All Articles Leadership Management Mastering difficult conversations, part 2: Difficult conversations with good people

Mastering difficult conversations, part 2: Difficult conversations with good people

5 min read


In part 1, we discussed having conversations with difficult people, where the main issue is never expecting such people to not be difficult and finding a way to stay centered and unprovoked by them.

In part 2, the issue becomes how to master difficult conversations with good people.

Characteristics of good people

  • Low maintenance, i.e., easy to please, difficult to upset
  • Take life but not themselves too seriously
  • Passionate and compassionate
  • Work well on their own and as team player
  • Don’t buy into negativity
  • Someone you’d want your sister, brother or child to marry

What are some of the most common kinds of difficult conversations?

  • Layoffs
  • Transfers
  • Pay cuts
  • Negative reviews of work product
  • Delaying or reneging on expected promotion, pay raise or bonus
  • Any disappointing news that will negatively impact, disappoint and/or upset these people

What do difficult conversations with good people have in common?

  • You have had multiple past experiences of people having become overly upset with disappointing news.
  • You have been on the receiving end of news that disappointed and/or upset you.
  • Underneath the upset of others or yourself was a significant amount of hurt and/or anger.
  • Knowing what it’s like to feel upset like that, with hurt and/or anger beneath, you don’t want to cause someone else to feel that way.
  • Other people feeling and looking upset makes you feel guilty, as if you have hurt them.
  • You can’t stand the feeling of having hurt or upset someone else.

In part 1 of this series, you had a legitimate reason to be concerned that disappointing or upsetting a difficult person would provoke them, incurring their wrath or some other “over the top” reaction, or that their whining would feel like nails on a chalkboard.

In this post, the issue is that you are projecting onto good people how others (such as the difficult people in part 1) or how you would feel to receive negative news. Upon doing this and, especially, knowing how you would feel, you assume that is how they will feel. The more upset you would feel with receiving bad news, the more you assume they will feel the same way. The more negatively you would react to such news, the more you believe they will do the same.

So here is the key point to remember: It’s not about you.

Tips for difficult conversations with good people

After you accept that it really isn’t about you, doing the following will make it less difficult to have these conversations with good people. They may never make them pleasant, but they will help you make them less lousy.

  1. Know why such upsetting news was unavoidable: Just because they feel disappointed or upset doesn’t mean you are disappointing or upsetting them. It is the unavoidable news because of some circumstance in your business that has caused this conversation to be necessary.
  2. Know you have explored all possible alternatives before deciding on actions that would be upsetting to people: The more you feel you have thought through other solutions, the less you will feel that this was an impulsive action on your part.
  3. Realize that the upsetting news is less upsetting if the people affected by it are given options: Most good people understand that sometimes life gives you good news and sometimes it gives you bad news. What’s usually most immediately on their mind is what will happen to them next. The more you explore options for them inside and outside your company, the better they will handle these conversations.
  4. The more you or someone in your company has thought of options for the people who are adversely affected and possible calls you can make on their behalf, the less guilt you will feel: Sit down with this person and brainstorm with them about their actual specific value (i.e. what they get done) to your company and to any company. Tell them their most valued traits such as being diligent, getting work done on time and within budget, having initiative but also able to work cooperatively in a team; all this, of course, you will put in a letter of reference will cause them to feel more hopeful and also lessen your guilt.
  5. Realize that avoiding the telling of upsetting news makes matters worse. The longer you avoid the unavoidable and the more you beat around the bush, the more needless pain and suffering you will cause the other person and yourself.

Finally, it’s good to keep in mind that these situations are among the best opportunities to demonstrate leadership. There are few things as upsetting as having to tell good people something disappointing or upsetting. But when you do it in a way that is candid and helpful, you give them the chance to feel hopeful instead of downhearted. And that will increase the esteem and respect for you from others (including the good people you have had to tell something upsetting to) and yourself.

Related Reading and Resources

Dr. Mark Goulston is a co-founder of Heartfelt Leadership, whose mission is daring to care. He is a No. 1 international best-selling author of six books and he is a former FBI and police hostage negotiator trainer.