The Content That Changes What You Want

For years I measured a good session by how much I crammed into it. Steps, screenshots, settings, the lot. If someone walked out with a longer to-do list than they arrived with, I’d done my job. I don’t see it that way anymore.

The shift happened quietly. I started noticing that the sessions people remembered weren’t the ones where I taught the most. They were the ones where something clicked and a person suddenly wanted to work differently. The instruction was almost beside the point. What stuck was the wanting.

Knowing how isn’t the same as wanting to

You can show someone exactly how to do a thing and watch them never do it. We’ve all run that webinar. The hands-on steps are perfect, the recording goes up, and three weeks later nothing has changed in their business. The knowledge landed. The desire never did.

I see this constantly with Microsoft 365 Copilot. I can demonstrate how to summarise a long thread in Outlook, how to pull the action items out of a Teams meeting, how to draft a first version of a proposal in Word. People nod. They get it. But the ones who actually change are the ones who leave thinking, “I never want to scroll through forty unread emails by hand again.” That sentence isn’t instruction. It’s appetite. And appetite is what does the work after the session ends.

The job is to make the better way feel obvious

So now, when I’m putting together a workshop or a video or even a short email to a client, I’m not really asking what I should teach. I’m asking what I want them to start wanting once it’s over.

That changes how I build the thing. Instead of opening with a feature, I open with a moment they recognise — the Friday afternoon spent rebuilding a status report they’ve already written four times this month. Then I show Copilot pulling that report together from the documents already sitting in their SharePoint, in about a minute. I’m not listing what it can do. I’m letting them feel the gap between how they work now and how they could. Close that gap in front of someone and they don’t need convincing. They’ve already decided.

The same logic runs through everything I put out. A YouTube clip, a Loop page I share with a patron group, a single line in a newsletter — they all work better when they leave a person slightly dissatisfied with their current way of doing things, in the best possible sense.

What I’m watching now

The tooling has never been easier to demonstrate. Copilot will happily show off. The harder, more interesting question is whether the content around it makes anyone actually want a different working life.

That’s the part I keep returning to. Teaching the steps is the easy half. Teaching someone to want the outcome — that’s where the real change starts, and it’s the bit I’m still learning to do better.

The AI question worth sitting with

A while back, over coffee, someone asked me which clever AI trick had impressed me most this year. I disappointed them. The thing that stuck with me wasn’t a trick at all. It was a question I now ask myself most afternoons: of everything I did today, how much of it didn’t actually need me?

It’s an uncomfortable question, and it should be. Sit with it long enough and you start noticing how much of your week is just movement — chasing the same status update, rewriting the same kind of email, copying numbers from one place to another. Honest work, sure. But not the work only you can do.

The instinct to hold on

Most people, when they feel AI getting close to their job, pull their work in tighter. They guard it. They want to prove the human bit still matters. I understand the reflex, but I think it’s backwards. The value was never in the doing. It was in knowing what was worth doing in the first place.

The people I admire most are doing the opposite. They’re hunting for things to hand over. They treat every repetitive task as a candidate for handover, not a badge of how busy they are. When a reply lands that says the same thing they’ve written forty times, they don’t write it again — they ask Copilot in Outlook to draft it and spend their attention on the one paragraph that’s genuinely new. When a long Teams thread needs catching up on, they let Copilot summarise it and read the summary, not the forty messages.

That’s not laziness. That’s deciding where your judgement is actually worth spending. Every hour you claw back from the routine is an hour you can point at something that actually moves the business.

Hand it over once, properly

Here’s the part most people miss, though. Handing a task to AI once is a parlour trick. The real shift happens when you stop doing the task and start building the thing that does the task.

I’ve watched a business owner take the monthly client report — the one that ate a Friday afternoon every month — and rebuild it as a flow. Power Automate pulls the numbers, Copilot drafts the commentary in the same tone she’d use, and the whole thing lands in a SharePoint folder before she’s had her second coffee. She doesn’t make the report any more. She looks after the thing that makes the report.

