Why Leaders Struggle With Difficult Conversations and How to Fix It

I am really struggling with one of the managers I oversee right now. They are not getting the job done.

I hear this all too often. To which I respond, “have you discussed things with them and designed a plan?”

“Well, I told them they were not meeting deadlines, and it was holding the team back.”

My statement: “basically you said you’re not getting the job done, letting the team down, and no specific direction or deadlines?”

“Yes, sort of.”

Most leaders are not struggling with the person, they are struggling with the conversation.

Look, I grew up in the 90s and jumped into my career in the early 2000s, so I know all about these conversations.

They don’t cut it today.

Difficult conversations are a part of life and they don’t have to be so difficult. We can use systems and make them easier.

Early in my career, these awkward conversations took place all too frequently. In fact, I recall one conversation in which the supervisor called me into his office and proceeded to rip me a new one. He was displeased with the work of a direct report of mine. He didn’t have anything specific, simply didn’t like how the task got done. Commanded me to go talk with her immediately.

What he really wanted was emotion, not leadership.

Did I rip her a new one? No. She completed the tasks exactly how I had discussed with her that morning, and she even asked about adjusting the route to make it slightly more efficient. I agreed.

I was not prepared for this and awkwardly sat there trying to formulate a sentence. After she listened, she asked, “isn’t this exactly what we said we’d do?”

I said yes, you know, it is. You just keep doing what we discussed and we’ll catch up later.

I quickly hustled to my office to put together a plan. I knew I’d have to report back to my supervisor and he was already frustrated. I needed a plan because we not only did right, we put together a maintenance plan for the day that was better than his old school ways, yet different than what he was used to.

That moment taught me that preparation is not optional, it is leadership.

The keys to making this difficult conversation better were simple:

  1. Prepare
  2. Clearly stated objectives for the day
  3. Clarity in plan and operations
  4. Prioritize
  5. Set deadlines
  6. Follow up and feedback

Now, he knew what the plan for the day was because he asked. You know what else happened though?

Life.

His wife called. Issues with the kids. His supervisor got frustrated with him since he had to leave for a while and come back. By the time he returned, he didn’t even recall the plan we discussed.

I followed the six steps above and peace followed.

Hands down the number one issue: people do not prepare for difficult conversations. They walk in with an item or two on their mind where they feel wronged rather than tangible material that shows the effect on the team or service.

After we prepare, we are able to discuss objectives, a plan, prioritize duties or steps, set clear deadlines, and follow up with each other.

This allows us to move in a positive forward direction, together.

Key word, together.

As we unify and grow together, we accomplish so much more.

These six steps are exactly what I will be teaching in this week’s webinar on difficult conversations.

If you want to lead difficult conversations with confidence instead of frustration, I’m here to help. DM me and let’s get started designing the right fit for you.


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