Common questions.
Clear answers about where to start, staying safe, Solo, Solo for Execs, Fractional AI Leadership and the free AI assessment.
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. Our free AI assessment takes about 5 minutes and shows where AI fits your work and what to try first.
What is the free AI assessment?
A free online tool for you or for your whole company. It takes about 5 minutes to your report, about 10 with the optional detail. It asks about your work, how you use AI today and what kind of information you hold, never client names or client data. Your report opens on screen and we email you the link. It is built with rules Chase wrote, so no AI service 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?
Less than most people expect. We do the setup. Your time goes into a short onboarding and brief weekly coaching using your own work.
Is it actually safe to use AI with sensitive information?
The risks can be managed with the right setup, but no tool is safe in every case. Turn training off, use a team workspace for shared client work, keep AI drafting while a person sends, and have IT 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 with good context and instructions. Have a person check facts, figures and sources before anything important goes out. Build that check into the workflow.
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 your fee?
Usually a monthly subscription per person, billed directly by the provider. 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 AI Leadership
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, depending on how many people we support and how fast you want to move. AI subscriptions are separate.
Measures are agreed up front and reviewed 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 AI Leadership?
Fractional AI Leadership gives one accountable operator responsibility for how AI enters the organization. Sidekick helps choose the workflows worth changing, implements the first useful changes, and establishes controls, adoption, measurement, and ownership around them.
We begin by understanding the work. 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. Then a 90-day plan with measures agreed up front and reviewed every 30 days. Your team keeps the workflows, operating context, controls, and decision record.
Who is this for?
Fractional is for organizations where AI use is spreading without shared priorities, controls, or ownership. Usually owners and executives of growing service firms of 50 to 300 people. The best fit has an accountable executive sponsor, one or more workflows to improve, and people who can help define the current process and review the result. You do not need a large technical team. You do need an owner for the business decision and access to the people who run the work.
We've tried AI before and it didn't stick. Why would this be different?
We begin with the current workflow, what already exists, and the reason earlier attempts did not hold. Then we define the result, boundary, owner, and review process before changing the tools.
The first change stays small enough to test on live work. We record what passed, what needed correction, and what the evidence supports next. Useful parts of the existing setup stay. Weak parts are improved or stopped instead of being scaled by default.
What does the engagement look like: timeline and commitment?
We start with the free AI assessment and a fit conversation about the work, sponsor, current process, and main constraint. 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. Then a 90-day plan with measures agreed up front and reviewed every 30 days.
Ongoing Fractional starts with a firm 90-day commitment. There is no convenience cancellation after work starts. Every engagement has a written scope, decision rights, and transfer path. Any continuation requires a new written scope.
Where does a company start?
With the Free AI Assessment at /assessment, a free tool that takes about 5 minutes to your report, then a free 30-minute fit call. If Fractional fits, the hands-on work starts in its first two weeks.
Do you replace our existing tools?
Usually not. We start with the workflow and the systems already involved, then choose the smallest platform change that fits the work, risk, access, and review requirements. A new subscription or specialist integration is added only when the operating need justifies it.
What does human-in-the-loop actually mean in practice?
It means the workflow names which actions AI may prepare, which actions a person must review, and which decisions remain fully human. The review boundary depends on the data, impact, reversibility, and client policy. Consequential sends, commitments, account changes, and production actions stay behind explicit approval unless the client has separately designed and authorized a different control.
How do you handle our data?
Your data stays yours. Data handling is defined before we build, with work performed in client-controlled accounts and tools wherever practical. Any data sent to an AI provider or connector follows the permissions, plan, and settings you approve. Sidekick does not use client data for model training. Provider training and retention terms depend on the service and plan you choose, and that boundary is documented before launch.
Do we need a technical team to work with you?
Not for every engagement. We need an accountable sponsor and people who understand the workflow. Technical, security, data, or system owners join when the work touches their responsibilities. Specialist implementation is scoped separately when the operating requirement needs it.
What happens when the engagement ends?
Your team keeps the delivered workflows, operating context, controls, documentation, and decision record, subject to the agreed licences and third-party platform terms. The engagement ends through a defined handoff or continues only through a separately agreed scope. Sidekick does not make ongoing dependence a condition of using what was delivered. You keep using everything we set up. The only limits are on reselling or distributing it.
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.
What if you're at capacity?
We are hiring and growing. For now, we take on a limited number of engagements at a time. If we are at capacity, we work with a network of trusted partners who can support clients who are unable to wait for the next available slot with Sidekick.