And that’s the bit worth understanding. Once the work runs on its own, your job changes. You’re no longer the one producing the output — you’re the one watching the machine that produces it, and adjusting it when it drifts. When the tone goes a bit flat, you fix the instructions, not the document. When the numbers look off, you check the flow, not the spreadsheet. Your effort moves up a level.

That’s where the real return sits. Not in doing the task faster. In stepping back from the task entirely and tending the system instead.

What I’m watching now

None of this happens by accident. It takes a deliberate habit of asking, over and over, what you did yesterday that you shouldn’t be doing tomorrow. Most people never ask. They’re too busy doing. And the irony is the busier you are, the more of your day is probably the kind of work you could give away.

So I’ll leave you with the same uncomfortable question. Look back at yesterday. Find the hour a machine could have run without you. Then go and build the thing that runs it — and free yourself up for the work that actually needs a human in the chair.

Stop Holding People Accountable. Start Building Momentum.

There’s a conversation I’ve watched play out a hundred times, and it always goes the same way. Someone agreed last week to get a thing done. This week, they didn’t. So the check-in begins. Did you finish it? No. Why not? And then comes the explanation — the kids were sick, a client blew up, the week got away from them. By the end they feel small, the task gets shuffled forward, and everyone agrees to try again next time.

Then we run it back. Same script, same shrinking feeling. And here’s the part nobody admits out loud: the simplest way to make that bad feeling stop is to walk away from the whole arrangement entirely. People don’t quit because they’ve failed. They quit because the relationship has quietly become a source of guilt.

I see this with MSP owners constantly. They build accountability structures for their teams, their clients, even themselves — weekly stand-ups, status trackers, a long list of overdue commitments staring back at them. And the structure, the thing meant to drive progress, becomes the thing people learn to dread.

Accountability is a low ceiling

The uncomfortable truth is that accountability only works on people who don’t really need it — and even then, only for a while. It’s a tool built around the assumption that someone has to be watched or they’ll drift. Chase the high performers in your business with that energy and watch how fast they disengage. The good ones already hold themselves to a higher standard than you ever could. They don’t want a minder checking their homework. They want to get somewhere, faster.

So I stopped asking whether things got done. When I sit down with someone now — whether it’s a one-week review or a full six-week stretch — I ask two questions only. What went well? And what did this teach you? That’s it. Everything else from the past is noise. The misses, the excuses, the guilt — none of it moves you an inch forward. The wins tell you what to repeat. The lessons tell you what to change. The rest is dead weight you’re dragging into next week for no reason.

From rear-view to road ahead

Once those two things are on the table, the conversation flips direction. We’re no longer auditing the past — we’re using it. We find the one obstacle actually slowing the person down, we clear it out of the path, and we decide the very next move. Look back only long enough to learn, then point everything forward.

This is where the tooling matters more than people expect, because most of the friction that kills momentum is small, dumb, and repeatable. Someone “forgot” to follow up because the note lived in their head instead of anywhere useful. A commitment vanished because it was never written down where the team could see it. That’s not a discipline problem. That’s a system problem, and systems are fixable.

Inside Microsoft 365, this gets a lot easier. When I close out a planning session in Teams, I’ll ask Copilot to pull the wins and the agreed next moves straight out of the meeting transcript, so nobody’s relying on memory by Friday. The actual commitments go into Planner as real tasks with owners and dates — visible, shared, alive — not buried in someone’s inbox. A Loop component pinned in the channel becomes the running scoreboard the whole team can glance at. And first thing in the morning, Copilot in Outlook surfaces what’s drifted and what’s due, so the next move is obvious before the day even starts. None of that is about catching people out. It’s about removing the friction that quietly steals forward motion.

Speed, not surveillance

This is the shift I’d put to any MSP leader still running their team on guilt. The higher someone performs, the less they need policing and the more they crave progress. So give them progress. Clear the road, name the next step, and get out of the way. Momentum compounds — one clean win makes the next one easier, and before long the person isn’t being pushed at all. They’re pulling.

