7 Questions Board Members Should Be Asking

Jen L. Cohen
3 min readSep 12, 2022

As we all know, technology has advanced rapidly over the years. At one time, the pictures below were the tippy-top of high tech. And now they’re antiquated building blocks that no one thinks twice about. We’ve greatly advanced our technology, so we must also match this with innovative board diagnostics and assessments.

Over the next 7 weeks in this series, we’ll cover 7 critical questions board members should ask of their company technologists and C-suite. The more information they have on these necessities, the better decisions they can make moving forward.

Let me start by saying that these questions are meant to be canaries in the coal mine, so to speak. They help to indicate overall technical health and to facilitate solutions that can improve technology, alignment, cost, and culture.

In addition, these questions should give you insight into how you can, from the broader board view, widen the aperture of your leaders in this space.

#1: What are the ages and annual costs for our most critical systems?

Why ask?

Over 70% percent of the Fortune 500 are using older systems for their critical and core workloads*. Conversely, the time in which these companies stay on top becomes significantly shorter. When you ask this question and find that your company is using systems from the 80s or even systems from the aughts, it indicates that relevance, competitive advantage, employee experience, and technical (and beyond) talent retention have much room for improvement. To be clear, this doesn’t mean we should rush out and buy the coolest, newest, shiny tech. Instead, it suggests that we need to look at what’s going to make and keep us competitive in the long term.

Follow-up questions for extra credit:

  • What’s the oldest system?
  • How many systems do we still run that have been depreciated?

If we have older systems, especially some so old they’re largely off the books, we need to ask ourselves, why are we not investing in tech because we know every company, at least in part, is a tech company? And how do our aging systems tie back to our business outcomes? What revenue and competitive advantage are we losing on these older systems? If a restaurant has used the same menu for 30 years, are they still in business? Typically not.

I like to think of it like this, if we wouldn’t personally use computers and systems that are 30 years old — why would we run our companies on them?

Interested in reading the full series?
7 Questions Board Members Should Be Asking:

#1: What are the ages and annual costs for our most critical systems?

#2: How much tech debt do we have, and how much is it costing us annually?

#3 What’s the retention rate of our technical personnel?

#4 What does keeping the technical “lights on” cost us annually?

#5 If we invested 100k in “lights on” efficiencies, how much would we free up in dollars and resources?

#6 What is our “unfair data advantage?”

#7 What is one technology investment that could make the biggest difference to revenue?

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Jen L. Cohen

Mentoring women in tech | CEO of Lights On Advantage | Fractional CTO 100% Capacity| former CIO | Board member