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How to Have Tough Conversations with Clients


If having conversations with your clients about pricing or billing is a challenge, committing to having these discussions might be the first step. Here, Jim Boomer, CEO of Boomer Consulting, provides a few tips for sharpening your soft skills to create an intentional dialog with clients who need reassurance or help facing their financial fears.

Apr 11th 2022
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Being a trusted advisor to your clients requires having in-depth conversations. You may have no problem talking to your clients about how changes in the tax code apply to their business or how to record a transaction following general accounting principles, but what about the tough conversations?

Does talking about fees, past-due invoices or issues with how a client is running their business make you uncomfortable? Do you avoid it altogether? If so, you (and your clients) could benefit from these tips for having tough financial conversations with clients.

Commit to having crucial conversations

People tend to have a lot of “head trash” – negative thoughts, feelings and emotions and the assumptions you make about them – when it comes to talking to clients about pricing, billing, collections and other tricky topics.

Maybe you think they’ll be upset about a price increase and imagine the pushback you’ll get. Or perhaps you worry that if you pressure your client to pay their outstanding invoice, they’ll take their business elsewhere, so you avoid calling to follow up. The problem with head trash is that your negative beliefs become behaviors that prevent the types of results you want.

Rather than letting your head trash get in the way, commit to having those difficult conversations. Set expectations upfront about pricing, timely billing and collections, and tell clients what they need to hear rather than what you think they want to hear.

Minor issues, when addressed promptly in a thoughtful and compassionate way, are easy to fix. Left ignored, they tend to expand into major problems.

Set out to create a dialog

When approaching a topic you know will be particularly delicate, aim to create a dialog with your client.

In order for a dialog to take place, both parties need to feel safe enough to exchange facts, ideas and thoughts that will lead to an outcome both parties feel good about. The tricky part is recognizing right away when the conversation starts to head in a negative direction. This can be tough when you’re also thinking about what to say next.

Whether you have a conversation over the phone, over video or in person, look out for verbal and/or physical clues that communication is breaking down. For example, people might resort to sarcasm, change the subject or exit the conversation altogether, cut you off, dismiss you or your ideas or attack the messenger.

Make it safe

When the conversation goes in a negative direction, how can you pull it back to safety? Once you realize what is going on, step away from the challenging topic temporarily. You can then work on building safety by getting back to the facts and eventually returning to a dialog.

If you are at fault, apologize. Your apology must be genuine. People can see through an insincere apology quickly, and it makes people feel disrespected.

If your intentions have been misunderstood, try contrasting. Contrasting is a skill that helps you clarify your intentions, so the other person feels safe. You start by saying what you are NOT talking about, then follow that with what you ARE talking about.

Control your emotions

Controlling emotions can be difficult during a tough conversation, so being able to take a step back and analyze the root cause of your emotions can be a very powerful skill.

When you give advice that the other person doesn’t want to hear, they may try to defend themselves by attacking your statement. Don’t allow yourself to become defensive – it will only escalate the tension.

Instead, try finding a mutual purpose. Creating a mutual purpose requires some work. What you see on the surface is a person’s behavior or strategy for getting what they want. Their purpose is what lies beneath, so you need to ask “why” questions to respectfully drive out any hidden or buried agendas. If you can clarify each person’s goal, hopefully you can find a solution that will satisfy both goals.

Difficult conversations are bound to come up from time to time, but it does get easier with practice. Simply by facing up to some difficult topics, you’ve taken a positive step toward building trust, and trust is the foundation of a positive client relationship.

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