A common pitfall in scaling organizations is the tendency to promote the best individual contributors to management. In many cases this results in a net negative exchange: you lose a highly productive teammate and gain a mediocre manager.

The underlying cause is that management is generally perceived as higher value, higher leverage, and more prestigious than individual contribution. You can change this perception by more rigorously defining the individual contributor career track, outlining pay grade and powers commensurate with the management track. But until you make individual contribution just as rewarding as management, gravity will keep pulling great teammates out of their wheelhouse.

The skills required to manage are not just unrelated to what makes individual contributors stand out, they may even be inversely correlated. I've joked that you should promote your best engineer to VP of Sales and your best saleswoman to VP of Engineering. The joke is half serious: running a sales team is all about building, measuring, and tinkering with single responsibility modules, while running an engineering team is all about managing high-value relationships and negotiating between stakeholders. The point is that what makes someone a good engineer does not necessarily make them a good engineering manager, and the same is true for sales.

The Technocrat is a manager who thrives on rolling up their sleeves and doing tactical work alongside their employees.

When an individual contributor works their way to the management track, they often become The Technocrat.

The Good Tendencies

The Technocrat is never out of touch. They never ask their team "Can't you just..." followed by some unthinkably impractical tactic, to frustrated eye-rolls and a diplomatic explanation of why that's not a good idea. They are respected by their team, because the team knows they could solve any tactical problem themselves.

The Technocrat is not too high and mighty to roll up their sleeves. They aren't afraid to get their hands dirty. They don't see themselves as occupying a different caste. That doesn't mean they're necessarily humble, but they don't perceive tactical work as below them. This keeps them grounded with their team, which inspires camaraderie.

By staying abreast of the relevant day-to-day tactics, the Technocrat can coach their team (especially recent hires) in a hands-on, impactful way. If they actually master the elusive hybrid - an ability to manage both the human (guiding careers, resolving interpersonal issues, etc) and the work (overcoming tactical challenges) - they will find a synergy of sorts. The ideal solution to a tactical challenge is sometime informed by a higher-level understanding of the employee trying to solve it. You can imagine a Technocrat manager saying:

In your career, one of the things you need to work on is balancing your idealism with some day-to-day pragmatism. On this specific tactical challenge, you're letting your idealist blinders obscure a simpler solution that will get us 80% of the way there with 20% of the work.

By merging career coaching and tactical problem solving, the Technocrat can be better at both. They can reinforce abstract high-level feedback with concrete, on-the-ground examples. And they can bring contextual, human psychology evidence to daily problem-solving.

The Mediocre Tendencies

The Technocrat puts implementation on a pedestal. They believe that the application of a strategy, where the rubber meets the road, is paramount. They're not entirely wrong. Execution is what differentiates an idea from a real business. But their thinking is too rigid. The Technocrat tends to be an implementation perfectionist, which leads to a dangerous mindset: "I could do it better".

This is the fatal flaw of the Technocrat. The "I could do it better" mindset has at least 3 significant shortcomings:

• It doesn't scale
• It doesn't empower
• It's arbitrary and premature

It Doesn't Scale

Obviously, one person cannot do all the work. At some point you have to trust other members of your team to handle the day-to-day operations. Scaling an organization is a never-ending process of making yourself obsolete. By automating or delegating each of your responsibilities, you free yourself up to focus on the bigger picture: new product lines, scaling company culture, painting the vision. You'll expand the scope of your organization by expanding the scope of your part in it.

It Doesn't Empower

In layman's terms, the Technocrat is a micro-manager. They just can't help but stay in the weeds. One of the best ways to learn is by making mistakes. But the Technocrat shelters their team from mistakes by dictating implementation details. Not only does that stifle learning, it alienates the very employees you want to inspire. The best employees are self-driven autodidacts with a passion for learning and experience. They will not thrive in an environment where everything has already been learned and experienced for them.

It's Arbitrary and Premature

The assertion that you know best, because you've "already seen the movie", is based on a hidden assumption that the setting hasn't changed. The reality is that, especially in new businesses, every day brings new challenges. And just because you've solved an analogous problem before, doesn't mean you fully understand the context and nuance of today's obstacle.

The "I could do it better" mindset not only assumes that experience trumps intuition or novel perspectives, it also assumes that perfection is paramount, that doing it better really matters. In reality, if your team is any good, they'll do it at least 80% as well as you would, and the final 20% probably doesn't matter (yet). It's more important that the work gets done, quickly, and then validated. Maybe down the road you'll help shepherd the work to perfection, but with new initiatives, perfect is the enemy of the good. Let your team get something good out the door on their own, and decide later whether it deserves the perfection of your Technocratic touch.

Are you a Technocrat?

The Technocrat is impulsive. They do not choose to meddle in the day-to-day, they can't help themselves. This is often the result of deep-seated control issues.

If you thrive on work and have other compulsive tendencies, especially a need to control your environment and outcomes, you may be a Technocrat. If your happy place is putting on headphones and cranking out some work, you may be a Technocrat.

One common perspective of the Technocrat is the categorization of management as "not real work". If, after a long day of one-on-ones, planning meetings, and communication, you lament the fact that you didn't have any time to do any "real work", you may be a Technocrat.

What to Do if You're a Technocrat

If you have control issues, explore them with a therapist. This blog ain't going to solve them for you!

Being in the weeds at work isn't necessarily a bad thing. Everything in moderation. One simple approach is to catch yourself anytime you volunteer a solution. Instead of "Why don't you solve the problem like this?" (which may look like a question, but sounds more like an order when coming from a manager), try: "Let me know if you want help tackling the problem. I'm sure you'll figure it out!" Start from a place of trust and delegation, and only intervene if disaster is imminent.

Try your best to avoid stepping in after the work is finished. Only do that if the consequences are truly catastrophic. A much better approach to team development is to let an employee make a mistake, wait for the consequences, then hold a blameless post-mortem. As a team, you can review the breakdown in process and implementation.

