The Most Avoided & Desired Coaching Conversation

One topic comes up over and over again during hybrid coaching. In fact, every single person I have ever coached at one point brings up this subject. Age, gender, and experience are irrelevant…all want coaching on the same thing:

How to have a difficult conversation.

The conversation could be with a co-worker, spouse, boss, friend, member, sibling, or any other iteration of some kind of relationship. People want to express themselves. Often, they don’t know how.

I’ve discovered two things in my short presence on this planet: 1) people will go to great lengths to avoid tough conversations, and 2) one of the greatest human desires is to be understood.

What is a difficult conversation anyway? I believe at the root of every tough conversation is a value. Rather, a value that has been violated. Perhaps trust was violated when a boss took over a delegated project or respect was violated when a co-worker gossiped. There are many values unique to each individual. We often don’t want to talk about values because we get them confused with feelings and there is a societal norm that feelings don’t belong in the workplace.

There is a huge difference between a conversation that starts with, “you really made me mad when you…” versus “I really value respect and want to have a respectful working relationship with you”. Talking about feelings can often trigger defensiveness. Talking about values can foster understanding.

But when did we learn the difference? Did you take Conversations 101 in High School? Have you had any formal training on how to express a concern effectively? Or how to listen from a place of empathy? More likely than not, you and I have learned the same way: through the school of hard knocks.

I think a lot of us are so afraid of getting a tougher conversation wrong we become unwilling to try. I’ve heard many rationalizations over the years:

“I can’t give my boss this feedback because she will retaliate against me” 

“Who am I to tell my co-worker that, I’m not his supervisor”

“I don’t know what to say. I need to create a script before I say anything”

I’ve observed a tremendous amount of pain and suffering that comes from waiting to have an important conversation. The biggest consequence: resentment.

Resentment is like swallowing poison and waiting for the other person to die. 

I believe this is why it’s important to have corporate coaches. When a third party can skillfully support the attainment of a goal, like having a conversation, positive results will follow. Coaches can create safety to discuss values. Coaches also create accountability for getting the right results.

One of my favorite questions to ask someone I’m coaching is, “how will I know you’ve done it?” I find that one question gets more results than six hours of class. Most people want to work in a thriving culture. People want to be inspired. People want to be happy. Sometimes it just takes a little push.

The one thing we do all day long is converse. Interact. Work together. Conflict is bound to happen. If conflict can be viewed as an opportunity to make a team stronger, imagine what could happen to our culture. If every person felt understood, there wouldn’t be so many struggles to be heard.

So what conversation should you have today?

And how will I know when you’ve done it?


Regional Finalist – West