SupportWorld Live is one of my favorite events of the year. It’s where I catch up with industry friends, swap ideas, and usually get a chance to share a few thoughts from the stage. But this time around, I wasn’t speaking. Which, I’ll be honest, felt a little weird.
I wasn’t sure how it would affect my enjoyment of the event. Would it be awkward? Would I just hang out in the hallway pretending to take important calls? How much of it would actually feel interesting and enriching?
But once I got into it… really listening, taking notes, following the threads… I ended up having a great time. And I mean brain buzzing, questioning some of my own assumptions is kind of great.
So instead of giving you a generic “Top 5 Sessions” list (you’ve probably got enough of those in your feed already), I’m sharing the five moments that actually challenged me. The ones that got under my skin a bit, and gave me new and valuable perspectives.
1. AI is boosting productivity… and killing critical thinking
One of the keynotes brought up a point that made me pause. It showed what we all kind of know but don’t always say out loud: as AI adoption goes up, productivity improves... but critical thinking and quality tend to dip.
We’ve entered this era where a tool can summarize the meeting, draft the reply, close the ticket, and write up the report, all with minimal effort. On paper, it looks amazing. You’re getting more done than ever. But if you take a step back, you realize: you didn’t actually decide anything. You just greenlit whatever the tool handed you.
And look, I’m not anti-AI. I’ve spent enough time wrestling with workflows to appreciate a good shortcut. But there's a point where efficiency stops being helpful and starts getting DANGEROUS.
When we get too comfortable letting the tool lead, we lose the pause. The second guess. The moment of “Wait… is this actually the right thing to do?”; and that moment matters more now than ever before.
Because large language models can’t read the room. They can’t detect nuance, or know when something looks right but feels wrong (yet). They don’t quite “get” consequences and can’t be held accountable. That’s still on us. And if we’re not flexing that part of our brain regularly, we will lose practice.
To be honest, I was hoping the keynote unpacked that tension – the cost of convenience, the invisible trade-offs. But instead, we got a nostalgic stroll through PC history and the early internet. (Which is fine! I love a good retro moment. But maybe not what I came for.)
The bigger point is this: most people in Service Management aren’t new to change. We’ve been doing “digital transformation” since before it had a hashtag. What we need now isn’t another cheerleading session for automation. We need to talk about what’s being left behind. Because we’re at risk of replacing not just old systems, but old habits. Old instincts.
And if we’re not careful, we’ll end up with faster outputs and weaker thinking. Innovation as autopilot. What’s the point?
2. Diversity is a competitive advantage
One of the most powerful sessions I attended had nothing to do with tools, frameworks, or the latest acronym we’re all supposed to care about. It was about people. Specifically, women in tech, and the uphill climb they are still navigating.
Vikki Rogers led the panel, and it didn’t waste time sugarcoating. The stats came fast, and they hit hard:
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Women make up 47% of the workforce… but only 26% of computing roles.
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Less than 10% of tech leadership jobs are held by women.
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And women in top IT roles, on average, last about 1.5 years. Men hang on for over 4.
And those are just the numbers. The session also dug into stuff that doesn’t always make it onto the slide deck, like how 60% of male managers say they feel “uncomfortable” meeting alone with a female colleague. Which is just wild when you consider how much career development happens in those quiet, unscheduled moments. If people aren’t being invited into those spaces, they’re not being invited into opportunities.
Now, here’s where things clicked for me; this isn’t just about fairness (though yeah, that should be enough). This is actually about business, results and performance too.
Across the board, the data shows that diverse teams aren’t just nice to have; they solve problems faster. They think differently. They build things more people can actually use. They stick around longer. They see more, and that leads to better outcomes.
So if your org is still treating diversity like a side quest, a checkbox to appease HR or make the annual report look good, your company may have missed the actual point. You’re leaving performance on the table. You’re choosing short-term comfort over long-term capability.
Are the solutions simple? Of course not. But they’re also not a mystery:
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Real mentorship that goes beyond the performative.
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Hiring practices that actually widen the funnel.
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Pay transparency that closes the gap instead of hiding it.
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Outreach that starts way before the job posting.
The session didn’t promise silver bullets. It didn’t pretend that culture shifts happen overnight. But it did make one thing painfully clear: if you want a stronger team, you need a wider lens. And that starts by listening, and really hearing what people are saying. Especially when it makes you uncomfortable.
3. IT was never meant to deliver great experiences – but it has to now
There’s a line from Katrina Macdermid’s session that’s been rattling around in my head ever since:
“IT wasn’t designed to deliver experiences. It was designed to control, secure, and make technology cost-effective.”
