This is the full reference version of the working session. Every slide is here in order, from the opening headlines through the nine modules to your first 90 days.
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Working Session: From Aware to Fluent. Discuss, practice, debrief, apply.
You have seen the keynote. Today we roll up our sleeves: we discuss, you practice, we debrief, you apply.
Before the practical work, let's zoom out. The headlines are loud and often wrong. Here is what the data actually says about AI, jobs, and the shape of the work ahead.
Is AI replacing the jobs? And why the work is more likely to explode than disappear.
Leave with the honest picture, so you lead from facts, not fear.
The 2026 headlines say AI is taking the jobs. Zoom out: Amazon ran the largest corporate cuts in its history and still employs roughly double its 2019 staff.
5%
of 2025 US layoffs named AI as the reason (rising toward ~22% in 2026, but still the minority). Most were post-pandemic over-hiring correction.
Challenger, Gray & Christmas
Jevons Paradox, 1865: when James Watt made the steam engine more efficient, Britain burned more coal, not less. Cheaper to use meant used everywhere. Efficiency expands demand. The same thing happens with capability.
Cheaper branches meant more branches. The job roughly doubled.
170M created, 92M displaced, worldwide (WEF, 2025).
The real squeeze is the bottom rung. Entry-level workers in AI-exposed roles are down about 13%, junior developers about 20%, while experienced workers are flat or better off (Stanford, 2025). The question is not "will AI replace all jobs." It is whether your people and your structure adapt fast enough.
The single habit that separates people who get gold from AI and people who get mush: how you frame the ask. Role, Context, Task is the shape.
How to think about the AI, then the Role, Context, Task framework.
Take a vague prompt you actually use. Rebuild it as RCT.
Share your before and after. Which layer felt unnatural?
A pocket template you can paste into any chat.
The skill is not handing everything to the AI. It is knowing which part is yours. You frame the work and you verify the result. The AI carries the load in between.
A prompt structure is a repeatable shape you fill in. Same skeleton every time. It forces you to name what the AI needs up front, so it stops guessing and answers what you actually meant. Role, Context, Task is the one to learn first.
Same question, three layers. Watch the answer climb as you give it a role, then the real specifics, then the exact output you want.
Give it a perspective
Hand it the specifics
Name the exact output
Think of something you would type into ChatGPT or Claude today: an email, a plan, a tough message. Pull it apart and rebuild it with these three layers.
Who should the AI be? What experience or perspective should it bring to this?
What does it need to know to be useful? The audience, the constraints, the specifics only you have.
What exactly do you want produced? Length, format, tone, what to include and leave out.
Turn to the person next to you. Read each other your before and after.
When you ran the RCT version, what got sharper? What did it stop getting wrong?
Was Role the awkward one? Context? Most people overdo one and skip another.
Name one real prompt you will switch to RCT tomorrow, or you will forget by lunch.
Copy this. Keep it where you work. Fill in the blanks any time you want a sharper answer on the first try.
Role, Context, Task - Three layers. Always in this order.Role: You are [the role with the experience or perspective that fits this].
Context: [What this is for. Who will see it. The constraints. The specifics that make this not generic.]
Task: [What you want produced. Length. Format. Tone. What to include, what to leave out.]
Before you give me the final version, ask me anything you'd need to make this right.
RCT is what you bring to one chat. Custom instructions are what the AI remembers across every chat. Set them once and every answer starts warmer, sharper, more you.
Why a one-time setup pays back forever, and exactly what to put in.
Draft your own custom instructions from a starter template.
Compare notes. What did you include that others didn't?
Paste them in today, the lazy way: let the AI interview you.
Industry, company size, who you serve, what makes your situation specific.
What you are responsible for, who you answer to, the decisions you own.
What you are focused on right now. The goals and the headaches.
Direct or warm, short or thorough, the formats you actually use.
