Common questions.
Plain answers about where to start, keeping data safe, and our one-person and company-wide services.
The AI Opportunity Map is a free questionnaire, about 10 minutes. You get a short written report on where AI fits your work.
Getting started and staying safe
15 questionsI know AI could help, but I don't know where to start. What should I do first?
Start with where your week actually goes. Your free AI Opportunity Map shows where AI fits your work and what to try first.
What is the AI Opportunity Map?
A free questionnaire for you or for your whole company. It takes about 10 minutes and gives you a short written report, your map. It asks about your work, how you use AI today and what kind of information you hold, never client names or client data. Your map opens on screen and we email you the link. Chase built the AI Opportunity Map with AI. It runs on fixed rules, so no AI reads your answers. Chase only contacts you if you say yes.
Should I try it myself before hiring anyone?
Yes, if you have the time. This playbook shows what to try on your own first. Bring in help when setup keeps stalling or you want it working across your business.
What does AI actually do day to day in a business like mine?
Most owners start with the inbox, meeting follow-up, proposals and quotes, and reports. See real examples by type of work.
Which of my tasks should AI do, and which should stay with me?
Anything repetitive, text-heavy or rules-based is a good candidate. Judgment, relationships and final decisions stay with you.
How much of my time will this take?
It depends on the service. Solo, where Chase sets up your AI and coaches you for 30 days: about 3 hours over the month. Solo for Execs, which adds the documents a leader needs for the board, partners or staff: about 5 hours. Fractional, where Chase leads your company's AI rollout part-time: about 4 hours from the executive who leads it in the first two weeks, and 45 minutes from each other leader. After that, each person's time is set in the 90-day plan.
Is it actually safe to use AI with sensitive information?
No AI tool is safe in every case. These steps lower the risk. Switch off the setting that lets the AI company learn from what you type. Use a team workspace for shared client work, have AI draft while a person sends, and have your IT provider approve connections first.
Our IT provider has to approve things. How does that work?
Your IT provider usually approves the licences, the connections to email and files, and the sharing settings. We speak with them directly or send a checklist, whichever you prefer.
Do I have to connect my email and everything else?
No. You choose what AI can see and what it can do. Many start with drafts only: AI prepares, you send.
What if the AI gets something wrong?
AI can make mistakes even when you give it good background and clear instructions. Have a person check facts, figures and sources before anything important goes out. Build that check into how the job runs.
Will it sound like me, or like generic AI?
It learns from your own writing and your corrections, so drafts get closer to your voice over time.
Which AI tool should we use: Copilot, ChatGPT or Claude?
It depends on the systems you already use and the work you want done. What we build isn't locked to one platform, so you can change later.
Will it connect to our CRM or industry software?
Often yes, sometimes only partly. We check on the fit call. Custom software is rarely the first answer.
What will the AI subscriptions cost on top of Sidekick's fee?
Usually a monthly subscription per person, billed directly by the provider. Most clients use Claude's Max 5x plan, about US$100 a month per person. The provider sets the price and can change it. We recommend the plan that fits before you buy anything.
Are there grants that help pay for this in Canada?
Some programs can help with training and implementation costs. Here's what's available and who qualifies.
Fractional
13 questionsWhat does a Fractional engagement cost?
From $6,000 CAD a month, with a 90-day minimum. Most engagements run $6,000 to $12,000 CAD a month. The price depends on how many people we coach at once, how fast you want to roll out, and how much we coordinate with your IT provider. AI subscriptions are separate and billed by the provider.
You set your own measures in the first two weeks and we review them every 30 days. If a milestone slips because of us, we keep working at no extra fee until it's delivered. You keep everything we build.
Starting smaller: one to three people on Solo at $1,800 CAD each, or the leader alone on Solo for Execs ($2,900 CAD).
What is Fractional?
Sidekick leads your AI rollout for a monthly fee, and Chase is your lead. We pick with you which jobs to change first, set AI up on them, train your people and write the rules for using it.
Who is this for?
Fractional is for companies where people use AI unevenly and nobody is in charge of it. Usually owners and executives of growing service firms of about 20 to 300 people. The best fit has a leader in charge of the project, recurring work you want done faster or better, and people who can explain how the work is done today and check the result. You do not need a large technical team.
We've tried AI before and it didn't stick. Why would this be different?
We begin with how the work runs today, what already exists, and why earlier attempts did not hold. Before changing any tool we agree what should improve, what AI may not do, who is responsible and who checks the work.
Each change is tested on live work first. We record what passed, what needed correction and what to do next. Useful parts of your existing setup stay. Weak parts are improved or stopped.
What does the engagement look like: timeline and commitment?
We start with your free AI Opportunity Map and a 30-minute fit call about the work, who will be in charge on your side and what is in the way. In the first two weeks, Chase meets your leaders (up to six), shows AI working on your firm's own templates and past work (not client files), and presents what he found to your leadership team.
Fractional is a committed 90-day term. We review results with you every 30 days and judge them at day 90. After day 90 you choose whether to continue. Every engagement has a written scope.
For larger firms, 90 days covers your leaders and your first teams. More teams follow in later 90-day terms. If you need to move faster, we bring in vetted partners or subcontractors under Sidekick's contract, and we tell you who before they start. We won't rush the work or spread ourselves thin to win a deal.
Where does a company start?
With the free AI Opportunity Map, then a free 30-minute fit call. One department, such as sales, can start on its own at $6,000 CAD a month, with an executive who leads it on your side. Its leaders go first, then its team.
Do you replace our existing tools?