And yeah, that makes sense of course. But it also puts things into perspective.
The whole foundation of IT was built on Risk Management. Predictability. Cost control. Standardization. “Don’t break anything” was basically our unofficial motto for, like, 30 years. And that made a lot of sense for a long time.
But somewhere along the way, the world changed. People started expecting more than just uptime and password resets. They wanted things to work and feel good.
IT wasn’t just the back office anymore, it became part of the overall human experience. Now we’ve got this weird tension: an industry built for control is being asked to lead with empathy. No wonder it feels clunky sometimes.
This is why experience still feels like a second language in a lot of IT shops. We try to translate it into metrics: slap a CSAT survey on the backend, maybe buy an “experience tool” and roll out a few smiley faces. Job done, right?
Not really.
Experience isn’t something you add after the fact. It’s not a layer you paint over the top of a legacy system and hope nobody notices the cracks underneath. It’s the result of everything working together: process, tech, behavior, mindset.
And if your whole setup is still built around containment and control, it doesn’t matter how many “delight” stickers you slap on your service catalog. People can feel the difference between being supported and being used. It’s posing.
We’re trying to retrofit empathy into a system that wasn’t built to feel anything at all. That doesn’t mean we give up, obviously, but it does mean we have to stop treating this like a plugin. It’s not a feature upgrade. We need to rebuild from scratch.
And that’s the hard part. Because the stuff we’re being asked to let go of is the same stuff that’s kept us safe for decades. But if experience really is the future of IT (and I absolutely think it is) then we’ve got both learning and unlearning to do.
4. AI can’t save a messy help desk – but it can help transform a solid one
One of the most practical sessions I attended came from a team working with Wendy’s. They’re using GenAI in their help desk – but not in the way most people assume.
The first big change: No tiered support. Nearly 90% of issues are resolved on first contact. They simplified processes, empowered agents, and then added AI to streamline further. Their average handle time dropped from 20 to 15 minutes due to process improvement. Then AI took it to 10. And the order of that improvement matters because without the first improvement, the second one is not possible. This is the AI transformation teams will go through.
One quote that stands out in my memory is that they claimed that 80% of the work for this project was getting legal and security approval. So if you’re trying to implement AI or AI features, you know where to start.
Too often we throw AI at bad workflows and wonder why nothing improves. It turns out AI is not magic. It's an amplifier – and it amplifies whatever system you already have.
5. Experience-level agreements only work if vendors really collaborate
In one of the better “Wait, this might actually work” moments of the conference, a speaker on the XLA panel shared a story that stuck with me.
Basically, a company brought in multiple vendors (different providers, different specialties, different org charts) and said, “Hey, you’re all responsible for hitting this shared experience target. If you meet it together, you won’t have to re-bid next year; we’ll extend your conference.”
Instead of the usual blame-passing when something went sideways (“That’s their tool, not ours” / “We’re waiting on their fix”), the vendors actually started working together. They were collaborating, sharing insights, coordinating timelines – not because they suddenly became best friends, but because their incentives were aligned.
It’s such a simple idea, but it feels radical in a world where we’ve all been trained to protect our slice of the pie. Most contracts are built like little fiefdoms – each vendor focused on their own KPIs, their own SLAs, their own turf. The idea of asking them to care about shared outcomes seems counter-intuitive.
But that’s the shift. Experience (real experience, the kind users can feel) doesn’t care about your org chart. It’s not going to stop and ask, “Wait, which vendor owns this?” when something breaks. It just knows whether things are working or not.
And if you’re still locking in metrics that only reflect one tiny piece of the puzzle, don’t be surprised when what you get is an incomplete picture.
Final thoughts
A good conference doesn’t just hand you a bag of stress balls and a list of takeaways you already half-agree with. It pokes at you. It rattles the frameworks a bit. It leaves you turning something over in your head on the flight home, wondering if maybe it’s time to look at things a little differently.
As much as we go on and on about change, in IT and Service Management, we’re actually creatures of habit. We love a good process, a clear checklist and a dependable acronym. There’s comfort in the repeatable, especially when the world around us keeps shifting faster than we can whiteboard it.
But the thing about comfort is it doesn’t always challenge you. And if there’s one thing SupportWorld Live reminded me of this year, it’s that challenging the stuff we think we’ve figured out is usually where the most interesting work starts.
The sessions that hit hardest weren’t the ones where I nodded along. They were the ones that made me tilt my head a little. Squint. Reconsider. Sometimes I’m left with a new perspective. Sometimes I feel a little annoyed. But every time, I leave thinking.
And in a world increasingly run on autopilot, that’s huge value.