Copilot Catalyst Lesson 4: You Get Three Chances to Make a First Impression
In every Copilot rollout, we seem to meet two groups immediately: AI optimists expecting magic, and AI skeptics bracing for disappointment. These people make themselves visible early in the conversation. The optimists walk in ready to be impressed, while the skeptics arrive ready to be proven right that this whole AI thing is a sham.
The one thing we don't see is a lot of neutral opinions.
Even if they have only lightly worked with LLMs in the past, people come into the AI conversation with strongly held beliefs. Whether based on news they have seen, articles they read have read, or just their natural disposition, most people feel like they have the inside track on predicting the future and they are eager to tell you all about it.
But beneath the noise of the true believers and the vocal doubters, there is a hidden subcategory.
The Anxious Newcomer
The anxious newcomers are people who haven’t yet interacted with AI or taken the time to learn about it, but they know it’s coming. Their anxiety is often through the roof, not because they’ve tried it and failed, but because they haven’t taken the time to experiment and fear they’re already behind. They feel like they should “get it” already. The distance between their current skill level and where they think they need to be creates a quiet panic.
This is the Experience Gap.
Here’s the danger: because of this anxiety, these people aren’t sitting in the back quietly. Instead, they vocalize strong opinions as a defense mechanism.
To hide their anxiety, they pick a side. They show up with fully formed opinions just like everyone else, masking their uncertainty by blending into either the AI optimist camp or the AI skeptic camp.
Their opinion is “baked in” without any actual experience behind it. Their stance isn’t a conviction; it’s a shield. And because that shield is fragile, which way they land, whether they become a permanent advocate or a permanent detractor, depends entirely on their first few interactions.
Three Times a Charm
Rolling out Copilot provides a unique opportunity because it offers a “blank slate” to reframe expectations for all three groups: the optimists, the skeptics, and the anxious newcomers.
Even for those with prior LLM experience, this is still a new frontier. They are inevitably comparing this to their time with ChatGPT or Gemini, but this is the first time they can directly access their specific work files and M365 apps like Outlook and Excel. That shift from general knowledge to their specific work data and familiar tools offers a reset button. It’s an opportunity to level set expectations.
There’s not a magic number but we find three seems to be the sweet spot.
Three good experiences can create an advocate and build momentum.
Three bad experiences validate skepticism, deflate curiosity, and dig a hole so deep it can take months to climb out of.
I like to catch all three groups at the moment their beliefs collide with reality. This is especially true of the anxious newcomers. A few realistic, confidence-building wins can shift someone from assumption-driven to experience-driven thinking almost immediately and can change the course of someone’s entire experience.
The Solution: Engineer the First Impression
To close the experience gap without overwhelming them, we take people through a guided exercise in our kickoff workshop. We focus on a task we know LLMs excel at: writing technical documents.
The “Low Bar” Win: We ask them to prompt Copilot generally to create a job description for a role they hire for. It outputs a decent draft. People are generally impressed by the speed.
The “Iterative” Win: We get them to add specific details about the role and let the LLM output again. They see how it listens and adjusts. They are impressed by the integration.
The “Integration” Win: Finally, we have them upload a job description in the company’s specific style and format.
By the end of these three exercises, they have a fully formatted, tailored job description that would have taken hours to write, outputted in three minutes in the company format. It might seem a simple prompt exercise, but we have yet to see someone unimpressed with this.
At that moment, the optimist, the skeptic, and the anxious newcomer all share the exact same thought. They look at the screen, lean back, and silently think: “Okay, that’s cool.”
And that is the opening you need to ask the next question: “What other tasks do you not like doing?”
The Shift: From Anxiety to Agency
Once they see that output, the dynamic in the room shifts physically. Shoulders drop. The optimist realizes that sometimes you need to work with Copilot iteratively to get the desired outcome, the defensive arms crossed over chests of the skeptics unfold, and the “mask” of the Anxious Newcomer falls away because they no longer need to protect themselves from the unknown. They have seen it, touched it, and made it work.
This is the critical pivot point. You have successfully moved them from opinion to curiosity about the tool.
Now, we can step back having done our job of grounded them without drowning them. When they inevitably stumble sometime in their next few prompts, they tend not to treat it as proof of their previously held opinion. You haven't just taught them a tool; you've given them the opportunity to change their mind. Once that happens, let them run on their own and explore.
The Takeaway
It’s not about who walked in as an optimist or a skeptic. It’s not even about the anxious newcomers hiding behind their shields. It’s about the moment the beliefs of all three groups meet reality and capitalizing on that moment to reset expectations.
AI adoption is not just a technology problem; it’s a human problem. Those first three interactions are the chance you get to unpack that baggage before it becomes a permanent roadblock. Engineer the wins, close the experience gap, and watch the conversation change from “Why do I need this?” to “What else can this do?”
Up Next
Next we’ll explore lesson 5: Culture is Contagious. So is Resistance
If you’re navigating this journey right now, take what helps and leave the rest. These lessons are meant to be used, not just read. And if you want to compare notes, our team at FlexPoint Consulting is always happy to share what’s working and what isn’t or just reach out to me directly.
If something here resonates, or if your own experience proves it differently, drop a comment below. The conversation is where the real learning happens.