Turning whispers into standards

The things you most want (and don't want) in teammates are the hardest to name. Turn gut feelings into criteria you can actually interview for.

Turning whispers into standards

Some people love to complain. They love to complain about how the fridge is running low on La Croix. They love to complain about the decisions management makes. They love to complain about the quality of the sales leads. Labor complains about and to management, and then management complains about labor. The story of human organization is complaints all the way down.

As a founder in my early twenties, I fielded a lot of complaints and was the source of plenty myself. It all felt gross. Every time I tried to talk about the dynamic, I felt like I was some fat-cat capitalist from a cartoon in a three-piece suit and monocle, smoking a cigar whining about the workers.

My chief complaint, at the time, was that we fired too many people. I kept a spreadsheet, and our hit rate sucked. We spent all this money interviewing, onboarding, and evaluating people only to let them go. Worst of all, we didn’t get to the bottom of why. I did notice a theme: the people we regretted hiring were big complainers. Maybe we didn’t need these complainers, I thought.

My coach told me, “complaints are gifts.” Tear open the wrapping paper reading “You Suck” instead of “Merry Christmas,” and you will, unfortunately, find valuable information about problems at your company. Maybe we do need those complainers, I thought.

Some complaints were legitimate. Our sales leads had issues, and that needed fixing. But the lack of La Croix from 1:15pm to 1:31pm was not the reason we weren’t hitting our numbers. Our problem was that we had too many people willing to lob complaint grenades about what didn’t work, and they thought that absolved them of the responsibility to figure out how to solve the damned problem.

And my problem was that I didn’t know how to say that.

Every founder, leader, manager holds fuzzy preferences like this one. Fuzziness is a limbo state where we know in our gut there’s something worth arguing about or fighting for, but we don’t know what it is well enough to describe it to ourselves, let alone others. If we can’t talk about it, we can’t filter for it, interview for it, or teach it. Great teams are great because they’re on the same page. And that page needs clear words, not fuzzy ones.

Mastery here ends with a team capable of filtering candidates without you present to make every tiny judgment call. To get there, you’ll follow three steps, over and over: notice it, interpret it, and systematize it. Notice the things that whisper. Interpret them until you can name the underlying preference. And then systematize it: integrate the named preference into your work and life. Write it down, teach it, train it. And test for it in interviews and performance reviews for both candidates and the team you already have.

Notice it

“Do you have a minute?” You hear that a dozen times a day. Life as a startup founder or executive is an assault on the senses. Your team contacts you via email, Slack, text message, phone call, knocks on the door, and taps on the shoulder. Stuff is always happening, and a lot of it is not good. The sales gong rings seconds before you find out one of your largest customers is about to churn. In back-to-back one-on-ones, you give one person a raise and deliver harsh feedback in the next.

In the middle of all of this chaos, something happens. You’re walking to a conference room for an interview. You overhear an executive berating a junior in front of their peers. In an ideal world, you’d think with perfect clarity, “Have we really created a culture where punching down is okay?” But you don’t. You just scrunch your face up and think “Gross,” and start the interview.

There’s a quote from Steven Spielberg I love to cite:

“The hardest thing to listen to, your instincts, your human personal intuition, always whispers. It never shouts.” [1]

In that moment, your intuition whispered. Something happened, you perceived it. But you didn’t have the time to process it, which means you’ll probably forget about it. The thing is, you don’t need to process it. Before you walk into that interview, pull out your phone and scrawl one line into a note I call the Whisper List: “Didn’t like how Roadrunner treated Coyote in the hallway (date).” Then go run the interview with the whisper recorded.

Interpret it

A week later, you get into the office early. Miraculously, there’s an empty hour on your calendar. You open up your Whisper List. “Didn’t like how Roadrunner treated Coyote (Tue Feb 17)” sits at the top, right above “Bugs ran the smoothest pipeline review in months. Why? (Thu Feb 12)” Five days apart, one unpleasant and one pleasant—both real signals. Neither tells you anything yet. A feeling is data, not a diagnosis. Think of your whisper as a fuzzy image under a microscope. Most whispers come into focus after a turn or two. Others require more work. At the end, when you finally see what you’re looking at, you’ll be able to name it. Getting the image into focus takes three turns of the knobs — your emotions, the stories your mind drafts, and deliberate inquiry. Only then is it worth trying to name what you are looking at.

Affect & emotion

You may have heard the phrase, “sit with your emotions.” If you’re anything like me, that phrase has left you day dreaming of throwing whoever said it out the window. Sitting is a passive word, expecting insight to materialize out of thin air. Instead, think of emotion as something you can actively investigate and learn from.

So how does that work? The first thing that happens after something happens, is that we feel one of two ways: pleasant or unpleasant. This simple binary is one axis of what psychologists call affect, and it sits upstream of emotion. The figure below shows the second. Clinical psychologists Jenna LeJeune and Jason Luoma call these appetitives, things you are hungry for, and aversives, things you want to push away or gag at. [2]

Most lists of whispers come back wholly unpleasant at first. Bad news hits harder than good news because noticing danger is what keeps us alive, on the savannah or at the negotiating table. [3] But if you only play defense, the behaviors you want more of go unnamed, unpraised, and unrepeated.

