The Adaptive Work of Leadership

The Adaptive Work of Leadership

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.

Leadership is a critically important aspect of any endeavor that involves a group of humans to coordinate towards a common objective.

Leadership tends to be embedded with a lot of other things that aren't leadership so there are some distinctions about work, management and communication that we need to make before we jump into leading others.

Technical vs Adaptive Work

Technical work is mostly "solve for X" kind of work - learning a framework or a technique to solve a specific kind of problem 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 (IC) 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 - to adapt to the situation at hand in order to continue performing highly.

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.

It is one thing to be a gifted individual contributor and another thing entirely to be an effective manager because they are distinct modes, which requires different skills and different ways of being.

The moment you transition from individual contributor 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.

Management vs Leadership

Before we continue, it's important to distinguish that leadership and management are two distinct practices.

Those who are responsible for the actions of other people in positions of authority manage systems and lead people.

Management focuses on systems of production - organizing the way work gets done. Specifically, increasing the relationship between inputs and outputs by designing and implementing better systems of production. This is called managerial leverage.

The concept of managerial leverage comes from Andy Grove’s insight that management is the discipline of influencing group productivity: a manager’s job is to enable the groups he/she influences (directly or indirectly) to produce stellar work product regularly and repeatedly.

Leadership is about how you interact with your people to work within the system, contribute to its improvement, and develop their individual capacity to lead themselves and/or others. This is called enrollment.

The reason why leadership and management get conflated is because they are both rendered through the same channel: communication.

Having a conversation about the system with which work gets done is not the same thing as enrolling them to uphold - much less improve - the system's standards and protocols.

To manage, you must educate in order to clarify - to communicate what must be done and why. This is sometimes called Commander's Intent.

To lead, you must enroll in order to motivate cohesive initiative - tailoring how you communicate to each individual and the group at large to maximize their intrinsic motivation to perform and ensuring their efforts have genuine purpose.

Effective management and leadership reduce to effective communication. Effective communication reduces to effective listening.

Great managers and leaders listen deeply so that their words carry the weight needed to propel the group in the direction it needs to go.

To listen effectively to others, you must learn to listen to yourself.

Leadership 101: Self-Leadership

Leading others starts with leading yourself.

To effectively manage a group's response to stress, you must first effectively manage your own stress response, learn to think for yourself, and have the courage to act on your convictions and live with the consequences.

All growth requires a baseline - and to rewire our responses to stress 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.

Managing one's stress response is a necessary condition for great leadership, but alone it is insufficient.

Leadership is also about developing the ability to think things through for yourself and act on your convictions.

To quote inimitable William Deresiewicz in his seminal lecture - Solitude and Leadership - to the plebe class at West Point

Thinking for yourself means concentrating on one thing long enough to develop an idea about it.

Not learning other people's ideas, or memorizing a body of information, however much those may sometimes be useful. Developing your own ideas.

I find for myself that my first thought is never my best thought. My first thought is always someone else’s; it’s always what I’ve already heard about the subject, always the conventional wisdom.

It’s only by concentrating, sticking to the question, being patient, letting all the parts of my mind come into play, that I arrive at an original idea.

By giving my brain a chance to make associations, draw connections, take me by surprise. And often even that idea doesn’t turn out to be very good.

I need time to think about it, too, to make mistakes and recognize them, to make false starts and correct them, to outlast my impulses, to defeat my desire to declare the job done and move on to the next thing.

Independent thinking is what distinguishes a leader from a bureaucrat.

A bureaucrat is someone who occupies a position of authority but does not lead -they merely keep the routine going.

To paraphrase William Deresiewicz:

Bureaucrats know how to answer questions, but don't know how ask them.

They can fulfill goals, but don't know how to set them.

They think about how things get done, but not whether they're worth doing in the first place.

People who have been trained to be incredibly good at one specific thing, but who have no interest in anything beyond their expertise.

In most organizations, most positions of authority are occupied by bureaucrats. Master conformists who offer safe, plausible ideas on the regular and have a talent for maneuvering by being whatever other people want them to be. They get along by going along, not taking stupid risks like trying to change how things are done or question why they're done. Excellent sheep who have the intellect for independent thought, but lack the courage to have any convictions that might disrupt their need for self-preservation.

Despite grandiose mission statements and company values - most organizations prize conformity above everything else. Excellence rarely gets you up the greasy pole. And when it does, it is the exception that proves the rule.

This is partially why the work on managing your own stress response is critical to leadership: you are constantly facing into the headwinds and internal turmoil. You must endure the stress of sitting with something long enough to think things through for yourself - or make peace that you can't think something through and go with your best guess. You must endure the stress of being wrong by pursuing courses of action that flow from your thinking. You must endure the resistance from subordinates, peers, and superiors who disagree or feel threatened by your opinions and actions. And you must endure the stress from risking (or achieving) public failure and negatively impacting those you lead.

Stress is the great randomizer of all skill and good intentions. No amount of being a good thinker or communicator matters if all that stuff goes out the window when the pressure is on. You must become familiar with your own idiosyncratic reactions to stress. You must practice how to think, how to communicate, and how to enroll while you are under immense stress.

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.

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 long before those limits get tested in real-world situations. We've all worked for people who shy away from this, hide their 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 reins as CEO someday, this work must be done. It must be done continuously and in advance - usually with a therapist and a coach. Self-directed self-work is necessary, but insufficient: 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 simultaneously expand and 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.

This requires knowing what the individual and collective stress thresholds for change and tolerance are and when you need to turn the heat up or down - and by how much.

In day-to-day it's knowing when to be a shit umbrella for your 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 and when to ask 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).

Again - you must listen. Deeply.

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 and meet the needs of the situation.

When leading 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 leading leaders 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 leading leaders of leaders - 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, how we naturally organize into hierarchies, and the origins of various forms of authority, 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.

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 own stress load relative to our stress capacity in the moment.

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:

  1. Building your leadership card deck - accumulate and practice a lot of techniques.
  2. 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)
  3. Being able to transfer the craft of deck building and hand-making to others
  4. Do therapy to increase your baseline adaptive capacity
  5. Repeat until retirement or death

Where I've built my leadership deck:

  1. High Output Management
  2. The Practice of Adaptive Leadership
  3. Crucial Conversations
  4. Leadership and Self-deception
  5. Leadership Without Easy Answers
  6. Never Split the Difference
  7. Influence
  8. Immunity to Change
  9. Ender's Game
  10. The Goal
  11. Reboot

EXAMPLE: when *I* am managing/leading, here's the mental progression I go through:

  1. Establish task-relevant maturity on technical vectors - IC technique, managerial technique, etc.
  2. 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.

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