Twenty questions to figure out where your technology is helping and where it is costing you. Takes about 10 minutes. No email required. No score at the end. Just honest answers and what to do about them.
Your Website
The thing most of your prospects see first. Is it working for you or just existing?
Can a new client find you, understand what you do, and contact you in under 60 seconds?
Your website is a brochure, not a tool. It should be doing work for you around the clock.
Does your website load in under 3 seconds on a phone?
Slow sites lose visitors before they read a word. Test yours at pagespeed.web.dev. If the score is below 70, it needs attention.
Can you update your own content without calling a developer?
If every text change requires a vendor, you do not own your site. You are renting it.
Does your site show up when someone searches your business name?
This is the baseline. If Google does not know you exist, nothing else matters until this is fixed.
Internal Tools and Workflows
The systems your team uses every day. Where the real time gets lost.
Is there a process your team does more than 20 times a week that involves copying data between systems?
Good. That is a common time sink. If yes, this is the first thing to automate.
Can a new team member get up to speed on your tools in less than a week?
Complex tooling means fragile operations. If one person leaves and the system breaks, you have a single point of failure.
Do you have a single place where client information lives, or is it spread across email, spreadsheets, and sticky notes?
Scattered data means missed follow-ups, duplicated work, and decisions made on incomplete information.
When something breaks in your tech stack, do you know who to call?
This is the most expensive gap. Not having a technical owner means problems get ignored until they become emergencies.
Data and Security
Where your client data lives, who can access it, and what happens when things go wrong.
Do you know where all your client data is stored right now?
If you cannot answer this in one sentence, your data is probably in more places than you think. That is a risk.
Could your business recover if your primary computer was stolen or destroyed today?
If the answer involves 'I think we have backups somewhere,' you need to fix this before anything else.
Does every team member use unique passwords and two-factor authentication?
This is the lowest-cost, highest-impact security improvement. Fix it this week.
Do you have a written policy for what happens when an employee leaves?
Accounts that stay active after someone leaves are one of the most common security holes in small businesses.
Communication Systems
How you talk to clients and how your team talks to each other.
Do client messages come through one channel, or are they scattered across email, text, DMs, and voicemail?
Every channel is a place where messages get lost. The fewer the channels, the fewer the dropped balls.
Can you find every conversation you have had with a specific client in under 2 minutes?
If this takes longer, your communication system is not a system. It is a collection of inboxes.
Do your clients know what to expect after they reach out to you?
Set expectations once and automate the follow-up. The silence between first contact and first response is where trust gets lost.
AI and Automation Readiness
Whether AI makes sense for your business right now, or whether it would be a waste of money.
Do you have at least one process that is repetitive, rule-based, and takes more than 2 hours per week?
If no, AI automation probably is not your priority right now. Focus on the sections above first.
Is your business data mostly digital, or is a significant portion still on paper?
AI works on digital data. If you are still paper-heavy, the first step is digitization, not automation.
Do you understand what AI can and cannot do for a business your size?
Most business owners either think AI can do everything or nothing. The truth is narrow and specific. This is worth a conversation.
Have you been pitched an AI tool by a vendor in the last 6 months?
If yes, be cautious. Most vendor-pitched AI tools solve problems you do not have. Start with your actual pain points, not their product.
what to do next
How to read your results
Count the red items. If you have more than three, your technology is actively costing you money and time. Start there.
If most of your answers were green, your systems are in reasonable shape. The amber items are optimizations that will make your team faster, but they are not emergencies.
If you are unsure about any of these questions, that uncertainty is itself a data point. Not knowing where your data lives or who owns your infrastructure is a red-level problem disguised as ignorance.
Three things you can do right now
- 1Fix the password problem. If your team is not using unique passwords and two-factor authentication, stop reading and fix that today. It takes 30 minutes and prevents the most common breach vector.
- 2Test your backups. Not "do you have backups." Test them. Can you actually restore from them? If you have never tested a restore, you do not have backups. You have hope.
- 3Identify the 20-times-a-week task. Ask your team: what is the one thing you do over and over that you wish someone would automate? That is your first automation target.
Want someone to run this for you?
I do this diagnostic live with business owners in 30 minutes. I look at your actual systems, not a checklist. You leave with a clear read on what to fix, what it would cost, and whether I am the right person to help.