Difficult Clients Are Very Much Like Toddlers.

Teresa Lagerman
The Startup
Published in
5 min readMay 30, 2019

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Photo by Phil Goodwin on Unsplash

When you start freelancing, you’re giddy with the possibilities in front of you. Doing the work you love, setting your own schedule, saying goodbye to the rats on the subway. But you’re also quickly overwhelmed by the daunting prospect of, well, finding work, and the instability of good months and slower months. And just when you’re starting to get the hang of it, that dreaded monster rears its head under the bed — the difficult client.

Everybody has a different picture of what makes a client difficult. Figuring out the core traits of your own pain-in-the-neck type really helps you identify them and gently (yet swiftly) steer them in a different direction before they become an issue. For me, it’s three things:

  1. Character compatibility. If I’m going to be working closely with someone for a few months, I need to feel confident it’s going to be a positive experience for both of us. The type of work I do is very collaborative and requires a lot of input and interaction, so having good chemistry just makes things go naturally smoothly. This is not necessarily about personality, but rather about certain character traits that will impact your working relationship. I ask myself, how would this person handle creative disagreements? Are they able to articulate their vision, what they like and don’t? Are they driven more by passion or by ego? If those primary character qualities aren’t aligned, the project is likely doomed.
  2. Relationship outlook. Some people value you as a partner whose expertise can help them grow, and some see you purely as a contractor to execute the steps they dictate. While it might be tempting to pick up some of those latter jobs to pay off some bills, it’s best to avoid them. Those are the same people berating the waiter at the restaurant for their steak not being quite medium-rare enough. A client who doesn’t value your expertise will approach any hurdles along the way as a personal affront. Having clear and similar expectations about the process and everyone’s roles helps things run smoothly throughout the project.
  3. Value perception. One thing is being lean, and a very different thing is being cheap. Some prospect clients start a conversation by asking about your process, your team, your experience. Then there are those who seem narrowly focused on costs, not so much to make sure you are aligned in terms of budget, but because they clearly want the cheapest deal they can get. It also shows that they’re not really that interested in what you bring to the table as much as using you as a way to get figures and go with the best deal, as one does when comparison-shopping for a new washer and dryer. You are not Home Depot.

These big red flags are different for everyone, but once you know what traits to look out for, you can spot these difficult types a mile away before wasting any time and energy. Becoming more skilled at choosing your clients is a catalyst to help your business grow. When you have good chemistry with a client and your values and expectations are aligned, the project is more likely to be successful, and the client will be more inclined to recommend you to their connections.

Despite all the fine-tuning and careful listening, a lemon will slip through once in a while, or you might get into a difficult situation with a good client. And that’s when I tap into the lessons I learned raising two very different but equally mystifying toddlers.

  • Lead with your reaction: when your two-year-old falls and scrapes her knee, half of what will ensue depends on how you react. If you get scared, she’ll get more scared. Same with an upset client. If you get defensive, they’ll escalate their point, and before you know it a massive tantrum unravels. And here’s the thing — grown-up tantrums have nothing cute about them. Your initial response to an upset client can literally make or break the relationship, so pause for a few minutes or an hour before replying to that nasty email or returning an uncomfortable call. Frame the problem in the whole scheme of your relationship with this client, and think about the most practical approach.
  • Pick your battles: in work life as in parenthood, there are things to get rattled over, and things that are not worth the fuss. If a client calls with a small change after having given you approval on something, it might not be worth it to make an issue. If it becomes a pattern, then you’d want to have a conversation about it. Again, being able to take a step back and look at the problem in the context of your work with this client will help you figure out if it’s worth standing your ground or if it makes sense to be more accommodating.
  • Don’t take it personally: this one is hard. When your toddler refuses to even smell the homemade macaroni and cheese you just spent 45 minutes on because it has crumbs on it, I can tell you from personal experience that it’s pretty tough not to be personally offended. Same goes for a client who gives you unnecessarily harsh feedback, or changes deadlines with no notice. Try to think about what’s happening on her end. She’s likely not doing these things with the goal of making you miserable. Like most humans, clients often pass on their stress to the people they work with, so chances are it’s not about you or your work. Take a breather, remove your ego from the equation, and assess the situation from a more neutral point.
  • Show them some love: just like young children, positive reinforcement is a healthy way to ease a sticky situation. Think of something positive to add to the conversation to get unstuck and help them take a step back too. There’s a reason why you’re working together, right? Remind your client that you appreciate them. You know I love working with you, and I’m glad we figured this out. Let’s schedule a time to talk about next steps tomorrow.
  • Move on: and I mean actually move on. Don’t think about sassier comebacks you should have used, or replay the interaction on your head. Take note of any lessons from the experience, figure out if you need to make adjustments to your relationship with the client, and focus on a different project to help you reset. Be productive with your time and energy, it comes in limited supply!

It’s hard being the adult in the room when someone is throwing a tantrum, but it comes with the job. Remembering that you’re half of the equation and adjusting how you deal with tough situations with clients will change your perspective, and in time, hopefully, lead to fewer tantrums.

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Teresa Lagerman
The Startup

Hudson Valley // Musing about donuts 60% of the time