The Due Diligence Companies Hope You Skip
They gather intelligence you'll never see while selling you curated narratives. How to investigate companies with the same rigor—and why choosing beats being chosen.
Welcome to Execs and the City, where we reveal how elite leaders create an unfair advantage in their careers. Paid subscribers get exclusive perks like our complete toolkit, including full access to our guides and powerful career tools.
You spent 4 months in their process.
Multiple interviews. Presentations. “Culture fit” conversations.
They ran background checks, called references, analyzed your LinkedIn activity, and probably had three internal discussions about your compensation expectations.
You?
You read their website, asked some questions during interviews, and got excited about the vision they sold you.
Three months in, you discover the “collaborative culture” is political warfare.
The “visionary CEO” micromanages font choices.
The “growth opportunity” is a sinking ship everyone’s quietly abandoning.
You conducted a transaction. They conducted an investigation.
The consequences aren’t symmetrical.
Let’s play devil’s advocate and say they made a bad hire.
Annoying, but survivable.
They’ll course-correct in a few quarters if they’re small—and may not even notice if they’re big.
You?
You can’t pay your mortgage. Your family’s plans are disrupted. Your career momentum just reversed.
This is even worse after a relo across the country. Ouch.
They weather hiring mistakes. You live with career disasters. And remember, the blame is always on you as the candidate
The problem isn’t that you chose wrong. The problem is you never actually chose at all.
This Happens at the Top Too
A friend of mine left a strong role for a compensation package well into seven figures at a company that’s a career maker. A logo that gets you favored attention forever.
The scope was exactly what she wanted—a level where she could make a difference.
The interviews were flawless. The leadership seemed aligned.
She accepted—and left a very lucrative role where she had years of tenure, respect, and something else—a deep understanding of the path forward and how to protect herself in that environment.
Sometimes the devil you know is better than the devil you don’t.
Just weeks in, she discovered the reality they’d carefully avoided mentioning.
Expectations across the organization were set at 4x what anyone on the team could deliver.
This wasn’t ambitious goal-setting—it was organizational delusion—fueled by the artificial intelligence nuclear arm’s race we all navigate.
And all of this during a market that’s been squeezed for years.
The autonomy she was promised?
Gone.
Every missed expectation—and there were many, because the expectations were impossible—triggered micromanagement and second-guessing.
And the worst kind—a second-guessing of self.
If you’re anything like me, not reaching a goal is an identity crisis. How can someone who always exceeds quota, exceeds the seemingly unattainable—suddenly be in the bottom quartile?
The seven-figure comp doesn’t matter when the role is professionally untenable. And the golden handcuffs constrict your blood flow.
How do you spend the rest of your career explaining a sub-one-year tenure at a marquee company? Clearly the problem is you, everyone loves them.
Every future interview, every background check, every reference call—this will come up.
Later we realized that this position had turnover 4 times in the last 18 months.
Former employees would have described the expectation chaos. Back-channel references would have revealed the impossible targets. The market conditions were public knowledge.
But in the excitement of what seemed to be the biggest opportunity of her career—and combined with mounting pressure from the employer to make a hasty decision—much of the standard due diligence on her part was forgone.
I’ve said it before and I’ll say it again, haste equals risk.
Now we must tackle this blip in the game plan head on.
The Psychology of Choice Requires Information
The psychology of choice is well-documented.
People who believe they’re choosing feel more satisfied, perform better, and commit more deeply than people who believe they were selected.
Research on autonomy and motivation shows that the perception of choice—not just having options, but actively evaluating and deciding—fundamentally changes psychological engagement.
Yet most executives surrender this psychology before they even start.
They position themselves as candidates hoping to be chosen rather than decision-makers evaluating options. Perhaps because most of our careers we’re in a subservient position where we’re hoping to be chosen for ambitious projects.
I call this phenomenon dangling the carrot.
We wait for or try to influence a leader ahead of us to share a carrot with us so we can climb the ladder too. Yucky metaphor, but you get the gist.
The dynamic of choice vs being chosen breaks down for everyone when you don’t have the right information. You can’t choose between options you don’t fully understand. And hiring processes can be optimistic at best and deceptive at worst.
