After training over 5,000 professionals in corporate technology, I finally learned that my carefully crafted stories were missing the point entirely
Room 401. Another Monday morning. Eight faces stared at me, a mix of anxiety and resignation. I was setting up my laptop, connecting to the projector, and getting ready to teach an advanced Excel course to a group of financial analysts.
I knew exactly how this would go.
In about three minutes, I’d share my famous story about the time I messed up a crucial financial report because I didn’t understand pivot tables.
The story that always worked. The one that made everyone relax and think,
“If he recovered from that, maybe I won’t look so stupid asking questions.”
But that morning, something stopped me. Maybe it was the way the woman in the front row was gripping her coffee cup like a lifeline. Or how the gentleman in the corner kept adjusting his tie—a nervous tick I’ve seen hundreds of times before.
I realised I was tired. Not physically tired—though God knows setting up training rooms at 7.30 AM takes its toll—but tired of the performance.
Tired of being “Relatable Training Guy” with his perfect collection of self-deprecating tech stories.
🔑 Key Takeaways
- Authentic classroom connection requires current vulnerability, not past anecdotes.
- Real learning happens in unscripted moments.
- Technical expertise must balance with genuine human connection.
- Learner anxiety decreases when instructors share present struggles.
- The most powerful teaching moments often happen outside formal instruction.
The Evolution of My Training Persona
The Early Days: Building My Story Arsenal
When I first started training corporate clients in the late 1990s, I was terrified.
Fresh from an IT background, I knew the technology inside and out, but standing in front of a room full of professionals? That was different.
I developed my first “vulnerability story” by accident. During a Windows basics class, my hands were shaking so badly that I kept missing the icons I was trying to click.
I abruptly declared, “I am so apprehensive that I am unable to operate this mouse, and I have been using Windows since 3.1!” rather than feigning tranquilly.
The room erupted in laughter. Not mocking laughter—warm, understanding laughter. That moment taught me something about connecting with learners.
Or so I thought.
The Middle Years: Perfecting the Performance
Over the next decade, I built an arsenal of perfectly crafted stories:
- The Great Email Disaster of 2007 (deleted an entire department’s emails)
- The Lotus Notes Nightmare (accidentally sent meeting declines to 500 people)
- The PowerPoint Presentation That Went Wrong (corrupted file in front of the CEO)
- The Excel Formula Fiasco (mixed up currencies in a global report)
Each story was true. Each had a perfect arc:
- Establish expertise
- Show human error
- Create tension
- Resolve with a lesson
- End with a laugh.
I knew exactly when to deploy each story:
- Email disaster for Outlook training
- Lotus Notes tale for system migration classes
- PowerPoint story for presentation skills courses
- Excel mishap for spreadsheet training
They worked beautifully. Too beautifully.
The Coffee Break Revelation
It was during the breaks that reality started cracking my perfectly constructed façade.
While my classroom performance earned high ratings, the real connections happened over coffee, away from the projector’s glare.
A CFO once cornered me by the coffee machine, voice low:
“Everyone expects me to be an Excel wizard, but these new Power BI features? I’m lost. My team presents these amazing dashboards, and I nod along, pretending I understand.”
My instinct was to launch into my Excel story.
Instead, I heard myself say, “The new Power BI update last week changed the interface again. I spent two hours this morning trying to figure out the new features before class.”
His relief was palpable. We spent the break talking about the pace of technological change and the pressure to always appear competent.
No polished stories, just real talk.
The Breaking Point: When Stories Weren’t Enough
The Classroom That Changed Everything
While teaching a Microsoft Teams migration course to a pharmaceutical company, something snapped.
A senior scientist raised her hand during my standard Teams introduction.
“I hate video calls,” she said bluntly. “I’ve been avoiding them for two years by claiming my camera’s broken. Everyone’s talking about Teams backgrounds and video filters, but I just feel… old. Lost.”
My hand instinctively reached for my “video call disaster” story. But looking at her face—the raw honesty there—I couldn’t do it. Instead, I closed my PowerPoint.
“Can I tell you what happened this morning?” I said. “I was testing Teams’ new background effects, and my face disappeared completely. Just… gone. I still don’t know what setting I messed up. And you know what? Every update makes me nervous too.”
The energy in the room shifted. Other hands went up. Real stories emerged:
- A manager admitted crying after a failed video presentation.
- An IT professional confessed to using his phone for Teams because the desktop version overwhelmed him.
- A young graduate shared her panic about looking unprofessional in home video calls.
The Power of Present-Tense Vulnerability
That session transformed my approach to training. I started sharing current struggles:
- My confusion about SharePoint’s new navigation
- The Teams feature that still baffled me
- My daily battle with Outlook’s focused inbox
- The Excel function I learned from yesterday’s class
The impact was immediate and profound.
In Technical Training:
- Questions became more specific and honest.
- Learners started helping each other more.
- Problem-solving became collaborative.
- Learning speeds increased noticeably.
During Breaks:
- Conversations deepened beyond surface issues.
- Real technical fears emerged.
- Peer learning flourished
- Support networks formed naturally.
The Coffee Break Chronicles
The Real Learning Happened Over Coffee
I started documenting these informal moments:
Monday Morning Coffee Breaks:
- Senior executives admitting basic tech struggles.
- Team leaders sharing software migration fears.
- IT professionals revealing update anxieties.
- New employees asking “stupid” questions they feared asking in class.
Lunch Break Revelations:
- Small groups working through real problems
- Peer mentoring emerging naturally.
- Cross-department solutions being shared.
- Informal support networks forming.
The Power of Unstructured Time
I began building more breaks into my sessions:
- 15-minute coffee discussions between modules.
- Extended lunch periods for problem-solving.
- Pre-class informal chat times.
- Post-class Q&A sessions.
The New Training Approach
Restructured Classes Now Included:
- Open discussion about current tech challenges.
- Shared problem-solving sessions.
- Real-time troubleshooting of actual issues.
- Vulnerability circles where everyone shared current struggles.
Modified Teaching Methods:
- Less presentation, more conversation.
- Fewer slides, more live demonstrations.
- Reduced theory, increased practical application.
- More break-time for informal learning.
Got Questions?
How did you maintain control when being vulnerable about current challenges?
Structure remains important. I framed uncertainties as learning opportunities while maintaining clear learning objectives.
What happened when learners knew more than you about certain features?
I celebrated it! “Please show us how you solved that” became a powerful teaching moment.
How did you handle technology failures during class?
I used them as real-time learning opportunities. Nothing teaches troubleshooting like actual problems.
What about learners who preferred traditional instruction?
I balanced vulnerability with structured learning, ensuring technical content remained robust while keeping human connection strong.
How did you manage time when allowing for more organic discussions?
I built flexibility into lesson plans, ensuring core competencies were covered while allowing space for natural learning moments.
Wrapping Up
Fifteen years of technical training taught me that true learning happens in the gaps between slides, in the moments when pretence falls away.
My carefully crafted vulnerability stories served their purpose, but real connection came from present-tense honesty.
Then, when I stood before a new class, I still told stories. But they were today’s stories—raw, unfinished, real.
Because in technology training, just like in technology itself, the only constant is change.
And admitting we were all figuring it out together? That was the most powerful teaching tool of all.
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