Technology Self-Assessment

Section 1 — Your Technology Today

1. How many software systems does your business actively use?

(CRM, accounting, project management, website, email, HR, scheduling, etc.)

2. How many of those systems talk to each other automatically?

Most are connected Some are connected, others require manual work Most require manual work to share data I do not know

3. Do you have documentation of how your systems are set up and how they connect?

Section 2 — Risk and Dependency

4. If your primary technical person left tomorrow, how long before something broke?

We'd be fine — knowledge is well distributed A few days before we hit a serious problem Immediately — there are things only one person knows I'm not sure, and that worries me I do not know

5. Have you had a critical system go down or malfunction in the past 12 months?

No significant incidents Yes, minor issues that were resolved quickly Yes, something that cost us time, money, or client trust Yes, more than once I do not know

6. Are there manual processes your team runs regularly that you know should be automated?

No, we're fairly automated A few, but they're manageable Yes, several — they take meaningful time each week Yes, and they're a constant source of errors or frustration I do not know

Section 3 — Technology and Growth

7. Is your current technology built for the size of company you are now, or the size you were two or three years ago?

It scales well with where we are today It's starting to show strain Built for a smaller company and we're working around its limits Not sure — nobody has evaluated it recently I do not know

8. In the past 12 months, has a technology limitation caused you to delay, decline, or lose a business opportunity?

9. How confident are you in the technology decisions being made for your business right now?

Very confident — clear strategy and the right people executing it Somewhat confident — moving, but not sure we're going the right direction Not very confident — decisions feel reactive rather than strategic I don't have visibility into technology decisions and that concerns me I do not know

Section 4 — Leadership and Oversight

10. Who is responsible for technology strategy at your company?

A full-time CTO or VP of Technology A senior developer or IT manager who also handles strategy The founder or CEO, alongside everything else Nobody specifically — it's distributed or reactive I do not know

11. When a significant technology decision needs to be made, how does it typically get decided?

We have a clear process and the right people in the room Depends on the decision — some handled well, others not Decisions tend to get delayed because nobody owns them Decisions get made quickly but not always correctly I do not know

12. Do you receive regular reporting on the state of your technology in language you can understand?

Yes — I get clear updates and understand what they mean I get updates but they're too technical to be useful I mostly hear about technology when something breaks No — I have very little visibility I do not know

Section 5 — Open Questions

There are no wrong answers. These questions tend to open the most useful part of the conversation. Answer in your own words.

Keep answers general. Do not include information you consider private or sensitive — IP addresses, server names, network names, credentials, or internal system details. Describe the situation; the specifics can wait for the call. Like all email, this is transmitted in clear text and is not end-to-end encrypted.

What is the one technology problem that costs your business the most time or money right now?

If you could fix one thing about how technology works in your business in the next 90 days, what would it be?

Is there a technology decision coming up in the next 6 months that you're not confident about?

Technology State of the Business

Section 1 — Your Technology Today

Section 2 — Risk and Dependency

Section 3 — Technology and Growth

Section 4 — Leadership and Oversight

Section 5 — Open Questions

Your answers are ready to send.