A letter to a friend about leadership.
This encapsulates most of what I think I know about leadership and management from theory to practice.
Disclaimer: I don't have this figured out - the people I learned this from have forgotten more about leadership than I'll probably ever learn. I'm just very serious about my responsibility to those around me whenever I occupy a position of some authority - formal or not. Great power = great responsibility and whatnot.
The most salient leadership lessons in Master and Commander are subtle. I spot new ones on every rewatch. So I'm writing this primer to help you squeeze as much value out of your first pass because I know how expensive 2 hours is for you.
The punchline: This movie is an examination of one person helping others navigate uncertainty while simultaneously navigating their own private uncertainty when 1) retreat is not an option (because you are on a ship) and 2) no one is coming to save you (because you are on the other side of the planet from your fleet).
This is the burden (and paradox) of leadership: balancing private authenticity with public effectiveness and the sin eating one must do when their position forces them to choose the lesser of two evils. For example: allowing a man thrown overboard to drown to save the ship and crew.
There aren't many classes these days that offer live-fire drills for those situations in our industry, but I believe this stuff can be learned and refined through practice, reflection, and coaching.
Technical vs Adaptive Work
Technical work is mostly "solve for X" kind of work - learning a framework or a technique and then applying it.
Technical work is about skills that directly contribute to a company's means of production (analysis, design, coding, whatever). Most of an individual contributor's work is technical work.
This is different than adaptive work: building one's capacity to perform one's duty and craft under increasing levels of stress.
At an IC level, adaptive work is about doing one's job - coding, designing, whatever - under pressure from higher-ups, or in the face of personality clashes with peers, and personal life.
The moment you transition from IC to leadership, the game changes irrevocably: it's adaptive work all the way down.
At a leadership level, adaptive work is about managing the group's response to stress to ensure cohesion and performance in the face of a variety of stressful situations.
As leaders, our duties are no longer about coding or designing but preserving and enhancing the group's performance - whether it be coding, designing, or leading others - by effectively influencing their responses to stress.
Leadership 101: Self-Leadership
Leading others starts with leading yourself. To effectively manage a group's response to stress, we must first effectively manage our own.
To rewire our stress responses we must first distinguish them. For many, that requires continuously staring into a mirror most of us would rather avoid: the acknowledgment of our shadow self, our triggers, and the shitty ways we act out when we're triggered. Coming to terms with the underbelly of one's identity is necessary to create room for the emotional, mental and behavioral upgrades that leadership roles demand. Growth requires a baseline.
To be clear, it's entirely possible to get promoted into leadership roles without doing this work. Most do. This is because adaptive work is "below the line", it doesn't show up on a resume. And unless the one doing the promoting has done the adaptive work herself, this stuff will not factor into the decision. Which probably explains the profound mediocrity of our companies and institutions.
Yet, the more one hides from the adaptive work of self-leadership, the more they limit the long-term trajectory of their career. At some point, everyone gets promoted into a role where their ability to make it up as they go gets quickly overrun. They are unable to meet the demands of the situation, dampening the effectiveness of everyone around them before eventually getting managed out - Lieutenant Dyke style.
Successfully climbing the organizational ladder comes down to the breadth and depth of your capacity to manage your own stress response in the service of help your team perform and manager their own responses to stress.
You have to do the work in advance. For the sake of your health and career longevity, it's imperative to be continuously and proactively engaged in the internal work that expands the edge of your limits. We've all worked for people who shy away from this, hide a zombie bite, and eventually get fired after all the good talent have left.
For anyone who harbors desires of reaching their craft's top executive position or maybe taking the reigns as CEO someday, this work must be done. It must be done continuously and in advance. No podcast or book will save you.
Leadership's Job to Be Done
So assuming that we've got the self-leadership part handled, what is the day-to-day of leadership? First, it's not the clerical work that is typical of leadership roles - emails, meetings, etc. That's management (more on that in a second).
The job of leadership is to produce more leaders, not more followers.
Your job as a leader is to expand the adaptive capacity of those you influence directly or indirectly. Under this lens, leadership development is not some distinct thing done outside of the purview of getting work done. Rather it is a continuous ongoing process to help those in our charge build capacity to live more into their potential by connecting their personal growth to their professional work.
Read that again: to help others build capacity to live into their potential.
How do we do this?
Leaders must model the desired behavior. Humans learn and behave mimetically. Being a model to copy is a great first step because it serves as passive leadership development. But more importantly, being consistent with the "do as I say and do" approach builds the kind of social capital that is critical for leaders: informal authority. Informal authority is the genuine devotion and loyalty to leaders that exceeds the formal authority of the position.
Think of the bosses you've had. How many of them would you work for again? How many would you follow to the gates of hell?