Figure 1: The Affective Circumplex
unpleasantpleasantactivatedidleexcitementangerpanicdisgustsadnessboredomfatiguecalm
The figure, with its two axes and ring, is Lisa Feldman Barrett's (How Emotions Are Made, 2017, p. 74), which she draws after James A. Russell's circumplex model (A Circumplex Model of Affect, 1980). The emotions are Management Craft's addition, placed as rough estimates for illustration: each sits at the angle Russell's subjects gave the word where he scaled it (panic and disgust are our guesses), runs from its mild form near the center to its intense form at the rim, is sized to our sense of how wide the feeling ranges, and is colored by its emotion family.

Lisa Feldman Barrett is one of the pre-eminent thinkers and researchers on the subject of affect and emotion. My interpretation of her research is that your emotions are weather patterns that sit atop affect. Like a thunderstorm forms when warm, moist air rises into the atmosphere and cools, anger often forms when your brain prepares your body to protect itself from a threat. Each emotion forms, rolls in, and so too eventually passes.

Your mind constructs each emotion based on your past as a prediction, preparing you for what it thinks will come next. [4] She writes, “Emotions are meaning… a prescription for action.” [4] Remember our executive berating a junior from earlier? Overhearing it, you got angry. The question isn’t “what does this anger mean?” It’s “what is this anger arriving to help me protect?

Your emotions shape your reality. People rate their whole lives better on sunny days. [4] Judges are more likely to deny requests for parole just before lunch. [4] And interviewers rate job applicants more negatively on rainy days. [4]

Our ability to feel and name our emotions beyond high-level categories like “happy” or “sad” shapes our behavior. People with finer-grained emotional vocabularies seem to be able to curb anti-social behavior like excessive drinking or retaliating aggressively against someone who hurt them. [4]

Figure 2: The Feeling Wheel
MadHurtHostileAngryRageHatefulCriticalJealousSelfishFrustratedFuriousIrritatedSkepticalScaredRejectedConfusedHelplessSubmissiveInsecureAnxiousBewilderedDiscouragedInsignificantWeakFoolishEmbarrassedJoyfulExcitedSexyEnergeticPlayfulCreativeAwareDaringFascinatingStimulatingAmusedExtravagantDelightfulPowerfulProudRespectedAppreciatedHopefulImportantFaithfulCheerfulSatisfiedValuableIntelligentWorthwhileConfidentPeacefulNurturingTrustingLovingIntimateThoughtfulContentThankfulSentimentalSereneResponsiveRelaxedPensiveSadSleepyBoredLonelyDepressedAshamedGuiltyApatheticInferiorInadequateMiserableStupidBashful
Gloria Willcox's Feeling Wheel (Transactional Analysis Journal, 1982, pp. 274–276): six emotional families. Click "The Hallway" for an example of what a CEO might feel in the case of the executive berating the junior, and note how you can feel multiple emotions at once.

Given that, when you’re dealing with a fuzzy preference, spend a few minutes naming the specific emotion you felt in that hallway. Naming it is not touchy feely woo woo hippie shit.

Associations & stories

Notice what just happened. Back in the hallway, you were dealing with an executive who berated a junior once. But after realizing how angry it made you, that executive became tyrannical. This executive, no matter how disrespectful, was not “One who seizes upon the sovereign power in a state without legal right; an absolute ruler; a usurper.” [5]

When the human mind does not have an answer for why something happened, it makes one up. [6] A hungry judge doesn’t think, “I lack information about this prisoner, and I’m so damned hungry.” Instead, they see a dangerous criminal and deny parole. We jump to conclusions with whatever evidence happens to be present and never notice what’s missing. [7]

And we’ve known this for a long time. Nearly two thousand years ago, the Greek philosopher Epictetus wrote:

“It isn’t the things themselves that disturb people, but the judgements that they form about them.” [8]

Thankfully, we can untangle the things and our views of the things. Conscious Leadership Group (CLG), in their book The 15 Commitments of Conscious Leadership, advises leaders to distinguish between facts and stories. [9] Picture this. You’re sitting at a conference room table. It’s 3:12pm. The only fact you have is that the counterparty was supposed to be here twelve minutes ago. That’s it. That’s the something that happened. As you wait and the clock ticks on, you begin to construct stories of what’s going on. “They don’t value my time” or “I’m sure there’s a good explanation.” But you don’t know whether they got in a car accident or drank too many vodka sodas at the conference hotel bar last night until more facts arrive.

To distinguish between facts and stories, CLG proposes that facts are “what a video camera would have recorded,” and “All stories are made up.” [9] While useful starting points, both are misleading oversimplifications.

What a camera can catch is behavior and observable events. An empty chair, a calendar event slated for 3:00pm, a clock sitting at twelve past. But not all facts are filmable. Off-screen, a man exhales vodka fumes in his hotel room because he’d decided that was preferable to telling his boss he’d blown the big deal.

What someone feels or believes may be inferred from behavior, but may also remain opaque either because they hide it, or because we simply miss it. People are on their best behavior in interviews; executives are especially skilled at talking even when they are less skilled at doing; sometimes that Nazi tattoo is covered up by a powder blue oxford.

All stories are constructed based on fact and inference and can be either true or false. Was the executive tyrannical? No. Did they berate a junior? Yes. Do they punch down? Maybe. One observed instance is often evidence of a pattern, but it’s also sometimes just a mistake. Depending on the severity of the thing, you may have all the evidence you need.

