· Letter

LBW: The Hard Truth About Leadership & Friendship

Sid Jashnani, CEO of Outgrow and Outgrow Certified Advisor

Being liked feels good. Being respected gets results

Originally published on Substack (opens in a new tab). Subscribe (opens in a new tab) for the next letter.

So there I was, sitting across from a founder who’d built a $3.5M business from scratch. Smart, driven, and utterly miserable.

“What’s the biggest problem in your business right now?” I asked.

His answer? “No one does what they’re supposed to do unless I micromanage them.”

As we dug deeper, the real issue emerged: He was trapped in the friendship zone with his entire leadership team.

The Friendship Trap

Here’s a confession: I’ve fallen into this trap myself (multiple times, because I’m a slow learner).

At Momentum Group, I once had a senior VP who:

  • Missed deadlines regularly

  • Delivered subpar work

  • Created team drama

And what did I do? Schedule “feedback sessions” that turned into friendly chats about sports, family, and weekend plans. We’d end with vague promises to “do better next time.”

Guess what happened? Nothing improved. For months.

Why? Because I prioritised being liked over being respected.

The Accountability Problem

Patrick Lencioni nails it in his book “The Five Temptations of a CEO” when he identifies one of the deadliest leadership sins:

“Wanting to be popular with your direct reports instead of holding them accountable.”

This isn’t just a rookie mistake—it’s an epidemic among even seasoned leaders.

The hard truth: Your job isn’t to be their friend. It’s to help them become their best.

And sometimes, that means having uncomfortable conversations.

Signs You’re Too Deep in the Friendship Zone:

  • You avoid giving negative feedback

  • You let deadlines slide without consequences

  • You spend more time talking about personal life than performance

  • You worry about “hurting feelings” when discussing work issues

  • You have the same improvement conversation multiple times

Sound familiar? Don’t worry, you’re in good company (mine).

The Reset Button

After watching my business suffer, I finally hit reset:

  • Clear Expectations: I documented exactly what success looked like for each role

  • Regular Check-ins: Scheduled weekly one-on-ones focused primarily on metrics and goals

  • Direct Feedback: Delivered within 24 hours, good or bad

  • Real Consequences: Made it clear that continued underperformance wasn’t an option

The results? Two team members stepped up dramatically. One chose to leave. And my business grew 28% the following year.

Finding Balance

This doesn’t mean becoming a cold, distant boss. In fact, the best leader-team relationships involve:

  • Genuine care for your people’s growth

  • Deep understanding of their strengths and weaknesses

  • Investment in their development

  • Respectful, direct communication

As one of my mentors put it: “Be friendly, not friends.”

The Bottom Line

The kindest thing you can do for your team isn’t protecting their feelings—it’s helping them grow through honest feedback and clear expectations.

Your team doesn’t need another friend. They need a leader.

Until next week,

Sid

P.S. What’s your experience with this balance? Reply and let me know—I read every response.

Know a leader struggling with this balance? Forward this email. They’ll either thank you or never speak to you again. Either way, problem solved!

Originally published on Substack (opens in a new tab). Subscribe (opens in a new tab) for the next letter.

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