Phase 1: Skeptical Curiosity
Fine, I’ll use AI and see what it’s all about. I don’t trust it though.

Phase 2: The First Prompt
Employee opens the AI chat tool of the moment (ideally one with a compliant enterprise account, but this post isn’t about that) and enters something basic like: “Write an email to X person about Y topic.” Wow, cool. That was helpful.

Phase 3: Writing Assistant Era
Employee starts asking the tool for more writing help: “Write an article about X topic.” “Create a blog post about Y.” Dang, that’s awesome.

Phase 4: The Experiment Zone
Now comes the flurry of both serious and fun prompts.
Serious: “Write a memo to leadership about these findings,” with a copy-paste avalanche of fragmented info that turns into a polished output the employee is thrilled to have expedited.
Fun: “Write a funny five-year anniversary note for my colleague Brenda. She’s in Dallas, works in media, loves orchids.” The AI nails it. The employee tweaks it slightly and posts it to Slack or Teams.

Phase 5: Strategic Prompting
The prompts evolve: business plans, project plans, go-to-market strategies, summaries, sales talking points, market scans.
Employee discovers they can upload files, images, and documents. (Hopefully on the enterprise version. Big plug for that.)

This post is about what I see with prompt upskilling, but just to say it: Using public AI tools can pose serious risks if you’re entering sensitive or confidential information. These platforms may store prompts or responses, potentially exposing proprietary data or personal details. That’s why secure, enterprise grade AI tools are essential: they offer data encryption, access controls, and usage governance to ensure your information stays protected.

Phase 6: Prompt Perspective Shift
Then it clicks: you’ve only been prompting “as yourself.” You start giving clearer instructions about what you want back, in what format, and using which inputs.
You learn to prompt as an industry expert outside your role. You ask for sources. You ask for thinking. The AI delivers.

Phase 7: Structured Prompting
Time for a major prompt evolution:
Employee learns to prompt using taxonomies that include role, request, goal, instructions, considerations, tone, style, and output format.
Example: “Act as a strategic marketing advisor with expertise in quarterly planning, audience analysis, and content campaigns across multiple channels.”

Phase 8: Prompt Hoarding
The prompt library begins. Word docs and spreadsheets start piling up. LinkedIn saves stack up. All of it might be useful one day.

Phase 9: Prompt Overload
Weeks pass. Employee is drowning in saved prompt docs across cloud folders and shared drives. Can’t find that one prompt from last week.
Still tries to send them along to help a prompt newbie.

Phase 10: Prompt Infrastructure Seekers
Employee starts hunting for tools that offer a searchable, categorized prompt database to make this curated chaos usable again.
Because the productivity gain of great prompting is now being slowed down… by all the prompts.

Oh, the irony.