Tough Questions: Go Ahead and Ask Them 

For this article by Jo Ilfeld, Executive Leadership Coach on asking tough questions the image shows two women sitting across the table from someone else engaged in a deep discussion.

Asking tough questions is not easy.

When working with teams, one of the most important things to do is to open up a discussion where everyone’s voice is heard and make sure that everyone weighs in.

This often means delving into uncomfortable territories or posing tough questions.

Oftentimes when this happens, someone will say something inflammatory or something that is sort of a no-no or an undiscussable in the team, and you can often feel the tension when that gets said.

However, I’ve come to realize that within teams, the willingness to ask challenging questions and engage in candid conversations is crucial, even if it leads to discomfort.

What I find is that many leaders shy away from asking the tough questions because A, they don’t know how other people will take it, and they’re a little worried, or B, they do know how other people will take it, they know other people won’t agree with them, and they don’t want to hear that misalignment between others and their team.

Instead, they opt to pursue their agenda without opening the floor for diverse opinions.

In my experience, however, people generally feel better after having expressed their views than they feel if you just rolled over them with whatever it is you wanted to do.

So, here’s the challenge: Commit to initiating at least one discussion this week that you’ve been avoiding. Embrace the discomfort and the potential for growth that comes with it.

Remember, more knowledge, even uncomfortable, helps you proceed in a  much more thoughtful manner even if you still do what you were going to do.  It helps you take into account other perspectives and maybe just allow for them in newer, different ways that you wouldn’t have even thought of had you not asked the tough questions.

Want to learn how to make clear requests? Read more here.

Jo Ilfeld, PhD

An executive leadership coach, Jo helps C-suite leaders, executives, and high-potential managers develop the flexibility, skill, and frame of mind to meet the challenges of the next five, ten, twenty years…. and beyond. She works with individuals, teams and organizations on four core areas of leadership development. Check out Jo's bio page for more information.

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