Never Search Alone: Why a Job Search Council Beats Going It Solo

A Job Search Council is a support group of six to eight job seekers who commit to going through the search together. Terry lays out a methodology for working out your candidate market fit and for playing to win rather than playing not to lose. The product community, he says, is where the format came from and where it is most at home, though it is not only for product people.

The reason it works, according to Terry, is baked into human psychology: when anxious people are asked to be open, vulnerable and willing to ask for help, the anxiety flips into hope, confidence and accountability. He stresses that everyone he works with, including CEOs and chief product officers, feels insecure during a search. Going alone only magnifies that feeling.

He traces the idea to his mother, an elementary school teacher who formed a council of teachers in 1960 that met for 50 years, until the year she died. After his father left in the 1970s she lost her tenure and had to restart as an entry-level teacher in Los Angeles, and her council held her hand through it. Terry says that is why he rejects the idea that the method only works in good markets: it was born in bad ones, and he saw the same pattern after the dot-com crash while running Creative Good.

Terry says more than 2,000 councils have been launched, all free and volunteer-driven, with 20,000 hours of volunteer work already invested. Book sales and his own money cover technology and support costs. Job seekers apply on his site, are matched behind the scenes, and are separated into fast seekers who are out of work and slow seekers who are still employed.

Each council needs a moderator, who is simply a job seeker volunteering to run the group, and moderators get matched faster and receive extra training. After a live orientation, members get a free 100-page workbook and hold a first "meeting zero" where people share their stories and build trust. Fast-seeker councils then meet twice a week and slow-seeker councils every two weeks.

The most important thing to manage in a search, Terry argues, is not the resume or LinkedIn profile but your emotional balance sheet, since many job seekers carry more liabilities than assets in the form of fear and demoralisation. He shares testimonials from members, including a chief product officer who liked applying the product process to his career. He also admits he has no magic wand in a down market, and that the search can be hard and even humiliating.

He frames the whole effort as a private safety net for people hit by creative destruction, the dynamism that has grown the economy but leaves workers anxious. Governments handle unemployment insurance, he says, but will never innovate on how to actually look for a job. He adds that loneliness is a documented health problem, and that councils offer real community rather than message boards.

Candidate market fit, Terry says, is the most important tactic in the book after the council itself. A job search takes place in a marketplace with supply and demand, and with tech layoffs the supply is high. A director who could have landed a VP role two years ago may now compete with VPs willing to take director roles, and he says it is a relief for people to learn this is the market, not a verdict on them.

The first step is to write down what you want and what you do not want, a document he calls the Mnookin two-pager after a Harvard Business School professor who helped create it. Most people instead spray and pray, but Terry says he slows them down so they can go fast, and notes that the average search inside a council is three months against a national range of three to six. Sharing the drafts in the council helps members spot things they forgot to add to their own.

Next comes a listening tour, because in a job search you are the product and have to find out what the market wants. He asks people to pose the golden question: "If you were in my shoes, how would you approach this?" He describes three structured conversations: reverse exit interviews with former colleagues, your broader network, and recruiters, who dislike being barraged with requests for a job but welcome questions about what you are a fit for.

The tour has a hidden benefit: people who are asked for advice in a thoughtful way become invested in your success and act as listening posts who will tell you about roles. Terry also urges employed people to take recruiter calls, build those relationships early and help recruiters out. His community is trying to build a volunteer recruiter network to give job seekers feedback on their fit.

After 10 or 15 listening conversations, you should write a focused candidate market fit statement, and this is where Terry says you most need your council, because every instinct pushes you to keep it broad. He compares it to product teams who want to build for everyone and learn that it does not work. His example is a director of product role at a Series B healthcare startup in San Francisco.

A narrow statement is counterintuitively expansive. If a friend knows you want a director of product role at a Series B health startup, they may think of a similar fintech company in a regulated industry, but if you say you will take any product job, no one will ever think of you. Terry sums up the idea with "a spear and not a net," noting that with a net everything slips through.

He says a good statement has three or four attributes, such as stage, industry, level and function, and culture, and should fit in a single sentence. One product designer positioned herself as looking for companies with no design team or that needed to reboot one, which is an image people remember. Once the council signs off, you thank your listening-tour contacts, share the statement, and post it on LinkedIn, then revise it as the market shifts.

On picking a company stage, Terry says to lean on your council, network and experience, though he notes that right now new product jobs are being created more at startups, while large tech companies have been shedding people. He is careful not to tell anyone to join a startup they would hate. He also warns that taking any job just to cover the bills while still searching is harder than people realise, and that the council matters even more then.

