I recently had a conversation with a group of IT leaders. We were talking about what good looks like, and I posed a simple question: "How do you know if you're succeeding?"
The room went quiet. I could see the wheels turning in their heads. They started talking about keeping the lights on, meeting deadlines, and managing budgets. All important things, but none of them could articulate what success really meant for their teams beyond basic operational metrics.
Later, I asked a similar question to a few executives who aren't in IT but have IT reporting to them. The response was the same—a lot of thoughtful silence and then a scramble to find an answer. It got me thinking: If the people running IT and the people who depend on IT can't agree on what success looks like, how can we possibly know if we're on the right track?
Why This Matters More Than Ever
In today's world, technology isn't just a support function; it’s the engine of the business. You can’t operate without it, and in many cases, you can't get ahead without it. But if we can't define what a "well-oiled engine" looks like, how can we expect it to drive us forward?
So, where do you even begin? We need to get a clear picture of the fundamentals of IT performance. It’s about understanding how technology and information add real, tangible value to the business. Once you get that right, you can start to think about how IT can truly set you apart from your competition.
Five Questions to Ask (and Answer)
Sometimes, the best way to get a handle on things is to ask some direct, honest questions. So, here are five questions that every executive should ask their IT leader, and that every IT leader should be able to answer with confidence. Think of it as a starting point for a conversation, not a final exam.
- How reliable are our systems?
This is the foundation. If your systems are constantly breaking, everything else falls apart. You can't talk about innovation or growth if you're always putting out fires. A good way to measure this is by tracking the number of faults or outages. Are they going up or down? Are you spending all your time fixing things, or are you free to build new ones? - Do we get a satisfactory level of service from our IT providers?
IT is a team sport, and it’s likely you're working with an internal IT team and a bunch of different partners and vendors. The question is, are they working for you or are you working for them? This can be measured by looking at how long it takes to fix issues and respond to requests. Are your partners holding up their end of the bargain? - Are we successfully delivering IT-enabled projects?
Here's where the rubber meets the road. Are your projects finishing on time, on budget, and to the right quality? You might have heard of the "project management triangle" of time, cost, and quality. It's a classic for a reason. Are your IT projects hitting the mark? - Are we achieving the planned benefits from our projects?
This one is often overlooked but it's the most important. You invest in a new system because you expect a certain outcome—better efficiency, more sales, happier customers. Did you actually get it? You should have quantified these business outcomes before you even started the project, and you should be measuring them to know if the investment was truly worthwhile. Otherwise, what was the point? - Are we spending about the right amount on IT?
This can be a tricky one, and there's no single magic number. If you spend too little, you're probably missing opportunities and putting your business at risk. If you spend too much, it's a drain on the bottom line. You can look at industry benchmarks to get a sense of where you stand, but the most important thing is reflection. Constantly ask yourself: Is the value we're getting from IT in line with what we're spending?
Now What?
If you're a non-IT executive with a seat at the table, start asking these questions. Don't just ask for a verbal answer; ask for the data. Data doesn't lie, and it will give you a clear picture of what's really happening.
And if you're an IT leader, start gathering this data and sharing it with your manager. Use it as a conversation starter to discuss how you can improve and where you need support. By doing this, you're not just reporting numbers; you're building trust and showing that you're a true partner in the business.
This isn't about pointing fingers. It's about changing the conversation from one of frustration and uncertainty to one of clarity and purpose. Because when we can all agree on what success looks like, we can finally start working together to achieve it.