How to Control Your Elite Executive Interview

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Good Golly, Miss Molly—here we go again with more content about interview preparation. 

I’ve previously belabored my disdain for generic intel about interview preparation in an earlier article—but now, ChatGPT is quickly picking off the low-hanging competition for any SEO-friendly content that spouts the obvious interview advice of “RESEARCH THE COMPANY.” 

Since everyone suddenly has a hot take on artificial intelligence—here’s mine. I am a scummy trend conformist, after all…

I’m equally bummed and stoked about AI chatbots and writing assistants running our online content barren and devoid of notable unique perspectives.  

I am bummed because, holy hell, anyone can crank serious content out in about 5 minutes and get generic answers that will satisfy the needs of about 80% of readers. Indeed this will be abused for evil, and more great folks will get duped into overpaying for fly-by-night experts, gurus, and icky career coaches. (Obvi not me, okay?)    

I am stoked because anyone pumping low-effort content (I’m looking at you too, “LinkedIn Influencers”) will be accused of being an AI BOT-using fraudster. Surely this will inspire the readers of this highly-esteemed publication to acknowledge their intellect and curiosity towards reading custom and unique content. 

There has never been a better time to stand out by being different with written content. So now, picture me with a flirtatious beguiling shit-eating grin on my face. I’m ready to go! 

Enough of me blowing smoke up your ass—today’s article is about fascinating observations I’ve picked up regarding interviewing and networking performance across my diverse spectrum of executive client experiences. 

Such as with many of my career diatribes, I’ve created a provocative rule of thumb that you can use to assess your interview prep performance and take action immediately. 

Let’s call this the 25-50-75-90-99 rule. Cause why not? 

Odds are, if you’re a frequent reader of Execs and the City, you’re likely using some of these activities from elite performers—but unlikely all. So take the W and feel good about yourself.   

And if you’re under the 25th percentile, you’re likely winging it—like a reckless, pompous know-it-all—which, to be honest, will still get you six-figure jobs, but you’ll probably hate the team that fell for your shenanigans. (I’ve got living proof).

PS. If you’re the type that hates reading long articles and sexy prose, grab some popcorn and watch The 5 Steps To Interview Mastery event that Loren Greiff recently drilled me on. This article is long.

How The 25th Percentile Prepares For Interviewing

For this section, I’ll ask ChatGPT to do the work and make an example of this nonsense. 

Yes, I’m arrogant enough to suggest that this strategy is equivalent to autopilot. However, artificial intelligence can directly match these generic efforts—and if this is where your interview preparation stops, I’d argue that you’re in the lower 25th percentile of applicants. 

In a recession-feared economy, applicants with weak research and poor positioning will agonize over job searches and spend a long time being broke. 

You must level up or wither on the vine if you fall into this trap. The robot army is out to get you.

*Please note: The following excerpt is directly copied and pasted from ChatGPT. All grammar errors are the fault of the bot, not me! Get used to this level of occasionally helpful but typically generic support flooding your inboxes and notifications at an accelerated rate.

I asked ChatGPT, “How should I prepare for an executive interview?”

ChatGPT obliged in ~15 seconds. 

“Here are a few tips to help you prepare for an executive interview:

  1. Research the company: Look into the company’s history, mission, values, and recent news or developments. This will help you understand the company’s culture and goals, and give you talking points for the interview.
  2. Review your qualifications: Make sure you understand how your skills and experience match the requirements for the position. Be prepared to give specific examples of how you have demonstrated these qualifications in the past.
  3. Practice your answers: Anticipate common interview questions, such as “why do you want to work for this company?” or “what are your greatest strengths and weaknesses?” and practice your answers out loud.
  4. Prepare questions to ask: An interview is also an opportunity for you to learn more about the company and the position. Come up with a list of thoughtful questions to ask the interviewer.
  5. Dress professionally: Make sure to dress appropriately for the role and company culture.
  6. Be punctual: Be sure to arrive on time for the interview and plan your travel time in advance.
  7. Practice your body language: As a executive leader, your body language is important, it can say lot about your communication and leadership style, confidence level and overall demeanor. Practice having open and confident body language during the interview.
  8. Follow up: After the interview, be sure to send a thank-you note to the interviewer, reiterating your interest in the position and how you can contribute to the company.”

End ChatGPT answer.

For what it’s worth, there is some helpful information that ChatGPT provided, especially about body language (executive gravitas and presence indicator). Sure it’s void of the details and how to take action, but it’s not a complete bastardization of what you need for interview preparation. 

However, you must dig deeper to compete with elite executive talent. Everything above is table stakes.

