Two Questions Every Executive is Asking This Morning….

I used to run sales training sessions for direct B2B-focused sales teams. A portion of the session always focused on great questions sales people should ask their prospects. However, when you run a working session and ask the sales people what questions they use, you always get a few ones that make you cringe.

For example….


What keeps you up at night?

I used to hate this question. The reason I hated it is because you never know what is actually keeping the client up at night. I typically answer this question with “my 1 year old keeps me up at night”, immediately leading to awkward silence and a sales person trying to back out of a hole.

But the more that I think about it, while the baby is what wakes you up (or the bump in the night, or the ambulance passing the house, or someone’s snoring), what keeps executives up are two questions they ask themselves this time of year:

  1. What else can we do to achieve our in-quarter targets?
  2. What strategies do we need to put in place to drive our performance next year and beyond?

What is interesting about these questions is that I find both of them lead back to a common theme.

How well do you understand your buyer, and what are you doing today and in the future to align more effectively to their buying journey?

In the short term and to achieve in-quarter results, that can mean –

  1. Using predictive analytics to identify opportunities to fast cycle sales or identify markers for promising cross-sell opportunities
  2. Enabling sales teams with more focused buyer research and account based marketing to ensure that sales messaging and value propositions are crisp and clear
  3. Making better, faster decisions on the plays you should run from the laundry list of plays you could run

Shortening the sales cycle by just a week now means a higher likelihood that a deal will close this year and that firm revenue targets will be achieved. This blog post shares some short term tactics which can deliver improved in-quarter performance for organizations.

In the longer term, executives are struggling with a rapidly changing customer environment and need to rethink their strategies given the change. The changing buyer’s journey and customer experience expectations means that executives need to build plans which include:

  1. New channels to their customer which incorporate online and digital engagement models to align to how customers want to interact (and which in turn reduce the cost to sell and serve to these customers)
  2. Better data assets and analytics capabilities to build prediction into the decision processes of the organization, leading to improved return on marketing and sales expense, greater revenues, and reduced costs
  3. New technologies to incorporate into yesterday’s go-to-market model to drive efficiency, effectiveness, and alignment to how customers consider purchases and buy today
  4. Improved “connectivity” between marketing investments and sales/revenue outcomes to ensure closed loop measurement and reporting (which CEOs will continually demand from their commercial leaders)

Our whitepaper on the New Buyers Journey shares some insights into how organizations are adapting their strategies given the changes in today’s customer.

Both of the “keep you up at night” questions are crucial to answer as we approach the end of the year. I would love to hear how you are answering them and how you weigh the importance of each.