How to win an argument with your boss

Bosses are notorious for making bad decisions; just ask anyone who’s ever had one. No matter how they got there—college degrees, years of dedicated service, consistent and proven results—once they’re at the top of the ladder, they’re bound to screw things up sometimes. It’s inevitable.

And yet few of the people sitting on the rungs below ever seem to feel they can strike up a good debate when it comes to the decisions which affect their project outcomes. Conflict rarely goes over well.

There are ways to improve the situation, keep your job, and gain some respect in the process. It involves learning to win an argument. Which means two things: having a good point, and knowing how to deliver it.

First thing Monday morning

Yeah, that’s not the time to talk it out. This much should be obvious, but it’s worth mentioning: your boss’s busiest and most frustrating moment is not the time to pile on. Look for the quiet moment after lunch. You need an open mind on the other end of your talking points.

Discovery questions

Rather than barge in with assertions or disrupt a meeting in which you have no decision-making power, schedule a time to talk and then barge in with questions.

To begin, ask discovery questions. Make sure you know the whole situation before you marry yourself to the idea that someone’s wrong. Very often, there are a whole bunch of factors in play; you may not see them, but they may be affecting the decisions that provoked your concern.

Why are we doing this? Who’s involved? What have we tried before? What happened in that case? What things are you concerned about? Why?

Be sure to stress along the way that you just want to make sure you know all the constraints so you can make good decisions. It’s true, after all. Right?

Strategy questions

When you’re sure you understand the drivers behind the decision, and are still convinced there’s a problem, it’s time to move into strategy-related questions specifically designed to uncover the issues.

What are the goals of this project? How do we know those are the goals? How will we know when we’ve reached those goals? Does this solution really help us get there?

This again gives you a chance to find out if there’s something you hadn’t considered. And if there really is a problem, it’s going to come out in the answers. In theory.

The accountability pitch

Then and only then, aim toward a new solution. Throw out some ideas that can help convince your boss of the conclusion you have in mind.

Let me dig up some data on these kinds of situations. Let me whip up a comparison test and bring you the results next week, just so we can prove out the idea before we spend weeks on it.

In other words, volunteer to dig up some research and validate some hunches, then go back with that research in hand. Better yet, do it up front so you can say, “I found something that seems like it could cause a problem, and I’m wondering if we could consider another approach.“

The more questions you ask, the better. Rather than pitting you against your boss, it puts you in a state of mutual solution-seeking. No matter what happens, this is better for both of you. Because, remember, it could be that the decision made perfect sense in the first place. Your boss wants to do good work, after all. Just like you.

Speaking of. That’s the best thing you can do: go in with respect. Nothing will buy you an ear better than plain, simple respect.

Here’s to good decisions.

Post by Robert Hoekman, Jr.

Robert Hoekman, Jr. is a freelance writer, author, and product strategy consultant who has spoken to packed rooms all over the world. He is a columnist for the revered motorcycle culture and lifestyle magazine Iron & Air. He lives in downtown Phoenix, Arizona. Learn more about him at