28/12/2025
A few years ago, I walked into an ambush at work.
The entire legal team was invited to a meeting from a department I supported.
I was suspicious because I had been clashing with one person from that department – high-demand, high-drama, let’s call him Person X. We were butting heads over redlines and weren’t exactly on good terms.
We walked into the meeting room, and there’s the VP of the department, the team leader, and Person X.
Pleasantries.
Then, for the next 20-30 minutes, they went through each task that Person X had sent my way and the time taken to close each agreement. The numbers didn’t paint me in a good light.
No context about delays – no mention of counterparty pushbacks, Person X’s delays, or the bottlenecks outside my control. It was just numbers.
I glanced at my boss and the other team members. They were sitting there, silent. My boss, someone I deeply respected, stayed silent for most of it.
I was humiliated. Blindsided. I had no idea that this was coming.
The most frustrating part? Nothing came out of it. No change to respond, no discussions on optimizing processes. They left no time for that. It was just a 20-30 minute complaint session beautifully presented on Powerpoint!
I wondered about the time and effort it must have taken to prepare the PPT compared to just speaking to me directly. But they didn’t and that was on me!
There were 2 issues.
#1 Person X - it wasn’t just about redlines – it was how he saw the role of legal. Person X came from a smaller startup without a legal department. He was in sales, incredibly assertive, and wasn’t used to having legal involved, let alone push back on him.
#2 Me - I didn’t have the self-awareness to see the bigger picture, and I got sucked into the clash. I could have handled it better. I didn’t create an environment where he felt he could give me feedback directly. I take some responsibility for that (not all).
After that meeting, we had a smaller one, where I went through the agreements and explained the issues causing the delays. That was an eye-opener for Person X – he hadn’t realized the risks involved.
Soon after, I noticed that when he sent agreements to me, he had already set expectations with the other side about the provisions we couldn’t accept. He ended up doing a significant part of the heavy lifting for me, and it saved a lot of time and friction.
Here’s what I took away:
1. Head things off early. If there is friction with an internal client, grab a coffee and have an open conversation (leave you ego at the door).
2. Sometimes, confrontations and escalations are necessary to course-correct. But try and keep the volume down and keep it collaborative.
3. Support Your Team: If you’re a manager, don’t let your team walk into the firing line alone. If you’re not the boss, reach out to your manager beforehand if a situation seems off.
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