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.
But that’s not what I am asked now, finishing my third keynote in as many
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 through 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
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
I let that sink in for a moment. It’s a simple and intuitive answer, but
guiding Digital Trailblazers requires understanding these innovation
Provide Digital Trailblazers a path to develop their ideas
Let me break down my answer into a repeatable innovation practice.
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