For the remainder of the sections, I will concentrate on how elite executives conduct people research, more so than company research. It’s the people that you need to spend the most time understanding to win. 

More specifically, how the elite execs game plan around the people within the company to master interviewing using compassion, empathy, psychological persuasion, and ownership of the dialogue. 

Note: Each section builds upon the other. So you’re not replacing the activities of the prior section; you are adding or shifting more attention to the new interview preparation activities. Building upon prior activities is critical because your information-gathering habits are FUNDAMENTAL if you hope to dominate 7-figure negotiations later.

Now I’ve set the stage to stop tripping over the curb-height industry standards. It’s time to raise the bar of your interview preparation to at least hurdle height—and start meeting the average. 

Let’s talk about how the 50th percentile prepares.

How The 50th Percentile Prepares For Interviewing

It’s well-documented that comparison is the thief of joy; however, we’re also told that we become more like the company we keep. It must be a lizard-brain human survival thing.

The 50th percentile of job searchers surrounds themselves, engages with, and is comfortable talking shop with more people like them. (E.g., same title, responsibilities, or within reach, etc.).

For example, let’s say you’re a Vice President of Product. 

First of all, good for you; that’s a hellaciously complex and demanding job. If you’re in the 50th percentile of Product leaders, you’ll surround yourself with other Product leaders to learn and grow.  

Excellent, you’ve got the growth mindset, and you’re developing the habits that will lead to further aspirational progress.

Hell, you may have even joined a community like the Product Collective or Product Marketing Alliance or grabbed a membership at Reforge. And if you’re an extraordinary sort of try-hard, you’ve tapped into LinkedIn Premium, where you use your InMails to connect with, and network with other Product leaders via Zoom and coffee meets. 

You’re a baller.

For my sales, marketing, and CS friends, this is a significant value driver for joining a community such as Pavilion. You’ll have access to a grip of high-performance revenue professionals at all stages in their journey while working inside hyper-growth, largely VC-fed startups. 

There’s a lot to learn here. But you will only maximize your value with these folks if you have a bias for action. 

For example, my buddy Adam Ferris takes every opportunity to learn (even across functions). That’s why he’s constantly snapped up in the obligatory screenshot across each Zoom class. His camera is on, he is front and center attentive, and I swear he must go through a notepad a day with his dedication to learning. 

I digress.

All of this is excellent progress and smart. You’re fast-tracking your functional expertise. However, you can be the best damn functional leader—or friggin’ industry savant/guru, if you will—and can still lose your job every 18 months. 

What gives?

The world moves faster than you. Innovation happens faster than your ability to retain information, learn, grow, and adapt. Especially at startups. (Also, let’s be honest; there are a lot of shit companies with hair-brained ideas out there.

You’re lagging if you’re only surrounding yourself with more of the same.

You’re learning from and studying what it means to be great at your function. Of course, there are apparent exceptions and nuances to this, but by and by, this is how it works when we too often target based on functional criteria.

Furthermore, your network will likely consist of these similar folks (often your competition) when you prepare for interviews. 

In an interview preparation context, that means you’re heavily influenced by:

  • What’s worked for others in your role; not always your experience.
  • The tried and true frameworks established by other leaders; not typically the methods you’ve developed through your own critical thinking and experience. (Taking too many shortcuts can make it challenging to appear authentic during interviews).
  • Templatized, impersonal, and context devoid 30/60/90 day plans and boilerplate messaging.
  • The status quo and industry average compensation benchmarks. (You’re comparing yourself to the average—they are called benchmarks, after all).

Everything you need to meet the bar is available at your disposal. 

You can copy and paste someone else’s strategy and find success—but you’re not moving forward. And let’s not pretend we can stand behind using the word innovation, cutting-edge, or world-class on our resumes. 

If anything, you’re just a smidge behind the 8-ball. 6 months? 12 months? 18 months? It depends on the company you choose to keep.

I’m not poo-pooing these resources or communities. They are irreplaceable and fundamental to your success. 

I’ve found that there will always be continuous value in accessing functional resources, preparing for functional interviews, having a functional understanding, and maintaining a bead on the market—especially as we innovate and grow at a pace never experienced before.  

But the nuance is, “To what degree do you rely on a single source of information?” Functional support is just one tool in the greater utility belt of elite executives. 

You can see where I’m heading with this. 

So let’s dive right into the 75th percentile and how they build their network and prepare for interviews.