By preempting mistakes, you steal valuable learning opportunities from your team. But by taking your hands off the wheel and letting the team steer you into off-road terrain, you develop your team's navigation skills, and who knows, maybe they'll find another, perfectly-paved highway just outside your field of vision!

Still reading? Have you read the Chill Boss?

Cover Photo by John Schnobrich on Unsplash

Somewhere between a formal behavioral diagnostic and a Facebook "Which Disney Princess are you?" quiz, this is pop psychology and management drivel at its best.

But you should take it anyway. 😉

What is Mediocre Management? Start here.

Cover Photo by Evan Dennis on Unsplash

To lean on an over-used (and scientifically-debunked) metaphor: each business has a left and right brain. It is half science and half art, half quantitative and half qualitative, half corporate entity and half tribe of people.

One half can be boiled down to a set of metrics: cost per acquisition, customer lifetime value, revenue, gross margin, net income, and so on. Those metrics can be represented in spreadsheets, and it's easy to get lost in those spreadsheets. It's easy to fall into the misconception that a business is no more than the spreadsheets that record and project its metrics. It's easy to bury yourself so deep in the numbers that you lose sight of the other half of building a business: vision and culture.

Some might argue that you don't need vision or culture. That as long as you optimize for shareholder value, you'll build a great company. But teams are not motivated by shareholder value. Tribes do not rally around shareholder value. The metrics will indicate, in unequivocal terms, whether your business is thriving or flailing, but they won't inspire your team to solve the seemingly intractable, or to keep fighting when the odds are slimming. Peter Drucker said "Culture eats strategy for breakfast", but no spreadsheet can reflect your cultural values. Most importantly, spreadsheets aren't creative. They can't illuminate new paths or challenge your assumptions.

The Analyst forgets that a business is more than the sum of its metrics, and so they fall short of motivating, orienting, and retaining world-class talent.

The Good Tendencies

The Analyst tends to be risk-averse. They favor insight over impulse. Their team is not subject to the daily whims or whiplash of a chaotic agenda. Even if the ship is floating towards a waterfall, the Analyst will strive to calculate just how fast the river is flowing, and just how far the water will fall. Because to tack away from the waterfall or, god forbid, turn the ship around and head back upstream is a last resort the Analyst is loathe to propose.

The result is a culture of calm. Some workplaces are plagued by arbitrary prioritization: "the boss wants us to tackle this new project by Friday, so we'll have to work late tonight. Not sure why its so important all of the sudden, but let's get it done!" The Analyst rarely subjects her team to a last minute hustle. Every initiative has a clear strategic purpose and preordained timeline. The cadence of her team's work is steady - they do not "hurry up and wait". This engenders trust and calcifies strategy. The team understands how each project ties to the organization's goals, and respect for their Analyst leader is not eroded by a daily tide of cavalier objectives.

The other obvious benefit of charting a course thoughtfully is that the Analyst is likely to pick the right North Star, while a more impulsive leader might orient the team towards some other shiny object in the sky. There is nothing more powerful than a team, oriented towards a clear and dazzling North Star, marching through the night with no distractions on the horizon. Of course, the fundamental assumption here is that the Analyst has sufficient data (and data-processing capacity) to find the Star and set the strategy. That is not always a safe assumption.

Let's set aside the case in which a team's data-processing capacity is insufficient, as that is a tactical problem (hire a data scientist!). There's a meta strategic question that is often overlooked, especially by the Analyst: is there a decision point here, and can we make it with data?

The Analyst tends to assume that all critical decisions show up on their doorstep, complete with the necessary data. When you have a hammer, everything looks like a nail, and the Analyst's hammer is a spreadsheet. But sometimes the most critical decisions are not even on anyone's explicit agenda, and there is at least one category of decision that necessitates blind impulse, where analysis paralysis can be fatal. This is where the Analyst stumbles.

The Mediocre Tendencies

Imagine the landscape of solutions as a 3-dimensional space (in reality it's probably more dimensions than that, but I can't wrap my head around dimensions greater than 3, so let's stick with 3). There are lots of different sized hills, and maybe some mountains. The tallest of these is the best solution.

For example, if your company wants to fight physical pain, one of the tallest mountains will be Ibuprofen, another will be Acetaminophen, another will be Acupuncture, and there will be a little, tiny hill way off to the side that is Snake Oil.

If your team is climbing Snake Oil hill, the "local maximum" is the peak of Snake Oil hill: the very best Snake Oil solution on the market. The Analyst is great at leading their team to the peak of the hill that they are currently climbing, and finding the local maximum:

• They analyze the data: "All of our customers are saying this Snake Oil tastes like snakes!"
• They derive objectives: "Let's add some more sugar to make it taste less like snakes."
• They measure results: "Now the customers say it tastes like sugary snakes! Back to the drawing board."

Eventually, with diligent iteration, they'll find one of the local maxima.

The problem, of course, is you're still selling Snake Oil. Sometimes the best thing for your business is to hike down from the hill you're on, traverse the landscape of solutions, find a taller mountain, and start climbing that. That's finding the "global maximum", and it is where the Analyst falls short.

The Analyst has risk-aversion blinders that obscure this type of decision from their view, in part because it will rarely be presented to them by their team. "Should we throw away everything we know and start over?" is not a question asked often. The Analyst sometimes lacks the vision to see nearby mountains, and even if they conclude that the team might be hiking the wrong hill, they simply don't have enough data to make a data-driven decision. "How do we get down from here? We've only ever hiked upward! What do we do once we get to the bottom? Where is the tallest mountain?" Often there is no relevant data to answer these questions. When the leader does not have a map, sometimes the only thing to do is start hiking in a new direction. That is anathema to the Analyst.

