Where AI Helps—and Where It Doesn't Yet

Ever wonder why some high performers skyrocket while others stay stuck in middle management hell?

Brian teams up with career coach Kendall Berg, who cracked the code after getting promoted five times in six years—and it wasn't by working harder. This conversation gets uncomfortably real about workplace politics, invisible performance reviews, and why your boss probably has zero clue about your actual contributions. Kendall opens up about her journey from being "too direct, too stubborn, too emotional" to mastering the unspoken rules that actually drive promotions, while Brian shares his AI trick that instantly reveals whether you're delegating like a pro or driving your team crazy.

You'll walk away with immediately usable tactics: the magic of investing 20% of your time in relationships, how to handle "urgent" requests without becoming a pushover, and the email structure that makes people think you're incredibly thoughtful. Plus, they pull back the curtain on what really happens in those executive rooms where promotion decisions get made—and why knowing your boss's peers might be more important than impressing your boss.

If you're exhausted from working endless hours without advancement, confused by office politics, or ready to stop waiting for someone to notice your hard work, this episode reveals the strategic moves that separate the promoted from the passed-over.

Ready to level up? Dive into the resources and links waiting in the show notes!

References In This Episode

Kendall Berg – “That Career Coach” – Kendall’s website and LinkedIn profile

Books Mentioned:

Secrets of the Career Game – Kendall’s book with 36 strategies to help high performers move up in their careers.

The Extraordinary Leader: Turning Good Managers into Great Leaders– book by John Zenger and Joseph Folkman, recommended during the episode.

Concepts & Frameworks:

Nine Box performance evaluation system

Cross calibrations/Performance calibrations meetings

3-2-1 backup strategy (mentioned in context)

CORE delegation framework (Context, Oversight, Resources, Expectation)

ARS email template (Acknowledge, Restate, Solve)

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Chapters

00:00 Introduction to Productivity Skills for Promotions

02:59 Kendall's Unique Approach to Career Coaching

05:25 The Gap Between High Performers and Stagnation

08:28 Understanding Performance Reviews and Visibility

10:55 Navigating Urgency and Productivity

13:17 Effective Networking and Relationship Building

16:16 Planning and Structuring Your Work Week

18:56 The Importance of Strategy in Career Advancement

30:23 The Importance of Automation and Goal Setting

32:37 Effective Communication in Management

35:52 Delegation and AI: A New Era of Productivity

41:00 Communication Habits for Career Advancement

54:36 Navigating the Career Game: Insights from Kendall's Book

Today’s Guest

Kendall Berg

Career Coach, Leadership Development Expert, Corporate Strategy Consultant

Kendall Berg is a career strategist and executive coach who transforms high-performing professionals into promotion-ready leaders. After struggling with workplace politics early in her career—being "too direct, too stubborn, too emotional"—she developed tactical systems that propelled her through five promotions in six years, culminating in a CFO offer before age 30.

Her book, Secrets of the Career Game: 36 Strategies to Get Ahead in Your Career, serves as a no-nonsense tactical guide for navigating corporate realities. Kendall specializes in helping middle managers break through to executive levels by mastering the unspoken rules of workplace advancement, relationship building, and strategic communication.

Known for her refreshingly honest approach, Kendall doesn't sugarcoat corporate life or pretend workplaces are meritocracies. Instead, she equips clients with concrete templates, scripts, and frameworks to advocate for themselves effectively while staying authentic. She believes career success isn't about working harder—it's about working strategically and building the right relationships.

Currently balancing her coaching practice with a corporate role (because her boss "refuses to let her go"), Kendall brings real-world credibility to her advice. She's the coach for professionals tired of playing games they don't understand.

Connect with Kendall:

LinkedIn: Kendall Berg

Website: thatcareercoach.net

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About The Creator/Host: I’m Brian. At age 4, I was diagnosed with insulin dependent (type 1) diabetes and told that my life was going to be 10-20 years shorter than everyone else. As a kid I took time for granted, but now as an adult, time is the most precious thing that I have. After spending a career hands-on in the trenches as a leader at all levels, I now train Productivity Gladiators to level up their careers. Graduates wield superpowers in time management, practical leadership, communication, & productivity. If what you’ve seen here intrigues you, reach out, let’s chat!

“Time is the currency of your life, spend it wisely.”