Changing... yourself for difficult conversations

© 2024, James McLean

Those challenging interactions that require us to adapt and evolve are as much about transforming ourselves as they are about influencing the person we are engaging with.

What was the first really difficult conversation you ever had to initiate?

I remember mine very clearly.

I was a young finance company branch manager who had an older employee in my branch. This older employee was a Vietnam veteran. I don’t know if that was the sole reason for his drinking during the day, but it did contribute to it. I was in my late 20’s, and he was 40ish (I can’t remember his exact age, honestly.) He was a charming person. He took me under his wing and helped me a lot as I settled into my new role.

He never seemed drunk, but he often forgot details. For example, he often forgot to get loan contract clauses initialled properly – these would mysteriously appear after I pointed it out. And I always wondered who had signed them! But it was the accumulation of small vodka bottles in the men’s toilet rubbish bin that eventually made me put two and two together and decide I had to raise the topic.

I didn’t want to hurt him. I didn't want to damage the good working relationship we enjoyed (other than the issue of potentially fraudulent contracts that I was responsible for!). I didn’t know what words to use to open the conversation. I didn’t really know what outcome was reasonable. I didn’t want to appear young and naïve about my expectations of him as one of my staff members – he had years more experience than me!

I had to change. I had to assume my relatively new role of authority and use it to protect the interests of my employer and other staff members. I also wanted to help this employee if I could.

Because I was unsure, I opened the first conversation very quietly and softly. I sugar-coated my message, and it didn’t get across in the first attempt. This was when I learned to use my natural directness, but also that these conversations can be a process of trial and error. We don’t always get it right the first time.

I tried again, with greater effect this time. He laughed and said, “Oh, so that’s what you were trying to say before!” I learned that he was, in fact, an alcoholic. I had zero idea what to do with that. But eventually my manager intervened – my manager had employed this person in the first place, and they were personal friends. The plot thickens. Another difficult conversation – upwards this time.

Gradually, I learned to speak up clearly because this is the only way. I also learned to listen with empathy and act with compassion. I learned about the importance of protecting myself too. I grew up considerably.

Within the context of my leadership development work today, I now understand that difficult conversations are difficult because they are adaptive conversations. They demand that we:

  • Accept how we are likely to be fuelling the very issues we are concerned about perhaps by tolerating the poor behaviour or whatever, for too long.

  • Take responsibility for the role we are paid to fulfil.

  • Attempt to help the other person take responsibility and change what they are doing.

  • Follow through until we come to a resolution.

I’ve also learned a lot about difficult conversations from my executive coaching over the past 25 years. I initiated these conversations with some clients and helped others prepare for conversations that they needed to initiate.

What was your first difficult conversation? How did you change … yourself for difficult conversations?

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