It's rare to iterate your way to an inflection point. This is especially pertinent for businesses that have not yet found product-market fit. You have a solution on the market, but you don't yet have customers knocking down your door asking to give you money. Is it because you're still near the base of your hill, and as long as your team keeps hiking the customers will come? Or is it because you're hiking the wrong hill entirely, and missing the nearby mountain with the best view? The answer is rarely obvious or objective.

There are two phases to any problem-solving initiative. Frustratingly, they require the exact opposite perspective and skill-set. The first is throwing spaghetti at a wall: come up with as many potential solutions as you can ("No ideas are bad!") and throw them all at the wall. This phase requires creativity and an open mind to chaos. But as soon as one of the ideas sticks, the phase is finished. The second phase is doubling down on that solution and seeing it through. The second phase requires focus, discipline, and analysis. The most important analysis, of course, is determining when to toggle between the two phases. The Analyst thrives in the second phase, but sometimes misses a critical opportunity to revert back to phase one, and falters when faced with flying spaghetti.

Often the biggest risk is not taking enough risks, not turning back when a waterfall is on the horizon, or never hiking down from Snake Oil hill. The Analyst is uniquely susceptible to this paradoxical risk-aversion-risk, not only because they are risk-averse, but because the decision to turn around is often hard to justify with numbers alone. This is where art supersedes science. The leader must have conviction in their vision, and the cultural aptitude to inspire a team, even when no quantitative analysis can prove the new path is right.

Are you an Analyst?

The best Analysts have mastered self-analysis. So if you're an Analyst, you probably already know. You're risk-averse. You love crunching numbers. You're curious. You like talking things through and thinking critically.

The more important diagnostic is: "Are you on Snake Oil hill?"

The answer is deceptively simple: your team already knows. When you're hiking towards the global maximum, your team will highlight tactical, operational scaling challenges: "What do we do about all these support tickets? How are we going to build 60 widgets next month?"

But when you're hiking Snake Oil hill, the team will surface far more strategic questions: "How do we motivate customers to use our product? How do we stop Sales from selling something we can't deliver?" If you're an Analyst, your instinct might be to dive into these strategic questions and come up with strategic solutions. You might be inclined to architect ever more elaborate product packages and sales compensation plans, intended to corral customers and align internal resources. Fight that temptation. Instead ask yourself "Why is the team asking these questions?" If they are asking questions because you're scaling too fast then keep marching, you're onto something! But if they are asking questions because of fundamental misalignments, it's possible you're on Snake Oil hill, and the right answer is to a question that no one is asking: "Should we throw it all away and start over?"

What to Do if You're an Analyst

As with all the other Mediocre Management archetypes, it is critical to balance your mediocre tendencies by hiring a team that will challenge you. Don't build a team of Analysts, hire at least one crazy, impulsive person who will prod you to action. The Visionary is probably a good counterpart!

But you can also leverage your own strengths. You are organized and process-oriented. Build a lightweight process for impulsive thinking. Set aside a few hours every month to come up with questions you wouldn't dare ask out loud, and give them a little daylight. Ponder questions like: "What would our business look like if we threw away one product line? Are we systematically over-invested in one function of our business? If I had to let one member of the executive team go, what would the impact be?" These are tough questions that occur more naturally to an impulsive leader. You may come up with 5 of them each month, spend an hour on each, and decide to ignore all of them. That's okay. The mere exercise in stretching your impulsive thinking muscle is worth the effort, and may someday save your business when you find yourself halfway up the wrong hill.

Still reading? The Technocrat likes digging through the weeds just as much as the Analyst does.

Cover Photo by Nick Hillier on Unsplash

The line between friend and coworker can be blurry. In fact, defining "friend" and "coworker" as two discrete categories probably doesn't make sense in a modern, collaborative workplace.

The reality is that we spend more of our waking hours at work than we do at home, so if you don't count some of your coworkers as friends, you'll end up feeling lonely.

A company is made up of two distinct parts: a tribe of people with a shared culture, and a corporate entity with a charter, mission, revenues and costs.

When those two parts are aligned, everything is awesome. The Chill Boss is a good boss and there is no unresolved tension. When they become misaligned, when what is best for the culture is not best for the corporation, the results can be truly traumatic. There's nothing more painful in the professional world than friends laying each other off.

Good Tendencies

Chill Bosses make good cultural leaders. They are approachable, affable, and people like working for them.

In management they start from a place of trust, assuming that every employee is both competent and well-intentioned. Even with concrete evidence to the contrary, they hold tight to those assumptions. They do not micromanage.

The Chill Boss shines at company retreats and happy hours, and their employees often follow them from company to company because they build a comfort and rapport that makes work feel like play.

If the correct processes and resources are in place, and the team is set up for success, that loyalty drives results.

The Chill Boss is a people person, which lends itself to channeling the voice of the customer, defining target personas, crafting content that resonates, or envisioning features that address deep customer pain points. In short, their empathy is a valuable asset.

Mediocre Tendencies

There are two fundamental and conflicting narratives about employees (and people more generally). For the sake of simplicity, let's call them "People are Good" and "People are Bad".

The "People are Good" narrative suggests that if you give people resources, empower them with opportunity, and trust them with responsibility, they will rise to the occasion and wield their newfound privilege thoughtfully. This is roughly the narrative of the political left. It is the narrative of welfare checks and restorative justice. It is also the narrative of the Chill boss.

The "People are Bad" narrative contends that if you give people an inch, they'll take a mile. It is a narrative of winners and losers, where winners are revered for their hard work and skill, and losers are encouraged to pull themselves up by their bootstraps. This is the narrative of the political right, austerity measures, and likely the status quo in law-enforcement communities.

