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Anu Jolliffe

Anu Jolliffe

Innovation Strategist, Grey Sky Tech · PMP · Victoria, BC

I help Canadian businesses adopt AI, Microsoft 365 Copilot, and automation without the false-start projects and shelfware. Workshops, strategy advisory, and implementation, with a bias toward what your team can actually use on Monday morning.

Articles by Anu (12)

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.

July 12, 202611 min readRead

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.

July 5, 202611 min readRead

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.

June 26, 20269 min readRead

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.

June 14, 202612 min readRead

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.

June 2, 20268 min readRead

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.

April 10, 20267 min readRead

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

March 29, 20267 min readRead

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.

March 26, 20268 min readRead

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.

March 24, 20267 min readRead

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.

March 10, 20264 min readRead

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.

March 5, 20264 min readRead

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.

February 28, 20265 min readRead