In an era where digital transformation defines success, the Chief Operating Officer (COO) has become one of the most pivotal roles on the executive team. No longer just the guardian of processes and performance, today’s COO must be a digital strategist, cultural architect, and change leader, capable of turning vision into measurable progress.

At Wyman Bain, we work closely with boards and CEOs across the UK and Europe to identify operational leaders who can thrive in this new landscape. Our experience shows that appointing the right COO is often the turning point between incremental improvement and transformational growth.

So, what should boards be asking when hiring a COO for the digital age? Below, we outline the critical questions that separate the capable from the exceptional. 👇

🚀 1. How do you define operational excellence in a digital-first world?

In the past, operational excellence was about consistency, cost efficiency, and scale. Today, it also means agility, innovation, and digital integration.

Boards should ask:

• How do you use technology to streamline operations?
• How do you ensure digital tools enhance, rather than complicate, performance?
• How do you balance automation with human expertise?

At Wyman Bain, we find that standout COOs see technology not as a project, but as an enabler — a means to improve customer experience, enhance decision-making, and future-proof the organisation.

🧭 2. How have you led digital transformation initiatives?

A modern COO must be a catalyst for digital evolution, not simply a participant in it. Boards should probe for real-world examples where candidates have driven meaningful change:

• Introducing AI or analytics to improve operations
• Overhauling legacy systems
• Creating agile operating models
• Partnering with technology leaders to reimagine customer delivery

Digital leadership requires both technical understanding and cultural sensitivity. At Wyman Bain, we assess candidates for their ability to bring people along the journey, because even the most advanced transformation will fail without human alignment.

👥 3. How do you align technology, people, and culture?

The best COOs understand that digital transformation succeeds when people believe in it.

Boards should ask:

• How do you foster a culture of digital curiosity?
• How do you build trust during times of disruption?
• How do you upskill teams to embrace new technologies confidently?

In our advisory work, we’ve seen that digital-era COOs act as bridge-builders, translating strategy into culture, and innovation into daily practice. They ensure that technology empowers, not alienates, their people.

📊 4. How do you use data to drive better decision-making?

Data has become the new operational backbone. The modern COO must be fluent in using it to guide strategy, efficiency, and foresight.

Boards should explore how candidates:

• Leverage analytics for performance improvement
• Use real-time insights to make proactive decisions
• Balance intuition with evidence

At Wyman Bain, we help boards identify data-literate leaders who can interpret complexity and act with confidence. The right COO will use data not just to report outcomes, but to anticipate opportunities.

🌍 5. How do you integrate sustainability and resilience into operations?

Sustainability is no longer a side agenda, it’s central to operational excellence.

Boards should ask:

• How do you balance digital innovation with environmental responsibility?
• How do you build resilience into supply chains and systems?
• How do you align ESG principles with commercial priorities?

Wyman Bain’s work in sustainability-first leadership shows that the next generation of COOs will need to embed responsible growth at the heart of operations. The digital COO must therefore think not only in terms of efficiency, but impact, for people, planet, and profit.

🤝 6. How do you collaborate with the CEO and C-Suite?

In the digital age, the COO’s partnership with the CEO, CIO, CFO, and Chief Digital Officer is crucial. Boards should ask:

• How do you translate strategy into execution?
• How do you maintain alignment across the executive team?
• How do you handle competing priorities and pace?

At Wyman Bain, we believe that great COOs are connectors, individuals who align vision, strategy, and operations seamlessly. They bridge ambition and delivery, ensuring the business moves as one.

🧠 7. How do you future-proof operations for continuous change?

Digital progress never stands still. Boards should seek COOs who thrive in uncertainty,  those who can pivot quickly, learn continuously, and inspire confidence during transition.

Questions might include:

• How do you stay ahead of emerging technologies?
• How do you prepare your teams for constant evolution?
• How do you measure success beyond short-term KPIs?

The most effective digital COOs are not just operational leaders — they are strategic futurists, anticipating what’s next while keeping the organisation grounded and focused.

🌟 Final Thoughts

The COO for the digital age is a rare and valuable leader,  part innovator, part integrator, and part strategist. They blend digital fluency with emotional intelligence, ensuring that transformation is both technically sound and humanly sustainable.

At Wyman Bain, we help boards identify and appoint COOs who can lead confidently in this era of disruption. Through our executive search and leadership advisory expertise, we match organisations with leaders who deliver digital performance, operational excellence, and long-term resilience.

📞 Get in touch with us today to learn how Wyman Bain can help your organisation find its next COO, one who can align technology, people, and purpose to shape a stronger, more sustainable future.