Ask These Revealing Leadership Questions When Recruiting Digital Trailblazers

Ask CIOs about their top issues executing their digital transformation programs, and you’ll hear three common problems. Some have concerns about whether executives are aligned on strategy. Others acknowledge technology leader skillset gaps. And a third group recognizes struggles in leading change management efforts.

At the heart of all three issues is the lack of the right people, culture, and digital practices necessary to deliver business results from transformation initiatives. Each of these problems point to leadership gaps, not technology challenges, suggesting that CIOs need to be more thoughtful about who they hire and how they mentor leaders assigned to digital transformation initiatives. 

CIOs need a specific type of leader to drive digital transformation results: the digital trailblazer. Knowing how to identify, recruit, and mentor this breed of IT leader is critical, but it requires CIOs to take some different tactics.

Who are the Digital Trailblazers?

Having spent more than 15 years leading and advising digital transformation programs, I’ve seen some patterns emerge among those best-equipped to direct these efforts. Digital trailblazer is a term I came up with for my recent book to describe the right kinds of leaders to drive digital transformation. Before I get into how to recognize and recruit them, I’ll explain how I define them.

Digital trailblazers develop competencies in multiple transformational disciplines and accept leadership responsibilities on digital transformation initiatives. They may hold C-level, VP, and director titles or sit further down the organizational hierarchy in positions as agile technical leads, product managers, or architects. They typically have experience leading people and projects as agile development leads or scrum masters, network operations managers, data governance leaders, or product or program managers, for example. 

But being a digital trailblazer is less about having held a particular role or responsibility and more about displaying an outcome-driven leadership style. A digital trailblazer must be a collaborative partner when working with teams, a vision painter when selling ideas to stakeholders, and a change agent with the courage to ask questions and challenge the status quo. 

Digital trailblazers are lifelong learners, continually developing both the depth of their technical skills and the breadth of their leadership styles. They seek out transformational roles in different types of initiatives. And they can combine seemingly contradictory capabilities. They are driven, but also empathetic. The digital trailblazer’s decision-making is deliberate and data-driven, yet also instinctive with an acute understanding of which lever to pull, when, and how hard. They know when to go fast, how to be safer, and where to drive innovation.

CIOs Realign Their Organizational Structures

I recently shared an excerpt from Digital Trailblazers on the Heller Search blog about the importance of nurturing high-potential talent into transformation leaders. However, hiring and mentoring digital trailblazers may be a marked change from how CIOs have recruited or managed their leadership teams in the past, when the focus was on functional leadership of software, operations, security, or program management linked to clearly defined sets of skills and experiences.

CIOs will typically hire and mentor digital trailblazers to assume one of two key mid-level roles that come together to drive transformation forward:

•    Product managers who identify target customers, define value propositions, develop vision statements, collaborate in defining roadmaps, inspire the development of delightful customer experiences, and oversee change management efforts.
•    Delivery managers who research solutions, establish platform architectures, excel at continuous planning, deliver agile releases, enable automations, drive data strategies, and create service delivery functions. 

CIOs can pair product and delivery managers to oversee a transformation initiative. In addition, IT leaders can recruit more senior digital trailblazers to define digital transformation competency standards and provide oversight on a portfolio of initiatives. And they can identify less experienced digital trailblazers to take on roles such as agile team leaders, agile product owners, and architects. 

Questions to Ask When Recruiting Digital Trailblazers

CIOs should be recruiting high-potential leaders and external candidates into these digital trailblazer roles. But identifying likely digital trailblazers can take more effort than looking for experience in a specific role or a technical competency. Instead, there are a set of attributes common to digital trailblazers that CIOs will need to tease out with targeted questioning.

Following are five key characteristics of digital trailblazers, and the questions I’ve found helpful in identifying them:

•    Lifelong learning: In what ways have you invested in yourself over the last few years? What did you learn, why, how, and where did you apply your new knowledge?
•    Curiosity and creativity: Can you share an example of a solution you helped develop? How did you evaluate and validate the approach?
•    Aspirational leadership: Could you describe an experience that exemplifies your leadership style and values? What did you get right, and what did you learn from the experience that changed your outlook on leadership?
•    Change agent experience: Can you tell me about a time you drove significant changes in an area outside of your direct responsibilities?
•    Ability to be an empathetic driver: Can you recall a situation when one or more of your teammates faced personal obstacles? How did you help the person, and what steps did you take to guide the rest of the team in meeting objectives during this period?

The goal of each open-ended question is to showcase the candidate’s thinking on the fly and elicit an end-to-end story from them. The level of detail they cover in their answers can itself be informative. And while these questions intentionally focus on people and leadership skills, the hope is that the candidate will provide some details on practices and technology in the process,  without devolving into technobabble.

I’ve deliberately ranked these questions in order of difficulty. Most leaders will be able answer questions about their personal learning objectives, but it may require more experience to answer questions about being a change agent or an empathetic driver.

I’ve also collaborated with several other CIOs to identify even more characteristics of those best equipped to lead digital transformation initiatives. We captured fifty attributes organized into five competency areas. You can weigh in on them here.

Initially, it will take some time to shift gears in order to identify, recruit, and mentor digital trailblazers most effectively. But the returns will be exponential. For CIOs under pressure to accelerate digital transformation efforts, having a leadership team of digital trailblazers is essential to help plan initiatives, manage organizational change, and deliver results.