The premise of my new book, Digital Trailblazer, is that
organizations need a growing number of people ready to step up and lead
digital transformation initiatives. If it’s just the CIO, CDO, CEO, or other
executives driving the mission and values, then the transformation won’t
have the leadership needed to produce business impacts. Executives need more
Digital Trailblazers ready to deliver innovations, ongoing improvements to
customer experiences, analytics capabilities, and changes to the business
Over the last few weeks, I completed three keynotes for technology leaders
and asked the same question. “Isaac, how do we identify Digital Trailblazers
in our organizations?”
Now every organization has its methodology to identify and mentor high
potentials (i.e., the “HiPos”), and that’s certainly a good place to start.
But in my experience, Digital Trailblazers are a subset of HiPos, and some
Digital Trailblazers will never be identified as HiPos.
I consider several criteria when identifying Digital Trailblazers, and
here’s a good place to start.
1. Digital Trailblazers are hands-on and quickly shift to hands-off
It’s easy to say, “lead by example,” but what does that mean to a product
manager, technology delivery leader, data scientist, or other aspiring
In Digital Trailblazer, I advise readers to get in and out of the
weeds in several contexts. It means getting into the details but then
stepping out of them, identifying the patterns, and guiding teammates on
For a product manager, it may mean stepping into a customer’s shoes for a
couple of days but then coming back and sharing the experience and insights
with their teams and colleagues. A technologist may roll up their sleeves to
start a proof of concept on new technology but will collaborate with
teammates to quickly take over the job and complete defined objectives. A
data scientist will document their algorithms as they experiment and pave
the ways for others to take over their work.
Digital Trailblazers never leave the world of being hands-on, and I know top
CIOs, CTOs, and other leaders who are very happy getting into the technical
weeds. But it’s the ability to know when to get into them, how to get out,
who to bring on the journey, and what guidance to leave them that separates
2. Digital Trailblazers pause, think, and then ask questions
Transformation teams need leaders ready to ask questions and challenge the
status quo. When reviewing a business operation, they may ask, “What’s the
history behind why we do these steps, and what are their impacts?” When
considering how to prioritize a set of customer-facing features, they may
challenge stakeholders by asking, “Which personas will take advantage of
this capability, and how large is this segment?”
Now a highly extroverted leader will not struggle to ask challenging
questions, but the question is, are they selecting optimal ones and
verbalizing ways that help people think differently?
In my experience, Digital Trailblazers are highly strategic about what
questions they ask. They pause and think before raising them. Their
questions are open-ended, without showing any bias toward their
perspectives. They seek opinions from multiple perspectives by asking
compound questions requiring qualitative and quantitative responses.
Digital Trailblazers remind me of outstanding journalists who know when and
how to ask questions that require reflective thinking, and that’s a key
behavior required when driving transformation.
3. Digital Trailblazers teach as collaborators
One of the hallmarks of Digital Trailblazers is that they are lifelong
learners, enabling them to learn how markets are evolving, what customers
desire, and how technology capabilities can create competitive advantages.
What we learn today will change dramatically over the next couple of years,
hence the need to be lifelong learners.
But learning isn’t enough. I don’t need a team of the smartest people in the
rooms because that doesn’t drive transformative thinking or business
Digital Trailblazers are teachers and share the depth of their knowledge and
breadth of their experiences with everyone in the organization regardless of
rank, background, or location.
But they have unique teaching ways. They teach well before they are experts.
They’re willing to be wrong and learn through the process, making them
collaborative teachers. They facilitate the conversation and hold back their
opinions and beliefs and let other voices share their perspectives before
them. They know how to close conversations by resharing key learnings,
identifying decisions, and prioritizing follow-ups.
Their approach helps drive consensus without asking for it and ensures that
conversations lead to decisions and actions.
And these are key skills for Digital Trailblazers to lead digital
transformations. You need the conversations to change people’s mindsets, but
knowing when to shift gears to defining actionable next steps is a craft
learned through experience.
My new book, Digital Trailblazer, is packed with stories and learning
for aspiring transformation leaders. I hope you will read it, and stay tuned
for programs that I am introducing to guide Digital Trailblazers.