A witty column about the genuine, emotional, and humorous exploits of coaching elite executives.


The Ultimate Guide To Executive Career Transformation

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Transform Your Career NOW! | The Best Tips From 10k+ Hours Coaching

2022 is sunsetting. For some, it can't come soon enough. And for others? 

Well, they've already missed their recession-blasted targets, are scrambling to reset expectations, and wonder why so much of their compensation is baked into variable performance. 

Regardless, the end of the year never fails to get interesting for those high-performers in the endless pursuit of personal development. I suspect that many folks feel optimistic about what 2023 can bring—but don't know how to get there. 

Fair enough. Self-transformation isn't exactly an "if this, then that" approach. In my ongoing fools-errand to make it so, I'd like to share meaningful progress in the right direction. 

I've identified 4 CORE pillars to help others transform. But of course—then expanded them out to 4 subpoints each—and each of those subpoints probably has another 4 presently known subpoints. 

The moral? Transformation is a bitch. 

Read on for a summary of the current breakdown of the CORE Methodology© and grab a free download for later. I recommend bookmarking or clicking through the slide deck presentation and scanning for the most appropriate resources. If you think I'm missing anything that has significantly impacted your career, I'd love to hear about it. Please email me. 

The First Student CORE Stress Test Is Complete

On Tuesday, I rallied the 6th and final session for our inaugural CORE Career Enablement for Executives course with Pavilion. I'm happy to report that, as with most ambitious undertakings, I've found my ass thoroughly humbled. 

Applying the methodology to individuals in a confidential 1:1 (coaching) environment is notably more-straight forward and personal than presenting to a group.

However, I'd say that the outcome of teaching a group of nearly 150 executives was a success. With a 95% satisfaction score and commentary such as "CORE is a must-take for executives across disciplines." and "Super impactful course!" from executive students—I'd say we're on the right track. 

I also ate a few constructive criticism knuckle sandwiches, for what it's worth. But I'm a scumbag Silicon Valley marketer, first and foremost! How could I face myself if YOU didn't think I was perfect?  

Setting The Stage

If you're a long-time reader of Execs and the City, you may recall that I introduced CORE back in July. The CORE concept is essentially a go-to-market approach for your career. Similar to building and selling a new business—but for yourself. 

While we haven't changed the original pillars—Clarity, Opportunity, Realization, and Empowerment—we have gotten much more specific and expanded sections to help you with a step-by-step approach depending on where you currently sit in your personal journey.

There are 18 friggen' steps that serve as your order of operations! So much for that Silicon Valley marketing background. It turns out that transforming your life isn't full of that seductive instant gratification we've grown to know and love.

  1. Primer: Explore The CORE Methodology©
  2. Clarity: Find Your Why
  3. Clarity: Assess Yourself
  4. Clarity: Evaluate Targets
  5. Clarity: Tell Your Story
  6. Opportunity: Design Your LinkedIn (& Brand)
  7. Opportunity: Build A Networking Army
  8. Opportunity: Refine Your Job Search Habits
  9. Opportunity: Personalize Your Resume
  10. BONUS: Understand Coaches, Hiring Managers, & Recruiters
  11. Realization: Own Your Functional Expertise Interview
  12. Realization: Drive Assertive Behavioral Interviews
  13. Realization: Figure Out Compensation
  14. Realization: Deliver Winning Negotiations
  15. Empowerment: Know Your Greatest Impact
  16. Empowerment: Shred Anxiety & Imposter Syndrome
  17. Empowerment: Establish Your Leadership Style
  18. Empowerment: Always Consider What’s Next For You

I packed learnings from 10,000+ career coaching conversations and 2500+ executive client relationships in the following notes. I also added a step-by-step guide with 100+ aha moments and tips—plus over 30 deep-dive learning resources on how to accelerate any career transition or transformation.

It may not be concise, but this process has worked for hundreds of my clients. You may be a total rockstar and have many of these factors dialed in—but I guarantee that there is something in this for you too.  

So let's dig right into my notes from the presentation. (The download is at the very end). 

PS — If you'd like me to deliver this 90-minute presentation to an executive group that you're in, buzz me an email. 


Clarity Notes


Set CLEAR Intentions

  • Challenge what you want.
  • Learn what you love and loathe.
  • Explore your strengths and weaknesses.
  • Articulate your intentions with your network.
  • Reach for your goals.

Clarity Step #1: Find Your Why

Tip #1: Approach your why with childlike curiosity.
Imagine looking at the world with infinite possibilities. What would you change? (Kids ask why frustratingly often, you should too).

Tip #2: Ask yourself the journalist five (+1).
Who, what, where, when, why, and how.

The Journalist Five

  • Who am I?

  • What do I want?

  • Where do I want to be?

  • When do I want it?

  • Why do I want it?

  • +1: HOW do I get there?

