Mar 6, 2025 · 59m · in-depth
What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
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Eeke de Milliano, Global Head of Product at Stripe, explores why executive searches suffer from a 50 percent failure rate and shares actionable frameworks for candidate evaluation, cultural alignment, and onboarding. She argues that executive hiring success hinges on upfront founder introspection, assessing counterfactual impact, and fostering strong executive team alignment.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Brett holds 21.9% of the talking time here. How this is scored →
Brett as informed peer 4.4 Guest teaching 5.3 Guest disagreement 1.2 Brett pushing back 1.5
speaking balance: gold is Brett, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 42:05 Mercenary leadership skepticism
Eeke candidly critiques executives with repeated short stints as mercenaries lacking resilience to endure difficult cycles.
Hardest push from Brett ▶ 11:14 Pushback on universal executive excellenceBrett asks if globally excellent C-suite executives exist across standard tech companies, leading Eeke to challenge the premise with value-alignment realities.
Biggest teaching moment ▶ 35:10 The incentive trap of executive strategy changesEeke masterfully explains the perverse structural incentives new leaders face to manufacture reorgs and strategy changes to buy time.
Brett holds their own ▶ 25:15 Probing candidate counterfactual contributionBrett and Eeke dissect how interviewers must specifically isolate candidate impact from company-wide tailwinds.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Brett as informed peer | Guest teaching | Guest disagreement | Brett pushing back | Why |
|---|---|---|---|---|---|---|
| The Persistence of Executive Hiring Failures and Shared Industry Frustrations | 4 | 5 | 1 | 2 | Brett asks Eeke about her recent exploration into why executive hiring fails. Eeke explains that despite spending huge amounts of time and high stakes, executive searches still fail fifty percent of the time. | |
| The Importance of Upfront Introspection and Future Fit | 4 | 6 | 2 | 1 | Eeke reframes executive hiring by explaining that 80% of the work is upfront introspection rather than onboarding or interviewing, referencing Mike Maples's Pattern Breakers concept of authentic founder-market fit. | |
| The High Stakes and Contextual Nature of Leadership Hiring | 5 | 5 | 2 | 2 | Brett probes whether globally excellent executives exist across similar companies, but Eeke pushes back slightly, arguing that leadership excellence is heavily context and value-dependent. | |
| Defining Company Operating Principles and Managing Cultural Change | 5 | 5 | 1 | 2 | Brett notes how discussions of values can make eyes glaze over, prompting Eeke to detail the immense difficulty of defining operating principles without relying on empty platitudes. | |
| Drafting Stripe's Cultural Guide and Managing Public Reception | 4 | 5 | 1 | 1 | Eeke recounts the controversy surrounding Stripe's internal culture guide when it leaked to Hacker News and how concrete framing made the document impactful. | |
| Case Study in Complementarity: Claire Hughes Johnson and Will Gaybrick at Stripe | 5 | 6 | 1 | 2 | Eeke uses Claire Hughes Johnson and Will Gaybrick as key examples of complementary Bert-and-Ernie executive leadership pairings balancing technical founders. | |
| Aligning Company Strategy with Executive Functional Roles | 4 | 5 | 1 | 1 | Eeke stresses that companies must understand their core growth motion before hiring functional heads like sales leaders, warning against misaligned enterprise playbooks. | |
| The Three-Part Introspection Framework Before Hiring | 4 | 6 | 1 | 1 | Eeke outlines her three-part introspection model: understanding self, understanding the team's immediate needs, and projecting the company's two-year operational future. | |
| Interviewing for Counterfactual Impact and Addressing Candidate Biases | 5 | 6 | 2 | 2 | Eeke explains how to counteract candidate pedigree bias by rigorously testing for counterfactual impact, while expressing skepticism toward standard backchannel references. | |
| Designing the Executive Interview Flow and Decision Authority | 4 | 5 | 1 | 1 | Eeke details an executive interview structure focusing on unstructured working sessions and insists that hiring decisions should never be made by consensus committee. | |
| Managing Existing Talent and Communicating External Leadership Hires | 5 | 6 | 1 | 2 | Eeke highlights the new leader dilemma where incoming executives feel incentivized to push for premature strategy pivots or reorgs simply to buy grace periods. | |
| Best Practices for Incoming Executives and Choosing Companies | 4 | 5 | 1 | 1 | Eeke advises incoming leaders to enter with deep humility, learn the real problems quickly, and fire underperformers immediately rather than delaying hard choices. | |