We can also hold untrue stories about ourselves that can interfere with our ability to accurately pin down a fuzzy preference, whether it’s during a hiring process or assessing an employee’s performance. At some point in your career as a leader, you’ll have to tell someone to get better at something. They’ll turn around and ask you how to do that. And you might not know how to teach them. Did you fail to provide a satisfying answer? Yes. Does that make you a bad manager? Not necessarily. Is there something worth uncovering under your feelings of frustration and helplessness? Absolutely.

Figure 3: Fact, Story, Internal Fact
FactStoryInternal fact
Carl has an accentCarl's not very smartI find it really hard to understand Carl in meetings
He asked how to get good at strategy; I had no answerI'm a bad managerI don't know how to teach this
The reference was glowingShe'll be great hereI let a trusted name override what I saw myself
He mentioned work-life balance onceHe isn't hungryI don't actually know what he meant; I haven't asked
We've talked to him four times and never made a decisionIf he were great, we'd have hired him by nowI haven't defined the job
I keep getting frustrated in our one-on-onesHe's not tryingI'm avoiding a decision I don't want to make
I haven't set up the systemI'm such an amateurI haven't made time for it
Each row starts with a fact, something a camera could catch. Then you interpret that fact with a first-draft story, and those stories are often incorrect. The facts in column three are internal facts, not visible to a camera. But more importantly, they're actionable.

Every story has one thing in common: a culprit. It might be a system, the other person, or you. “They don’t value my time” indicted them, and “I’m a bad manager” indicted you. If affect and emotion, associations and stories, are the first two focusing knobs on the microscope, the third is a triad of deliberate inquiry: systems, mutual, and self.

Three levels of inquiry

Whenever you can’t quite put your finger on something, whether it’s what was going on with the executive, reflecting on a bad hire, or defining hiring criteria, you can often find the root cause faster through three levels of inquiry: systems inquiry, mutual inquiry, and self-inquiry.

These three levels of inquiry come from the psychologist Ronald Short’s book Learning in Relationship [10], which I discovered when I first began coaching founders in the fall of 2020. Short’s book was on the (outstanding) reading list for the coaching certification program at the Hudson Institute of Coaching. It has been a workhorse for me as a coach ever since. And my clients tell me it’s something they always knew but never quite had words for. Equipped with the words, at last, they return to it over and over again.

Figure 4: The Three Levels of Inquiry
InquiryQuestionThe hallway case
Systems inquiryIs something about the system broken — the way it's designed?Have we built a culture where this is tolerated? Is he under too much pressure?
Mutual inquiryIs something broken between two people?Is there history between the exec and that junior — or between the exec and you?
Self-inquiryIs something going on just for you?Were you already fried from back-to-back one-on-ones? Is your history of conflict aversion influencing your reaction?
Ronald Short's three levels of inquiry (Learning in Relationship, 1998, p. 55): run all three in a few minutes when you can't quite put your finger on something — is it the system, the two people, or you?

In practice, you can run through all three in a few minutes. When something isn’t getting done well, or at all, ask yourself, “Who owns this?” If there isn’t a clear answer, you just found the root cause. Well-designed systems have clear structures of ownership. A project owned by three leaders is led by none. When two people insist the other one is the problem, ask yourself, “Have they sat down and talked about it, together, directly?” The answer is rarely yes. Not if they’re being honest.

And finally, you discover the compounding effect of a lack of self-inquiry. Your company lacks structure because you never built any. You never built any because structure means conflict, and you chose a paper-thin facade of safety over facing the argument boogeyman. An argument had is far preferable to an argument avoided; at least it has a chance of being resolved. And an avoided argument turns a self-awareness problem into a systems problem.

But that’s the beauty of the microscope. Use it to check all three levels, and you might just learn something that saves you and your company a shitload of pain.

Articulation

At some point, your fuzzy microscope image will come into focus, and you’ll need to give it a name. A great name is filmable — and it would be a shame to have worked so hard only to fail at naming. It evokes a concrete moment someone can picture themselves inside of. It gives us something to test for. “Praise in public; critique in private,” would be a fitting principle to arrive at for the executive berating the junior. Stripe uses “the front page test,” originally from Warren Buffett, as an operating principle for encouraging people to act ethically. [11] Ineffective names tend to label virtues, not behaviors. They are generic. Bad names are forgotten. Great names get used.

Systematize it

A named preference that never gets integrated into how you hire, review, and teach will not survive contact with the company. The CEO of a startup is like the captain of a ship. The ship needs a clear destination (vision, goals, plans, and so on), but in any given market many other ships and their swashbuckling crews will be racing to beat yours to the prize. What sets one captain, ship, and crew apart from another is how they decide to sail to their objective. To run a tight ship is to build a system, use that system, and improve upon that system when it falls short or when someone has an idea for how it could be improved.

While every fuzzy preference starts as a whisper, it must grow into a hypothesis and an experiment. “Praise in public; critique in private” is a theory of human organization: that a crew critiqued in private will beat one critiqued in public. If you decide to adopt “Praise in public; critique in private,” you’d better make sure the executive in question knows their behavior was unacceptable and knows where the line is between the next reprimand and a pink slip. Similarly, if a sales leader runs the smoothest pipeline review in months — the second line on that Whisper List, make sure they know it. Behavior is reinforced through consequences.

