Tough talk: Getting comfortable with uncomfortable conversations

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By Colleen Killen-Roberts

Let’s face it, difficult discussions are simply not fun. Yet business leaders can’t shy away from tense topics, especially operations professionals who are charged with implementing structure and monitoring performance. It’s important to have difficult conversations in a way that’s authentic, direct and productive. And though this may not feel natural, the good news is that you’re building a new muscle — one that gets stronger each time you use it.

A few things to note:

Don’t procrastinate. Even though avoidance might be easier in the short-term, from my experience, it costs more energy in the long run. It’s also not good for the organization. If you don’t call people on their bad behavior, whether it’s missing meetings, shoddy deliverables or not walking their talk, they’ll assume their behavior is acceptable. Once you clear the air, both you and your team member will feel better.

Check your state. Before I engage in a difficult conversation, I check in with myself. Am I coming from a good place? For example, I’m usually pretty upbeat, but suppose I had an argument with my husband before coming to work —  then I hit the pause button. Otherwise I’m not bringing the best version of myself to the conversation, and the likelihood of a successful outcome is diminished.

Have a plan.  What are the three main points you intend to discuss? Practicing what you plan to say can be helpful. Don’t memorize a speech verbatim, but go over it so you’re polished enough to say it in different iterations. Being prepared helps you stay on topic.

Stick to the facts, not your interpretation of them. What are the givens of the situation? Try not to deviate.

Visualize an ideal outcome. Throughout my career, I’ve often had to terminate people, which is never pleasant. But if your approach is to create a win-win scenario —  to concentrate on problem-solving rather than accusing — it makes things a lot easier. Often underperforming employees know the situation isn’t working out for them, but they find it easier to stay than to leave. You can give them permission to leave, by saying something like, “This isn’t working for you, and it’s not working for the organization. Let’s find a way to create a transition so you can move into something that fits you better.” This is a totally different mindset than going into the conversation thinking, “This person is a bad seed, and I can’t wait to get rid of them.”

It’s okay to be direct. Too much candy coating confuses the situation. This is something I learned the hard way. In my first years as a manager, when I had to tell someone something they didn’t want to hear, I would tap dance around issue. I was trying to follow the “sandwich” school of thought where you give good news, then bad news and then more good news. The only problem, I would provide good news, no bad news and then more good news. The other person’s reaction was complete confusion. “You’re telling me I’m good over here and awesome over there, why are we even talking?” (Yikes!)

The more direct you can be, the more refreshing it is. Directness does not equal rudeness. For example, “It pains me to tell you this, but you’re dropping the ball here. Help me understand why.”

Be respectful. Always. If you approach an uncomfortable conversation from a point of collegiality, kindness and respect, it makes all the difference in the world.

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Colleen Killen-Roberts
Divisional Vice President of Entrepreneurship
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“Entrepreneurs need a bridge between their dreams and reality,” says Colleen Killen-Roberts, Divisional Vice President of Entrepreneurship at the Edward Lowe Foundation. “And that’s where operational expertise comes in. Operations is about creating the necessary infrastructure to take the entrepreneur’s ideas and make them happen.” In this series of articles, Killen-Roberts shares insights gleaned from more than 25 years of operational and fiscal management experience at second-stage companies.