Last Updated on 2023/07/27

One of the most common challenges people bring up in leadership training is the difficulty of convincing upper management to listen to concerns, accept ideas, or change their thinking on a decision they’ve made.

How do you boost your ability to convince people in your organization who have more power than you do?

Part of being a good follower is challenging the boss when the boss is blind to a real problem, or wrong and doesn’t realize it (or doesn’t want to admit it). How do you do this?

A Look at the Options

You can follow without question, even though you know it’s wrong. You will stay safe in the short term. The problem is that this is the kind of thinking that leads to mass resignations, product flops, lost opportunities, and other costly disasters. If the boss was driving a bus full of people toward a collapsed bridge, you’d say something, right?

You can also go the opposite direction. You can boldly and bluntly tell the boss she is wrong. A courageous choice, but risky. The reality is that many people with power do not like to be directly told they are wrong. Doing so too often can damage your career.

You can also try getting someone else to deliver your message. The message may indeed get delivered, but it’s your message and it may lose clarity in the process of third-party delivery. You’ll also miss the chance to build trust with the boss by delivering an important message yourself.

Each of these options has clear drawbacks. Are there any other choices?

How about this one? Object without appearing to object.

This, my friends, is the domain of great followers.


Objecting with Finesse

If you want to convince the boss to change his mind or to listen to your ideas, I invite you to focus on two goals as you communicate:

Goal #1 Increase trust between you and the boss.

Goal #2 Get your message across clearly.

Most bosses prize loyalty in their followers, but that doesn’t mean they want blind followers who never speak up.

Before you begin to think about what you want to say and how you want to say it, first decide if the issue is serious enough to speak up. We all have to choose our battles. A follower who automatically objects to everything is not a valuable follower.

If you decide the issue is important, then then make sure you have enough evidence to back up your objection and a solid alternative proposal.

Then choose a time where the boss can talk privately without too much stress. When you get your chance, say something like this:

Boss, about that plan you announced this morning. There are a few issues that may make it difficult to get the results you want, but if we make a few adjustments, I think we can make it happen. Whatever you decide, I will support, but you might want to consider (evidence to support your alternative proposal). I think a better/faster/safer/more efficient way of making the project a success would be (your alternative proposal).”

Don’t expect an immediate positive response. The boss may want to think about it. In the end, you may get rejected, but I predict that if you use this method, more often than not you will succeed.

The boss may also come back with objections or counterarguments. Be prepared for this. Sometimes it takes a few rounds to convince a strong-willed, capable leader.


We Never Have the Full Picture

We all live and work in situations that are not completely understood by others. It is virtually impossible for people we work with, even our family members, to understand everything that is going on in our world.

The same thing is true for the boss. You will only ever have partial visibility into what’s going on in the boss’ life at the moment. Pressures the boss may be under. Situations the boss is dealing with. If boss doesn’t’ get back to your request for a meeting or a written proposal or reacts badly at first, remember that you don’t really know what’s going on in the boss’ world. Be patient. Give gentle reminders. Try to understand the boss’ perspective and act accordingly.

I hope after reading this you feel more empowered to convince the boss, and I hope you go forth and object when you should object. Let me know how it goes!

Yours in learning,


Leave a Reply