Expecting a Difficult Conversation? It Will Be Easier If You Do This.

HR insights and tips with Jeff Havens

Hello, and welcome to another installment of HR Intervention! I’m Jeff Havens, and I realize that other people are occasionally annoying.

Sometimes people think they deserve a raise when no one else agrees with them, while others seem to be surprised when you tell them that shouting profanities at customers or showing up several hours late actually is grounds for termination.

By virtue of choosing to work with others, you have guaranteed that you will periodically endure more than your fair share of challenging, difficult, and grueling conversations.

You’re probably never going to emerge from a difficult conversation saying, “Golly, that was awesome – can’t wait to do another!”

But there are ways to make them less painful:

Frame The Conversation As An Effort to Help

When you’re going to tell someone they’re doing something wrong, you’ve got two options. You can frame the conversation as a reprimand for failing to meet expectations, or as an opportunity to improve whatever the deficiency is.

One of those approaches has the potential to turn into a constructive back-and-forth, while the other will almost certainly devolve into an endless game of attack and defend.

Don’t Apologize For Anyone Else’s Mistakes

Most of us have a tendency to apologize for bringing up a delicate or difficult topic. However, that initial apology often makes the issue at hand seem less important than it really is.

As best as possible, avoid saying you’re sorry for discussing something you felt compelled to bring up.

Do It Sooner Rather Than Later

I fly a decent amount, and every so often I look out the window of the plane and think, “If I had a parachute on me right now, I’d totally jump.”

But I’ve never gone skydiving because the idea of preparing for it has always stopped me – there’s too much time during all those safety lessons for me to realize how dumb it is to willingly jump out of a perfectly functional airplane.

The point I’m trying to make (other than highlighting my own cowardice) is that the less time you spend thinking about a conversation you know you have to have, the easier that conversation will be.

That’s not to say it’s going to be a cakewalk, but stewing over it for hours or days on end is only going to make things even more difficult.

Find Someone Nice To Talk To Immediately Afterwards

Difficult conversations can be enormously draining. However, since it’s probably against company policy to skip out at 11 am to drown your frustrations at a nearby bar, consider stopping in to a colleague’s office to unload a little.

Not only can talking it out be helpful psychologically, but the person you choose to talk to might also have a few good suggestions about how to make your next difficult conversation easier than this one was.

Difficult conversations will always be difficult, but they don’t have to be crippling.

Now if you’ll excuse me, I have to go tell someone they smell bad. Not quite sure how they don’t know it themselves, but I’m thinking that maybe walking into their office wearing a gas mask might at least give them a hint about why I’m there.

If the odor conversation vexes you, we have training for that! Check out this video preview and request a demo of The BizLibrary Collection to see how we can help you train your workforce on a variety of topics!

Jeff Havens is a speaker, author, and professional development expert who tackles leadership, generational, and professional development issues with an exceptional blend of content and entertainment. He is a contributing writer to Fast Company, Entrepreneur, BusinessWeek, The Wall Street Journal; and has been featured on CNBC and Fox Business. For more information, or to bring Jeff to your next meeting, call 309-808-0884, email, or visit

Speaker, Author and Professional Development Expert