3 Signs You Have an Ambitious Digital Trailblazer Excited to Lead Transformation Teams

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 model.  

Identify Digital Trailblazers Excited to Lead Digital Transformation Teams - Isaac Sacolick

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 transformation leaders?

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 best practices. 

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 Digital Trailblazers.    

2. Digital Trailblazers pause, think, and then ask questions

Digital Trailblazer Innovation

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

Digital Trailblazer by Isaac Sacolick

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 results.

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.


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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.