We asked our technology leadership networks to share with us - and with the rest of you - the job interview questions they use to gauge whether a candidate is likely to be a strong digital transformation leader. Here are the responses we have received. Thank you for your responses!


Gary Scholten round

Gary Scholten
EVP & CIO, Principal Financial Group

Interview question:

  • If a business executive came to you to say that we need to pursue digital transformation by applying blockchain, or some other hyped technology, how would you guide the discussion back to a business strategy discussion?

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Paul Karras, CIO round4

Paul Karras
CIO, Hu-Friedy

Interview questions:

  • Tell me how you have cultivated the mindset in IT and your broader organization in order to deliver the promise of technology in a digital era?

    What I am trying to assess through this question are; understand the corporate mindset they operating in, understand their team strength, how they create space for their constituency to learn, how they teach in the process, how they synthesize technologies to influence and deliver business value, and how they manage their attack vector as they further progress into digital. 

  • How do you influence digital investments that deliver and sustain value?

    What I want to understand are several things. For example, A) are they truly partnering with their business constituency for the necessary investments based on defined return on investment? B) Are they only ‘technology experimenting’ without the efforts informing the business strategy? C) How does ‘innovation’ play into their digital investments, and how does their organization measure relative value? 

Other qualifications, experience or soft skills I am seeking or listening for:

Beyond the functional and operational knowledge of the candidate, what I also look for are leadership traits (balancing for the level I am hiring for, of course). I firmly believe that "Traits" drive "Actions", which in turn drive "Results".  As such, the traits that I view critically important  consist of:

  1. Synthesis: the ability to separate signal from noise; ability to visualize with the mind's eye; how they generate a plan; how they generate insights; how they connect the dots (can they see form and rule in other words patterns and irregularities where others can't?)

  2. Decision Strength: Understand the courage of conviction; clarity of vision; do they make emotional decisions (impulsive) or well thought out ones? Are they capable of making "gut decisions" and if so, how fast can they move? How do they go about self-correcting based on new insights they are presented with along the way? I want to understand how they process information (from structured/deterministic data and information.

  3. Character: This is "sine qua non". Understanding one's intent and integrity is crucial. I also want to understand the person's self-awareness, which is like a tool belt from which hangs humility, empathy, compassion and other essentials that humanize the workplace. 

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Jikin Shah round2

Jikin Shah
SVP, Head of Financial Crime and Compliance Technology, SunTrust Bank

Interview questions:

  • Share your experience helping a company achieve exponential business outcome through digital transformation, what that journey looked like.

    What I am looking for is:

    1. Does the candidate have a vision and aspirations of digital enterprise (external and internal) that aligns with this company?

    2. Does the candidate possesses solid leadership and management skills to influence, execute and realize the intended business outcomes through required business operating model, governance, business and IT capabilities?

    3. Can he or she attract and hire the right talent?

    4. Does the candidate have experience with business/IT cultural transformation?
  • What went well and what didn’t go well?

    This is a follow-up question. I am looking for the qualitative and quantitative aspects of the four skills outlined above.

  • How do you pressure test your digital journey and make it future proof?

    I am looking for an honest answer like, ‘The future is unknown, but here is how agility and flexibility were built in to constantly adjust and refine the journey.’ Other pluses include partnerships with startups, universities and industry.

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"What is your vision of what our company will look like after two to three years of digital transformation?"

-Deepak Seth
IT Strategy & Business Transformation Program Leader

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Dee Cantrell round

Dee Cantrell
CIO, US Retina

Interview questions:

  • Tell me about a time where you were able to transform processes and workflows by leveraging a digital strategy. Share how you did that and what the results were.

  • Tell me about a time where your effort to lead a digital transformation did not achieve the expected results, and share how you handled this.

  • How do you, as a leader, give back to the IT profession and community?

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Deepak Seth round

Deepak Seth
IT Strategy & Business Transformation Program Leader, Xerox

Interview questions:

  • What is your vision of what our company will look like after two to three years of digital transformation?

  • What experiences from your own career, including both successes and failures, will you bring to bear to get us there?

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Jason Imperato round

Jason Imperato
CIO, Nomura

Interview questions:

  • Who owns data at your company?

  • What process did you put in place to ensure data quality issues are addressed at the source?

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Rick Omartian round

Richard Omartian
Former Director, IT Strategic Analytics, RELX Group

Interview questions:

  • How do you know if your team has the necessary business knowledge to drive technology innovation for your company?

  • How will you measure success in delivering technology innovation for the business you support?

Other qualifications, experience or soft skills I am seeking:

  • How well they understand business strategy and how technology drives the success of that strategy.

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Lalit Panda round

Lalit Panda
President, Versento LLC

Interview questions:

  • What business parameters have you improved with digital initiatives?

  • Tell me about the last time you spoke to a senior business executive about value creation with technology. 

Other qualifications, experience or soft skills I am listening for:

  • Persuasiveness, listening skills, experience in the operating side of the business in marketing, operations, etc., change management experience, optimism, conviction, familiarity with other cultures, etc.

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Roles That Heller Search Recruits

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Eduard de Vries round
Eduard de Vries
Senior Advisor, Digital Transformation

Interview questions:

  • Where would you focus first if you were starting a digital transformation journey at our company?

    See if the candidate focuses on revenue growth or cost reductions. If cost reductions, he or she might be tactical, and not well-suited for true digital transformation role. 

  • What have you seen as the biggest obstacle for digital transformation?”

    If the answer centers around culture, organizational silos (and how to use cross-functional collaboration to overcome them) or customer experience, then this is a positive. If the answer focusses on technology, or needing to own the transformation, this is a red flag.

 Other qualifications, experience or soft skills I am seeking or listening for:

  • Whether the candidate ever owned a P&L.

  • What is their business growth experience? 

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David Szweda round
David Szweda
VP, Digital Business, Evoqua Water Technologies

Interview question:

  • What is the most critical technology today?

    What I am looking for is more of a technology category, than a detailed specific item. It could be something like Machine Learning, Edge Computing/Analytics. It could also be DevOps. I want to understand how current there thinking is, how well they can articulate the benefits, and if they understand how to tie it to business value. There is no right or wrong answer. I want to understand how their thought process is structured. If they focus too much on the technology benefit without focusing on the business value, then I know I have the wrong person. If they mention a technology that is two to three years old, then I know they are not current.

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Martin Davis round

Martin Davis
Managing Partner, DUNELM Associates
Board Member, TechImpact

Interview questions:

  • How would you describe digital to a business executive?

    If they cannot describe what it means concisely, then how can they lead it?

  • How would you describe the value of Digital?

Other qualifications, experience or soft skills I am listening for:

  • I am on the lookout for general leadership skills, strong change management capabilities, the ability to understand the customer, and the ability to think like a business person. 

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Michael Long round
Michael Long
CIO, MTL Group

Interview questions:

  • What are the barriers that usually block the path to Digital Transformation?

  • What is the culture needed for Digital Transformation? 

Other qualifications, experience or soft skills I am seeking:

  • Whether the candidate sees the difference between 'transforming to digital' and 'transforming digitally'.


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