How to Handle a Difficult Business Conversation

If you’re a service-based solopreneur (maybe a freelancer, coach, social media manager or virtual assistant) then at some point you’ll probably have to have a difficult conversation with a client. And if you outsource to a VA, content creator, or other contractor, it’s possible there will be issues to deal with there too. If you’re in business, conflict happens.

Whether it’s your VA who’s continually missing deadlines, a coaching client who doesn’t show up for scheduled Skype sessions, or a freelance client who hasn’t paid your invoice, 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.


How to Handle a Difficult Business Conversation

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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 instinctively feel something bad is going to follow those words, and in most cases, you’re 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 causing the other party to stress out and close down, they should help facilitate a more productive conversation.

Have a solution (or two) to offer

Before you enter into any negotiation – and any 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 freelance client can pay in installments if they’re having cash flow problems. Perhaps your unreliable VA needs an weekly email reminder of exactly what’s on the schedule.

Whatever the issue, 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 by a day or two is causing a problem for you. Your client 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. You’ll also have a starting off point for a negotiation if your team member or client has different ideas from you.

Know where you want to end up

Do you really want to keep working with this client? Is this VA more trouble than she’s worth? Is this person ultimately uncoachable, or at least not ready for coaching right now? Would this client be better on one of your other packages or programs? Get clear before you go in regarding the results you want.

If this is a ‘not now’ situation, leave things open and allow for a re-connection in the future. Always keep things civil and remember that if this client isn’t right for you at this point, he or she may still know people who are. Resolving difficult situations with class and dignity can make you look professional, and actually increase the other person’s regard for you, even if the situation itself doesn’t end well.

Do you find yourself struggling with difficult conversations?

The done-for-you email scripts at CoachGlue.com can help. They’ve created 10 templates to address the most common client conflicts that coaches face. They call this their Tough Talks Kit, and you can easily customize the individual scripts for your unique business. They’ll work for most service providers, in any niche.

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

Tough Talks With Clients

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