| Constructive Founder Disagreement and Evaluating Career Tenure | 4 | 5 | 2 | 1 | Eeke addresses founder disagreements and explains why multiple two-year stints on a resume signal mercenary tendencies and lack of resilience during inevitable downturns. | |
| Assessing Domain Matching, Company Shape, and Non-Pedigree Experience | 5 | 5 | 1 | 2 | Brett and Eeke discuss the risk of attributing success to executives who merely rode strong tailwinds at prestigious tech giants rather than driving outcomes independently. | |
| Talent Density, Firing Track Records, and High-Functioning Exec Teams | 4 | 5 | 1 | 1 | Eeke compares high-functioning executive teams to parents presenting a unified front, warning against teams airing discord publicly during all-hands meetings. | |
| Prioritizing the Executive Team Hat, Strategic Leadership, and Developing Strategy | 5 | 5 | 1 | 2 | Eeke differentiates between day-to-day managers and true strategic leaders, noting that strategic clarity is a muscle that can be developed through writing and testing. | |
| Career Reflections: Operating Models Across Stripe, Retool, and Startups | 4 | 5 | 1 | 1 | Eeke reflects on how moving between Stripe, Retool, and founding taught her that multiple valid organizational models exist for building high-performing companies. | |
| Missing Industry Data in Executive Recruiting and Leadership Ambiguity | 5 | 5 | 1 | 2 | Eeke and Brett discuss the surprising lack of feedback-loop tooling in executive recruiting to evaluate false positives and negatives across hiring cycles. | |
| Mentorship Highlight: The Product, Design, and Engineering Trifecta and Conclusion | 4 | 5 | 1 | 1 | Eeke concludes by highlighting the power of the product, design, and engineering trifecta, citing her collaboration with Ryan Lucas at Retool. |
Statements from this episode (43)
de Milliano: Executive candidates succeeded elsewhere; the challenge is fit
“Like the funny thing about all these things, like when you are interviewing someone, inevitably they were good for someone somewhere. Otherwise you probably wouldn't be interviewing them, but it's the hard part is finding the right fit.”
De Milliano: 80% of executive hiring success comes from pre-interview introspection
“And I actually think 80% of the work In hiring a great leader, who's a great fit for you, is figuring out that piece of it. Like, not even doing the interviewing, it's the, like, doing the introspection of whether this person is a good fit.”
De Milliano: Executive hiring decisions fail 50% of the time within 18 months
“And then at the end, a couple of them will have seemed interesting and like they'll have to make some sort of agonizing decision and like still 50% of the time they fail in their decision after a year or 18 months.”
De Milliano: Bad executive hires drive star employee attrition by destroying trust
“Reason number one why it's bad, but like reason number two why it's bad is because everyone looks at that bad hire or that bad fit, basically. Again, like, I don't think they're generally bad people, but like that person who isn't a good fit, and they look at …”
De Milliano: Firing executives is harder due to longer timelines and optics
“And then it's also just harder to fire them for, you know, kind of the same reasons. The stakes are very high. Like you've just spent a bunch of time getting the whole organization excited about this leader. Like honestly looks bad if you all of a sudden say l…”
De Milliano: Globally plug-and-play executives do not exist without value alignment
“The other thing that came out in all of these, like, conversations with folks is, like, if your values aren't aligned, there's, like, literally no way it's going to work. I think it's just actually pretty hard for there to be, like, globally relevant execs. Li…”
Patrick Collison designed Stripe's culture guide to repel half of candidates
“And at one point, like, Patrick Ping made me, he was like, hey, like, I really want us to write a guide to Stripe's culture, and I want us to share it with candidates when they join, when they are considering Stripe. And ideally, half of the candidates who rea…”
de Milliano: Executives copy-pasting old playbooks create a recipe for disaster
“So like my only like good litmus test for that or like red flag is if a leader comes in and they're starting to make a bunch of changes without deeply, deeply, deeply understanding the company or the company's problems and without bringing like real humility, …”
Stripe's internal culture doc was eviscerated on Hacker News
“There was some controversial, controversial, there was some stuff in there that was basically just like, you got to be willing to work really hard to actually, you know, be successful here long term. Oh my gosh, it was so controversial when it came out on Hack…”
Milliano: Large companies must accept some employees won't work extreme hours
“I do also think it's true that at some point, I don't know, companies get big enough that you have folks who maybe are just not, Up for that, and like, you just have to kind of be okay with that if you want to have that many employees in your company.”
