Success Planting - Part 2: Asking the "Crazy" Question - ThoughtTrace
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Success Planting – Part 2: Asking the “Crazy” Question

Nov 23, 2019 Best Practices Digital Transformation

In Success Planting Part 1, we examined the differences between a Success Plan and Success Planting, but there’s more to the story…

Of course the “planting” half of the term Success Planting is an often used analogy to planting a seed and reaping the harvest. Here’s how the analogy plays out with a customer success organization. The crazy, thought-provoking question is the seed in this analogy. If the question is crazy enough, we can be fairly confident that the “seed” won’t take deep roots immediately, send a shoot high into the air, thicken into a mighty trunk, and send branches of shade in all directions. In fact, the best thing we can expect to happen the first time we ask that Crazy Question is a momentary grin as the customer can see the appeal of the idea, followed by the totally natural knee-jerk reaction of immediately thinking of one or two reasons why that wouldn’t work at their company, at least not just yet.

Getting Out of Autopilot

The test of a Crazy Question is not whether it is immediately embraced by the customer. Of course, it’s possible, but definitely the exception. There are two distinct indicators that the Crazy Question is indeed Success Planting. The first is that it elicited a strong reaction. All of us, customer success managers and customers alike, go through large parts of our days on autopilot. While this is necessary and usually beneficial, we all recognize that no real change or innovation happens when we are operating on autopilot. We are just going through the motions of a monthly touchpoint or other conversation. The Crazy Question is an effective tool to take the conversation temporarily of autopilot mode and shift to Success Planting mode.

Reimagining the Question

The second indicator that we’ve asked an effective Crazy Questions is seeing a change in our customer’s perception. It could be their perception of the problem they are really trying to solve, how our software fits as a solution, or a uniquely valuable way to reimagine long-held assumptions about processes and requirements that made perfect sense before using our software but not as much now. What do these changes look like? A few days after asking the Crazy Question, our customer might email a follow-up question, or we might ask a variant of the original Crazy Question and the customer engages rather than pushing back.

Ready for Part 3? Subscribe to the ThoughtTrace Blog to have Part 3 sent directly to your inbox. Also, visit our brand new ThoughtTrace Community site to learn more from ThoughtTrace users and even chat with our team. See you there!

About ThoughtTrace

In 2017, ThoughtTrace launched the first industry-specific Document Intelligence and Contract Analytics platform that provides value on day one with minimal training and setup. Leveraging AI/ML as a compliment to human expertise, the ThoughtTrace platform identifies critical obligations in contracts exponentially faster and with greater accuracy than traditional methods. ThoughtTrace reads, organizes, and surfaces data that gives users operational agility, actionable insights, and decision-making superpowers.


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