What feels like choice becomes manufactured consent—you’re saying yes to a curated narrative, not making an informed decision.
This is information asymmetry in action.
Companies hold vastly more information than candidates.
Research on labor markets shows employers systematically gather intelligence about you while carefully controlling what you learn about them.
They deploy recruiters, conduct background checks, run reference calls, analyze your online presence, and hold internal strategy sessions about your compensation expectations.
You get polished interviews and a benefits PDF.
The power dynamic only shifts when you recognize a fundamental truth.
Interviewing is incomplete due diligence.
Real evaluation happens outside the interview room—through back-channel references, former employee conversations, and intelligence gathering that reveals what companies hide.
Companies that deserve your talent welcome scrutiny. Those that don’t reveal themselves through resistance.
Why Companies Hide Information—and How It Costs You
The psychology works through several deliberate mechanisms:
Reciprocity that undermines investigation
Companies give you their time and attention during interviews. Multiple rounds. Thoughtful questions. Maybe even a nice lunch.
This triggers psychological reciprocity—you feel obligated not to probe too deeply or seem “difficult.”
This is Robert Cialdini’s reciprocity principle weaponized against your interests.
They invest in wooing you, so you feel ungracious investigating them thoroughly. But gratitude isn’t due diligence. Their generosity with time doesn’t earn them immunity from scrutiny.
Authority positioning that reverses power
Organizations position themselves as evaluators while you position yourself as the evaluated.
This dynamic shapes everything that follows.
Research on power dynamics in negotiations shows that whoever asks questions controls the frame. Yet candidates typically spend 80% of interview time answering rather than investigating.
You can’t choose from a subordinate position. The moment you accept “being interviewed” as your role, you’ve already lost the psychology of choice.
Commitment that prevents real evaluation
Once you express interest—and you have to express some interest to advance in the process—you become more psychologically invested in proving that interest was justified.
This cognitive trap can make you overlook red flags.
Acknowledging problems would mean admitting your judgment was flawed. So you rationalize instead of evaluate. You explain away concerns instead of investigating them.
By final rounds, you’re not assessing anymore. You’re hoping they choose you.
The cost compounds
Leaders accept roles beneath their capability. They join dysfunctional organizations. They walk into career disasters—all because they confuse being selected with choosing.
The companies that hire effectively get offers accepted based on controlled narratives. The executives who build lasting success conduct investigations that reveal truths those narratives obscure.
Then they choose. Or they walk away.
Information doesn’t just help you decide. It repositions you psychologically as someone who decides.
You need to understand where the bodies are buried before you join the org—and that means asking tougher questions and collecting deeper intel during the hiring process.
Your Due Diligence Playbook
Here’s how to gather the intelligence that enables real choice:
1. Create Multiple Options Before You Start Investigating
Choice psychology only works when you have actual alternatives. And remember that, “no” is your most powerful alternative and always in your back pocket. No deal is better than a bad deal.
Never investigate a single opportunity—you’ll rationalize whatever you find.
Run 3-5 serious conversations simultaneously.
I know what you’re thinking.
“That sounds great, but the market is brutal and I’m just hoping someone will choose me.”
Fair.
But here’s the reality—even when prospects look bleak and you really are hoping to get chosen, you can still use language to give the perception of choice. Companies don’t know how many other conversations you’re having unless you tell them.
They respond to how you position yourself.
When they ask about your timing—and they will—use language like: “I’m discussing a few opportunities and expect to make a decision within four weeks” or “by the end of Q1.”
Notice: you’re “making a decision,” not “hoping to receive offers.”
The framing matters.
And this is exactly why you must always build pipeline for yourself—even when you’re employed, even when you’re happy.
Put irons in the fire constantly. They all mature at different times.
Things change fast. AT WILL employment means what it says on both ends.
The executives who maintain negotiating power aren’t luckier. They’re never starting from zero. They’ve been having conversations for months before they need them.
If you’re reading this from a desperate position, start now for next time. And even from desperation, investigate thoroughly. The psychology of “I need this to work” makes you overlook red flags that will destroy you later.
