Welcome to Leadership Land! Most of our new supervisors come from the Employee Lowlands, but others come straight from Grad Schoolopolis, Militaria, or Self-Employedistan. Almost all immigrants must surmount an obstacle to gain access:
Many scale the Interview Mountains that surround Leadership Land.
Military officers must climb to the top of Command-and-Control Ridge with a 90-pound backpack, run the entire length of the Ridge in 20 minutes or less, and do 50 push-ups while singing the national anthem to receive their commission.
A select few (Harvard Business School graduates) are airlifted straight into Leadership Land by headhunters. Fewer still enter via Nepotism Pass or the Crony Cave network.
Not surprisingly, many first-time managers commemorate their arrival in Leadership Land with a celebration. It often involves the consumption of intoxicating beverages, an intent to spend their additional income on a fancy trinket, or a plan to reshape the organization as they see fit.
Feel free to indulge yourself a bit. After all, you deserve this, right? You earned that promotion. Probably.
Many roads diverge, and we take the one less traveled
After the post-promotion hangover wears off, most newcomers to Leadership Land will do one or more of the following:
Dive headlong into the Boss Forest with a 5-year plan, with their sights set on the top of Executive Mountain (this is common among the HBS types)
Ask more experienced denizens of Leadership Land for advice on where to go next
Furtively look around at what everyone else is doing, then follow the crowd
Inhale listicles, books, and TED talks about navigating Leadership Land
Take new manager training offered by the organization
Wander aimlessly
Options #2, #4, and #5 will provide you plenty of information on what to do for developing your leadership skills, and we can’t compete with the big-name incumbents. Instead, our value proposition is to focus on where NOT to go, and what not to do in your attempts to become a better leader. Here’s why it’s better to avoid being a bad leader than trying to be a good one.
We hope that you choose option #7: making Adventures in Leadership Land your go-to travel guide!
Here are five travel tips for first-time supervisors:
1. Think about terrible people and figure out how to not become like them
Did you have a toxic boss? Work alongside terrible team members? Escape from a hostile work environment? Don’t dwell on those experiences – use those dark memories as a tool to craft a brighter future.
Make a list of behaviors that scared you, scarred you, irritated you, alienated you, (insert unpleasant verb here) you. Resolve to not pay those behaviors forward to the team that you will soon be supervising. As you take your first steps into the Boss Forest, don’t try to be a good leader. Start by not being a bad boss.
2. Look up miserable failures and figure out how to avoid the same fate
There’s an old saying that:
Smart people learn from their mistakes. Wise people learn from other people’s mistakes.
By that definition, the authors of Adventures in Leadership Land are very, very smart. Do as we say, not as we do.
As you explore Leadership Land, you will hear all sorts of cautionary tales. There’s Bob, trapped in the Career Swamp for being too good at one specific thing and incompetent at everything else. There’s Sarah, who got lost in the Middle Management Foothills and never made it to Executive Mountain. There’s Albert, who was swallowed by the unintended consequences that lurk under the shifting sands of the Desert of Good Intentions. From the Straits of Conflicting Interests come legendary tales of banishment from Leadership Land – stories of malfeasance, embezzlement, gross negligence, dereliction of duty, and sleeping with a subordinate.
It’s common to conduct postmortems on dead bodies and dead projects. Why not conduct a pre-mortem? Close your eyes, visualize yourself in the midst of a preventable crisis, and reconstruct the most likely chain of events that led you to this hypothetical situation. For example:
Do you have a flirty streak? Your pre-mortem should include a sexual harassment lawsuit.
Do you procrastinate on difficult conversations? Your pre-mortem should include a wayward subordinate whom you didn’t rein in before they figuratively blew up a client’s account, or literally blew up a building.
Do you love winning arguments and showing people the error of their ways? Your pre-mortem might include a fistfight, lawsuit, or boardroom battle that leads to your exile from Leadership Land.
Then, open your eyes. Let the relief wash over you, like the feeling of waking from a nightmare. And turn your pre-mortem findings into preventative action1.
