A PRACTICAL GUIDE / CHOOSING A PARTNER
How to choose an AI automation partner for your small business
Before you hire someone, ask them to walk through a task your team does every week. You should leave knowing what they would change, what you would pay for, and what your team would still need to do. Here’s what I would ask, and how I handle the same questions in my own work.
Updated
Talk through your workflow with meFree · 20 minutes
THE SHORT ANSWER
Start with the work you need help with.
Ask each person how they would handle the same task in your business. Get clear on what they will build, what it costs to run, how you will test it, and who looks after it. Ask to see relevant work and find out what they did themselves.
Go to the comparison worksheet01 / START HERE
Bring the task that keeps getting stuck.
Pick something your team repeats: following up on an inquiry, putting a report together, or copying information between tools. Explain who does it, how often, and where they have to stop and chase someone.
Something like this is enough
“Our office copies each inquiry into a spreadsheet, then assigns someone to follow up. Sometimes the same request arrives twice. Sometimes the details are missing. We want each request assigned once and the incomplete ones flagged for someone to check.”
Made-up example to show the level of detail to bring.
Give everyone you speak with that same example. Ask how they would handle the missing details and duplicates, as well as the easy version of the task.
You don't need to write a technical brief before talking to me. Show me how the work happens today. I look for steps we can simplify before deciding what to build. Sometimes a feature you already pay for is enough. Here's how I compare existing software and custom tools.
02 / CHECK THE SCOPE
What are you paying for?
A proposal might cover a plan, a working build, a software subscription, or someone running the system for you. Check which parts are included.
A plan
Useful when you need to work out what to fix first. Ask what the plan contains and whether building it is a separate project.
A build
Ask what your team will be able to do when it is finished, what is excluded, and how you will check it together.
Software
Check the subscription, usage charges, setup, and the work your team still has to do.
Ongoing help
Agree who checks failures, fixes connections, and handles changes. Ask what the monthly fee includes.
For my work, a clearly defined task can go straight to a build proposal after a free conversation. If several processes are tangled together, we can discuss the audit first. You agree to that step before paying for it. See how I price workflow builds and ongoing costs.
03 / LOOK AT THE WORK
Ask them to show you what they built.
Ask what they handled themselves, who uses it, and what happened when something went wrong. Find out whether you are seeing a demo, work for a client, or a system they use in their own business. A private system may need a redacted walkthrough. A reference, when available, gives you another person's account of the work.
My examples come from businesses I run or help operate. Here are two that show the decisions behind the build.
I keep the sends in my hands.
I built ReadyCrate's partnership workflow for my moving-tote rental business. It prepares email drafts and keeps track of follow-ups. I review the drafts, choose what to send, and handle the replies. When it found a thread mismatch, it held the follow-up for me to check.
See the ReadyCrate workflow →Each vendor sees their own information.
I built a vendor portal in a business I help operate. Vendors use it for sales, stock, and restocking. Their workspaces are scoped to their own data. That's the kind of access rule I want spelled out and tested before people start using a tool.
See the vendor portal →
04 / COMPARE THE WRITTEN SCOPE
Put the proposals side by side.
Use this with any two proposals, including mine. Download a copy to write on, or expand the worksheet below. Mark each point documented, unclear, or does not meet our needs. Write down what each person has agreed to and what you still need to ask. A missing detail is worth clarifying before you decide.
PREVIEW / 3 OF 10 CHECKS
- Business problem
- The same workflow, its current owner, and the intended operating change.
- Deliverable
- What this phase produces and what is excluded.
- Relevant experience
- An artifact or walkthrough, the provider’s exact role, and their relationship to the work.
View full worksheet
On a small screen, scroll sideways to see both provider columns. The PDF has space to write your answers.
| Check | Evidence to request | Provider A | Provider B |
|---|---|---|---|
| Business problem | The same workflow, its current owner, and the intended operating change. | ||
| Deliverable | What this phase produces and what is excluded. | ||
| Relevant experience | An artifact or walkthrough, the provider’s exact role, and their relationship to the work. | ||
| Inputs and access | Tools and data required, permissions, and who authorizes access. | ||
| Human decisions | What needs approval and who handles uncertain or sensitive cases. | ||
| Acceptance | Normal and exception cases, duplicate handling, and the agreed success measure. | ||
| Full costs | Setup or build, subscriptions, usage, support, and remaining internal work. | ||
| Ownership and exit | Accounts, documentation, exports, code and transfer terms, and licensing limits. | ||
| Aftercare | Monitoring, incident contact, maintenance responsibility, and change requests. | ||
| Next decision | The smallest agreed step and the evidence needed to continue. |
ILLUSTRATIVE PROPOSALS
Two descriptions of the same connection
Proposal A: “Connect the inquiry form to the task list and demonstrate the result.”
Proposal B: “Connect the inquiry form to the task list; test missing details and duplicate submissions; agree account access; hand over instructions; name who checks failures and what support includes.”
Ask Provider A whether those details are included. The extra words in Proposal B only help if they describe work you need and the provider agrees to do it.
These are invented examples, not real competitors or customer experiences.
05 / TRY THE AWKWARD CASE
How will you know it works?
Agree what you will test before calling the build finished. Include the person who does the task today.
- Run a normal task, then try one with missing or incorrect information.
- Send the same request twice. Check that it does not create the same action twice.
- Check what each person can see and change, including someone who should not have access.
- Decide which messages or actions need approval and who handles an uncertain AI answer.
- Walk through a failure: who notices, how do you pause it, and how do you restart without repeating completed work?
Pick a result you can check, such as an inquiry reaching the right person with the details they need. If you want to measure time saved, include the checking and cleanup people still have to do.
For a more detailed reference on AI oversight and testing, see the NIST AI Risk Management Framework Core.
06 / AFTER LAUNCH
Who looks after it?
Connections break, software changes, and your process will change too. Ask who checks for errors, who you contact, and which fixes or changes cost extra.
Get the account access, software bills, instructions, and export options clear before handoff. Agree what code you receive and what you can transfer to another builder. Check for limits from any third-party software.
In my proposals, the build, handoff, and any ongoing support are spelled out separately. I show your team how to run the workflow and leave instructions for approvals and failures.
07 / WORKING WITH ME
Is this the kind of help you need?
I work with Kansas City small-business owners on the recurring work that gets in the way: reports, follow-up, copying data, and keeping track of what needs attention. I look at the process, simplify it where we can, then build the connections or tools around it.
If that sounds like your problem, bring me one example. We can talk through the task and decide whether to scope a build or take a closer look first.
If an existing feature solves it, use that. If the process is still changing or the task rarely happens, it may be worth waiting. Use the same questions and worksheet with anyone you are considering, including me.
BRING ONE WORKFLOW
Show me what keeps landing back on your plate.
A spreadsheet, a report, or a rough description is enough to start. We'll talk for 20 minutes about how the task works today and what would help. If there's a project to scope, we can agree on the next step from there.
Free · 20 minutes · Kansas City + remote