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7 Ways to Handle Difficult Conversations at Work


Ask any Millennial or Gen Z accountant what their least favorite part of the job is, and many will likely respond, "Having a tough conversation with a client face to face or on the phone." The mere prospect often gives us a tremendous amount of anxiety. In his first article for AccountingWEB, Will Baker, a client services expert at BaCo Tech, offers his tips to make difficult talks easier.

Mar 25th 2021
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I want to begin this by saying I am not a CPA, but I have spent my entire career since college in client services and have learned many things that have helped me as I have moved into the accounting profession.

My first job out of college was in client services for the tech arm of a small marketing company. My job made me solely responsible for the 300 or so clients that utilized this company’s technology. Managing support tickets, training and any updated projects that needed to be passed to our development team all fell into my lap.

It was a job I was not prepared for, and at 22 years old, every one of my clients was my senior. My first week on the job, my boss looked at me and asked, “How old are you?” I said, “22.”

“No you’re not,” he said. And not in a way of shock and awe, but in a matter of fact sort of way. This took me by surprise because I was, in fact, 22, and not lying to him. He then said, “You are 29 until you are actually 29.”

I was pretty offended, to be honest. Did he want me to lie? What did he mean?  He elaborated. “It’s not that I want you to lie, it’s that I want you to act in a way that makes our clients confident in your maturity to handle their issues.”

It was more of a “You are not in college anymore, you have to treat your clients with maturity and level-headedness.” Over my 5 years at that company, and in my career since, I have learned a lot about client services and how to handle difficult conversations at work. Here are a few tips to help you navigate relationships with clients and coworkers alike:

1. Have a Direct Approach

When having a conversation with a client, be direct and clear from the start. If possible, lay out a plan of next steps instead of dancing around the subject or making excuses. People will appreciate an honest and direct approach about what happened and how it can be fixed. Let them ask questions, hear their complaints, and respond calmly and clearly.

2. Be Kind

This is more of a constant state of mind that will pay off when hard news comes. If you’re kind, encouraging, and carry yourself with kindness, your clients will be happier to talk to you. Even in the course of a difficult conversation, kindness will go a long way. People will be more patient and willing to work with you through a tough situation.

3. Share Good News, Too

Even a small piece of good news can go a long way with your clients. If you only reach out directly when you need something or when you have bad news, conversations can become a chore for your client, so share encouraging news too. It will also let your clients know that you are thinking of them and want to serve them well.

4. Phone Calls Are Key

Do not deliver bad news via email. Get on the phone and call them, and prepare a voicemail in advance to briefly explain the issue at hand in case you can’t get in touch. I always like following up with an email as well, encouraging them to listen to what you said and get back on the phone.

5. Initiate the Conversation

You never want to find yourself on the receiving end of a “what’s the status” or “where are we at” message. Proactivity in delivering bad news and having that conversation as soon as possible is important. You don’t want to put your client off. Delivering the news quickly will let your clients know you care about the issue at hand and want to get it solved.

6. Work Through the Solutions Together

In the client services business, your job is to help customers navigate a problem and find a solution. Do not leave them alone to solve the issue. As mentioned in the first point, offer up solutions, but listen to feedback and ideas from your client, too. You never know when someone might have a great idea that leads to a resolution.

7. Be Teachable

You may be on the receiving end of a hard conversation one day. A client may be offering up a complaint or pointing out a mistake made. In these conversations, it can be easy to get defensive and proud, even if you keep these feelings to yourself. I recommend trying to be teachable in these moments. In other words, hear your client out. Ask questions about how you can improve, and own up to mistakes you make. You are never too old or experienced to learn something new, and learning can help you improve your relationships with all your clients.

These are just some of the tips that have helped me in my career. I ended my tenure at that company a few years ago, and when I was telling some of my more active clients this, I called one who I had been working with since the beginning. We had never had any sort of face-to-face interaction; we worked together only on the phone and through email.

He said, “I have to ask, because I have always wondered: How old are you?”

“I’m 27,” I said.

“No way! The way that you handled communication with me, I have always thought you were at least 45.”

I took that as a compliment.