The Maladjusted Leader

To become a better leader, become better at managing stress.

We’re gonna make it that’s for sure,
if you’re stressed than let it go.

I really know how it feels to be, stressed out, stressed out,
When you’re face to face with your adversity

We’re gonna make it that’s for sure,
if you’re stressed than let it go.

A Tribe Called Quest feat. Raphael Saadiq and Faith Evans, Stressed Out Remix

The Verge’s expose on culture cultivated under former Away Luggage CEO Steph Korey reignited a common discussion in tech. The article is worth a read but the highlights won’t be too surprising for anyone who has seen HBO’s Silicon Valley. While Korey’s since been replaced as CEO (an outcome I’m unsure is the best solution), I believe the lessons and discussions shouldn’t be emphemeral.

You’ve got a CEO insisting on public-only conversations, taking public opportunities to shame and bully employees.

Here is the CEO referring to an employee as brain dead:

Publicly providing “feedback” that an associates thinking isn’t up to expectations for their level:

And publicly providing a career opportunity in the name of “empowerment”:

I thought this was leadership

I’m disheartened to admit that I too once believed this was leadership. Here we have a hands-on CEO setting the bar for their team. Business school case studies are filled with business heroes such as Andy Grove — who touted paranoia as a strategy in “Only the Paranoid Survive”.

Are the slack messages above that different from stories about Bill Gates, Steve Jobs, and Jeff Bezos leadership style?
In a 2008 article titled covering Tim Cook’s leadership style, Fortune included this moment as an example of Tim’s leadership strength:

One day back then, he convened a meeting with his team, and the discussion turned to a particular problem in Asia. “This is really bad,” Cook told the group. “Someone should be in China driving this.” Thirty minutes into that meeting Cook looked at Sabih Khan, a key operations executive, and abruptly asked, without a trace of emotion, “Why are you still here?”

And Elon Musk:

Many sources who spoke to Wired also described frequent outbursts where Musk would shout at people and call them “idiots.” A senior engineering executive said employees even had a name for Musk’s behavior: “the idiot bit.”
“If you said something wrong or made one mistake or rubbed him the wrong way, he would decide you’re an idiot and there was nothing that could change his mind,” the executive said.

So you’ve got the C-suite, leaders of companies that pride themselves on rigourous hiring–using their positions to publicly deride the team they built through this “rigourous” hiring process.

I think there are two things going on here. The first is clear: Steph Korey is demonstrated a poor philosophy of leadership. The second point is a bit more evolved, involved we have the right philosophy of what leadership is, what is our personal accountability as present and future leaders to carry that out effectively?

A better philosophy of leadership

Noted VC, Fred Wilson posits that there are three jobs of CEO:

  1. Set the overall vision and strategy of the company and communicate it to all stakeholders;
  2. Recruit, hire, and retain the very best talent for the company; and
  3. Make sure there is always enough cash in the bank.

This perspective is pithy but incomplete. You can set a vision, strategy, recruit and retain great talent, and make sure there is enough cash in the bank–and end up with Xerox Parc, a well funded research program filled with the best team and vision—yet unable to deliver customer or business value.

This is the job that’s missing. A CEO needs to shepherd an organization that delivers value.

How Google Works highlights a view that better maps to my own:

The primary objective of any business today must be to increase the speed of the product development process and the quality of its output.

Schmidt, Eric. How Google Works (p. 17). Grand Central Publishing. Kindle Edition.

I’ve adapted this to be less “product”-centric:

The primary objective of any business today must be to increase the speed of its value-creation process and the quality of its output.

So, if this is the goal of the organization, the job of any leader is to increase the speed of the organization’s value-creation process and the quality of its output.

Many leaders read this and envision themselves the Quarterback or Point Guard for the team. Leading from the front lines and driving the organizations process and quality. I imagine that’s what Steph Korey was aiming to demonstrate.

But in most organized sports, it’s not the player who drives the process. It’s the coach.

