How to Have Difficult Conversations

At my last job, the company designed the month of December to be a catch-up month, where employees would have to participate in various trainings. There would be a series of guest trainers for the month, and one year, I was asked to speak.

I designed a class focused on giftedness and how to find and apply what was uniquely special about you on the job. I ran this class once before and received many participants who made remarkable discoveries about themselves. So, when I was asked to rerun it, I was more than happy too.

As we progressed throughout the program, many staff got to see ways they could offer choices to the people they supported and bring what they enjoyed onto the list of possibilities. One young man had not seen exercise and cooking healthy meals as worthwhile, but during the class, he learned ways to brainstorm better avenues for the people he supported to take it to be worthwhile.

I felt good about my accomplishments during the class until the complaints about management started. One after the other, staff complained about their supervisors being uncaring, incompetent, neglectful, etc. The conversation quickly turned heavy, and I thought these staff members would leave the organization because of their managers. I for sure thought I wouldn’t see them again next December.

But, after some dialogue, it turned out the managers were being blamed because the staff wasn’t getting along with each other. So, I did some more deep diving, asking questions like, “Was the manager a witness to these disagreements?” or “Did you tell your manager that you needed help sorting out a conflict with another coworker?” and the answer was always no.

Finally, I got to the most critical question, “How would the manager know about your challenges if you never spoke up?” And the room went silent.

To move forward, you need to choose a direction to take, referred to as the “hard right.” In this case, it is figuring out the right words to have an uncomfortable conversation with a peer, coworker, or even a family member.

Here are some frameworks to take charge of yourself in these situations.

Formula #1:


I feel_____________________

It would help me if _________________________

Formula #2:

I would like to manage our work better together_____________________________

I wonder if you would be willing to_____________________________________

I think we could then ________________________________

Formula #3:

I need some help

I would like to _______________________________________

I wonder if you would be willing to _______________________________

You can practice these frameworks with a peer, family member, or friend to help have those uncomfortable conversations. If you don’t feel that you are making progress, know there are more “good turns” left to try.

Stay tuned for next week’s blog for more directional guidance!