Most managing partners have a sense that something is off with technology. Costs feel high. Systems feel fragile. Client questionnaires create anxiety every time they arrive. But when it comes time to ask questions in a board meeting, the conversation usually goes sideways.

I've sat in those meetings. For over 13 years inside Top 10 professional services firms, I watched partners ask technology questions that sounded reasonable but completely missed the point. The result? Decisions based on incomplete information, budgets that don't reflect reality, and a growing gap between what the firm needs and what it's actually getting from its technology investment.

Here are five questions that will change the conversation.

1. "What is our technology actually doing for staff efficiency — and can we measure it?"

This is the question almost nobody asks. What I hear instead is "what can we cut this year?" Partners default to looking at technology as a cost line to be minimized, not an investment that should be producing measurable efficiency gains.

The right question isn't whether you can cut $50,000 from the IT budget. The right question is whether your technology is enabling each professional to handle more clients, produce work faster, and spend less time on administrative tasks. If you can't answer that with data, you're managing technology by gut feel — and you're probably making bad decisions in both directions.

A firm I worked with had partners pushing hard to cut technology spend because "everything is working fine." The IT team proposed a $50,000 infrastructure investment that would modernize remote access capabilities. Partners said no — why spend money when nothing is broken? Then COVID hit. The firm's infrastructure couldn't handle the entire workforce going remote. They ended up spending that $50,000 anyway, but under emergency conditions with no time to plan.

The cost of waiting was significantly higher than the cost of acting.

The question isn't "what can we cut?" It's "what is this investment producing — and what are we leaving on the table?"

2. "How does our technology spend compare to firms our size — and what does that actually mean?"

Partners love benchmarking. I'd regularly hear "our IT costs are X percent of revenue" followed by "I heard Firm Y is at 5%" or "someone told me the industry average is 4%." The numbers would range wildly — from 4% to 10% — and nobody could explain what drove the difference.

Here's the problem: the percentage alone tells you almost nothing. A firm spending 4% of revenue on technology might be underinvesting and accumulating technical debt that will cost them later. A firm at 8% might be investing aggressively in tools that are producing measurable efficiency gains. Without understanding what's in that number — and what your firm is getting for it — you're comparing apples to the idea of fruit.

Most managing partners don't want to be on the high end and don't want to be on the low end. They want to be in the middle. But "middle" without context is meaningless. What you should be asking is: what is our cost per user, what are we getting for that cost, and where are the gaps between what we're spending and what comparable firms are achieving with similar investment levels?

3. "Who is actually managing our software licenses — and do we know what we're paying for?"

This one sounds simple. It is not.

In nearly every firm I've worked with, license management is chaos. Here's what actually happens: a tax partner at a satellite office decides the team needs a new piece of software. They buy it on their credit card and expense it. Accounts payable sees "software" on the receipt and files it under the IT budget. IT doesn't know about it. Meanwhile, the firm may already own a tool that does the same thing — the partner just didn't know it existed.

Multiply this across offices and departments and it gets expensive fast. People buy individual ChatGPT subscriptions and expense them. They sign up for Dropbox accounts for a project and expense them. Each one is $20 here, $30 there — but across a 200-person firm, these "shadow IT" expenses add up to real money. And every one of them ends up on the IT budget, inflating the number that partners then complain about.

The real problem isn't the individual purchases. It's the lack of a purchasing approval workflow. Every technology purchase should be approved before it's made. That single process change can save tens of thousands of dollars annually and give the firm accurate visibility into what it's actually spending.

This gets even worse after mergers and acquisitions. Firms that have grown through acquisition end up with three different document management systems, two practice management platforms, and overlapping security tools — because nobody followed through on consolidation. The duplicate spend compounds year after year, and nobody puts their foot down to say "we're all moving to one platform" because it's uncomfortable.

4. "If a client asked us today about our security posture, could we answer confidently?"

For most firms, the honest answer is no.

Partners are almost universally blind to security. They understand phishing emails exist. They know ransomware is bad. But they're so focused on serving clients and running the practice that security is an afterthought — until something forces it to the front of the conversation.

That "something" is usually one of three triggers: an actual incident (which one of my firms experienced, and I can tell you the partners' attitude shifted overnight from "why are we spending on this" to "this can never happen again"), a client security questionnaire that exposes gaps, or a cyber insurance renewal where the firm can't confidently make the required attestations.

The worst time to think about security is when one of those triggers hits. By then, you're reactive, making decisions under pressure, and paying a premium to fix things that could have been addressed proactively. If your partners can't articulate your firm's security posture in a client meeting without calling someone in IT, that's a gap that needs to close.

5. "What happens to our technology if we acquire a firm — or get acquired — in the next 18 months?"

This is the question that separates firms that are thinking strategically from firms that are reacting. If your firm has any growth ambitions — and especially if M&A is part of the strategy — your technology environment needs to be ready to absorb or be absorbed.

Most firms don't bring technology into the deal conversation until after the LOI is signed. By then, it's too late to influence deal terms, too late to properly evaluate what you're inheriting, and too late to plan an integration that doesn't disrupt client work.

The firms that handle this well have clean documentation of every technology contract and its expiration date. They know their cost per user. They have organized budgets where expenses are properly categorized. They have a technology purchasing approval process. In short, their technology environment is "staged" — ready for a buyer or a deal team to evaluate quickly and cleanly.

The firms that don't? They end up in post-close chaos, discovering ancient servers, inheriting terrible vendor contracts, and spending the first 90 days of an integration just trying to figure out what they bought.

The Common Thread

Every one of these questions comes down to the same thing: visibility. Most firms don't have an independent, objective view of their technology environment. They don't know how they compare to peers. They can't articulate what their technology spend is producing. And they're making partner-level decisions about technology investment based on anecdotes and gut feel instead of data.

That's fixable. It starts with asking better questions.