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How to have those inevitable difficult conversations

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When presented with a difficult conversation, have that conversation.

That’s it. Then have another. And another. Again and again, and again.

In the near decade of my business, I’ve had to end three major business relationships for business to move forward.

The one thing I wasn’t prepared for when I signed up to be an entrepreneur was having difficult conversations. And having them in a productive manner that moved business forward while keeping the other person okay?

There was no course for that.

For each of these endings, the lessons learned have been invaluable.

The first relationship I ended via email. Not a hope to salvage the relationship as all bridges were quickly burned. The lesson: A conversation is the minimum respect we should show our colleagues.

The second, I removed my empathy; hardened my heart and my tone. While it was done face-to-face (Zoom-to-Zoom) and valid points were evenly stated, the compassion required was non-existent. The lesson this time was that a band-aid rip will more likely destroy relationship than transform it without causing harm.

The third time was another opportunity to practise this very hard thing. There were three steps to prepare for the call that were key to turning this next ending into a transformation.

Reflect in gratitude

All relationships – including your business ones – serve a purpose. Whether a positive or negative experience, this relationship brought something to your business that needed attention.

Questions to help you reflect:

Assess your logical needs 

Emotions ran rampant in my first two runs at truly difficult conversations, despite knowing the relationships no longer served our original purpose for coming together. Emotions are important to acknowledge and consider, but they shouldn’t be the sole guide for the future of your business.

Questions to help you assess:

For instance, engaging a business coach for a five-figure business requires a very different skill set than engaging a coach for a six- or seven-figure business. Mindsets, process, habits, personalities – all of these are in a different person. Know the specific person you need.

Express gratitude and a clear ending 

Having emotion and being emotional are two different things. By knowing how the relationship served you, you can more easily tap into your compassion for the person you’re having the difficult conversation with. This allows you to express what you value about the individual, without becoming emotionally tied to their reaction to the ending.

Then focus on providing clarity for a clear ending and get an agreement from them. If done in a caring, compassionate way, all parties will feel heard, seen and valued while able to move forward in the new manner.

Statements to help you start:

Endings aren’t bad or to be feared. Having difficult conversations are truly powerful opportunities. These are what all business owners require for growth.

Respect the relationship to honour it, give it gratitude for what it was and, hopefully, it will be transformed into a new relationship.

These conversations are never are easy. There’s no quick script to having them and doing them well. The only thing we can do is have the conversation. Then have another as they come up.

To learn more about how to start practising your own difficult conversations, read Necessary Endings by Dr. Henry Cloud.

What have you learned from practising hard conversations? Share your insights and questions with Lindsay. Contact inthetrenches@troymedia.com

Lindsay Harle-Kadatz supports overwhelmed leaders in creating more time, money, and relationships through the power of brand strategy. In everything, she infuses humour with process, creativity, and results. Visit her website, or follow her on LinkedIn and Instagram.

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Lindsay Harle-Kadatz

Lindsay Harle-Kadatz is the owner of The Write Harle, helping small businesses turn their content into more time, money, and relationships through the power of original brands and strategy. In everything, she infuses humour with process, creativity, and results.

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