The Five Questions Every Board Member Should Ask About Technology (But Most Don't)
A practical framework for non-technical executives to provide meaningful technology oversight in an AI-driven world.
Technology can be intimidating. Your iPhone is thousands of times more powerful than the computer you used in high school or university. Your company likely has dozens, if not hundreds, of applications and databases seemingly running your business magically. The world has changed rapidly, and it’s increasingly complex.
Late last year, AI became one of the number one topics in corporate earnings calls. We hear about it everywhere, every day. AI is important. AI is valuable. It will need your data and your people to harness its power and transform with it. And, while AI is set to make a wave of transformations, ERP systems, SaaS systems, even mainframes will exist in company of the future – many of these systems forming the base of the data you need to train future agents..
In your role as a director, you know you don’t need to be a technologist, but in todays world, you do need to ask the right questions and know which answers should concern you. These five essential questions can cut through the tech jargon and get to business.
THE FIVE QUESTIONS
Our body of knowledge is grounded on basic principles that have proven effective across industries and organizational scales:
1
"How Critical is Technology to Our Business Operations—and How Would We Know?"
2
"Do We Have the Right Technology Talent—and How Do We Know We're Not Losing Them?"
3
"Are We Spending the Right Amount on Technology—and Are We Getting Value?"
4
"What Technology Policies Govern Our Biggest Risks—and Are They Actually Working?"
5
"How is Technology Enabling Our Strategy—and What Would We Need to Change It?"
QUESTION #1
"How Critical is Technology to Our Business Operations—and How Would We Know?"
Most board members understand technology is “important” for their business but cannot clearly explain how critical it is or how vulnerable the company may be. Using some simple questions you can quickly come to terms with just how critical it is and what it might cost you if you have a big failure or breach.
How do you explore this effectively?
- What are our critical systems? And what makes them so?
- What happens if one goes down for an hour, day, or week?
- Is there a set maximum downtime for each?
- Are there single points of failure supporting them?
- What percent of revenue (or expense) flows through each one?
- Does the company have manual workarounds defined in the event of failure?
What to watch for: Management can’t explain what’s critical. No evidence of recovery tests, impact assessments or work arounds. Not all technology is created equal. Some systems are nice to have. Others are your business. Good management knows what they can live without and plans for the ones they can’t.
A good answer: “Here’s our business criticality matrix. I can show you which systems directly generate revenue, which support operations, and our disaster recovery priorities. We test our backup plans quarterly, and our last test took 4 hours to restore critical systems.”
QUESTION #2
"Do We Have the Right Technology Talent—and How Do We Know We're Not Losing Them?"
This question is at the core of why Technology Done Well was created. Building top talent both in technology management and employees to grow Canada’s companies. Many employers face technology talent shortages and the war for talent rarely ceases – even in slack general labour markets. Making matters more challenging, technologists often gravitate to strong architectures and projects and perhaps not enough time on deep and strong talent benches. The best technology professionals are rarely looking for jobs—they’re happily employed, found through referrals rather than job postings, and often unimpressed by outreach. How can you hone in on what is critical, perhaps missing and what your position in the market is?
Consider approaching this question from multiple angles:
- Do we have a skills inventory? Are critical capabilities missing? If Cyber Security, AI/ML, Cloud, or Data aren’t listed, explore further.
- What are our turnover rates in technology roles (how many people are leaving)? What do exit interviews tell us about this group?
- How does our compensation compare to market? (of technologists)
- Who backs up the head of technology? How deep is our leadership bench?
What to watch for: No skill gaps mentioned & hot skills potentially overlooked, no training program, leaders lack bench depth, no tech-specific compensation benchmarking.
A good answer: “We track our technology turnover monthly—it’s currently 12% annually, below our industry benchmark of 15%. We have documented succession plans for all senior technology roles, and each plan includes at least one internal candidate who’s ready now and one we’re developing for 18-24 months out.”
QUESTION #3
"Are We Spending the Right Amount on Technology—and Are We Getting Value?"
Many organizations struggle with technology spending—sometimes high and wasteful, but also lean and limiting. Getting it right takes time, judgment and relentless rigour.
Obtain a rounded view as much as possible on the spend:
- What’s total tech spend as percent of revenue or operating expense? How does it compare to peers?
- What’s spend per employee (or user) year over year?
- Where’s money spent? Running, improving, or transforming the business? Cloud vs on-premise? Capital vs operating? Staff vs consulting?
