The Solid Footing Self-Assessment

Eight questions to help you understand where your business actually stands.

No one sets out to build a technology mess. It accumulates. A second employee, a third laptop, a new app, a shared login that nobody got around to changing. Over time, the tools your business runs on look less like a system and more like a collection of decisions made under pressure.

Most small business owners have a general sense that things could be tighter. Very few have ever looked at it all in one place.

The questions below are not a report card. There is no grade at the end. They are the questions we walk through with business owners before we start any work together, because the answers shape everything that comes after.

Take five minutes. Work through them honestly.

Access

Does every person on your team have their own login for every business system?

Shared accounts are one of the most common and most overlooked gaps in small business technology. When two people share a login, there is no way to know who did what, no clean way to remove one person's access without removing both, and no clear line of accountability when something goes wrong.

If someone left your company today, could you remove their access to everything before end of day?

This one tends to stop people. Not because they do not want to answer yes, but because they realize they would have to spend an hour making a list before they could even start. If you would need to track down accounts, call vendors, or guess at what someone had access to, the answer is no.

Is two-step verification turned on for email, file storage, and financial tools?

A stolen or guessed password is enough to get into most business accounts that rely on a password alone. Two-step verification means one compromised password is not enough to get in. It is one of the most effective protections available and costs nothing to turn on.

Data

Is your business data stored somewhere other than individual laptops?

A laptop is a device. Devices fail, get stolen, and eventually get replaced. If the information your business depends on lives primarily on individual machines, it is one hardware failure away from being gone. Cloud-based file storage is not a luxury at this point. It is the baseline.

Do you have a current backup? Have you ever tested whether it actually works?

Most business owners who have a backup set up stopped thinking about it the day they turned it on. A backup that has never been successfully restored is not a backup. It is a hope. Testing a restore, even once a year, is the difference between those two things.

If the most important laptop in your business disappeared tonight, what would tomorrow look like?

Worth sitting with. The answer tells you a lot about how dependent your business is on a single device and whether you would be able to keep working or be starting from scratch.

Connectivity

If your internet went out this morning, how long before your team could not do their jobs?

For most businesses, the answer is somewhere between immediately and within the hour. That is fine to acknowledge. What matters is whether you have thought about it. A business that relies on cloud tools for everything is also entirely dependent on a reliable connection to reach them. Knowing your exposure does not fix it, but it lets you make an informed decision about whether a backup connection is worth the cost.

Devices and software

Are the devices and software your team uses still receiving security updates from the manufacturer?

When a vendor stops releasing updates for a product, they have also stopped patching the security holes in it. Those holes stay open indefinitely. Running an operating system or application that no longer receives updates is not just a performance issue. It is an ongoing exposure that grows over time. Knowing which devices and software in your business are approaching end of life, and having a plan to replace them, is part of running a stable operation.

What to do with your answers

If you counted more yeses than nos, your foundation is in reasonable shape. There may be gaps worth addressing, but you are not starting from zero, and adding capability from here makes sense.

If the count was roughly even, you are in the most common category. These businesses are not failing. They are functional and often growing. But there are meaningful gaps that, individually, look manageable and, together, create real exposure. A single incident, whether a lost device, a compromised account, or a failed recovery, has a way of surfacing several of them at once.

If you counted more nos than yeses, the honest read is that your business is carrying more risk than it probably realizes. None of these gaps are unusual. Every one of them is addressable. But they are worth addressing before adding complexity, not after.

The businesses that tend to get into the most trouble are not the ones that ignore technology entirely. They are the ones that keep layering new tools and new hires onto a foundation that was never quite solid, each addition quietly depending on something that was not as stable as it appeared.

What comes next

This self-assessment is a starting point, not a prescription.

Some of these gaps take an afternoon to close. Others take more planning. The sequencing matters. Knowing which problem to address first, and which ones can wait, is where the real work begins.

If the questions above surfaced more than you expected, we are happy to have a conversation about what that means for your specific situation. No pressure, no pitch. Just an honest look at where you are and what makes sense from here.