Fill in the brackets. Five minutes now saves you an edit on every chat from here on. Keep it tight; you can always add more later.
Starter: tell the AI who you are - Edit everything in brackets, then paste into Settings > Custom instructions.Who I am: [your name, your role, your company and what it does].
What I care about right now: [your top 2-3 priorities or challenges].
How I like answers: [direct or detailed? bullet points or prose? any formats you use a lot?].
Things to remember: [anything it keeps getting wrong, names, products, your market].
Compare with the person beside you.
The best custom instructions are personal. Steal a good idea from your neighbour.
A page of rules can box it in. A single line is too thin. Find your level.
Custom instructions are not the place for secrets or client-confidential detail.
Do not stare at a blank box. Paste this, answer its questions, and let it write a clean set of instructions for you to drop into settings.
Have the AI build your instructions - Paste into a fresh chat. Answer the questions. Copy the result into settings.I want to set up strong custom instructions so you understand me in every future chat.
Interview me: ask me one question at a time about my role, my company, my current priorities, and how I like answers. Keep going until you have enough.
Then write a tight set of custom instructions in the second person ("You are working with...") that I can paste straight into my settings.
Most people use AI to go faster. The real edge is using it to think better: to pressure-test your reasoning before you commit. Two techniques do most of the work.
Reverse prompting, then the devil's advocate move.
Run both on a real decision or message you are sitting on.
What did it surface that you had not considered?
Two prompts worth keeping.
When you only half-know what you want, do not write a long prompt. Hand it the messy intent and say: "Interview me until you have what you need, then answer." It pulls the context out of your head, one question at a time.
The first draft is rarely the best one. Before you accept anything, make it attack its own work: "What is weak here? What would a tough critic say? Now fix it."
Pick a live one, not a hypothetical. The point is to feel it change your thinking.
A decision you are chewing on, a message you cannot start. Tell the AI to interview you first, then answer.
A plan, a price, an email you were about to send. Make it find the three weakest points, then strengthen them.
What did it surface that you had not considered?
Reverse prompting often reveals you had not decided what you actually wanted.
The devil's advocate pass usually lands on something you knew but were avoiding.
This is the shift: not just doing the work quicker, but making a better decision.
Save these two lines. They turn the AI from a faster typist into a sharper colleague.
Reverse prompt + devil's advocate - Use the first when you are unsure; the second before you commit.REVERSE PROMPT:
"Before you answer, interview me one question at a time until you have everything you need to do this well. Then answer."
DEVIL'S ADVOCATE:
"Now take the other side. What are the three weakest points in this? What would a sharp critic say? Then rewrite it to fix them."
So far the AI only knows what you type. Connect it to your email, calendar, and documents and it can work with what you already have, not a blank page.
What "connecting" really means, what it unlocks, and where to draw the line.
Pick one connection to turn on this week. Watch one live first.
Once connected, the AI can read and act where you already work, with your permission.
Triage the inbox, draft replies in context, summarize a long thread.
See your week, find time, prep you for the next meeting.
Pull facts from a real doc instead of you pasting it in.
Reach into the folder where the work actually lives.
Look something up live instead of guessing from memory.
Notion, your CRM, Slack: where your team already operates.
"What needs me today?" and it reads your real inbox and calendar to answer.
"Draft a reply to this," with the whole thread already in front of it.
"Prep me for my 2pm," from the invite, the attendees, and the last notes.
"Summarize this report," pointed at the actual file, not a copy-paste.
You just saw one live. Now make it yours, starting safe.
Your own email or calendar. Nothing client-confidential to start.
Two minutes in settings. Grant access to that single account.
"What needs me today?" or "Prep me for my next meeting."
This is the part people do not believe until they see it. You describe a tool in plain English and the AI builds a real, working version. No code. We will build live.
What Cowork is, then two things I built this way, live.
Name the one tool you wish existed. That is your first build.