If what you want is someone standing over your shoulder reminding you of everything you haven’t done yet, I’m honestly not the right person for that. But if you want the obstacles gone, the path clear, and the next move obvious so you can win quicker — that’s the whole job. Stop counting what’s overdue. Start building what’s next.

AI Doesn’t Care About Your MSP Business Model

I’ve been thinking about a question that might make some MSPs uncomfortable.

Should the next technology revolution be guided by the same people who have spent the last twenty years building businesses that depend on things staying exactly the way they are?

That sounds harsh, but hear me out.

Every major technology shift creates winners and losers. Cloud changed the value of servers. Microsoft 365 changed the value of maintaining Exchange on-premises. Remote monitoring and management changed the need for technicians driving between customer sites. AI is now doing the same thing to knowledge work.

Yet when I talk to some MSPs about AI, I often hear the same response.

“It’s not ready.”

“Our clients aren’t asking for it.”

“We’ll wait and see.”

“They still need us to do the basics.”

Maybe. But that’s exactly what people said about cloud computing.

The Incentive Problem

The challenge isn’t that MSPs don’t understand technology. Most understand it very well.

The challenge is incentives.

If you’ve built a successful business around selling licences, managing devices, responding to support tickets and charging for technical expertise, then AI creates a problem. The more capable AI becomes, the more it starts consuming activities that have traditionally generated revenue.

If a Microsoft 365 Copilot prompt can analyse a meeting, draft a proposal and create an action plan in minutes, what happens to the hours previously spent doing that work?

If an AI agent can resolve basic support requests, summarise conversations and retrieve information from SharePoint or Teams, what happens to the service model built around handling those requests?

It’s understandable that some MSPs look at this and feel uncomfortable.

But technology has never cared about existing business models.

History Doesn’t Reward Defenders

I’ve seen this pattern before.

Businesses often spend more energy trying to protect the old revenue stream than understanding the new opportunity. They look at disruption as something to resist rather than something to harness.

The problem is that customers rarely share that loyalty to the old model.

Business owners don’t wake up in the morning hoping to buy more support hours. They want outcomes. They want faster decisions. They want less administration. They want their staff spending more time serving customers and less time managing information.

Today, a growing number of those outcomes can be delivered through AI.

Whether MSPs like it or not.

The Risk of Becoming the Blocker

One of the dangers for traditional MSPs is becoming the organisation that says no.

No, you shouldn’t use AI yet.

No, you shouldn’t change your process.

No, your existing approach is good enough.

Meanwhile, another adviser walks in and shows the client how Microsoft 365 Copilot can reduce the time spent preparing for meetings in Teams, drafting emails in Outlook and analysing information in Excel.

Guess which adviser the client sees as helping them move forward?

I’ve always believed that our role as technology professionals is not to preserve the status quo. It’s to help customers navigate change safely and effectively.

That doesn’t mean blindly embracing every new feature that appears. Governance still matters. Security still matters. Data quality still matters. AI without preparation can create as many problems as it solves.

But that’s very different from pretending the change isn’t happening.

The MSP Opportunity

Ironically, AI may create one of the biggest opportunities MSPs have seen in years.

Most businesses have no idea how to prepare their data, secure their environment or establish the governance needed to use AI safely. They need guidance. They need strategy. They need trusted advisers.

That’s where MSPs can create enormous value.

But only if they’re willing to evolve.

The conversation can’t stay focused on devices, licences and tickets. It needs to move towards business processes, information management, knowledge discovery and AI readiness.

That’s where the real opportunity sits.

Final Thoughts

I don’t think AI should be entrusted solely to old-school MSPs who want everything to stay the same. Equally, I don’t think businesses should rush headlong into AI without experienced technology advisers.

The answer lies somewhere in the middle.

The MSPs that thrive over the next decade won’t be the ones defending the past. They’ll be the ones helping clients prepare for the future.

Because AI isn’t interested in protecting anyone’s business model.

It’s simply moving forward.

And the question every MSP needs to answer is whether they’ll be leading that change or explaining to clients why they missed it.

