Every Wednesday at 6 PM Central, I log into a video call that isn’t on anyone’s calendar by mandate. No one’s required to show up. No one gets in trouble for skipping it. And in 10 months, we’ve never missed a session , and never had zero attendance.
This is the story of how an after-hours career development call became one of the most valuable things I’ve built as a technology leader , and it has nothing to do with infrastructure.
In This Post
- Why I Started It. The employee who sparked the idea
- The Format , How we run it
- The First Misstep. What happened when we tried structured curriculum
- What We Talk About , Topics that keep people coming back
- The Numbers , 10 months of metrics
- Building Something That Outlasts You. The three-host model
- What I’ve Learned , Early leadership lessons
- How to Build Your Own , Six recommendations
Why I Started It
It started with one employee. He came to me asking for a raise and wanted to move up in the organization. The problem was that his skill set didn’t match where he thought he was. He was doing good work at his current level, but the gap between where he was and where he wanted to be was significant , and he couldn’t see it.
I wanted to help him close that gap. Not just get a raise, but earn a new title , because in my experience, that’s how real career progression works. You don’t negotiate your way to a 30% salary increase in the same role. You grow into a position that commands it. Your compensation follows your contribution level, not your ambition.
So I spent months working with him during our one-on-ones, trying to get him to engage with extracurricular learning outside of our regular conversations. He never took me up on it. But the idea of career development had taken root in my head. If structured mentorship would be good for him, it would be good for all of us , including me.
That idea rattled around for three to six months before I did anything with it. Then I pitched it to my number two. He loved it immediately. He pitched it to his number two. Same reaction. The three of us decided: we’ll show up on Wednesday nights, and if anyone comes, great. If they don’t, at least we tried.
But we needed someone to show up. The employee I’d originally built this for never volunteered , and I was adamant that participation had to be voluntary. You volunteer your time, we volunteer ours, and both sides get value from the exchange. So we waited. Two months. Maybe three.
Then a junior IT team member , someone who was vocal about wanting to grow his career , said he’d be interested. We asked if he’d show up on a Wednesday night to talk about career advancement. He said absolutely.
That first night, five or six people showed up. No formal agenda, no itinerary, no slides. Just an open conversation about careers , what it takes to be good at this job, what it takes to move forward. And it started to gain organic traction from there.
The Format
The call runs every Wednesday from 6:00 to 8:00 PM Central Time , deliberately scheduled to be accessible to team members on both the East and West coasts. It’s completely voluntary. No attendance tracking, no manager follow-ups, no pressure. You show up because you want to, or you don’t.
I didn’t want to be the single point of failure, so I built a hosting team from the start. My number two and their number two serve as co-hosts, which means there are always three of us available to run the session. If I’m traveling, the call happens. If two of us are out, the call still happens. Between PTO, vacations, office emergencies, and family emergencies, the three-person model means we’ve never had a session without a host. In 10 months, it’s never been canceled.
We started without any agenda at all and have been gradually adding more structure , semi-formal topics with large blocks of open time. We leave plenty of room for questions, and the conversations often go wherever the group needs them to go. The three of us naturally rotate who leads. Sometimes one of us has a particular strength in that week’s topic and takes the entire session. Other times we riff off each other, interjecting different perspectives. It runs on Teams , audio and video, though video is optional. The format is conversational, not lecture-style.
The First Misstep
Not everything we tried worked. About six months in, we started a structured series of classes to walk through the CompTIA A+ curriculum. The idea was solid , help team members who didn’t have their A+ get certified. But teaching dry certification content to a mixed audience turned out to be a mistake. The people who already had the knowledge found it boring, and attendance dropped dramatically over three to four months.
So we pivoted. Dropped the structured coursework and went back to what had been working: soft skills, networking deep dives, open-ended discussions, and guest speakers. The A+ experiment wasn’t a total loss , two employees did earn their certification because of those sessions , but it taught us something important.
Curriculum kills conversation. Both have value, but they don’t belong in the same container.
The moment we shifted from “class” back to “conversation,” engagement came back. Lesson learned.
What We Talk About
The topics span the full spectrum of what it means to work in IT:
Hard skills: Networking fundamentals, Linux, troubleshooting methodology, cloud architecture, security concepts. The kind of hands-on technical knowledge that makes people better at their jobs today.
Career advancement: Certifications , which ones matter, which ones don’t. How to prepare for interviews. How to have a career conversation with your manager. How to know when it’s time to move on.
Soft skills: Time management, prioritization, communication with non-technical stakeholders. Work-life balance in an always-on industry. How to navigate organizational politics without losing your integrity.
