Handle Difficult Clients: The Smart Way to Build Trust

Handle Difficult Clients. I know, I know. You probably rolled your eyes just reading that. I did too, honestly. The phrase itself feels like something from a business seminar in a windowless hotel room, right? But here’s the thing: if you work with people, you’re going to run into at least one client who makes you want to throw your phone into the Aegean. (I almost did, once. Santorini, 2019. Long story.)

So, why do clients get difficult?

Sometimes I think it’s the weather. No, really. You ever notice how people get crankier when it’s humid? Or maybe it’s just me. But more often, it’s fear. Or stress. Or, like my old client George, a deep suspicion that everyone is out to get him. (He once asked me if I was “in league with the printer repair guy.” I wish I was making that up.)

I used to try to be perfect. Answer every email within five minutes, say yes to every request, even the ones that made no sense. Once, a client asked me to “make the report more blue.” I still don’t know what that means. I tried anyway. Spoiler: it didn’t help.

Boundaries?

I didn’t have them. My phone was glued to my hand. My friends started calling me “the ghost” because I’d disappear mid-conversation to answer a client’s WhatsApp. It took a spilled frappe on my laptop (true story, still sticky) to realize I needed to change.

Now, I tell clients: “I’m offline after 6pm. If it’s urgent, call me. If it’s not, let’s talk tomorrow.” Most of them are fine with it. The ones who aren’t? Well, I once had a client fire me for not replying at midnight. I slept great that night.

Communication is weird

Sometimes you write the perfect, clear email and they still don’t get it. Sometimes you send a typo-filled, rushed message and they reply, “Thanks, this is exactly what I needed.” Go figure. I started using voice notes. People like hearing a real voice. Or maybe they just like my accent :-)

Case study?

Sure. There was this one client, Maria, who hated everything I did. Every. Single. Thing. I started dreading her emails. One day, I called her and just asked, “What do you actually want?” She laughed. I laughed. We both admitted we were tired. After that, things got easier. She even sent me a Christmas card last year. With a cat on it. I don’t even have a cat.

Staying calm?

I’m not always good at it. Sometimes I go for a walk. Sometimes I eat too many rice gofrettes. Once, I just sat on my balcony and watched the neighbor’s dog chase pigeons for half an hour. It helped.

Some clients will never respect your boundaries. That’s just life. I had one who kept moving the deadline. “Just one more change,” he’d say. Every week. For three months. I finally said, “I can’t do this anymore.” He was shocked. I wasn’t. I felt free.

Turning a difficult client into a loyal one?

Sometimes it happens. Sometimes it doesn’t. I wish I had a magic formula. I don’t. But I do know that being honest, a little vulnerable, and sometimes just a bit stubborn helps.

If you want to read more about how to avoid mistakes in B2B sales, I wrote about it here: Top 3 Mistakes to Avoid in B2B Sales. And if you’re struggling to understand your clients, this might help: The Psychology of Selling: Understanding Buyer Behavior.

Final thoughts?

I don’t have all the answers. Some days I still get it wrong. But I try. And if you’re still reading, you probably do too. Oh, and if you ever spill coffee on your laptop, turn it upside down right away. Trust me.

That’s it. Or maybe it isn’t. I might remember something else tomorrow. For now, I’m going for a walk.

Got your own story or question? Email it to me. We’re all learning as we go - nobody’s got it all figured out.