A pilot should end with a decision, not with “interesting”. An AI pilot for company email fits into two weeks if you plan it. This is the plan we suggest for AddSync AI, and it works for any AI tool that touches company mail.

Before day 1

• Pick five to ten people who handle a lot of email, such as sales, accounts or the office.
• Choose one or two use cases, for example thread summaries and meeting preparation.
• Set data filters and agree what is out of scope.
• Decide which option to test: your own Claude or ChatGPT, or the AddSync chat window.
• Define success in advance, for example minutes saved a day or a score from users.

Who does what

One person can hold two roles in a small company. What matters is that each job has a name next to it.

The 14 days

1. Day 1: connectConnect the mailboxes, choose who may use AI and close the folders you do not want the AI to read. Most teams are ready on the same day.
2. Days 2 to 7: learnGive each person a short list of prompts, such as the ones in 7 AI prompts for meeting preparation. Ask them to use the assistant daily and note what worked. Check the journal on day three for surprises.
3. Days 8 to 13: measureCompare with your success numbers. Run a ten-minute survey. Review the journal again, and fix filters that were too strict or too open.
4. Day 14: decideLook at the journal and at what your people say. Continue, change the rules or stop.

What to try first

What to measure

Keep the measures few and simple. A short survey with three questions is enough: did it save time, was the answer correct, would you keep using it. Add one number from the journal, such as how many people used the AI on more than half of the days. Resist the urge to count everything.

What to look for in the journal

• Which tools run most often: search, show, save a draft or propose.
• Which people stopped using it, and why.
• Requests that hit closed folders, which show where a filter is doing its job.
• Spikes on one day, which usually mean a real need or a confusing result.

The journal records who used which tool and when, not the text of the mail, so you can review it without reading anyone’s mail.

Day 14: three good outcomes

Any of the three is a result. The only bad outcome is a pilot that ends without a written decision.

Questions and answers

How many mailboxes should I connect?

A few are enough. Choose people who work with mail every day, so that you see real use within 14 days.

Do I have to move my mail?

No. AddSync AI reaches the mail where it is. Exchange Server stays in your own server room.

Can I stop before day 14?

Yes. You can switch AI off for one person, for a group or for everyone at any time.

Which option do I test, A or B?

Either. Option A uses your own Claude or ChatGPT. Option B uses the chat inside AddSync, with the model in an EU region.

Written by the AddSync team.