De Milliano: Stripe nearly rejected Claire Hughes Johnson when hiring at 150 employees
“Claire joined Stripe when we were around a 150 people, and we were very, very close to organ rejection.”
De Milliano: Enduring tech companies almost always pair technical founders with operational leaders
“One of the themes that has come out of that that has been surprisingly consistent, especially with these sort of, like, deeply technical companies, is that there's almost always a pairing of, like, a deeply technical founder with a more operations people-y per…”
De Milliano: Will Gaybrick had no operating experience when Stripe hired him as CFO
“Yeah, he was an investor and, you know, incredibly impressive background, but, like, no operating experience, really.”
Milliano: Founders rarely clarify product-led versus sales-led strategy when hiring
“Almost never have I seen like a founder or an exec hire a sales leader and like actually be able to articulate very clearly, like I'm going to be a sales led company or I'm going to be a product led company.”
Milliano: Founders must lend social capital to onboard new executives
“There's work you need to do to set up the, these execs for success, a hundred percent, this, like, baseline, like, you know, give them your social capital, make sure they are introduced to all the right folks to get all the right work done.”
De Milliano: Only define executive hire success for years one and two
“I think you have to sort of be pretty concrete with yourself on exactly like what success looks like in year one and what success looks like in year two. Nothing past that because you have no idea what your company is going to look like past that.”
De Milliano: References are useless unless aligned with the hiring company
“My main view on reference is that I actually don't think they're that useful unless you can find someone who has more incentive to tell you the truth than to, like, have the back of the person they're giving the reference on and someone who really understands …”
De Milliano: Identifying poor executive performance is easier than verifying star talent
“No, I think it's easier to see when someone isn't good at their job.”
De Milliano evaluates direct reports by asking the counterfactual outcome
“If you had not been here, which is what I ask in every performance review cycle of the people who work for me, like if they had not been here, what would have happened?”
De Milliano: Team buy-in meetings for executive hires shouldn't have veto power
“And then step three is, you know, let's say they kind of get past that is, okay, now get in buy-in from the rest of the team. That shouldn't be a, like, a decision-making forum. That's more of a, hey, I want you guys to, like, meet this person and get a sense …”
De Milliano: Executive hiring decisions must never be made by committee
“I don't think any important decisions like this can be made by committee. Like they should, I mean, they should use input from all the folks who, you know, were part of the interview process, but ultimately the founder has to decide or the hiring manager.”
De Milliano: Executive hires stretching up succeed more than those stepping down
“I think you're way more likely to be successful when someone is stretching up into the role because they're going to have a chip on their shoulder. And like, you really want them to prove themselves or they want to prove themselves.”
Milliano: Retaining passed-over talent requires hiring genuinely inspiring leaders
“Truly the best thing you can do is hire an incredibly inspiring leader. Really great people want to work for really great people and learn from really great people.”
