How To Know Your Organization is Committed to Digital Transformation

Over the last four years, I've helped dozens of business leaders kickoff, plan, and execute digital transformations. Early in this process and throughout the program, leaders must engage a growing number of people in their organization on the goals of the transformation, current status, and near term objectives.

Committed to Digital Transformation? - Isaac Sacolick

Whether that leader is standing in front of a crowd in a town hall meeting or engaging the staff through a Zoom call, she or he has a few questions on their minds:

Are they getting it? Am I delivering the message clearly? Will they drive the next steps?

Look for These Three Signs of Organizational Readiness

Every time I deliver a keynote, I have these same questions. And as the speaker, you have to train yourself to look for the three most important signals:

  • Are people engaged and active listening?
  • Are they committed to the objective?
  • Do people know what to do next?

Engagement is something you can start measuring at the meeting, while commitment and follow-through are often steps you must observe and measure afterward.

When I see all three happening in an organization consistently, I know they are committed to digital transformation. 

Here are some steps to take before and during these meetings to get the teams' commitments.  

Prepare to Drive Home the Message

A successful delivery starts with the speaker themselves. If you are not prepared or haven't prepared the attendees for the meeting's objectives, then it's a hard uphill battle to achieve the required engagement levels. 

It helps to work your message backward:

  1. What is the desired outcome for this meeting and afterward?
  2. What messages and directives do you want people to learn,  understand, and acknowledge?
  3. Who needs to be there, and who should you prep to be an insider to your objectives?
  4. What supporting material - especially data, stories, and acknowledgments - will help people understand your problem statement and its importance?
  5. What is the current context - what the attendees have top of mind when they join the session?

All of us tend to prepare our talks in reverse of this order, start with context, add all the details, and then figure out the outcomes' specifics. But next time you are preparing for a talk, try working it in this order, and you'll end up with a message that's more direct and actionable. 

Optimizing the supporting material is essential. When I deliver keynotes, I'm told to fit the message into a time window. Sometimes I have as little as ten minutes, while other keynotes can be forty minutes or longer. 

Anyone who sees me speak knows that I struggle with #4 and overload my keynotes with too many details. This may be ok (I hope) in a keynote, but less is often more when speaking to your team and colleagues. 

I always recommend including some data (share the truth), tell a relevant story (get attention), and acknowledge realities (empathize) as a recipe for driving home a message/

Determine the Engagement Level During Meetings

There are a few signs that I look for during meetings that indicate engagement and commitment:

  • Are people making eye contact?
  • Do enough people ask questions?
  • Do attendees answer questions with conviction?
  • Do people look excited (and not bored, overwhelmed, etc.)?
  • Is there dialog or even debate on any objective that ends with an agreement?

There are all signs of active listening and engagement. If the attendees are out to lunch, then chances are they aren't going to follow through on driving the desired outcomes.

As a speaker, these are all indicators that can readily be observed. If they're not happening, then you might need to audible and get people's attention. 

Call on one of your insiders. Get people moving, Change your voice levels. Show emotion. Engage attendees with questions that they can raise their hand to respond to. Disrupt yourself if you have to!

Observe and Drive the Commitment

Commitment to driving digital transformation isn't going to be done in a meeting. It's all in how people understand their roles, the objectives, and then self-organize on a course of action.

But I'll leave that for a future post.  Until then, better make sure your team doesn't have these five signs of a hot potato culture.

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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,, 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.