The Journey: 15 Unseen, Unsaid, Unknown

I used to think I was that manager—the one everyone trusted.

The cool boss. Like how Regina George's mom thought she was the "Cool Mom". IYKYK.

The one who blurred the lines between manager and friend because we just got each other.

I assumed that if something was wrong, someone would tell me.

And if they didn’t say anything? Clearly, everything was fine.

Spoiler alert: it wasn’t.

I still remember the day one of my best employees asked to chat early one morning. I wasn’t expecting anything out of the ordinary—maybe a quick update on a customer initiative or a casual coffee catch-up.

Instead, she gave me her two weeks’ notice.

I was physically ill.

How could she do this? We were close. We talked all the time. She smiled in meetings, hit her goals, and we talked ALL THE TIME. I thought we were good.

I felt blindsided.

Betrayed.

Like my “friend” had kept secrets from me.

But the truth?I wasn’t her friend. I was her boss.

And I had confused silence with satisfaction, friendship with safety, and perception with reality.

That moment was a wake-up call.

It forced me to confront my own leadership blind spots and rethink how I build trust—not just friendly vibes, but real, meaningful trust.

Here’s how I lead differently today and what I've done over the years that worked:

Skip-Level Meetings

Create space for open conversations beyond your direct reports. Once a month, I meet with team members two levels down to ask how things are going, what’s working, and what’s not. My boss does the same with my direct reports to keep communication flowing both ways.

Anonymous Surveys

Run quarterly anonymous pulse surveys with targeted questions about morale, leadership, and communication. Use tools like Culture Amp, Lattice, or Google Forms. Read every comment, look for patterns, and always follow up—silence is feedback too.

Management 360 Reviews

Have employees review their managers to help uncover blind spots. We run 360s twice a year. Consider using a third-party facilitator to collect and analyze the feedback for full anonymity and transparency. The real gold is in the written responses.

Team Meetings

High, Low, BuffaloIn weekly team meetings, we each share one high, one low, and one random (buffalo) moment. It fosters vulnerability and emotional intelligence. Listen carefully—often, the “low” is where coaching and connection begin.

Consistent 1:1s

Make your 1:1s sacred. Show up, be present, and keep them consistent. Use this time for personal check-ins, not just status updates. Ask: "What’s something I can do to make your week easier?" and "How are you really feeling this week?"

Performance Tracking

Set clear goals and expectations, and track them visibly. Celebrate wins loudly and address issues early. If someone’s performance dips, don’t assume—it’s your cue to check in and offer support. Clarity + empathy is the winning formula.

As a leader, it’s my responsibility to create spaces where people feel safe being honest—even when it’s uncomfortable.

That means listening when they go quiet.

That means paying attention to what isn’t said.

That means showing up every day in ways that build credibility and connection.

Because leadership isn’t just about what you see.It’s about what you’re willing to look for.

What’s something your team might not be telling you?

Leadership starts by asking—and being ready to listen.

And if you want a sobering reality check, just spend five minutes on the Customer Success subreddit.

Every day, hundreds of CSMs vent about their toxic work environments, poor management, and how unseen they feel. It’s heartbreaking—and eye-opening.

I guarantee their managers think everything is fine. Don’t let that be you.