Milliano: Radical transparency about readiness gaps helps retain passed-over talent
“The second best thing you can do, I think, is just be super transparent and open throughout the process. Like, really good high performers want to hear how they can get better. Generally telling them, like, look, you're not ready for this role, and here are th…”
de Milliano: A bad executive culture fit is obvious within three months
“If they're, like, a bad culture fit, three months max.”
de Milliano: New executives face massive incentives to change company strategy
“New leaders have in almost every single scenario a huge incentive To say that they need to change the strategy.”
de Milliano: Reorgs by new leaders rarely solve underlying organizational problems
“It feels like you're doing a lot as a new leader because you're doing this big reorg and everyone's talking about it, but Like rarely is that really the answer to solving your problems.”
De Milliano: Incoming execs should immediately fire flagged mediocre employees
“Assess the talent pool pretty quickly. Like, just fire the people that aren't good. Especially if they're not a good culture fit, but also if they're just not doing well. One thing I have experienced myself, but also I've, like, seen with other leaders, like, …”
De Milliano: Executive hires are like arranged marriages, not love marriages
“The way I've described leadership hires at companies, it's like, it's kind of like an arranged marriage. You both really have to choose to want to, like, make it work. It's not like a love marriage where, like, you know, which is like what I think happens with…”
de Milliano: Multiple consecutive two-year stints signal mercenary executive behavior
“I personally really worry about the, like, the two-year stints, sort of, like, multiple, like, two-year stints. Like, it just actually isn't enough time to show that you've done anything significant, I think, as a leader. So, like, this is a gross generalizati…”
de Milliano: Long executive tenures prove resilience through inevitable hard times
“The leaders who have, like, been at companies for a long time, I think, generally, Very highly of because inevitably those companies have gone through hard times. Like there's no way a company didn't over a nine year stint, and that to me really says something…”
de Milliano: Executives from only one prior company risk copy-pasting playbooks
“But a leader who's only been at one other company, I think I'd always have a few questions about because they're going to be very tempted to copy paste everything that they did.”
De Milliano: Purely successful resumes make it hard to judge executive impact
“The folks who have only been at companies that have themselves done well, it's just really hard to be able to distinguish whether the company did well because of the founder or because of the leader, sorry, or the leader did well because of the company.”
De Milliano: Former colleagues following an executive is a strong hiring signal
“How many people moved to the next company that you worked at, that you worked with before? I think it's always a really, really good sign.”
De Milliano: Executives with firing experience execute necessary terminations faster
“Per your point, if the, if you just have to assume that the distribution of failures is, like, pretty much the same across the org, I think it's always a pretty good sign if people have fired a lot. It's only because, like, they're gonna have to in whatever jo…”
De Milliano: High-functioning executive teams maintain unified consistency like parents
“A high functioning executive team is like that. They're like, they're consistent. You feel like you're going to get the same answer from every single executive, but you also know that like the how they do it or like how they're going to get it done is like the…”
De Milliano: Executives must prioritize the leadership team over their functional departments
“Your main team has to be the executive team over your functional team, even though I think it's very tempting to want to, like, Spend more time with your functional team.”
De Milliano: Executive charisma does not require public speaking if leaders excel in writing
“I know very, quote-unquote, charismatic leaders who are not incredible speakers, but are great writers, or are wonderful one-on-one. So like, you have to be able to get people behind the thing that you believe, and people have to want to follow you, but it doe…”
de Milliano: Retool had 10 operating execs while Stripe relied on five
“Retools leadership team was like a collection of very different personalities. It was a big team was like, you know, I think they had 10 people on sort of the overall operating leadership team. Stripes team was always tight knit, five people.”
de Milliano: Starting an early-stage company doesn't teach executive leadership
“I don't think you learn much starting a company early on about being an executive.”
De Milliano: Interview tools fail to track candidate ratings against eventual performance
“I think the thing that's like, it's weird to me that no interview tool has done this, but like really like you should be able to measure or like track like interview feedback to like how a person actually ends up doing at the company and their talent cycle. I …”
De Milliano: Problem ambiguity scales exponentially up to the C-suite
“I think it's ambiguity or problem. It's just like, it's, that scales up exponentially. Yeah, they sort of, I can't speak to the specific titles, but like the most ambiguous problem should be at the like C-suite level and everything kind of scales down from the…”