Jumpstart Digital Transformation: Advice on How to Guide Tech Innovation Leaders

Our greatest thinking moments for developing ideas, innovations, and inspirations occur when we take three steps away from our daily grinds.

On some days, you achieve this by taking a long hot shower. Other times, your mind opens up while immersing in intense physical activity. I prefer biking and hiking and usually have a phone ready to record an idea or insight before I forget it.

Isaac Sacolick in Digital Trailblazer

But that’s not what I am asked now, finishing my third keynote in as many weeks.

The question comes from an IT leader frustrated with the moat that separates top-down strategic plans from bottom-up ideation and experimentation. His hand raises as he sees me explain who are Digital Trailblazers and the context of my new book covering the essential lessons to jumpstart transformation and accelerate technology leadership.

Here’s what he sees:

“Your business will need more transformation leaders – what I call Digital Trailblazers—who can lead teams, evolve sustainable ways of working, develop technologies as competitive differentiators, and deliver business outcomes.” - from Digital Trailblazer published by Wiley

And his question is, “Isaac, how do you guide Digital Trailblazers on bringing their best ideas forward and help them through the bureaucracies that tend to throw boulders in their paths?”

His question targets a significant cultural gap between leadership and agile mindsets. It’s agile, design thinking, and data-driven experimentation versus the ivory tower multiyear strategic plans still favored by some investors, boards of directors, and leadership teams - especially for businesses that grew up long before the digital age. 

Leadership says they want to develop intrapreneurs and “act like a startup.” Some will create ideation processes in their PMO, but I find it far less common for leaders to break away from the sacred cows on how they prioritize, fund, and reward experimentation. 

How to jumpstart transformation

I choose my words carefully, and there’s a good reason the title of Digital Trailblazer includes “jumpstart transformation.” I tell stories of the good and bad in Chapter 9, but please read chapters 1-8 first - you’ll need the context. 

Answer the question before jargon

Today, back on stage, I have to follow my own advice from Chapter 4, “Answer the question before steaming through jargon-filled details.”

So here’s how I answer the question. “I ask Digital Trailblazers to draft their vision statement. I then ask them what questions they need to answer to build confidence in their idea and whom they need to work with to help answer them.”

I let that sink in for a moment. It’s a simple and intuitive answer, but guiding Digital Trailblazers requires understanding these innovation practices.

Provide Digital Trailblazers a path to develop their ideas

Let me break down my answer into a repeatable innovation practice.

StarCIO Vision Statement

I recommend downloading my vision statement template as a starting point because it requires identifying target end-user personas, value proposition, and the strategic importance of the initiative.

Identifying the questions that flush out end-user benefits, unknowns, and risks isn’t easy. I find that some innovation leaders need guidance on what questions require researching answers, and others develop long question lists and struggle to prioritize. Help the Digital Trailblazer identify the questions that provide clarity on the opportunity, identify risks, and develop a plan.

Then there’s the end of my answer where I want to know “whom they need to work with to help answer them.” It’s a way for the Digital Trailblazer to reflect on what resources they require and whom they would like to recruit to their team and kick off an agile planning process. Because once there’s a team and a prioritized list of questions, I expect they use scrum and agile methodologies to work through a continuous planning process.

But what about helping them through the bureaucracies?

Here’s the thing - it’s not a one-size-fits-all answer to address bureaucracies and advise on culture transformation.

Every organization has its institutional practices; some work well, others are necessary, and many need rethinking for a smarter, faster digital, data-driven age. What bureaucracies need bulldozing to make way for a more agile and collaborative process, and which ones should the transformation leader prioritize as a starting point?

The answers lie with your Digital Trailblazers! As they answer questions, build confidence in their idea, and develop a plan, identify what boulders are getting in their way. 

That’s where you start, and that’s the first step to jumpstart transformation.

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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.