The Hard Part Isn’t Adding Anymore

I caught myself last week with eleven browser tabs open, three half-built automations, a new Planner board nobody asked for, and a Teams channel I’d spun up that morning and already forgotten the purpose of. None of it was hard to create. That was the problem. Every one of those things took me about ninety seconds, and ninety seconds is now the entire cost of bringing something new into existence.

For most of my working life, the brake on doing more was effort. You wanted a new report, a new process, a new client deliverable — and the friction of actually building it slowed you down enough to ask whether it was worth it. That friction is mostly gone. Copilot drafts the document, the deck, the email sequence. Power Automate wires the workflow. The wall that used to stop me from acting on every passing idea has quietly come down.

Speed without judgement is just mess

I’ll be honest about the wiring in my own head. I’m wired to react. A thought lands, I want to act on it immediately, and for years that instinct ran straight into the resistance of having to do the work by hand. The work was the filter. It forced a pause.

Now there’s no pause. The reaction and the execution have collapsed into the same moment. I think “we should have a dashboard for that” and Copilot in Excel has one in front of me before the idea’s even finished forming. Multiply that across a week and you don’t get a sharper business. You get a cluttered one. More dashboards nobody reads. More channels nobody checks. More automations quietly firing into inboxes that have stopped paying attention.

The skill that used to matter was production — the ability to make the thing. That’s not scarce anymore. Anyone with a Copilot licence can produce. What’s scarce now is the judgement to know which of the ten things you could build is the one that actually matters, and the discipline to let the other nine die.

Taste is the work now

I keep coming back to the word taste, because I can’t find a better one. It’s the ability to look at everything you’re capable of generating and recognise what’s worth keeping. It’s hearing the difference between a real signal and noise dressed up to look like progress. And it’s having the spine to cut — to delete the document, kill the channel, switch off the automation — even though it cost you almost nothing to make and feels wasteful to throw away.

This is uncomfortable, especially for those of us who measure ourselves by output. Cutting feels like the opposite of productivity. But a business that adds endlessly and never subtracts doesn’t get faster. It gets heavier. Every new thing you create has a maintenance cost, an attention cost, a “what was this for again?” cost that lands months later. The Loop pages multiply. The SharePoint sites pile up. The thing you built in ninety seconds takes a year to quietly rot in front of everyone.

So I’ve started running my week the other way around. Instead of asking Copilot what else I could build, I ask it what I should stop. I’ll point it at a Teams channel and ask for a summary of the last month — and if the honest answer is “three automated posts and no human replies,” that’s my cue to shut it down. I use Copilot to find the dead weight, not just to make more.

The momentum problem

Here’s the part I want to be straight about, because it’s where I think a lot of us are stuck. You can feel that your best work is still in front of you. The ambition is real. But the momentum you’re chasing won’t arrive while the business is carrying this much weight. Every unfinished idea, every half-used tool, every process you bolted on and never removed is drag. You can’t accelerate something this loaded, no matter how fast you’re able to add to it.

The temptation, when you feel slow, is to add more — a new tool, a new system, a new initiative to fix the sluggishness. That instinct is exactly backwards. The way through isn’t more production. It’s subtraction. The lightness comes from what you’re willing to remove.

It’s never been easier to make something. Which means the rare, valuable, genuinely hard skill is no longer making — it’s choosing. Less, but the right less. That’s the whole game now.

GAIN: Knowing What to Hand to AI and What to Hold Onto

A while back I caught myself spending a Saturday morning copying figures into a spreadsheet by hand. Forty minutes in, it landed on me — Copilot could have done this while I made a coffee. I wasn’t being thorough. I was being slow. And when the person at the top moves slowly, everything behind them backs up too.

That morning is why I keep coming back to a simple way of sorting the work in front of me: what to pass over, what to speed up, what to build alongside the machine, and what I should never let go of. Four buckets. GAIN.

Pass over the work that doesn’t need you

Most of us hold on to tasks out of pure habit. The first draft. The long document that needs boiling down. The background reading before a client call. None of that needs your judgement — it just needs doing. So let it be done. I’ll ask Copilot in Word to condense a forty-page proposal, or have it pull the recurring themes out of a month of client emails in Outlook. I’m not after ideas. I’m after a finished job. Once you start looking, the size of this pile is genuinely surprising.

