Courageous Conversations

I’ve noticed a pattern emerging with a handful of my clients. Each situation is unique, but the commonality lies in their relationship with their boss. For various reasons, the client is uncomfortable giving their boss feedback.

These are challenging situations. The client’s performance or personal brand often takes a hit because of the boss’s behavior, yet the client feels powerless to broach the subject and generate a shift. I have a few stories I often share with clients that can inspire them to find a way to deliver feedback. I want to share those stories with you today.*

The First Story

In the first story, I had a peer who was underperforming. He was a good person but wasn’t the right fit for the role. I and other leaders waited patiently for my boss to recognize the issue and take action. Only he didn’t do so.

Over time, managers became frustrated with the situation. Several came to me to express their frustrations, presumably because my leadership style created a psychologically safe space for them to share openly. As this began to bubble over, I realized we were not sharing this feedback with my boss. Upon reflection, I’m not entirely sure why. I don’t think my boss created a psychologically unsafe environment. But perhaps he was intimidating. Maybe it was just our culture that made us feel uncomfortable giving that kind of direct feedback.

I remember the day I summoned my courage and sat down with my boss. I expressed my concerns about my peer’s performance, and my boss acknowledged there were issues. I wasn’t sure he was convinced. I leaned into the conversation and explained that his credibility with our leadership team was coming into question because of his inaction. I offered to run the peer’s organization while he hired a replacement if that was the barrier holding him back.

We had that conversation on a Monday. By Friday, my boss had let my peer go. Thankfully, he only asked me to lead half of my peer’s organization. When my boss and I talked afterward, he shared that he knew he had an issue with that leader, but he felt it was a lower priority than so many other issues he was dealing with. When I offered my candid feedback, he said it was as if the walls he had built up around taking action crumbled away. He was grateful for my feedback, and our organization was better as a result.

The Second Story

In the second story, our company was in a crisis. We were approaching the end of support for the current version of our software, yet most of our clients had not yet moved to the newer version. It was April. Support ended at the end of the year. Only 10% of our clients had moved. It was going to be a long summer.

We expected to take two teams of developers and put them on customer support for the entire summer to help deal with the customer demand. One of my managers had the courage to offer me feedback. He told me his team was ready to pivot to support, but they wanted me to lead the migration if they had to do that. That manager’s courage helped melt the walls I had about taking a leadership role.

At the time, we had five directors leading the migration by committee. It was a challenging structure. Encouraged by my manager, I made a request to my boss. I wanted to run the migration personally. I asked him to give me full responsibility within development and across all company areas. The Executive Team embraced the idea, and suddenly, I was in charge of the most critical project in the company.

I remember one of the executives telling me I’d be lucky if we ended the year with 100 clients that had not migrated. We finished with 45. We also expanded that concept into a strategic program framework that we used successfully to improve cross-organizational collaboration across several strategies.

The Third Story

The first two stories are some of my most inspiring examples. The third is a counter-point. Later in my career, I had the most challenging leader of my career. This leader did not create a psychologically safe environment. Quite frankly, I never figured them out. I saw many behaviors that would dramatically improve their success if the leader could address them.

One day, I summoned the courage to offer this leader feedback. I sat down with the leader and opened the conversation carefully. “Can I give you some feedback?”

Their reply leaves me stunned to this day. “You have to earn the right to give me feedback.”

So they got no feedback. I felt shut down and disempowered. I loved the company, the people I worked with, and the clients, so I still put in a lot of effort, but I was never my best self under that leader.

Making Meaning

The first two stories are what I tap into when I need courageous authenticity. This is one of my favorite competencies, as identified by the Leadership Circle Profile. Here’s how they define it in their brochure:

Courageous Authenticity measures the leader’s willingness to take tough stands, bring up the “undiscussables” (risky issues the group avoids discussing), and openly deal with difficult relationship problems.

In all three instances, I shifted out of my comfort zone, resisted my desire to be conservative, and leaned in with courageous authenticity. In the first two, I get beautiful results. In the third example, not so much. Even in that third example, I felt better having made the attempt.

If there is a courageous conversation you need to have, and you’re not having it, how can you tap into your courageous authenticity? Think back to when you demonstrated that courage and had a successful outcome. Tap into that experience to motivate and inspire you to have a difficult conversation. A coach can be invaluable at this time, giving you a safe, confidential space to try out different approaches and decide how best to engage in the conversation.

In that third story, the challenge with the leader boiled down to psychological safety. Others and I recognized that speaking up and demonstrating courageous authenticity was unsafe. It could get us fired or damage our careers. I’ve coached leaders with bosses like this. In most cases, the leader either outlasts the difficult boss or decides they can no longer tolerate the culture and finds a new opportunity elsewhere.

If you don’t feel safe having a direct conversation with a leader, look for someone in the organization who can create a psychologically safe environment that you can talk with. In my first story, frustrated managers came to me because they felt safe doing so. I was able to aggregate their feedback and bring it to my boss in a compelling way. Look for a trusted, confidential contact in HR. Look to another leader in the organization you trust for guidance. When all else fails, consider whether this is the right role for you.

Putting It Into Practice

Here’s how to have more courageous conversations:

  • Reflect upon the challenging situations in life where you feel you should be having a courageous conversation.
  • Consider how psychologically safe your relationship is with the leader.
  • Embrace courageous authenticity – the willingness to discuss a difficult topic openly, even if it’s an unpopular position.
  • Tap into your past experiences of courageous authenticity as inspiration.
  • Seek guidance from other trusted leaders or HR if the environment isn’t psychologically safe.

I am an executive coach and life coach with software executive roots in higher education and EdTech. I coach because I love to help others accelerate their growth as leaders and humans. I frequently write about #management, #leadership, #coaching, #neuroscience, and #arete.

If you would like to learn more, schedule time with me.

Want to comment? Join the conversation on LinkedIn.

* In delightful synchronicity, a potential client asked me to share one of my most proud leadership moments the same day I planned this blog post. I told her it was a timely request, as she would see me share that same story in next week’s post. I hope she’s reading!

Subscribe to Arete Pursuits