5 Digital Transformation Experts Share Advice on Turning Detractors to Excited Supporters

You won’t transform a business model, redesign a customer experience, or automate a complex business process without facing some resistance. And if leaders and employees line up to protect the status quo, your organization likely needs a cultural transformation.

Digital Transformation: Detractors to Supporters

One of the top questions I hear from Digital Trailblazers is about their struggles addressing detractors and how to convert them to enthusiastic supporters. Transformation requires working with people, addressing fears, creating excitement over the future, and evolving incentive models. One step is categorizing the types of employee reactions to a digital transformation and creating a playbook, at least in your mind, of ways to respond to objections and concerns.

Keep in mind that some detractor behavior is desired. We want peoples’ questions, ideas, and challenges. We want a collegial debate around our goals and must avoid what I call the hot potato culture, where people avoid sharing ideas and taking ownership of implementing solutions.

I dedicated chapters 9 and 10 of my book, Digital Trailblazer, to culture transformation, and here’s some advice I shared:

"Getting a detractor to become constructive is time‐consuming, but it’s part of the Digital Trailblazer’s responsibilities. So, at the outset, show patience and empathy with detractors. Demonstrate that you’re a good listener and a strong collaborator, especially when a detractor shares a valid concern, objection, or fresh idea." - Isaac Sacolick, Digital Trailblazer 

But I wanted suggestions from other leaders on their tactics for winning over detractors, so I scheduled a session of Coffee with Digital Trailblazers focused on this topic. I host this program almost every Friday at 11 am EST, and I was pretty sure I would get a crowd and some fresh ideas. Thanks to Joanne Friedman, Martin Davis, Tyler James Johnson, and Joe Puglisi for your contributions.

  • Joe – Get in their shoes and understand the individual and the source of their resistance. Many times it’s their fear of the unknown. Consider pairing a detractor with an expert or supporter. Use humor to diffuse or engage people’s listening skills.
  • Joanne – Show empathy to create trust. I bring Kinder Surprise - the chocolate eggs with the toy inside - because it releases endorphins and makes people smile, which helps build trust.
  • Martin - Find that one thing that will excite them, and get assistance from people they trust. Answer their WIFM (what’s in it for me).
  • Tyler – You won’t win over everybody, so find their influencers and collaborate on what winning looks like. Use agile to set expectations and avoid unrealistic expectations. Memorialize and capture the outcomes, especially after a lengthy debate.

Unfortunately, LinkedIn doesn’t record these sessions, so these are paraphrased, and I am sure I missed capturing several valuable lessons.

Arturo Garcia, CEO of DNAMIC has this advice. "It's often the small, simple steps that make a big difference," he says. "Starting small and incrementally is often the best way to approach a big change like digital transformation and automation in any business."

If you’re struggling with detractors, pushback, or lack of support, consider sharing your experiences with a mentor or advisor. You’ll build confidence over time as you handle different types of challenges, but advice from someone on the outside can bring new perspectives. 

Coffee with DigitalTrailblazers

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About Isaac Sacolick

Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld, CIO.com, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.