Clarity Step #2: Assess Yourself

Tip #1: The only person putting you first is you.
Nobody understands your career quite as you do. Not your boss, spouse, friends, or otherwise. Be responsible and disciplined for what matters, but don’t lessen yourself.

12 (Stoic) Q’s That Will Change Your Life

  • What is the most important thing? (What do you value?)

  • Who do you spend time with?

  • Is this in my control?

  • What does your ideal day look like?

  • To be or to do? (What can do if you don’t care about the credit?)

  • If I am not for me, who is? If I am only for me, who am I?

  • What am I missing by choosing to worry or be afraid?

  • Are you doing your job?

  • Who is this for?

  • Does this actually matter?

  • Will this be alive time or dead time?

  • Is this who I want to be?

Tip #2: Get a 360-degree view.
Not all opinions of you should be treated equally. Learn from negativity, but brush off the negative energy of statements made about you.

๐Ÿ—ฃ “A lion doesn’t concern itself with the opinion of sheep.” George R.R. Martin

Benefits Of 360 Feedback

  • Increases your self-awareness.

  • Provides strengths and weaknesses assessment from all perspectives.

  • Builds confidence and boosts team morale.

  • Creates a culture of openness.

  • Empowers leaders and teams.

  • Increases accountability.

  • Launching point professional development.

  • Fosters continuous improvement.

    Via EdgeTraining Systems

Further Reading 
๐Ÿ“š Exploring Executive Work/Life Balance & Happiness
๐Ÿ“š Are You Happy? Become A Student Of Yourself
๐Ÿ“š The Dangers of Career Complacency
๐Ÿ“š Your Career Success Makes You Unhappy
๐Ÿ“š Questions That Lead To A More Fulfilling Executive Career

Clarity Step #3: Evaluate Targets

Tip #1 Perception is 9/10 of the law—but only 1/10 of reality.
We share our highlight reels; employers wear their Sunday best. There is always more than meets the eye.

Tip #2: You must create the career you want. You won’t find it.
What got you here won't get you there. Executive roles are in short supply, and the rules are evolving — fast.

Exercise: Write Your Own Job Description

  • Search for the jobs you think you want.
    • Ignore titles, compensation, industries, and company.
  • Copy snippets and bullets that you care most about.
  • Paste your findings into a master document.
  • Evaluate Your “Frankenstein Job Description”
    • Does the role sound familiar?
    • Do you know someone that does this?
    • Have your job titles and responsibilities been accurate?
  • Use these inputs to inform your storytelling.

Further Reading 
๐Ÿ“š You Must Create The Executive Job You Want

Clarity Step #4: Tell Your Story

Tip #1: Anecdotes are king.
Make your stories punchy, concise, repeatable, passionate, relatable, and engaging. Toss the buzzwords and limit acronyms.

Tip #2: It’s not what you say; it’s how you say it.
Use your BRAINS.

Should I Tell This Story? (BRAINS)

  • Benefits - How can the story be perceived positively?

  • Risk - How can the story be perceived negatively?

  • Alternatives - Is there a better way to tell this story?

  • Intuition - What does my gut say?

  • Now? Never? Later? - Does this story serve the conversation now?

  • Should I write this down first? - Yes.

Further Reading 
๐Ÿ“š What’s Next For You?
๐Ÿ“š So, Tell Me About Yourself...

Opportunity Notes

EARN Opportunity

  • Engage in habit-building, storytelling, content, and process.

  • Assess each opportunity using your CLEAR conclusions.

  • Reflect on your performance regularly.

  • Network by giving to others to build career-defining relationships.

Opportunity Step #1: Design Your LinkedIn (& Brand)

Tip #1 The most value in LinkedIn comes from using it.
LinkedIn does not need to be over-optimized to be effective. Getting too scientific on a largely subjective and ever-changing platform will drive you cuckoo.

Tip #2 Comparison is the thief of joy—and killer of careers.
Don’t fret about comparing yourself to others. Copy and paste isn’t differentiating you (Plus, you’ll be behind anyway).

Opportunity Step #2: Build A Networking Army

Tip #1: Always give more than you take—and surrender the outcome.
We have two ears and one mouth for a reason. Time is our most valuable resource. Reciprocity is a universally accepted social rule. What is the value of undivided attention?

Tip #2: Build a well before you’re thirsty.
Ask for 2 or 3 more people that you can speak with after each networking call. Never put all your eggs in one basket. (For networking or revenue sources).

Opportunity Step #3: Refine Your Job Search Habits

Tip #1: Make opportunity a habit.
What separates the good executives from the great? It’s not money, status, or raw talent—it’s the way they approach their positive habits.

๐Ÿ—ฃ "Goals are good for setting a direction, but systems are best for making progress." James Clear

Tip #2: Make habit easy.
The brain’s instinct to conserve energy makes us lazy! Developing your career must become consistent second nature. You must make it easy.

