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Five awwwkward client situations 😬



When you take a new gig, you’re not just taking on the project—you become enmeshed with your client, the corporate culture, and other important aspects that can take a backseat when you take a gig. In reality, the client is just as important as the work. Your success hinges on that relationship: open lines of communication, ability to resolve issues, and other nuances that we can fail to recognize early on.


Fortunately, I've been quite lucky that I've had dozens of wonderful clients. But when we get surprises (the bad kind, not the good kind), that adds a whole other element to the client relationship. It can throw the dynamic into a dysfunctional stratosphere.


Here are some vexing situations I’ve dealt with over the years. And yes, “I will Survive” plays in the background.


#1 Working for an ex💔

Everyone in Silicon Valley knows there is the possibility of running into colleagues, ex bosses, and plain exes, but that doesn’t mean we want it to happen. Five years ago, I faced a blast from the past at a global software giant: a guy I dated 15+ years ago. As luck would have it, he happened to be my new client’s boss. Thank God we ended on good-enough terms (translation: we didn’t hate each other). I did my best to get ahead of the weirdness by reaching out on LinkedIn before the first day with the “small world” angle. And it certainly was—my cube ended up being six feet away. But when my client left not long after I started, I reported to my ex for more than a year. We would engage in small talk or we’d have a business interaction. When our team went out for drinks, we had two minutes to ourselves and congratulated each other for our valiant efforts. Overall, things went as professionally as they could have, but I also realized how lucky we were not to be enemies when we parted. We made the best of an awkward situation, but I'd be happy to see an ex on a random evening out—not at the workplace.


#2 Working for your intern👶🏼

When contracting for a large semiconductor company over a decade ago, my client told me there was a new director of the marcom group that I would report to. It shocked me to hear the name: an intern I hired over 25 years ago when I had a regular "day job." Initially, I was proud to think about this grown adult: my whip-smart, entertaining youngen, who oozed creativity and charm. But I never thought he’d end up as a director, or did I really groom him that well? In his role “supervising me,” we laughed about the irony and coincidence, but underneath, there was an undercurrent of uncomfortable. We went for the requisite “get to know each other again” lunch, where he praised my tutelage preparing him for success. But the power had shifted, and we were both aware of that. That dynamic continued working together on a trade show. Fact is, I could never embrace reporting to someone I still saw as a baby-faced, 20-something. Worse yet, he would often make corrections on seemingly minor items, among other boss-y moves. Or was I just being overly-sensitive? After this gig, I gained new wisdom about myself: I was so used to starting engagements as an equal partner, but this felt lopsided because of who he was. And I just had to be OK with that if it ever happened again. Luckily, I've only had one intern.


#3 Firing a horrible client🙅🏼‍♀️

This is a topic not discussed much because it rarely happens "in public," and in some circles could be perceived as reflecting poorly on the freelancer (You must have done something to piss them off, right?). But there’s also sanity to consider, not to mention self-respect. In a period when I was hearing crickets instead of the email chime for a new gig, I interviewed for a gig at a well-known but forgettable virtual computing company through an agency. They wanted someone ASAP. It didn’t pay well. Annnnnd, the client was having a hard time finding a fit. All bright, glaring red flags. The client turned out to be a young woman who seemed to revel in at being as unlikable as possible. She cracked a smile one time, I think. She even said during the interview, “You’ll hate me after working with me for a while.” Props for her honesty, but it happened sooner than I imagined once hired. Just a few examples: dictating edits over my shoulder as I type on the computer; telling me what time I should go to lunch; calling and texting at all hours. Another freelancer working for her was about to blow a gasket too, so we ended up quitting on the same day not long after. The client positioned it to her boss that she fired us—but we knew the truth. In the end, I learned that following your gut always pays off, even if it means holding out for better work. It's worth every penny that you'll lose in stress.


#4 Colleagues that turned into client nightmares👹

"Fool me once, shame on you; fool me twice, shame on me." Remember that saying? I’ve had that dynamic play out in my freelancing career under similar circumstances, but a year apart. I knew both people as employees of a client, folks I interacted with and enjoyed but didn't work for. But when they asked me to join them at a new company in a consulting role, much to my surprise, they behaved completely differently. Micromanaging. Quick to flare. Poor communicating. Difficulty managing their team. The list goes on. It became extremely awkward to navigate the relationships, contrasting with the positive connection in a prior life. I felt at sea. I questioned myself. Did I not see these traits as a colleague? Was I too far away from it? Or was it that I just didn’t know them very well? I’m fine working for colleagues, and even friends (those gigs have worked out splendidly!). I doubled down on that reminder that it’s critical to talk to your colleague or friend about an upcoming gig first and how to handle situations if they go astray. Use that good relationship to fortify the foundation and discuss your new dynamic, or you could be in a world of hurt.


#5 Revoking a colleague referral ⛔️

Just last year, I was connected to a client at a fintech startup through a LinkedIn colleague. I always appreciate word-of-mouth and prior to this engagement referrals have worked out quite well. The contract came through quickly, but strangely, the first assignment wasn't even mentioned in the work scope. Ummmm...what's wrong with this picture? Worse yet, it was a rush job. Even more alarming, the project changed again. I could barely keep up with the tailspin of changes in just a week and never got straight answers why. Initially my bigger concern was that they were a referral and wanting to give it more time before I bailed. But I knew I had to step away from the insanity, especially when I got pushback on paying for the hours I already worked. No gig is worth a chaotic client. After a lengthy back and forth on Slack, I resigned, citing numerous issues. They went with the "startups are a crazy place" excuse—but that didn't fly with me. The person didn't want to take responsibility for doing a poor job managing the work. I realized that a referral is 99% great, but there's always that 1% that doesn't work out. Even more importantly, I have to take care of myself and not worry about what the person that referred me knows or thinks—what matters is my experience after the referral.


I’ve learned important lessons from all of these cringy client moments, and as trite as it sounds, it’s made me a better freelancer. I can’t predict who my next client will be, but I can prepare much better with all this experience behind me—even if that means walking the other way.

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2 comentarios


Jim Brennan
Jim Brennan
09 may 2023

I'm glad we didn't have any of these moments...at least I think we didn't...

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Janice Cuban
Janice Cuban
09 may 2023
Contestando a

Of course not! You were and are one of my faves!

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