Picture a room full of executives from one of Microsoft’s largest accounts. The sales team has spent six months trying to close them and gotten nowhere. This is the last meeting before the account goes to Google.
Shari L. Oswald walks in and doesn’t open a slide deck. She asks a question. What in your day is painful?
By the end of the session she has walked every person in that room through a demo built around their own answers, and checked with each of them in turn: did I solve your problem?
She closed a $25 million deal that day.
That was part of the Customer Immersion Experience, Microsoft’s former hands-on program for enterprise accounts of 5,000 seats and up. Oswald facilitated it for eight years and trained Microsoft Partners to deliver it themselves.
It changed how she thinks about technology and the people who are supposed to use it, and it’s the experience she now brings to her own company, emPOWERedLearning.
Oswald is a certified SharePoint Solutions Architect, a Microsoft Certified Copilot Adoption Specialist, and the author of SharePoint courses for LinkedIn Learning. Her diagnosis of why so many Copilot rollouts stall is uncomfortable for most IT teams to hear, and she says it without much cushioning.
“You can’t just say, ‘We’re IT, and we’re throwing this over the fence at you.'”
Inline with Microsoft’s latest thinking, the Microsoft MVP believes IT leaders need to lead the adoption conversation, not just the governance one.
She spoke to Cloudwell about where that conversation starts, how a CIO earns the authority to lead it, and what to do when your most enthusiastic users are already building agents without you.
Where does a Copilot conversation with the business start for an IT leader?
Shari L. Oswald: With a question, not a feature list. Ask them: what in your day sucks up your time? What’s tedious and repetitive? What could we replace your human time with AI time on?
Then listen.
Every session I run on Copilot is different, because different people have different jobs, but some things come up every time, like email. I always write it on the board before anyone says it, because somebody is going to.
Then it’s reports. Every department rolls up a report to the person at the top, and that person has to read all of it and work out how it fits the strategy.
Then it’s numbers: exports of data they can’t make sense of, which we clean up before we do anything clever with them.
IT has to ask these questions before acting, because otherwise you’re just assuming. And if you go in saying this is the newest, coolest, shiniest thing and it’s going to be so great for your job, the person on the other side is thinking one thing. What’s in it for me? Why should I bother?
A lot of IT leaders have been the “move us to the cloud” person. How do they get the authority to lead on AI?
SLO: That’s a tough one, because it depends on the culture of the company. Either IT is seen as a value-add or it’s seen as a necessity that has to be dealt with.
I see both. I watch the CFO and the CIO fight because the CFO won’t provision the equipment or the people the CIO needs, and everyone can see it happening.
It starts at the top and it trickles down. If leadership doesn’t see IT as a strategic partner, the CIO will always struggle. They’re a means to an end. Keep us secure, keep the lights on.
What the CIO can control is whether they’re visibly behind this themselves. You have to demonstrate that you’re adopting it, that you value it, and that you’re skilled in it.
“You can’t lead an adoption you’re not part of.”
So, what does a leadership team that’s serious about this do first?
SLO: Discovery. For example, at a credit union I’m working with, I started with a full day across two sessions. Senior leadership in the morning, their steering committee in the afternoon.
I asked: What are you hearing about AI? What do you think? How would it help you? And, quietly, what are you already doing on the side that you’re not telling anyone about? They are. Everyone is.
Two things come out of a session like that.
The steering committee is shocked that leadership is open to this at all. And leadership stops asking “how does this save me time” and starts asking “how does this help us stay relevant and competitive.”
That’s the shift you want.
Once leadership sees it as a strategic question rather than a productivity gadget, everything below them moves.
Microsoft says AI adoption is stalling for four reasons: cost, skills, vendor pricing, and risk. Is that what you see on the ground?
SLO: Check, check, check, and check. All of those.
The one I hadn’t thought about came from the credit union I mentioned before. They’re heavily regulated, so the internal risk conversation is expected.
The surprise is the external one.
Their customers are going to pull their statements, feed them into an AI, and ask what they should do about retirement. That’s already happening. So what is the credit union putting out there for those AI tools to consume? If they’re not producing content people can use that way, they fall behind.
So, the risk cuts both ways. There’s a risk in using AI, and there’s a risk in falling behind because you didn’t.
How do you restart a Copilot rollout that’s stalled?
