How to Question Leadership without Seeming Confrontational | TechWell

How to Question Leadership without Seeming Confrontational

Team member questioning leader about the project plan

If I worked for you and I thought you were leading us in the wrong direction, would you want me to tell you?

One of the challenges we all face as our careers progress is finding ways to diplomatically disagree with people in power. Our first opportunities to screw this up are when we yell impotently at our parents as toddlers, “I don’t want to take a nap!” Some people never choose to mature beyond this level of protest.

As the rest of us gain wisdom and experience, we encounter a challenge: Sometimes, people in authority are wrong.

Good leaders sometimes make decisions based on incorrect or incomplete information, and when that happens, we have a professional obligation to encourage them to reconsider. However, correcting them in a confrontational way can be a career-limiting move.

Here are four factors to consider when standing up to those in charge.

1. Choose the time and place

If someone is about to cut the red wire on the bomb and you know it will kill us all, yell “STOP!” Saving everyone will probably earn forgiveness for your lack of decorum. Fortunately, most business contexts aren’t so fraught. If you believe a leader is making a poor choice, see if there is time to make your concerns known privately. This approach saves face for everyone.

2. Ask, don’t declare

If someone has publicly committed to a course of action, directly challenging them can be perceived as an attack on their person or authority, not just on the decision. Consider the difference between, “We don’t have the resources to do that” and “What resources will this take? Do you think we have enough?” The first is challenging; the second encourages conversation.

3. Get permission

Sometimes it can be hard to tell if a decision is open to discussion. A clever tactic I’ve learned is to ask, preferably one-on-one, “If I had concerns about this course of action, when would you like to discuss it?” This can be a dangerous challenge in a room full of people, but one-on-one it is an invitation that is usually welcomed.

4. Be polite

I find framing concerns in terms of risk can sometimes ease the conversation. “I can try to do this with the assigned team, but without X resources, there is a risk of not meeting your goals.”

In a meeting the other day, there were half a dozen of us working with a smart leader who was trying to arrange essential five-day training for key team members. She knew that she could only spare them for class one day per week and was frustrated by how much this was delaying the class. She had an idea: “Could we ask people to come in on a Saturday so that we could compress the timeframe?”

Her trusted lieutenant replied deftly, “If you ask them, they will come in on Saturday … but is this a good use of one of your wishes?”

This is a gentle and brilliant pushback I will add to my toolkit.

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