From 20 years of C-suite placements at Google, ElevenLabs, and billion-pound scale-ups.
Start hiring the right people.
The exact questions and workshop framework I use before placing any C-suite executive. The ones that show you who someone actually is, before you make a decision you'll spend the next six months regretting.
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The interview that changed how every hire after it went
THE PROBLEM
I see it every single week. A hiring manager sits across from a candidate with an impressive track record. Fifteen years of experience. Strong references. Articulate, confident, prepared.
They walk out thinking: that's our person.
Six months later, they call me. The team is frustrated. Targets are being missed. The hire that felt so right is quietly becoming the most expensive decision they've made all year.
The problem is never that the candidate was bad at their job. The problem is that the interview was never designed to find out.
What most interviews measure
How well did they prepare for this interview?
A standard interview tells you none of this. Unless you know which questions to ask.
What you actually need to know
How do they behave when their thinking is challenged? Do they make the people around them better? What do they do when something goes wrong on their watch?
What's inside
16 INTERVIEW QUESTIONS THAT HAVE NOWHERE TO HIDE
Organised into four categories: how they challenge thinking, how they operate in a team, how they own outcomes, and whether their ego will cost you. Each one comes with what you're listening for, because the question is only half of it.
THE WORKSHOP FRAMEWORK
For senior hires, one interview is never enough. This is the 60-minute workshop structure I use to see how a candidate thinks under pressure, behaves in a team, and responds when the ground shifts. You cannot get this from a boardroom Q&A.
THE "AND THEN WHAT?" TECHNIQUE
How to push past polished non-answers and get to what actually happened. Most candidates are trained to describe situations. This technique gets you to the decision, the outcome, and the number.
THE OBSERVER SCORECARD
Seven signals to measure during the workshop. Brief a peer observer to score silently in real time. The candidate who scores well here is not always the most impressive on paper. Which is the whole point.
Real results
These are real candidates I've worked with. Different industries, different levels. Same exercise. Same shift in results.
Before
"We kept hiring people who interviewed brilliantly and then struggled to build anything. We didn't know what we were missing in the process."
AFTER
"We added the workshop round for every senior hire. The first time we ran it, the candidate we were going to offer the role performed poorly in the group setting. The second-choice candidate was outstanding. We hired them instead. They're still there two years later."
RESULT
Zero C-suite departures in 24 months.

Series C SaaS, 300 employees
Before
"Our interviews were basically a conversation. We liked the person, they seemed right for the culture, we made the offer. Our attrition at director level was close to 40%."
AFTER
"The accountability questions changed everything. We started pressing for specific examples instead of accepting general answers. Three candidates we would have previously hired couldn't answer question nine. We didn't hire them. The ones who could are still performing."
RESULT
Director-level attrition dropped from 38% to 11% in 18 months.

Post-funding fintech, 150 employees
Before
"We had a pattern of hiring confident, senior-sounding people who turned out to be very good at talking about work rather than doing it."
AFTER
"The ego and psychological safety questions changed our shortlisting completely. We stopped being impressed by confidence and started being impressed by self-awareness. The quality of our senior team has shifted noticeably."
RESULT
Last three C-suite hires still in role. Board signed off on two promotions within the year.

B2B tech scale-up, 80 employees
"We kept hiring people who interviewed brilliantly and then struggled to build anything. We didn't know what we were missing in the process."
"We added the workshop round for every senior hire. The first time we ran it, the candidate we were going to offer the role performed poorly in the group setting. The second-choice candidate was outstanding. We hired them instead. They're still there two years later."
Zero C-suite departures in 24 months.
"Our interviews were basically a conversation. We liked the person, they seemed right for the culture, we made the offer. Our attrition at director level was close to 40%."
"The accountability questions changed everything. We started pressing for specific examples instead of accepting general answers. Three candidates we would have previously hired couldn't answer question nine. We didn't hire them. The ones who could are still performing."
Director-level attrition dropped from 38% to 11% in 18 months.
"We had a pattern of hiring confident, senior-sounding people who turned out to be very good at talking about work rather than doing it."
"The ego and psychological safety questions changed our shortlisting completely. We stopped being impressed by confidence and started being impressed by self-awareness. The quality of our senior team has shifted noticeably."
Last three C-suite hires still in role. Board signed off on two promotions within the year.

Your guide
Founder, Obsidian Black · Host, The Secrets of Tech Outliers
20 years placing C-suite executives into companies like Google, ElevenLabs, and scale-ups that went from seed to billion-pound valuations.
Most of my work happens under NDA. The placements that move share prices and secure nine-figure funding rounds don't come with press releases.
The single biggest reason senior hires fail has nothing to do with capability. It's that the process used to hire them wasn't designed to find the right person. It was designed to find the most impressive one on the day.
This framework is what I use before every placement. Now it's yours.

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