“I need this” is when investigation matters most.
2. Run Back-Channel References Before Final Rounds
Don’t wait until after the offer. The moment you’re interested, start gathering intelligence.
Identify people who left the company in the past 12-24 months. LinkedIn makes this trivially easy.
Reach out with simple messaging: “I’m exploring an opportunity at [Company] and noticed you worked there recently. Would you be open to a brief conversation about your experience?”
Former employees tell truths current employees can’t.
Ask specifically about why they left, what they wish they’d known before joining, and whether they’d return if the opportunity arose.
Script to use:
“I’m not asking you to trash your former employer. I’m trying to understand the reality behind the polished interview process. What’s one thing you wish you’d known before you joined?”
This question works because it acknowledges you’re looking for insight, not gossip. Most people will be remarkably honest. As a bonus, you can use this to inform your interviews and win the role too.
3. Interview People Who Turned Down Offers
This is intelligence gold but can be challenging to find.
People who declined offers after going through the full process have seen behind the curtain and decided to walk away.
Find them through LinkedIn connection mapping, by asking recruiters directly (good ones will tell you), or through industry networks and professional groups.
These conversations reveal what made thoughtful people say no—exactly what you need to make an informed choice.
4. Mine Intelligence Platforms Strategically
Glassdoor and Blind pioneered crowdsourced company intelligence. Now platforms like Whispered enable confidential insights about specific companies and roles without revealing your interest.
Use these strategically to understand:
Real compensation ranges beyond sanitized market data
Internal politics and cultural realities
Why specific roles opened up (and how often they open up)
Which leaders people actually want to work for
Don’t read reviews like gossip—read them with a keen eye. Not everyone’s opinion matters—but a handful of people saying the same thing isn’t coincidence.
5. Map the Leadership Exodus Pattern
Pull up LinkedIn and track leadership tenure and departures. This takes 15 minutes and reveals patterns HR will never voluntarily discuss.
Watch for:
Multiple executives leaving within 6-12 months = major red flag
New CEO with immediate C-suite turnover = culture transformation (translation: chaos incoming)
Long tenures across leadership = either great culture or limited growth opportunity
My friend’s situation? Four people in her role in 18 months.
Is the common denominator the people or the company?
6. Ask Questions That Expose Hidden Truths
During interviews, deploy questions designed to surface what they’re hiding:
“Why is this role open right now? What happened to the last person in this position?”
“I’ve noticed [X leader] recently left. How has that transition affected the team and strategy?”
“When I speak with people who’ve left the company, what am I most likely to hear?”
That last question is particularly powerful.
It forces them to address potential negative feedback preemptively and reveals how honest they’re willing to be. More importantly, it positions you as someone who’s investigating, not auditioning.
7. Investigate Before You Negotiate
Never enter compensation discussions without understanding:
Recent funding status (startups) or financial health (established companies)
Competitive positioning and market pressure
Internal compensation philosophy and recent changes
Whether they’ve had trouble filling this role previously
This intelligence transforms negotiation from guessing to informed strategic positioning. But more than that—it reinforces your frame as someone evaluating whether to choose them.
Choose or Be Chosen
The most expensive career mistakes happen because executives trust curated narratives instead of conducting independent investigations.
Remember—they can weather a bad hire. You can’t weather a bad career decision—at least not without preventable headaches
The asymmetry of consequences demands asymmetry of preparation.
I’m working with multiple people through this exact challenge right now—helping them control the narrative after accepting roles based on incomplete information.
It requires direct and intentional narrative control (see last week’s article for tactics). But we’re solving problems that may have been preventable with information that was publicly available.
Companies that deserve your talent welcome scrutiny. Those that don’t reveal themselves through resistance.
Stop getting interviewed. Start choosing.
You can’t choose what you don’t understand. You can’t understand what you don’t investigate.
Don’t make life-changing decisions based on what companies want you to know. Make them based on what they hoped you wouldn’t discover.
If this article helped you, consider upgrading to a paid subscription to unlock all of our content and subscriber perks. You’ll get access to our toolkit, including deep interview prep, expert courses, and free resume and LinkedIn tools.
Stay fearless, friends.