“If you had to pick a date for retirement, what would it be?”

It’s direct. It’s critical to the family business. But it’s also a tough question for a son to ask his father.

“I wanted to talk about it, but none of us knew how to get it started,” said Dave Moffatt, second-generation leader of Watertown manufacturer Moffatt Products.

Thanks to the right approach and setting, though, his son asked the key question, and it opened a door for essential conversation.

“We came up with the date, and it stuck, and it set everyone else free to begin to plan,” Moffatt said. “The reality of the transition sunk in. It was a very powerful experience.”

Tough conversations are easy to avoid but key to helping businesses move forward. That’s why the Prairie Family Business Association is convening a team of experts for a webinar on the topic at 10 a.m. June 7.

“We know family businesses need to have these conversations – often regularly – both for the good of the business and the good of the family,” executive director Stephanie Larscheid said. “Like many of our programs, family businesses leaders are quickly going to discover they are not alone when it comes to struggling with tackling tough topics. And there are many proven strategies that can help you.”

In addition to Moffatt Products sharing its experience, Ginny Curley, founder of Omaha-based consultant Power Your Partnerships, and Tom Iverson, partner in Fargo-based Sagency Talent, will offer expert insight.

“Every person I coach is concerned about their ability to have pivotal, difficult, tough conversations, so this topic is very timely,” Iverson said. “Many of us choose avoidance and allow problems to go on and fester. We take the ‘hope’ strategy and pretend that, somehow, these problems will fix themselves. Instead, we have to move forward with a strategic game plan to address conversations when topics show up, not when they blow up.”

The idea is to hold conversations that build relationships up instead of tearing them down, said Curley, who has spent decades working with organizations on effectiveness and efficiency and who also has a background in counseling.

“It sounds like a no-brainer when we talk about the importance of having a difficult conversation, but it’s one of the things that can stall a relationship or an organization,” she said. “We’re avoiding an opportunity for a relationship to grow, so it gets stalled and sometimes even moves backwards. When we hold back, other decisions are impacted, and ultimately the organization is impacted.”

The webinar will start as simply as discussing how you can begin tough conversations – which often is the hardest part for those involved, Iverson said.

“The No. 1 thing that causes someone not to have the conversation is they don’t know how to introduce the topic,” he said. “But there are phrases to consider, and we’ll share those, and even though it sounds elementary, people will realize it’s not that hard to begin these conversations.”

For the Moffatts, tackling tough topics in a setting such as Prairie Family’s retreat for family businesses proved invaluable.

“It was the first time we had worked with a professional facilitator, and I was able to participate and not lead and take notes,” Moffatt said. “That was refreshing and eye-opening all at once. We discovered all the conversations we weren’t having and all the topics we wanted to talk about.”

The webinar team also will offer suggestions for how to navigate through a conversation and how to look for common ground.

“We want to encourage business leaders to begin having small, more minor conversations consistently. It builds the muscle we need to have big conversations when those arise,” Curley said. “And we want to model good communication for our employees. It’s so important they see us be able to handle those challenging conversations effectively.”

It’s not about developing a script but rather a strategy, Iverson added.

“We’ll discuss how to frame up the issue with positive intent, do it as succinctly as possible and tell your story,” he said.

The Tough Topics webinar is free, and the replay is available for all members to access through their member profile under “Resources”. Click here to learn more.