How Microsoft Copilot Roasted My Week And Revealed How To Work Smarter

I spend most of my week talking about Microsoft 365 Copilot, AI, security, governance and Microsoft Purview.

Like many people, I use Copilot to summarise meetings, find information, draft content and help me move faster through the day.

What I wasn’t expecting was for Copilot to turn those same skills on me.

Earlier this week, it suggested a prompt I’d never considered:

“Summarise my week in the style of a comedy roast.”

Naturally, I had to try it.

I expected a few light-hearted jokes.

Instead, I received what can only be described as an AI-generated audit report.

According to Copilot, I had spent the week:

• Explaining Microsoft 365 Copilot
• Demystifying Cowork
• Answering the same questions repeatedly
• Running workshops
• Delivering webinars
• Chasing registrations
• Fixing slide decks
• Following up on recordings
• Having countless conversations about AI, governance and security

At some point, my calendar apparently stopped being a calendar and became a stress test for Microsoft Teams.

Then Copilot found a message I had sent while discussing an upcoming event:

“Even if I have to crawl, I’ll be there.”

Its response?

“The most Australian Solutions Architect sentence ever recorded.”

Fair.

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The Part That Made Me Stop And Think

The roast was funny.

The next prompt was where things became interesting.

I followed up with:

Summarise my week in the style of a comedy roast. Then analyse my week like a CEO reviewing the performance of a business.

What happened next completely changed my perspective.

The AI stopped looking at my activities.

It started looking at my operating model.

Instead of telling me what I did, it started challenging how I work.

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The Difference Between Activity And Impact

One observation stood out immediately.

A lot of my week was spent creating value.

A lot of my week was also spent being the bottleneck.

That’s an uncomfortable thing to hear.

Especially when you’re busy.

When we look back on our weeks, we often measure success by activity:

• Number of meetings attended
• Number of emails answered
• Number of conversations completed
• Number of workshops delivered
• Number of tasks crossed off

But activity and impact are not the same thing.

The CEO-style analysis wasn’t interested in how much I had done.

It wanted to know:

• What created the most value?
• What only I could do?
• What should be delegated?
• What should be automated?
• What should become a repeatable asset?

That distinction changed everything.

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A Pattern I Had Been Missing

The review highlighted something I suspect many of us experience.

Every week we answer the same questions.

Every week we explain the same concepts.

Every week we solve variations of the same problems.

In my case, many of those conversations were about:

• Microsoft 365 Copilot
• Cowork
• AI adoption
• Governance
• Security
• Licensing
• Readiness

The insight was simple.

If I’m answering the same question repeatedly, there are usually only three possibilities:

Option 1: Keep answering it

This works.

But it doesn’t scale.

Option 2: Create a reusable asset

A blog.

A guide.

A workshop.

A one-page explainer.

A decision tree.

A prompt.

Something people can consume without needing me to rediscover the same answer every week.

Option 3: Build a system around it

The highest leverage option.

Instead of solving individual problems repeatedly, create something that helps solve the problem before it arrives.

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The Most Valuable Question

Of all the questions the AI raised, one stood out.

“What are you spending time on that doesn’t actually require you?”

That’s a dangerous question.

Most professionals spend a large part of their week doing things they are capable of doing.

Far fewer spend their time doing things only they can do.

Those are not the same thing.

The highest-value work often looks like:

• Strategy
• Enablement
• Thought leadership
• Problem solving
• Relationship building
• Creating frameworks
• Translating complexity into action

The lowest-value work often looks like:

• Repeating explanations
• Chasing information
• Manual administration
• Recreating assets that already exist
• Solving the same problem for the tenth time

The AI wasn’t encouraging me to work harder.

It was encouraging me to be more deliberate.

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Why This Matters For AI Adoption

There’s a broader lesson here.

Most conversations around AI focus on productivity.

Can it write faster?

Can it summarise faster?

Can it create faster?

Those are useful capabilities.

But I think the real value is emerging elsewhere.

The most valuable AI outputs I’ve seen recently haven’t been answers.

They’ve been observations.

The technology is becoming increasingly good at identifying patterns in our work that are difficult to see while we’re living them.

The answers were never hidden.

The perspective was.

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My New Friday Ritual

What began as a joke has become something I plan to continue.

Every Friday, I’ll likely ask:

“Summarise my week in the style of a comedy roast.”

Not because the roast itself is valuable.

Because it creates enough distance to reflect honestly on what happened during the week.

And if I’m being honest, the most useful output wasn’t the roast.

It was the follow-up.

The one that challenged my assumptions.

The one that exposed my bottlenecks.

The one that forced me to think about leverage instead of activity.

The one that shifted my thinking from:

“What did I achieve this week?”

to

“How can I create more impact next week?”

That is where the real value appeared.

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The Prompt

If you want to try it yourself:

Summarise my week in the style of a comedy roast.

Then analyse my week like a CEO reviewing the performance of a business.

Identify:

• My highest ROI activities
• My biggest time wasters
• My recurring work that should become reusable assets
• What only I can do
• What I should stop doing next week

Finally, give me:

• One thing to continue
• One thing to start
• One thing to stop

Be candid, specific and evidence-based. Don’t be nice. Be useful.

Just don’t be surprised when the roast makes you laugh and the follow-up makes you rethink your week.