Real talk: The stuff that doesn’t fit neatly into any category. Imposter syndrome. Burnout. What it’s actually like to manage people. The things everyone’s thinking about but rarely says out loud at work.
The topics that generated the most engagement surprised me. Networking was a consistent winner , even I got sharper when we brought in our senior network engineers. It turns out that everyone, from junior techs to systems administrators, wants to better understand the network they work on every day. When your systems guy is troubleshooting VLAN issues, he wants to understand VLANs, not just submit a ticket to the network team. Linux was another huge draw for the same reason , practical knowledge that the team could apply immediately.
But the biggest surprise? They just wanted to talk. Between the three hosts, we bring a combined 80 years of IT experience. What people valued most wasn’t any specific curriculum , it was access. Access to perspectives they don’t get in their day-to-day roles. That’s what keeps them coming back.
The Numbers
I’m a data person, so let me share the metrics:
- Duration: 10 months and counting
- Frequency: Weekly, every Wednesday
- Cancellations: Zero
- Sessions with zero attendance: Zero
- Regular participants: 10–15 per session
- Peak attendance: ~50 (guest speaker session)
- Total team eligible: ~100
- Certifications earned: 2 (CompTIA A+)
Building Something That Outlasts You
One decision I made early was critical: this couldn’t be “Craig’s call.” If it depended on one person, it was fragile. So I designed a three-person hosting model from day one.
My number two brings a different perspective and a different relationship with the team. Their number two adds a third viewpoint and represents the next generation of leadership. Between the three of us, we cover different areas of expertise, different communication styles, and different levels of organizational proximity to the individual contributors.
In practice, any of us can lead any session. All three have run entire sessions solo when the others weren’t available. Sometimes one person has a particular strength in that session’s topic and naturally takes the lead. The rotation keeps it fresh for the attendees and prevents any single host from burning out.
This is the same principle I apply to infrastructure design: eliminate single points of failure. A mentorship program that dies when the founder leaves isn’t a program , it’s a dependency.
What I’ve Learned
Ten months of running this call has already taught me more about leadership than most management training programs:
People will show up if you create the right space. The “voluntary” part is what makes it work. When people attend because they choose to, the conversations are genuine. There’s no posturing, no performing for a manager. Just honest professional development.
Mid-career engineers are navigating a fundamental shift. The conversations about AI, automation, and the future of IT roles are more urgent and more nuanced than what you see in conference keynotes. These are people with 10-15 years of experience asking real questions about how their careers evolve when the tools change this fast.
The soft skills hunger is real. I expected the technical topics to dominate. They don’t. Some of our best sessions have been about communication, career transitions, and work-life balance. There’s a massive gap between what IT professionals need and what they typically get from their organizations.
Curriculum kills conversation. Our A+ certification experiment proved that structured coursework and organic professional development are two different things. The moment we shifted from “class” to “conversation,” engagement came back.
How to Build Your Own
If you’re a technology leader thinking about starting something similar, here’s what I’d recommend based on 10 months of doing it:
- Make it voluntary. The moment it becomes mandatory, the dynamic changes entirely. Attendance might be higher, but engagement will be lower.
- Schedule for accessibility. We chose 6 PM Central specifically to work for both coasts. Think about your team’s distribution and find the window that excludes the fewest people.
- Build a hosting team. Don’t make it dependent on one person. Three hosts means the call survives vacations, travel, and eventually your departure.
- Mix topics intentionally. Alternate between hard skills, career development, and real talk. The variety keeps people coming back and makes the call feel like a community, not a class.
- Invite up, not just down. Getting executives to participate sends a message: leadership takes this seriously. It also gives individual contributors a rare chance to interact with senior leaders in an informal setting.
- Be patient. Our first sessions were small. Consistency builds trust. If you’re still running it after three months, people notice.
What’s Next
We’re 10 months in and still going every week. The attendance is steady, the conversations keep getting better, and we’re starting to see real outcomes , certifications earned, cross-team relationships forming, and a shared sense that professional development isn’t just HR’s job. It’s ours.
I’m curious to see where this goes. Will we need to change the format? Adjust the cadence? Bring in guest speakers from outside the organization? I don’t know yet. But I do know that the three of us will keep showing up on Wednesday nights. Because the team keeps showing up too.
I’ll write an update when we hit the one-year mark. Stay tuned.
Craig Corbin is an IT executive with 30+ years of progressive leadership spanning military operations, enterprise hospitality, and maritime fleet technology. He writes about building teams and systems at craigcorbin.com.