Leadership Simplified: Doug Van Dyke


How to Deliver Difficult Conversations

Volume: December 2011

By Doug Van Dyke, Leadership Simplified, www.leadershipsimplified.com


These are interesting days, and within them leaders sometimes have to deliver tough messages. This time of year it is not uncommon for performance reviews to be taking place, or budget discussions, or reductions in force, or realignment of resources, or strategic planning. All of these actions and processes can contain difficult, yet necessary conversations. Regardless of the topic, many leaders are apprehensive to drive a challenging conversation within an appropriate timeframe. The difficulty lies not in the leader’s lack of ability to successfully hold a difficult conversation, but rather because they are not properly prepared for the discussion. Once prepared, most leaders can deliver tough love in a most effective way.


So what are the steps involved in holding a difficult conversation? Keep reading my friends, the five steps leading to your “tough talk” success are listed below.

Step 1: Analyze the Situation. As you ponder the circumstances of the conversation, ask yourself the following five questions:

  1. What potential positives could result from the conversation?
  2. What are the pitfalls and drawbacks?
  3. What are the ramifications of delaying or avoiding the conversation?
  4. What are the two core deliverables I want to result from the conversation?
  5. What topics do I want to avoid during the discussion?


Step 2: Craft a Strategy. The answers to the questions contained in Step 1 will help you craft the best strategy possible. Here are five additional items to consider while crafting your strategy:

  1. Where is the best place to hold the conversation (i.e., your office, a conference room, etc.)?
  2. How do you want to physically position yourself (i.e., behind a desk, on the same side of a conference table, on the opposite side of a conference table, etc.)?
  3. What will be the best opening to the conversation? In this regard, think strategically about the qualities of the team or audience with whom you will be meeting.
  4. How will you handle potential objections?
  5. What tone of voice and body language should you use? More about these in Step 4.


Step 3: Practice and Prepare. When I coach leaders on presentation skills, the number one rule I implore is to practice, practice, practice! Well, if you are entering into a crucial conversation, it is worth your time to practice the core content of the conversation at least five times. Note that practice does not make you sound scripted. Rather, the purpose of practice is to make you so comfortable with the topic at hand that you will be able to concentrate on more important matters, such as the reaction and comments of the team member you are addressing. The last thing you want during a difficult situation is to be struggling to articulate your position on a matter. By practicing you will obliterate your potential struggles and better lock-in on the nuances of the conversation.


Step 4: Deliver with confidence. This is where you seek to have a perfect marriage of the words you have chosen, the tone of your voice and your body language. In particular, your tone and body language play a critical role. Seek to have a firm tone of voice. If your voice is harsh it may spur a confrontation, while if it is too nurturing you may come across as wimpy. Also, make certain that you maintain solid eye contact while leading the conversation. In addition, your facial expressions should mirror your message. Lastly, do not cross your arms. This may create a combative atmosphere. Keep your posture open, and let your eyes and tone send the message that you are confident. 


Step 5: Follow Up, Reinforce, and Chart Progress. Most leaders make a huge mistake after they successfully hold a difficult conversation: They heave a sigh of relief and move on to the next item on their To Do List, thus totally forgetting about the conversation that just took place. Big mistake. What smart leaders do is tickle their calendars with specific milestone dates when they will casually check in with the team member or group. During the check-in meetings the leader can effectively determine if the conversation was taken to heart. Also, is the team member or group engaging in the specific actions or behaviors that were called for during the initial meeting? And most importantly, positive actions can be reinforced and anything that was misunderstood or not acted upon can be corrected. Often times, leaders do not execute this crucial step because it sometimes leads to yet another difficult conversation. Let your follow ups keep things moving forward and thus mitigate the need for future tough talks. Remember: Communication and consistency is king.


Bottom Line: Leaders sometimes have to deliver difficult messages or confront a tough audience. No matter what mix of challenges you face, effectively drive difficult conversations by embracing a 5-Step formula. If executed correctly you will find yourself delivering tough love in a more confident and expeditious manner, while experiencing better results on the back end.


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Please do so, as long as you do not alter the content or embedded links. Also, please include the following information: Doug Van Dyke is a leadership and collaboration consultant, executive coach, and strategic planner. Doug’s book, Leadership Simplified, as well as audios and videos are available at www.leadershipsimplified.com. To learn more about coaching and training services, contact Doug today at .(JavaScript must be enabled to view this email address). 

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