SLO: I use the ADKAR framework: awareness, desire, knowledge, ability, reinforcement. Most organizations skip the first three. They give people the tech, don’t tell them why it’s coming, don’t make them want it, and drop them straight into ability. Figure it out yourself.
So, you back everyone up to awareness. Did you know you have this? Did you know what it can do for you?
Then you go after low-hanging fruit.
I run a workshop where people map their role against their business challenge, and it becomes a matrix. Where the same challenge shows up across several roles, that’s your first win.
Solve it, show it, move on.
And keep reminding people. I like a weekly drip: a short article with two or three tips, a two-minute video showing how to do the thing.
Did you know, did you know, did you know. It’s a constant nudge, and it works.
Should IT deliver the training itself?
SLO: No. IT teams are the worst ones to deliver training, and I say that with love for the people I’ve worked alongside for decades.
It has nothing to do with how well they know the product. It’s just that adoption is more of a facilitation skill.
You need to sit with people and find out what they’re trying to do, and then you build the learning around what you discover.
The ‘here’s where you click’ style training is useless if nobody cares why they’re clicking.
That’s what a partner or an adoption specialist is for. The IT leader’s job is to own the outcome and bring in the people who can deliver it.
Some people aren’t stalled at all. They’ve heard the marketing and they’re already building agents. What does IT do with them?
SLO: The first message to the business should be: just because you can doesn’t mean you should.
The second is one I’ve been saying since my SharePoint days: clean out your garbage.
I’ve migrated terabytes of data for people who insist they need all of it. I ask, “You need the potluck sign-up list from 1993? You need that?”
An agent pointed at old, unreliable data gives you old, unreliable answers, and IT will be the ones cleaning up.
But don’t shut the enthusiasts down either. Pull them into a champions community. That way you’re acknowledging they’re forward-thinking and giving them a seat on the steering committee. “We need you to help us make sure people are using this well.” You’re directing the enthusiasm rather than fighting it.
ROI of Copilot: Microsoft is now telling everyone to stop measuring time saved and talk about outcomes instead. Do you agree this is the right advice for IT to lead with?
SLO: Time saved is subjective. But it can also be measurable. In a C-suite session someone will say “that would save me two hours a week,” and you can see the CFO doing the math. He knows what that person costs per hour.
Sometimes that means proper job analysis: what do you do all day, and how long does it take? Tedious, but that’s where the numbers come from.
The bigger value is somewhere else, though.
In a lot of industries, keeping up with regulation is a full-time job. Using AI to track new legislation and benchmark yourself against it, watching market trends, what’s in the news, how you position yourself to meet it. That’s where AI creates new value.
Every business exists to solve somebody’s problem. A bank solves “where do I keep my money and get at it.”
So, the outcome question is simple. What’s the problem your business was set up to solve, and does Copilot help you solve it better than you did last year?
Now there’s a meter on Copilot Cowork and Scout. How should IT think about credits?
SLO: Start with a budget. And start experimenting yourself first. People are posting on LinkedIn: I built this agent, it cost this many credits, this many dollars. Do that internally. Know what things cost before someone asks you.
Then, for your organization, run a test group, find the average, and budget from that. Otherwise, they’ll spend, spend, spend, and you’ll end up with a bill that looks like your credit card statement when you went a little nuts on vacation.
For years we’ve had this same conversation about Azure credits. Copilot credits are the same. Everything is a trade-off of time or money, and the difference now is that it’s not a one-time cost. It’s ongoing. You need to budget for it like it is.
“Everything is a trade-off of time or money. The difference now is it’s ongoing.”
Need help getting Copilot used, not just licensed?
Shari L. Oswald is a Microsoft MVP and Chief Experience Officer at emPOWERedLearning, the adoption and productivity practice she has run from Colorado Springs since 1999. She’s a certified SharePoint Solutions Architect and Microsoft Certified Adoption Specialist, authors SharePoint courses for LinkedIn Learning. She works with organizations on site or remotely, and conversations are free. Find her at shortcutshari.com or on LinkedIn, and if you’re at ESPC in Amsterdam, 30 November to 3 December 2026, she’s speaking there for the first time.
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If you’d rather have a partner run the discovery, the champions program and the training while your team keeps hold of governance, that’s what Cloudwell’s Copilot Enablement Program is built for. Sounds useful? Get in touch