10 Interview Questions for Digital Trailblazers: Find Amazing Candidates and Land Exciting Jobs

At a recent Coffee with Digital Trailblazers, several of us shared our favorite questions to ask Digital Trailblazers on interviews and how to prepare for them. I captured 20 key questions that job seekers should rehearse before their next interview and that leaders should use to separate the good from amazing candidates.

10 Interview Questions for Digital Trailblazers: Find Amazing Candidates and Land Exciting Jobs

Thank you to Digital Trailblazers Joanne Friedman, John Patrick Luethe, Heather May, and Joe Puglisi for sharing your amazing insights!

Digital Trailblazer Community I’m sharing ten questions here and will provide the other ten to the Digital Trailblazer Community in a follow-up soon. The questions here cover enthusiasm, authenticity, creativity, and curiosity, while the follow-up post contains questions on role transitions, critical thinking, team dynamics, and company fit. I also include recommendations on how leaders can evaluate answers and tips on what details job seekers should include and should not include in their answers.

10 Interview Questions for Digital Trailblazers

Initial Questions:

  1. About You: Based on the role and company structure I’ve described, tell me about yourself and your experience relative to these specifics.
  2. Accomplishments: Can you provide examples of your accomplishments, such as percentage increases, dollars brought in, or numbers added, and explain their significance?
  3. Big Picture: Where do you see yourself fitting into our overall initiative, whether it’s digital transformation, business transformation, or another area?


  1. Fire in the Belly: How do you show enthusiasm and passion for the job and making change happen?
  2. Homework on Company: What have you learned about our company, and how can you contribute?


  1. Developing Relationships: How do you develop relationships quickly with colleagues and stakeholders?
  2. Consistency: How do you ensure consistency between your LinkedIn profile, resume, and interview responses?

Creativity and Curiosity:

  1. Creative Problem-Solving: How do you approach creative problem-solving in your work?
  2. Curiosity: Can you give an example of a time when your curiosity led to a significant positive outcome in your work?
  3. Expertise: What specific expertise do you bring to this role, and how have you demonstrated this in past positions?

Recommendations for Digital Trailblazer job seekers

Pause and think before answering any question. Focus on one or two areas that illustrate your capabilities as a digital transformation leader. Find a mentor or coach to help you prepare for interviews.

Related posts that might interest you:

Sign up for the Digital Trailblazer Community to get early access to the other ten Digital Trailblazer interview questions.

Isaac Sacolick
Join us for a future session of Coffee with Digital Trailblazers, where we discuss topics for aspiring transformation leaders. If you enjoy my thought leadership, please sign up for the Driving Digital Newsletter and read all about my transformation stories in Digital Trailblazer.

Coffee with Digital Trailblazers hosted by Isaac Sacolick Digital Trailblazers! Join us Fridays at 11am ET for a live audio discussion on digital transformation topics:  innovation, product management, agile, DevOps, data governance, and more!

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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.