How Do You Know? — A Central Question to Customer Success

Dave Duke
MetaCX
Published in
3 min readJun 7, 2018

Several years ago I was at a happy hour with a few colleagues. Included in the group were a couple of friends who had just landed new gigs at one of Indianapolis’ newest startups, Octiv (originally TinderBox). We were discussing the new project and learning about their software offering that was going to tackle the sales proposal management process. Within the conversation the VP I reported up to threw out an awesome question. As he was digesting what the new startup was doing, he responded with the idea that the solution would be helping answer the question, “how do you know?”

His point was that the software solution that Octiv was building would, for the first time, give a view into what was actually happening within sales proposal documents - one of the most critical aspects of the sales cycle. With visibility into the ways in which prospects and customers are interacting with the proposal documents, sales teams could leverage the data and insights to navigate the sales process in a new way. The software would help answer the question.

You could argue that one of the primary roles of software is to help answer this question. There are so many facets to software adoption and usage, but the nature of software provides more of a view into what is happening and what is not. It’s the beauty of digital transformation - we have more data than ever before to solve hard problems, guide our work and make strategic and tactical decisions.

I also think this question can be an extremely powerful North Star in Customer Success. It can be used in so many different ways to help us navigate the management of a customer relationship and a customer base as a whole.

Questions like…

  • How do you know what your customers are doing?
  • How do you know if your customers are accomplishing their goals?
  • How do you know if your Customer Success Managers are doing the work that they should be doing?
  • How do you know if your software is solving the right customer problems?

It is such a powerful way to think about the ways in which we are pushing ourselves to grow and improve our teams. I believe it can help us execute on the customer success promise to deliver value to our customers through our products, services and relationships. We should be working hard to answers these questions and others that help us manage the needs of our customers, employees and internal stakeholders.

It would be unfair to say that everyone struggles with this topic all of the time, but I would venture to say that the majority of us can improve. Sometimes we need a guide as we work through the day to day grind and perhaps leading with the question of “how do you know?” can be a North Star for those working to better understand their customers and employees. I believe that bringing this question more to the center of Customer Success strategy can be a helpful aide to Customer Success teams.

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Dave Duke
MetaCX
Editor for

Customer Success leader and practitioner, Chief Customer Officer & Co-Founder at MetaCX. Eager to explore CS, CX ideas & anything else that inspires.