Your Board Wants AI Results in 2027. Can Your IT Organization Deliver Them?

Every board meeting I sit in this fall has the same moment. Someone asks, "What's our AI plan for next year, and what will it return?" The CEO looks at IT, and IT gives an answer built on hope.

The pressure is real. A survey cited by CIO.com this week found that 98% of CIOs report more board pressure since 2024 to show measurable AI results. The same piece lists 13 questions shaping 2027 IT agendas, and almost all of them depend on one unasked question: is our IT organization able to deliver real value to the business?

My advice to CEOs this November is simple: check the foundation before you promise the house.

The Question Behind the 13 Questions

Most of the 2027 agenda is about AI. The last item matters most: how should IT be organized to deliver more business value?

You can't answer that from a budget spreadsheet. You need to know:

• •Whether your IT team is working on the right things or just the loudest things
• •Whether your core systems, especially ERP, can support what you want AI to do
• •Whether the data your leaders use to make decisions can be trusted
• •Whether your projects finish on time, or just get reported as "green" until they don't

Three Things the Board Usually Can't See

In assessments I've led, the real risks tend to sit in three places:

• •Bad data driving real decisions. A OneStream survey found 47% of finance and IT leaders made a material decision on inaccurate or outdated data in the past year. AI makes that problem faster, not better. (More in Why Your Data Is Lying to You.)
• •Projects with no single owner. Lots of activity, no accountable leader.
• •Key-person risk. One or two people hold the systems and vendor relationships together. If they leave, the 2027 plan leaves with them.

Judge IT by Business Results, Not IT Activity

This is where most IT plans fall short. Busy is not the same as valuable. Every project, system and dollar in your 2027 IT plan should pass three tests:

• •Is it aligned with the business strategy? If you can't draw a straight line from the work to a goal in your business plan, such as growth, margin, customer experience or speed, it's a candidate to stop.
• •Does it differentiate the business? Keeping the lights on is necessary, but it doesn't win customers. The investments that matter most let you serve customers better, move faster or operate at a lower cost than your competitors.
• •Can we measure it? Define the result up front in business terms: revenue, cost per order, days to close the books, customer retention, hours given back to the team. Set a baseline, a target and a date, then report against it.

A good health check scores your current IT portfolio against these three tests. The work that fails them becomes your funding source for the work that actually moves the business. (I've written more about this in Making IT a Business Differentiator.)

What a CEO-Level IT Health Check Looks At

A real health check isn't a network scan or a vendor's "free assessment." It looks at IT the way a CEO would:

• •Strategy and alignment: Does the IT plan support the business strategy, or just repeat last year's spending?
• •Value and measurement: Are results defined and tracked in business terms?
• •Applications and ERP: Can your systems support your growth and AI plans?
• •Data and AI readiness: Is there a foundation worth building AI on?
• •Projects and delivery: What's on track, what's at risk and what should stop?
• •People, vendors and risk: Do you have the right skills, leadership and partners, and what happens if a key system or person is unavailable for a week?

What You Should Walk Away With

The output should fit on a CEO's desk, not a shelf:

• •A short decision memo: what's working, what's at risk and what needs a decision now
• •A clear view of which investments differentiate the business, with the measures to prove it
• •A prioritized roadmap with realistic cost ranges
• •An honest answer on whether you need more leadership, such as a fractional or interim CIO, or simply better execution

What to Do Next: A Year-End Checklist

• ☐Ask your IT lead for a one-page list of every active project, its owner and its real status.
• ☐For each major 2027 IT investment, write down the business goal it supports and the number that will prove it worked.
• ☐Ask which of those investments makes you different from your competitors.
• ☐Name the two or three people your systems can't run without.
• ☐Ask finance where they don't trust the numbers, and why.
• ☐Schedule an independent IT health check to finish before Q1 budgets lock.

Frequently Asked Questions

Related Reading