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Phyl Terry is the author of Never Search Alone, which I’ve seen so many people reference as the most impactful guide they read for finding a job. Phyl was on the founding team of the first company Amazon acquired back in the ’90s and then was CEO of pioneering product consulting firm Creative Good, with companies like Apple, Facebook, and Microsoft as customers. Today, Phyl is the founder and CEO of Collaborative Gain, which 20 years ago pioneered bringing councils to senior product leaders and GMs in Silicon Valley. That’s their day job—in addition to that, Phyl runs a free global community for job seekers based on their latest book. In our conversation, we discuss:

• Why you should never search for a job alone

• How job search councils work

• How to determine your “candidate-market fit”

• How to conduct a listening tour

• Creating your job mission and OKRs

• How to negotiate job offers

• The art of asking for help

• Tactics for effective networking and interviewing

• Much more

Find the transcript at: https://www.lennysnewsletter.com/p/land-your-dream-job-phyl-terry

Some takeaways:

1. If you’re job hunting, consider joining a job council—a support group of six to eight people also seeking employment. These councils, organized by Phyl, provide a space where members can share experiences, offer encouragement, and hold each other accountable throughout the job process. By joining, you’ll replace fear with hope, motivation, and a stronger sense of purpose.

2. Just as product people seek product-market fit, you should aim for candidate-market fit in your job search. Instead of applying everywhere, focus on roles that align with your strengths and the current job market. You can’t be everything to everyone—understand the market, identify your unique value, and target opportunities where you can excel. In job hunting, you need a spear, not a net!

3. A key step in finding your candidate-market fit is conducting listening tours to understand what the market really wants. There are three types of tours to consider:

   1. Reverse exit interviews: Reach out to former colleagues and ask: “What are my strengths?,” “What roles do you think I’m suited for?,” and “Does my self-assessment align with your perception?”

   2. Broader network: Pose the golden question to your network: “If you were in my shoes, what would you do?”

   3. Recruiters: Instead of simply asking recruiters for jobs, inquire: “What roles do you think I’m a fit for?” Build relationships by seeking their advice.

4. Create your own “job mission” using OKRs to counter the fact that many job descriptions don’t clearly define what the company or role is trying to achieve. You’ll gain several unexpected advantages. First, this process helps you develop insightful interview questions. Second, after a couple of interviews, you can share your draft with the hiring manager, showing initiative and a focus on outcomes. Finally, if your OKRs include tasks that aren’t part of the job, you’ll learn this early—before accepting the role—and you can make a better-informed decision.

5. Once you’ve received an offer, you’ll enter the negotiation phase, where many hesitate to ask for what they truly want. Before discussing salary, talk to the hiring manager about key priorities, such as addressing potential tech debt or other critical areas. Ensure that the company is committed to setting you up for success, whether through training your future team, mentorship, or professional development. While this conversation may seem bold, it shows you understand the role’s requirements. If the company is not receptive, consider it a red flag. Approach the negotiation collaboratively, using phrases like “Here’s how I see it” and “Does this make sense to you?” This fosters a collaborative conversation focused on ensuring your upcoming success from day one with the company.

6. Before going into any negotiation or job interview, do a “gratitude house” exercise. List all the people who have helped you throughout your career, from mentors to family members. Reflect on this list before your interview to remind yourself of the support you carry with you. This exercise can boost your confidence and help you feel less alone in the process.

Where to find Phyl Terry:

• X: https://x.com/phylterry

• LinkedIn: https://www.linkedin.com/in/phylterry/

• Website: https://www.phyl.org/

In this episode, we cover:

(00:00) Phyl’s background

(01:58) The concept of job search councils

(04:27) The power of community in job searching

(08:55) The scale and structure of job search councils

(12:27) The impact of job search councils

(20:19) The concept of candidate-market fit

(22:50) Writing a Mnookin two-pager

(24:37) Conducting listening tours

(30:12) Creating a focused candidate-market fit

(36:20) Advice on finding the right stage of company for you 

(40:37) Identifying your unique path

(45:30) Navigating tough job markets

(49:07) Playing to win

(53:36) Negotiation tactics for job offers

(01:05:12) The gratitude house exercise 

(01:10:48) The power of asking for help

(01:19:18) How to ask for help

(01:28:40) Final thoughts and advice

(01:38:21) Lightning round

Referenced:

• Never Search Alone: The Job Seeker’s Playbook: https://www.amazon.com/Never-Search-Alone-Seekers-Playbook/dp/B0BJ486SJ1

• Join a job search council: https://www.phyl.org/join-jsc

• Justin Meats on LinkedIn: https://www.linkedin.com/in/justinmeats/

• Teresa Torres on how to interview customers, automating continuous discovery, the opportunity solution tree framework, making the case for user research, common interviewing mistakes, and much more: https://www.lennysnewsletter.com/p/teresa-torres-on-how-to-interview

• Allison Mnookin on LinkedIn: https://www.linkedin.com/in/allisonmnookin/

• What is SOC 2 compliance?: https://www.vanta.com/collection/soc-2/what-is-soc-2

• Marty Cagan on LinkedIn: https://www.linkedin.com/in/cagan/

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty

• Candidate Market Fit with Michael Newton: https://www.linkedin.com/events/powerofjobsearchcouncils-candid7176988900580585472/

• Jason Fried on LinkedIn: https://www.linkedin.com/in/jason-fried/

• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking

• The Artist’s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252

• How embracing emotions will accelerate your career | Joe Hudson (executive coach, Art of Accomplishment): https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson

• On asking for help (even when you really don’t want to): https://www.lennysnewsletter.com/p/on-asking-for-help-even-when-you

• Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/

• Brad Smith on LinkedIn: https://www.linkedin.com/in/brad-d-smith/

• Ken Chenault on X: https://x.com/chenaultken

• Warren Buffett on X: https://x.com/warrenbuffett

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack

• Bradley Horowitz on LinkedIn: https://www.linkedin.com/in/bradleyhorowitz/

• Jonathan Rosenberg on X: https://x.com/jjrosenberg

• Susan Wojcicki: https://www.forbes.com/profile/susan-wojcicki/

• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/

• Reading Odyssey: http://www.readingodyssey.org/

• The World of Business Reading Group: https://collaborativegain.com/warren-buffet-reading-group/

• Slow Art Day: https://www.slowartday.com/

• The Power of Creative Destruction: Economic Upheaval and the Wealth of Nations: https://www.amazon.com/Power-Creative-Destruction-Economic-Upheaval/dp/067429209X

• Moody’s: https://www.moodys.com/

• Marty Cagan’s books: https://www.amazon.com/stores/Marty-Cagan/author/B00J21JTNM

• The Manual: A Philosopher’s Guide to Life: https://www.amazon.com/Manual-Philosophers-Guide-Life/dp/1545461112

• Women in Blue on Apple TV+: https://tv.apple.com/us/show/las-azules/umc.cmc.73wmdmkfpta5ul1vbwckmme39

• Ted Lasso on Apple TV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy

• Inside Out 2: https://movies.disney.com/inside-out-2

• The Landmark Herodotus: The Histories: https://www.amazon.com/Landmark-Herodotus-Histories-Robert-Strassler/dp/1400031141

• The Landmark series: https://thelandmarkancienthistories.com/

• Calendly: https://calendly.com/

• Resources for Lenny’s Podcast on Phyl’s site: https://www.phyl.org/lenny

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.