The Difficult Conversations Every Leader Needs to Master – Part 2

A difficult conversation is any conversation in which there are strong differences of opinion between two people, and which has the potential to become emotional.

This is a two-part article. In Part 1 of this article we explored what makes a difficult conversation difficult. In Part 2 we’ll consider a few practical steps to take to make a difficult conversation more effective and less stressful.

Planning is Your Number One Strategy

Not all things in life can and should be planned. But if you are the one initiating the difficult conversation, it is essential that you thoroughly plan for the conversation. And plan for the things that will likely not go according to your preferred plan.

Planning should take place at EACH of the stages below in order to assure that each stage goes as smoothly as possible. For example, you cannot address follow-up in a discussion (and have a plan to offer) unless you’ve committed time to planning it. The most risky stage is stage 2, since emotions can flare despite your best planning, especially if you rise to the same emotional level as the person you’re talking to. Keeping the conversation on track (as per your plan) is also a challenge, especially if the other person tends to seize control of the conversation, or send it in a different direction.

Understanding Your Objective

The primary objective should be to have a positive learning experience for both of you, a sense of shared objectives in growing past the issue prompting the discussion, and strengthening the relationship between both of you. It should instill a sense of team and belonging. Both of you have to desire to cooperate and move past the issue(s). In order for this to happen, both must be open to the discussion and willing to be humble. There is no winner or loser in the conversation – both should emerge winners and having become better as a result. This speaks to the INTENT both of you have in participating in discussions that aren’t be easy, but will ultimately lead to positives.

Preparing for a Difficult Conversation

Preparing to be an excellent listener. According to Joel Garfinkle in his book Difficult Conversations, the Number One secret for starting a difficult conversation is not what you say, but how you listen. Listening is an intentional act of the listener’s will, a TOTAL focus on the other person in order to not only understand the words, but also the message communicated in his/her body language, emotions, and delivery.

  • To most people in most cultures, listening equals respect.
  • Effective listening means asking clarifying questions.
  • Effective listening requires your own body language to be open.
  • It requires the listener to intentionally suspend his/her judgment of what is being said until after all is said. This is often the most challenging action to execute well.
  • Live out the advice of Stephen Covey: “Seek first to understand, then to be understood.”
  • Taking notes aids your listening.

Preparing the discussion location. The location should be private, distraction and interruption-free. Seating should be collaborative, such as at a small round table, or around the corner of a table, on a couch, or in side chairs at a 90-degree angle. Avoid placing barriers between you, and your seat higher than theirs.

Preparing your emotions and attitudes. Preparation in this area means that you are much less likely to be reactive (and the emotions that can go along with reacting). Because you’ve thought through what could happen, you’ve anticipated the possible negative responses you might encounter and how you want to respond. You may even need to graciously admit you are the one most at fault!

Preparing your discussion points. Think through these discussion points (write them as bullet points):

  • What outcomes you want the conversation to produce.
  • The facts and data to support what is being discussed.
  • Open-ended questions that will prompt a positive dialog and allow both of you to cooperatively explore what happened.
  • Points that you want to make as the opportunity presents itself.
  • Identify the things you might have done that could contribute to the problem.

Practice. Using your discussion points, practice being able to deliver your message with an appropriate tone of voice and body language. Consider practicing in front of a mirror so you can see yourself. Once you’ve practiced by yourself, ask a partner to play the person you with whom you plan on initiating the difficult conversation. Ask your partner to push back so you can practice keeping your emotions in control and your body language open.

Holding the Difficult Conversation

Just before you start. Center yourself by visualizing the process with you successfully conducting the session with a positive outcome.

Open and conduct the discussion. Start off by succinctly stating why the meeting is taking place. You may want to set the tone for the discussion by stating you may be to blame in part for the situation and your intention to have an open discussion about it. Then begin by asking open-ended questions and listening.

“Sue, I wanted to meet with you to discuss what happened yesterday between you and Ed. I’ve had several people in the department express their discomfort with the tension that now exists. I may be partly to blame for the situation, so I’d like us to have an open discussion to learn more. Can you please tell me in your own words what happened?”

Then execute your discussion plan as you had envisioned and practiced it. Keep your emotions in check…by you being calm but concerned, you’ll set the tone for the discussion. If you get sidetracked on a point, that’s okay, but move gently back to your plan when you can. You may need to restate the objective to help the other person keep the conversation moving forward. Keep asking open-ended questions to explore what is not clear, eventually moving into a problem-solving mode with him or her to address the situation.

Build your next-steps plan and help him/her manage to it. As you both problem-solve together, suggest that you both use the time to build an action plan of how to move forward. Both of you should be taking notes. It is his or her plan, not yours – you’re the thinking partner, there to support his or her plan. As you move toward the close of the session, summarize the plan and detail what is to be done, by whom and by when. Set the date for your follow-up meetings. Thank him or her for remaining open and willing to work through the issues, and your belief in him or her as a valued member of the team.

Keep a close observation on his or her performance or behavior and provide reinforcing or corrective feedback as appropriate. Look for positive progress. Keep your scheduled follow-up meetings and help him or her stay on track. Keep a record of his or her progress. And celebrate the victories!

Bottom Line

A mark of an effective leader is how he or she handles the difficult conversations that arise during the course of work. When leaders are adept of creating a calm, collegial conversation, emotions are defused, and relationships are built.

This article was in part excerpted from module 27 of my acclaimed leadership training program, Leading Through People™, which has made a positive difference for more than 10,000 supervisors, managers, and leaders worldwide.

I love working with people and organizations who want to improve their effectiveness! Here are several outstanding resources that can help you and your organization to go to the next level:

About me: I work with some of the world’s top employers by helping them get the most out of their talented people. My company’s extensive leadership development course catalog provides effective skills-building for everyone in the organization, from the new / developing leader to the seasoned C-level executive. My company’s coaching programs produce significant results in compressed periods of time. I also help job seekers, higher ed, and employment services connect people to better jobs faster. My company’s acclaimed career development tools help people navigate the ever-changing landscape of conducting a successful job search. To find out more, please visit us at, email us at, or call us at 215-942-0982.


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