Strategies for Difficult Conversations – Part VII

Over the holidays, I had a lot of conversations. Some were on the phone, others were on camera and I enjoyed them all. And many of them included interesting communication challenges.

This reminded me of a blog series I did back in 2018, which focused on difficult conversations. I began to think about the challenges I encountered in my personal calls and their relationship to the workplace. There’s a high likelihood that these same challenges impact conversations with co-workers, leaders and customers. To make sure our communication is always as effective as possible, we need to add to our skill set.

So … on that note, I introduce you to The Planner.

Who is The Planner? Why are conversations with them difficult? And what strategies can we use to improve our communication with them?

The Planner is exactly that – someone who plans their conversations in advance. I don’t mean that they jot down a few notes to keep themselves on track. These individuals, for whatever reason – perhaps a tight schedule or a persistent discomfort with conversations – plan exactly how the conversation will go.

In my case, this Planner in my life is someone I know and love. I’ve had phone conversations with them for years and years and, as was the case this past December, video calls as well. For many years, due to work schedules and time zones, these conversations were booked in advance. They always had an awkward element to them. For example, I would start to say something, and The Planner would either immediately interject or simply keep talking, moving the conversation in their chosen direction.

Because of the holiday break, neither time zones nor work were an issue, yet this awkwardness persisted. This became my “lightbulb moment”.  I finally realized they had planned this entire conversation. At the same time, because we were on camera opening our gifts to each other, they were suddenly (and for the first time) thrown off their plan.

My gift to them was a complete surprise. In fact, it left them close to speechless and they lost track of their plan – at least for a few minutes.

When communicating with The Planner at work, consider doing something that will surprise them (in a good way), like bringing them coffee or inviting them out for a walk. In other words, add an element to the conversation that they have not been able to plan in advance. This will create an opening where you will be heard.

As my experience proved, this strategy only works for a short time. After the initial surprise, the planner will revert to their agenda for the conversation.

Another solution is to use a very direct statement that lets them know you need to speak and be heard. For example, you might say, “Darla, there’s something very important I want to share with you today.” Or “Darla, I need to share some valuable information in this conversation.” Make it clear that you have a contribution that must be included in their plan.

A final solution, which works brilliantly with my friend, is to have unscheduled conversations with The Planner in your life. For the past year or so, I’ve been calling my friend at random times. They aren’t always able to answer, but when they do, the conversation goes back and forth, with each of us taking turns listening and speaking.

What about you and your conversations? Is there a difficult conversation you have frequently? It would be great if you’d share it with me. I’ll do some research and share some ideas to improve that communication. Leave your ideas in the comment section below. 

Inspire Conversation! Read more strategies for difficult conversations here.