Author: directorcia

Director or Doer? The AI Question Nobody’s Asking

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Most of the AI conversations I have these days start the same way. Someone leans in and quietly asks, “Do you think AI is going to take my job?” I understand the worry — it’s everywhere, and it’s loud. But I think it’s the wrong question. The one worth asking is sharper and far more uncomfortable. Are you using AI, or is AI using you? That single reframing changes the whole game. And the window to land on the right side of it is narrowing faster than most people realise.

The Doer Trap

I see the Doer pattern everywhere. Someone types a rushed prompt, reads whatever comes back, tidies up a comma or two, and ships it. The email goes out. The deck gets shared. The summary lands in a meeting. The person feels productive because something got done — but they didn’t really direct any of it. The tool picked the angle, the structure, the tone, even the conclusion. They just drove the delivery truck.

The thing that makes this dangerous is that it feels like progress. Output is going up. Calendars are clearing. But the thinking is going down. The muscles that matter — judgement, taste, point of view — quietly shrink while everyone is busy celebrating how much faster the work moves. If AI is setting the pace, choosing the framing, and deciding what “good” looks like, you are no longer in charge of your own work. You are assisting it.

The Director Shift

The people I watch pulling away from the pack work very differently. They treat AI the way a good manager treats a capable team. They brief it properly. They tell it the audience, the constraint, the outcome they want, and what to leave out. They read the output the way an editor reads a draft — with scepticism, not relief. They push back. They ask it to try a sharper angle, to argue the opposite, to shorten by half. They know what great looks like before they ask for it, and they recognise when the answer is merely adequate.

Being the Director is harder. It takes domain knowledge, taste, and the patience to iterate. But the work that comes out the other side is genuinely yours. The ideas are yours, the standards are yours, the reasoning is yours. AI is doing the heavy lifting on the mechanics while you do the heavy lifting on the thinking. That’s the right shape of the partnership.

The Window Is Closing

Here’s what I think people underestimate. The gap between Directors and Doers is compounding. Every week spent actively learning how to brief, evaluate, and steer these tools is a week of skill you’re banking. Every week spent passively accepting output is a week of skill you’re quietly losing. Six months from now, a year from now, that gap will be visible from across the room — in the quality of decisions, the confidence of arguments, the crispness of output.

The people who dig in now, who actually invest the hours to learn this properly, aren’t just getting better at AI. They’re becoming more valuable than they were before AI existed. Their judgement is sharper. Their output is broader. Their leverage is higher. The people waiting for it to settle down are going to wake up behind, and it will take a lot more than a weekend of prompting tutorials to catch up.

So I’d stop asking whether AI is coming for your job. Ask instead who’s running whose day. Because that answer — today, this week, this month — is the one that decides where you end up.

Driver & firmware update management via Intune

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Walk into most MSP-managed Windows fleets and the update story stops at quality and feature rings.

Drivers? “Windows Update grabs those.” Firmware? “The OEM utility does that.”

That’s not a strategy. That’s three different cooks in the same kitchen, and you’re praying none of them serves up a bad BIOS on a Friday afternoon.

Here’s the real win. Intune has had a dedicated approval surface for driver and firmware updates for a while now. And almost nobody’s switched it on.

What is a driver update policy, really?

It’s a separate Intune profile that sits alongside your existing update rings. It shows you every driver and firmware update Windows Update has queued for your managed devices, and lets you decide — one at a time — whether to ship it.

Approve, pause, defer, hold back the one dodgy NIC driver while the rest go through. All in the portal.

Critically, it’s the same pipeline Windows Autopatch uses for drivers. Five-laptop accounting firm on Business Premium or 500-seat shop on M365 E3 — same surface. You need Intune Plan 1 and a Windows licence that includes the Autopatch entitlement (Business Premium and M365 E3/E5 both have it), devices must be Entra joined or Entra hybrid joined, and telemetry must be set to Required or higher. That’s the lot.

Step-by-Step: switching it on
Check your existing rings aren’t blocking drivers

This is the bit that catches people. If your existing Update Ring or Settings Catalog policy blocks drivers, the whole feature does nothing. In your update ring, set Windows driver to Allow. In the Settings Catalog, set Exclude WU Drivers in Quality Update to Allow Windows Update drivers.

Both default to Allow, but I’ve found plenty of older tenants where someone clicked Block years ago and forgot.

Open the right blade

Sign in to the Microsoft Intune admin centre → Devices → By platform → Windows → Manage updates → Windows 10 and later updates → Driver updates tab → Create profile.

Pick an approval mode

You get two:

  • Automatically approve all recommended driver updates — anything the OEM tags “recommended” gets approved on its own, with a deferral you set between 0 and 30 days.

