Lenny’s podcast today, The playbook for building high talent density teams, is with Adam Ward, Head of Talent at Cursor. He describes the current market as a tale of two cities, and the phrase has been sitting with me all day, so I decided to post this topic for today.
The market has a matching problem, not simply a shortage of jobs, nor a shortage of talent.
One side: Companies that cannot find people. Mostly senior talent, and the specific kind of people who can do the specific thing they need. Searches and interview loops running months with no offers. We have seen many jobs open on the market. And many open for months. Some of them are real openings and do demonstrate the challenge of hiring.
On the other side: My LinkedIn feed, full of people looking. These are senior people in and adjacent to my network. These are not entry-level people; these are people who are experts, who have run teams. Some of them have been on the job market for months. Some people I know of took a year to find the right fit.
Both sides are our realities these days. This is not a shortage of talent, and it is not a shortage of jobs. It is two sides failing to find each other.
Ward has a name for the machinery that keeps them apart. He calls the traditional recruiting funnel the “funnel of doom.” His argument is that a process designed to filter for volume is poorly suited to finding exceptional talent. His alternative is to treat every hire like an executive search. Scope the role precisely. Map who in the world can actually do it. Then pursue those people relentlessly.
This approach aligns with my personal experience as well as how I have been pushing the hiring process. He says
“The more that we can care for our candidates and demonstrate that, is our unfair advantage.”
That is coming from Cursor. A company that could presumably win almost any bidding war it entered. Its head of talent says the advantage is caring. I realized I had just experienced exactly what he was describing.
I started a new role a few weeks ago. Almost none of how it happened looked like a funnel.
It started with a conversation. My manager made time for it before there was a role in front of me. Only in a casual exchange did he mention, by the way, we are hiring. We talked more than once, not about hiring, not about the role, but about our practice and philosophy of running a design team. He was curious about how I think about operations, and I learned about how he runs a team. None of it felt like a screen, more like an exchange of ideas. By the time I put my name in, I was already excited about the possibility of working with him and his team.
Then the process itself moved. They removed steps that would not have told them anything new about me. They added steps that would. The shape of the interview followed the person, me, instead of a template, and I learned what they cared about by watching what they chose to ask.
That is the caring Ward is describing, made concrete. It cost a manager’s time. But it also saved time in the end. The process was targeted rather than high-volume. By the time I entered the pool, the vetting was targeted, the offer was swift, and the negotiation was simple.
I know this is a lucky version of the story. Most searches do not go this way. But the pieces that made it work are reproducible, which is why they are worth sharing.
Define the match before you start searching. Ward calls this scoping, and I would go further: most job descriptions I read describe a category of person rather than the work waiting to be done after they onboard. If you and your hiring panels cannot say what the first six months solve, you all interview against a feeling: none of the candidates feels right; or you end up hiring whoever performs best in the interview process. You end up hiring interview skills rather than job skills.
Cultivate people relationships. Build relationships before you hire. Build that network long before you need it. This is mapping and pursuit, done at human scale. The best hires I made came from relationships that were already years old when the role opened. None of that was luck. Keep talking to people whose work you respect during the stretches when you have nothing to offer them. Strategically, make time to attend community networking events, and make time to talk to people who reached out on social networks. [More on this topic here: Search your network. Don’t hand it the decision. ]
Know your tradeoffs. You don’t need to be the highest bidder, but you have to be the right offer for the right person.
This is the one people underestimate, and it is what caring matters. If you cannot match Cursor or Google on cash, say so early and say what you have instead. People work for pay, but that is not the only incentive. Some other areas I typically consider are:
Mission. What are you trying to change?
Scope. What will this person actually own?
Impact. Who will their work affect?
Growth. What will this role allow them to become?
Candidates can make better decisions when managers are honest about their tradeoffs. Not every candidate will, but many people will take the job that is the best match over the highest base salary. If you can offer both, that would be great,
Know what you’re matching for. Don’t just search the job title you want. Job title means very different things across different companies. Know why you want it. Industry, company size, scope, manager, problem space, stage of company. The reason matters because it changes how you search, how you present yourself, and which conversations you pursue. Which offer you take.
Show depth of your craft but be curious and open. Simple. You need to be good at what you do at the level you are at. Identify your strength first. But that is the baseline. The people I want on a team are not just deep in something specific; they are genuinely interested in what is outside their comfort zone, curious about new capabilities. Especially now. With AI, many approaches and workflows are new, or not yet invented. Keep learning new skills, and even when you are searching for a job, continue developing those skills in your potential strength area.
Interview the company for fit. Ask who held the role before you and where that person went if this is a backfill. Ask what the manager is worried about. Ask what the team argues about. Interview is a two-way street.
AI is making both sides of the funnel more efficient. Candidates can apply to more jobs, tailor resumes to keywords, and generate polished, highly targeted applications and even portfolios. Companies can process more candidates and filter applications faster.
Everyone becomes more efficient at doing the wrong thing. This efficiency doesn’t solve the matching problem. If anything, more volume is just more noise, making the signal harder to find.
For companies, there is a person for whom what you have is the right offer. Your job is to find that person and tell them the truth. It is slower than a bidding war, but it holds up better. The best hire isn’t necessarily the person who performs best in a lengthy funnel. It’s the person whose strengths match the problem the company actually needs solved.
For candidates, being excellent at the craft gets you into consideration. Being the right match determines whether the relationship works. There is a job that is the best fit for your natural strengths and will challenge you to develop your potential strengths. The best offer isn’t the one that wins the compensation war. It’s the one where what you want and what the company needs overlap.
Hiring isn’t about finding the best person. It’s about finding the right match.
It’s a match.
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Additional readings/ listening
The playbook for building high talent density teams — Lenny’s Newsletter
Cursor’s Hiring Secret: Treat Every Role Like an Executive Search — Surface
A Founder’s Guide to Executive Hiring with Adam Ward — Sierra Ventures ASCEND
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