Leadership Dispatch

Handle the Hard Conversation

Two community service colleagues having a thoughtful, private conversation in a quiet room.

Post #32 | Application in Practice

“The conversation is the relationship.”

Susan Scott, Fierce Conversations, 2004

There is a hard conversation you have been avoiding. As you read this, you probably know exactly which one it is. You may have rehearsed it in your head more than once, and replayed every possible response from your words. Though it has not occurred, It is already shaping the relationship, just quietly and in a direction none of us would choose.

Susan Scott’s idea that the conversation is the relationship means every talk we delay, soften, or skip is still doing something. In Post 15 we walked through how to prepare for a difficult conversation. This week we look at the relationship underneath it, and why the conversation is worth having even when our voice shakes a little.

A Moment Worth Paying Attention To

Hard conversations are focused on in self-help books for a reason. They are challenging and have great potential for both good and bad. I learned this in a great way when I was a young leader in the 82nd Airborne Division.

As a “good” NCO (Noncommissioned Officer), I sought to help all of those I led to grow into highly capable and functional future military leaders. One specific soldier, I will call Jody (if you know you know) was a significant challenge. He did not do well at physical training, he barely qualified with his weapon, and he barely passed all our timed runs and ruck marches. In a typical “Airborne” approach, I turned up the heat and he still dod not respond at all. He stayed the same.

I knew that I was going to have to engage him, but I also felt that doing so would result in his removal from our team and most likely his reassignment. I did not want that for him, and to be honest did not want it to reflect on my leadership. So I avoided it and kept on with the same methods that frustrated me and Jody.

Following his falling out of our formation in our annual Division Run, I was called into the Seargent Major’s office with Jody. After a typical verbal chewing on us both, I was asked to stay behind. When asked what the issue was, I immediately began laying out all the “dynamic” leadership I had provided to no avail. My Seargent Major asked a defining question in response, “Have you asked if this is what he wants to do?”

You see, being on airborne status in the military is an option one must volunteer for. Many step into the position not understanding it fully and regret that. When I forced myself to sit down with Jody, I found that he did not like the position, the unit, or the whole jumping out of airplanes thing. He said he wanted to do what he can, bit he is not interested in progressing as a leader in our unit.

Following the conversation, I was able to get Jody reassigned to a unit on the same post that did not have the same requirements. He loved it and thrived. Jody’s replacement, a transfer from the same unit he went to, was a rockstar soldier that went on to be very successful in the 82nd.

My fear of a conversation for the wrong reasons kept a team member where he did not belong or want to be and unknowingly kept another in the same position. All because of my fear as a leader. I learned how important hard conversations are through this situation and today feel that the more difficult a conversation, the more urgent it is.

Why We Avoid It

Most of us avoid hard conversations for reasons that come from a good place. We fear the conflict, we worry about how the other person will react, and we are afraid of getting it wrong and making things worse. I have paid my share of stupid tax on all three.

Avoidance has a cost that grows quietly. The other person fills the silence with their own guesses, and the relationship slowly runs on assumptions instead of honest words. Detert and Edmondson (2011) found that people carry taken for granted rules about speaking up that can keep them silent even in settings that are objectively safe. Their work looked at employees speaking up at work, but I suspect the same instinct follows us when we are the ones holding the truth.

Name the Real Topic

Before we say a word, it helps to separate the surface issue from the real one. The surface issue may be late documentation. The real topic may be that we have noticed someone pulling away and we are worried about them.

Stone, Patton, and Heen (2010) describe every difficult conversation as really three conversations happening at once: what happened, the feelings involved, and what the situation says about each person’s identity. When we only talk about the first one, the other two keep running in the background. Naming the real topic gives us a chance to speak to all three with kindness.

Open With the Truth

Small talk feels gentle, but it usually delays the moment and gives the other person time to brace. Consider opening with one honest sentence, something like, “I want to talk about something that has been on my mind, because I care about how things are going for you.” Say it early, then pause and let them respond.

Watzlawick, Beavin, and Jackson (1967) observed that every message carries two things: the content itself and a signal about the relationship between the two people. The way we open tells the person how we see them long before the facts do.

Stay in the Room

The hardest moment usually comes a couple of minutes in, when the other person’s face changes. That is when we want to soften the message, rush to the end, or find a reason to leave.

Consider taking a slow breath and letting the silence do some of the work. Staying means remaining steady and kind while the truth has time to land, and it tells the other person they are worth the discomfort.

Listen for What Is Underneath

A reaction often tells us more than the words that come with it. Frustration may be covering fear, and quiet may be covering embarrassment.

Many of those entrusted to our leadership carry stress and history we cannot see, so a strong reaction may have very little to do with us. Consider asking, “What is going on for you as we talk about this?” and then listening without defending. What we hear may change what we need to say next.

Close With a Next Step

A hard conversation without a clear next step just becomes a hard memory. Before we part, agree on one specific action, who will take it, and when we will check back in. Then follow up on that date, because that is where the person learns we meant what we said.

Practice on the Small Ones

Few of us handle the big conversation well the first time it matters most. Consider practicing on smaller ones, like a minor correction, an honest “I see it differently,” or a simple “I need something different from you.” Each one builds skill and trust, so the larger conversation does not feel like a first attempt.

This Week’s Challenge

Identify the conversation you have been putting off the longest. Write down the one honest sentence you have been avoiding, then schedule the conversation this week with an actual date and time on the calendar. You can do this, and do it well. Now let’s do this.

Reflection

What would our relationship with this person look like a year from now if we had this conversation today?

How has avoiding it already shaped the way we show up around them?

What will you do this week to say the honest sentence, kindly and clearly?

Lace up your Boots and Go Lead

You’ve Got This.

Suggested Reading and References

Detert, J. R., & Edmondson, A. C. (2011). Implicit voice theories: Taken-for-granted rules of self-censorship at work. Academy of Management Journal, 54(3), 461-488. https://doi.org/10.5465/amj.2011.61967925 Research showing that people often stay silent because of unexamined rules about speaking up, even when a setting is safe.

Scott, S. (2004). Fierce conversations: Achieving success at work and in life, one conversation at a time (Rev. ed.). Berkley Books. The source of this week’s opening quote and the idea that each conversation builds or weakens a relationship.

Stone, D., Patton, B., & Heen, S. (2010). Difficult conversations: How to discuss what matters most. Penguin Books. From the Harvard Negotiation Project, a clear look at the what happened, feelings, and identity conversations inside every hard talk.

Watzlawick, P., Beavin, J. H., & Jackson, D. D. (1967). Pragmatics of human communication: A study of interactional patterns, pathologies, and paradoxes. W. W. Norton. The classic work on how every message carries both content and a message about the relationship.

Keep Going

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