Recently, some clients of mine asked to work with someone else...
At first, I was totally pissed… Everything felt like it was going great.
I scheduled the meetings, led the kickoff, sent the recaps and asked thoughtful questions like a responsible adult with excellent organizational skills and at least 14 browser tabs open at all times.
Contrary to popular belief, alignment happens more than once, so we’d meet again. I’d explain something. Everyone would nod and we’d go through all the things…
- Clarify requirements – Check
- Document action items – Check
- Build timelines – Check
- Send follow-up emails with bullet points so clean and detailed they deserved literary recognition – Check
That's when things got weird.
Without warning, meetings started to end with everyone confused in entirely new and different ways. At first, I thought maybe I need to explain things differently. So, I did what most of us would do and tried to fix it.
I explained things with wireframes, helped with copy, annotated screenshots… I even started recording meetings so I could play them back to make sure I wasn’t the one missing something. At one point, I’m pretty sure I had enough supporting documentation to survive federal court. I mean, we’re talking:
- Meeting notes
- Follow-up notes
- Backup notes
- Visual diagrams
- Copy examples
- Color-coded timelines
The project started feeling like four people trying to assemble IKEA furniture without instructions… While insisting they understood the instructions, only to start asking questions about some other piece of furniture we weren’t even working on!
The harder I tried to make it make sense, the more obvious it became that it just wasn't going to.
… and honestly? That realization was weirdly hard for me.
To add insult to injury, they turn around and email my boss to say, “She SUCKS, and we hate working with her!”
Okay, maybe not those exact words, but that’s how it felt!
I started wondering what I did wrong, and began carrying responsibility that wasn’t even mine! Instantly I thought:
- Maybe I need to communicate better?
- Maybe I need to be more proactive?
- Maybe I need more visuals?
- Maybe I should summarize the summary of the summary?!
At some point, my boss finally pulled me aside and basically said:
“Sylvia… you’re doing entirely too much.”
She was right, but the truth is that if you’re a Project Manager, (especially one who genuinely cares), your first instinct is usually, “Okay, what else can I do to fix this?”
Not every difficult project is failing because someone is bad at their job.
- Sometimes communication styles don’t match.
- Sometimes expectations never fully align.
- Sometimes personalities just don’t click no matter how hard you try to force it.
That was the uncomfortable lesson: Effort alone cannot create alignment, and oddly enough, learning that was a relief!
Once I got over my butt-hurt of them not wanting to work with me anymore and stopped treating the project like a hostage negotiation, I realized that being a good Project Manager does not mean you can magically make everything perfect all the time.
Some projects flow effortlessly.
Some require structure and patience.
Others feel like trying to parallel park a shopping cart with a missing wheel.
That doesn’t automatically mean anyone failed.
Sometimes the most professional thing you can do is recognize when forcing it harder is actually making it worse.
Still though… If I ever start recording meetings again, someone should probably check on me immediately.


