Does it explode?

Difficult conversations in the workplace

Manager defusing a bomb through a difficult conversation

Having difficult conversations with your reports is an essential but often unpleasant part of being a manager. Based on my experience, these conversations can provide clarity and guide the way forward. This clarity can manifest in different ways:

1. Alignment between you and your report regarding what has been happening.

2. Understanding the root cause of previously unknown issues.

3. A breakthrough moment where your report is motivated and ready to address the feedback.

4. An acknowledgement from either party that the situation isn't working and discussions should focus on how to transition out of the business.

Two different conversations

I've had numerous challenging conversations with my reports over the years. Undoubtedly, with experience, it becomes easier to navigate these discussions. Here, I'll share two conversations that took place within a year of each other—one that I consider a failure and another that resulted in a breakthrough.

Womp

I had a report who I will call Henry here who had interpersonal issues with another individual in the organization, let's call him Mark. Henry seemed to have an inexplicable dislike for Mark, causing tension between them. Mark was progressing rapidly in the organization and was confident in his approach. For some reason, whether valid or not, Henry was bothered by Mark's approach to things. The situation escalated to the point where multiple people in the organization, including myself, noticed the uncomfortable atmosphere during meetings.

I approached Henry to discuss this issue, but I wasn't adequately prepared for the meeting, lacking a clear objective. Consequently, the conversation went nowhere. We continued to have multiple conversations about the matter during our 1:1s, derailing the meetings and frustrating both Henry and myself. Through the grapevine, I learned that Mark was considering leaving the organization due to the increasing awkwardness with Henry, which further fueled my frustration. Regrettably, my frustration started to affect my conversations with Henry, worsening the situation.

It wasn't until I facilitated a conversation between Henry and Mark, rather than attempting to address the issue separately, that progress began. During that conversation, they both expressed their feelings and perceptions, leading to a better understanding. Unfortunately, this story doesn't have a perfect ending, as Henry chose to avoid Mark rather than genuinely moving forward. I also realized that by bringing my own emotions into the conversation, Henry perceived me as favoring Mark, wasting valuable time on isolated discussions instead of uniting them to resolve the issue.

From this experience, I learned that as a manager, it is better to avoid becoming an intermediary in he said/she said scenarios. Whenever possible, encourage individuals to directly communicate with each other. When that is not happening, facilitate a conversation to address everything openly and determine a path forward together. Your role is not to bear the burden of every interpersonal relationship in the workplace, but rather to recognize when issues affect productivity and well-being and facilitate conversations to resolve or move beyond them.

Breakthrough

I had a report which we’ll call Marissa for the purpose of this scenario. Marissa had been rapidly promoted and had become the leader of a medium-sized organization. Her team admired her, and she excelled at executing the directions I provided. However, I noticed that Marissa seemed to have reached a plateau, lacking the proactive and strategic input necessary for further promotion.

I had a frank conversation with Marissa about this and explained to her what I was observing versus what I wanted to see. I articulated to her that I thought she had reached her current potential and that we needed to work on honing the skillsets described above (I could’ve been a bit more tactful here in retrospect).

While Marissa was not thrilled to receive this feedback, she became determined to prove me wrong. She wanted to demonstrate that she had more to offer and that she could grow beyond her current abilities. In the subsequent 1:1s, we delved into examples of what I expected from her, emphasizing areas where she could be more independent and strategic. Marissa astonished me by successfully driving numerous strategic initiatives, resulting in multiple promotions to leadership positions in larger organizations. This difficult conversation led to an extraordinary breakthrough and positioned Marissa for future growth.

How to tackle difficult conversations

As a manager, having hard conversations with reports can be uncomfortable and challenging. However, it's crucial to tackle issues as they arise to maintain a healthy work environment and ensure everyone is on the same page. Here are some tips based on my experience:

1. Be prepared: Before you have the conversation, take the time to prepare what you want to say and how you want to say it. This can help you stay focused and on track during the conversation.

2. Choose the right time and place: Make sure the conversation takes place in a private setting where you won't be interrupted. Choose a time when you and the employee are both calm and have enough time to discuss the issue.

3. Use clear language: Be clear and concise in your communication. Avoid using jargon or technical terms that the employee may not understand. Speak in a respectful and professional tone.

4. Listen actively: Give the employee the opportunity to express their thoughts and feelings. Listen actively and show empathy, even if you don't agree with their perspective.

5. Focus on behavior: When discussing the issue, focus on the specific behavior that needs to be addressed. Avoid making personal attacks or criticizing the employee's character.

6. Avoid emotional reactions: Leave any emotional reaction out of the conversation as it is likely to exacerbate the issue rather than helping you both get to a solution.

7. Offer solutions: Work with the employee to find solutions to the issue at hand. Ask for their input and suggestions, and be open to compromise.

8. Follow up: After the conversation, follow up with the employee to ensure they understand the next steps and what is expected of them. Set a timeline for improvement and check in regularly to track progress.

Does it explode?

Avoiding difficult conversations is never the right solution. While you may temporarily avoid awkwardness, the underlying problem will persist and eventually reach a breaking point. Trust me when I say that you will feel much better after having the conversation.

I’ll leave you with Langston Hughes poem “Harlem” which I think is relevant here (and in so many other cases):

What happens to a dream deferred?

      Does it dry up
      like a raisin in the sun?
      Or fester like a sore—
      And then run?
      Does it stink like rotten meat?
      Or crust and sugar over—
      like a syrupy sweet?

      Maybe it just sags
      like a heavy load.

      Or does it explode?

If you need assistance in preparing for or navigating difficult conversations in the workplace, do not hesitate to reach out.