The Business of Difficult Conversations

Relationships have ups and downs. Let’s see a show of hands for those who have faced challenges in partnerships, with family, customers, clients, marriages, and friendships? As a business owner, my question for you is what did you bring to that challenge?

I am an expert in relationships. I’ve worked in my family’s business. My Dad had a construction business when I was growing up. I’ve partnered with my husband and a couple of friends to build a business that we then sold to a national company. As a therapist, I built an outpatient therapy caseload. I have a coaching practice. I consult with clients who operate partnerships and businesses. I’ve been married 33 years and have two amazing daughters. I know relationships.

As a business owner, how did you move forward when a relationship faced a crossroad? How did you contribute to it? How was it resolved? In hindsight, were there things you know now, that if you knew then, would have impacted your behavior? That is what I’d like to help you avoid- the REGRET.

3 Tips that can positively impact difficult conversations in business relationships

  1. Identify the underlying assumptions-ask yourself whether you want to win or be effective.
  2. Take a minute to reflect on your nonverbal communication- are you frowning, hands fisted, clenching your jaw, looking at your phone? Relax. Give your attention to the person across from you.
  3. Listen. Notice. Resistance can be the result of lack of clarity. Ask questions for understanding and information about the other’s point of view.

In closely held companies, the founders bring their experiences, and beliefs. They work to merge the two. Each represents the opportunity to build resilience in the relationship. Each can call the other to their best, or their worst. How will you choose to show up in those difficult conversations?

As always, if you are challenged by this process and want the support of a coach while you work, contact me. (804) 372-7575 or

Wendy Dickinson

About the Author

Wendy Dickinson is the founder of Ascend Coaching Solutions LLC, a coaching firm that specializes in working with business owners and executives who plan to expand their leadership capacity as their business grows.

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