Arriving at a principle and giving feedback to someone who has violated that principle is a good start, but it’s not enough. You now need to install that principle into your company’s operating system. You need to know how to test for it. If it is a hiring principle, it is also a performance principle, and it needs to be written into your hiring and performance management processes. And once it is written into your process, you need to teach it. And teach it. And teach it again. You’ll know your team has begun to internalize it only when your team makes fun of you for how often you repeat yourself.

None of this is soft work. Andy Grove filed it under delegation:

“Beyond relaying facts, a manager must also communicate his objectives, priorities, and preferences… because only if the manager imparts these will his subordinates know how to make decisions themselves that will be acceptable to the manager… transmitting objectives and preferred approaches constitutes a key to successful delegation.” [12]

A preference you never made legible is a decision you have to keep making yourself, forever.

Whenever you translate a fuzzy preference into a legible principle, you’re likely to discover someone on your team doesn’t meet the new standard. Often they don’t meet it because they didn’t know it was there. Tell them, and that is the end of it. But that won’t always be the case, which is why you get paid the big bucks: to make hard decisions. A standard named but not reinforced is a standard in name only. Face the argument boogeyman, even if it means letting go of someone who can’t, or won’t, reach your standard to make room for someone who can and will.

As you build and improve your system, you will inevitably bump up against bias. Some forms of bias are repugnant and worth rooting out entirely. But sometimes what some will call a bias is merely a preference for characteristics linked to high performance. Typos and tardiness are accommodations best kept for therapists and elementary schools, not startups. It is okay to have preferences. It is not okay to have fuzzy ones.

At Management Craft, we chart each competency on an abridged version of the Dreyfus Model, a system developed in the 1980s to chart how humans develop skills. The original model has five rungs; for simplicity’s sake, each competency carries three: novice, competent, and expert. Use the rubric to self-assess, to calibrate as a team, or as a conversational aid when you’re teaching someone to run this loop themselves.

Figure 5: The Proficiency Rubric
Novice
  • Feels strong reactions to candidates and teammates. Either acts on them without thinking or dismisses them as good or bad "vibes."
  • Preferences surface only as post-hoc complaints — in the hallway, in the post-mortem, or never.
  • Interviews on unstructured gut feel, and hires people they don't enjoy working with without being able to say why.
  • Files every discomfort under "this is just hard" and pushes through.
Competent
  • Captures whispers when they happen — keeps a list in some form and actually returns to it.
  • Can usually trace a reaction to a specific, observable behavior and name the preference underneath.
  • Has written a handful of named standards into hiring questions or review criteria.
  • Tests a standard against the individual's evidence rather than the group's reputation — knows preference from prejudice.
  • Still needs the quiet hour (or a coach) to get from feeling to name; the loop runs in weeks.
Expert
  • Converts a felt signal into a named, testable expectation fast — sometimes in the same meeting where the whisper arrived.
  • Coins names that are filmable and memetic; the team quotes them unprompted and teases the leader for repeating them.
  • Hiring and performance processes carry the standards, and the team filters candidates without the leader in the room.
  • Runs the notice → interpret → systematize loop in both directions — reinforcing what goes right, not just naming what goes wrong — and renegotiates standards as the company changes.
Based on The Dreyfus Model of skill acquisition, six stages compressed here into three rungs.

In 2015, I stood in Seth Levine’s office in Boulder, Colorado. We’d arrived early for a board meeting, and while Brad, who sat on our board, made coffee, Seth and I ended up talking about something I’d been struggling to put into words: the complainers. I told him how I’d learned that complaints can be gifts, even if wrapped in mean wrapping paper. I knew any information, even if it’s just information about how people were unhappy, was useful. But how do we filter for, interview for, and select people who can persevere even when lots of stuff is broken? Seth responded immediately. “Oh, you’re talking about agency.” He told me how he’d developed a way to interview for agency over the years. You ask the candidate to tell you about a time they felt slighted or treated unfairly by a coworker or boss. Then you ask them what they did about it. Most candidates tell on themselves by blaming whoever they felt wronged by. Some situations people share are genuinely unfair, but many of them just sound like a four-year-old crying about the dog who took their toy. Except they’re forty and you’re interviewing them to run a multi-million-dollar P&L. What matters isn’t whether the situation was unfair or not. It’s how people react.

The best answer I ever got came from a guy who shared a quota with a teammate who went out on parental leave. He asked his boss whether his number would come down. The boss said no, so suddenly he had to hit double his usual number. I asked him what he did. He said, “I hit the fucking quota.”

It took about a year to arrive at the word “agency,” and longer still at a reliable way to filter and select for it. Some things take time to develop and name, but I often wonder what that year cost us. The good news: turning a fuzzy preference into something you can tell other people about, teach, and use is a skill you can learn.

