What To Do With a Frustrating Boss

m_David-Dye-HeadshotGuest post by David Dye.

I sat across from the Executive Vice President and made my case.

I suggested the company change the way it handled a specific process and made my five-point argument as to why it was a good idea.

The VP listened, grimaced, and then grinned. “If only it were that easy.”

“But it is that easy,” I challenged, “it’s just a matter of having the will to do it!” (I was young – and eager.)


Fast-forward thirteen years.

A new staff member stood on the other side of my desk – standing in the same place I had once stood…

Presenting the same case I had made thirteen years earlier.

But this time, she was speaking to me!

It's a matter of having the will to do it. Click To Tweet

Now that I was the executive, things would be different, right?

Managing Up

m_boss1The ability to successfully “manage up” or influence the people you report to is as essential to your leadership success as the ability to influence your own team.

One of the most common questions I hear from clients committed to meaningful leadership and change is: How do you respond when you perceive a supervisor’s behavior is damaging, self-defeating, or ineffective?

If you’re an eagle-eyed reader, you noticed I said “you perceive the behavior” to be negative…

m_collabI can hear the shouts already: “But it IS ineffective! I’m not making this up!”

Okay, I hear you…let’s take a deep breath and get some perspective.

One of the most important leadership lessons I ever learned is just how differently the world looks from each side of that desk.

The better you understand how your boss sees the world, the more influence you will have.

When faced with a supervisor who is difficult and ineffective, first thing to do is reflect. Click To Tweet


When you’re faced with a supervisor whose behavior appears to be damaging, self-defeating, or ineffective, the first thing to do is to reflect. Here are a few of the questions I ask myself in these situations:

m_boss2a) How serious is the issue?

After you hang out with friends, take a walk, and relax, is the issue truly significant or just a minor irritation? If it’s not really serious, don’t waste your time, energy, or relationships – even if you are 100% right about it.

I know I can get hung up on small issues that aren’t really important.

Perspective is vital. Do everything you can to find it.

m_meetingb) What is the lesson for you?

Yes, you read that correctly…the lesson for you.

If you’re serious about becoming an effective leader, you won’t find a better textbook from which to learn than the leaders around you.

When my VP said, “if only it was that easy,” he was giving me the opportunity to learn about strategic issues and think at a higher level.

After my stubborn insistence that it could work, he was patient and walked me through the world from his view. I didn’t like the more complex viewpoint, but I needed to hear it.

Perception is vital. Do everything you can to find it. Click To Tweet

The areas that most irritate you are often where you can learn the most and add another tool to your leadership tool belt.

c) What keeps your boss up at night?

One of the lessons I learned was that my boss had his own challenges and constraints. Up until that moment, I was unaware of them.

He had Board politics to contend with, budget constraints, obligations to other departments, and changing customer behaviors, just to name a few.

This was a vital moment of insight for me and was the start of my leadership success.

People do what makes sense to them.

What realities do your supervisor and their boss deal with every day? How can you help them meet their goals?

The areas that irritate you the most are often where you learn the most. Click To Tweet

d) What do you really want?

This question comes from Crucial Conversations by Kerry Patterson and his team. Before you think about addressing the issue, it is vital that you get crystal clear about what your best-self really wants.

Are you serving your team, the organization, and the supervisor?

If not, your motivations will impact your actions and you likely won’t have a chance to get the results you want. Patterson suggests that the twin motivations to enter any serious conversation are to 1) build the relationship and 2) solve the problem.

e) When It’s No Good

If you are a motivated, character-based leader committed to real change, serving your team, your own leaders, and your organization in a healthy way, I have some partially bad news:

Not everyone is like you. I’m sorry.

And while I’m on the subject, here’s some more partially bad news:

You cannot change anyone else.

You might expect me to have a fairy-dust-and-unicorns approach to problem-solving-up, but let’s be real: there are some lousy supervisors out there.

It’s essential that you understand the people you’re working with and how they might react.

If they lack integrity, are hostile, insecure, and you need this paycheck to buy medicine for your child, you’ll deal with the situation differently than if you have six months of income saved and your supervisor is generally reasonable.

I’ve been there – think this through carefully.

You will encounter all sorts of people in leadership and management roles who are there for other reasons, who lack better tools, or who have vastly different values.

m_peopleThe reality is that people will always do what they feel is good for them…because it’s easy, because it’s all they know, because it works and meets their needs for the time being.

Influencing your own supervisor is possible, but depending on the person, it takes work, time, and relationship.

And sometimes…they simply won’t change at all. The pain of doing so is greater than the benefit they perceive. In these situations, you have to decide if it makes sense to stay or to leave.

I called this “partially bad news”…why?

Because these realities clarify the power you do have: over yourself and the leader you will be. Ultimately, you still can be the leader you want your boss to be – and life will have provided you no better classroom.

What Happens Next

You might be wondering what happened with the young woman who stood on the other side of my desk and presented the same arguments I had made thirteen years earlier?

I did what my VP did for me…and what I hope you will do for your staff.

I shared the realities she didn’t know about and invited her to invent solutions so we could make it work. Together.

David M. Dye works with leaders, managers, and supervisors who want to get more done, build teams that care, and meet their goals. He is the President of Trailblaze, Inc, tweets from @davidmdye, and his book, The Seven Things Your Team Needs to Hear You Say is available on Amazon.com His latest book is Winning Well.

Please help me spread positivity by tweeting, liking, and commenting!

Marcella Bremer is an author and culture & change consultant. She co-founded this blog and ocai-online.com.

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