TSLH #002: 5 Ways To Better Manage Your Boss

TSLH #002: 5 Ways To Better Manage Your Boss

Read time: 6 minutes


Any leader knows that their role is about managing people on a team if they lead one, or if they are an individual contributor, that they need to deliver certain outcomes.

Only a few understand that their role is also to manage up, to manage their boss and any other person at a higher level who can impact their performance and success in the company.

Leaders who fail to manage up are at risk of seeing their career being derailed.

In my experience, I have seen 5 successful strategies, that if applied correctly, will showcase you as a leader who can manage up.


Strategy 1: Know your Bosses

Note that I am saying bosses and not boss. This is because although you usually have one direct boss, you may have multiple indirect bosses. For instance, as the international CFO of the company I work in, my boss is the CFO of the company. However, my boss is also the Senior VP of Sales for our international markets. My boss is also the Managing Director of Germany, where I work from.

The essential starting point is to look beyond your immediate direct manager and understand who all your bosses are. A great way to do this is to draw a “boss map” like the one below:

This is just an example, drawn from my experience in working with multi-international matrix organizations.

In this example, I mapped who could be the different bosses based on how strongly I feel I report to them and how big an impact each can have on my growth and success as a leader. It’s definitely not a one-size-fits all approach and anyone may have a different view of which quadrant their bosses belong to. What matters is whether you have identified all the right bosses.

Once you have mapped your bosses, the fun begins! In order to nurture your relationships and make sure you know your bosses, here are the top 5 things I recommend you learn from each of them:

  1. What are their goals?
  2. What do they see as the priorities for your area?
  3. What is their working style?
  4. What is their leadership philosophy?
  5. What is a blind spot they may have and where you can help them or add value?

The best time to ask these questions is when you start working with each boss, during a 1-1 or an introductory discussion. If you have missed the opportunity to do so, now is probably the next best time to do this.


Strategy 2: Ask for feedback

If you have great bosses, you may be lucky enough to receive regular, clear, constructive feedback. But let’s face it. As a leader, you may at times dread going into a 1-1 conversation, or an annual review, or any discussion where you need to offer such feedback to a direct report.

Guess what? Your bosses may feel exactly like you.

The good thing though is that feedback comes at no cost. You just have to ask for it!

What I suggest is also not to bluntly ask – as I usually did in my early career – “Hey, can you give me some feedback on how I am doing?” Frankly, this is too generic, and it will bring generic responses most of the times.

Instead, I recommend asking feedback from your bosses by using questions such as “What do you think I could have done better in that situation?”, “How do you think I handled that discussion?”, “What do you think of my approach to achieve this?”, “How differently would you have handled this?”, etc.

The key is that by getting more relevant feedback, you can spot your blind spots (and those of your team) and turn that feedback into opportunities to learn and develop. This is a gift!


Strategy 3: Set a career agreement

I will share a secret: the person who cares the most about your success is … YOU!

This might be painful to read, but it is the undisputable truth: People around you may be full of good intentions, ready to help and support, but in the end, everybody has their priorities and they usually do not include caring for other people’s needs or success.

That said, it’s also a fact that to achieve success alone is close to impossible. And the next best person(s) who can help you achieve your career goals for instance is(are) your boss(es).

It is therefore critical that you establish some sort of unwritten agreement with your boss(es) on what it is you need from them in exchange for your commitment to their success and the success of the organization.

Creating this partnership is key to your development and growth. We often hear that people join good companies and leave bad bosses. This is true. At the same time, if you want to succeed, you are 100% responsible for the quality of the relationship with your boss.

I hear you ask “well, my boss is really bad, why should I be the only one responsible for making the relationship good?”

You have 2 options to be honest. Either you complain, and keep complaining, and you are a victim, and you will probably end up leaving your job.

Or you decide you want to do something about it and take full accountability. There’s no guarantee it will work of course, but at least you will have tried.

From my experience, here are at least 3 things you should get from your bosses when you establish that win-win situation:

  1. Help to expand your network, introduce you to new people. In one of my roles for instance, I had agreed with my boss that he would give me an opportunity to make a presentation to the CFO of the company, to increase my visibility.
  2. Support for training, and your continuous development, including having regular discussions about career growth. Feedback is the key, to understand what you need to do more of or less of in order to succeed and get promoted to the next role.
  3. Coaching about performance and any topic that you bring in discussions. At times, learning from your bosses how to do something specific (especially when starting in a position) is what matters. At other times, getting real and good coaching from your bosses can help you tremendously to solve issues and enhance your performance.

The best way to create that career covenant is once you have established your credibility with your boss and they know they owe you. That’s when you can ask for something in return for your commitment to your boss’ success.


Strategy 4: Push back and disagree

This is probably the #1 leadership lesson I have learned in my career:

You cannot let your bosses in the dark about bad decisions, mistakes or a situation in the organization.

Instead, you must show courage, step up and tell your bosses when they are wrong, or about to make a mistake. It can be really scary to do, but just imagine the consequences for you (and the organization) if you don’t speak.

Of course, it’s not just about saying “Oh no, you’re wrong, we should not do that”. It’s about seeing that the boss is wrong in assuming something or making a decision for instance, and at the same time seeing that nobody in the organization will tell him.

You also can’t disagree with your direct boss or any boss right out in the open without having established some kind of common understanding between the two of you.

I suggest having a discussion on this when you start working with your boss and ask a question like:

👉 “At times, I may disagree with what you say or with something you do. Is it OK for me to let you know when this happens?”, or

👉 “In these times where I might disagree with you or be of another opinion, would you prefer me to tell you immediately or would you rather I came to your office after?”

If you want/can disagree during a meeting, keep in mind that you should always disagree respectfully. Instead of saying “I disagree with you on this!”, make it a more thought out statement like “I have a different perspective on the subject, would you like to hear it?”


Strategy 5: Ask – Don’t play the victim

I won’t repeat it enough: You are 100% responsible for the quality of your relationship with your boss.

You can spend your time complaining about things, your bosses, these processes that are crap, the lack of support, etc.

The difference is, an effective leader will step up and do something about what it is they are complaining about.

If you want to manage your bosses effectively, don’t complain about them, don’t talk in their back.

Instead, go see them, have a discussion, clarify misunderstandings, get clarity on what it is they are expecting from you or what you are expecting from them. Ask for anything you need. See for yourself how this improves the way you are seen as a leader.


As a leader, it’s on you to manage your relationships with your bosses. Not only the boss you are directly reporting to. All the bosses you have. You are 100% responsible for the quality of these relationships, like it or not. It’s life!

Have fun with this and let me know about your progress.

TL; DR (Too Long, Did not Read)

5 strategies to manage your bosses

  1. Know your bosses
  2. Ask for feedback
  3. Set a career agreement
  4. Push back and disagree
  5. Ask – Don’t play the victim

Whenever you’re ready, there are 3 ways I can help you:

1️⃣ Work 1-1 with me to step up as the authentic leader you aspire to be.

2️⃣ Hire me to help you build a high-performing team.

3️⃣ Start with my affordable digital course on Mastering Difficult Conversations for Leaders.