Unfortunately, the truth is not black or white. While I generally subscribe to the "People are Good" narrative, the reality is that there are people who will take advantage of opportunities without appreciating them. Almost more importantly, when a person does takes advantage of lenient and trustful leadership, that anecdote of abuse spreads quickly. In other words, the "welfare queen" story is remarkably galvanizing and destructive, regardless of whether it is a real phenomenon, quantitatively. People love to point a finger at the loopholes in a system, and the moochers who take advantage of them. Again, the evidence tends to be purely anecdotal, and sometimes the anecdotes themselves are more folklore than fact, but the stories have power nonetheless.

This hole in the "People are Good" narrative is one of the fundamental risks of being a Chill Boss. It plays out something like this: the Chill Boss gets rid of vacation tracking, because they trust their team to be responsible. Nine of the teammates are responsible, because they're mission-driven, they love their team, and they enjoy coming to work in the morning. But one member of the team (who probably shouldn't have been on the team in the first place) starts to take advantage of the loophole. First, it's just an extra day or two. But over time it adds up, and the team starts to notice. Before long there are snide jokes at happy hour, and not only does the team have contempt for their colleague, they've lost respect for their Chill Boss.

If we look at the underlying cause here, it is probably that this person shouldn't have been on the team in the first place. And this speaks to the biggest mistake that the Chill Boss makes: they tend not to fire people fast enough. They give everyone the benefit of the doubt, sometimes to the detriment of the team's performance.

Trust in your team should not be a liability. But you can only trust your team if your whole team is trustworthy. Frankly, most teams bigger than 10 probably aren't trustworthy unless they have been actively pruned to protect the trust. That is a hard balance to strike, as the act of pruning is obviously a delicate one, and can undermine trust in itself. But if there is someone on a team taking advantage of the Chill Boss, usually the team notices before the boss does, and the team appreciates it when the boss finally takes action.

Are you a Chill Boss?

Do you consider your employees to be your friends? Do you hang out with them outside work? Do they open up to you about their personal lives? Do you start from a place of trust?

None of these are bad things. If you said yes, you're probably well-liked. And that can mean that your team is loyal and driven to impress you. But when the going gets tough, you'll need to take conscious action to offset your Chill Boss tendencies.

What to Do If You're a Chill Boss

Ask your reports whether anyone is taking advantage of your leniency. You should explain to them that they can tell you in confidence, and that you trust them to tell you, instead of gossiping with their teammates.

When they open up, you should thank them for sharing, and then take the blame. It is your fault, after all, that there are loopholes in your organization.

Once a quarter, take a hard look in the mirror, and ask yourself whether there is anyone who is dragging the team down. You'll probably say "Bob is sort of slowing us down, but we're working on it. He's developing. He'll be better by next quarter."

More often than not, that rationalization is just a way to postpone the inevitable. One of the most painful truths is that turnaround stories are rare. If someone isn't working out right now, you should assume they never will. What's much more common are good teammates becoming great teammates, as their managers allocate more resources and support to good employees, and ensure the team maintains a high standard of performance.

The Chill Boss must acknowledge that people rarely change, and some people just aren't a good fit. Maybe they're not motivated by the work, or maybe they don't value communication, or maybe their set of skills doesn't exactly align with what the team needs right now. Whatever the reason, when a tough decision has to be made, the Chill Boss often freezes. That lack of decisive action can be as erosive to the cultural foundation as an Authoritarian cracking down.

Still reading? The opposite of the Chill Boss is the Authoritarian.

Cover Photo by Joseph Greve on Unsplash

Humans love stories about visionaries. More than one global spiritual movement has been built on the foundation of a story about a Visionary. In the corporate world, especially in technology and innovation, Steve Jobs is an almost religious icon.

Why are we obsessed with Visionaries?

We love visionaries because we can project superhuman powers on to them.

For those who are anxious about change, there's a comfort in knowing that someone is looking into the future and preparing for the changes to come. In an uncertain world, it's reassuring to believe in magical, benevolent forces shaping the future.

For those who embrace change, there's a natural tendency to project oneself into the role of visionary. It is exhilarating to think that a mere human can be elevated to visionary status by predicting the future and building for it. "What if I'm the next Steve Jobs!?" is an intoxicating thought that occurs to many a budding entrepreneur. And because most "overnight success" comes after a decade of toil, the "next Steve Jobs" and the next entrepreneurial failure are pretty much indistinguishable (until they're not).

The Good Tendencies

Effective visionaries tend to be excellent orators, and (at least publicly) very charismatic. They are surrounded by a Reality Distortion Field, a sort of bubble that follows them everywhere they go and casts a haze over the cold hard facts. They are magical thinkers, compelling speakers, and they are given the benefit of the doubt both in the moment, and in the revisionist history that follows their success. In retrospect, their luck, their mistakes, and their flaws are erased and only the vision and execution are remembered.

Visionaries are, by definition, not entirely rational. And we need them. A rational thinker would never build an innovative startup, because the math doesn't add up. A rational thinker would stick to their cushy job at Google making six figures. It requires a significant leap of faith, magical visionary thinking, to quit your job, take out a second mortgage, and start building in your garage.

In other words, the risks and sacrifices required to build something unprecedented require irrational thinking.

If irrational thinking isn't dumb, then it's visionary and magical. To quote Spinal Tap, "there's such a fine line between stupid and clever". Often the distinction between dumb and visionary is blurry until the market either validates the model, or the business fails!

The Mediocre Tendencies

While a bit of irrational thinking may be required to get a novel business model off the ground, there are ways in which the Visionary tends towards mediocrity.

Finance

Visionaries often treat their Sales Pipeline like it's Accounts Receivable. In other words, they take for granted that deals on the horizon will close, and they build their budgets with optimistic assumptions. They socialize these assumptions with their team, their investors, and their advisors. If you give them the benefit of the doubt, that's just inspirational leadership. In reality, it's probably more accurate to call it fraud (or at least reckless negligence).

