How to Have a Difficult Conversation

One of the key differentiators between the exceptional business owners and the average business owner is the ability to navigate difficult conversations successfully. As a business and executive coach I see this frequently.

Whether it is a conversation with a customer, a vendor, a partner, or an employee, from time to time we all find ourselves in the middle of a difficult conversation. This becomes even more acute when we have family members working in our businesses. We must know how to have a difficult conversation when the time arises.

One of my favorite tools for coaching business owners and the executive on this subject is the book Crucial Conversations by Patterson, Grenny, McMillan, and Switzler. Today, I hope to share some insights and tips from my experience and from this excellent resource to help you as you engage these situations.

What Makes a Conversation Difficult?

For now let’s identify what makes a conversation difficult and what immediate steps we can take. The authors of Crucial Conversations suggest that there are three factors that make the conversation difficult.

First, opinions vary. For example, you and your team have to solve a sensitive customer service problem but everyone has a different perspective on what needs to happen. You need them to be a part of the solution but everyone sees the issue differently.

Second, the stakes are high. You know that if this customer service problem is not handled correctly you will lose a very large account that will effect your bottomline.

Finally, emotions run strong. Some of your team members have been at odds with one another and you’re at the end of your rope with them. Worse yet, this valuable customer has expressed in no uncertain terms their disappointment with your service.

Typically when opinions vary, stakes are high, and emotions run strong you are headed for a train wreck. So what do you do? How can you guide the conversation to make sure this has a good resolution?

Look at Yourself

The first thing you need to do is to step back for a minute and ask yourself 3 questions:

  1. What is it that is creating anxiety for me in this situation? Identify the exact source within yourself and let that go for a few moments.
  2. What is it that I want – what do I want for me, for my customer, and for my team?
  3. What action can I take that will acknowledge what’s going on right now and move us toward a positive outcome for all concerned?

This may not come easy at first but practice these 3 questions until you master them. A key aspect of being a successful businesses owner is knowing yourself and your mindset.

Learn to Observe

The next step in handling a difficult conversation is to learn to observe.

Once you gain some emotional detachment by stepping back and looking at yourself, then look at the situation. Look for both content and conditions. By content I mean look at what is actually being said as well as what is NOT being said. By conditions I mean to look and see if everyone feels “safe” to talk about the real issues. If there is not safety there will not be dialogue. Do you see any “flight or fight” taking place?

When “flight” is taking place, you might observe withdrawal, avoidance, or masking behavior. When “fight” is taking place you might observe attacking, labeling, or controlling behaviors.

Most important, be sure you are watching for these types of behavior in yourself. The better able you are to observe this in yourself, the better able you will be to observe this in others.

Keep the Dialogue Going

The goal is to keep all parties engaged in constructive dialogue. But dialogue is NOT debate! Dialogue is characterized by listening and sharing honest perspectives, not defending. The moment we start defending ourselves or our positions, we have moved away from dialogue. In dialogue we must suspend judgement and learn to listen objectively and openly.

Bottomline, when a conversation turns “crucial” the tendency is to become defensive which typically leads to flight or fight. The dialogue is over.

As a business and executive coach, I encourage my clients to first look at themselves, and then to learn to observe. Watch for safety problems and work to maintain dialogue.

Glenn Smith is a sought-after Executive Coach with over two decades of experience. Recognized for his strategic insights and leadership training, Glenn has been a guiding force for more than a hundred successful small to mid-sized businesses. Merging data-driven strategies with profound insights into human behavior, he aids business owners and executives in realizing their fullest potential. A respected thought leader, Glenn has contributed to numerous business publications and is a popular keynote speaker. Outside his professional realm, Glenn cherishes family time and outdoor activities. He is a pilot with over 30 years of flight experience. He is also a professionally trained gunsmith and a firearms instructor. His dedication to fostering leadership and driving transformative change marks him as a premier figure in executive coaching.


How to Have a Difficult Conversation

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