A leader’s job is to coach a team to increase the speed of the organization’s value-creation process and the quality of its output.

MikalFM, The Job of A Leader

A leader’s job is to coach.

Ori, a colleague at Microsoft, once asked me, “Whats the ideal size of a team?” I was puzzled, as I had recently joined a different team and thought my interview process was over. Why was he quizzing me now?

Me: “Um, I don’t know–two”
Ori: “One”
Me: “Wait, why?”

Ori: “If you can solve a problem with one person, why solve it with two? You add members to a team and project, only insofar as you can’t achieve team and project goals with the existing numbers of team members.”

Ori was coaching me through parable (something coaches do). The theme of this and other discussions between us, was that we often confuse our “role” for our “job”.

As a Product Manager, my role on a project or team exists, only insofar that the probability of the project success is materially increased with my addition. And the other side of the coin, my job was to push a project team to improve the probability of project success. And that my job was to coach the team to create that value without me, serving as a force pushing the team towards its ideal team size.

I’ll explain this a bit further.

Bezos knows a thing or two about scale. Since becoming a publically traded company under his helm, Amazon has grown by more than 100,000%. As a fan of scale, Bezos pushes extols the value of scaling team’s ability to operate without gate-keepers.

“I am emphasizing the self-service nature of these platforms because it’s important for a reason I think is somewhat non-obvious: even well-meaning gatekeepers slow innovation,” writes Bezos. “When a platform is self-service, even the improbable ideas can get tried, because there’s no expert gatekeeper ready to say, ‘That will never work!’ And guess what – many of those improbable ideas do work, and society is the beneficiary of that diversity.”

On this side of the 21st century, value has been created in society by pushing tasks towards the ideal team size. On design teams where you used to have “design production” churning out design revisions and changes into engineering red-lines, the same value is created by a team of one through tools such as Zeplin and InVision.

The growth in what an organization can accomplish at the atomic unit (a team) has lead to our society tackling increasingly wicked problems. We have autonomous vehicles today, and the competitive differentiator isn’t the fact that a vehicle can drive itself. Every automotive provider has some autonomy, it’s the quality of that process which is the differentiator.

As a testament to this, since 2018, three organizations have been at times surpassed a trillion dollar valuation. These three are the only three companies to accomplish this in history. All three organizations, Apple, Microsoft, and Amazon have accomplished this with one CEO.

The scale, speed and quality of their value-creation process have improved exponentially, and the available brain capacity at the seat of it’s most senior role has remained fixed (one CEO, one brain). In fact each CEO has become less-active as they were, or is notably less active in day-to-day management than their predecessor. They are accomplishing more, with less active management from their most senior leader.

The growth in what the organization can accomplish is due to organizations and technology becoming better at pushing teams towards their ideal size: the smallest possible unit. In other words, everyday one person teams are getting better at accomplishing what used to take two person teams, and two person teams are getting accomplishing what used to take four.

This is accomplished through organizations, that focus on the value enabled by anyone individual as well as leaders who “coach” organizations to “increase the speed of their value-creation processes and the quality of their output.”

Irreplaceable people hold back the organization.

Irreplaceable people are never promoted … To make themselves feel important and indispensable, they withhold critical data from others, refuse to delegate anything but the most mundane tasks, and retain all decision-making authority. They actually create a scenario in which their absence from work, for even a day, brings their unit or department to a halt until their return. They are often talented people actually working at assignments below their abilities. By creating complexity in a function that doesn’t necessarily require it, they appear indispensable. Or they may be limited in their organizational and procedural abilities, preferring to embody in themselves all the structure that their function may require. Over time, they’ve come to be their position rather than serve in it.
To be a fast-track person, you need to make yourself easily replaceable. To accomplish this you will need to:
(1) Document your job // coaching
(2) Train and develop your subordinates // coaching
(3) Cross-train your lateral colleagues to cover your position. // coaching
(4) Pick a lieutenant and be sure she is ready to step into your shoes.

