Confronting your boss is not fun. When I have done it, I have been met with anger, indifference, and/or passive aggressiveness. I have also seen some very positive reactions as well.

When I speak to groups about Building A Culture of Leadership within an organization, I always discuss the need for those without the title to speak up and lead up. I can usually count on someone approaching me after the program with a problem.

Some people tell me about their boss and the issues they will encounter if they attempt to lead up. I usually respond with empathy and one of two quotes from my dad:

• Just because it isn’t easy to do does not mean you should not be doing it!
• Whoever said leadership was going to be easy?

These quotes have some bite to them, but they are true nonetheless.

Leading Up is Up To Me!

Three Keys To Confronting Your Boss

There are three critical things to prepare when you approach your boss and begin to lead up.

1.  Prepare Your Why

Why are you speaking up? If the answer is a selfish one or one that may be perceived as selfish, be careful. When I had an issue, I always asked myself if I was speaking up for my own benefit or was I trying to help my boss or the team be better.

If I was trying to help my boss or the team, I made that clear up front:

“I know for this team to succeed, you must succeed. I want us all to succeed. It would be easier to stay quiet, but I truly think what I am about to say will help you lead us.”

It is critical that your boss knows why you are speaking up. Share your motives first. A perceived motive is often the difference between what is considered a complaint or constructive feedback.

When I perceive someone’s motive is selfish, then what I hear is a complaint. When I know someone’s motive is centered on helping others, I am more likely to listen and be open to the feedback. I must help my boss know my motives!

Don’t leave out this step. It is often the difference between success and failure in these situations.

2.  Prepare A Solution

Problem finders are everywhere. Even if someone has unselfish motives, if I do not hear a solution to the problem, what I have heard is a complaint.

When I approached my boss with some difficult feedback I tried to have answers to at least 2-3 of these questions:

• What alternative does my boss have?
• What have I seen work in other situations?
• How will this change current performance?
• What will my role be in supporting my boss’s changes?
• How would I communicate the changes if I were the boss?

Without solutions, a boss just feels dumped on by the person who is attempting to lead up. When someone challenged me and brought me solutions, I was grateful I was not given another problem that I had to solve from ground zero.

If your motive is truly unselfish, help your boss and bring solutions to the table!

3.  Prepare For Blowback

Even when I made sure I communicated my motives and brought viable solutions, I encountered resistance. Do not be surprised if you encounter initial blowback from a boss – especially if they have never encountered people with the courage to speak out in the past.

I prepared for the blowback by thinking through these items:

• Is this issue in my boss’s control?
• Is there a historical issue that I need to take into account?
• What are my boss’s most likely objections?
• How will I handle myself if my boss loses her temper?

When I prepared for the blowback, I was able to minimize its effects and get more positive results.

I always showed empathy for what my boss was facing. It amazed me how often I was able to gain insights into my boss and the decisions he made whenever I was focused on showing empathy in the midst of the blowback.

Leadership is a lonely job. An empathetic ear is often the best remedy for the initial blowback.  When I prepared for the blowback, I was able to minimize its effects and get more positive results.

It’s Up To Me To Lead Up!

Sometimes we complain that our leaders do not listen to us, but we never change how we approach those leaders. If things are to change, then we need to change! We must choose a different route.

Preparing my Why, preparing a solution, and preparing for the blowback will not always guarantee my success when I confront my boss. But when I know my motives are unselfish and I have prepared well for the conversation I have improved my odds.

The Bottom Line:

As a leader, whether I have the title or not, I will likely face resistance from my boss as I try to lead up.  If we take the time to examine why we have not chosen to lead up in the past, it is often rooted in fear. We fear our efforts will be for nothing, so therefore we do nothing.

Why should we swim upstream?

Because the path of least resistance leads to a mediocre existence!

Leading up and confronting my boss takes courage. But if done well, I will become a more valuable part of the team. My influence will increase because my boss will trust my motives and know I come with solutions. If I add empathy to the mix, my odds of success increase.

As a result I become a more complete leader.  I am not just leading my boss, but I am leading my peers as well.

Question:

What is preventing you from leading up and confronting your boss?