Difficult Conversations: What Every Leader Needs to Know


Difficult conversations -- We’ve all had ‘em….  

  • Parting ways with a startup partner
  • Easing tension between two team members who are blocking progress
  • Encouraging a patient to change a stubbornly-held habit in order to heal
  • Talking with a teen who’s hanging with a dangerous crowd
  • Clearing up a deep-seated misunderstanding between two managers

What I see in my work with organizational teams is that these kinds of conversations are inevitable. And it’s up to you, as the leader, to take the helm in creating an environment where they can take place to clear misunderstandings, build trust, and free-up a roadblock to productive work.

Now, who in their right mind wants to have a difficult conversation? Right - no one! So what we tend to do is avoid it, put it off for a day, a week, even a year. But does the issue go away? No, in fact it festers and grows until it becomes something more destructive and even dangerous to the organization. Conflict in this form cannot be swept under the rug!

Let’s reframe the concept: "having meaningful conversations"

Never underestimate the importance of conversation. Lots can be resting on conversations -- moving a team agenda forward, negotiating a contract, setting long-term business strategy, building a sustainable partnership, literally getting a job done.

The flip side of difficult conversations is having meaningful conversations. Try reframing how you look at a conversation, ‘good’ or ‘bad,’ to see it proactively as a powerful business tool.  When you approach any conversation, ask yourself: “How can I have the most impact with what I need to say?”  

You want to create a workplace culture which invites meaningful conversations, allows both sides to be heard, maintains trust and respect, and moves the parties to an acceptable solution. The result?  A strong team that can exchange ideas effectively, disagree healthily, innovative creatively, be productive, and get stuff done!

Practicing how to have a meaningful conversation

The exercise I’m about to describe is a piece of a more comprehensive workshop we offer on-site to leaders and teams. It’s designed to help prepare for the tough conversation, or any other kind for that matter, BEFORE they happen, so you’re ready to engage instead of avoid.  Once you become familiar with it, you have a formula to use to make every conversation meaningful and productive. The exercise and theory behind it is based in both Non-Violent Communication (NVC) and "Difficult Conversations" the book by Stone, Patton and Heen.

The key is building trust within your team by getting close and personal - yes, even emotional. Corporate culture by nature doesn’t like getting too close. Yet sometimes you have to ‘go there’ to get to the emotions behind what’s being said. Risking a little vulnerability as a leader can bring great return - the strong, effective teams I described earlier!

Positive Feedback Conversation Exercise / Formula

The formula is the same for any meaningful conversation, so the idea is to practice on a not-difficult conversation first.

The Exercise Set-up:
In a facilitated team setting, pair-off your members, preferably randomly, and have them meet in separate parts of the room. Ask each person to take 5 minutes to think of and jot down something they want to say to their partner that is positive, i.e., project well done, contribution to a meeting, talent or skill they displayed. Using the conversations formula noted below, Partner #1 will share for 5 minutes with Partner # 2 the following (and then switch).

The Conversations:

1. Here’s what happened conversation:

  • Description of what happened, without judgment. “You delivered this project on-time.”
  • Here’s what I saw from my perspective:  “The client called and had this positive reaction. As your boss, you made me look good in front of the client, and I’ll likely get a bonus and maybe you will too.”

2. Here’s why it really impacted me on several levels (it can get deep, really fast). The feelings and identity conversation:

  • “This was a really important project to me because it’s the first one since I took this position. I have a new baby on the way, and I need this job to last. I'll feel safer in my job now because of this and that feels awesome!"

  • "Your work goes a long way to helping the poverty situation in our community which is so important to me because....”

3. Make an ask for continued similar behavior or a change in behavior. The problem solving conversation:

  • Start an open negotiation, or, as a boss make a demand. In this exercise it may be that you are asking for more of the same. In a difficult conversation it may be that you are asking for change.

4. Once you have finished the three parts above in pairs, come back as a group and talk about what just happened. Explore the idea of practicing the same exercise but this time with a group example of a typical difficult conversation. 

As you might imagine, when this exercise is carried out in the spirit of mutual respect, intention, and trust, it can be really impactful in several ways: practicing having a meaningful conversation, building interpersonal relationships, boosting positive feedback, and bonding a team in celebration.

It’s wise to bring in a professional to facilitate this exercise, because it can be deep and powerful, and things may come up. And, as I’ve seen, a lot can be accomplished in a short period of time in this facilitated atmosphere.

Having (or running from) difficult conversations in your workplace? Contact Resologics about this and other constructive conflict issues at mark@resologics.com  or 510.314.8314.