The irony is that if the deals do close, history rewrites that fraud as a bold vision of the future. But deals often hinge on factors that are not within the team's control. So the difference between closing and not closing, vision and fraud, often boils down to little more than luck.

Product

The "Vision" in Visionary usually refers to a product vision. It's rare that Visionaries pride themselves on their ability to build an innovative go-to-market strategy or financial model. They tend to believe that their vision for the product has intrinsic value.

It doesn't. In fact, it's probably a liability.

For starters, a product vision is arbitrary by definition. It is based on a data point of one: the Visionary's perception of a market's demand. If it was truly based on data, it wouldn't be called a vision.

When building a novel product, it is paramount to have an agile, experiment-driven mindset. Every assumption must be scrutinized. Every investment of time and capital must be warranted by data. Every challenge must be approached scientifically: What is our hypothesis? What are our assumptions? How can we test those hypotheses and assumptions efficiently and come to a statistically rigorous conclusion? Visionary thinking is antithetical to the scientific method.

So Visionaries tend to make arbitrary product decisions and they struggle to adopt a scientific mindset. But that problem is actually compounded by another mediocre tendency of Visionaries: they are often product perfectionists.

Reid Hoffman says "if you're not embarrassed by the first version of your product, you've launched too late." Many Visionaries have an emotional relationship to their product. The alignment of their product and their product vision is tied deeply to their sense of self. Any product short of the beautiful vision they hold is a personal embarrassment. This leads them to build arbitrary assumptions on the foundation of other arbitrary assumptions.

In other words, an arbitrary assumption isn't so bad if you get it into the hands of customers and validate it quickly. But if you are unwilling to put anything short of a finished product in front of a customer, you will inevitably layer arbitrary assumptions on top of other arbitrary assumptions, compounding the problem.

Lastly, the sheer volume of creative output from a Visionary can overwhelm a small team. When resources are limited, success requires focus. A Visionary may have 15 great ideas, but if they can't pick 1 to focus on, their vision gets lost in the chaos.

Most individuals can only effectively execute on one experiment at a time. There's a cognitive overhead in fully grasping a new project's scope. So if the Visionary can't filter their creative energy down and direct one tactical shift at a time, the team on the ground will find themselves playing an unproductive game of tactic whack-a-mole.

Are you a Visionary?

A little bit of a Visionary tendency can be healthy. Too much can kill your business.

Finance

A simple test: Can your CFO or CPA or COO recall a time when you implied to an investor, advisor, prospective hire, or colleague that a deal was closed, when in fact it wasn't? If so, was that recklessness? A one-off case of fraud? Or is there a systemic pattern of reckless bordering on fraudulent behavior?

If it's the latter, you probably shouldn't be the CEO.

Product

A simple test: Can your VP of Engineering or CTO communicate your vision in one sentence? Can they point to what their team is doing on the ground this week to further that vision? Have they shipped a feature this week? When they shipped that feature, was there instrumentation in place to measure the adoption and usage? Did anyone talk to any customers who used it?

If the answer to most of the above is "No," something is very wrong.

If the answer to some of the above is "No," something might be wrong.

If the answer to all of the above is "Yes," congrats! You don't have a product focus problem.

But if you do have a product focus problem, it's either because you're an unchecked Visionary, or because you have ineffective technical leadership.

Both are crippling.

What to do if you're a Visionary

Stay calm! It's not the end of the world. Either you can mitigate the mediocrity, or you can move into a role where the mediocre tendencies are less of a liability.

Mitigating the Mediocrity

On the finance front, there are all sorts of ways to offset your tendency to treat the sales pipeline as accounts receivable.

You can simply delegate: "Check with our CFO on that."

You can lock down data: "The sales pipeline is shared on a need to know basis, and I don't need to know!"

Or you can hedge all your financial proclamations: "I am an eternal optimist, it's how I drive this business forward, so I am confident we'll close $100k this quarter!"

Irrationality is the underlying trait that drives a Visionary to mediocrity. So find ways to stay grounded in reality. You can run all your numbers by the team pessimist. You can set a coefficient on all your projections to adjust for optimism. At one point, I was such an irrational engineering leader that our Director of Product had a 12x multiple he'd use to adjust my estimates. There are two valuable lessons there: the first is that humans are predictably irrational. The second is that finding a counterpart who complements your strengths and offsets your weaknesses can lead to a team that is greater than the sum of its parts.

The rational thinker can't build anything innovative without the Visionary, but the Visionary needs the rational thinker to stay grounded, focused, and honest.

On the product front and beyond I recommend Kanban, a dead-simple methodology for organizing initiatives. If you suffer any of the mediocre tendencies of the Visionary, set aside at least an hour a week to prioritize your ideas, and bring along a more rational counterpart to help.

You don't need anything more than a bunch of Post-It notes and a wall with 3 columns on it. The three columns are Backlog, In Progress, and Ready for Validation.

Your Backlog consists of ideas that aren't ready for prime time. Keep these ideas to yourself. They are a distraction for everyone else. You should keep the ideas in the Backlog prioritized, with the most important ideas at the top, but only move a Post-It from Backlog to In Progress if your team is ready to take on a new project.

The In Progress column consists of initiatives underway. Each should have a clear owner, and ideally be broken down into tiny chunks. Constantly ask yourself - is there a simpler version of this that we could get to market faster? Every time you check in with individual members of your team, check in on each Post-It that they own, and ask if there are any blockers preventing progress. Keep the list small. As a general rule, no one should own more than one Post-It at a time.

Ready for Validation is (hopefully) the final step. It indicates that an idea has gone to market but its value hasn't been proven. In a dream world, you can validate all your initiatives with quantitative data. In reality, as one of my (non-mediocre) bosses once said: "We use the North Star for guidance, but we don't expect to get there". In other words, you may not always be able to validate initiatives with statistical rigor. But you should try, and you shouldn't consider a project finished until you've validated it in some form. If you can't validate it - send it back to In Progress with a new, measurable objective!