He tells of a coaching client, an EVP running streaming at a traditional media company, who aimed for Netflix or Apple TV. The market said his candidate market fit with a top streamer was as an individual contributor, and he took that path and has done very well. Another example was a startup chief product officer who realised she was not learning and moved to an IC role in a larger tech company before things got worse.

Sometimes the answer is a two-step strategy. A VP of product wanted a COO role the market said he did not fit; he interviewed with 50 companies over a year and a half, and the one that hired him went bankrupt ten days later amid fraud. He went back to a VP of product role and eventually pursued COO from inside a company instead. Terry says that none of this is about innate worth, but about staying close to the technology frontier so you do not get stuck, particularly for people dealing with ageism in their 50s and 60s.

When Lenny asks how to get comfortable with possibly returning to an IC role, Terry answers that being in a council and Slack community shows you it is not you, it is the market. He also tells job seekers to send every contact a monthly update note, even if the news is just that they are still looking, and notes that his chief product officer example admitted he had not done this enough.

Terry met a group of about 50 job seekers who had been in the community for over a year and were struggling. They had stopped networking, left their councils and failed to update their candidate market fit. His point is that the process only works if you do all of it, and that asking for help makes you more independent and accountable, which is what he means by "the I in village."

He compares today with the dot-com bust of 2000 to 2002, when the industry was much smaller and people had only been in web jobs for a couple of years. Now many tech workers have spent a decade or more in jobs without ever seeing a downturn, and the market will improve at some point but is tough now. What he can offer, he says, are tools, community, heart and smarts.

On candidate market fit, he adds that you should expect to resist the narrowness and that this resistance is normal. Examples include a Nike VP of product who first rejected the idea until VCs told him they needed something specific, and a chief data officer named Dee who spent a year alone getting nowhere. Once she found her fit as a CTO at a mid-size regional bank, she had three offers in three weeks, though Terry cautions that senior searches can take six months or a year.

Terry says half of the people who read his book and follow the rest of the advice skip the step he considers the biggest miss. When interviewing, privately draft your own version of the job description as a job mission with objectives and key results, covering what you think you will be accountable for and the outcomes you will deliver. He is clear this is not about being a ruthless negotiator, but about taking charge and playing to win.

Drafting it helps you ask sharper clarifying questions, and after a couple of interviews you share the draft with the hiring manager, by call, video or coffee rather than email. Terry quotes a senior Amazon leader who has hired over 2,000 product leaders: no one has ever done this, it would blow his mind, and he would hire them on the spot. He says this step has often been the difference between a silver medal and gold, since the silver in a job search is worse than at the Olympics.

The conversation also helps you avoid the common trap of taking job A that turns out to be job B. A hiring manager may tell you an OKR is not part of the role, or point to one you have missed. The draft also shows initiative and accountability, which addresses the hiring manager's core problem of telling a good talker from someone who makes things happen.

Once you have an offer, Terry says, link your asks to the OKRs you already agreed on with the hiring manager. In his example, two chief product officers at similar private-equity-owned SaaS companies faced tech debt of $20 million and $10 million. The one who explicitly asked for budget in the negotiation got a check on day one, the debt was relieved in six months, and he was later promoted to a GM role and interviewed for CEO roles, while the shy one never addressed it and was job hunting again.

The same logic applies at any level: a senior hire might negotiate a training budget for a team they do not yet run, and a junior hire can ask about mentorship or conferences. Terry says companies love this, and that a company that does not like it is showing a huge red flag. He frames it as a collaborative conversation about how you will be set up for success, and if they say no you at least walk in with eyes open.

Only after that does he suggest asking about money. He cites a longitudinal statistic that 87% of the time people who ask for more get it, while adding that room is tighter in this market. He recommends a non-aggressive ask such as whether they are open to a higher figure, and says he does not want people to be sharks about it.

Lenny admits he hates negotiating, and Terry agrees, saying companies have lawyers and HR while the candidate is alone, which is exactly when you need your council. He strongly prefers doing it live, in person or by phone, with the hiring manager when the company allows it, since a hiring manager often will go to bat for you behind the scenes.

Before the listening tour, Terry asks people to do a gratitude house exercise: list everyone who helped you get where you are, even a third-grade teacher. It surfaces people to talk to, and just as importantly it corrects the belief that you are alone. Before an interview he asks people to remember all those people and walk in as though they were on their shoulders.