3. Beware the unseen, unheard, and unknown.
You’ve prepared résumés and curriculum vitae (CVs) to show others what you know. Has anyone asked you to produce an anti-résumé or an anti-CV to show them what you don’t know?
No? What a shame. After all, un-knowledge can have a bigger impact on your career than knowledge. It hurts more - much more - when you’re unprepared for a knife in the back, or the unveiling of a great product that your competitors developed in secret.
Take hiring, for example. Lindsay looks great on paper, with 20 years of experience in underwater basket weaving. She uses the S.T.A.R. (Situation, Task, Action, Result) method to narrate a vivid tale of the time she used her underwater baskets to save a litter of three-legged puppies from a burning orphanage. How could you not hire such a stellar candidate?!
Pause a second, and look beyond the information presented to you. Did she get 20 years of experience, or did she get one year of experience 20 times? If her heroic rescue of the orphaned puppies was so spectacular, why can’t you find a secondary source to corroborate it? Did she cherry-pick her references from the members of her network who are most likely to give her a glowing review? (Answer: yes.)
In Leadership Land, it pays to be skeptical about everything: what your subordinates tell you, what your boss tells you, even what authority figures are telling you. Listen to their words, and take the additional step of wondering what they aren’t telling you. Look for secrets in the negative space between their words and actions. The unseen, unheard, and unknown lurks in the vast network of dark caves and tenebrous tunnels beneath the surface of Leadership Land.
4. Don’t feed the imposter syndrome
Note: HBS types can skip this section. Scientific Stereotypical data indicate that holders of elite degrees are immune to humility.
Maybe you were promoted from within your organization, from a technical position to a managerial role. Maybe you’re a new tenure-track professor who finds herself managing several graduate students. If you never received any first-time supervisor training, it’s like traveling to a foreign country with no map. You may feel apprehensive, anxious, or inadequate.
Good. A healthy measure of self-doubt shields you from complacency. In most cases, being afflicted by a mild case of imposter syndrome is better than hubris2. But if you let the self-doubt grow out of control, it will overwhelm you. Excessive self-doubt can lead to:
Poor decision-making
Inaction due to procrastination or “paralysis-by-analysis”
Loss of confidence from your subordinates and superiors.
The authors of Adventures in Leadership Land are no strangers to imposter syndrome, and we’ve devised a mental trick for overcoming it: we characterize it as a neurotic dog living inside our brains. It sniffs around for inadequacies and howls whenever it finds one, making it hard to focus on the task at hand.
If we feed the dog by dwelling on personal inadequacies, we are rewarding its behavior and making it stronger. The dog will call for attention more frequently and vociferously because we trained it to do so. If, instead, we starve the dog, its howling dwindles in both volume and regularity.
This is where the analogy breaks down, because we condemn animal cruelty and negligence. The takeaway lesson: don’t feed the imposter syndrome. Try to treat the feeble howls as data points: information to heed or ignore at your discretion. If you’re still struggling, we wrote a guide about managing your emotions.
5. Distrust conventional wisdom when playing a zero-sum game.
There’s no shortage of advice on how to be a good leader. The self-help section of your local bookstore is overflowing with books entitled “How to X in Y steps”, covering topics such as:
be an effective leader
raise a child
find a life partner
become a millionaire
get six-pack abs
build a space station
rescue three-legged puppies from burning orphanages
There’s a lot of advice out there, but how do you tell if the advice is any good? For your Leadership Land welcome package, we’ll provide a simple mental shortcut:
If there’s an often-repeated piece of advice that applies to a zero-sum game, treat the advice as if it were radioactive.
A quick review: zero-sum games can be summarized as “one person’s loss is another person’s gain.” Examples include college admissions, hiring, promotions, dating, and market share - any situation where many people/organizations are vying to occupy a limited number of slots. If everyone is using the same strategy (that is, following conventional wisdom) to occupy the slot, there’s only one way to gain the upper hand: try harder. Even if you can summon superhuman stamina to outwork, outlast, and outperform your competitors, a war of attrition is rarely the best use of your time.