  • Manually approve and deploy driver updates — every driver lands as Needs review and waits for you.
Approval method:   Automatically approve all recommended driver updates
Make updates       7
available after:

Notice what’s missing? There’s no per-vendor split and no per-device override. One policy, one device — stack two driver policies on the same machine and you’ll fight yourself.

Assign and stage

Pilot group of around 10% — your own laptops, IT, one tolerant power user. Watch it for a fortnight. Then 25%. Then the rest. The per-driver pause button is your friend the first time something breaks.

Why this actually changes behaviour

Most clients have never had a driver controlled by anyone other than Windows Update itself. The first time a Lenovo BIOS update bricks a laptop at 4pm on a Friday, that’s the conversation you do not want to be having with the owner.

With a policy on, you see the update before it hits anyone. You pause it. The rest of the fleet still ships. The client doesn’t even know it happened — and that’s the point.

“But surely Windows Update already knows what’s safe?”

Windows Update knows what applies. It doesn’t know your fleet. You do.

One last wrinkle. The policy doesn’t honour the OEM’s Computer Hardware ID targeting — so managed devices can pick up a newer “recommended” driver even when the OEM reserved a CHID-matched build for that exact model. My recommendation? Use manual approval on hardware you don’t have a spare of in a drawer to test against.

Driver update policies aren’t there to give you more buttons to click. They’re there to take the OEM utility, the random Windows Update behaviour, and the 4pm Friday surprise off the table completely.

If you’re not running one on every managed tenant, you’re outsourcing your hardware change control to luck.

CIA Brief 20260523

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Security & Threat Intelligence

Microsoft 365 Apps & Productivity

Microsoft 365 Copilot

After hours

Clarkson’s Farm Series 5 | Official Trailer – https://www.youtube.com/watch?v=GJxPc3B2osU

Editorial

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Watch out for the next CIA Brief next week

One Offer, One Deadline — Why Your MSP Marketing Keeps Stalling

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I keep seeing the same pattern on MSP websites, in newsletters, and in the sales decks owners email me for a quick review. The front page lists managed services, cyber security, backup, cloud migrations, Copilot workshops, vCIO packages, compliance assessments, and an introductory audit. Everything is on the menu. Nothing is on the clock. Then the owner wonders why prospects keep saying, “Looks great, let me think about it,” and then vanish for six months. The marketing isn’t broken because it’s ugly. It’s broken because it gives people permission to do nothing.

The buffet problem

When you put eight services in front of a prospect, you aren’t being helpful. You’re asking them to become the expert on their own problem before they can even choose who to talk to. Most business owners can’t tell you the difference between endpoint detection and managed detection, and they don’t want to. They want someone to look at their situation and say, “This one. Start here.” Every extra option you add increases the cognitive load and drops the response rate.

And yet I see owners fight this. “But we do all those things,” they tell me. Sure — but not in the same sentence, not on the same page, and not to the same prospect on day one. I’ve watched MSPs double their reply numbers by stripping a landing page down to one service, one price range, and one outcome. Same traffic. Same list. One decision instead of eight.

No deadline, no movement

The second half of the problem is the absence of a clock. If the offer is available forever, it will be taken up never. I’ve sat with MSP owners staring at a pipeline full of “warm” prospects who had a proposal three months ago and still haven’t come back. Why would they? Nothing changes if they wait. The price is the same next month. The bonus onboarding session is still there. Your calendar still has room. You’ve quietly trained them that delaying costs them nothing — while your cash flow is the one paying for their indecision.

A deadline isn’t a gimmick. It’s respect, for their time and yours. “We’re taking on three new managed services clients this quarter and we close intake on 31 May” is a sentence that forces a real conversation. Either this is the right time or it isn’t. Both answers are useful to you. “Let me think about it” is not.

Pick one door

Choose one offer. Not your whole catalogue — the single service that matches the kind of client you most want more of. For a lot of MSPs right now that’s a Copilot readiness or adoption engagement, because it opens a door the rest of your stack can walk through later. Attach a real deadline tied to something tangible: an intake window, a limited number of slots, a price that genuinely moves on a date. Say it plainly on the page, in the email, and on the call. Then stop adding extras. Every time you say, “and we can also do…,” you undo the work.

The uncomfortable part is you’ll feel like you’re leaving money on the table by not mentioning everything else. You aren’t. You’re creating a first yes, and everything else becomes a conversation you earn once the client is already working with you.

The close

Marketing isn’t a menu, it’s a door. One door, clearly marked, with a sign that says when it closes. That’s how you stop feeding prospects options and start feeding your business.

