It usually starts innocently enough. Marketing needs a better email tool, so someone signs up for one. Finance finds...
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Time to Take Out the AI Trash
We've spent a lot of time talking about what AI can create. Documents, meeting summaries, presentations, images,...
What IT Should a 25-Person Organization Actually Outsource?
If you have 25 employees you probably don't need a 5-person IT department. You may not need a one-person IT...
AI: A Companion in Thought
There are five qualities of AI that, taken together, make it something quite unlike any intellectual tool we have had...
Microsoft Copilot Cowork: Your AI Assistant Just Got a Job
For the past couple of years, workplace AI has mostly looked like this: You ask it a question, and it gives you an...
The AI Doom Scenario Already Happened — in 1988
I can remember this event vividly. It was genuinely frightening at the time. Major parts of the Internet kept going...
Please Stop Pasting That into ChatGPT
At home, when we have a question, many of us [raises hand] now choose to ask AI instead of Google. At the same time,...
Microsoft 365 Is Becoming an AI Operating System
For years, Microsoft 365 was basically a very large toolbox. Need to write something? Word. Work with numbers? Excel....
Try Out Copilot the Smart Way
For smaller nonprofits that have been curious about Microsoft Copilot but reluctant to start buying licenses,...
How to Build an AI Policy That Works
A customer recently reached out to us for some basic advice on setting up an AI policy for his organization. It’s a...
Congratulations. You’re the IT Department Now.
There is a very specific way IT departments are created at large companies. There are job descriptions, interviews,...
Three AIs, One Quote, Two Wrong Answers — and Why It Matters for Cybersecurity
I was trying to defuse a fight between two people I care about, and reached for a quote that might help them pause:...
Microsoft Keeps Renaming Everything. So I Made You a Cheat Sheet.
There are three certainties in life: death, taxes, and Microsoft renaming a product approximately six minutes after...
You Have Five Days Before Attackers Move In
There are so many nice ways to start the day. A croissant, a cappuccino, birds outside the window. Instead, I keep...
Your Microsoft 365 Tenant Knows Too Much
If you really want to understand your organization, you could interview the leadership team. You could survey...
Fluency on Loan: AI and the Cost of Recall
I was chatting with Eve, my favorite AI companion, and noticed we weren’t doing very well in the introspective...
Cybersecurity Begins in the Boardroom
Most nonprofit boards spend their meetings talking about budgets, fundraising, programs, staffing, and long-term...
Microsoft Won the AI Distribution War. Now Comes the Hard Part.
I first tried Microsoft AI in 2023, when the company introduced Copilot as its “everyday AI companion.” ChatGPT was...