After every interview or negotiation, he says to debrief with someone, because we all misread what happened. He tells of a director of product who texted that she had botched an interview even though the company wanted to move her to the next round. That, he says, was her inner critic, and another exercise in the book is to name your critic; his is called Tub Tour, a nickname from his father. Lenny adds that a podcast guest, Joe Hudson, makes the point that your inner critic is always lying to you.

If anxiety erodes your confidence, he warns, you will show up badly, slide further down the market, and may start to feel worthless. He tells anyone who has been out of work for a while that they are not worthless and are worth the investment. Terry says he sees a therapeutic aspect to councils, though he would never call it therapy.

Terry says he learned to ask for help from his mother, whose nickname was Chic. As a teenager in a very difficult situation, he asked his high school teachers for help and was in his words carried by them, along with the family of his high school girlfriend. He admits he believed it was a weakness and that people would think less of him, but says that is not what happens.

Asking badly does have costs: not doing your homework, or asking someone to do the work for you. He recalls getting emails from strangers asking to be introduced to Marissa Mayer at Google, which he never answered; had they asked for advice on growing their business, he would have taken the call. He offers four counterintuitive rules, including that asking signals confidence and is a giving activity, not a taking one.

To make the point, he describes Mayer asking his product council for feedback on a new product before presenting it to the board, which left people delighted to help. His thought experiment is to imagine a person you respect asking for your expertise in this way, and noting how honoured you feel. He also tells of Intuit's Brad Smith, who lost $300 million on a project because he did not ask for help, and later joined a council and saw the stock rise sevenfold during his tenure as CEO.

Terry points to Kenneth Chenault at American Express and Warren Buffett as leaders who asked for help, and shares data from his book: 85% of people in senior roles credit asking for help, while 85% of junior people say they fear it is a sign of weakness. Without learning to ask, he says, a junior person will likely remain one.

Examples of asking for help range from Chenault's habit of asking people how they see things, which he called defining reality, to having someone review an important email. Terry also teaches a workshop on using ChatGPT with communication models for this. He describes peer coaching calls such as one in which a new president of a digital retailer asked three other retail presidents who had re-platformed what they would do in her position.

For a new job he suggests a first 90 days peer coaching call with people in the same role, sharing your job mission with OKRs and asking what mistakes to avoid. For someone wanting a promotion, he suggests a career evolution call with people who hold the next-level role. These are practices from his paid product councils, he says, but you can do them on your own.

Terry tells the story of Bradley Horowitz, who joined Google in 2008 and felt intimidated in a weekly meeting with senior leaders. He sensed that Sundar Pichai was approachable, asked whether the meeting felt intense to him too, and then built enough trust to ask a more pointed question about Sundar's remit. Terry's lesson is that Horowitz was open and vulnerable but thoughtful about whom he asked, and Terry says it helped lead him to a VP of Product role.

On technique, he says to consider the relationship, since a stranger cannot expect what a close friend can, and to listen to your own emotions: if you do not trust someone, do not get vulnerable with them. Practise in the safe format of a council, and never disguise a favour as a favour to the other person. Say instead, "I have a favor to ask, would you be willing?", because most people will say yes to that.

Terry leaves listeners with the point that everyone feels anxious and insecure in a job search because the system that gives capitalism its dynamism also creates instability. He compares his book to a cookbook: you do not get the calories from reading it, you have to make the dishes, meaning you need an actual council to experience that you are not alone. Lenny adds that he originally called his own newsletter project Avoid Getting a Real Job.

He describes his paid work, product councils he began about 21 years ago for VPs and chief product officers, which Marty Cagan has supported from day one, along with an associate council program for ICs and new managers. He also runs reading and learning communities, including the Reading Odyssey and a high school business-literacy program, and Slow Art Day, which has been held in 1,500 museums. Terry says he calls himself a reader, because books are "machines to think with," and that he treats Warren Buffett and Steve Jobs as distant mentors he studies closely.

In the lightning round he recommends *Creative Destruction*, which argues that more jobs get created than lost, and says AI will create more jobs rather than destroy them for people close to the frontier. He also recommends Marty Cagan's books, which he says to read and reread, and *The Manual*, a short introduction to Stoicism. His favourite interview question for senior roles is to ask about a time the company brought in a senior person and it failed, and why.

For reference checks he leaves a voicemail saying he is about to hire the candidate, and asking them to call back only if it would be a huge mistake not to. His final advice is simple: go to his website and sign up for a free Job Search Council. He is raising $100,000 to build a free platform for job seekers, is looking for volunteers, and asks listeners to tell anyone they know who is looking for work.