To learn anything, you have to start small. You start with the 5 lb dumbbells, not the 50s. And you get better by practicing and training — getting your reps in. Here’s what to practice:

  1. Keeping a Whisper List: Figure out what medium works best for you, whether it’s paper, the Apple Notes app, or Notion. Thomas Jefferson literally took notes on a fan of ivory pieces he carried in his pockets, which he’d transfer to notebooks and then wipe clean to reuse. [13] The most important thing is that whatever method you choose, it should be quick and easy so you actually use it.
  2. Scheduling (and defending) time to reflect: Most founders’ calendars look like a game of Tetris. If you don’t block time on your calendar to explicitly think, you won’t do it at all. So block a recurring slot each week, even if it’s just an hour. And don’t let anyone schedule over it for any reason. During that hour, do whatever you need to do to eliminate distractions. Turn off Slack (it can wait), put your computer and your phone on “Do Not Disturb” mode, close the door (or go somewhere you won’t be interrupted), put on your headphones and listen to whatever music helps you think.
  3. Talking it through with someone else: Some people can reflect through journaling. Others would prefer medieval torture to writing about their thoughts. Both groups can benefit from talking to someone else to help them think something through. But know that not all help is equal. Talking about something you’re frustrated but confused about after three cocktails at the bar with your best friend will yield different results than working with an experienced executive coach. One benefit of hiring a coach, a therapist, or both is that it will force you to schedule time to reflect in the same way many people find working with a personal trainer is an effective tool to get to the gym regularly.
  4. Getting familiar with affect: Reflection and introspection, to many, can be an endless game of navel gazing. A minimalist approach, however, is just noticing and “coding” your reaction as unpleasant vs. pleasant. Unpleasant doesn’t always mean “bad.” But the same stimulus producing unpleasant affect again and again is information worth digging into.
  5. Observing behavior: “Shows up on time reliably,” “types on laptop in meetings,” “refuses to talk to customers,” “somehow delivers critical feedback in a way that feels good.” Each of these is a behavior, a thing someone does, that you can catch on a camera. They are facts stripped of meaning. Observe the behavior. Then pause before you layer meaning on top — “They’re on time because they don’t have kids.” That pause is where you catch yourself constructing a reality out of information that may or may not be true. Better to know why someone is consistently on time than to make something up.
  6. Making judgment calls: Leaders need to make decisions about strategy, planning, personnel, and so on. A decision is a judgment call: take the left path instead of the right. Keep this person, give them feedback, or fire them. Many of these decisions first show up as a whisper or a hunch. They do not show up at the door and knock, “Hey boss, I am a decision and here’s the options.” A hunch is to a decision as a seed is to a tree. But to make decisions, judgment calls, at all, you have to be comfortable making them. Amongst friends, nobody wants to be “judgy.” Our friends and family make decisions, many of them that aren’t any of our business no matter how much they confuse or annoy us. But as a founder or leader, the entire business is literally your business, and it is your job to make judgment calls and to develop good judgment. The funny thing is, even choosing not to judge someone’s behavior is a judgment call. Underperformers are underperforming for a reason, and the business is waiting for you to decide what to do about it.
  7. Keeping yourself honest: We all know the saying, “power corrupts and absolute power corrupts absolutely.” As a CEO or leader, you hold and wield the power to decide. You could decide with no information, bad information, or good information. Every decision you make is explicitly probabilistic. You are X% certain Y is the right call to make. But don’t confuse your certainty with odds in an absolute sense. I’m sure Bernie Madoff and Sam Bankman-Fried were quite certain they’d get away with it. They did not. Think of whispers and hunches like single digit certainties, and the entire process of interpretation is collecting evidence and separating fact from fiction.
  8. Flipping from negative to positive: People are very good at naming what we don’t like. So start there. “I don’t like how they blame everyone.” What would the positive version of that be? “I want people to take responsibility, especially when it’s inconvenient.” Think of negative articulations like the border of a dartboard. They define the boundaries of what is in and what’s out. A positive articulation is the bullseye. Write down both. The full target becomes: “Don’t blame others for your mistakes, take responsibility (especially when inconvenient), and don’t be afraid to call someone out when they skirt accountability.”
  9. Using your network: Other people often have the words you’ve been grasping for. Talk to other founders, executives, investors, or anyone who’s run a company or led a team before. Ask them if they’ve dealt with the type of thing you’re struggling to put into words. Yes, every company is different, but the tools and craft of organizing humans toward ambitious ends are much less so.
  10. Post-mortem mis-hires: Whether someone quit or you fired them, a departure is a rare moment of unequivocal feedback. Harvest it. Use it to learn and improve your processes. Was it your management style? Unclear expectations? Did you fail to create an MOC in the hiring process? Was there some unspoken cultural value that hadn’t been codified? Skipping post-mortems is flushing money down the toilet and choosing to torture yourself and your team for years to come. Don’t do that.
  11. Making your preferences legible: Even though you never read them, new products all come with user manuals on how to install, use, and maintain those products. It would be nice if people came with one of those, right? In her book, Scaling People, former Stripe COO Claire Hughes Johnson recommends creating a Personal User Manual, which she calls a “Working with Me” document: a short guide you write to help people you work with understand how to work best with you. [14] Many people are immediately averse to creating one of these because they think it’s self-centered. “Who am I to tell people to change to work with me?” Well, you’re the boss. You’re the CEO. You’re the leader of the team. If you don’t tell people how you like to work, you’re asking them to figure it out themselves. For real examples, check out neuroscientist, author, and entrepreneur Anne-Laure Le Cunff’s article on the subject. [15]
  12. Giving yourself permission to hire people you like (but not necessarily like you): Forcing yourself to hire people you don’t like, who don’t respect you, or who don’t want to work for you is a massive self-own and shockingly common amongst new founders and leaders. If you hate reading long-winded poorly-written emails, do not hire people who love to write them. Full stop. Don’t do it, man. Step away from that ledge. As Claire Vo puts it, you might just need to give yourself permission to say, “sorry homies this is how I roll and I’m king of the castle.” [16]

The most obvious way to fail at this competency is to simply not do anything in the section above. Beyond that, there are specific traps leaders fall into, and the vast majority of them are traps of deficiency — of doing too little of this work, not too much. They take the bait because the bait, good-sounding reasons, is appetizing. The costs compound, and the leader inside the trap is the last one to notice. As always, I turn to Aristotle’s Golden Mean when teaching failure modes, as every virtue lies in the center of an axis between two vices: one of deficiency and one of excess.

