Sidekick Orchestration
// Insights

InsightsPlain answers on putting AI to work.

For owners, leadership teams, and the advisors and IT providers who work with them. Start with the path that fits you, or find the question you’re asking.

Leading a team? Follow the six-step guide

Free toolsBrowse by questionGuides and resources

Chase BernierFounder, Sidekick Orchestration

// Free tools

Two free tools,about 10 minutes each.

// Start here

Three short reading paths.Pick the one that sounds like you.

Path 01

Running it yourself

You own the business or do the work yourself, and you want AI to take on some of your recurring tasks.

  1. Why AI doesn't stickTried AI and it faded? Why that happens, and what keeps it going.7 min read
  2. What five early AI setups taught me about where to startWhere five owners found the right first job for AI.6 min read
  3. What AI handles inside my one-person businessWhat AI runs in a one-person business, and what still needs a person.8 min read
  4. How working with us worksWhat happens after you say yes: time, cost and what you keep.7 min read
Path 02

Leading a team or company

You need AI working across a team or the whole company.

  1. Why now?What AI is already changing for staff, and how to tell how far your firm has come.
  2. Is it safe?What happens to your data, what staff may put into AI, and how the main tools compare.
  3. What will it cost?What AI tools, outside help and your own team’s time cost, and how billing works.
  4. Where do we start?Find the first jobs worth handing to AI, and the places a rollout tends to stall.
  5. How do we roll it out?Train leaders first, then champions, and track what changes after training.
  6. What happens after rollout?Decide where the freed hours go, and what is fair if there isn’t enough new work.
Path 03

Partners and IT providers

You coach or advise owners, or look after their IT, and they are asking you about AI.

  1. Six AI questions fractional executives need to answerThe questions your clients are already asking.14 min read
  2. AI and sensitive information: a few settings and a few decisionsWhat needs protecting, the three settings that matter, and where an IT provider fits.8 min read
  3. What changes when you connect AI to your businessWhat AI can read, what it may change, and who approves.6 min read
  4. The AI Delegation MapSort a client's work into what AI can run, what AI can speed up while a person checks, and what stays with a person, before you suggest anything.One-page tool
// Guide for leaders

Leading a team or company:from first questions to life after rollout.

Six steps, each one a question leaders ask. Read them in order, or start at the step you’re on.

  1. // Step 01

    Why now?

    What AI is already changing for staff, and how to tell how far your firm has come.

  2. // Step 02

    Is it safe?

    What happens to your data, what staff may put into AI, and how the main tools compare.

  3. // Step 03

    What will it cost?

    What AI tools, outside help and your own team’s time cost, and how billing works.

  4. // Step 04

    Where do we start?

    Find the first jobs worth handing to AI, and the places a rollout tends to stall.

  5. // Step 05

    How do we roll it out?

    Train leaders first, then champions, and track what changes after training.

  6. // Step 06

    What happens after rollout?

    Decide where the freed hours go, and what is fair if there isn’t enough new work.

// After step 06

Finished the guide?

Bring what you read to a free 30-minute call with Chase Bernier, and leave with the first tasks to hand to AI and who learns first.

Book a free 30-minute call
// Browse by question

More articles,sorted by the question they answer.

What does it cost, and what does it take?

The setup time, programs that help pay for it, and when a custom build is worth it. For prices, see step 3 of the guide.

Start with thisAI adoption has a setup tax. I rarely see it in the budget.Setup, troubleshooting and learning take real time. How leaders can fund that work without overbuilding.13 min readRead

Where should we start?

How to pick the first piece of work, get your leaders to agree on what they mean by AI, and decide what stays with a person.

Start with thisShould AI do this work?Score one recurring task on five practical factors and choose the right role for AI.9 min readRead

How do I get better results day to day?

How to give AI clearer instructions, find out why it repeats a mistake, and keep your corrections.

Start with thisWorking with your AI assistant: a guide for your first monthsThe guide our clients get with their setup: what to say, the daily habits, and how to hand off bigger work.12 min readRead

Which tool, and what should we keep track of?

Compare business AI tools, and the records a small company should keep once AI can reach its data. For the main comparison of Copilot, Claude and ChatGPT, start with step 2 of the guide.

Start with thisIs Copilot safer than Claude for business?Usually Copilot for a Microsoft 365 firm, once overshared folders are fixed. Five questions on training, access, actions, storage and location.5 min readRead
// By industry

Accounting, advisory and insurance firms

Where AI fits first in Canadian accounting, advisory and insurance firms.

// Guides, tools and sample maps

Hands-on helpfor setting AI up yourself.

Free guides and tools for people doing the setup themselves, and sample AI Opportunity Maps for invented firms.

Sample AI Opportunity Maps

Guides and tools you can use today

ArchiveOlder commentary on AI models and the AI market (4)

Written earlier in 2026. The news in these pieces has moved on, so they are kept here for reference.

// Next step

One next step,whichever reader you are.