My Client, The Dread Pirate Roberts

In the Princess Bride, the hero Westley is captured by the Dread Pirate Roberts and put to work on his ship. Each day, Westley works hard and impresses the pirate. At the end of every day, the pirate says “Good night, Westley. Good work. Sleep well. I’ll most likely kill you in the morning.” This exchange goes on for years. Eventually, the Dread Pirate Roberts acknowledges Westley’s contribution, makes Westley the new Dread Pirate Roberts, and retires with a fortune to a small island.

At Looker, I’ve run into the Dread Pirate Roberts professionally.

Early at Looker, in order to win business, we built many proofs of concept. We encountered customers who were helpful and enthusiastic, but sometimes we’d encounter the Dread Pirate Roberts (DPR).

In the service world, the DPR expects you to fail. They’re giving you a shot because you’ve promised something they want, but they’re skeptical that you can deliver. Other people have tried to satisfy them before, and they’ve failed. You’re expected to fail too. Every day, the DPR asks for something new. Every day, you pull a miracle. Every day, the DPR says, “I’ll most likely kill you in the morning.”

Working with DPRs #

Some of my favorite clients have started out as a DPR.

The trick to working with them is good communication about what you plan to do and, afterwards, what you’ve done. Be articulate, be confident in yourself and your process, and be patient. Above all, blow them away with quality of service.

At times, the DPR may push you in a direction that isn’t good for them or ask for a feature you can’t support. Don’t go. Don’t be shaken. Hold firm. Be articulate as to why you aren’t doing it and the value of your approach (“True Love”). This takes confidence. Many software companies have painted themselves into a corner trying to satisfy a customer who wanted something that didn’t fit into the product or wasn’t ready to be fit into the product.

Winning over the DPR #

At some point, there is a critical delivery. At Looker, that point is the proof of concept. We build a model that can be used to answer questions about the customer’s business. We show what we built, how it works, some insights we discovered, and then throw the room open for questions about their data. “Ask something you’ve always wanted to know about your orders,” is something we might tell an e-commerce company. The DPR will ask something very hard, and we’ll show them the answer. If we don’t have a way to answer it, we’ll build it right there in the room and add it to the model. Slain.

The Dread Pirate Fanboy #

The great thing about the DPR is that, ultimately, he or she becomes your biggest fan. Once you exceed expectations, you’re on the inside. You’re someone to trust, in a world where many are not trusted. There is no better reference than someone you converted from a Dread Pirate Roberts to a Dread Pirate Fanboy.


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