5 Things Digital Transformation Leaders Should do this Summer

Last year, I posted 5 things CIO should do this summer as a reminder to CIO to get out of the weeds and smell the roses. So this year, here is a follow up post on what digital transformation leaders should do this summer.

And not just CIO! CDOs (digital and data), CMOs, and all of the key leaders driving different aspects of the transformation program.

Leading digital transformation is stressful. A big part of organizations that are successful recognize that changing organizational practices and driving culture change is a critical success factor. That's not an easy job! So my recommendations are around taking the stress out of change management and driving culture changes while pursuing transformation objectives -


  1. Road trip to a handful of customers - Summer brings a great opportunity to visit select customers that may be too busy to engage during the spring and fall. Double down by making it a road trip and bonding with a few colleagues during the drive.
  2. Brainstorm with the team - Summer is a great time to bring the team together to review opportunities, debate approaches, and research new solutions. Since you're likely to have people taking vacations during the summer months, consider having a series of smaller brainstorming sessions around tightly defined topics. Leave more broader and strategic brainstorming sessions to the fall when you are more likely to have full attendance.
  3. Get hands on with customer data - Even though it's the summer, that doesn't mean that you can slack off! With fewer people around to make strategic decisions, consider beefing up your understanding of customer needs and sales opportunities by rolling up the sleeves and reviewing some aspect of your customer or sales data. Don't have a good tool? Review my recommendations on selecting a self-service data visualization platform
  4. Bring treats to difficult meetings - I like bringing chocolate, fruit, and if appropriate an alcoholic beverage. A key aspect of transformation is bringing multiple stakeholders together to leave sacred cows behind and drive a future vision. These can be stressful meetings, so showing up with an ice breaker helps get people to open up and drop their guard.
  5. Read books together  - This is a shameless plug to those who haven't read my book, Driving Digital: The Leader's Guide to Business Transformation. If you need other ideas or inspiration, check out Martha Heller's CIO recommended reading list for 2018. If you prefer podcasts, consider listening to some of the great CXO Talks.

Don't let the summer sunset! 

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