Figure 6: The Golden Mean
Under-doing
You feel the whispers but never name them; complaints stand in for standards. Your real hiring criteria live in your gut, where nobody — including you — can read them. Known misfits stay for years because acting on a preference feels like prejudice.
Just right
Standards are named, written down, and taught until the team teases you for repeating them. You hold the standard, forgive the slip, and act on the pattern — agreements get renegotiated, not silently broken. The team filters candidates and each other against the written standard without you in the room.
Over-doing
Every whisper triggers the full loop; reflection becomes a second job. Every slip is a firing offense, so people get good at hiding slips instead of fixing them. The named standards multiply into a rulebook nobody can hold — process as costume, not system.
Based on the Golden Mean, originally developed by Aristotle, named by Horace, and immortalized in fairy tales by Robert Southey.

Deficiency

The Achieving Superego

Remarkable achievement—whether it be in athletics, on Wall Street, or in Silicon Valley—takes tremendous amounts of hard work and sacrifice. It is not easy and it is often painful. In his book, The Hard Thing About Hard Things, Ben Horowitz has an entire section titled “The Struggle,” about the fundamental connection between entrepreneurship and adversity. [17] Your ability to tolerate pain is adaptive because it allows you to roll with the punches, which there will be many of. But it can also be misleading, disorienting, and maladaptive.

It is misleading because pain is so abundant we acclimate to it. As Nate Silver says, “There’s nothing like pain to build up your pain tolerance.” [18] Because you get used to the unpleasantness of challenge, at some point you’ll start thinking of it as an inevitability, something to just deal with. Steve Magness, who coaches Olympians and writes on the science of performance, puts it well:

“Pain isn’t something to fear or push our way through; it’s a message that needs interpretation.” [19]

It is disorienting because it often causes leaders to look at a situation they’re facing, like the disharmony between executives on their management team, and say, “This is just hard,” when, in fact, it doesn’t have to be that hard. Often, you have decisions and tools to reduce the unpleasantness of a given challenge, many of which turn out to lead to improved outcomes for the business, too. These decisions start with noticing the pain, move through a decision to quit something, and end with a decision to start doing things differently. You notice an executive refuses to send you the data you keep asking for, you decide to quit working with executives who can’t or won’t do what you ask of them, and you start interviewing for people willing to manage up to your standards.

It is maladaptive when you train yourself to stop seeing pain as a signal. When your superego, “the part of the self that congratulates us for doing our best and criticizes us when we fall short of our own standards,” tells you that pain is inevitable and it is a weakness to spend time listening to whispers, you will fail to address real and dangerous problems facing the company. [20] Yes, people can be difficult to work with. But the frustration a CEO feels when an executive refuses to provide them with information they need to make decisions is mission-critical information. Too high of a pain tolerance, though, and you’re not only deaf; you’re blind.

Believing Gut is Enough

Just because you’ve interviewed hundreds of people does not mean you know talent when you see it. The science of intuition shows us that our gut is a great noticer but an awful judge. Gut is like a notification system, but one that is hopelessly vague. Imagine your phone’s notification feed, but made up entirely of messages that read, “Something pleasant happened,” “Something unpleasant happened,” “You have received an email about something.”

Your intuition is only reliable in situations with quick and clear feedback. Think of the firefighter or chess players, not hiring managers. It will take a year for a new hire to accomplish their objectives, and nobody keeps a spreadsheet of how successful all the people they decided not to hire became. You may have interviewed hundreds of people. You don’t have enough structured data about them to call it feedback.

Psychologists Daniel Kahneman and Gary Klein disagreed on just about everything, but in 2009 they published a paper together titled Conditions for Intuitive Expertise: A Failure to Disagree. [21] In it, they conclude that intuitive expertise is indeed real, but you can only develop it if two things are true: an environment regular enough to actually learn from, and an adequate opportunity to practice with feedback. They then quote a list of professions that fail to meet these criteria. One of the professions? Personnel selectors, also known as hiring managers. [21]

So no, your gut is not enough. Gut is the beginning, not the end! It is a part, not the whole. You need to listen to your gut. Notice what it says. Interpret what it says. Name it and write it down. Underneath “something unpleasant happened,” you may discover an insight like “Praise in public; critique in private; especially when you’re a leader.” And that’s something you can teach your team, test candidates against, and hold each other to.

Process Allergy

At a January 1983 retreat in Carmel, CA, Steve Jobs told his team, “It’s better to be a pirate than join the navy.” [22] Steve Capps went on to raise a skull and crossbones flag above the Macintosh building later that year. [22] Today, founders still rally around the idea that they’re rebels, pirates, or disruptors challenging incumbent orthodoxy for both market share and cultural cachet. But the pirates of history were startlingly process-heavy organizations. Ironic, then, how terrified startups act when anyone suggests, not the black spot, but process.

