Why this matters:

Chief digital officers can work in many industries, each with a different set of needs and technologies. Ideal candidates should have an adequate understanding of your organization’s market and customer base, plus your industry’s specific technologies and processes. They should also have experience in helping companies solve challenges similar to those of your organization.

What to listen for:

• Track record of success with similar organizations
• Knowledge of key industry trends, terms, and processes
• An excellent understanding of your market and customer base

Why this matters:

Chief digital officers should have a broad knowledge of the current trends and opportunities in the market and have the ability to position your organization’s performance and capabilities in line with them. In addition, they should aim to find new business opportunities either through applying your organization’s existing technologies or with the integration of new ones.

What to listen for:

• Up-to-date knowledge of emerging technologies
• Ability to effectively articulate the ROI and benefits of new technologies or processes
• Ability to think creatively and strategically

Why this matters:

By definition, chief digital officers are driven to harness the strengths of a digital environment, one system at a time. But what’s their process for doing so? A strong answer to this question will mention how the candidate identifies and defines clear and measurable goals, prioritizes them, then gains the funding, buy-in, and resources necessary — whether cross-functional or from outside the organization.

What to listen for:

• Ability to set clear, actionable goals for themself and for others
• A practical, results-driven approach to lasting, sustainable change
• The ability to generate both short-term and long-term results

Why this matters:

Successful chief digital officers must persuade stakeholders, including those with little technical knowledge, to adopt new technologies or approaches. Tactics may include persuasion — whether with data or anecdotal evidence — and the ability to lobby fellow leaders and others to build coalitions in their favor. This question examines their methods.

What to listen for:

• The ability to change approaches, depending on the audience
• The building blocks of persuasion: logic, reasoning, data, stories
• A track record of success

Why this matters:

Successful candidates should have experience in analyzing systems and operating processes, recognizing areas for improvement, and using their findings to recommend and implement appropriate solutions in line with organizational goals and customer needs. This requires a combination of technical and analytical skills, along with leadership skills to effect organizational change.

What to listen for:

• A track record of success identifying problems and implementing solutions for them
• Experience integrating digital strategies into all aspects of an organization
• Ability to identify new opportunities and optimize organizational processes

What to listen for:

• An analytical and process-driven approach to problem-solving
• An innovative mindset with the ability to think strategically
• Ability to formulate, communicate, and execute actionable strategies

Why this matters:

As leaders who will plan and execute strategies for optimizing or implementing new technologies and processes, chief digital officers can greatly benefit from utilizing the agile approach to innovation. Ideal candidates will have experience in key features of agile project management, such as managing cross-functional teams, working in sprints, and being flexible and open to changes.

What to listen for:

• A collaborative mindset that prioritizes teamwork
• Experience using iterative approaches for problem-solving
• Experience leading cross-functional teams

Why this matters:

A chief digital officer is likely in charge of a department or a cross-functional team. This requires the ability to manage, cultivate, and champion a diverse set of direct reports. It’s important to evaluate the candidate’s management experience, including their ability to lead, persuade, and motivate people, rallying them to collectively hit or exceed goals.

What to listen for:

• Leadership skills
• The ability to inspire and motivate others
• Empathy and caring

Why this matters:

It’s important for all C-suite executives to have a vision — whether polished and detailed or simply ideological. This question explores the candidate’s vision for the role, allowing them to demonstrate their consideration of your company and its industry context, marketplace opportunities, and other relevant factors.

What to listen for:

• A clear philosophy and viewpoint
• An indication of how the candidate might define success — and whether it aligns with your culture, strategies, and leadership
• The desire to drive change and make a lasting impact