Cowork is a mode where the AI does not just answer, it builds. You explain the tool you want in plain language; it writes the software, shows you the result, and changes it as you react. The same skill you have been practising all day.
"Build me a simple dashboard that shows my sales pipeline by stage, with the total value at the top."
$1.84M
Total pipeline: Discovery, Proposal, Closing.

I asked Cowork to build me a tool for writing a murder mystery novel: track clues, suspects, timelines, and keep the plot honest. Here is what it made.

For a fictional business, I had Cowork build the dashboards a CEO would actually use: strategy, sales, operations, people. Let me walk you through them.
Do not think about the technology. Name the small tool or dashboard you keep wishing existed, the one nobody will ever build for you. Then start it with a line like this.
Cowork starter - Open Cowork, paste this, fill in the brackets, and let it build a first version.I want to build a simple [tool or dashboard] that helps me [the job to be done].
It should show [the few things that matter most] and let me [the one action I take with it].
Start simple. Build a first version I can look at, then we will refine it together.
"Agent" is the most overused, least understood word in AI right now, and you will be pitched it constantly this year. By the end of this module you will be able to cut through the hype and know exactly what to ask.
What an agent actually is, the ones you may already own, and what is real versus hype.
The five questions to ask before you trust any agent.
"AI that does things for you." So broad that every product now claims it. Mostly noise.
AI that takes actions in your tools, not just chats. It does multi-step work and uses software on your behalf.
A model, plus instructions, memory, tools it can call, and some autonomy to choose the steps itself.
Answers you
Does a task you direct
Pursues a goal across steps and tools
Strip away the branding and an agent is a junior employee you have hired. You give it a job, some knowledge, some skills, and keys to certain systems, and you decide how much rope it gets. Manage it like one.
With Copilot Studio you build agents grounded in your own company data, living in Teams and SharePoint, and publish them to a shared catalog for the org.
Answers staff questions from your real HR docs (leave, benefits, expenses), right inside Teams.
Pulls the account, the last notes, and recent news to brief a rep before a call.
Walks a new hire through their first-week checklist, grounded in your SOPs.
Take an agent that lives in Slack, right where your team already works. It is the same five parts you just saw.
Your channel history and connected apps
Summarize, draft, answer, take action
Your CRM, your calendar, your docs
Same five parts, every tool you use:
40%
of enterprise apps will have agents by 2026, up from under 5%
Gartner, 2025
43% → 27%
trust in fully autonomous agents, in a single year
Capgemini, 2025
24-35%
of real multi-step office tasks the best agents actually finish
Carnegie Mellon / Salesforce, 2025
Momentum is enormous and the limits are real. Treat an agent like a capable but unproven new hire: scope it tightly, supervise the work, and widen its autonomy only as it earns your trust.
Whether a vendor is selling it or your team is building it, the same five questions tell you whether it is ready for real work.
Which systems and which data, exactly.
Where is the line it cannot cross on its own.
A named person responsible for its care and feeding.
Because it will be. What is the catch and the fix.
Is every action logged so you can see what it did.
Before we talk about your plan, look at the field you are playing on. Canada just put a number on it, and the gap between ambition and reality is the whole opportunity.
Where Canada actually stands: the adoption gap, the literacy gap, and the prize.
Decide which side of that gap your business is going to be on.
In June 2026, the federal "AI for All" strategy put adoption on the record. Today, just over one in ten Canadian businesses use AI to do real work. The target is six in ten by 2034.
A 5x jump in under a decade. The country is betting on it.
Among small and mid-sized businesses, the gap is wider
SME AI adoption. Source: AI for All federal strategy, Government of Canada (ISED), June 2026.
44th
of 47 countries on AI training and literacy
KPMG / University of Melbourne, 2025
24% vs 39%
Canadians with any AI training, versus the global average
KPMG / University of Melbourne, 2025
We have world-class talent and one of the fastest-growing digital sectors in the G7. We are also among the slowest countries in the world to adopt AI at scale. The bottleneck is not the tools. It is people who have never been shown how to use them.
