[Bullet #89] Caring Deeply, Challenging Directly

Issue 89, Double E Bullet, May 16th, 2024

Hey, it’s Dhiren 👋

Have you ever had a friend like Chandler Bing? The one always dishing out sarcastic quips? While hilarious on TV, that approach just doesn’t work in the workplace. But you don’t want to be an overbearing Monica either.

As an aspiring Part-Time CEO, you need to master a delicate balance: Caring deeply about your team, while still keeping them accountable with casual honesty when needed. It’s the philosophy of Kim Scott’s book, Radical Candor - be neither a harsh critic nor a pushover. Find that sweet spot of showing you’ve got their backs, while giving them a loving kick in the ass when they need it.

This week’s rule in the continuing series is about Caring Deeply, Challenging Directly; Ready to learn how to strike this balance and level up from full time founder to Part-Time CEO? Let’s go…

P.S - The first two rules incase you missed them are linked below

BULLET ONE
🧠 Care Deeply...

Just like the tight-knit group of friends on Friends, your team needs to know you genuinely support them. When you care deeply, you create an environment of trust and psychological safety, where people feel comfortable taking risks, sharing ideas, and admitting mistakes. One of Radical Candor’s core lessons is “Care personally and mean it” - be truly present and available when your team needs you.

Here’s three ways you can show and practice Caring Deeply

  1. Get radically transparent: In the book, Scott emphasizes the importance of open and honest communication as a way to build trust and show you care. This means going beyond surface-level conversations and having authentic dialogues where you share your own vulnerabilities, fears, and growth areas as a leader. When founders get radically transparent, it creates a culture of psychological safety where team members feel comfortable being equally open.
  2. Put a spotlight on success: One unique way Scott suggests caring deeply is through liberal and specific praise. Too often, leaders focus more on areas for improvement than celebrating wins. Make a conscious effort to call out specific achievements, successful projects, or excellent work from individuals in public settings. This public recognition shows you’re paying close attention and taking pride in your team’s successes.
  3. Have their backs, especially when they really mess up: True care, according to Radical Candor, means going to bat for your team even when they really drop the ball. Rather than blaming or shaming after a major failure, have frank conversations to understand what went wrong, but make it clear you still believe in them and are committed to their growth. Extend them public reassurance that you have their back as they work to bounce back stronger.

BULLET TWO
🧠 Challenge Directly

While caring deeply is essential, it is equally important to challenge your team directly when necessary. Consider how Monica from Friends would often call out her friends' questionable behavior or poor decisions. She did this not just as a friend but because she truly cared about their well-being and growth.

As a Part-Time CEO, your role involves providing honest and direct feedback, even when it's uncomfortable. However, unlike Monica, your relationship with your team is not based on friendship. It’s crucial to avoid sugarcoating or shying away from difficult conversations.

Here’s three ways you can show and practice Caring Deeply

  • Give specific, actionable feedback: Don’t beat around the bush. Provide clear, direct feedback on areas that need improvement, backed by specific examples and a plan for addressing the issues.
  • Set high standards: Challenge your team to continuously raise the bar and strive for excellence. Push them to think critically, question assumptions, and go beyond their comfort zones.
  • Hold them accountable: Follow up on commitments and deadlines, and have tough conversations when expectations are not met. However, approach these conversations with empathy and a solutions-oriented mindset, not just criticism.

🧨 DHIREN'S UPDATES 🧨

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Last Word 👋

How Am I Doing ?
I love hearing from readers, and I'm always looking for feedback. How am I doing with the Double E Bullet? Is there anything you'd like to see more of or less of ? Which aspect of the newsletter do you enjoy the most ?


Much love,

Dhiren Bhatia
Founder, Elevated Entrepreneur
ElevatedEntrepreneur.co
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