CIAOPS Need to Know Microsoft 365 Webinar – September

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Now in our tenth year!

Join me for the free monthly CIAOPS Need to Know webinar. Along with all the Microsoft Cloud news we’ll be taking a look at implementing Local AI

Shortly after registering you should receive an automated email from Microsoft Teams confirming your registration, including all the event details as well as a calendar invite.

You can register for the regular monthly webinar here:

September Registrations

(If you are having issues with the above link copy and paste – https://bit.ly/n2k2609)

The details are:

CIAOPS Need to Know Webinar – September 2026
Friday 2nd of October 2026
11.00am – 12.00am Sydney Time

All sessions are recorded and posted to the CIAOPS Youtube channel.

Also feel free at any stage to email me directly via director@ciaops.com with your webinar topic suggestions.

I’d also appreciate you sharing information about this webinar with anyone you feel may benefit from the session and I look forward to seeing you there.

There’s No Such Thing as "Ready"

I’ve lost count of how many times a business owner has told me they’ll bring Copilot in “once we’re ready”. They mean it kindly. They want their data tidy, their policies signed off, their people trained, their SharePoint folders renamed from Final_v3_actual_final. And then they wait. Months pass. The readiness never quite arrives, because readiness isn’t a destination. It’s a story we tell ourselves to justify not starting.

Nobody learns to swim by reading about water. You learn by getting in, going under a little, and coming up knowing something you didn’t know before you got wet.

Confidence Is a Result, Not a Prerequisite

The people I see getting real value from Copilot didn’t feel ready either. They just opened Outlook one busy Tuesday, hit the Copilot button, and asked it to draft a reply to a client email they’d been avoiding. The draft wasn’t perfect. They fixed it. Next time it was faster. That small, slightly awkward first attempt taught them more than any rollout plan ever could.

Waiting to feel confident before you start gets the order backwards. Confidence is what you earn after you’ve fumbled through the first few goes. Ask Copilot in Teams to summarise a meeting you half-missed, and yes, the first summary might skate over the thing that actually mattered. So you learn to prompt it better. That’s not failure. That’s the lesson doing its job.

Small Goes Under, Not a Deep End

Drowning a little every day doesn’t mean throwing your team off the boat. It means deliberate, survivable exposure. Pick one repetitive task this week and hand it to Copilot. Draft the weekly client update in Word. Ask Copilot in Excel to explain what’s driving the number in a spreadsheet you inherited and never fully understood. Have it pull the three key points out of a forty-message channel in Teams before your Monday catch-up.

None of these are bet-the-business moments. Each one is a small go under the surface. Some will work beautifully and some will come back wrong — and the wrong ones are where the real learning lives, because they teach you where the tool’s edges are and where your own judgement still has to sit on top.

The businesses that stall are the ones treating adoption like a single, perfect dive that has to be flawless. The ones that get somewhere treat it like laps. A bit every day. Slightly uncomfortable. Steadily better.

The Water Was Never Going to Be Warm

Here’s the part nobody wants to hear: it never feels comfortable at the start, and that discomfort is not a signal to wait. It’s the signal you’ve finally begun. The team that’s “not ready” but using Copilot daily is six months ahead of the team that’s still perfecting its readiness checklist — because they’ve been quietly getting better the whole time the other one was preparing.

You don’t need clean data to draft an email. You don’t need a governance framework to summarise a document. You need a task, a first attempt, and the willingness to be a bit rubbish at it for a week.

What I’m watching now is how quickly the gap widens between the businesses that started imperfectly and the ones still waiting to feel ready. My honest read? The water’s fine. Get in.

You’ll Likely Fail… and That’s Okay

A few weeks ago I sat with a business owner who’d been quietly avoiding Copilot for months. Not because he doubted it — because he was worried he’d look foolish in front of his own team. He’d typed one clumsy prompt, got a mediocre answer, and decided the whole thing wasn’t for him. I told him the honest truth: your first attempt was always going to be a bit rubbish. Mine were too. That’s not the exception. That’s the process.

We’ve built up this strange expectation that new tools should work perfectly the moment we touch them. AI has made it worse, because the demos look so slick. So when reality delivers a bland summary or a reply that misses the mark, people don’t think I need to adjust — they think this doesn’t work. And then they stop.

Getting It Wrong Is the Point

Here’s what I’ve noticed working with people on Copilot. The ones who get value fastest aren’t the smartest or the most technical. They’re the ones willing to look a little silly while they learn. They’ll ask Copilot in Outlook to draft a reply, read it, wince, and then say “no, make it shorter and less formal.” That second and third pass is where the magic actually happens. The first prompt is just you clearing your throat.