Smarter Scheduling with Microsoft Bookings

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Most of the small businesses I look at are still scheduling meetings with email.

Three back-and-forth replies. A “does Tuesday at 2 work?”. A “no sorry, Wednesday?”. A reply chain that never quite books anything.

The smarter ones have a Calendly tab open in another browser. Their bookkeeper has Calendly. Their VA has Calendly. Their accountant has Acuity. Somewhere in the mix, another subscription is being paid for.

But every one of those tenants already has Bookings sitting unused inside their Microsoft 365 plan. And almost nobody knows it comes in two flavours.

That’s not a feature gap. That’s an awareness gap.

What is Bookings, really?

Bookings is two products with the same name.

The first is Bookings with me — Microsoft also calls it Personal Bookings. It’s a per-person scheduling page tied to your Outlook calendar. Someone hits your link, picks a meeting type, picks a slot inside your real availability, and the invite lands in both calendars. No mailbox to provision. No staff list. Just you and your calendar.

The second is a shared booking page. A separate scheduling mailbox for a team, a service, or a whole business. Multiple staff, multiple services, different durations. The classic “book a haircut, pick your stylist” page — except it works just as well for “30-minute discovery call with whoever on the team is free”.

Personal page for an individual. Shared page for a business.

Most SMBs need both.

Step-by-Step: standing up your personal page
Open the Bookings app

Go to book.ms, or pin the Bookings app to the rail in Outlook on the web or Teams. On the home page you’ll see Personal booking page at the top — that’s Bookings with me. Microsoft has already published one for you with default 15- and 30-minute meeting types. The detail is in the Personal Bookings FAQ on Microsoft Learn.

Set your meeting types

Edit the defaults. Set duration, location (Teams meeting by default — toggle it off for in-person), and availability hours. Mark each one Public to put it on your link, or Private to share only as a one-off.

Add a buffer

This is the setting people miss. Buffer time before and after each appointment is what stops your day collapsing into back-to-backs. Five or ten minutes on every meeting type. Buffer behaviour lives under Configure service availability.

Drop the link into your signature

Copy the public URL. Paste it into your Outlook signature:

https://outlook.office.com/bookwithme/user@yourdomain.com/

Notice what’s missing? No “let me know what works”. No “looking forward to hearing back”. The link does the asking.

Step-by-Step: standing up a shared page
Create the page

In Bookings, under Shared Bookings, choose Create booking page. Start from scratch unless you’ve got a template to clone. Fill in business name, logo, and hours — the setup walkthrough on Microsoft Learn lists the four required pieces.

Add staff and services

Add bookable staff. For each one, leave Events on Microsoft 365 calendar affect availability on so their Outlook calendar drives free/busy. Then create services — a service is a bookable thing (“30-min discovery”, “60-min onboarding”) with its own duration, buffer, and reminder cadence.

Decide who can be self-served

Turn off self-service for anything strangers shouldn’t book. Mark internal-only services Private.

Why this actually changes behaviour

“Hey, got a few minutes next week?” becomes “Sure — book a time.”

That one swap is the whole post.

The personal page kills the email tennis between you and your contacts. The shared page kills it between your clients and your team. The calendar becomes the source of truth, not the inbox.

Here’s the real win: it’s already in the licence. Business Basic, Business Standard, Business Premium, the E plans — Bookings is there. Calendly is not.

If your clients are still booking meetings by email, they’re paying for two things and using one of them.

Bookings isn’t there to schedule meetings. It’s there to stop scheduling them at all.

When Your LLM Goes Down: Are MSPs Designing a New Single Point of Failure?

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Over the past year, I’ve watched something fascinating—and slightly uncomfortable—happen inside MSPs and their clients’ businesses. AI tools, particularly Microsoft 365 Copilot, have gone from “interesting experiment” to “critical part of how work gets done” at a pace I don’t think many people fully appreciate yet.

And that raises an uncomfortable question we haven’t really answered:

What happens when the LLM isn’t there?

Not slow. Not “a bit less helpful.”
Actually unavailable.

AI Has Quietly Moved Into the Critical Path

In some of the environments I’m seeing, Copilot isn’t just helping draft emails or summarise meetings. It’s shaping decisions.

Staff are using it to draft client responses, interpret data, build proposals, prepare board slides, and make sense of complex information faster than they ever did before. Managers are using it to think through options, not just document outcomes.

That’s important, because it means AI has crossed a line. It’s no longer a convenience layer. It’s becoming part of the business process itself.

From an MSP perspective, that should set off the same internal alarm bells as any other critical dependency. Because if your client’s process assumes Copilot is available, then Copilot downtime is no longer “an inconvenience”. It’s downtime.

