What determines whether a hiring search for a role succeeds?

Brad Gerstner · Oct 10, 2022

The biggest hiring mistakes in investment firms are structural rather than about individual people — you must be clear on your strategy and build an organization that reflects it

There are many ways to make and lose money in this business, so the North Star and strategy have to define the org design

48:05 20VC: Altimeter's Brad Gerstner on Why Supercycles and the Powerlaw is the Most Important Thing In Investing, Why Portfolio Diversification is the Opposite of Risk Mitigation and The #1 Question Brad Asks All New Recruits

Jean-Denis Greze · Jul 21, 2023

The biggest hiring mistakes are not being crisp upfront about what the role actually requires and not having the interview panel aligned on what they are looking for, especially for senior hires

If you can't answer yes to those questions, you're into the firing conversation — so you need the objective data point early

12:42 20VC: Why Hiring in Tech is Broken and Founders Need to be as Good at Firing as they are Hiring, Why Product Differentiation is Unsustainable & Why the Current Generation of Tech Employees are Entitled and What Needs to Change with Jean-Denis Greze @ Plai

Kevin Niparko · Sep 29, 2023

The two big mistakes in hiring product people are not having a crystal-clear understanding of which product archetype the role requires, and not staying deliberate and committed to hiring for those specific spikes

Product people spike differently — strategy, culture/team building, go-to-market partnership, execution — so without clarity on the archetype you can't test for or hold the bar on the right qualities

14:40 20Product: Why Product Memes Are More Important Than a Product Roadmap, Why Writing is the Essential Skill for Product People, How AI Changes The Role of Product, Big Mistakes Founders Make When Hiring Product Teams with Kevin Niparko, VP Product @ Twilio

Kevin Niparko · Sep 29, 2023

The hiring process really starts well before the first candidate meeting — the internal debate that defines the role and spec is upfront work that pays dividends throughout the process

Defining not just the role qualities but also the complementary qualities the departing person brought to the team gives the hiring manager clarity on what to test for

15:50 20Product: Why Product Memes Are More Important Than a Product Roadmap, Why Writing is the Essential Skill for Product People, How AI Changes The Role of Product, Big Mistakes Founders Make When Hiring Product Teams with Kevin Niparko, VP Product @ Twilio

Eléonore Crespo · May 9, 2025

Most hiring mistakes come from not defining what 'great' means for the specific role at your specific company and stage

A great CRO for HubSpot or for Figma is not the great CRO for Pigment today — companies differ in being product-led versus sales-led, so people screen for smartness and culture fit instead of role-specific criteria

Scope: role and stage specific

22:31 20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment

Harry Stebbings · May 9, 2025

Most founders don't know what they're looking for in a role, and many are hiring for roles where they have no idea what great looks like

A sales-led founder typically has no benchmark for what a great CTO looks like

23:09 20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment

Anton Osika · Aug 18, 2025

Founders should stay in the details of hiring rather than delegating it, and should proactively test whether a candidate is intrinsically motivated by the company's outcomes

His own hiring mistakes came from delegating too much and not probing candidates' inherent motivation

Scope: framed as lessons from his own hiring mistakes

51:26 20VC: Lovable CEO Anton Osika on $120M in ARR in 7 Months | The Honest Truth About Defensibility and Unit Economics for AI Startups | The State of Foundation Models: Long Grok, Short OpenAI, Why | Replit vs Lovable vs Bolt: What Happens

Jason James · Aug 29, 2025

The most common hiring failure is hiring managers over-delegating to recruiters while having muddy thinking about what they actually want

If the manager doesn't know what they want, the recruiter can't know either, so the search fails; the best hires come from hands-on, actively involved hiring managers

17:41 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi

Elias Torres · Mar 21, 2025

Founders who keep making bad hires fail because ego stops them from changing their hiring process — doing more research, testing, or real reference checks.

The people making those decisions don't change their process; ego prevents them from admitting the process is broken or being more upfront with candidates.

35:28 20VC: Selling Drift for $1.2BN is the Biggest Failure: What No One Tells You About Selling Your Company | Why Incumbents Are Slower & Worse Than Ever | Why the Most Valuable Companies in a World of AI Will Not Have More Than 100 People with Elias Torres

Elias Torres · Mar 21, 2025

Mishires are the founder's own failure, not a failure of information — the warning signs were visible and desperation caused him to override them.

He saw the problems but needed help to build things and convinced himself it would be okay.

37:12 20VC: Selling Drift for $1.2BN is the Biggest Failure: What No One Tells You About Selling Your Company | Why Incumbents Are Slower & Worse Than Ever | Why the Most Valuable Companies in a World of AI Will Not Have More Than 100 People with Elias Torres

Jason James · Aug 29, 2025

The way to figure out what you want in a hire is to start from the outcomes that would count as success at 30/60/90 days plus non-negotiable culture traits, then talk to twenty or thirty candidates to build pattern matching

You can't tell an excellent answer from a weak one up front; you only learn the difference by talking to many people, and by asking others who have hired for the role what to look for

18:46 Define 30 60 90 day outcomes and pattern match across many candidates

Harry Stebbings · Aug 17, 2022

Founders hire mediocre sales leaders because they have no reference point for what truly great looks like, and the canonical advice to interview ten of the best in the world doesn't work in practice

The genuinely best sales leaders won't take calls with unknown founders just to help them hire someone a fraction as good, so founders never get the calibration

48:56 Founders lack reference points so hire mediocre leaders and interview ten best advice fails

Eléonore Crespo · May 9, 2025

To hire well for a role outside your expertise, build a rubric by asking 20–50 of the best practitioners in that role in your category what makes them different and what to ask

You need other people who have done the job to tell you what to look for and what questions to ask; AI tools can refine the profile but human-to-human research is the primary source

23:26 Build a hiring rubric by interviewing dozens of best practitioners in the role

Mike Duboe · Feb 15, 2023

The two biggest mistakes founders make hiring growth teams are not referencing deeply enough to understand what 'growth' meant at the candidate's prior company, and structuring the org as if growth is solely the growth team's job

A head of marketing hired to run a product function is a mismatch, and someone made solely responsible for growth in an org that doesn't share it is destined to fail

46:23 Growth hiring mistakes stem from shallow referencing on what growth meant previously and from making growth solely the growth teams job

Kieran Flanagan · Aug 10, 2022

The biggest mistake founders make when hiring growth teams is failing to set them up for success — wrong structure, poor alignment with the business and other teams, and no executive sponsor

48:22 Poor structure alignment and missing executive sponsor cause growth hiring failure

Davis Smith · Dec 15, 2023

Running an executive search yourself beats using a search firm when you know what the brand needs, because an expensive firm process pressures you into picking from their shortlist

The blind profiles they offered included people he already knew and would not choose, and with an investor pressing on results he would have felt forced to hire from the final two or three

41:19 Self run search beats a paid search firm when you already know the target profile