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Insights & Guidance

Practical advice on Artificial Intelligence, Automation, Adoption and Training for Canadian businesses.

The One Thing You Can Do Today to Start Your Company's Digital Transformation
Adoption and Training6 min read

The One Thing You Can Do Today to Start Your Company's Digital Transformation

Transformation stalls when five good ideas compete for the same Tuesday. Here is the one to start with, and the ten-minute check that shows if you need it.

TL;DR Do one thing. Look up your company's domain on a WHOIS service and read the registrant field. If it names a former web designer, a reseller, or nobody anyone can name, every improvement you make from here sits on ground you do not own. The check takes ten minutes and costs nothing.

Anu JolliffeAugust 16, 2026
Small FixesAdoptionStrategyMicrosoft 365Small Business
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Sixty Seconds, Second Place, and the Ten-Year-Old Idea Behind chequeup
Artificial Intelligence10 min read

Sixty Seconds, Second Place, and the Ten-Year-Old Idea Behind chequeup

I went to a Saturday hackathon meetup for the snacks, pitched an idea I have carried for ten years, and came second. Here is why I can finally build it.

Anu JolliffeAugust 11, 2026
Product DevelopmentchequeupHackathonSmall BusinessCanada
Your AI Policy Is Only Useful If Your Team Buys Into It
Adoption and Training12 min read

Your AI Policy Is Only Useful If Your Team Buys Into It

The organisations getting real value from AI are not the ones with the longest policies. A field note on why buy-in beats documentation, and where to start.

Anu JolliffeJuly 19, 2026
Microsoft 365CopilotAI PolicyGovernance
Page 63, 1994: Thirty Years of Building Ahead of the Curve
Automation11 min read

Page 63, 1994: Thirty Years of Building Ahead of the Curve

Three decades of building, from a 1994 island BBS to today, and the events page and mailing list I run on Microsoft 365 for Business at zero monthly cost.

Anu JolliffeJuly 12, 2026
Microsoft 365SharePointSmall Business
Why "Just Use Gmail" Stops Working When Your Business Gets Serious
Adoption and Training11 min read

Why "Just Use Gmail" Stops Working When Your Business Gets Serious

Your business email address is a trust signal, and a free email service sends the wrong one. The people you want to work with read it before they read you.

Anu JolliffeJuly 5, 2026
Microsoft 365Small BusinessSecurityStartupsEmailStrategy
57% of the Team Had Never Opened the AI They Already Pay For
Adoption and Training9 min read

57% of the Team Had Never Opened the AI They Already Pay For

Most of the team I trained had never opened the secure, governed AI that ships free with their Microsoft 365 licence. Here is why, and how to fix it.

Anu JolliffeJune 26, 2026
Microsoft 365CopilotWorkshop
Ottawa Crafted a World-Class AI Strategy. Main Street Is Still Waiting.
Artificial Intelligence12 min read

Ottawa Crafted a World-Class AI Strategy. Main Street Is Still Waiting.

Canada's AI for All is an excellent strategy with one gap: direct adoption dollars for small business. A leaner, CDAP-style fix and local AI pros.

Anu JolliffeJune 14, 2026
AI StrategySmall BusinessStrategyCanadian AI Policy
Why I Replaced Google Search With Microsoft 365 Copilot
Artificial Intelligence8 min read

Why I Replaced Google Search With Microsoft 365 Copilot

A client texted me at 23:13, fed up that AI summaries have buried the real sources in Google. My answer: I switched to Microsoft 365 Copilot two years ago.

Anu JolliffeJune 2, 2026
Microsoft 365CopilotStrategy
Tales from the Crypt: Your Software Subscriptions Have Vampires and Zombies
Adoption and Training7 min read

Tales from the Crypt: Your Software Subscriptions Have Vampires and Zombies

Every software subscription and cloud services review we run finds 10-30% in savings. Three true stories of zombie licences, vampire subscriptions, and shadow IT.

Anu JolliffeApril 10, 2026
StrategyShadow ITTales from the CryptMicrosoft 365
Queue Smart: Giving ER Patients Their Time Back
Automation7 min read

Queue Smart: Giving ER Patients Their Time Back

How we built Queue Smart, an ER patient communication platform that shows queue position, estimates wait times, and lets patients leave while keeping their spot

Anu JolliffeMarch 29, 2026
HackathonPower PlatformStrategy
Why Microsoft 365 Is the Only Choice for Canadian Small Businesses
Adoption and Training8 min read

Why Microsoft 365 Is the Only Choice for Canadian Small Businesses

Microsoft 365 costs less than Google Workspace, scales from solopreneur to enterprise, and includes tools most businesses never knew were included.

Anu JolliffeMarch 26, 2026
Microsoft 365StrategyWorkshopGoogle WorkspacePower Platform
The Microsoft 365 for Business Training Nobody Ever Got (And Why We Start There)
Adoption and Training7 min read

The Microsoft 365 for Business Training Nobody Ever Got (And Why We Start There)

Why we always run a Microsoft 365 for Business fundamentals workshop before discussing Copilot, and what happens when people finally understand the platform.

Anu JolliffeMarch 24, 2026
CopilotMicrosoft 365Workshop
5 Signs Your Business Is Ready for AI Adoption
Adoption and Training4 min read

5 Signs Your Business Is Ready for AI Adoption

Not sure if your business is ready for AI? Here are five clear indicators that it's time to explore what AI can do for your operations.

Anu JolliffeMarch 10, 2026
Strategy
RPA vs. Traditional Automation: What Canadian Businesses Need to Know
Automation4 min read

RPA vs. Traditional Automation: What Canadian Businesses Need to Know

Robotic Process Automation and traditional automation solve different problems. Here's how to know which one your business actually needs.

Anu JolliffeMarch 5, 2026
RPA
How to Build an AI Adoption Plan That Your Team Will Actually Follow
Adoption and Training5 min read

How to Build an AI Adoption Plan That Your Team Will Actually Follow

Most AI initiatives fail because of people, not technology. Here's how to create an adoption plan that gets your team on board and keeps them there.

Anu JolliffeFebruary 28, 2026
Strategy