The New Form of Business Continuity Risk

We’re very good, as an industry, at talking about disaster recovery in traditional terms. Backups. Redundancy. Failover. RPOs and RTOs.

But AI introduces a different kind of risk—cognitive dependency.

Here’s a simple scenario I’ve already seen play out in smaller ways:

A staff member is used to Copilot summarising long email threads before client calls. One day it’s unavailable. They’re still expected to run the meeting, but they haven’t read the full thread because the process evolved around “the AI will summarise it”.

No data was lost. No system was breached. But productivity drops, confidence drops, and errors creep in.

Now scale that to proposal preparation, reporting, or internal decision-making processes that assume AI assistance.

We haven’t lost data—but we’ve lost thinking capacity under time pressure.

“The AI Will Be Back Soon” Is Not a Strategy

One of the more dangerous assumptions I hear is:
“Microsoft will fix it quickly.”

Maybe. Probably. But that’s not business continuity planning. That’s hope.

As MSPs, we need to start asking different questions during AI discussions:

  • What manual process exists if AI is unavailable for a day?

  • Do staff know how to complete the task without AI, or have we trained that muscle out of them?

  • Which workflows are AI‑assisted—and which are AI‑dependent?

This isn’t about rejecting AI. I’m fully in favour of using Copilot when it genuinely improves outcomes. But professional-grade technology adoption has always meant understanding failure modes, not just success stories.

Designing AI‑Resilient Workflows

The smarter MSPs I’m working with are starting to treat AI like any other tier‑one system:

  • Document the “AI unavailable” version of key workflows

  • Set expectations with clients that AI enhances productivity but is not guaranteed

  • Train staff to validate, understand, and reconstruct work without AI assistance

  • Decide consciously where AI is optional versus where it must never be the only path

Ironically, the organisations doing this best often get more value from Copilot, not less. Why? Because they understand it as an accelerator—not a replacement for thinking.

The Question MSPs Should Be Asking Right Now

AI isn’t going away. Dependency will increase, not decrease. That makes this a leadership issue, not a technical one.

So here’s the question I think every MSP owner should be asking themselves:

If Copilot vanished tomorrow, which of my clients’ processes would break—and would they even realise why?

If the answer makes you uncomfortable, that’s a good thing.

That discomfort is the early warning system telling you it’s time to evolve disaster recovery thinking for the age of AI.

Windows Update for Business rings via Intune

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Most of the Windows patching pain I see at SMB sites isn’t a Windows problem. It’s a governance problem.

Devices are enrolled. Updates are technically arriving. But there’s no ring. No pilot. No deadline. Patch Tuesday lands, somebody’s accounting machine reboots in the middle of a BAS run, the partner blames “Windows”, and the whole patching conversation gets put off for another quarter.

That’s not a tooling gap. That’s a configuration gap.

And here’s the kicker — Microsoft renamed the whole thing in April 2025. Windows Update for Business is now Windows Update Client Policies, and the deployment service is folded into Windows Autopatch, which is now included with Microsoft 365 Business Premium. If you’re still hand-rolling rings on a Business Premium tenant and ignoring Autopatch, you’re doing more work than you need to.

What update rings really are

An update ring is a Windows Update client policy. It tells the Windows Update client on the device when to look, how long to wait, when to install, and when to reboot. Nothing more.

It’s not a patch repository. It’s not a scanner. It’s a set of timing instructions the device honours when it talks to Microsoft’s update endpoints.

Once you accept that, the rest gets simpler. You’re not pushing patches. You’re staging trust.

Step-by-Step: build a three-ring rollout in Intune

Portal only. No PowerShell.

Open the unified updates dashboard

Sign in to intune.microsoft.com, then go to Devices > By platform > Windows > Manage updates > Windows updates and click the Update rings tab. This is the new unified surface — Microsoft’s docs on managing update rings live here.

Create the Pilot ring

Click Create profile. Name it WUR – Pilot. Quality update deferral: 0 days. Feature update deferral: 0 days. Automatic update behaviour: Auto install at maintenance time. Deadline for quality: 2. Deadline for feature: 2. Grace period: 2.

Assign to a device group of 3-5 representative machines. Not user groups. Devices.

Create the Broad ring

Same shape. Name it WUR – Broad. Quality deferral: 3. Feature deferral: 7. Same deadline/grace as Pilot. Assign to the bulk of your fleet.

Create the Critical ring

WUR – Critical. Quality deferral: 7. Feature deferral: 30. Assign to the boss’s machine, the EFTPOS PC, the design workstation — whatever you can’t afford to surprise.

Three rings. That’s it. Don’t build five.

