The Most Useful Project I was Assigned (And It’s Shockingly Simple)
When I stepped down from my Vice President / General Manager role, ownership gave me one final assignment:
“Please make a monthly timeline of the team’s operations.”
Simple enough, right?
That’s what I thought—until I actually sat down to do it.
Within minutes, it hit me:
Our entire operational rhythm lived in people’s heads.
Mine. My directors’. A few long-time staff members’.
But nowhere—nowhere—was it written down.
Season Seat invoices went out in early August… because that’s when they always went out.
We got our league schedule in October (well—usually), so that’s when we sent it out to fans and sponsors.
Individual tickets went on sale the first week of May… because they just did.
None of it was documented.
It just existed.
Unspoken. Inherited. Tribal knowledge at its finest.
And trying to turn that into a clean, logical, repeatable timeline?
Absolutely brutal.
But it taught me something every leader, every manager, and every department head should keep front of mind:
If your operational knowledge only lives in your team’s memories, you’re one staffing change away from chaos.
So how do you prepare for that scenario—before you’re asked to produce the whole thing at once?
Here’s what I wish I had done proactively (and what I recommend for anyone in a similar role):
1. Document the “why,” not just the “when.”
It’s easy to say, “We do X in August.”
But why August?
What triggers it?
What needs to happen before it?
What does it impact after?
Those answers matter far more than the date.
When you understand the logic, you can adjust the timeline anytime the environment changes—which it will.
2. Build a “living operations calendar,” not an annual chore
The worst way to build an operational timeline is all at once.
The best way?
Add to it as the year unfolds.
During invoice season? Capture it.
Schedule release? Capture it.
Ticket sales prep? Capture it.
Do it while the context is fresh.
Future you will appreciate the accuracy.
Your successor will build a shrine in your honor.
3. Ask your team what they assume everyone knows
This was one of my biggest discoveries.
I’d ask a director, “Why do we send this out now?”
And they’d shrug: “Because we always have.”
That’s when you know you’ve hit undocumented territory.
Have these conversations early.
You’ll uncover a lot of invisible processes that need to be captured.
4. Look for the dependencies no one talks about
Some tasks weren’t tied to dates—they were tied to events:
“When the league sends X…”
“After sponsor renewals hit 80%…”
“Once the schedule is approved…”
These are the landmines of an operations timeline.
Document them clearly so someone new can understand the sequence.
5. Treat operational knowledge like an asset—not folklore
If your organization would collapse for a month if one key person left, that’s a risk.
Documenting operations isn’t bureaucracy—it’s risk management.
And it protects the team, not just the leader.
The big lesson?
When ownership asked for a “simple monthly timeline,” what they were really asking for was the blueprint of our organizational memory.
It turns out we didn’t have one.
And building it retrospectively was one of the most time-consuming projects of my career—not because the work was complicated, but because it was scattered across conversations, habits, routines, and assumptions.
If you’re in a leadership role today, my advice is simple:
Start building the operational timeline now, long before someone asks for it.
Do it piece by piece.
Capture everything while it’s fresh.
And make it a living document, not a once-a-year artifact.
Your future self—and the person who eventually takes your seat—will thank you.
At GameDay Advising, we help sports organizations build structured systems and operational plans that prepare staff and teams for the worst - and the best.
