Pretend you’re acting… especially with difficult clients

I have a private confession: once upon a time, in my mid-20s—which was far too old for the sorts of learnings that most people figured out ten years earlier—I was so shy, I wouldn’t talk to people I didn’t know. And I was twice as silent around cute girls I was attracted to. This, almost tautologically, made it near impossible for me to meet people either to befriend or to date. And the cold weather of New York City (cold physically and spiritually) accentuated this.

So, I devised a plan: I’d pretend I was a “cool kid.” What would the canonical “cool kid” say or do at that particular moment? (Wiser people ask themselves, “What Would Jesus Do?” but I asked myself, “What Would Serge Gainsbourg do?”) By implementing this trick, I tricked myself—I tricked my brain—into letting me act in ways that the “normal” me would never do! Normal Me would think, “O-M-G, I feel like such a loser being the only person in the bar, let me leave and come back later when it’s full” and I would just leave. But the cool kids from my high school who were my inspiration were the sort who would just go, sit down at the bar, all alone, not even glancing at anyone else, with a smirk on their face. Often taking out a cigarette and lighting it (this was precisely the era when New York was in the process of making smoking inside restaurants illegal, the waning days of a bygone era.) Why not just act like them, strut over to the bar, and sit there with a smirk on my face, acting like I didn’t care whatsoever what anyone else thought. Guess what happened?

After about two years of acting the part, I started internalizing the role and I started building up the confidence I pretended to have.

Over the years, doing more and more client and consulting work, I realized that this pattern applies more broadly: this lesson of acting like someone else can give you the confidence and creativity to take on roles you feel awkward about. It applies to much more than dating: it applies, deeply and seriously to the professional world too. Especially when dealing with clients—and especially squared with difficult clients. And every experienced designer has had his or her share of difficult clients!

For some people, acting comes naturally. I’ve met more than one MBA who could turn “on” or “off” an asshole switch as needed. They’ll be an asshole one second and invite you for a beer the next! But I’ve found that most designers have a harder time acting like someone else. Perhaps because good design is born out of an artistic spirit inside you, so you can’t change yourself without killing off your own spirit?

But sometimes it is important to temporarily take on different roles—especially for designers dealing with difficult clients. The summary of my acting lesson, in a client context, is this: sometimes you need to be tough with a client. And as a nice guy, I hated being the bearer of bad news. I just want to design the client’s web page or logo, not deal with annoying people. I didn’t want to be tough. I wanted to shirk away. But I knew saying the tough words was the right thing to do and would ultimately make the project go better for the client and for me. But I could never do it, although I knew I needed to. I constantly thought, “I wish I someone else to deal with this; I just want to spend my time creating elegant designs.”

So, what did I do? I acted. I said to myself, “I know this great businessman and great communicator named Charlie. What would Charlie say in this situation?” I just pretended to be Charlie!

One time, for example, a client was procrastinating on paying me. As a nice guy, I waited and waited, and sent him gentle emails about every 3 days over 6 weeks. But he rarely responded and when he did, it was just to tell me it’s coming soon, which was a lie and we both knew it. I asked myself, “What Would Charlie Do?” I guessed that Charlie would probably say something worded nicely but absurdly strong. Based on my strategies, I could say a Charlie-inspired speech that was something like this:

“Look. I know I did a great job, worked hard, you were happy with the results, so you need to pay me for my work, as we agreed upon. It’s only $2,000, and you can afford it. I’ve never let anyone get away with not paying me, and I’m not going to start now. So, here are our choices. You either pay me now or I’ll let you know a policy of mine: I never cause any problems unless someone f—s with me, and I have a policy that if someone does f— with me, I will use 20x the money that they used to try to hurt me to get back at them. So, you pay me the $2,000 you owe me within the next 5 days, or I will commit to you now that I will spend up to $40,000 to make sure you do.”

(Note: that does happen to be a policy of mine, so I’ll remind you: you shouldn’t lie since it’s both immoral, and everyone can see through it. Make sure your policies are actually your policies.)

And guess what? He paid within 5 days. 6 weeks of being the “nice guy,” with no results. One strong email and BAM—problem solved.

There is a broader lesson I learned here, from many situations like the one above, taken together. Over the years, acting like a tough guy has turned me into a tough guy. Acting like the cool kid helped me morph into at least a substantially closer-to-cool kid than I was before. Could it be that acting a role, for enough time with enough intensity, ultimately changes you into the role you play? If this is indeed the case, then be warned: acting can be helpful but choose what roles you play carefully. If you act like an asshole enough, you may just become one.

Learn With The Best

Morgan

Morgan has led digital for multiple presidential-level campaigns, has run 92+ person agencies in three continents, and has lots of experience managing challenging clients. He’s spent 11 years compiling the refining the list of his best managing-up practices that became the core of this course.