As a leader, this requires balancing structure and ambiguity to keep direct reports in the zone of productive stress (aka eustress) which expands their adaptive capabilities. Knowing when to be a shit umbrella for your direct reports and when not to, when to give them the answer and when to let them figure it out, when to respond with a comment vs a question, when to be a mirror and when to be a guide - all while dealing with upstream influences on one's own environment which are mostly out of our control (pathological cofounders, the market, family stuff, etc).
Adaptive work is recursive
In leadership, the adaptive work is recursive: we expand our capacity to help others expand their capacity to operate under stress.
When managing ICs - we must attend to expanding both the technical and adaptive capacities of our direct reports, raising their baselines high enough that they won't get crushed in their first managerial role.
When managing managers of ICs - we attend to expanding the adaptive capacity of our direct reports to expand the technical and adaptive capacities of their direct reports.
When managing managers of managers - we attend to expanding the adaptive capacity of our direct reports to expand the (mostly) adaptive capacity of their direct reports.
and so on...
Leadership has no easy answers
Alone, the movie is merely another angle at something you and I experience on the regular. But it is not a prescription for what to do. It is (thankfully) just a koan.
The bones of a prescription come from places like Ron Heifetz's Leadership Without Easy Answers that start with 3 chapters about evolutionary biology, group psychology, and how we naturally organize into hierarchies before getting into the meat of leadership. Even then, that's simply a lens for spotting and selecting interventions that are more likely to work.
By the way - none of this has anything to do with management. That's because management and leadership are not the same thing.
Management is about structuring the work to produce leverage between inputs and outputs of the company functions you are responsible for.
Management can be thought of as authority's technical side: it attends to carefully choreographing the conversion of financial capital into human capital back into more financial capital. Leadership is about using the work to expand the adaptive capacity of the human capital part.
Management is the science of human progress. Leadership is the art of human progress.
You and I know that leadership doesn't have easy answers. But there's still the reflex that looks for them: a single framework or method or technique that we can copy+paste into our next meeting and check off our never-ending list of things to do. That's because it's human nature to want technical solutions to adaptive problems. There is no one answer.
The solution is to find ways to come up with the answer needed for each unique, fleeting circumstance in front of us.
The adaptive answer to the adaptive problem of leadership is that we must be constructing and reshaping technical answers on the fly to fit the small Venn diagram of: the firm's circumstances, the individual preferences, coachability and task-relevant maturity of who we are leading, and our adaptive capacity at the time.
In practice, leadership is like having a stack of cards, where each card is a different technique designed for a specific scenario - a leadership design pattern if you will - and you are constantly reshuffling the deck to generate the hand you need to play at any given moment.
Building leadership craft
Given everything above, a general approach to building leadership craft could be described as:
- Building your leadership card deck - accumulate and practice a lot of techniques.
- Mastering the art of generating the hand you think you need - and working with a coach to close the feedback loop (this is why I personally like 360 reviews quarterly or bi-annually)
- Being able to transfer the craft of deck building and hand-making to others
- Do therapy to increase your baseline adaptive capacity
- Repeat until retirement or death
Where I've built my leadership deck:
- high output management
- the practice of adaptive leadership
- crucial conversations
- leadership and self-deception
- never split the difference
- influence (cialdini)
- leadership without easy answers
- immunity to change
- how the way we talk can change the way we work
- ender's game (yes really)
- the goal (goldratt)
- reboot (colonna)
EXAMPLE: when *I* am managing/leading, here's the mental progression I go through:
- Establish task-relevant maturity on technical vectors - IC technique, managerial technique, etc.
- Assess current adaptive capacity (baseline + upper threshold) and how their stress response causes them to act - starting with capacity for self-management:
- psycho-emotional flexibility - can they distinguish between what happened and their interpretation of it? can they easily switch between different interpretations?
- proactive self-awareness - do they know their shadow self, their stress responses to various triggers and scenarios
- ownership of pathologies - ability to proactively clean up the emotional messes they make with others
- coachability - are they resistant to or surprised by identity-shaping feedback
- worldview (and the priors that shaped it) - familial, cultural background, philosophy, etc.
4. Establish their personal career goals (to contextualize their time here).
5. Look at what kind of work I need them to do for the company.
6. Try to construct their workload and responsibilities to foster an intelligent progression to prepare them for their next thing.
7. Coach regularly using different combinations of cards from the leadership deck.
Parting thought: I'm constantly learning
Leadership is a lifelong craft and there's never a bad time to learn it. Nor is there any one way to learn it. The above is just the way a bunch of exec coaches taught me. Looking forward to comparing notes when you get a chance to watch M&C.