I have now run 34 modern working assessments for small and medium businesses.

Different industries, different team sizes, different software stacks. Some were two-person operations. One was a 200-person organisation across three continents. Most sit in the middle.

Across all of them, the same five patterns show up before we start changing anything. None are about the software. All are about the agreement underneath the software.

​If you recognise your business in any of these, that's the point.

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The belief I see in almost every business I work with is that the next tool will fix it.

Teams was going to fix everything when it arrived. Then SharePoint Online was going to fix everything. Then Copilot was going to fix everything.

Each time, the same chaos just gets layered into the new tool. New tools layered on top of unclear agreements give you chaos in a shinier box.

I am working with a 100-person organisation right now. They rolled out Copilot to everyone, all at once, with no training and no thought, and without tidying up their files first. They still have chaos inside Copilot, because we have not actually started the implementation work yet. We have only written the report.

I had to write this verbatim. A Copilot licence is not a strategy. If your humans do not know what to do, the AI is not going to know what to do either.

Picture how a single file can move through your business. Janine creates it in OneDrive. She puts a link into a Teams chat, but she shares it the wrong way and the recipient cannot open it. So she creates a different version in the SharePoint site. She links to that, but it sits siloed in a SharePoint site the recipient does not have access to. So she emails it. Now there are two copies.

The recipient saves their copy down, makes some edits, emails it back. There are now four copies, in four places, with no obvious answer to "what's the latest?"

If you ask Copilot for the latest version of that file, what is it going to look at? The version on the recipient's desktop? The version emailed back? The version in OneDrive? The version in SharePoint?

Copilot will guess. And it will guess wrong, because the structure underneath is broken.

The work that has to happen first is not technical. It is human. We have to make the organisation work for humans. Then everything else can work on top.

The simplest possible way to work together. Agree to it. Stick to it. One way of doing things, no more.

If you are about to send a file, ask a question, or get something off someone, and you have to think "I do not know if it goes here or there" — that is the work failing in real time. Sort that out first, and any new tool that arrives will land on solid ground.
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The perfect structure, the right workshops, the best guidance — none of it survives if the leadership does not visibly sponsor the work.

I once ran a modern working assessment for a 200-person company. Loads of workshops across the business. The chief executive did not attend a single one.

Not one.

In the report, I had to write this verbatim. "If the CEO does not attend a session designed to understand how the company works, the implicit message, however unintentional, is that this work is optional. That signal travels fast in an organisation of 200 people. No change initiative survives a culture where the leadership does not visibly sponsor it."

In that specific case, my recommendation was to not do anything. There were bigger fish to fry. The priorities were not aligned. There was no point trying to change how everyone worked internally because there was always more chaos being introduced from above.

That is fine if that is where the business is. But do not shoehorn an organisation-wide change project on top of it.

I have also turned down work entirely after a discovery call where it was clear the CEO did not care how their people worked together. If the chief executive does not care, neither does anyone else.

You do not need to be the expert in the room as a leader. You need to be the sponsor. Show up visibly. Show up consistently. Do the doing, do not delegate the belief.

If you are reading this as the owner thinking "my team won't change," the honest question is whether they have seen you change first.

The CEO sets tone. Managers carry it.

There is a layer between the leadership and the people doing the work every day. These are the people who decide whether a new habit survives or dies.

Picture a river. The leadership clears the source. But there is a dam halfway down. Nothing flows to the people who need it.

I have seen this across dozens of businesses. Same tools, same setups, same training. One team thrives because their manager posts in the channel every Monday. The team next door uses email because their manager uses email. Same business, same week.

Nobody is going to go against the preferences of their immediate boss. They mirror what they see in front of them.

So channels that get used by managers stay used. Channels that get left by managers end up dead.

If a manager is not showing up in the agreed way of working, neither is their team.

This is where most rollouts quietly fail. The leadership has signed off. The tools are configured. The training has been delivered. But the middle layer never gets the same conversation about their own habits. So they keep working the way they always have, and their teams keep mirroring them, and the rollout fades.

The fix is to have a specific habits conversation with managers, before go-live. Not a strategy session. A practical walk-through of the moments in their week where the old habit will reassert itself, and what to do instead.
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Nobody wakes up in the morning and decides to make information impossible to find.

