Today I had a conversation with someone I have not spoken to in over 15 years. She was a friend who became an ex-friend after a perceived slight. I didn’t fully understand what I did so many years ago, but I moved on and gave up trying to make amends. So I was surprised when I received a message from her wanting to connect. We talked about our roommate who passed away and our shared grief at the tragic loss of a long-time friend. We broke the ice and began to reconnect as friends. If only we could have had this conversation 15 years ago.

What conversation are you not having?

Few of us have difficult conversations that are 15 years in the making, but whether it’s 15 hours or 15 years, holding on to a grievance against someone and giving them a chilly reception only deepens the problem. And like me, there’s a good chance the person is not entirely sure why you are treating them like a pariah.

What conversation are you not having?

It could be that you are dealing with an employee who is not performing as you would like. You grow more and more frustrated, and yet you find it hard to be “radically candid” about their gaps and need for improvement.

What conversation are you not having?

Perhaps you feel you have been passed over for promotion or have seen other people take credit for your work and ideas. Yet you have not found the courage to stand up for yourself and advocate for what you believe you deserve.

What conversation are you not having?

You may recognize your own situation in one or all of the above scenarios. And you probably know in your heart of hearts that your choice to avoid these conversations is having a negative impact on your satisfaction and fulfillment at work. In our work within organizations, we have found that poor or absent communication is at the root of most workplace issues. For one thing, we are constantly communicating at work, be it during group meetings, via email, one-on-one, on the phone, or in a messaging or collaboration app. That leaves plenty of opportunity for communication to go awry. In addition, we are all moving so fast these days and juggling so many things simultaneously that it’s easy for our communication to be misinterpreted and misunderstood. Nevertheless, having that important one-on-one conversation under uncomfortable circumstances is not easy, is not simple, and is probably long overdue. Hopefully not by 15 years!

When will you have the conversation you are not having? The first step is to get it on your calendar today. Next is to think about what your objective is for the conversation. What do you want this person to know, do, or say? What do you hope to convey? Then consider the other person’s perspective. Put yourself in their shoes and look at the issue from the other side of the table. What does it tell you about how to handle the conversation? What can you learn and what questions should you ask to better understand their viewpoint? How can you come from a place of curiosity and openness? And finally, think about what you can do to set up this conversation to be most productive. Where, when and how will you have the discussion? What other conversations will be needed? Often these are a series of conversations not just a one-time thing. When will you next talk?

Now that you know the conversation you are not having and when you will have it, take a deep breath, trust yourself, and go to it.

Even after 15 years, that’s all it took to have a conversation I needed to have.

What overdue conversation are you ready to have?
Click here to share.

If you enjoyed this post, you can read more like it in our book, The Power of Thoughtful Leadership: 101 Minutes To Being the Leader You Want To Be, available on Amazon.

For coaching support around having difficult conversations, contact Robyn at

Click here to receive The Thoughtful Leaders™ Blog posts via e-mail and receive a copy of “Ending Leadership Frenzy: 5 Steps to Becoming a More Thoughtful and Effective Leader.”

Photo Credit: Pathdoc/

New York: 212.537.6897 | Pennsylvania: 610.254.0244