For an illustration, let’s compare two pieces of conventional wisdom:
You should treat your employees well by showing them kindness
You should hire tough by spending more time and energy on attracting the best candidates
Kindness: not a zero-sum game
Showing kindness to one subordinate doesn't prevent the others from getting the same treatment. Unlike a bonus pool, kindness is not a limited resource that can be depleted and cause you to mistreat everyone else. You can generate kindness at will by practicing empathy when your employees encounter difficult situations, or by showing magnanimity when they make mistakes. This piece of conventional wisdom, applied judiciously, is a solid method for reducing your employee attrition rate3.
Hiring: a zero-sum game
Let’s make the spurious assumption that candidates can be objectively ranked on a single scale of “great - good - middling - bad - atrocious.” Let’s further assume that these rankings will remain constant as people move from one work environment to another. These assumptions are only for this thought experiment; they are very dangerous to assume in practice.
You run a circus and have been disappointed with the lion tamers you’ve recently hired. Upon hearing a motivational speech from some has-been CEO or an HBS professor, you decide to follow the conventional wisdom of spending more time and energy on hiring. You make your interview process twice as long. No longer will a simple résumé suffice; lion tamers must now run the gauntlet of two interviews, and also demonstrate their whip-cracking and chair-twirling abilities in-person with an actual lion (you will evaluate from behind a lion-proof screen). This way, the only lion-tamers you hire will be top-notch, right?
But wait! The competing circus from across town decides to spend thrice the energy on hiring. Worse still, they manage to poach your most experienced lion tamer by offering a generous sign-on bonus and industry-leading 401(k) match and complementary lion-maiming insurance. This forces you to quadruple your efforts on hiring.
The pool of top-notch lion tamers has not grown. Meanwhile, both circuses are now spending 4x more time and energy on the zero-sum game of competing for the same number of candidates. At least, this is what you heard from old contacts in the industry, because you were fired for spending too much time filling vacancies. While you following conventional wisdom by “hiring tough,” you weren’t running enough lion-taming shows to attract crowds and revenue. Oops.
No one ever told you that conventional wisdom (in the context of zero-sum games) are plagued with survivorship bias, did they? Of course not; the Silent Graveyard beneath Leadership Land is very, very quiet. The hiring managers who got lucky with their 4x strategy, or had the brand recognition and resources to attract the best candidates, are the ones who continue peddling this advice. The unlucky ones who “hired tough” and failed were exiled from Leadership Land - they’re too busy subsisting on expired cat food to give advice on hiring best-practices.
Let’s recap: conventional wisdom regarding zero-sum games is rarely good. At best, it’ll help you stay in place or gain a small advantage at the margins. At best, conformity leads to mediocrity. We’ll continue this topic in another essay about when to follow the crowd vs. when to think like a contrarian.
We hope you found these “don’t go there” travel tips to be entertaining and helpful. In future posts, we will unpack many of the themes and concepts alluded to here.
Your pre-mortems should not be limited to only career-related considerations. Illness, marital problems, a drug addiction, a car accident, and a lawsuit out of left field can all end a career from the outside as easily as a work-related event from within. Additionally, your pre-mortems should not be limited to acts of commission. An act of omission, like neglecting your health, spouse, seat belt, or liability insurance, can also lead to a ruinous end. The decision to do nothing can be as impactful as the decision to do something.
Excessive self-doubt leads to inaction (acts of omission) and excessive confidence (hubris) leads to wanton risk-taking (acts of commission). We believe that both types of acts are equally harmful. However, those afflicted by hubris are blind to their own shortcomings, and deaf to suggestions for improvement. Therefore, we believe hubris is more dangerous in the long run.
This example contains two over-simplifications. First, we are not suggesting that you play favorites, tolerate insubordination, or overlook the same mistakes again and again. Even if kindness were unlimited, you shouldn’t allow it to undermine your authority. Second, kindness is not truly unlimited. Some people have very little to spare before they reach their emotional capacity and lash out; their kindness is a limited resource! But even if you happen to be Pope Beneficient the Kind and can provide kindness as a full-time job, you’re still limited to 168 hours per week.