How to Manage a Difficult Business Conversation

woman at white desk looking at phone

Some things just can’t be avoided. Taxes. School fundraisers. Cellulite.

And if you’re in business, conflict.

Whether it’s your VA who is continually missing deadlines or a JV partner who failed to pay your commissions, as a small business owner, you’ll have to deal with it sooner or later. Learning how to handle difficult conversations is a critical skill that will serve you well.

The trouble is, handling conflicts with grace doesn’t come naturally. We’re human. We react—sometimes badly—when we should be proactive instead. We take things personally when they’re not. We sometimes lash out first and apologize later.

With a little planning and consideration, though, you’ll have a much better outcome, regardless of the nature of the conflict.

Set the Stage

Nothing stresses us out quite like the words, “We need to talk.” You just know something bad is going to follow those words, and in most cases, you’ll be right.

Rather than starting a difficult conversation off with words that instantly put people on the defensive, begin on a positive note.

  • “Can you help me figure out what happened with_________?”
  • “Do you have a few minutes? I want to run some ideas by you.”
  • “I think we have different ideas about ________. Can you help me clarify some deadlines?”

All of these conversation starters invite openness and idea sharing, and rather than being stressed and closed down, the other person will be more open to a productive conversation.

Offer a Solution (or Two)

Before you enter into any negotiation—and a business conflict is just that—it’s a good idea to know exactly what you’re willing to offer. In the case of a difficult conversation, what you’re offering is a very likely some kind of compromise. Maybe your JV partner can make payments. Perhaps your wayward VA needs an additional reminder of upcoming tasks.

Whatever the trouble, be sure you have at least one potential solution in mind before you initiate the conversation. Remember, this talk may come as a surprise to the other person. Your VA may not realize that missing deadlines is causing a problem for you. Your JV partner might have not realized he or she missed the payment.

By providing at least one potential solution, you’ll avoid the awkward back-and-forth, go-nowhere conversation that ends in frustration. (“I don’t know, what do you think we should do?”)

Do you find yourself struggling with difficult conversations?

The done-for-you email scripts at can help. They’ve created 10 templates to address the most common client conflicts that coaches face. You can easily customize them for your unique business, then share them with your VA so she can send them as needed.

You get a stress-free way to deal with the unpleasant issues that sometimes arise in business, and your clients receive thoughtful, caring responses.

Tough Talks Kit: 10 Done-for-You Letters to Help You Manage Difficult Client Situations with Ease

Leave a Comment

Your email address will not be published.