Speed up the things that already work

Every business runs on small, repeatable steps. An enquiry arrives, someone qualifies it, someone books the meeting, someone sends the follow-up. You’re not reinventing that — you’re stripping out the waiting in between. With Power Automate sitting under Copilot, a new lead can be sorted, routed, and have a meeting request out the door before anyone’s even read it. Two hours back a week, every week, for as long as the doors are open. That compounds in a way that’s easy to dismiss when you’re staring at the setup.

Build something you couldn’t make alone

This is the part people skip past. The real value isn’t AI standing in for you — it’s the two of you producing something neither would on its own. I’ll have Copilot take ideas I’ve already worked through, connect them in ways I hadn’t spotted, and hand them back in a different shape. Sometimes I’ll drop a Loop page of rough notes and let it pull the thread together while I’m out of the office. I come back and I’m editing, not starting from a blank page. Minutes of shaping instead of hours of grinding. You shift from making the thing to sharpening it — and that’s a far better use of your attention.

Keep what only you can do

Not everything belongs on these piles, and pretending otherwise is how people lose the plot. Taste can’t be handed over — it’s learned, never taught, and certainly never prompted. Vision stays yours, because the machine has no idea what your clients will want next year. And care — actually feeling something for the work and the people on the other end of it — that’s the whole point of doing any of this. Copilot can draft the message; it can’t mean it. Guard those three closely.

The aim was never to turn yourself into the software. It’s to clear away everything else so there’s more room for the part of the job that’s unmistakably yours. I’m curious how far that line shifts over the next year — but those last few things, I don’t think they move at all.

Is Microsoft Losing Its Memory?

Over the last few weeks I’ve had more than a few conversations that have nothing to do with technology and everything to do with people.

The topic? Microsoft.

Not the products. Not Copilot. Not Azure. The company itself.

With another round of layoffs and a steady stream of experienced employees announcing their departure, many people are starting to ask the same question: Is Microsoft becoming a completely different company? And if so, is that a good thing?

It’s a fair question because a lot of the people leaving aren’t newcomers. They’re the people who have spent years, sometimes decades, building products, relationships, culture and institutional knowledge. They know why certain decisions were made. They remember what worked, what failed, and what lessons were learned along the way.

When that experience walks out the door, something goes with it.

Every Generation Reinvents the Company

One thing I’ve learned from watching Microsoft over many years is that the company is constantly reinventing itself.

The Microsoft that built Windows isn’t the same Microsoft that built Azure.

The Microsoft that created Office isn’t the same Microsoft that now delivers Microsoft 365.

And the Microsoft that is investing heavily in Copilot and AI today is once again becoming something different.

In many ways that’s exactly why the company has survived when so many technology giants have faded away. It has shown an ability to change direction when the market changes.

The challenge is that reinvention often comes with a cost. New people bring new ideas, new priorities and new ways of working. That’s healthy. But if too much historical knowledge disappears at the same time, organisations can find themselves solving problems that were already solved years ago.

Sometimes experience isn’t about knowing what to build. It’s about knowing what not to build.

The Hidden Value of Institutional Knowledge

When people think about layoffs, they often focus on roles and headcount.

What doesn’t get measured so easily is context.

Every organisation has unwritten knowledge. The things that never make it into documentation. The conversations that explain why a process exists. The lessons learned after a customer escalation. The accumulated understanding of how products, teams and markets really work.

Ironically, this is exactly what many businesses are now trying to capture with AI.

When organisations deploy Microsoft 365 Copilot, one of the first discoveries is that their knowledge is scattered everywhere. Some of it lives in SharePoint. Some is hidden in Teams conversations. Some is trapped inside Outlook mailboxes. And some only exists inside the heads of experienced employees.

When those employees leave, that knowledge often leaves with them.

That’s why I believe one of the greatest values of Microsoft 365 isn’t just productivity. It’s preserving organisational memory. Every Teams meeting transcript, every shared document, every Copilot-assisted summary creates a record that can help future employees understand the context behind decisions.

