The 45-Minute Tech Spend Checkup Every CEO Should Run

Technology spending problems rarely start with the software. They start with drift.

A tool gets bought to solve a problem. The problem changes, the person who championed it leaves, and the renewal goes through on autopilot. Multiply that by a few dozen subscriptions and a couple of years, and you have a technology budget nobody can fully explain.

The usual response is an audit: spreadsheets, invoices, a consultant, six weeks. Sometimes that's the right call. But most of the time you can learn what you need to know far faster, with a conversation.

Here's the one I recommend. It takes 45 minutes and your leadership team. No spreadsheets required.

Before the meeting (10 minutes, one person)

Ask whoever handles finance or IT to bring one page:

• The top ten technology costs by annual spend, including software, cloud, support contracts and outsourced services
• The renewal date for each
• Who owns each one internally, if anyone

That's it. Don't let it grow into a project. If producing that page is hard, you've already learned something important.

The agenda

1. What outcomes are we actually buying? (10 minutes)

Go down the list. For each item, ask what it does for the business. Not features or licenses, but outcomes: speed, margin, capacity, reliability, reduced risk.

A good answer: "It cut quote turnaround from two days to two hours."

A warning sign: "Everyone uses it." "We've always had it." "It's the industry standard."

If nobody around the table can name the outcome, the spend isn't strategic. It's habit.

2. Where do tools overlap? (8 minutes)

Look for two or more systems doing the same job: three ways to share files, two project trackers, a CRM in sales and a different one in customer service. AI has made this worse, as new assistants now arrive bundled into tools you already pay for and as separate subscriptions people sign up for themselves.

Overlap isn't innovation. It's drift, and you pay for it twice: once in licenses and again in the time people waste working out which system holds the truth.

3. What's under-used? (8 minutes)

For each major tool, roughly how many of the people you're paying for actually use it?

As a rule of thumb, if fewer than a third of the seats are active, you aren't getting value. You're paying rent on shelfware. Most vendors can show you usage data if you ask; many hope you won't.

4. What's brittle? (10 minutes)

This is the question that turns a cost conversation into a risk conversation. Where does everything depend on one thing?

• One system that, if it went down for a day, would stop the business
• One vendor you couldn't leave even if you wanted to
• One person who is the only one who knows how something works

Brittle spending isn't always too much spending. Sometimes the answer here is to spend more on something cheap and fragile before it fails at the worst possible moment.

5. What wouldn't we buy again today? (5 minutes)

Ask everyone at the table: knowing what we know now, which of these would we not sign up for if we were starting fresh?

It's the most honest question on the list, and often the most productive. Clarity comes from subtraction as much as addition.

Decide (4 minutes)

Don't leave with a list of ideas. Leave with one decision:

• Consolidate two tools into one
• Simplify by cutting seats, dropping a tier or removing features nobody uses
• Stop funding something that no longer earns its place

Give it an owner and a date, ideally before the next renewal on your list. Then reinvest what you save in something that's working.

What this isn't

It isn't a cost-cutting exercise. Some of the best outcomes I've seen from this meeting involved spending more, on the thing that was brittle or on the tool that people loved but nobody had properly rolled out.

It's about making sure technology speeds the business up instead of distracting it. A good technology strategy is measured in confidence, not complexity.

Make it a habit

Run it again in 90 days. The second meeting is faster, because the list is shorter and everyone knows the questions. After a few rounds, you'll notice the conversation changes: people start asking "what outcome are we buying?" before they sign up for something.

That's when you know it's working.

Want it on one page? Download the free checklist - the agenda, the five questions and a box for your one decision, ready to print and bring to the meeting.

Related reading

• The "Later" Tax: What Deferred Technology Decisions Really Cost
• Status Maintains Motion. Decisions Create Momentum.

If this meeting raises more questions than it answers, or nobody could produce that one-page list, let's talk. Bringing order to technology spending is a big part of what I do.