Baseline for the chosen workflow
Without a before number, nobody can tell whether the pilot worked. Measure it before anything is built.
Grow revenue
An AI readiness assessment that ends with a decision, not a slide deck
Most owners do not need to be convinced that AI matters. What they lack is a clear answer to a simpler question: where, in this business, would it actually pay back, and what would have to be true first? Without that answer, firms either buy tools nobody uses or wait while competitors learn.
Signs you need this
- Several people have AI ideas but nobody has decided which one to try first.
- You have paid for AI features or tools that few people use.
- Your team spends hours on recurring work that feels like it should be automated.
- You are unsure whether your data and systems are in good enough shape for AI.
- A competitor, client or board member keeps asking what your AI plan is.
An AI readiness assessment looks at your real workflows, data, systems and people, then ranks a short list of opportunities by value, effort and risk. A useful one ends with one recommended pilot, a baseline to measure it against and a plain view of what to fix first. Sometimes the right recommendation is a settings change in software you already pay for.
How it works
Map the work that costs the most
Interview the owner, managers and front-line staff. Walk through a handful of recurring workflows step by step, noting the time spent, handoffs, rework and which systems hold the information.
Check data and systems
Review your CRM, practice or field service software, accounting system and shared files. Look at data quality, integrations, access controls and what your current licenses already include.
Score the opportunities
Rate each candidate on value to revenue or margin, effort, risk, data readiness and how willing the team is to change. Include non-AI fixes, because many problems are process or configuration issues.
Pick one pilot and set a baseline
Choose the opportunity with the best balance of value and feasibility. Agree how it will be measured, such as time per task or response time, and record today's numbers before building.
Write a short roadmap
Document the pilot scope, acceptance criteria, likely tools and budget, plus the next two or three opportunities and the policy or data work needed before them. Keep it to a few pages.
Ways to do it
| Approach | Best fit | Notes |
|---|---|---|
| Self-assessment | Small firms with a curious owner and a few hours to spare. | Use a checklist to list recurring tasks, time spent and systems involved. It is a good start, but it is hard to see your own workflows objectively. |
| Paid diagnostic | Firms that want an outside, vendor-neutral view before committing to a project. | A fixed-scope review of a few weeks that produces a ranked list and one pilot recommendation. Ask whether the provider earns commissions on the tools they suggest. |
| Assessment as part of a fractional engagement | Firms that want the same people to assess, deliver and measure. | In a 90-day engagement, the first 30 days diagnose and set a baseline, then the pilot is built and measured. This avoids the report that sits on a shelf. |
| Vendor-led assessment | Firms already committed to a specific platform. | Software vendors and resellers often offer free assessments. They can be useful for that product, but expect recommendations that favor what they sell. |
How we deliver this: AI automation for small business or fractional CTO leadership, scoped in writing and run over 90 days. See pricing or the sample scope.
What we would measure
Hours spent on top recurring tasks
A simple time log across the team shows where effort goes and keeps the roadmap honest.
Software spend on unused or overlapping tools
Assessments often find savings that help fund the pilot. Track what you stop paying for.
Time from assessment to pilot decision
The assessment is only useful if it leads to action. Weeks, not months, is the target.
Risks and how we handle them
| Risk | Mitigation |
|---|---|
| An assessment that produces a long list and no decision. | Require it to end with one recommended pilot, a baseline, acceptance criteria and a budget range. |
| Recommendations biased toward a product. | Ask advisers to disclose any vendor relationships, and insist on seeing options that use tools you already own. |
| Ignoring data, policy and people issues. | Include data quality, an AI usage policy, client confidentiality and staff training in the assessment, not as afterthoughts. |
When not to do this
Skip a formal assessment if you already know exactly which workflow is costing you and have a clear way to fix it. Just scope that project with a baseline. It is also too early if the business is in the middle of a major system change, a merger or a leadership transition. Wait until the core systems and decision makers are settled.
Common questions
What is an AI readiness assessment?
It is a structured review of your workflows, data, systems and team to find where AI and automation would pay back, what is blocking them and what to do first. A good one ends with a ranked short list, one recommended pilot and a baseline to measure it against.
How long does one take?
For a 5-150 person service business, usually two to four weeks. That covers interviews, a review of key systems and data, scoring the opportunities and agreeing a pilot. In a 90-day engagement it sits within the first 30 days, followed by delivery and measurement.
Will it always recommend AI?
No, and you should be wary of one that does. Many of the best fixes are process changes, cleaned-up data, an integration between existing systems or a setting turned on in software you already pay for. AI is one option among several.
What do we need to prepare?
Access to the people who do the work, a list of your software and what you pay for it, and a rough idea of where time and money go. Read-only access to key systems helps. No technical preparation is needed.
What happens after the assessment?
You decide whether to run the recommended pilot, with your own team, with the assessor or with someone else. The roadmap should be clear enough to hand to any competent partner. If the honest answer is that nothing is worth building now, the assessment should say so.
By industry
AI readiness assessment and roadmap for your industry
Guides
How to hire an AI consultantHow to hire a fractional CTOIs a fractional CTO worth it for a small business?How much does a fractional CTO cost?When to hire a CTOMicrosoft Copilot for small business
Questions
How much does a fractional CIO cost?vCIO vs CIO?How much does an AI consultant cost?What does an AI consultant do?How much does AI automation cost for a small business?
Glossary
Agentic AIFine-tuningAI readiness assessmentFractional CTOFractional executiveTechnology roadmapProcess mappingAcceptance criteria
Other solutions
Next step
Bring one expensive workflow. Leave with a clear next step.
In 30 minutes we look at one recurring workflow, what it costs you today and whether there is a credible case to improve it. If there is not, we will say so.
Book a 30-minute workflow review
Not ready to talk? Take the 3-minute check
30 minutes with Phil or Martin. No technical brief, no pitch deck. Phil or Martin replies personally, usually within one business day.