Five IT Questions Every Business Leader Should Ask Twice a Year

Ramona
Dec 26, 2025
2 min read

Technology has a funny way of fading into the background when it’s working, and demanding all of your attention when it’s not.

That’s why the smartest businesses pause at least twice a year to ask a few honest questions about their IT. Not to panic. Not to overhaul everything. Just to understand what’s helping, what’s hurting, and what’s quietly slowing things down.

Think of it as a regular check-in for the systems your business relies on every day.

Here are five questions worth asking every six months.

1. What technology is actively helping our business move forward?

Start with the wins.

Which tools make your team faster, more organized, or less stressed? What systems support growth, collaboration, or better customer service?

This might be:

Cloud tools that save time
Hardware that just works
Automation that removes busywork

Identifying what’s working helps you protect it, budget for it, and build on it, instead of accidentally breaking it or replacing it later.

2. What technology is quietly slowing us down?

This is the sneaky one.

Slow logins. Systems that “usually work.” Processes that require workarounds everyone just accepts.

These issues rarely cause emergencies, but they do cost time, energy, and momentum. Over a year, they add up to lost productivity and frustrated staff.

If your team has learned to work around the technology instead of with it, that’s a signal worth listening to.

3. Do we understand our current security risks?

Cybersecurity doesn’t have to be scary, but it does need to be intentional.

Ask yourself:

Do we know where our data lives?
Do we know who has access to what?
Would we notice quickly if something went wrong?

You don’t need perfection. You need awareness. Knowing where you stand is the first step to making smart, calm improvements instead of reactive ones later.