Active Search Habit Examples

  • Reach 15 people (personal InMails) and engage in 10 posts on social per day.

  • Share one public short tip, video, or article per week.

  • Assess the job market every Thursday only. Set up targeted email notifications.

  • Build a “bookmarks folder” with your search terms across multiple job engines.

  •  Right-click, “open all in new window” to launch your search.

  • Track your applications in a spreadsheet.

  • Build a personal CRM in HubSpot free, set follow-ups.

  • Boilerplate 85% of your Resume. Save multiple versions.

  • Ask for 2-3 new introductions as your call-to-action on each call.

  • Your KPI is # of conversations.

Bonus - Ax The Hidden Executive Killers

  • Silence notifications & trim your tech stack. The average employee is interrupted every three minutes and only productive for two hours and 53 minutes a day.
  • Fight the commute. Employees allowed to work from home just once a month are 24% happier.
  • Reduce sugar intake. Studies show that 80 percent of people who stopped eating sugar and other unhealthy foods found that their mental health greatly improved.
  • Reduce alcohol intake. Studies show that quitting alcohol for good can reverse cognitive damage, including memory, planning, organization, behavior control, and reaction time.
  • Reduce caffeine intake. Studies show that: There are higher reported anxiety levels in moderate and high caffeine consumers compared with abstainers.
  • Prioritize sleep. Executives who are sleep deprived are grumpy and distracted. Someone who sleeps 4 to 5 hours per night performs tasks as if they are legally inebriated.

Opportunity Step #4: Personalize Your Resume

Tip #1 Do it yourself.
The biggest value in your resume is writing it yourself.

Tip #2 Make it personal.
Your resume is designed for an audience of 1. LinkedIn is designed for an audience of many. Know the difference. 

Bonus Section Notes

Bonus: Understand Coaches, Hiring Managers, & Recruiters

Tip #1: Hiring managers have a problem to solve.
Lead conversations with discovery and consultation. “You already have the job mindset.”

!! Advised for execs only. You must thread the needle between aggression/arrogance and confidence/assertiveness.

Tip #2: Recruiters don’t work for you.
Recruiters are selling you a role. They don’t often know or support your best interests.

!! Study the nuances between internal recruiters and outsourced, contingent, and retained executive recruiters.

Tip #3: The right coach is hard to find.
Challenge every claim, data point, and win. Ultimately, you must be confident and committed to your decision to be successful.

Realization Notes

OWN The Outcome

  • Open to exploring and interviewing with more intention.

  • Withstand the barrage of red flags and detrimental opportunities.

  • Negotiate your terms, severance, boundaries, and well-being.

Realization Step #1: Own Your Functional Expertise Interview

Tip #1: Own your story.
If you can’t rely on the interviewer to ask the right questions, who can you rely on? Focus on what you can control, not what you cannot.

Tip #2: Commit to the truth.
Truth matters. Being truthful means that we can grow and mature, learning from our mistakes. Truth creates social bonds, and lying and hypocrisy break them.

Realization Step #2: Drive Assertive Behavioral Interviews

Tip #1: Lead the interview.

Knowing how to navigate the interview is more important than knowing what will be asked. Master interviewers take ownership and interview the interviewer.

!! If you wait to be asked questions, you will always be on the back foot, on the spot, and lose the authority to make your points.

Getting Drilled (Common Interview Questions)

Tell me about a time when:

  • Were a team player.

  • Took ownership.

  • Showed humility.

  • Managed a disagreement.

  • Lead through crisis.

  • Managed conflicting priorities.

  • You accomplished something.

  • Your most challenging project.

  • You showed leadership.

  • You failed or made a mistake.

  • You worked with a difficult person.

  •   You had to persuade someone.

  •  You surpassed people’s expectations.

  •  You had to learn something quickly.

More common questions:

  • What is your greatest strength/weakness?

  • Why should we hire you?

  • Why do you want to work here?

  • What would your coworkers say about you?

  • Why do you want to leave your current role?

  • Can you explain your employment gap?

  • What are your comp expectations? โ›” WARNING DON’T ANSWER โ›” 

  • What do you do outside of work?

  • Where do you see yourself in 5 years?

  • What is your leadership style?

  • Do you have any questions for me?

  •  Further Reading: ๐Ÿ“š 40 More -> Favorite Interview Questions

STAR ICARQ Framework

Describe a time when... GULP!!?

  • Impression - What impression must you make?

  • Context - What is the context of your story?

  • Action - What actions did you take?

  • Result - What was the result of your actions?

  • Question - What question(s) do you have for the hiring manager?

Tip #2: Be assertive.
55% of people (and 79% <35) say they’ve missed work opportunities by not being assertive. 57% of people say they’ve naturally become more assertive with age.