I watched someone ask Copilot in Word to pull together a proposal from three older documents. The first version was a mess — it grabbed the wrong figures and buried the point. Instead of giving up, she told it exactly what was wrong. Ninety seconds later she had something genuinely usable. If she’d walked away after attempt one, she’d have told everyone Copilot “couldn’t do proposals.” Instead she’d learned how to steer it.

Small, Low-Stakes Failures

The trick is choosing where you’re allowed to get it wrong. Don’t stake your reputation on a board paper for your first go. Start somewhere forgiving. Ask Copilot in Teams to catch you up on a meeting you missed and see how close it lands. Have it summarise a long email thread in Outlook before you reply. If it’s off, you’ve lost nothing and learned how it thinks. These little experiments cost you a minute and quietly build the instinct you’ll lean on later.

What surprised me most is how quickly that instinct transfers. Once you’ve learned to nudge Copilot in Excel toward the right analysis, you already know how to nudge it in PowerPoint, or in a Loop page, or anywhere else. The skill isn’t the tool. The skill is being comfortable with the first answer not being the final one.

Give Yourself Permission

So I’d offer the same thing I offered that business owner. Give yourself permission to be a beginner again. Expect the early attempts to disappoint you. Treat each poor result as a clue, not a verdict. The people falling behind right now aren’t the ones failing — they’re the ones so afraid of failing that they never start.

I’m watching this play out across dozens of businesses, and the pattern is consistent. Comfort with imperfection is becoming its own competitive advantage. The willingness to fumble, adjust, and try again is quietly separating the people who’ll thrive with these tools from the people who’ll keep waiting for them to be “ready.” They already are. The question is whether you are.

Why GitHub Copilot Doesn’t Belong Inside Microsoft 365 Copilot

The other day I was asked a question that sounds sensible on the surface.

“If GitHub Copilot is so good, why not just build it directly into Microsoft 365 Copilot for everyone?”

At first glance it feels like the logical next step. One Copilot. One interface. One AI assistant for everything.

The more I think about it though, the more I believe that would be a mistake.

The reason comes down to something that AI vendors often overlook. Different people work in very different ways.

A software developer spends their day creating, testing and refining code. A finance manager lives in spreadsheets. A salesperson works across emails, meetings and CRM records. An executive spends much of their time making decisions based on information coming from multiple sources.

Those aren’t variations of the same job. They’re fundamentally different disciplines.

The Context Is More Important Than The AI

What makes GitHub Copilot valuable isn’t simply that it can generate code.

It’s that it understands the environment a developer works within.

It sits inside development tools. It understands repositories. It helps navigate large codebases. It assists with testing, debugging and software creation workflows. The value comes from the context surrounding the AI.

Microsoft 365 Copilot has a completely different context.

When I ask Copilot in Outlook to draft a response, or use Copilot in Teams to summarise a meeting, the AI is working with conversations, documents, calendars and organisational knowledge. It is focused on helping people communicate, collaborate and make decisions.

Trying to merge these two worlds into a single experience risks making both less useful.

A productivity worker doesn’t need a sophisticated coding assistant appearing in every interaction. In the same way, a developer probably doesn’t want meeting summaries and document drafting cluttering up their coding environment.

Specialisation Usually Wins

We’ve seen this pattern before.

Nobody expects Excel to become Visual Studio.

Nobody asks Word to become a network troubleshooting platform.

Microsoft succeeds because its tools are specialised while still working together.

I think AI will follow the same path.

GitHub Copilot should continue evolving as the specialist assistant for software creation. Microsoft 365 Copilot should remain focused on helping knowledge workers get through meetings, emails, documents and decision-making processes faster.

The mistake many organisations make is assuming every AI capability needs to be available to every employee.

In reality, most people only need the capabilities that relate directly to their role.

Adding more functionality doesn’t automatically create more value. Sometimes it just creates more complexity.

The Real Opportunity Is Connection

Where I do see value is in integration.

Imagine a project manager using Microsoft 365 Copilot to prepare for a software review meeting. The assistant could pull summaries of development activity from GitHub.

A developer could use GitHub Copilot to understand changes in a repository while still accessing relevant business context from Microsoft 365.

That’s very different from forcing both experiences into a single product.

The future isn’t one giant AI assistant trying to do everything.

It’s a collection of specialised agents and copilots that share information when necessary while remaining focused on their primary role.

We’re already starting to see this approach emerge across Microsoft’s ecosystem.

Keep The Tool Sharp

One lesson I’ve learned over many years working with Microsoft technologies is that the best tools are usually the ones with a clear purpose.

A hammer becomes less useful once you start turning it into a screwdriver, a saw and a wrench at the same time.

The same principle applies to AI.