We imagine pirates valued only one thing more than freedom, and that was gold, which was really just a means toward freedom. To get either, the pirates knew they had to follow orders. Every man agreed to a contract—signed and sworn—complete with pay, workers’ compensation (yes, really), a code of conduct, and voting rights. [23] And the quartermaster enforced that contract, and if you violated it they’d simply leave you in the middle of nowhere. [23]

Today’s startups, when they embrace the jolly roger, are all bark and no bite. They are cosplaying their historical peers, failing to adopt things like—gasp—writing things down and strict standards for who to hire and who to fire.

History’s pirates didn’t fail to deliver on their vision for a society of liberated libertines for their lack of process. They failed because their process was so goddamned good they robbed a bunch of powerful people so completely blind in a generational run at larceny that required a royal navy to put it down. Huh.

What founders fear is fuzzy. They know exactly what they don’t want to become: a big, slow-moving, bureaucracy complete with suits from Men’s Wearhouse and McKinseyspeak. But they don’t have a word for the thing they do want to be. This may be because there is not a noun in the English language for a company that runs on written standards without being a bureaucracy. It’s tough to aim at something without a name.

Former Stripe COO Claire Hughes Johnson, in her book Scaling People, wrote, “A good process should subtract from the number of meetings, not add more.” [14] A well-run company, a tight ship, then, is neither process-free nor process-choked, but a “just right” amount.

Confusing Preference for Prejudice

Bias is real. But not all bias is bad. From hungry judges to mean bosses and cigar-smoking fat-cat capitalists, everyone who ever discriminated believed their gut was fair. So what will make your decisions different? What is the difference between preference and prejudice?

What will make your decisions different is simple: writing them down. Prejudice thrives in ambiguity. When interviewers hire on unstructured gut feel, researchers find that “fit” reliably translates to people like me. [24] The interviewers, convinced they’re judging on merit, are doing no such thing. A written standard, on the other hand, is public, arguable, and testable — exactly what the research on hiring bias prescribes. [25]

Bad bias is prejudice: the act of pre-judging an individual based on stories you hold to be true—true or not—about a group before and instead of evaluating the individual on the basis of evidence. Salespeople talk too much, consultants love 2x2s, and ex-Googlers will be obsessed with process and perks. But even when a stereotype is true-ish, it’s still a very blunt instrument compared to actually gathering data about the person you’re interviewing.

As for preference, to hire is to prefer. There’s nothing wrong with preferring concise communicators, or people who show up on time to those who don’t. Preferences describe individuals’ observable behavior, linked to performance.

New leaders—founders or not—all spend years hiring people they don’t work well with because they’re unclear on their preferences. And what separates the ones who build great teams from those who don’t is learning what kind of people they work well with and devoting themselves to finding more of those types of people. Strangely, these people are more intolerant, not more tolerant. But they’re intolerant about the right things.

Excess

Overthinking Every Feeling

If you notice, interpret, and systematize every single whisper, you’re more likely to end up at a Buddhist monastery than ring the bell on the stock market floor. Self-awareness is not an end in and of itself, but a means to building a successful business. Using a Whisper List for capture is free; processing it takes time, and a startup leader’s time is scarce.

Executive coach Ed Batista writes about triage as the skill productivity systems miss. [26] Think of your Whisper List like the waiting room of an emergency room. Everyone there needs attention, but only the most critical cases get brought back to see the doctors. So how do you triage your Whisper List? You have two tools at your disposal: salience and recurrence. Gauge salience by looking at your list and work the one that stands out, feels more important somehow. It’s a whisper about a whisper. Recurrence is simple: if it shows up more than once, often after you’ve forgotten you wrote it down the first time, it needs your attention.

Punishing Every Slip

Once a whisper has become a noticed, named, taught, and systematized standard, what happens when someone violates it? And they will, because people are people, and people are imperfect. Even the most concise communicators ramble sometimes and the most punctual among us are occasionally late.

Some things are one-strike—ethics, dishonesty, sexual harassment—and for those things zero tolerance is entirely appropriate. As Marc Andreessen puts it:

“Priests, rabbis, and ministers should give people a second chance on ethics — not hiring managers at startups.” [27]

But if you treat slip-ups on more benign standards like timeliness as fireable offenses, you’ll drive out great people and people will just get good at hiding things from you.

Conscious Leadership Group, in their book The 15 Commitments of Conscious Leadership, observe that even leaders who are “impeccable” about their agreements to others only keep about 90% of them. And for the other 10%, they renegotiate the minute they know they’ll miss and take responsibility for missing. [9] So someone who’s late one in ten times but tells you before the meeting starts? Fine. But if they’re late half the time and don’t own up to it, show them the exit. They’ve already taken it.

There are so many things I didn’t know how to say as a young entrepreneur in my early twenties that I now have the words for. As I approach forty, I’m sure there are still more I’ve yet to find. What I can be sure I have found, however, is a method for finding those words, a microscope for turning fuzzy feelings into usable principles. And it goes like this. Notice the whispers and write them down. Interpret them — make regular time, and work until you can name what you found. Then systematize the name: teach it, test for it, and hold people to it.

