After your map
You have your map. Here is how to act on it, in the order leaders usually ask. Six questions, each with one article to read and one free tool to use.

Start with your free map
Answer questions about your work and get your first three jobs for AI, your stage and a 90-day plan. About 5 minutes. Everything below works without it too: the tools are blank, so you fill them in.
Go through it with Chase
Chase Bernier runs Sidekick. In 30 minutes he can walk through your map, or your situation if you have no map, and help decide where to start.
Six steps, in the order leaders ask
Start at step 1, or jump to the question you have now. Your map gives your stage: Using, Trusting or Redesigning. How the three stages work.
Step 1: Why now?
Your staff are already trying AI. Setting the rules now is easier than changing habits later.
What to do this week
- Say where you stand in one line: Using, Trusting or Redesigning, and how far in.
- Write down what clients, staff or competitors already expect from you.
- Put the first 90 days, the cost and the decision you need on one page, and send it to whoever signs off.
Step 2: Is it safe?
Usually, on a business account with security basics turned on first. In our client work, every security problem came from weak passwords or phishing. None came from AI.
What to do this week
- Security basics first: two-step sign-in, strong passwords and phishing protection on email and files.
- List which systems hold client, staff or financial information, and what AI may reach in each.
- Then choose the tool. Start with read-only access and drafts only, so nothing sends on its own.
Step 3: What will it cost?
Business AI tools list at about CAD 28 to 41 per person a month. Outside help and your team's time cost more, so ask before you pay anyone.
ReadWhat AI costs a Canadian business: tools, help and timeUse · Checklist to printAI vendor checklistWhat to do this week
- Ask any provider what you'll be able to do at day 30 and day 90, and how you'll measure it.
- Get the full cost in writing: tool seats, usage charges, their fees, and what happens if usage runs over.
- Ask for the hours your team will spend on setup, training and checking the work.
Step 4: Where do we start?
Pick one or two jobs your people do every week, and start there.
What to do this week
- Pick a job that repeats every week and that someone already finds tedious.
- Write the steps down before AI touches it. If the steps live in one person's head, start there.
- Write down a "before" number for that job this week, such as hours a week or days to turn it around.
Step 5: How do we roll it out?
Leaders first, then the people others already ask for help, then everyone else. Finish the first job before you add the next.
ReadHow to train your employees on AI: building a network of AI championsUse · Table to print or download90-day AI trackerWhat to do this week
- Weeks 1-2: leaders start on one approved tool and use it daily on the first job.
- Weeks 3-12: get the first job running, then add a second. Everyone else joins from week 7, with someone they already ask for help.
- Day 90: compare your numbers with the "before" ones, then decide to keep, widen or stop.
Step 6: What happens after rollout?
Decide where the freed hours go before you promise your staff anything.
ReadAI is handing your team back hours. Who decides where they go?Use · 10-minute worksheetThe hours testWhat to do this week
- Count the hours AI frees up on one task, after the time people still spend checking its work.
- List the useful work waiting for those hours: catching up, getting ahead, or new work.
- Tell the team what you'll try first, promptly and plainly.
The four free tools
Blank versions anyone can use. Print them, or fill them in on screen.
AI vendor checklist
Eight questions and five red flags before you pay any AI provider, with tick boxes for up to three.
Open →Fill in, copy or emailIT sign-off note
The order to follow, who approves what, and a ready-to-send note for your IT provider.
Open →Table to print or download90-day AI tracker
A week-by-week plan for your first 90 days, with your before and day-90 numbers.
Open →One-page templateBoard AI brief
One page for your partners, board or manager: where you stand, the first 90 days, the cost and the decision you need.
Open →Get a version filled in for your firm
The free AI Opportunity Map fills in all four for your firm: your first jobs, your stage, a dated 90-day plan, a note for your IT provider and a one-page brief. It takes about 5 minutes.
Free map: sidekickorchestration.ai/assessment