Coram Deo ~

Looking at contemporary culture from a Christian worldview

The Most Difficult Conversation I Ever Had at Work


As a leader, I had to have many difficult conversations in my career. But as I reflect back, there was one conversation that took place several years ago that stood out above the rest as the most difficult.

In the organization I worked at, we would regularly have conversations about analysts who had the potential and interest to move into a leadership position. If everyone agreed, these analysts would be placed on a “promotability list”. This list would have multiple levels.  Being placed in the top category indicated that they were ready to take on a leadership position.
One of my team members was in that top category when our leadership team had their regular conversation about our area’s candidates. At that time, there was very little movement of analysts into leadership. As a result, there was new criteria applied to those on the list. As a result, my team member was not approved to stay on the list. They were not going to be moved back a level on the list, but taken off the list completely, which was very unusual. As their leader, I would have to communicate this news to them. But I was going to be out of the office on a previously scheduled vacation before our meeting. Needless to say, I thought about our meeting a lot during my vacation.Communicating this news was going to shatter a career dream for this individual. They were pretty much being told that they now didn’t have what it was going to take to get into leadership. But when I met with my team member, they could not have been more gracious. They received the information in a professional manner.
Here are 5 tips on handling crucial or difficult conversations. They helped me to prepare for and execute my most difficult conversation at work.

  1. If possible, you never want to go into a difficult conversation without being sure of what you are going to say. I would outline the major points that I wanted to be sure and cover and have that in front of me in the meeting.
  2. Before a difficult meeting I would always pray for the meeting, the individual involved and myself. I would ask for just the right words to allow me to deliver the message, show respect for the individual(s) involved and honor the Lord.
  3. Stay Calm. You never know how someone is going to react to what you are sharing with them. In the example I gave above, the individual received the information in a professional manner, but anger, shouting or tears could have been the response. You have to be confident and deliver your message as planned.
  4. Stay on Script. It is important that you stick to your message points. In addition to an emotional reaction, my team member could have tried to bargain with me. But the decision had been made to remove them from the promotability list. I did not have the authority to deviate from message.
  5. Show concern for the individual. As in any conversation, positive or constructive, a servant leader needs to show concern for the individual involved. In this case, the individual received some very difficult and unexpected news. Their dream of achieving a leadership position was most likely over. As a leader you need to assure them of their value to you, their team and the organization at this time more than ever.

If you have been in leadership for any length of time, chances are you have already experienced some difficult conversations; it goes with the territory. I’ve shared 5 tips on preparing and executing these conversations. What would you add to my list?

Author: Bill Pence

I’m Bill Pence – married to my best friend Tammy, a graduate of Covenant Seminary, St. Louis Cardinals fan, formerly a manager at a Fortune 50 organization, and in leadership at my local church. I am a life-long learner and have a passion to help people develop, and to use their strengths to their fullest potential. I am an INTJ on Myers-Briggs, 3 on the Enneagram, my top five Strengthsfinder themes are: Belief, Responsibility, Learner, Harmony, and Achiever, and my two StandOut strength roles are Creator and Equalizer. My favorite book is the Bible, with Romans my favorite book of the Bible, and Colossians 3:23 and 2 Corinthians 5:21 being my favorite verses. Some of my other favorite books are The Holiness of God and Chosen by God by R.C. Sproul, and Don’t Waste Your Life by John Piper. I enjoy music in a variety of genres, including modern hymns, Christian hip-hop and classic rock. My book Called to Lead: Living and Leading for Jesus in the Workplace and Tammy’s book Study, Savor and Share Scripture: Becoming What We Behold are available in paperback and Kindle editions on Amazon.

5 thoughts on “The Most Difficult Conversation I Ever Had at Work

  1. I had to have a performance counseling conversation with a direct report recently, and due to the COVID-19 restrictions, that conversation was OVER THE PHONE. So I had none of the visual cues and nonverbals most people can rely on to gauge how the message is being received. Instead, I visualized having the person in front of me and having this conversation, and we also talked about options for moving forward, which seemed to “lift” the discussion. So to add to your list, I would say try to visualize how the person might react–facial expressions, body language, etc.

  2. The other factor is you no doubt had a good relationship with this person which made the conversation smoother. So whether you are in a position of leadership or just informal influence, it’s always a good idea to build good relationships with people because you never know when you may need to have an emotionally charged conversation with someone you care about.

  3. Good solid advice, Bill!

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