GitHub Copilot should remain the coding expert. Microsoft 365 Copilot should remain the productivity expert.

The goal shouldn’t be to squeeze every AI capability into a single interface. The goal should be to put the right assistant in front of the right person at the right time.

That’s where the real productivity gains will come from.

Your Best Marketing Asset May Already Be Sitting in Teams

Most businesses I speak with think content creation starts with a blank page. That is usually the first mistake.

The better starting point is buried in work already being done. A client workshop. A recorded training session. A checklist built to explain something tricky. A Teams meeting where someone finally understood the issue and asked the question every other client is probably thinking as well.

That material may not have been created for marketing. Good. That is often why it works.

Real content comes from real work

I have never been a big fan of content that sounds manufactured. You can usually spot it quickly. It has the right keywords, the right structure, and no pulse.

The content that lands tends to come from delivery. It comes from explaining MFA to a business owner who wants fewer account compromises. It comes from walking a client through why SharePoint permissions matter before Copilot is enabled. It comes from showing someone how to use Outlook and Teams differently so their day is not ruled by the inbox.

Those moments have weight because they are connected to a real problem. If one client needed that explanation, another business owner probably needs it too.

That is where many MSPs and consultants miss the opportunity. They treat training as something that happens once, inside the client relationship, then disappears. I would rather see it as operational proof. It shows how you think, what you believe matters, and how you help people move from confusion to action.

Capture the explanation, not the performance

This does not mean every client session should become a public article. Confidentiality matters. Context matters. Permission matters.

But the lesson can often be separated from the client. The pattern can be reused without exposing the details.

After running a Copilot readiness session, I might open Word and ask Copilot to help turn rough notes into a plain-English outline. Not a finished post. Not something I publish without thinking. Just a starting structure based on what I actually explained.

I might then drop the key points into a private Teams channel, add the questions that came up, and use that as a source of future newsletter topics, blog ideas, short videos, or client conversation starters. SharePoint becomes the library. Teams becomes the capture point. Copilot becomes the drafting assistant. My job is still to apply judgement.

That workflow matters because it keeps content close to reality. You are not guessing what the market wants. You are listening to what clients already needed help understanding.

Proof beats polish

The market is full of polished noise. Everyone can publish more now. AI makes that easier. That also means the value of generic content keeps falling.

What still stands out is evidence of experience.

A session that helped a client understand sensitivity labels is more useful than a vague post about data protection. A walkthrough that helped a leadership team decide how to govern Teams is more useful than another article saying governance is important. A practical explanation of what Copilot can and cannot see in Microsoft 365 is more useful than a broad claim about AI productivity.

The trick is not to turn every client interaction into a campaign. The trick is to notice the teaching moments already happening in the business and preserve them before they vanish.

That may be a few notes after a meeting. It may be a transcript summary. It may be a reusable diagram. It may be a short internal explanation that later becomes external education.

If your clients keep asking similar questions, that is not an interruption. That is your editorial calendar tapping you on the shoulder.

The best content is not always created in a marketing session. Sometimes it is created while you are helping someone understand their business better. Capture that, shape it carefully, and you will sound far more useful than the people still staring at a blank page.

Faster Leads Need Better Proof, Not More Noise

I see many businesses treat new leads like they are already convinced. Someone fills in a form, downloads a guide, books a call, or replies to a post, and the business immediately pushes for the next step.

That is often too early.

Most prospects do not arrive ready to buy. They arrive curious, sceptical, and carrying only a rough idea of the problem. If your follow-up assumes they are already sold, you force the sales conversation to do all the heavy lifting.

The better question is: what must this person see and trust before the sales conversation becomes easy?

Your best marketing is probably already sitting somewhere

In most businesses I work with, the useful material already exists. It is just scattered.

It might be in a proposal that explained the value clearly. It might be in an old webinar where someone answered the awkward question honestly. It might be in a customer onboarding email, a Teams meeting recap, a SharePoint document, or a PowerPoint deck that has been used quietly for years because it works.

The problem is not always content creation. Often, it is content discovery.

This is where Microsoft 365 Copilot becomes very practical. Instead of starting with a blank page and asking for more marketing content, I would start by asking Copilot to help identify patterns across Outlook, Teams, SharePoint, and OneDrive. What questions appear before prospects say yes? Which objections show up in email threads? Which documents get reused because they make the penny drop?

That is not a campaign yet. That is raw intelligence.

Sequence beats storage

Most businesses store useful content. Far fewer guide prospects through it in order.

A new lead does not need every case study, webinar, brochure, and feature sheet at once. That just creates a homework assignment. What they need is a path.

I would be looking for the small set of assets that change how the prospect sees the problem. The explainer that makes the risk obvious. The story that makes the outcome feel achievable. The short video that answers the awkward question. The document that shows the cost of waiting.