How The 75th Percentile Prepares For Interviewing

As executives in the 75th percentile begin to dominate their functional expertise, they spend less attention with those at the same level or with the same background because they’ve more or less tapped that knowledge pool. (They do not remove it; they throttle it down).

They begin moving cross-functionally to understand executive leadership across the business to continue their growth. 

Ultimately, if you hope to keep your job longer than 12-18 months, it’s not enough to be a 1-3x multiplier. You must target 5x. 

Bonus points if you can measure your performance, communicate your (and your teams’) impact up the ladder, and influence laterally across the business. Now I’m teasing part of what the 90th percentile is doing prematurely… 

In a networking context, the 75th percentile connects outside of its function. HR leaders are having conversations with Product. Sales leaders are talking to Engineering leaders. Design leaders and meeting with Comms executives. You get the gist. 

They learn how to work together—even if it’s not immediately obvious how or why they should—and even when it’s not expected for them to do so. It doesn’t need to be in the job description to take action.

The mantra here is to treat everyone you meet as if they know more about something than you do. Because they do. 

The respect you share will pay your career compounding dividends (if you’re thinking about all this with a selfish ROI first, world-domination lens). PS. Sup, Bezos, thanks for reading. Text me, bro.

In an interview preparation context, this means you:

  • Study all the individuals who make up the leadership team, not just the folks you’re interviewing. They have inside information that’s valuable (and important for your red-flag sniffing and ongoing negotiations).
  • Research company insights and recognize the hiring trends of the organization. You can tell what challenges a company is working through by their hiring patterns. (E.g., hiring many sales professionals clearly indicates their need to grow quickly and satisfy investor demands; firing a CMO may suggest that their marketing is not meeting expectations).
  • Exercise critical thinking about what each leader may need help with for the business to succeed, not just what they need from your functional expertise.
  • Maintain a working knowledge of the true meaning of empathy and compassion (not simply talking about it because it’s expected of you).

We’re getting deep here—let’s keep the momentum. I hope you’re taking notes; I know Adam is.

How The 90th Percentile Prepares For Interviewing

As executives continue to grow into what I call “rarefied air,” all of the aforementioned is an effortless habit. 

They become experts at seeing around corners, making bold company assertations with limited information, and are masters of their domain. 

I suspect this is because they have spent a decade+ honing their networking and interviewing habits. As a result, they have a smart—or method-based system to balance learning from outside sources and learning by doing—across all functions. Sorta like a streamlined 360-degree view of how businesses work.

In other words, they are eagle-eyed and optimized AF.  

When all of these activities become effortless, this creates the mental bandwidth they need to grow into the upper echelons. As a result, meaningful C-suite opportunities become more prevalent. (I’m not talking about inflated C-suite titles at early-stage companies—you can nab these deals when you’re still in the 50th percentile.)

In a networking context, the 90th percentile primarily connects with C-suite leaders, investors, board of directors, and CEOs. A surefire way to maximize your perspective is to sit cross-legged on the floor while a CEO relives flashbacks from the war. 

In an interview preparation context, the 90th percentile:

  • Ask the most profound open-ended questions that cut to the core of others that hold positions of magnified influence and authority. A confident and no-nonsense approach illustrates that you know what’s happening with the business and don’t fear high-profile leadership.

For example, you’re interviewing with a CEO, “I imagine that you’re feeling pressure from the board to deliver during the recession; we’ve missed the last three quarters—what must be true for you to regain your authority in the next board meeting?” 

Or, if you’re ready to potentially Kamakaze your career with boldness, “What must be true so you keep your job? Am I the hail-mary you need to 3x sales and get the vision back on track?”  

The 90th percentile…

  • Are stacked with information and augment their knowledge with their own experiences and presumptive assertations. They demonstrate their expertise; they don’t simply talk about it. 

For example, you don’t need to tell the company that you read their Crunchbase details or 8-K filing. They know this information in and out. They live it every day. They won’t learn anything from you if you bring stale information up. You must make the available company data part of your daily life to win the opportunity. 

Now let’s go deeper… 

Let’s say you’re interviewing for a $200M ARR Series D company. You may not have public information regarding their next steps, but it’s generally safe to assume that they want to grow more. It’s safe to assume that investors will pressure the company to get their money back after four rounds of investment and cascading board additions. It’s safe to assume the CEO wants that too. 

The money machine squeezes everyone—and it’d serve you well to open your eyes to it and go to battle.

How do we insert your expertise and show that you’ve done your research? (I’m making these numbers up, by the way).