- Are we getting value from projects? What’s our success and return rate on technology projects?
What to watch for: Limited benchmark data, no understanding of spend categories, and limited or vague project data.
A good answer: “We spend 4.2% of revenue on technology, which aligns with our industry benchmark. 60% goes to maintaining existing systems, 40% to new capabilities. Our three largest investments this year are [specific projects], which directly support our priorities of [specific goals]. We review this quarterly with finance.”
QUESTION #4
"What Technology Policies Govern Our Biggest Risks—and Are They Actually Working?"
Risk is everywhere in business. Competition, politics, operations, people, etc. You likely understand your top enterprise risks, but is technology on the list? Here’s an uncomfortable truth: most organizations have more technology policies than they can actually enforce.
Some key areas to consider:
- Does management have an AI use policy? How is it overseen?
- Does Cyber governance exist? Does it follow industry frameworks?
- Is your data classified and does management know where it resides? Does the company comply with required regulations?
- How does technology fit in Enterprise Risk Management?
- What policies govern the use of the company’s systems and data – and how are they applied?
What to watch for: No cyber oversight, no incident response plan (everyone needs one of these!), and no clear answers on critical data identification or protection.
A good answer: “Technology is #3 on our risk register, and we review quarterly.. We follow the NIST Cybersecurity Framework, test our response plan twice yearly, and track compliance across policies—last quarter showed 94% compliance with documented plans to address the gaps. Our AI committee has evaluated 8 tools this year with clear approval criteria, we completed our data classification inventory last year and and we can show you exactly where our restricted data resides and how it’s protected.”
QUESTION #5
"How is Technology Enabling Our Strategy—and What Would We Need to Change It?"
Ensuring technology aligns with business is difficult to assess. It takes absolute clarity not only in your strategy – but the specifics of its implementation. Many CEOs cite technology as a primary enabler, saying Digitization or AI is a game changer—but few test these statements. The devil is ALWAYs in the details and understanding exactly what business outcomes a technology program or project will deliver is critical.
Questions to ask:
- How does your technology plan support business strategy?
- Is there a multi-year plan for system investments and upgrades that are aligned with business priorities?
- What are your legacy systems? Is there a migration plan?
- Is there a structured technology innovation process?
- How do we compare to competitors?
What to watch for: Jargon-heavy responses, everything is ‘strategic,’ no documented plans, lack of a process or ability to drive change.
A good answer: Our three-year plan maps every major investment to specific business outcomes—like our CRM modernization launching in Q2 will reduce customer onboarding from 14 days to 3 days. We’ve documented all 6 legacy systems with migration timelines. We run a structured innovation process where business units propose initiatives, IT scores them on impact and feasibility, and we’ve funded 4 of 12 this year—each with a business unit accountable for measurable ROI.
BRINGING IT ALL TOGETHER
So how do we measure how the technology is functioning for our company? There is no perfect scorecard and most boards receive too much detail or too little. Here’s the basics of what we believe you should see quarterly:
The One-Page Technology Dashboard
1. CRITICALITY & RESILIENCE
- Uptime for critical systems
- Business continuity test results
- Open high-severity incidents
2. TALENT HEALTH
- Headcount vs plan
- Attrition rate
- Critical skill gaps
3. FINANCIAL PERFORMANCE
- Tech spend as % of revenue
- Run/Grow/Transform breakdown
- Top 3 investments
4. RISK & COMPLIANCE
- Cybersecurity maturity
- Open vulnerabilities
- Policy compliance
5. STRATEGIC PROGRESS
- Plan status
- Top 3 initiatives
- Innovation pipeline
CONCLUSION
Your Role:
- You don’t need to understand all the details
- You DO need to understand if technology enables or constrains strategy
- You DO need to ask tough questions
Remember: Your job isn’t to manage technology; it’s to ensure technology is managed.
The Bottom Line: In 2026, every has technology and its getting more and more complex daily. They need your EFFECTIVE oversight.
For Board Members:
Invest in your development: “Technology Governance for Non-Technical Directors”
Does your management need coaching or advisory services? Reach out to book a free 30-minute consultation.
About Technology Done Well: We are purpose-driven. Our services are designed to help your company succeed with planning, implementing, and operating technology. Our goal is to foster learning and development to strengthen Canadian businesses’ application of technology and grow the skill base at all levels required to do so.