Why Every Board Needs a Digitally Savvy Director — Bob Howland
Future-ready boards outperform. Here’s what that means.
The pace of technology change isn’t just accelerating — it’s reshaping the fundamentals of how companies compete, grow, and survive. And yet, too many boards are still built to protect the company of today, rather than guide the organization of tomorrow.
If that sounds bold, consider the data. Research from MIT’s Center for Information Systems Research (CISR) found that companies with digitally savvy boards significantly outperform their peers in terms of growth, valuation, and return on assets. The delta is real — and growing.
But let’s go beyond the buzzwords. What does “digitally savvy” really mean?
It’s Not About Coding
Being digitally savvy doesn’t mean you need to understand how to build a data lake or write a line of code. It means understanding how digital capabilities reshape customer expectations, enable new business models, and increase operational agility.
Boards routinely weigh in on decisions that are increasingly dependent on technology:
- Should we acquire this company?
- How do we mitigate cybersecurity risks?
- Are we investing in the right customer experience platforms?
- Should we sunset legacy infrastructure that’s holding us back?
These aren’t just IT questions. They’re strategic questions — and boards need to be equipped to engage in them thoughtfully, not just delegate them.
The Digital Knowledge Gap Is Real — and Fixable
In my work leading transformation across industries — from building Vanguard’s first transaction-enabled website to launching 27 eCommerce businesses and reimagining Dawn Foods’ digital backbone — I’ve seen firsthand how organizations thrive when digital literacy is a boardroom competency, not just an operational one.
But today, most boards still lack meaningful digital fluency. That doesn’t have to be the case.
To close that gap, boards can:
- Recruit directors with transformation experience, not just tech titles
- Invest in ongoing digital education and strategic tech briefings
- Create board-level committees focused on innovation, not just audit and compliance
- Encourage management to bring forward possibility thinking, not just risk reports
What Technology Executives Bring to Governance
Technology executives — especially those who’ve sat in P&L roles — bring more than systems knowledge. They bring a future-focused lens to governance. They ask the “what if” questions. They know how to challenge legacy thinking constructively, not disruptively. And they understand that transformation isn’t a one-time project — it’s a cultural capability.
The best of them also know where to draw the line between strategy and execution. A board’s role is oversight and guidance — not management. But directors who’ve led transformation can spot patterns early, surface blind spots, and make sure management isn’t just delivering on today’s KPIs, but preparing for what’s next.
What I’ve Learned from the Front Lines
Having led technology-driven transformation across finance, manufacturing, retail, and PE-backed ventures, I’ve seen patterns emerge that apply directly to board governance:
- M&A decisions must consider tech stack integration, data architecture, and customer migration — not just financials.
- Risk oversight must include cybersecurity, cloud exposure, and third-party software vulnerabilities.
- Customer experience is no longer a marketing function — it’s a full-stack, end-to-end responsibility.
Questions Every Board Should Be Asking
If you’re a director or a board chair, here are questions worth asking at your next strategy meeting:
- How digitally fluent is our board, really?
- Do we have visibility into our true technology debt?
- Are we empowering leaders to think boldly about innovation — or just protect the status quo?
- Are we designing for tomorrow’s customers, or optimizing for yesterday’s?
Because the truth is, future-ready boards don’t just evaluate performance. They expand possibility.
And in today’s world, possibility is a strategic advantage.
