Note: as I’m currently evaluating and interviewing for product manager opportunities, I’m publishing many answers to the product, behavioral, business, and life questions I’m researching/practicing publicly rather than keep them private in a Google doc.

Tell me about your most difficult customer

I’ve dealt with many difficult “users”, customers, and clients.

At Zillow, we placed Zestimates on 40 million homes — it was inevitable some owners would disagree with those estimates of value. They did, and we heard from those users (they weren’t customers or clients since they weren’t paying anything for goods/services) via email and phone calls. Several were very irrational with their expectations, though the majority simply needed to be listened to & educated about how the service (and algorithm) worked. Occasionally, I’d get up from my desk and take a walk before responding to an email or writing a blog comment. One specific example I remember was a home owner in Florida who owned a multi million dollar home — with a Zestimate that was “500k too low” (according to him of course). The only acceptable response for the user was to remove the Zestimate from the website or change it to be “accurate”. Of course, neither of those things were going to happen (we never manually changed Zestimates or removed them from the website). I listened to him for 30 minutes, relayed what I heard back to him to ensure he knew I understood his concerns, and then talked him through the reasons for our stance of not removing/editing Zestimates. He didn’t agree with them, but eventually he did at least understand where I/we was coming from.

At Virtual Results, there were several difficult customers among the first 100 (I managed customers 1-100 of the Agent Plus platform). The most difficult ones were the ones who asked question after question about marketing strategy, and requested change after change on their website. I always approach interactions with unhappy customers with a desire to learn and improve our product/service offering — while always striving to do better next time. For better or worse, I am a pleaser — so had a hard time saying no to customer requests for help and advice. If I had the power to solve the problem, I did. The customers that asked for help, had access to free marketing consulting.

I’ve had several consulting clients who were challenging (at times) to work with. I’m not going to go into the details in a public blog post, but I will say there are two things that generally lead to difficult consulting clients: communication and expectations. Dealing with those two issues requires deep listening, questioning, understanding and empathy — along with good old fashioned execution.


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