“We’re at $200 million in revenue today—in my experience, the sweet spot for an exit is when we hit $400 million. The companies that make this happen with the most impressive valuations manage to transform repeatable revenue growth into predictable growth. In other words, yes, it’s about flawless execution, but they’ve stacked the deck in their favor. The market will yield to their moves, and it’s only a matter of time before that big exit comes along. So what are you doing today to ensure $400 million is not IF but WHEN? And is $400 million the target—or are you thinking bigger? I anticipate this is the big problem I’ll own.”

Now you’re in a position to show empathy for leadership and understand what needs to be done. You’ve framed the challenges from a more imaginative 360-degree-esque perspective and at least provided the perception that you can help them achieve the desired outcome. 

The 90th percentile…

  • Go first.  
  • Are assertive. No added context is needed; read the links for more info.
  • Use conversational ownership and psychology to orchestrate masterclass interviews.

Conversational ownership and psychology are next-level interview tips that make my clients slack-jawed when I dump a tirade about what’s possible for them. 

It’s cool stuff, and it applies to your interview preparation. Try this next time.

  • Everyone’s favorite word is their name. Strategically use their name in conversation to elicit emotions of warmth and attention. “Will! So ready to have an engaging conversation with you…”
  • Teams get to know each other over time, and they call each other by names and nicknames. When you’re interviewing, you’re the outsider. Learn the names (and pronunciations) of the team. I recommend learning about the folks on the outer edges, too, even if you’re not interviewing with them. “Do you anticipate that I’ll work with Susan and Darryl on next quarter’s OKRs?” You start to sound like you’re already a familiar member of the team. 
  • Always position yourself in a favorable scenario somewhere in the future as part of the team. The 90th percentile knows how to create a vision for the future that they will lead. The hack here is to keep the conversation forward-thinking and use names and “we” often. Align yourself and associated names to the favorable outcomes outlined by the company. 

For example, “I anticipate that Jessica, Steven, and I will correct the marketing operations challenges by June—and we will move on to further fuel the sales pipeline. When we accomplish this, we’ll scale to finish the year strong and tackle product marketing for a refresh.” .

You don’t have the job, yet—but you’re positioning yourself as the solution in the future.

Too often, candidates approach interviews with a ME vs. COMPANY perspective. 


ME VS. YOU is ass-backward (especially for your negotiations later). It’s your job to remove boundaries, iron our friction, and get cozy with the team. Picture yourself sitting next to the interviewer, not across from them. They are your advocates and want you to succeed. Make it known.


How The 99th Percentile Prepares For Interviewing

Hot damn. The top 1%. That sounds friggin good—and I’ll have some of that. 

But to be honest, I’ve only had a few clients that meet these criteria—and I don’t know what I don’t know, so technically, those clients could actually be the true 96th percentile or something, and I wouldn’t know it. But that doesn’t get the clicks. So top 1% it is.

From my experience, the most elite executives:

  • Connect with and study C-suite leaders, high-potential executive risers, investors, headhunters, board members, influencers, and other power players across industries and diverse communities and perspectives
  • Listen to understand. They aren’t simply waiting to insert a prepared talkative script if the door is open. You learn more by listening—and your answers will better reflect the knowledge you gain by listening.
  • Take almost awkwardly long pauses before answering questions. They aren’t quick to reply. They ask more profound questions to understand HOW to answer questions. I’m convinced they don’t always know the answers, but they do know how to get the information they need to answer correctly. Nuanced detail—but it makes a huge difference in their performance. 
  • Exercise conversational mastery. Elite execs don’t waste time fretting about what questions will be asked of them—because they know how to stop the conversation in its tracks, buy time, ask more clarifying questions before showing their hand, answer the questions later, and use all of this control to their benefit.
  • Connect with and study the customers of the companies that they are considering as their next step. They have insider knowledge. I rarely see anyone doing this, but these clients perform at another level when I do see it.
  • The top 1% are familiar with, have an opinion on, and can confidently execute through market headwinds, legal policy changes, and trends from global hyper-growth and disruptive industries (e.g., artificial intelligence, genome sequencing, robotics, blockchain technology, energy storage, etc.). 

There you have it—a complete drubbing of intel I’ve collected about elite interviewers and networkers over the last several years. I’m confident I’ve missed plenty, and I’m highly interested in the areas you disagree with or have additional color to add. 

But more importantly, I missed a lot less than you, ChatGPT—you demon robot you!

Thank you for reading my longest post yet. Today’s writing took me about 6 hours, which is 3x the usual, so I’d value you sharing this with your executive friends navigating interview hell right now. Plus, I had to make up for sending you a shameless email about our first public CORE Connect event a few days ago. 

Until next Thursday!

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