Why You Should Have that Difficult Conversation

Those conversations you keep avoiding may be the most important ones to have.

Difficult conversations are, well, difficult. We know there are issues to be addressed, things to be said, progress to be made, but it’s going to be tough. We delay, distract, vent to others, doing whatever it takes to avoid the very conversations our company needs to move forward effectively.

It’s human nature to dodge conflict, and many business leaders are guilty of it, to the detriment of their businesses. In fact, one of my co-founders called me out on being a dodger.

And, yes, I’ll admit I’m good at identifying the need for a conversation and requesting the time and space to have it. But when we’re there and about to dive in, I somehow transform into a verbally incontinent comedian. I babble, I spout off irrelevant information as if it’s urgently important and then I roll into as many jokes as possible to postpone getting to the tough part. I do this because difficult conversations are so damn difficult.

Reframing the Conversation

You won’t improve as a leader, nor can your company thrive, when you dodge your weaknesses. With this in mind, I participated in The Art of Leadership workshop for five days last summer. One of the greatest lessons I learned from its presenter Robert Gass, co-founder of the California-based Rockwood Leadership, was how to have a courageous conversation, versus a difficult one.

“Part of why conversations actually become more difficult is because people have put them off for so long,” says Gass, whose background includes training former U.S. President Barack Obama’s team at the White House. Whether it’s training a two-person company or the U.S. government, Gass has seen first-hand how reframing conversations can play a key role in an organization’s success.

“The problem with calling them difficult conversations over and over,” he adds, “is that it can help reinforce the feeling that important conversations are going to be difficult. I’m choosing to call them courageous conversations to help evoke that quality of heart    and spirit that is core to powerful leadership.”

Most of the time, it’s actually the issues between the people that are in the way of them being able to harness their collective wisdom to address their problems, Gass says.

“And so, again and again, the greatest services I bring to teams and organizations is getting them to deal directly, honestly and constructively with each other through courageous conversations.”

How to Have Those Conversations

Before you launch into a courageous conversation, you need to know why you’re doing it and what you hope to achieve. Here are some strategies to

POP to It › Gass advocates the POP model, which involves taking a look at the Purpose, Outcomes and Process for the conversation prior to having it. Focusing on why you’re having the talk, the goals for it and how to best structure the conversation to achieve those goals is essential to creating the foundation for a successful result.

Own Your Sh*t › It’s rare that an issue in your business exists without you playing some part in it. To have a genuine, productive conversation, you need to look at the role you played in creating the problem. Consider the other person’s point of view — how will they see your role in the issue? Sure, maybe there are cases where your leadership hasn’t been a factor, but if you make the time to pause and question yourself, you may discover some unexpected contributions you didn’t realize you were making.

Take a Test Drive › Courageous conversations are a big deal, and just like sales pitches or other important presentations, they benefit from practice. So make your mistakes in the test run, hone your messaging and hear how your thoughts sound out loud. During the leadership workshop, my name was pulled out of the hat and I ended up practicing a courageous conversation with Gass himself in front of 50 other attendees. It was one of the greatest moments of growth in my professional development to date.

Get Over Yourself › A key thing I took away from the workshop is that courageous conversations are not about me (or you). They are about the mission of the company and how the people it serves will benefit from having an issue resolved. They highlight the fact that there is a purpose to our work and our organization that goes far deeper than simply advocating for our own feelings or ego. I matter, and you matter, but not to a degree where purpose should be dismissed or ignored.

Do it in Person › Much to my cowardly dismay, Gass says email is definitely not the right forum for a courageous conversation. Instead, find an appropriate time and space for a distraction-free face-to-face conversation. But don’t allow yourself to procrastinate at this step and keep putting it off.

Be Human › As much as businesspeople may try to pretend otherwise, we’re human beings and we come with human motivations and needs. To be a courageous leader, you need to create safety and trust in your business. Empathy, vulnerability and honesty should be present in your conversations whenever possible. No, this doesn’t mean you should begin rampantly oversharing and flooding the conversation with dramatic shows of emotion. It means listening, attempting to understand the other person’s position and keeping shame and blame out of the equation. We’re humans, not robots, and keeping our humanity in mind is integral to the success of our conversations.

An Authentic Future

Gass has so much more wisdom than I can include here, so do yourself (and your business) a huge favour by going to the Tools & Resources section on stproject.org to learn more about having effective and courageous conversations.

It’s not an easy skill to master — I’m still learning and nowhere near comfortable with it yet — but our teams deserve brave, authentic leaders, and we need to continue striving to become those people.

Erin Skillen is the COO/cofounder of FamilySparks, a mental wellness startup for families and businesses. She is also a VIATEC board member.

This article is from the August/September 2019 issue of Douglas.