If all of the above methods of mitigation fail, then it's time to look in the mirror and decide if your team needs a new leader.

Visionaries make great CPOs (where P stands for Product or People). Product and Culture are two of the most critical domains of the CEO, but they don't have to be owned solely by the Chief Executive. If you bring in a leader to oversee the organization, set priorities and make executive decisions, you may find yourself much happier, focused on manifesting your vision!

Still reading? The opposite of the Visionary is the Analyst.

My mother always says I should try working for a big company. Maybe someday I will, but I haven't yet. This series is about management and entrepreneurial failures at small companies. I've worked mostly at software tech startups, but I'm hoping the lessons here are a bit more universal than that.

65% of Americans say seeing their boss fired would make them happier than getting a raise. When I was younger I was skeptical of the need for bosses at all. I've since realized that most people hate their bosses because most bosses are mediocre.

In other words, holacracy (a framework that eradicates hierarchical management, applied by Zappos and others) is an earnest attempt to solve a real problem. But getting rid of management entirely would be throwing the baby out with the bath water. People need management. Good management relieves stress, heightens focus, encourages growth, aligns teams, and empowers talent. But in most cases people experience mediocre management, which may actually be worse than no management at all.

This series is about mediocrity, in the hopes that we can all spot instances of it in ourselves and rise above it.

I have made every mistake in this series. Most leaders have. So the chapter titles are misleading, because I've never met a person who fits neatly into any one of these boxes.

Each archetype has good and mediocre tendencies. Here they are in no particular order:

• The Chill Boss
• The Authoritarian
• The Visionary
• The Analyst
• The Technocrat

We all stumble in and out of these archetypes. Leadership failure happens in fleeting moments, it is not a state of being. But hopefully one or two of these archetypes will feel particularly familiar to you.

Step one is identifying your own mediocre tendencies.

Step two is offsetting them with a balanced team and a tool-set for self-awareness and regulation.

This series outlines that journey.

Ready to start? Take the quiz or read about the Chill Boss.

Anyone who has tried to manage by consensus knows that it's anything but efficient. For some organizations, that's okay. Not every organization optimizes for efficiency. Most worker-owned cooperatives optimize for other outcomes, like community-building and social impact. However, if you're optimizing for efficiency, the best leadership model is a benevolent dictatorship.

Automattic (the company behind Wordpress) is sometimes described as a benevolent dictatorship. The Ruby on Rails community is, too. Even if the dictator has a... big personality, they can still rule benevolently. But absolute power corrupts absolutely, and I'd bet that malevolent dictatorships outnumber their benevolent cousins.

To be clear - it's rare that malevolent dictators think of themselves as malevolent. They simply have fallen for the narrative that if you give people an inch they'll take a mile, and they follow that narrative to its logical extreme. To call it malevolence is a bit misleading. The mediocrity of these leaders emerges from intellectual laziness and ignorance, not evil intentions. They subscribe to a world-view that is fundamentally cynical. They allow that world-view to govern their actions as leaders, because the counter-evidence debunking their world-view presents cognitive dissonance (and they haven't put in the time to research group psychology and team performance).

Good Tendencies

A benevolent dictator polls the team, truly listens to every relevant voice, and then takes decisive action. Decisive action doesn't necessarily mean making a decision. It might mean delegating the decision-making authority to one member of the team. In an effective dictatorship, there is no waffling. Sometimes the dictator makes the wrong decision, but they never fail to outline decisive action items and next steps. This focus and velocity is galvanizing. Teams led by benevolent dictators often move faster, work harder, and rally more cohesively than their more democratic competitors.

One tangent about "listening to every relevant voice" - teams often make the mistake of favoring their loudest voices. Introverts have a fundamentally different approach to decision-making. They do not let impulse drive their contributions. They mull problems over before coming to solutions. As a result, their solutions are often more comprehensive and thoughtful than those of their extroverted counterparts.

An effective leader can elicit feedback and guidance from both the introverts and the extroverts on their team. This may mean slowing the decision-making process down by a day or two. After presenting a problem, you should ask your team to follow up with an email outlining their proposed solutions. If you present a problem, collect potential solutions, and pick one, all in a single meeting, you will almost inevitably favor the extroverts. That is biased, counter-productive data collection, and it's profoundly demoralizing to the introverts on your team.

If an Authoritarian listens carefully to their team and considers every perspective before making a decision, they're not really an Authoritarian. So admittedly, I'm stretching a bit to come up with the Good Tendencies of an Authoritarian. But there are some environments where Authoritarianism is the only way. There is no time for consensus-building in a military context where efficiency of decision-making has life-and-death consequences.

Similarly, if there is a sufficiently wide experience or skill gap between leadership and the team, such that leadership has nothing to learn from their employees, presumably Authoritarian rule makes sense. The closest you'll get to this in a technology business is a Sales boiler room where inexperienced reps are dialing for dollars, or a data entry warehouse where tightly-packed contractors are grinding on borderline-automatable tasks. I would argue that the existence of either one of those rooms speaks to a deep, strategic flaw in the organization's structure. But that's a conversation for another day!

The Mediocre Tendencies

By 2020 half of the workforce will be made up of Millennials. Every recent study of workplace dynamics describes a generation that seeks intrinsic motivation, autonomy, freedom, and respect. The Authoritarian is a dinosaur that will be rendered extinct by this seismic shift. Evolve or die!

"Time in seat" is a common battlefield for clashes between the Authoritarian and their team. The Authoritarian believes that enforcing a strict 9-5pm policy will drive productivity. The team does not agree. They feel micromanaged. The mistrust is palpable. The team is distracted. They gripe with their colleagues about how out-of-touch management is, furthering the organizational divide and shutting down vertical communication channels.