The same strategy that named the gap also sized the upside. And adoption is already moving faster than most people realize.
~$200B
productivity upside over the next five years
AI for All, 2026
250,000
new jobs projected by 2031
AI for All, 2026
2x
adoption doubled in one year (6.1% to 12.2%)
Statistics Canada, 2024-25
Drift with the national average. A pilot that fizzles. Training that fades in a month. Plenty of logins, no change in the numbers.
Get your people genuinely fluent. Wire AI into real work. Measure it. Be in the small share of Canadian businesses that is actually pulling ahead.
The rest of today is the how. That is the path.
Everything so far has been personal fluency. This is the leader's question: how do you turn a room of capable people into a company that actually runs better on AI? There is a path, and it has five stages.
Why most AI rollouts stall, the five stages, and the two threads that decide it.
Your first 90 days, written down before you leave the room.
Most leaders start with "which tool?" That is the wrong first question. Look at what actually happens when companies adopt AI:
You do not have to leap to the end. Each stage earns the next, and each one compounds the value of the last.
Value to the business climbs with every stage
Adopting AI is a change program, not a software purchase. Like any reorg, it needs a single accountable owner, not a committee and not "everyone."
79% vs 27%
projects hit their objectives with an effective executive sponsor versus an ineffective one
Prosci, 2024
42%
of companies abandoned most of their AI initiatives in 2025, up from 17% a year earlier
S&P Global, 2025
Know your governance, privacy, and regulatory requirements, then write them down. A one-page policy beats a six-month committee.
Approved tools. Which AI tools are sanctioned, and how new ones get vetted.
Data rules. What can and cannot be put into AI. Client, financial, regulated data.
Who owns it. The implementation lead, and how to raise a question.
The roadmap. Where you are headed over the next few quarters.
63%
of breached organizations had no AI governance policy; shadow AI adds an average $670K to a breach
IBM Cost of a Data Breach, 2025
Not "use AI." A number you want to move. The common three:
Cost to serve, time on reporting, manual admin.
Faster proposals, more selling time, new offers.
Faster response, fewer dropped balls, better service.
1.5x
revenue growth and 1.6x shareholder returns for AI leaders over three years
BCG, 2024
ChatGPT, Claude, Copilot, Gemini are all capable. Pick on fit, not on the demo you saw last. Four questions decide it:
Microsoft 365 leans to Copilot; Google to Gemini. Meet your stack.
Writing, analysis, building, support. Match the tool to the work.
Enterprise data protection, admin controls, where data is processed.
Per-seat pricing across the team, not just a pilot of five.
Generic training fades. Train people on their own workflows, put the exec team through first, and name a champion on each team.
39%
of people who use AI at work have had any training from their company
Microsoft, 2024
+25% / +40%
faster and higher-quality work after training, and the weakest performers gain the most
Harvard / BCG, 2023
We run this on your team's real work. worksmartercompany.com/ai-training
Three filters: it hurts, it happens often, and you can quickly tell if the output is right. Good first candidates show up in almost every business:
Draft from a short brief, in your voice.
Transcript in; owners and due dates out.
Sort, summarize, draft the replies.
Turn raw numbers into the narrative.
60-70%
of the time employees spend today is on activities current AI could help automate
McKinsey, 2023
A workflow, an SOP, even a saved prompt is now a small system. It needs care and feeding, or it quietly breaks.
30-50%
of automation projects fail, which EY attributes to lack of ownership, not the technology
EY
Prompts drift as usage broadens and edge cases appear.
Models change and behaviour shifts underneath it.
Data moves a sheet is renamed, a field deleted, and it breaks.
The builder leaves and takes all the context with them.
Someone builds "a little app that runs on my computer." Getting it to colleagues safely is the real work. The watch-out: by default, "publish" means public on the internet.
