Land your dream job in today’s market: negotiation tactics, job search councils, more | Phyl Terry

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Land your dream job in today’s market: negotiation tactics, job search councils, more | Phyl Terry
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 — Brought to you by: • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers: https://www.sidebar.com/lenny?utm_source=lennys&utm_medium=newsletter&utm_campaign=waitlist&utm_content=1 • Sprig—Build products for people, not data points: https://sprig.com/getstarted?utm_source=lenny&utm_medium=podcast • Dovetail—The customer insights hub for product teams: https://dvtl.link/3Za7aa0 Find the transcript and show notes at: https://www.lennysnewsletter.com/p/land-your-dream-job-phyl-terry Where to find Phyl Terry: • X: https://x.com/phylterry • LinkedIn: https://www.linkedin.com/in/phylterry/ • Website: https://www.phyl.org/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ 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 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.
Land your dream job in today’s market: negotiation tactics, job search councils, more | 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.
  1. 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!
  1. 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.
  1. 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.
  1. 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.
  1. 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.
Aqui estão os principais aprendizados (“key takeaways”) da entrevista com Phyl Terry sobre como conquistar o emprego dos sonhos no mercado atual:

1. Nunca busque emprego sozinho
  • Phyl defende que a busca por trabalho não deve ser solitária. Os grupos chamados “Job Search Councils” (conselhos de busca de emprego) conectam de 6 a 8 pessoas para trocarem apoio, compartilharem ansiedade, celebrarem conquistas e cobrarem resultados. Esse modelo funciona para profissionais de todos os níveis e tem impacto comprovado em tração, motivação e autoconfiança.
2. Candidate-market fit:
  • Assim como “product-market fit”, é essencial definir “candidate-market fit”. Isso significa entender claramente para que tipo de vaga, empresa, estágio e cultura você está realmente apto—baseado não só no seu desejo, mas também nas condições reais do mercado.
  • Ter esse fit “focado e restrito” facilita recomendações e memória das pessoas da sua rede.
  • Exemplo de posicionamento: “Procuro vaga de Diretora de Produto em startup saúde, Series B, em São Francisco”.
3. Ferramentas fundamentais para o processo
  • “Listening tour”: Fazer conversas estruturadas com pessoas que conhecem o mercado e seu trabalho, pedindo feedback sobre seu perfil, objetivos e expectativas.
  • “Mnookin two-pager”: Uma página simples com o que você quer e NÃO quer em um próximo trabalho (isso ajuda muito no autoconhecimento e no alinhamento de expectativas).
4. O poder da comunidade
  • A troca genuína e vulnerável em grupos reduz ansiedade, aumenta accountability e expande a rede de apoio, inclusive emocional.
  • Não é só networking: é construir confiança, praticar abertura e aprender a pedir ajuda.
5. Táticas de negociação e diferenciação
  • Nas entrevistas, crie sua própria versão da missão do cargo e OKRs (objetivos e resultados-chave) — até antes de receber uma proposta. Compartilhe esse rascunho com o gestor para surpreender positivamente, mostrar preparo diferenciado, alinhar expectativas e até descobrir pontos críticos do cargo (ex: orçamentos, dívida técnica, recursos).
  • Negocie não apenas salário, mas também condições para seu sucesso (ex: verba para eliminar dívida técnica, treinamentos, equipe).
  • A postura não é antagonista, mas colaborativa: “do que precisamos para garantir os resultados que combinamos?”.
  • Peça por aumento de salário de forma aberta, mas sem hostilidade. Exemplo: “Você está aberto a discutir X?”
6. O valor de pedir ajuda — do jeito certo
  • Pedir ajuda é um sinal de força, não de fraqueza.
  • Faça dever de casa antes, seja concreto e respeitoso, e peça conselhos (“O que faria no meu lugar?” em vez de “Consegue um emprego para mim?”).
  • A comunidade serve também para apoiar nesse momento de vulnerabilidade e reforçar autoconfiança.
7. Atualize e comunique sempre
  • Mantenha sua rede informada dos seus avanços, mesmo sem grandes novidades.
  • Isso mantém sua busca viva na memória das pessoas e abre portas para novas oportunidades.
8. Estratégias extras
  • Se necessário, aceite uma estratégia em dois passos (ex: assumir uma posição de IC para aprender e depois buscar liderança).
  • Mantenha-se próximo da fronteira tecnológica: quem fica afastado por muito tempo perde oportunidades, especialmente em crise.
9. Indicadores de sucesso do processo dos Job Search Councils
  • O tempo médio de recolocação nos conselhos é três meses—abaixo da média nacional.
  • O benefício emocional é tão importante quanto os resultados práticos.

Resumo final:
  • Não busque emprego sozinho—apoie-se em comunidades estruturadas.
  • Defina seu “candidate-market fit” de forma clara e específica.
  • Use OKRs e missão do cargo para se diferenciar na seleção e negociação.
  • Aprenda e pratique a pedir ajuda.
  • Atualize sua rede e permaneça aberto a feedbacks e iterações.
 
  1. https://www.youtube.com/watch?v=OH3nzRdwYPA