#123 Kendall Berg: Secrets of the Career Game
Kendall Berg is a career strategist and author of Secrets of the Career Game who helps ambitious professionals navigate corporate politics with integrity and transform strong performance into visible, undeniable value. After being told early in her career that "everybody loves having you on their team, but nobody likes working with you," she dedicated herself to learning the unspoken rules of advancement—and was promoted five times in six years. Now, through her coaching practice and her tactical, no-nonsense approach, Kendall teaches thousands of clients across 27 countries how to earn more, advance faster, and feel in control of their career trajectory without burning out or losing themselves in the process.
In this episode, you'll discover:
Why your boss has NO idea what you're actually doing—and the weekly habit that fixes this blind spot
The one person you must talk to during interviews that reveals the REAL company culture (hint: it's not the hiring manager)
How asking for help makes people think MORE highly of you—the counterintuitive psychology that changes everything
The "influencer list" strategy: Why you're networking with the wrong people and how to identify the 5 who actually control your career
Why 82% of jobs are filled before they ever hit the job board—and what to do about it
Time-Stamped Show Notes
[00:00] Introduction & Book Feedback
Initial response to Secrets of the Career Game
Why the book is written as a tactical textbook, not theory
The importance of actionable advice readers can implement immediately
[03:15] Interviews That Stand Out
Discussing the unspoken rules and corporate politics
Navigating interpersonal conflict and toxic coworkers
The mental load of difficult workplace relationships
When survival mode is the only option
[07:30] Kendall's Origin Story
Growing up with a tech sales father who made her do business cases for everything
Learning to communicate ROI from childhood
Studying mathematics and economics
Starting career as a data scientist and analyst
The skill that mattered most: communication
[12:45] Lessons from Parents
Mom's philosophy: "You might as well try it"
Getting out of your own way
Failure as the start of something new, not the end
Starting businesses early and learning from failure
The importance of persistence over perfection
[17:20] Moving 20+ Times Before High School
Attending four elementary schools, two middle schools, two high schools
All within a 5-8 mile radius
How constant change built adaptability
Learning to build relationships quickly
The one move Kendall requested herself
[22:40] The Inflection Point to Career Coaching
The VP who told her: "Everybody loves having you on their team, but nobody likes working with you"
Choosing growth over defensiveness
Meeting with female mentor Allison
The transformative advice: spend 2-3 minutes on small talk
Getting promoted 5 times in 6 years
[28:15] The CFO Job She Turned Down
Being offered a CFO position at 29, six weeks after having her daughter
Why her "dream job" was actually misaligned
Understanding the difference between title and fulfillment
The importance of self-assessment before accepting roles
When they referenced her age in the offer
[34:00] How to Do Due Diligence on a New Job
The power of talking to a peer, not just the hiring manager
What to ask: promotion timelines, mistake handling, mentorship
Why peers have no incentive to lie to you
Red flag: when companies refuse peer conversations
Asking to speak with 8 peers before accepting her current role
[40:30] The Samsung Interview Story
Four hours of back-to-back interviews
"I sleep 4-5 hours a night"
The "crazy range" salary negotiation tactic
Learning about "dispatchers" who report back to Korea
Choosing culture fit over compensation
[45:20] Ghost Culture vs. Real Culture
What executives think culture is (cereal bars, nap pods)
What employees actually experience day-to-day
The Google commercial that changed corporate perks
Why subcultures matter more than company culture
Your direct manager creates your real experience
[50:45] Building Your Influencer List
Identifying 20 people who have influence over your career
Evaluating them on seniority, power, and "fear factor"
Narrowing down to your top 5
Meeting with 20 executives quarterly on rotation
Why most career conversations happen without you in the room
[57:10] The Client Who Got 6 Job Offers
Three months, 60 coffee chats across 5 target companies
Meeting everyone from janitors to CEOs
Nothing happened during the holidays
February: 6 simultaneous job offers
The power of relationship-first, application-second
[01:01:30] People Who Help You Think More Fondly of You
The umbrella analogy
Why asking for coaching makes others feel invested in you
Overcoming the fear of "bothering" people
Most people feel flattered when asked for help
Breaking the misconception that asking for help is manipulative
[01:06:45] Playing the Career Game with Integrity
Why "playing the game" gets a bad reputation
Learning the rules vs. playing by them
When Kendall chose NOT to falsify financial reports
Understanding the game lets you opt out intentionally
Building authentic relationships that benefit both parties
[01:10:20] The Hard Truth: Your Boss Doesn't Know What You're Doing
The hardest career secret to navigate
Weekly updates are essential, not optional
The balance between educating your boss and seeming haughty
Why visibility matters more than performance alone
[01:12:40] Career Advice for Her 30-Year-Old Self
"The other person is also right"
Getting out of victim mentality
Taking accountability creates emotional distance
Asking: "What are your expectations for me?"
Solving problems by understanding others' perspectives
[01:15:25] The Toxic Boss Who Falsified Reports
Working in finance with ethical dilemmas
Losing confidence in her own capabilities
Almost becoming a high school math teacher
Why she had to live through it to learn from it
The setback that taught her the career game
[01:19:50] Balancing Career Success and Family
There's no such thing as work-life balance
Work and life exist in seasons
The terrible advice: "You can't have everything as a mother"
Establishing boundaries vs. maintaining them
When exceptions become the new boundary
[01:24:30] Trade-Offs and Saying No Constructively
Presenting alternatives instead of just declining
"I can't stay late tonight, but I can be on early tomorrow"
Why most leaders will support your boundaries
The importance of communicating trade-offs
[01:27:15] Self-Care: Paint by Numbers
Finding zone-out activities that work for you
Mother-daughter creative time
Numbers-based creativity for analytical minds
[01:29:00] Book Recommendations
Seven Habits of Highly Effective People (reads annually)
Unspoken Truths for Career Success by Tessa White
How to Win Friends and Influence People (reread this year)
The Sword of Truth series (the reason she got married)
Favorite habit: Listen first and seek to be understood
[01:32:45] Rapid Fire Career Advice
For someone 5 years into their career
Relationships first: build them, keep in touch
Get comfortable with the second-best solution
If someone else's idea solves the problem, roll with it
Collaboration over being "right"
[01:35:20] The Nine Box & Final Thoughts
Every company plots you on a performance chart
Individual contributors never see it
Why transparency would help everyone
The importance of knowing how you're evaluated
Staying connected beyond the interview
Check out Kendall’s website: www.thatcareercoach.net