The rigid policy leads to stress at home. Spouses ask "Who is going to pick up the kids from school?". Employees carry that stress to work. They text their spouses frantically. "The boss is in town today, can you sneak out to pick up groceries for dinner?". The bravest (and the highest-value) team members start circulating their resumes. Obviously, the Authoritarian's approach did not lead to increased productivity. It backfired.

Why does this happen? One underlying cause is that productivity is much harder to measure than "time in seat". So Authoritarians just assume that "time in seat" is a valid proxy for productivity, but they lack the intellectual rigor to test that assumption. Productivity is subjective, and even when it can be quantified, it tends to be inconsistent, varying dramatically from quarter to quarter, employee to employee.

The closest most organizations get to effective productivity tracking is when they establish a sales quota. But even sales performance tends to be spiky and unpredictable. If you're a sales leader who has implemented a strict "time in seat" policy, reigning in a more lax culture, and seen a resulting improvement in productivity, please reach out with the data! I have never seen a statistically significant correlation between "time in seat" and performance. I have seen an inverse correlation.

Another underlying cause, discussed in The Chill Boss, is that the anecdote of a moocher taking advantage of lax policies is a very galvanizing narrative. Pendulums always swing, and we should not be surprised by the impulse to enforce strict policies when one team member is taking advantage of a trusting culture. The benevolent dictator would simply fire that individual, but the more common response is reactionary: close the loophole. Not only does that reaction punish the people who earned and maintained the trust, it also does away with an effective "moocher trap". In other words, by starting from a place of trust, you can develop policies that readily surface employees who are not deserving of that trust. If you have the gall to part way with those employees, that can prove to be an efficient team-pruning mechanism.

While firing under-performers is a critical function of any leader, retaining high-performers is arguably even more important. There is a blind spot here that the Authoritarian often misses. Most business leaders are painfully aware of the cost of customer churn. Losing customers hurts revenue. Duh. But somehow, many business leaders fail to acknowledge the cost of employee churn. Every employee lost incurs significant costs. The cost to recruit, vet, and train a new employee is non-trivial. It is also fairly opaque: the cost tends to get muddled and buried amongst the other operating costs of the business. Very few small businesses are sophisticated enough to separate out the cost of employee churn in their financial modeling, but that doesn't make the cost any less real.

The best employees thrive when trusted with autonomy. Those employees will churn under an Authoritarian. Any costs saved by a strict "time in seat" policy are surely outweighed by the costs incurred when you lose your best people.

Are you an Authoritarian?

It all boils down to trust. Do you trust that your team will not take advantage of you? Or do you think that your role is to keep your team in line, because if you give them an inch, they'll take a mile? If you see your role as the rule enforcer, you're probably an Authoritarian.

What to Do if You're an Authoritarian

You may be spending a good bit of mental energy worrying about whether people are taking advantage of you, whether you need new rules, or if there are loopholes. Try to channel all of that energy into developing clear, quantitative, productivity measures. One of the primary functions of leadership is to set KPIs that are tactical (and tied intuitively to daily activity), but that roll up to the strategic goals of the organization. For a Customer Success Manager, a good example would be "% of Customers who Rate their On-boarding Call as Excellent". This probably rolls up to the strategic goal of customer conversion or retention, but it is far more tactical and actionable. It gives the employee a simple benchmark they can chase every day.

I promise that if you have clear goals like this in place, and good dashboards that track progress towards those goals, at both a team and an individual level, you will begin to realize that even though Jane came in a bit later than the rest of team last Tuesday, she's still killing it on her on-boarding calls. And even though Mark is in every day at 7am, he is not effectively communicating your feature set to new customers. These insights are far more critical than time in seat.

Lastly, spend time with your team. Ask them questions about their lives outside of work. Make an effort to get lunch with the introverted recent hire who hasn't quite fit in yet. You'll realize that the narrative of the moocher is self-fulfilling. If you treat your team like children who can't be trusted, they will act like children and try to find loopholes in your authority. But if you treat them like adults, and start from a place of trust, they will rise to meet you on your level.

Still reading? Sometimes Authoritarian traits dovetail with the Visionary.

Cover Photo by Igor Ovsyannykov on Unsplash

One of the most powerful concepts in computer science is "Layers of Abstraction."

At the lowest layer you have ones and zeros. At the highest layer you have the user interface. Every step between the binary and the user is a translation of sorts. At each translation, a piece of software becomes more human, and more specialized. When computer scientists talk about low-level versus high-level, they are not intending to betray a value judgment. Low-level programming languages are not lower in value, they are just more computer-y, and less human.

When software engineers talk about a "stack", the origin of that term is a reference to these layers of abstraction, stacked on top of one another.

You can take this concept and apply it at a company level.

Sales and marketing is the application of a product to a market. Product is the application of technology to a problem.

As a company, it is critical that you allocate resources only to the areas that truly differentiate you. Many companies end up investing in areas that support or enable their core value, without actually contributing to it. For example, if your product is the world's fastest motorcycle, you might make the mistake of building a race track. Sure, that race track will help you test your fast motorcycles, but it doesn't actually contribute to the speed of the motorcycle. You'd be better off outsourcing the race track to a race track manufacturer, so you can focus on your bike.

One question I ask companies is: on which level of this stack do you differentiate yourself? Are you fundamentally a technology company, a product company, or a sales company? To give some concrete examples:

Google is a technology company. Their core differentiator was a software algorithm that was 10x better than anything on the market. Yes, they layered on a pretty interface (to some extent), and a huge sales operation, but the foundation was technology.

Apple is a product company. They differentiate at the product level, meaning that their technology is actually not all the differentiated. They buy a lot of their hardware from other suppliers. Again, no value judgment here. They have operationalized exceptionally well and become the best in the world at the product level.

