it. Early in my career, criticism left me deflated, and what moved me forward was being told I was doing well.

However, the stage passes. Once you reach a certain level of maturity, encouragement goes over your head. It is pleasant, it is good for morale, but it stops changing anything, because comfort and growth pull in opposite directions. What interests you at that point is improvement, and improvement arrives only through people willing to tell you what could have been better. Like ‘That speech was strong. If you want it to be excellent, I would have done this instead…’

Whether they are right is almost beside the point. You accept it, you consider it, and above all you encourage people to believe that being critical of you is a way of pleasing you rather than a risk they are taking. The moment your team believes that, the quality of the information reaching you changes permanently.

Indeed, the whole question of managing up comes down to a single reframing: working with someone toward a result you both need, rather than working for someone.

Once the relationship rests on that, feedback moves in both directions and the difficult conversations become considerably easier for everyone involved.

Let me know if you apply this framework in the comments.