Why “Having the Difficult Conversation” is an Essential Leadership Tool

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When you read the title of this article, it’s likely that a specific instance of having a difficult conversation popped into your mind. Just about everyone, at some point in time, has had to have a difficult conversation with someone in their life. It’s part of the human experience—and can be one of the hardest parts. In business, it’s no different. Every leader faces the reality of difficult conversations, and just like in regular life, it’s not something that most leaders look forward to. In fact, they often put those conversations off—especially in family businesses, to the detriment of the family and the business.

In my work with family business owners and executives, I have found that one of the greatest challenges (and biggest blind spots) facing leaders is the art of having difficult conversations.  While some leaders are comfortable facing conflict head-on, most of us avoid them, because we are not prepared to deal with the potential discomfort of the conversation—and the outcome. Nobody likes the strife that comes with a difficult conversation, but as a leader, you simply don’t have the luxury of putting them off. It’s part of the job. But when it’s your family, it can be even harder.

CPP, Inc., an industry leader in research, training, and organizational development tools, conducted a worldwide study looking at workplace conflict and found that, on average, US workers spend approximately 2.8 hours per week dealing with conflict—translating into over 350 billion dollars in paid hours annually. Additionally, 10 percent of workers report that project failures are the direct result of workplace conflict. The number of hours spent on conflict in this report won’t be a surprise to most people in business, and there’s no clear remedy. The real eye-opener here is the direct hit to the bottom line when a project fails due to conflict. That’s why I always ask my clients to ask themselves “What price you are paying by not facing conflict directly and having the tough conversation?” That price goes beyond dollars and cents. It costs human capital. Your standing as a leader and your team’s morale can both be damaged by inaction that leads to poor results. And if you’re not careful, your family relationships can be damaged in the process.

The art of having difficult conversations is something that every family business leader will need to excel at, if not master, to become truly effective. Here are some strategies to start you on your way.

It’s a 2-Step Process

There are really only two steps to this process—thinking and taking action. Optimizing your thought process and learning the skills to make you confident in acting are the skills every leader must develop.

Step 1: Preparing for the difficult conversation  

For most, one of the outcome goals of the difficult conversation is minimizing the hurt, anger, and guilt while ensuring that the message comes across. It’s a good goal to have, but this implies an optimal outcome for every situation, which is unrealistic. Everyone’s perception is their reality, and you can’t control the perceptions of others—or even your own. That’s why it’s best to prepare for a difficult conversation by having a difficult conversation with yourself. Ask yourself if you have a full, clear grip on the situation. Are you sure you are right, and the other person is wrong? What are you missing? What have you not considered? It is critical to be fully objective. To do so requires you to change your judging thought process to a learning process. Go from certainty to curiosity. And always consider the feelings of others. Once you have a full grasp of the objective facts and a clear eye for everyone involved, you can take action.

Step 2: Four key behaviors needed to take effective action

We can never change another person’s behavior—however, we can push them to change in response to our behavior. Going into a difficult conversation prepared will give you the confidence to achieve this. Following these five behaviors prior to your meeting will help you foster a calmer presence and positive tone for the interaction—and allow you to achieve your goals.

  1. Be intentional. Know what your goal is before the meeting begins—and never lose sight of it.
  2. Clarify the issues. Just the facts ma’am. Do not attack the person, present them with objective data or specific behaviors that you want them to change. Do it calmly and assuredly.
  3. Don’t just listen—hear. Active, non-defensive listening is paramount. It can be a hard skill to master but staying aware of how you are listening will help.
  4. Acknowledge the other person’s perspective. Even if you don’t agree with it. Practice empathy and give the other person time to heal and think after the meeting before making any final decision.
  5. Don’t avoid the person outside of work. If your work spills too far over into your family, both will suffer. Keep the business, business and the family, family. Both will be better off for it.

Mastering the art of difficult conversation doesn’t come overnight. It’s a mind exercise that you must repeat every time you face a difficult conversation. Over time, you’ll stop fearing them, and your family and business will be healthier as a result.

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