Ah, “CEO Tiffany.” That name takes me back. Not necessarily in a good way, mind you. It reminds me of that one crazy year, must’ve been around 2018 or 2019.
We were working on this big platform migration. Huge deal for the company. Top-down mandate. And Tiffany, she was the driving force, at least on paper. Came in with all this energy, big promises, talking about disruption and synergy… you know the drill.
The Kick-off
I remember the first big meeting. Fancy slides, expensive coffee. Tiffany laid out this grand vision. Sounded amazing, really. But then came the timeline. Utterly nuts. Anyone who’d actually done this kind of work knew it was impossible. But who’s gonna tell the CEO that in a room full of VPs nodding along?
So, we got started. The actual work, I mean. Forget the fancy slides. It was us, the engineers and project managers, stuck in the trenches.
- First thing we did was try to break down her grand vision into actual, doable tasks. Took weeks.
- Then we had to figure out the resources. We needed more people, different tools. Getting approvals was like pulling teeth.
- Communication was a mess. We’d send up reports, detailed risks. They’d come back down filtered through three layers of management, usually simplified to “everything’s green!”
Reality Bites
Tiffany would occasionally swoop in for “updates.” She’d ask these high-level questions that showed she hadn’t really grasped the technical hurdles. We’d try to explain the roadblocks – legacy systems fighting back, unexpected data issues, vendor delays. It felt like talking to a wall sometimes. She just wanted to hear about progress, about hitting those insane milestones.
So, we did what you always do. We found workarounds. We cut corners, maybe promised ourselves we’d fix them later (spoiler: you rarely do). We pulled insane hours. Lots of pizza, lots of caffeine. Team morale was… variable. Some days we felt like commandos on a mission, other days just felt like we were drowning.
I spent most of my time just trying to shield my team from the chaos upstairs. Translating the vague directives into something actionable, pushing back (gently) on the impossible, and making sure we had something to show, even if it wasn’t the perfect thing Tiffany envisioned.
The Landing
Did we launch? Yeah, eventually. Months late, over budget, and with a ton of technical debt we knew would bite us later. Publicly, it was hailed as a success. Tiffany gave another big speech, congratulating everyone. Privately? We were exhausted and knew the platform was shaky.
It stabilized over the next year, mostly because the teams kept patching and fixing things quietly. Tiffany had moved on to her next Big Idea by then.
So, yeah. CEO Tiffany. Reminds me that leadership isn’t just about having a vision. It’s about understanding the messy reality of getting there. It’s about listening to the people doing the actual work. We got it done, but no thanks to the way things were run from the top. It was an experience, alright. Learned a lot about managing upwards and downwards simultaneously.