Then I would sequence those assets deliberately.

Not as spam. Not as a flood of automated noise. As a guided conversation that helps the prospect become ready faster.

A simple example: a lead comes in after reading a blog about Copilot readiness. Rather than sending them straight to a booking page, I might first send a short note from Outlook with a link to a SharePoint-hosted checklist. A few days later, I might follow with a Teams webinar recording that explains oversharing risk in plain language. Once the prospect has enough context, the consultation feels less like a pitch and more like the next sensible step.

Faster conversion comes from clearer thinking

I am not saying marketing automation fixes everything. It does not.

If the offer is weak, automation helps you annoy people at scale. If the message is vague, more content only increases the confusion. If the business has not done the work to understand buyer doubt, Copilot will not magically invent that understanding for you.

But used properly, Copilot can help you mine what your business already knows. It can surface recurring themes from meetings, summarise prospect questions from email, help reshape a useful document into a sharper follow-up, and keep the process grounded in real conversations rather than marketing theory.

That is the shift I care about.

Conversion is not just about more leads. It is about helping the right people reach belief sooner. The businesses that get better at that will not necessarily publish more. They will guide better.

That is where I would start.

CIAOPS Image comparison page

Every time a new image model from Microsoft becomes available I use the same test prompt to see what the result is and compare that to previous attempts. The last one of these was here:

https://blog.ciaops.com/2026/08/15/new-microsoft-image-model-2/

With new models coming out all the time, the latest is MAI-Image-2.6-Flash available today, I figured a better option going forward is to put them all on a single web page for comparison which I have now done here:

https://directorcia.github.io/Office365/image-comparison.html

You can view all the model results side by side as well compare the selection you want using the selector in the top left.

I’ll keep adding new results using my standard image test prompt and posting the results here to have a reference going forward.

Let me know if you have any other image models I should test and post.

The Inbox Tells the Truth

I have seen this happen more than once. A business owner turns up every day, answers the same messages, attends the same meetings, and wonders why the energy has disappeared. Nothing is technically broken. Clients remain. Invoices still go out. But the work has become something to survive rather than something to shape.

That is usually when people look for a new tool, market, or strategy. Sometimes that is needed. But I reckon there is a smaller test that tells the truth faster.

Look at the last thing you sent.

Not the polished proposal. I mean the ordinary email you sent to a client, supplier, or your own team. If it landed in your inbox from someone else, would you read it properly? Would it make the next step clearer?

If the honest answer is no, that is not just a writing problem. It is a leadership signal.

Your inbox reflects your business

Email is easy to dismiss because it feels routine. That is why it matters. The routine is where culture leaks out.

A vague email usually points to vague thinking. A rushed reply often means no one has stopped to decide what actually matters. A long message that says little normally means the sender is hoping volume will do the work that clarity should have done.

I am not judging that from a distance. I have written plenty of those messages myself. The kind where the subject line is weak, the point arrives too late, and the recipient has to work out what I want.

When that becomes normal, I give away control.

Copilot should challenge the thinking

This is where Microsoft 365 Copilot becomes interesting, but not for the reason many people expect.

The lazy version is to ask Copilot in Outlook to write the email and then send whatever appears. That may save time, but it does not fix the real problem. It can make it worse, because unclear thinking is now wrapped in cleaner sentences.

The better use is to make Copilot test your intent.

Before sending an important reply, ask: what is the decision in this message? What action am I asking for? What could the reader misunderstand? Can this be shorter without becoming blunt?

That is a different relationship with the tool. Copilot is not the ghost-writer. It is the mirror. It helps me see where I have avoided making the point.

The same applies in Teams. If a channel conversation needs ten messages to agree on one next step, the issue is probably not Teams. It is the absence of a clear owner, decision, or sentence.

Small standards rebuild confidence

When a business feels flat, the temptation is to chase a big reset.

Momentum often returns through smaller acts of discipline.

Write the subject line like it matters. Put the decision near the top. Tell people what happens next. Use Copilot to tighten your thinking, not decorate your uncertainty. Move the discussion into Teams when the email thread has become a swamp, then summarise the decision so the next person does not have to excavate it.

That may sound basic. It is. That is the point.

Businesses rarely lose their edge all at once. They drift. Standards slip in small places first. The inbox gets dull. Meetings become foggy. Documents become harder to read. Everyone keeps moving, but fewer people know why.

The way back starts in one ordinary place.

Open your sent items. Read your own work as if you were the client. If it would not earn your attention, fix the standard there.

That is where authority starts to return: with one clearer message, one cleaner decision, and one less piece of work that asks the reader to do your thinking for you.