Usually not. We keep your current email, files and other software where they work, and change as little as possible. A new subscription or integration is added only when the work needs it.
What does keeping a person in charge mean in practice?
For each job, we write down what AI may prepare, what a person must review and which decisions stay with a person. How much a person checks depends on how sensitive the information is and what happens if it is wrong. Nothing is sent, promised, published or changed in an account without your approval, unless you agree otherwise in writing.
How do you handle our data?
We don't ask for your client files. If a job needs one, you choose it, case by case. How data is handled is agreed before we build, and the work runs in your firm's own Claude, ChatGPT or Copilot business account. Anything sent to an AI provider or connector follows the permissions, plan and settings you approve. Sidekick does not train AI on client data. What each provider keeps, and for how long, depends on the plan, and we write that down before launch.
Do we need a technical team to work with you?
Not for every engagement. We need a leader in charge of the project and people who understand the work. Your IT person joins when we connect a system they look after. Custom software is quoted separately.
What happens when the engagement ends?
Your team keeps everything we build: the setups, the rules, the documentation and a written record of what was decided and why. You can use and change all of it inside your business. You may not resell it. The AI providers' own terms still apply. The engagement ends with a handoff, or continues only under a new written scope.
Who is Fractional not a fit for?
Not a fit: teams that need a full-time AI lead, or leaders who aren't convinced AI is for them.
Who delivers the work?
Chase leads your engagement and is your single point of contact. If someone else runs part of it, you know who before they start.
Tried AI and it didn't stick? Read why AI fades, and what keeps it going. →
Bringing AI to your company? Start with your free AI Opportunity Map, then a 30-minute call.
Solo and Solo for Execs
14 questionsWhat's included in Solo?
Chase sets AI up around your role, priorities, writing style and recurring work, then coaches you so you are proficient in 30 days. Your setup is a set of plain files: the background on your work, instructions and step-by-step procedures the AI follows. They load into your own ChatGPT, Claude or Copilot account, and you keep them. The $1,800 CAD fee includes the setup, a plain-language guide, a 30-minute onboarding call, seven days of refinements, and four 30-minute calls with Chase, ideally one a week, plus email or text to Chase between calls for 30 days. The last call is your day-30 review.
How much time will this actually save me?
We do not promise a number of hours. Pick one task you repeat and time it before and after. How much you save depends on the task, the material you give the AI and how often you use it.
Can't I set AI up myself?
You can. Solo is for people who want Chase to set it up around their role and recurring tasks and coach them through the first 30 days.
How much does Solo cost?
Solo is $1,800 CAD, paid once. See "What's included in Solo?" above for what that covers. Your AI subscription is separate. The provider bills you directly and can change its plans, prices, limits and terms. There is no ongoing Sidekick subscription. Solo can go on a training or professional development budget.
Can someone else on my team use Solo?
Each person gets their own Solo. Up to three more people, such as your assistant, can each get their own setup and coaching at $1,800 CAD. If you want your whole team using AI with shared rules and measures, that's Fractional, and it starts with your leaders.
What is Solo for Execs?
Solo for Execs is Solo, plus the documents a leader needs to answer the board, partners or staff. You get the AI position brief (3 pages on where your firm will and will not use AI), a staff AI-use policy, talking points with a practice run before you present, and a personal 90-day plan: which jobs AI takes on, in what order. It costs $2,900 CAD once, instead of Solo's $1,800, and includes 90 days of advice afterwards by email or voice note, and a call at day 60. About 5 hours of your time in all. It can go on a training or professional development budget.
How long does setup take?
Chase builds your setup within 48 hours of your payment. Opening it in your account takes a few minutes, and you can do it with a short guide or on a call with Chase.
Do I need any technical skills?
No. You describe how you work in plain language and Sidekick handles the setup. After delivery you open it, ask for work and review the result. No coding or system administration is required.
Which AI system do I need for Solo?
Solo works with Claude, ChatGPT or Microsoft Copilot. Chase will recommend the best fit based on your work, tools, data settings, and expected use. You pay the provider separately, and the provider can change its plans, prices, limits, and terms.
Is my data private?
Your Solo setup runs in your own AI account, or another account your business controls. Chase never logs in to your account and never asks for your password. He sees only what you choose to share. What each AI provider keeps, and for how long, depends on the plan and settings you choose, so check them against how sensitive your work is. Sidekick does not train AI on your client content or sell it to anyone.
What if Solo doesn't work for me?
If part of the setup does not fit how you work, tell Chase. During the seven days of refinements and the coaching calls he changes the instructions, the output format or the background files until it does.
What stays under my control?
You choose which files and background the AI can use, and you check anything important before it goes out. The AI prepares work and helps with steps you repeat. Decisions stay with you. You can use and change everything we set up inside your business. You may not resell it. The AI providers' own terms still apply.
What if I want more help after I'm set up?
Your first month includes coaching and support. See "What's included in Solo?" above. After that, tell Chase what you want to do next. Extra work is quoted separately once we agree what it should achieve.
What if I start with Solo and later want a Fractional engagement?
Solo is for one person. Fractional is for a leadership team and the company. Moving from Solo or Solo for Execs to Fractional? We credit half of what you paid toward your Fractional engagement, on your last invoice, for up to two Solo purchases made in the three months before Fractional starts. We also reuse what fits from your Solo setup.
The fastest answer is a 30-minute call.
The first call is free. If it is not the right fit, we will tell you.
Have a question first? Ask it here, text Chase at 778-999-0985, email, or connect on LinkedIn.