High Maintenance (“When Harry Met Sally” Style)

“You’re the worst kind. You think you’re low maintenance but you’re actually high maintenance.” Harry to Sally

Unless you specialize in the uber-difficult, one of life’s small victories is isolating and politely turning away high maintenance, suck-you-dry people.

Clients. Customers. Colleagues.

The obvious culprits are easy to spot and you can often quickly escort them out of your orbit.

But the Harry Met Sally type is a different breed.

I once had a colleague “Samantha”, who was smart and super-talented with a delightfully spunky personality. We got on like gangbusters until we decided to woo my client together.

He’d been wrestling with a thorny problem and he readily agreed to meet us for a little brainstorming over lunch.

Rom-com it wasn’t.

Samantha arrived to our table five minutes late and couldn’t find any thing on the menu that worked for her. After much discussion, she settled on a combo of two salads with three ingredients removed and half the dressing on the side. Oh and could the waiter please bring some extra vinegar? Her beverage must be ice-free (ice in a separate glass) and delivered with a plate of lemon and lime wedges. The bread and butter had to be removed from her sight and she plopped both down unceremoniously in front of the client.

He indulged her for a few minutes and then sheer annoyance crossed his face (she missed it). He quite uncharacteristically proceeded to ignore her for the rest of the lunch. She had several more tête-à-têtes with the waiter as I tried to spark the brainstorming I’d promised. Did I mention Samantha was a communications expert? And no, of course we didn’t get hired.

I got smarter after that. Just because a colleague, client or buyer seems low maintenance at first blush doesn’t mean they will stay that way.

So now I look for a few cues of possible trouble ahead:

  • They may have trouble empathizing and be genuinely shocked if you call them on their behavior.
  • They may change their minds with frustrating regularity—they don’t just experiment, they boomerang their opinions until you’re dizzy.
  • They may do a preemptive favor for you because they want something in return—only the “favor” winds up costing you time, energy and/or money.
  • They have a bone-crushing deadline they’ve known about for weeks, but spring on you suddenly.
  • They may masquerade as a potential client, ally or “friend” (especially in social media) as a way to snag free services or inside knowledge.

Approaching every interaction with in-bred cynicism is no way to live, so I tend to err on the side of optimism. Most humans want to be good people and do great work.

But that doesn’t necessarily make them the right client for you.

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  • I have made similar mistakes myself. One was many years ago, with a major business relationship. I invited someone to become my business partner who I should never have trusted. I learned an important lesson.

    Most of us are mesmerized by some sort of characteristic. We all know people, often men, who are mesmerized by beauty, and commit to things, like marriage, with beautiful people they would never have done with a plainer person. I am mesmerized by both intelligence and high energy. All those years ago, I entered a bad business partnership because the person was quite smart and quite energetic.

    “Know your weakness”, and ALWAYS ask yourself if you would be engaging with someone with mesmerizing characteristics if she or he did not have those characteristics. That question has now served me well for over twenty years.

  • Excellent ad vice for us all. Good that you you emphasize it am not just be a client prospect but another concultant,

  • I’m glad I clicked through the newsletter on this one. This story was a needed reminder for me and I’m sure for lots of others who deal in service/intellect based work. As people have become more savvy the open “can I pick your brain” requests seem to have dropped, but the new “friends” via social media who want lots of free advice or services…they keep coming and coming. I believe you are right and that most folks want to be good and do good. It’s up to all of us to not only pay attention so we can spot the uber-difficult, but to guard against slipping into those patterns ourselves. Enjoyed this.

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