Asher, Donald. Who Gets Promoted, Who Doesn’t, and Why, Second Edition (pp. 15-16). Potter/Ten Speed/Harmony/Rodale. Kindle Edition.

If you’re reacting…“But I need to make sure we do it the right way…”, I’m empathetic to your point of view.

But first, let me highlight a tail of two leaders:

A Leader as Coach: Wants to feel pressure to keep up with the team. She wants her team learning so fast, and creating so much value she is always struggling to keep up or adapt processes to help the team get more out of the value creation process.

A Leader as Manager: Doesn’t allow a team to be smarter than they are. If the team learns something, it needs to be in his inbox right away so he can consider it when approving or rejecting the teams plans. He knows decisions move slow because they are waiting for him, but his calendar is backed up and if the team has to wait to ensure they get it right so be it.

If you’re a Leader as Manager, you can be sure you are slowing your team’s value creation processes. Too often leaders act as govenors on their team’s value creation activities, team’s value are gated by the leaders’ capacity.

Save for material decisions, I coach teams on how to turn a material decision into an immaterial or irreversible one, and to move forward with their best decision by default (regardless of whether or not I can weigh in). As a counterbalance, I coach the team to ensure their thinking produces artifacts that can be audited at any time.

Let’s look at this from the process view.

You want a decision-making or value-creation process that produces the valid outcome by default. A value-creation process where your team arrives at the valid outcome, but then takes on a second job of “convincing” you its the valide outcome is a faulty one. A team that expends a great deal of energy producing an “invalid” recommendation, that you veto based on some information or perspective that is knowable only by you, is a faulty value creation process.

Back in the day at Microsoft, there was a game of using spec review to attempt to find the bomb that made the feature team go back to the drawing board in search of a new approach.

This approach was and is a value creation waste. It’s like producing iPhones at a 30% failure rate. As leaders, we need to see these failures as failures of process. Our job is to coach the organization to take into account the information in our heads–upstream, so that we’re over time producing decisions that have strategic integrity and align with the organization’s priorities and goals.

A learning organization never pays above market value for a lesson learned, i.e. it coaches the team and provides information to ensure they aren’t making the same failures twice.

The Professional Manager is Dead. Long Live the Coach.

Coaching is no longer a specialty. You cannot be a good manager without being a good coach. You need to, (according to a 1994 study), go beyond the, “Traditional notion of managing that focuses on controlling, supervising, evaluating and rewarding/punishing”, to create a climate of communication, respect, feedback, and trust. All through coaching.15 And an essential component of high-performing teams is a leader who is both a savvy manager and a caring coach.

Schmidt, Eric. Trillion Dollar Coach (p. 27). HarperBusiness. Kindle Edition.

When new Product Managers, and Engineers, begin working on front-end experience, I spend a lot of time in discussions–establishing the language of consumer psychology and interaction design principals. I want these principals in their heads as they conceive and use solutions, because they are certainly in my head when I review them.

By pushing this knowledge to the team, issues that jeopardize the product’s success are resolved and indetified before our design review, and the design review becomes less of a place for feedback on product decisions, and instead becomes a team- driven Design Room, a shared space for learning and product inquiry.

At this time, I typically move to an as-needed consultant-only role on the project and go focus on new or different problems where I can add value… satisfied in the joy of coaching up yet another high functioning team.

As you can tell, this approach is distinct from that of the irreplaceable employee whom is never approved, you’ll see my recommendation is the opposite of: refuse to delegate anything but the most mundane tasks, and retain all decision-making authority. Even when you make a decision, the goal is to use it as an opportunity to “coach” the organization as to how to arrive at a decision that aligns with the organizations strategic intent. So that in the future, this decision doesn’t arrive at your desk.

Many people hold on to this information and authority as their competitive advantage. However your playbook is not your competitive advantage. You should actively give it away. Even if it were guaranteed that you could become Serena Williams simply following her practice routine—how many would pay that sacrifice? Let alone be able to make decisions in realtime about how to respond to a situation based on that training.

