How to Push Back on Your Boss Like a Pro

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Unless you own your own business, most leaders have a boss.

The thing is, bosses aren’t always in touch with reality and that can be “a little challenging” (which is Shanespeak for “a freakin’ nightmare”).

Fortunately, there are things you can do if you’re in this situation.

As an example, let’s take Martin... the CEO of a rapidly growing software services company.

Martin started out in finance but rose through the ranks at breakneck speed. He was a strong leader who had good instincts for the right path to take, and more often than not he was correct.

His high-speed performance and uncanny ability to make the right call helped fuel his meteoric rise to the top.

He could think and speak faster than anyone. He could motivate his team to hit and exceed every goal he set, often before the deadline for it.

The problem is, he was so far ahead of others in this thinking, he would interrupt them before they could complete their thought… leaving them feeling irritated and discontent.

As a result, he would sometimes leap to conclusions and take action from baseless assumptions.

Only later would he realize his mistake, which often involved extra costs or missed opportunities… and conversations with people to apologize for what he had done.

People began to see the urgency as insecurity and a lack of confidence, which damaged his credibility.

But mostly it was a lot of wasted hours by the team, which was demoralizing.

If you’ve ever been in a situation where your boss is causing more harm than good, here are a few suggestions.

You could leave my business card on their desk – the one that says, “Do you have a terrible management style? Call Shane.” But this might not go down too well.

Alternatively, there are several things you could do to help the situation:

1. Recognize what’s important to them.

Assume leaders have good intentions, and then figure out the positive reasons for why they’re behaving the way they are.

In the case of Martin, he felt a powerful need to move with speed and decisiveness. He had a strong sense of urgency. He wanted to get things done fast.

2. Before you push back, acknowledge their need.

When leaders know you know what’s important to them, they won’t feel the need to push so hard… which makes it more likely they’ll hear you out.

If I had Martin as a boss, before giving my opinion I’d use a phrase such as, “Hey, I understand this is something really urgent for you.”

3. Link what they want to the opposite approach.

When a leader is out of balance in a particular trait, bringing in the opposite trait can often help address the imbalance.

Martin’s team knew rushing into action could cause him to miss critical details harmful to the outcome. The opposite approach here meant slowing down and deliberating a bit more.

A little pause for thoughtful reflection could actually speed up the results Martin wanted.

After acknowledging Martin’s sense of urgency, I’d say something like, “I can see this needs to happen NOW. I think if we have a brief strategy meeting and ask a few stakeholders for input, we can plan the fastest way to get this done.”

The phrase starts by agreeing with Martin’s objective, and ends with how my suggested slowdown ultimately supports his objective of getting it done fast.

4. When appropriate, tactfully explain the impact the leader is having.

When the leader’s trait is having a negative emotional impact, it’s a good idea to tactfully draw attention to the consequences of their approach… because they’re often oblivious to it.

For example, here are two things I could say to Martin if he’d just interrupted me. One of them is more tactful than the other. See if you can figure out which is which.

(a) “I know you’re often ahead of us in your thinking. But when you interrupt me, I don’t get a chance to participate and contribute in a way that adds value.” 

(b) “I’d like to be part of the solution you want to create and think I can help.  I need just an extra beat or two to complete my thought.  Is that ok?” 

(b) “Hey!...stop interrupting me, you moron.”

In the end, the most effective long-term strategy is to help leaders recognize for themselves where they’re out of balance in a particular trait.

You could point leaders to my 7 Management Polarities quiz or my latest book, which is a tactical handbook for leading teams and understanding your management style.


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How to Disagree without Being Disagreeable