Before You Buy Another AI Tool, Answer These 12 Questions

Brennan Gerle Jan 26, 2026 5:19:08 PM

A lot of leaders tell me the same thing:

“We know we need to be doing something with AI, but we don’t know where to start.”

So they:

Let a few people play with ChatGPT on the side
Buy a new AI feature in a tool they already use
Or wait, because “it’s not in the budget this quarter”

The real problem usually isn’t the tools.
The problem is not knowing if you and your business are actually ready to use AI in a smart way.

This article gives you 12 simple questions to answer before you buy anything else.

Two Things You Need to Check

There are two sides to AI readiness:

You as a leader – how you think about and use AI
Your business – your processes, data, and people

If either side is weak, AI projects stall out.

Let’s start with you.

Part 1: Your Personal AI Readiness (6 Questions)

These questions are about your own habits and understanding as a leader.

1. Do you use AI in your own work?

Be honest:

Do you use tools like ChatGPT or Copilot at least a few times a week?
Or do you mostly hear about AI from other people?

If you’re not using AI yourself, it’s very hard to lead your team through it.
You don’t need to be an expert, but you do need some hands-on experience.

If your answer is “no”:
Make your first “AI project” simply using AI yourself for:

Drafting emails or documents
Summarizing long reports
Getting a first pass on ideas or plans

Do that for a few weeks before you think about big automations.

2. Do you know the basics of how AI works?

You don’t need technical language. You just need to know:

AI predicts text based on patterns in data
It can sound confident and still be wrong
It needs clear instructions and human review for important decisions

If it still feels like “magic” or a black box, you’ll either:

Trust it too much, or
Not trust it at all

Neither is good.

3. Can you “talk” to AI in a way that gets good results?

This is about prompting.

When you don’t like the first answer from an AI tool, do you know how to:

Add more context? (“I’m a COO at a 50-person construction company…”)
Give an example? (“Here’s the style I want. Please match it.”)
Ask for a rewrite? (“Shorter, clearer, less formal.”)

Leaders who can do this get much more value out of the same tools.

4. Do you know what’s safe to put into AI tools?

Many leaders are either:

Too relaxed (copying sensitive info into public tools), or
Too scared (no one is allowed to use anything)

You should be clear on:

What’s never allowed (for example, specific client names, financial details, regulated data)
What’s okay if it’s anonymized
What’s low-risk and great for experimentation (generic text, public info, ideas)

If you’re fuzzy on this, your team definitely is.

5. Can you explain to your team why you’re using AI?

People are watching what you say.

Can you clearly explain:

Why you want to use AI (time savings, quality, speed, consistency)
How it should help people, not secretly replace them
What’s in and out of bounds

If you can’t explain it simply, adoption will be slow and resistance will be high.

6. Are you ready to sponsor a small pilot, not just sign off on a tool?

AI change fails when leaders:

Approve a budget
Hand it to IT or a “tech person”
And then walk away

You don’t have to manage the details.
But you do need to:

Help pick a first use case
Remove blockers
Talk about it often so people know it matters

Part 2: Your Business AI Readiness (6 Questions)

Now let’s look at your organization.

7. Are your key processes clear?

Pick a process: project delivery, job costing, customer onboarding, service requests.

Ask yourself:

Could I hand this to someone and have them understand the steps?
Do we know where the delays and repetitive work are?

If no one can explain the process, AI can’t help much.
You’ll just automate chaos.

8. Is your important data in one place (or at least a few known places)?

Think about:

Customers
Projects or jobs
Inventory or assets
Tickets or issues

Is that info:

Mostly in shared systems (CRM, project tool, ERP), or
Scattered across inboxes, spreadsheets, and people’s heads?

AI and automation rely on data.
If your data is scattered or untrusted, that’s a sign to fix before you go big on AI.

9. Do your current tools play well with AI and automation?

Ask:

Do we already use tools that have AI built in or can connect to it easily?
Or would everything require heavy custom work?

You don’t need a perfect stack.
But it’s useful to know if you can:

Start inside tools you already pay for, or
If you’ll need some upgrades first

10. How does your team really feel about AI?

Listen for what people actually say:

“I’ve been using it, it helps a lot with X” → curiosity / early adopters
“This is going to take my job” → fear
“This is just another buzzword” → skepticism

You don’t need everyone excited.
But you do need:

A few open-minded people to pilot with
Clear communication from leadership about what AI is and isn’t for

11. Do you have any written guidelines for AI use?

Not a 30-page policy. Just a simple, clear set of rules like:

Approved tools vs. not approved
What data is never allowed
When human review is required (for example, anything client-facing, legal, or financial)

Without this, people are guessing.
Some will avoid AI. Others will push boundaries without realizing it.

12. Do you know where a small AI experiment could help first?

Look for work that is:

Boring and repetitive
Rule-based
Low risk if something small goes wrong

Examples:

Drafting project updates instead of starting from a blank page
Summarizing meeting notes and pulling out next steps
Sorting and tagging incoming emails or tickets
Turning messy notes into a first draft SOP

If you can name one or two of these, you’re ready for a focused pilot.

What To Do With Your Answers

If you made it this far, you don’t need another long strategy document.

Here’s a simple way to move forward:

Write down your honest answers to the 12 questions.
Don’t overthink it. A few bullets for each is enough.
Circle 1–2 areas about you as a leader to improve.
For example:
- “I’m going to use AI three times a week for the next month.”
- “I’m going to learn what’s safe / not safe to put in AI tools.”
Circle 1–2 areas about the business to improve.
For example:
- “We’re going to document one core process.”
- “We’re going to write a one-page AI usage guideline.”
Pick one pilot use case.
Something:
- Contained
- Measurable
- Useful

Then run that pilot for 30–90 days.
Measure time saved, errors reduced, or speed improved.
Only then think about expanding.

Make This Easier: Take the POLR AI Readiness Assessment

If you’d like help walking through this in a more structured way, I built a short assessment you can use.

You’ll answer questions like:

How often you actually use AI in your daily work
How confident you feel using it and asking it good questions
How your business handles processes, data, and risk today

You can use it:

As an individual leader, to see where you’re ready and where you need to build confidence
For your business, to see where AI is most likely to help first

Take the assessment here:
https://www.polrai.com/assessment

After you complete it, you’ll have a clearer picture of:

Where you’re already in good shape
Where you need some foundation work
And which 1–2 AI moves are worth focusing on in the next 90 days

If you want help turning that into a concrete plan, you can request an AI Readiness & Opportunity Audit from that page, and we’ll figure out what makes sense for your situation.