Technology can help capture knowledge, but it can’t replace the judgement that created it in the first place.

Could This Actually Make Microsoft Stronger?

The other side of the argument is equally compelling.

Large organisations can become attached to the way things have always been done. Fresh perspectives can challenge assumptions. New leaders can move faster because they’re not carrying the weight of past decisions.

You can certainly argue that Microsoft’s rapid shift towards cloud computing and now AI required new thinking that may have been difficult inside a company built around legacy business models.

A business that never changes eventually becomes irrelevant.

The risk isn’t change itself. The risk is changing so quickly that you forget what made you successful in the first place.

There’s a balance to be found between respecting experience and embracing new ideas.

What I’ll Be Watching

As Microsoft pushes deeper into the AI era, I think the real test won’t be how many people leave or how many new people join.

The test will be whether the company can preserve the culture, engineering discipline and customer focus that helped build its reputation while simultaneously creating something new.

Most successful organisations stand on two foundations: experience and innovation.

Lose innovation and you fall behind.

Lose experience and you repeat old mistakes.

The companies that thrive find a way to keep both.

Microsoft has reinvented itself many times before. The question now is whether this latest transformation strengthens the foundations of the company or slowly erodes the knowledge that helped make it one of the most influential technology organisations in the world.

Creating a Digital Twin of Your Business

When most people hear “digital twin”, they picture an engineer running a virtual copy of a jet engine, or watching a simulated factory floor hum along on a screen. It sounds like something built for heavy industry, a long way from a business that runs on email, spreadsheets and the occasional frantic search through old files. I’ve come to think the idea fits an ordinary organisation just as well — and that most of us are far closer to having one than we’d assume. The raw material is already sitting there. We’ve just never thought of it in those terms.

A digital twin of a business isn’t a 3D model. It’s a living representation of how your organisation actually thinks: the decisions it has made, the reasons behind them, the way a job quietly moves from one person to the next. That knowledge already exists. The problem is that it’s scattered. Some of it sits in SharePoint, some in a Teams thread nobody has opened in a year, some buried in a colleague’s sent items — and an uncomfortable amount lives only inside one person’s head.

You already own the knowledge

A while back I watched someone spend half a morning answering a question their business had already answered twice. The work existed. It simply couldn’t be found quickly enough, so they built it again from nothing. That’s the everyday cost of not having a twin you can talk to. You’re not short of information. You’re short of a way to ask your own business what it already knows.

This is where Copilot starts to shift things. Connected across your Microsoft 365 tenant, it lets you put a question in plain language and pulls the thread together for you. Ask why a particular client moved onto a different plan, and Copilot can surface the Outlook email where it was decided, the meeting where it was thrashed out, and the document that recorded the outcome. A new staff member can ask it how something is normally done and get an answer drawn from real history, not folklore. You stop hunting for a file and start interrogating your own past.

The twin is only as good as what you feed it

This is where most businesses come undone. If a decision gets made on a phone call and never written down, the twin can’t see it. If the reasoning lives only in someone’s memory, it isn’t in the model. So the habit worth building is unglamorous but powerful: put decisions somewhere Copilot can reach. Keep the Teams meeting recap instead of letting it disappear. Write the why into the document, not just the what. Treat a SharePoint page or a Loop component as the place your thinking genuinely lives, rather than a tidy-up job for later.

None of that is technical work. It’s a discipline — choosing to treat your own knowledge as something worth keeping, instead of something you’ll cobble back together under pressure when you next need it.

What it actually buys you

I don’t think the goal is a perfect replica. No model captures everything, and you wouldn’t want one that tried. But a business that can answer its own questions — one that remembers why it did things — moves faster and argues less. It brings new people up to speed sooner. It stops relitigating decisions that were settled months ago.

The pieces are already sitting in your tenant, waiting to be connected. What I’m watching now is which businesses bother to feed the twin, and which keep solving the same problem every Tuesday morning, none the wiser for having solved it before.