I have now done over 30 of these assessments and every one shows the same pattern before we start to implement.

In one report, I wrote that no two teams in the same company described the same approach to any internal collaboration. Another 200-person business, across three continents, had the Australian team running on its own SharePoint site that the rest of the business never touched. The US team was doing its own thing, even though their work was very similar to the UK team's work and they would have benefited massively from seeing what each other was doing.

Nobody created those silos deliberately to exclude people. Nobody is hoarding information on purpose. It is just what happens when you do not agree on the alternative.

Human nature is to work in small groups. Even with good intent, nobody builds an organisation-wide system by accident. Every time someone saves a file to their own space, every time a decision happens in a meeting and never gets written down, every time a conversation stays in a private chat instead of a channel, it is a brick going up in a wall.

So here is the truth most businesses miss. Silos are the default state. They are not a deviation from the norm. They are the norm.

To fix it means having a simple, well-designed, demonstrably better, open way of working. Then deciding where things live before people decide for themselves. Then changing the culture so that it persists without ongoing effort.

Without that, you get ten teams with ten different systems and nobody can find anything.

This is what the What Goes Where Agreement is for. One page. Where files live, where tasks go, where chat happens, where announcements go, what gets put in email. Agreed by everyone. Applied to everyone, including the senior leadership team.
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When silos take hold and information is scattered, one thing fills the gap. You already know what it is.

Imagine a kitchen with no labels on the cupboards. Every time someone needs a plate, they open three doors before they find one. Eventually they just ask the person standing closest. "Where are the plates?"

That is a meeting.

Now imagine every cupboard has a label. Plates here. Glasses there. Cutlery in that drawer. Nobody asks. Nobody gets interrupted. Everyone gets on with it.

Your business is the same. If updates live in a known place, you do not need a meeting to share them. If ownership is clear, you do not need a meeting to ask. If the way you communicate is agreed, you do not need a meeting to make sure people heard you.

Underneath every meeting are the same three things. Where things live. Who owns what. How you communicate.

Agree those, and half your meetings dissolve on their own. Not because meetings are bad. Because most of them only exist to fill a gap that should not be there in 2026.
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If you are reading this and recognising your business, you have two options.

The first is to fix it yourself. The full method is written down in the Chaos Cure. It is a self-guided playbook plus workbook. The whole MeeTime Method, written down for the first time, for businesses that want to fix this without paying for a consultant.

The second is to talk it through with someone. If your situation is more complicated, or you want a hand mapping it to your specific business, that is what a discovery call is for.

Either way, the first move is to stop waiting for the next tool. There is no tool coming that will save you from the chaos you have installed.

You can read the deeper blog post on how to structure Microsoft Teams for a small business here — that is the practical first step for fixing pattern four.
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Why doesn't Microsoft Copilot fix Microsoft 365 chaos?
Because Copilot needs structure to work well. If your files, conversations and decisions are scattered across personal drives, private chats and unagreed Teams channels, Copilot will guess what to surface and guess wrong. A Copilot licence is not a strategy. The structure has to come first.

What is a modern working assessment?
A structured review of how a business actually works inside Microsoft 365, mapped against a target operating model. It surfaces the gaps between intended working practice and real-world habits, then produces specific recommendations grouped under the MeeTime Method (Working Out In The Open, Getting Things Done, Community).

Why do most Microsoft 365 rollouts fail at the middle management layer?
Because the status quo is set by whoever is closest to a person, not whoever is highest above them. If a manager keeps using email, their team keeps using email, regardless of what the training said. Most rollouts skip the specific habits conversation with the manager layer, so the new way fades.

What is the What Goes Where Agreement?
A one-page document agreed across the whole organisation that names where each type of work happens. Files in SharePoint. Tasks in Planner. Real-time discussion in chat. Permanent updates in channels. It is the simplest possible answer to the question "where does this go?" so that nobody has to think about it twice.

Why are silos the default state in organisations?
Because human nature is to work in small groups, and nobody builds an organisation-wide system by accident. Without an explicit, well-designed alternative, people will quietly invent their own ways of working. The fix is to design the open way deliberately and make it the easier path.
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