Secret #3: Learn how to manage hard conversations

Taken from “10 Secrets To Empowering Teen Leaders,” this one asks you and your teen leaders not to shirk the hard conversations

This is a hard lesson, and one my students are only beginning to do well — in part because it’s at the edge of what I myself have learned.

One of the biggest downfalls leaders experience lies is their inability to face someone who is screwing up.  They choose passive aggression (snarky comments) or gossip (talking to everyone else) in order to initiate change.

Recently, two of my editors presented a new publications policy to the school board.  As part of the presentation, they each discussed several values they had gained in their jobs.

My junior editor chose to discuss the way the staff was handling deadlines.  It’s been a problem in past years, because reporters were simply assigned a deadline, which most of them missed consistently.  There was little follow-through. This year, they tried something different.

Each day, my editor reported to the board, our managing editor made a habit of checking in with each reporter, seeing how each story was coming.  If a reporter was running late, the managing editor listened to the excuse, but then probed with more questions, boring in on the real problem. Talking about it, addressing the root cause, they found a solution.  Not surprisingly, for the first time, our reporters had begun finding success in meeting deadlines.

These conversations were difficult, my editor said.  But she had learned their value.

Of course, so had I.

Leadership is about learning how to approach things directly, to initiate the difficult conversations that most people prefer to avoid.  If you’re sensitive — as you also need to be if you’re going to show people you care — these can be difficult to confront. Most people choose a pattern of avoidance.  Which is why most people aren’t leaders.

I recognize this pattern because I’ve fallen prey to it in the past.  I remember directing my first professional show in North Hollywood. I had hired a volunteer stage manager, “Leona,” whose methods, I soon learned, didn’t match mine.

I quickly grew unhappy with her.  She didn’t have a lot of experience, and she didn’t match the previous stage managers I had worked with.

But rather than having the confidence to sit down with her and constructively solve the problem, I chose another path.

I looked across the table at my new friend, “Kylie,” the woman who was playing a leading role in A Tale of Two Cities.  Her eyes were sympathetic, but also focused.

As I sat there, I was also a little uncomfortable.  Moments before, Kylie had cut to the chase. She had noticed how uptight I felt, she said, how out of control the show seemed to be going.

“Remember when you were adjusting the carpet during rehearsal?” Kylie said, her voice sympathetic but authoritative.   I nodded. She went on with her analysis. “People do that when they don’t feel in control. They change small things.”

I gaped at her, amazed at her insight.  That’s exactly how I felt.

“How can I help, Steven?”

I looked away, touched by this actress who understood my frustrations.  I thought about the problems I was having with my stage manager. In my mind, I compared the two women.

Of course, I hadn’t actually talked to Leona about the problems I saw.  I was exhausted, just trying to deal with the day-to-day issues. I was hoping Leona would figure it out on her own, sort of by osmosis.  The smart leaders I knew did that.

If only she were like Kylie.  My leading actress was organized, hard-working, and knowledgeable about everything in the theatre business, everywhere.  She had directed, acted, and stage-managed in previous shows. She was a veteran. If she were stage manager, she would have things under control.  Not like Leona.

The problem was, Kylie was also playing a leading role.

Perhaps she could do both.

It was then I made my fateful mistake.  I glanced back at Kylie.

“Do you think you could play the role of assistant stage manager?  I think Leona needs help.

The problem was, it wasn’t Leona who needed help. It was me. That became clear as confusion and anxiety swept through the cast.

My new lead/assistant stage manager worked to solve problems, but since I hadn’t bothered talking to Leona about what I hoped to gain from the change in leadership, the show quickly became a three-ring circus.

And we weren’t staging a circus.

Kylie gave orders on stage, while Leona struggled to figure out why she wasn’t in control anymore.  The rumors flew widely.

And it all came down to my inability to initiate a hard conversation.  It was an unhelpful way to work, and certainly not the way to lead.

Things went from bad to worse, drama increasing with the gossip.  It was about then my stage manager called me several hours before a rehearsal.

“Steven, do you have a minute?”

My heart sank.  I was hiding out in a cafe, not far from the theatre.  I was hoping all this would blow over.

“Sure, Leona.”

I heard her take a deep breath.

“I don’t get what’s going on.  Why have you turned Kylie into the stage manager?  She’s supposed to be playing the leading role. Everyone backstage is confused.”

“I guess I thought you needed help.”

“Steven, I don’t get it.  When I took on this role, you told me you believed in supporting your stage manager.  Yet … that’s not what I’m feeling.”

By now, I had gotten out of my seat, the cell phone to my ear, pacing outside the cafe.  I stared at the line of cars driving by, the endless traffic. I heard something click, and I made a decision.

“You know what, Leona, you’re right.  This is my fault.”

We talked for about 40 minutes, Kylie and I, and by the time we were done, we had straightened out the lines of communication.  I had expressed my concerns, she hers.

But why did it take so long?

The answer is simple:  I wasn’t willing to initiate the hard conversation.

After that conversation, my work with Kylie became more productive, but the cast never completely recovered from the atmosphere of distrust I had created.  And, of course, the show received mediocre press reviews.

I’ve always wondered what would have happened if I had earned the respect of my stage manager and the cast by initiating the hard conversations we needed to have.  Would things have been different had I built a relationship of trust between my leaders and myself?

I suspect so.

Ten years later, it was my wife who offered me the key to having difficult conversations.  

You need to prepare deliberately for the conversation, she told me. This means you need to identify your own emotions — your anger, frustration, humiliation — whatever you are feeling in reaction to the behavior of those who are following you.

If you are an external processor, you may need a confidante who is not involved in the situation, and thus has no emotional stakes in the outcome.  Talk it through. How do you really feel?

Then decide what emotional and objective goals you want to achieve.  Do you want them to change their attitude? Is there a particular behavior they can change?  Have you decided you need to move them to another team where they can be more effective? This is the time for you to be utterly honest — with yourself.

Once you’ve decided on what you want, then you can develop a plan to help everyone find their way to the same place.  This requires strategy, not simply letting your emotions dictate what you say. Most likely, you won’t have the luxury of telling them how you really feel.

On the other hand, if they need to see you differently, you may need to be vulnerable and let them know how hurt you were by their behavior.  If they respond to this, or if you can see potential for change, you can create together a step-by-step improvement plan you can both follow.

You won’t learn to do this overnight.  So plan a strategy you will follow each time you need to have a difficult conversation.  If you do this well and the team sees you can be trusted to tell the truth, even when it’s hard, you will build a productive relationship of trust and respect.

And if you’re committed to it, if you’re willing to model the difficult conversations with your students, if you’re willing to talk about the process with them — you can strike that balance.

You will also be showing them how to do the same.