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Having Difficult Conversations: A Primer for Leaders

In my career, having difficult conversations with my team members was always tricky. I coded these conversations as conflict. And conflict is something I’d almost always prefer to avoid. Early in my career, I could work around it. I didn’t lead people. My worst case was challenging customers. And the companies I worked for were very focused on keeping clients happy, so problems quickly got resolved.

manager having difficult conversationsThen I found myself leading people—initially, salespeople, then multi-disciplinary teams, and eventually whole divisions and businesses. And the more people I had, the more I had to address performance issues. And I was not great at it. First, I didn’t confront them at all. I was vague or more cajoling than challenging. And that was if I didn’t just avoid the conversation altogether. And you can imagine how that all worked out for me. Short version – not very well. 

I knew it was time for a change, so through study, coaching, and intent, I developed a plan to have difficult conversations with team members. I have five rules for having difficult conversations with members of my team.

  • Be Timely
  • Be Objective
  • Practice Active Listening
  • Focus on Solutions
  • Include Accountability

Be Timely

When I was struggling through having challenging conversations, my boss noticed. He sat me down one day to talk about it. And my biggest takeaway from that conversation was the phrase “problems don’t age well.” And, they don’t.

When you see someone on your team doing something wrong, you may be compelled, as I was, to think: ‘it’s just an anomaly. I don’t need to address it.” Worse, when it repeats, you may allow them to work it out for themselves, hoping they will get better. They won’t.

In every case, you are better off having a conversation with your employees at the first sign of poor performance. I’m not suggesting you come down like a ton of bricks, but address the issue. People want feedback, and it is far more effective when they get it at the time of the problem. (This also works well with catching people doing something right and complimenting them.) 

Be Objective

It is so important to approach these conversations objectively. Having difficult conversations can be hard enough. You don’t want to layer them with assumptions.

It is best to open these conversations with phrases like: “I’ve observed” or “based on what I have seen when this happens.” You don’t want to start these conversations with assumptions that immediately put your employee on the defensive. 

Keep the conversation objective and stay to the facts of what you have seen or observed.

Practice Active Listening

Active listening means you are paying attention to the conversation. You’re not half-listening and planning your response at the same time.

After you have laid out your observations, ask the team member for their perspective on the issue. You don’t know why they’re doing something wrong. They may be thinking they’re doing it right. Assume positive intent.

And, as they’re outlining their experience with you, pay attention. Look for body language and verbal indicators (sighs, nervous laughs, and tone). Listen to their words. Once they have explained it from their perspective, then your can respond.

It may feel weird to you at first but start by rephrasing what you heard from them. “So what I hear you saying is….” Then close with “did I get it right?” Correct as needed and then move to the next step.

Focus on Solutions

Once we have everything out on the table, we can determine what the solution needs to be. And this can be a variety of outcomes, from more training to changing their approach. What’s important is that we don’t dwell on the problem and focus on moving forward. 

At this stage, we are looking for a win-win outcome. How can I get what I need as the leader (more productivity, increased effectiveness, fewer errors)? And let’s get the win for the team member, too (more confidence, better satisfaction, and no more of these conversations).

Include Accountability

There is an old Russian proverb: trust but verify. Accountability is how we do that. After your conversation, you want to create a framework to determine that the employee follows the agreed-to solutions.

Don’t leave the meeting without accountability put into place. If the problem is a sales rep making cold calls, set a follow-up meeting to review that performance. If it’s showing up to work on time, agree to check every day for a period of time to ensure they are getting it done.

People perform on what is measured. So you have to measure against the solutions. If you don’t, your conversation means nothing, performance doesn’t change, and you undermine your credibility.

So, there it is—my formula for having difficult conversations. I encourage you to give it a try the next time you see an employee struggling to meet expectations. And let me know how it works for you!

Do you need help to transform difficult conversations into growth opportunities? Let’s address this together. Schedule a Clarity Call with me and learn how to use personalized strategies to enhance your leadership in challenging dialogues. Whether fine-tuning your approach or developing new techniques, this one-on-one session is your gateway to becoming a more effective, empathetic leader.