Most Fractional engagements start after at least one failed rollout. Read what actually changed for five owners →
Bringing AI to your company? Start with the free AI assessment, about 5 minutes to your report, then a 30-minute call.
Solo and Solo for Execs
15 questionsWhat's included in Sidekick Solo?
Solo is a configured personal AI workspace built around your role, priorities, communication style, and recurring work, with hands-on coaching to help you become proficient in 30 days. The $1,800 CAD fee includes the setup, a plain-language guide, a 30-minute onboarding session, seven days of refinements, four weekly 30-minute coaching sessions with Chase, and 30 days of async support.
How much time will this actually save me?
The result varies with the work, source quality, review burden, and how consistently you use the workspace. Solo does not promise a fixed number of hours or a guaranteed return.
The first goal is dependable use: the workspace starts with your context, recurring work, and review preferences instead of a blank chat. During onboarding and hands-on coaching, you learn how to brief it, check the result, and adjust the workflow.
A useful Solo workflow should make a recurring task easier to prepare or review without lowering the quality you need. Use your own before state to judge whether it helped.
Can't I set up an AI workspace myself?
You can. Solo is for people who want the workspace configured around their role, priorities, communication style, recurring decisions, and review preferences. The value is the connected context and operating structure, with onboarding, refinements, and hands-on coaching to help you become proficient in 30 days.
How much does Sidekick Solo cost?
Sidekick Solo is $1,800 CAD, paid once. It includes your configured workspace, a plain-language guide, a 30-minute onboarding session, seven days of refinements, four weekly 30-minute coaching sessions with Chase, and 30 days of async support. Hands-on coaching helps you become proficient in 30 days. Your AI account or 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?
Add them as a person: one to three others at $1,800 CAD each, each with their own setup and coaching. 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?
AI leadership in 30 days. Know what AI should and shouldn't do in your company. Solo for Execs is $2,900 CAD once, instead of Solo's $1,800. It is for leaders who also decide how staff use AI, or explain the firm's AI plan to a board, partners or team. You get everything in Solo, plus a strategy brief, a staff AI-use policy, talking points and a rehearsal before your meeting, a 90-day roadmap, and 90 days of advice after. About 5 hours of your time in all. It can go on a training or professional development budget.
How long does setup take?
The workspace is built and configured before delivery. Once it is ready, opening it in your account and starting your first session takes only a few minutes. A 30-minute onboarding session is included with every Solo delivery so Chase can walk you through the system and answer questions. Four weekly 30-minute coaching sessions and 30 days of async support are also included, to help you become proficient in 30 days.
Do I need any technical skills?
No. You describe how you work in plain language and Sidekick handles the setup. After delivery, you open the workspace, ask for work, and review the result. No coding or system administration is required.
What is a skill?
A skill is a repeatable way the workspace handles a specific kind of task, such as preparing a meeting brief, drafting a follow-up, or reviewing a week of commitments. Sidekick configures each one around your approved context and review preferences.
Which AI system do I need for Sidekick Solo?
Solo can work with Microsoft Copilot, ChatGPT, Claude, or another suitable AI system. 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 workspace runs in your own AI account or another client-controlled account approved for the work. Sidekick does not have ongoing access to your live sessions or account after delivery unless you explicitly share something for support. Provider training, retention, and privacy treatment depends on the service, plan, and settings you choose. Review those settings against the sensitivity of your work. Sidekick does not use your client content for model training or sell it to third parties.
What if Solo doesn't work for me?
Every Solo delivery includes seven days of refinements, four weekly 30-minute coaching sessions with Chase, and 30 days of async support. If a skill does not fit how you work, we review the mismatch and adjust the instructions, output format, or approved context where appropriate. The goal is a workspace you can use and review confidently.
What stays under my control?
You decide what context the workspace may use and review important output before it becomes an external action or commitment. Solo can prepare work and help with repeatable steps; it does not replace your judgment or authority. You keep using everything we set up. The only limits are on reselling or distributing it.
What if I want more help after I'm set up?
Your first month already includes four weekly 30-minute coaching sessions and 30 days of async support. After that, bring the next outcome to Chase. Additional support or work is scoped separately only when the need, owner, boundary, and expected result are clear.
What if I start with Solo and later want a Fractional engagement?
Solo and Fractional solve the same operating problem at different scales. A future Fractional engagement can reuse relevant personal context and working patterns when the organization has a shared workflow, accountable sponsor, and appropriate access. Contact Chase to discuss the organization-level need.
The fastest answer is a 30-minute call.
If it is not the right fit, we will tell you.
Send a note or book a 30-minute call. No preparation needed.