1
Steven Spielberg, interview by Alice Winkler, What It Takes, Academy of Achievement, December 2017 (transcript, VOA Learning English, January 26, 2018).
https://learningenglish.voanews.com/a/what-it-takes-coach-steven-spielberg/4155025.html
2
Jenna LeJeune and Jason B. Luoma, Values in Therapy: A Clinician’s Guide to Helping Clients Explore Values, Increase Psychological Flexibility, and Live a More Meaningful Life, New Harbinger, 2019, 16-18.
https://www.newharbinger.com/9781684033225/values-in-therapy/
3
Roy F. Baumeister, Ellen Bratslavsky, Catrin Finkenauer, and Kathleen D. Vohs, “Bad Is Stronger Than Good,” Review of General Psychology 5, no. 4 (2001): 323-370.
https://doi.org/10.1037/1089-2680.5.4.323
4
Lisa Feldman Barrett, How Emotions Are Made: The Secret Life of the Brain, Houghton Mifflin Harcourt, 2017, 31, 74-75, 126, 182-183.
https://lisafeldmanbarrett.com/books/how-emotions-are-made/
5
“tyrant, n.,” sense 1, Oxford English Dictionary, Oxford University Press, accessed August 21, 2026.
https://www.oed.com/dictionary/tyrant_n?tab=meaning_and_use
6
Richard E. Nisbett and Timothy DeCamp Wilson, “Telling More Than We Can Know: Verbal Reports on Mental Processes,” Psychological Review 84, no. 3 (1977): 231-259, at 233.
https://doi.org/10.1037/0033-295X.84.3.231
7
Daniel Kahneman, Thinking, Fast and Slow, Farrar, Straus and Giroux, 2011, ch. 7, “A Machine for Jumping to Conclusions.”
https://us.macmillan.com/books/9780374533557/thinkingfastandslow
8
Epictetus, Discourses, Fragments, Handbook, trans. Robin Hard, Oxford University Press, 2014, Handbook 5, 288.
https://global.oup.com/academic/product/discourses-fragments-handbook-9780199595181
9
Jim Dethmer, Diana Chapman, and Kaley Klemp, The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success, Conscious Leadership Group, 2015, 143, 163.
https://conscious.is/resources#15commitments
10
Ronald R. Short, Learning in Relationship: Foundation for Personal and Professional Success, Learning in Action Technologies, 1998, 55.
https://www.learninginaction.com
11
Brie Wolfson, “From Kickoffs to Retros and Slack Channels: Stripe’s Documentation Best Practices,” interview by Brett Berson, In Depth, First Round Review, February 9, 2023.
https://review.firstround.com/podcast/from-kickoffs-to-retros-and-slack-channels-stripes-documentation-best-practices-with-brie-wolfson/
12
Andy Grove, High Output Management (New York: Vintage Books, 2015), 50, paperback.
https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884
13
Keith Houston, “Miscellany № 83: Thomas Jefferson’s Ivory Polyptych,” Shady Characters, November 2017.
https://shadycharacters.co.uk/2017/11/miscellany-83-jeffersons-ivory-polyptych/
14
Claire Hughes Johnson, Scaling People: Tactics for Management and Company Building, Stripe Press, 2022, 38, 108, 201.
https://press.stripe.com/scaling-people
15
Anne-Laure Le Cunff, “How to Foster Psychological Safety with a Personal User Manual,” Ness Labs, 2019.
https://nesslabs.com/personal-user-manual
16
Claire Vo (@clairevo), X, June 22, 2026.
https://x.com/clairevo/status/2069159292217995322
17
Ben Horowitz, The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers, Harper Business, 2014, ch. 4, “The Struggle.”
https://www.harpercollins.com/products/the-hard-thing-about-hard-things-ben-horowitz
18
Nate Silver, On the Edge: The Art of Risking Everything, Penguin Press, 2024.
https://www.penguinrandomhouse.com/books/529280/on-the-edge-by-nate-silver/
19
Steve Magness, Do Hard Things: Why We Get Resilience Wrong and the Surprising Science of Real Toughness, HarperOne, 2022, 124.
https://www.harpercollins.com/products/do-hard-things-steve-magness
20
Nancy McWilliams, Psychoanalytic Diagnosis: Understanding Personality Structure in the Clinical Process, 2nd ed., Guilford Press, 2011, ch. 2.
https://www.guilford.com/books/Psychoanalytic-Diagnosis/Nancy-McWilliams/9781609184940
21
Daniel Kahneman and Gary Klein, “Conditions for Intuitive Expertise: A Failure to Disagree,” American Psychologist 64, no. 6 (2009): 515-526.
https://doi.org/10.1037/a0016755
22
Andy Hertzfeld, “Pirate Flag,” Folklore.org, 2004.
https://www.folklore.org/Pirate_Flag.html
23
Charles Johnson, A General History of the Pyrates, T. Warner, 1724, ch. “Of Captain Bartho. Roberts” (Project Gutenberg #40580).
https://www.gutenberg.org/ebooks/40580
24
Lauren A. Rivera, “Hiring as Cultural Matching: The Case of Elite Professional Service Firms,” American Sociological Review 77, no. 6 (2012): 999-1022.
https://doi.org/10.1177/0003122412463213
25
Iris Bohnet, What Works: Gender Equality by Design, Belknap Press of Harvard University Press, 2016, 135-137.
https://www.hup.harvard.edu/books/9780674986565
26
Ed Batista, “The Most Productive People Know Who to Ignore,” edbatista.com, August 2014.
https://www.edbatista.com/2014/08/new-post-at-hbr-the-most-productive-people-know-who-to-ignore.html
27
Marc Andreessen, “How to Hire the Best People You’ve Ever Worked With,” pmarchive, 2007.
https://pmarchive.com/how_to_hire_the_best_people.html