Claude Project, custom GPT, Copilot agent. Identity and data stay inside the tool.
Vercel, Lovable, Replit. Fast, but the default is public. You must turn on a login.
Behind your SSO and network. The home for sensitive or business-critical apps.
Power Apps, Retool. Login, roles, and audit trails come built in.
"It works" and "it's safe" are different claims, and the gap between them is exactly where AI-built apps fail.
No secrets in the code, the single biggest risk.
Real authentication, not an unguessable link.
Sensible data handling, what goes in, where it lives.
Accessibility + dependency review, the basics, and what it pulled in.
~2x
the rate at which AI-assisted code commits leak hardcoded secrets versus human commits; vibe-coded apps have shipped with the literal password 'supersecretkey'
GitGuardian / Cloud Security Alliance, 2025-26
Shadow IT exists because the official path is too slow. 69% of security leaders already suspect staff use banned AI tools (Lansweeper). Don't ban it, pave it. Match scrutiny to blast radius:
One user, no sensitive data. Provide the tools and a brand prompt. Don't gatekeep.
Multiple users, non-sensitive. Register it (name, owner, data) and deploy on the paved road with SSO on.
Customer data, money, regulated, or load-bearing. Real security review, IT hosting, named owner, monitoring.
Scaling is not more pilots. It is making the wins repeatable and easy to find, so other teams ask for them instead of being told.
Your ten best prompts, where everyone can find and reuse them.
A known place to see what others have built, and copy it.
People demo what worked. Wins spread by envy, not memo.
~6%
of companies scale AI to real bottom-line value; the ones that do are about 3x more likely to have made it repeatable across the org
McKinsey, 2025
You met agents in Module 6. The final stage is letting them do real, multi-step work, and the rule is the same as with any new hire: trust is earned, in stages.
Start on cheap, reversible mistakes. Low stakes first, where a wrong answer is easy to catch and undo.
Keep a human approving anything that leaves the building or spends money.
Log everything. Every action, so you can audit what it did.
Widen autonomy as the track record earns it. Not before.
Get these two right and the stages take care of themselves. Skip them and even good tools fade within a month.
Leaders go first. You cannot lead a change you have not lived.
Name champions. One per team, with real time to help, not after hours.
Keep practising. Refreshers and show-and-tells, not one-off training.
Pick the outcome. One number per initiative, baselined before you start.
Review monthly. Ask one question: is the number moving?
Know the difference. Between activity and progress. Logins are not results.
The same rule covers a built app, a workflow automation, a saved prompt, or an AI SOP. One row each in a shared registry:
Name + what it does - So people find it and avoid duplicates
Owner (a named person) - Single point of accountability
Backup / team - So it survives the owner leaving
Risk tier (0/1/2) - Drives how much oversight it gets
Data it touches - Compliance and incident response
Where it is hosted - So IT can find it
Last reviewed - Forces care and feeding to happen
Sunset / review date - Default to retiring, not hoarding
Three moves. Write yours down before you leave the room.
Decide what data can and cannot go in. Pick one business outcome to move, and baseline it.
Get your leadership team genuinely using it on real work. You set the tone the org follows.
Find a painful, frequent, checkable workflow. Wire AI in. Measure before and after.
Five minutes. Pays back on every chat from now on.
The one you'd have typed half-baked. Slow down. Use the shape.
Before you commit, make the AI argue the other side.
Start safe: your own email or calendar. Ask it what needs you today.
The little tool nobody else will ever build for you. Start rough.
Three ways to keep going after today.
Custom AI training for your organization. Run this curriculum with your people, or go further with what fits your industry.
worksmartercompany.com/ai-training
We build custom software and automate the workflows holding your team back. Practical AI that pays back fast.
worksmartercompany.com/worksmart-ai
Want to talk through your situation, your goals, or what to do first? Grab a time directly on the calendar.
worksmartercompany.com/book