Two Weeks In, One Mistake Nearly Cost Me My New Job

When managing people, there's a fine line between being direct and being seen as aggressive.

I know this because I crossed that line - many times.

It was 2016, and I'd just joined LinkedIn Sales Solutions.

I was 32 years old, starting my very first corporate job. I wasn't exactly young, but I wasn't seasoned in this world either.

LinkedIn flew me to San Francisco for onboarding, a week-long, intensive training session with 20 or 30 other new hires from around the globe.

I'd never seen anything like LinkedIn's onboarding.

It was structured, thorough, and honestly, a little overwhelming.

Every day was packed with meetings, role-plays, and exercises.

By evening, we'd be assigned "homework" to prepare for the next day.

It was a lot for someone who'd never worked in such a company.

On the final day, we had to do a role-play. My task was to run a renewal discussion with someone I assumed was a facilitator.

I'd never done a role-play before.

But instead of slowing down, I pushed through, trying hard to close the "deal." I was intense, rough, and unstructured.

The feedback came in quickly - first from my group and then from the person I'd role-played with.

I knew it hadn't gone well, but I didn't understand how bad it was until I returned to Dublin the following Monday.

My manager called me into a room and asked, "What happened during the role-play in San Francisco?".

I felt my stomach drop.

It turned out that the person I'd role-played with wasn't a facilitator.

He wasn't just some training expert. He was a senior sales director - one of the most influential people in LinkedIn's US sales team.

And his feedback? He thought I was a bad hire. Too aggressive, unprepared, and rough around the edges.

I was stunned.

My manager barely knew me, but thankfully, he saw something worth keeping.

He recognized that I wasn't yet familiar with corporate culture, let alone American tech culture.

I was passionate, yes, but I was also unpolished. My English was clunky, and my directness came off as abrasiveness.

And here's the truth: that aggressiveness has been a constant companion in my life.

It's easy to say it's because I'm passionate, but I sometimes struggle to control my emotions.

Over the years, I've learned that there's a fragile line between being perceived as passionate and being perceived as aggressive.

This lesson has shaped the way I lead and give feedback.

Today, I manage people, and I've read books like Radical Candor to help me walk that line more carefully.

I love coaching, mentoring, and watching people grow.

But I also know that feedback can come in a hundred different ways.

My responsibility as a leader is to ensure that my feedback is clear, constructive, and actionable - never harsh or destructive.

Walking this line isn't easy. It's a constant internal struggle, especially for someone with my background.

But I believe in growth for myself and those I lead.

As leaders, it's our job to communicate in a way that lifts people, not pushes them down.

Because, ultimately, it's all about walking that line between being challenged directly and caring personally.

It's our job to create ripples of radical candor.

Thank you for reading this far, see you all next week, same time, same inbox.

Previous
Previous

131 founders. 300 conversations. 74 contracts won. Here’s what I’ve learned about building and scaling sales teams.

Next
Next

Create Pipeline, Move Pipeline, Close Pipeline