What exactly will you deliver to my business?
Ask me to name the finished task in your employee's words. For that Saugus electrician, it might be assigning incoming requests to the dispatcher. You can inspect an assignment. A promise to transform the operation gives that dispatcher nothing to check. I want the proposal to say what changes and how your staff will recognize completion.
I break the job into a trigger, an action, and a destination. What starts it? What does it do? Where does the result appear? I also list what stays outside the scope. Otherwise a tool built to collect a request can drift into making decisions you never approved. Write the limit down before the build.
How will you prove it works with our setup?
Ask for a test using the kind of request your team receives. I can prepare a fictional record without opening a customer's private file. Then look at the saved result where it belongs. If my assistant says it assigned a request, your assigned employee should find it. The assistant's statement is not the proof.
Next, ask me to break the connection. I expect the test to show the error, who receives the exception, and how the work recovers. The successful path is only part of the job. You and I should agree on passing conditions before the demonstration starts. Otherwise a polished conversation can distract from a missing result.
Why do you need each account permission?
Make me explain every account permission. Reading, editing, sending, and deleting are different powers. A tool drafting a reply does not need all of them because that makes setup easier. While you evaluate the workflow, I prefer a narrow test environment. I should be able to connect each permission to a task in the scope.
Ask where the information goes and who can see it. For privacy, recording, or automated communication obligations, talk to your attorney for your situation. Bring the proposed process to that discussion. A product badge does not settle your responsibilities. Neither does being told another business uses the same tool. I need to explain your actual setup.
What do we own if we stop working together?
Ask whose name is on each business account and how you retrieve your records. I want the handoff to cover operating instructions, approved prompts, configuration notes, and test evidence. Export limits differ between tools. I need to inspect the setup and explain those limits before your business depends on it, not when you are trying to leave.
Ask me how my access gets removed when the engagement ends. Who keeps administrative control? How does the business keep operating during handover? You should not have to wait for a crisis to learn who can pause the assistant. I want account ownership and an exit plan settled while there is time to check both.
Who supports the workflow after launch?
For support, name the person receiving incident reports and the details they need. Separate included changes from work requiring a new scope. Then ask what your staff does while waiting for help. I want a front desk employee able to keep working. A contact address by itself does not tell them how to recover a failed request.
Ask how updates are tested. A changed service policy or calendar connection can change what the assistant does. I want a controlled test before that change reaches customers. Name who maintains the approved information, reviews failures, and decides whether the workflow still fits its original job. Those responsibilities belong in support, not in somebody's memory.
What would I ask you to show me, Connor?
Use these questions on me. I will walk through the current work with you, identify a limited starting point, and propose a test. Ask which decisions stay with your people. Ask how I will teach your staff and what evidence comes with the handoff. You should not have to guess how the proposed build reaches your desk.
I build and test systems for local businesses. You still need to evaluate the specific proposal I put in front of you. Compare it with the problem you first described. If scope, ownership, testing, or support remains unclear, settle that before hiring. My explanation should make your decision easier to check, not harder to question.