The Benefits Of Being Assertive

  • Gain self-confidence and self-esteem.

  • Gain a sense of empowerment.

  • Understand and recognize your feelings.

  • Earn respect from others.

  • Improve communication.

  • Create win-win situations.

  • Improve your decision-making skills.

  • Create honest relationships.

  • Gain more job satisfaction.

How To Be Assertive

  • Pause before you speak. Express your opinion and speak directly.

  • Say, “Thank you.” Not, “I’m sorry.”

  • Make eye contact with others. Correct your posture.

  • Dress executive appropriate.

  • Take accountability for your mistakes.

  • Get comfortable saying no.

  • Prepare your big conversations and negotiations.

  • Temper your emotions. Practice stoicism.

  • Be open to positive and negative feedback.

  • Practice assertiveness in low-risk situations.

Further Reading 
๐Ÿ“š Interview Preparation: Crush Your Next Interview
๐Ÿ“š Leaders Go First: Why Some Executives Get What They Want (And Others Don't)
๐Ÿ“š Why Didn’t Your Last Role Work Out?
๐Ÿ“š Be More Assertive During Behavioral Interviews
๐Ÿ“š You're Insecure. Why Not Own It?


Realization Step #3: Figure Out Compensation

Tip #1: Study the market compensation trends and benchmarks.
Set the stage for negotiation armed with data.

Getting Comp Data

  • Ask Jacob

  • Ask Your Network

  • Befriend HR, CHRO, CPO

  • Befriend KornFerry & Recruiters

  • Pavilion Comp Benchmark

  • Pavilion Exec Comp Guide

  • Betts Recruiting Comp Guide

  • Levels.fyi

  • Pave.com

  • Salary.com

  • Candor.co

  • DON'T USE: Glassdoor

  • DON'T USE: LinkedIn

Tip #2: Benchmarks aren’t gospel.
Your role is unique. If you’ve navigated the role in your favor or expectations have increased, what others make is largely irrelevant.

Realization Step #4: Deliver Winning Negotiations

Tip #1: You don’t get what you’re worth; you get what you negotiate.
Question: When does a negotiation begin? 
Answer: You're already negotiating.

PS> Bring up severance after you receive a written offer.

Tip #2: Never be so sure of what you want that you wouldn’t take something better.
Oversharing is a killer; concentrate on the information you drip and the timing of when you do it.

Negotiation Tips

  • Use selective word mirroring.

  • EQ is more important than IQ.

  • Leverage calibrated questions.

  • Magnify positive emotions.

  • Fair is the F-Bomb of negotiations.

Empowerment Notes

Support Your TEAMS

  • Teach others to find clarity, create opportunity, and realize their dreams.

  • Embrace each moment, slow down, and care personally.

  • Accept yourself and others with grace.

  • Meditate to retrain healthy habits and move through your actions more mindfully.

  • Support safe environments and inspire diverse teams to collaborate, take risks, and work towards their passions.

Empowerment Step #1: Know Your Greatest Impact

Tip #1: Take a stand.
MAYO Clinic: Being assertive reduces stress and improves communication.

When It's Time To Say Hard Things

  • Did you mean it?

  • Can you defend it?

  • Did you say it with love?

  • If yes to all three—say it and let the chips fall.

๐Ÿ“บ Luvvie Ajayi Jones

Tip #2: Be disciplined and consistent.
If you study those who have achieved great things in any walk of life, you will always find self-discipline in action.

Empowerment Step #2: Shred Anxiety & Imposter Syndrome

Tip #1: Be grateful.
Researchers have found that the brain can't respond to anxiety and gratitude simultaneously — which means it's one or the other.

Tip #2: Embrace a growth mindset.
Train your brain to be more optimistic by adding (YET) to negative statements.

Empowerment Step #3: Establish Your Leadership Style

Tip #1: Share a user manual on how to best work with you.
Gather a 360-degree assessment of your leadership and build a 1 pager for your team.

Tip #2: Be adaptable.
Change is constant and inevitable, and leaders must be flexible to succeed. E.g., some functions or people respond better to autocratic, process-driven leadership. Some require democratic process.

Empowerment Step #4: Always Consider What’s Next For You

Tip #1: You never know what your future self wants.
The Sunk Cost Fallacy is when we continue endeavors we have invested time, effort, or money into it, whether or not the current costs outweigh the benefits.

Tip #2: Give grace; forgive yourself and others.
Use GRACE to transform your leadership, friendships, and community. Grace is a catalyst for positive change to enable the greater good.

Leadership With GRACE

  • Generosity, the will to do something more for others.

  • Respect, the dignity of life and work.

  • Action, the mechanism for change.

  • Compassion, the concern for others.

  • Energy, the spirit that catalyzes us.

Want to speak directly with me about your career? Contact me below.

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