This is where all competitive advatage derives, at the intersection of the knowledge you give away, and the judgement and commitment you personally apply to that information.

A manager becomes a coach…

Trust is also an important theme among the best sports coaches … Red Auerbach, who, as a coach and executive led the Boston Celtics to sixteen NBA championships in thirty years, had a simple way of expressing the importance of trust: “The players won’t con me because I don’t con them.”
He believed that level of trust led to stability and to greater commitment from his players… And if the players feel secure, they don’t want to leave here. And if they don’t want to leave here, they’re going to do everything they can on the court to stay here.”
Schmidt, Eric. Trillion Dollar Coach (pp. 83-84). HarperBusiness. Kindle Edition.

Korey wasn’t coaching the team, nor aiming to make the team successful. First it’s clear she wasn’t coaching:

As previously mentioned, one of the most central dimensions of these athletes’ experiences was Coaching Actions, which included seven general themes:
Disregard the Irrelevant

It’s Not What They Do, It’s How They Do It: Athlete Experiences of Great Coaching, Andrea J. Becker

Bad managers yell to reap the temporary benefits of yelling

So if it’s not to coach, why do managers behave this way? To reap the temporary benefits.

YOUTH: Well, how do you explain my anger, then?

PHILOSOPHER: That’s easy. You did not fly into a rage and then start shouting. It is solely that you got angry so that you could shout. In other words, in order to fulfill the goal of shouting, you created the emotion of anger.

YOUTH: What do you mean?

PHILOSOPHER: The goal of shouting came before anything else. That is to say, by shouting, you wanted to make the waiter submit to you and listen to what you had to say. As a means to do that, you fabricated the emotion of anger.

Kishimi, Ichiro. The Courage to Be Disliked: The Japanese Phenomenon That Shows You How to Change Your Life and Achieve Real Happiness (p. 17). Atria Books. Kindle Edition.

Korey, stressed, frustrated, and unable to magic wand the problem, regressed to bullying as a leadership tactic to make employees submit to her will, not to solve the problem.

You can tell because there is no step of any problem solving technique that says the most effective thing is to first make everyone feel bad. Bullying, in this case was her poorly adapted stress coping mechanism, which feels good to the leader because it brings the immediate feedback of subordinates fussing over her concerns.

So we know what a leader should do–coach. Which comprises the seven coaching actions above.

But, how should we interpret Korey’s actions and what prevented her from taking the aforementioned steps?

While we may want to attribute it to Korey being a bad person, lacking empathy, or some other attribute, to do so is to fail at the seventh coaching action: “disregard the irrelevant”–why project malice on someone, who was clearly loved enough to be sought out as a cofounder, when the answer can be explained with context and observation: she is a CEO poorly coping with stress.

We’ve heard it before. Entrepreneurship is stressful. It is, especially true when you’re the CEO. Entrepreneurial CEOs, of which my trifecta of known jerks (Bezos, Musk, and Jobs) hail, formed decision-making habits in high stakes environments, where their decisions literally influenced the life or death of the company.

Most CEOs are managing an organization that has the resources to thrive and the stress comes with the desire to please Wall Street. But these entrepreneurial CEOs have literally developed abnormal stress responses from the weight of their decisions.

Results also showed that entrepreneurs can successfully manage conflicting work demands without undue stress. However, they do experience stress when trying to manage the demands of home and work. Interestingly, entrepreneurs do not experience tension associated with role overload. It appears that stress is associated not with the volume of work per se, but with the weightiness of the decisions that entrepreneurs must make and whether they are making the right decision.

Buttner, E. H. (1992). “Entrepreneurial Stress: Is it Hazardous to Your Health?” Journal of Managerial Issues, 4(2), 223-240

Entreprenurial CEO’s aren’t the only ones experiencing this stress. In fact, Dr. Robert Karasek’s work highlights that the most stressed members of Away’s organization were likely the Customer Service Team. The team has high demands and little controls of the outcomes of their work. At least the CEO gets to be mean to people as a stress outlet. The Customer Service teams had to cancel vacations (opportunities for stress relief) and take stressful feedback both from internal and external parties.