The deferral / deadline / grace mental model

People get this wrong constantly. Here’s the model in one block.

Deferral  → how many days AFTER Microsoft releases the update
            before the device is even offered it.
Deadline  → how many days AFTER the device sees the update
            before it's force-installed.
Grace     → how many days AFTER install before reboot is forced.

Notice what’s missing? Patch Tuesday as a reference point. The deadline counts from when that device scanned and saw the update — not the calendar. Microsoft moved to this model deliberately to make restart timing predictable across a fleet.

Set them. Don’t leave any of the three blank. Blank means forever on a sleepy laptop.

Why this actually changes behaviour

The mistake isn’t choosing the wrong deferral. The mistake is leaving the pause button in users’ hands.

In the ring settings, set Option to pause Windows updates to Disable. Otherwise a user can park their patches for 35 days, and you’ll find out at the next quarterly review.

Set automatic update behaviour to Auto install at maintenance time with active hours configured. The device patches itself. The user keeps their day. The MSP stops being the villain.

“Why do my updates keep nagging me?”

They don’t, anymore. You set active hours. The reboot finds its time, not yours.

Copilot doesn’t get tired. Neither does Windows Update. Use that.

A word on Autopatch

If the tenant is Business Premium, you now get the full Windows Autopatch service — rings auto-built, rollback on signal, 95% currency SLO. On those tenants, don’t assign hand-built rings to Autopatch-managed devices. They’ll fight each other.

My recommendation? Business Premium tenants → Autopatch. Everything else → three rings, the shape above, locked down so users can’t pause.

Update rings aren’t there to slow patching down. They’re there to remove the conversation about patching completely.

If your clients are still asking when their machines will reboot, you haven’t finished the job.

AI Didn’t Remove Programming – It Lowered the Bar

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One of the most dangerous misunderstandings I hear is:
“AI means we don’t need programming anymore.”

The opposite is true.

We need more programming literacy—just a different kind.

AI doesn’t replace logic, structure, or clarity. It amplifies them. When an AI tool “writes code” for you, what it’s really doing is translating your intent into something executable. If your intent is vague, messy, or logically broken, the output will be too.

MSPs already see this in practice:

  • A poorly described Power Automate flow that works once and then quietly breaks.

  • An AI-generated script that technically runs but makes unsafe assumptions.

  • A Copilot prompt that looks clever but produces useless business output.

The common issue isn’t the tool. It’s the thinking behind the instructions.

Understanding basic concepts—inputs, outputs, conditions, loops, exceptions—has never been more important. The difference now is you don’t need to memorise syntax. You need to think clearly and explain cleanly.

This Is a Business Advantage, Not a Technical Party Trick

Here’s where many MSPs miss the opportunity.

They see AI-assisted “programming” as something clever techs play with internally. In reality, it’s fast becoming a deliverable business capability.

Think about your SMB clients:

  • They know their processes are inefficient.

  • They can explain what they want, but not how to build it.

  • They don’t want a six‑month dev project for a simple workflow problem.

An MSP that can sit with a client, map a process in plain English, and turn it into an automated solution is no longer just “support”. You’re helping redesign how the business operates.

And the simplicity is the point.

A one‑page English description that becomes:

  • A ticket triage workflow

  • An onboarding checklist generator

  • A management report assembler

  • A light internal chatbot using their own documents

None of that needs hardcore development skills anymore—but all of it still needs structured thinking.

Your Team Doesn’t Need Coding Skills – They Need Programming Awareness

This is where MSP leaders need to be deliberate.

You don’t suddenly need Python experts across your service desk. What you do need is:

  • Staff who can break problems into steps

  • People who can explain outcomes unambiguously

  • A shared understanding of how logic flows

If your team can already document SOPs well, they are halfway there.

I’ve seen MSPs get real value by:

  • Treating AI prompts like mini specifications, not chat questions

  • Reviewing AI-generated automations as a team, not blindly deploying them

  • Teaching junior staff how to describe a problem, not just which tool to click

Those are capability investments, not tool training.

The MSPs Who Win Will Treat This as a Core Skill

We’ve crossed a line. Programming is no longer gated by language barriers—it’s gated by thinking quality.

That changes what “technical literacy” means for MSPs.

The firms that thrive over the next few years won’t be the ones chasing every new AI tool. They’ll be the ones that:

  • Build strong internal habits around logical thinking

  • Help clients translate business problems into clear instructions

  • Package simple automation as repeatable, billable outcomes

If English is now the language of code, the question is simple:

Are you teaching your people how to speak it clearly—or assuming the tools will do that for them?

That’s a strategic choice every MSP leader needs to make, sooner rather than later.