Salesforce is a sales company. The technology is basically a relational database, their product is a thin, moderately intuitive management layer on top of that database. But they sell the shit out of it. They could sell annual SaaS licenses to an an off-line emu farm (and they probably have).

The make up of your team, the culture of your company, and the KPIs to which you hold yourself accountable, should all be defined by the layer of abstraction at which you intend to differentiate.

KPIs

If you are a technology company, that usually means you're building something novel that can do things faster, cheaper, or more automated than the status quo. Your KPIs should be rigorous technical benchmarks, holding yourself accountable to a 10x multiple. For the first few years of your company, you may achieve no sales or market validation at all, and that might be just fine, because you're optimizing and investing in technology that will effectively sell itself (just kidding - you'll still need a sales team).

If you optimize at the product level, you generally won't have enterprise sales opportunities. Enterprise sales requires either fundamentally valuable technology, or an organization that is perfectly optimized around sales. In other words, enterprise sales works well for companies that optimize at the lowest and highest levels of abstraction.

Instead, companies that optimize for product tend to go after the long tail of customers. In acronym speak, that means B2C or SMB (low-touch) B2B. That means that they need strong referral growth mechanisms, which requires optimizing for NPS score, retention rate, and blended CAC. These companies tend to be the sexiest, and the most elusive. Anyone who says "We're like X, but we don't suck", or "We're like Y, but more intuitive" is optimizing at the product level. There tends to be an "if you build it they will come" mentality on teams that optimize at the product level. That's a dangerous fallacy.

Companies that optimize at the sales level tend to move upstream quickly, going after enterprise contracts. Their UX doesn't have to be revolutionary or even intuitive, their tech doesn't have to be 10x faster. Often the buyer to which they're selling is not the eventual user of the product, so the success of the deal has more to do with the nature of the relationship, and the internal politics and processes of the company that's buying. The KPIs most predictive of growth are average deal size and time to close. If you're closing big deals quickly, not much else matters!

Team

Just as your KPIs should be defined by where in the stack you differentiate, the makeup of your early team should also be optimized.

If you're optimizing for technology, you need Ph.D.-types or engineers with deep domain expertise. At least one of the founders should have years of experience and a deep understanding of the current state of technology. Early on, the company will effectively be led by the VPE or CTO, as the CEO secures funding and keeps current investors at bay ("we're building something big here, but it's going to take time").

At some point, you'll have to take your technology company to market. Occasionally, technology-focused companies fail because they never actually build technology that's 10x better than the status quo, but I'd bet the more common cause of death is that the founders get frustrated because the world doesn't immediately understand just how revolutionary their technology is, and they give up. The solution is to build a sales team that is technical enough to understand why the value proposition is so powerful. Ideally your sales folks are former engineers, or at least have deep experience selling technical products and studying technical subjects. Build your sales team earlier than you think you need it, and if they're ready to sell before the tech is, incorporate them into the product-building process.

If you're optimizing at the product level, your engineering team can be made up of product-minded engineers. People who are mission-driven and able to put themselves in the customer's shoes. These folks don't have Ph.D.s, but they're critical thinkers with a strong background in high-level tech stacks. Frameworks like Ruby on Rails, Express, and Django are perfect for teams optimizing at this level: high on productivity, and easy to build teams around.

You'll also want a strong product leader and at least one designer by their side. Some of your earliest employees will be customer success reps with strong product minds as well. From day one, all the leaders of your company should be asking customers questions, not necessarily trying to sell them anything, but focusing on the deep pains they feel day-to-day.

Companies that optimize for product usually don't have enterprise sales reps early on. They tend to pursue lower-touch sales channels and smaller customers. That means early sales teams will be sales-hacker types, sending a lot of cold emails or working closely with marketing to build a robust inbound funnel. These are not relationship builders, they are consultative sales types, focused on highlighting the pain points the product solves and answering questions in earnest. If your company is optimizing for product, but your sales team has to take customers to a steak dinner before closing them, you should probably either move upstream and optimize for sales, or pivot your product.

If you're optimizing for sales, you may be able to get away with outsourcing your product development. This can lead to significant savings in R&D, and more spend on Sales and Marketing! By focusing on a minimum sell-able product, you can sell ahead of your actual ability to fulfill. You'll truly let the market define the product, by getting leads to sign contracts for functionality, and then scrambling to build that functionality in time to on-board the customer. One subtle risk in outsourcing engineering is that your product may top out at some point. Undervaluing engineering tends to work in the short-term, but it can lead to longer-term technical debt that is expensive to pay off. Basically, the foundation of your tech platform may be wobbly, and at some point that wobble might give way.

Companies that optimize for sales also run the risk of chasing revenue until they become a services company. Early on, they may look like a high-leverage technology company, but in time their margins might fall. The factor at play here is that the cost of outsourcing technology prototypes is so low early on, your numbers might look like a technology business when really many of your customers are paying for custom builds. If the foundation underneath those custom builds is shaky and built by a team of outsourced engineers (whose incentives were never aligned with the long-term interests of the business), you'll have trouble scaling the platform (and with it the unit economics). Gross margin growth can stagnate as a result, and you may never achieve the high margins that a technology-optimized business can (assuming it gets to market!)

All three of these models work. Not one is a sure winner (or loser). Given just how few resources you have as a small business, and how critical focus is, it's a worthwhile exercise to decide where you are in the stack, and how you want to differentiate. Fundamentally, this is a culture and vision question that should be determined by the founders.

If you optimize for tech you will probably build an introverted company of geeks, with a narrow focus and a clear value proposition.

If you optimize for product, you'll end up with a customer-centric culture and team, a mix of introverts and extroverts, and a big vision that motivates and unites them.

If you optimize for sales, you'll have an extroverted, driven culture that is motivated by revenue growth and signing big new customers.

If you are still in the early days, it's worth having the conversation about what cultural and corporate attributes you are hoping to build, and where on the stack that places you.