Using a longitudinal sample of 2,363 people in their 60s over a seven-year period, the researchers found that for individuals in low-control jobs, high job demands are associated with a 15.4 percent increase in the likelihood of death as compared to low job demands.

The reality is as Korey highlighted, these weren’t her finest moments. But the take away should not be that she’s a horrible monster. It’s that improperly managed, stress makes us all more like the Steph Korey that shows in these slack messages than it does ourselves.

As I mentioned, there are likely people whom I worked with earlier in my career who would probably say this is more me than not. Thankfully, I invested in my own interpersonal development and through my own journey including Pathwise leadership program, I learned the language of the constitutions of the self and how there is no destination we “arrive” at, but instead situations and context move us from one to another.

Higher functioning leaders do a better job at operating at stages 3-5 by default.

  1. Stage One: The Impulsive Balance. In stage one, the individual’s thinking and feeling, by adult standards, is illogical… under extreme stress most individuals can regress to this stage of functioning.
  2. Stage Two: The Imperial Balance. These individuals see themselves as having power over themselves, their environment and impulses. But regresses to a “that’s not my problem” point of view and simplistic models of fairness.
  3. Stage Three: The Interpersonal Balance. “The right way to do things is the groups way of doing things.” When operating at this level group places extreme value on reinforcing group norms, values, and status.
  4. Stage Four: The Institutional Balance. Individuals have a sense of self as a part of a society, and feel a sense of responsibility or conscientiousness toward that society. There is a need to strive and generate at this stage and the sense of personal identity is related to the ability to accomplish.
  5. Stage Five: The Interindividual Balance. These individuals tend to self-surrender towards ideals and other people simultaneously. Makes decisions based on more complex, situational constraints, multiple truths, present circumstances and the integration of emotion with logic to form context-dependent understanding.

Sources: Robert Kegan’s Evolving Self and Pathwise Management Program 2008

If you’ve ever felt like an adult is behaving like a two year old… you’ve caught them in Stage One.

As mentioned, someone isn’t “stage 2” or “stage 3” it’s context dependent. While the higher levels of constitutions of self are rarer for organizations and individuals—stage one is common to us all when we experience extreme stress.

As a part of my stress management toolkit, I look for any and every excuse to get out the building. Typically choosing a coffee shop just far enough for me to go on a fifteen minute walk (total time there and back), in between meeting marathons to expend nervous energy.

Our jobs as leaders are to coach members to produce faster and higher quality value without us, and we can’t coach effectively with our stress response system is going haywire.


Steph Korey’s experience as a leader has lessons for us all. First, is to reflect earnestly on what went wrong:

  1. She was operating with a flawed leadership philosophy, acting as a governor for her teams value as opposed to a coach fostering her teams value.
  2. In these instances, she demonstrated that she lacked adequate coping strategies for the stresses of the job.

The net impact is a set of slack messages that clearly capture a leader in a stage one constitution. Away is a very successful company, I highly doubt this was her all the time, but the reality is her failure on these fronts inflicted real harm to the psychological safety of her team, which is a pre-condition to high functioning teams.

What can we takeaway from this experience?

There is a secret to becoming a better leader it is to develop a stress coping routine that allows you to establish trust, and coach your team to increase the speed of its value-creation process and the quality of its output.

Failure to do so doesn’t mean you or your team will fail, it just means you, yes you, personally are a maladjusted leader. And I believe you can do better.

about the author

Mikal is a reformed startup CEO and experienced Product Executive based in Austin, TX. After years leading product teams at Microsoft, Nordstrom and most recently VP of Product at RetailMeNot, he now serves as a product coach helping teams in growing tech markets work their way up The Product Team Ladder.

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