Brave New Work

by Aaron Dignan

Posted by Anton Katunin on 12 April 2020
Tags: books, 5 stars

Overall this book is a good introduction into new way of working. It compiles a lot practices into place. It doesn’t go in depth but it shows you the direction you can explore yourself.

The key idea is to rethink how we interact and do work. It gives a new framework to think about the change. The book starts with establishing the ground work and introducing the new concept of Organisation debt.

Part one: the future of work

Organisational debt

I like this as a new concept. Naming is a powerful thing, and I saw how term "tech debt" has changed the industry.

I define organizational debt as any structure or policy that no longer serves an organization.

Steve Blank, one of the pioneers of the lean startup movement, initially defined it as “all the people/culture compromises made to ‘just get it done’ in the early stages of a startup.” Due to a lack of time, resources, or willingness to do the hard things, founders will put off developing fundamental programs such as employee onboarding or training.

I can’t agree more with that. One of the most common sources of org debt is the knee-jerk reaction. When mistakes happen (and there always will be something as you can predict everything) we immediately create a constraint that will prevent it in the future. Over the years the organisation starts drowning under the weight of those constraints. Government is the ultimate example of it.

The question that must be asked is “What would we do if we were starting with a blank sheet of paper?” If the answer is anything other than what we’ve got, we have work to do.

People Positive

Another foundational piece is to define the metric we will use to evaluate all work practices: People Positive and Complexity Conscious.

Jean-François Zobrist believed that if you trust people, they will do the right thing. Tomorrow when you come to work, you do not work for me or for a boss. You work for your customer. I don’t pay you. They do. Every customer has its own factory now. You do what is needed for the customer.

The foundation are trust and belief in human nature.

Rooted in the work of psychologists such as Abraham Maslow and Carl Rogers, this view maintains that people are naturally motivated and capable of self-direction.

You probably heard of self-determination theory that we have three innate psychological needs that drive and shape our behaviour: autonomy, competence and relatedness. The focus of People Positive metric is autonomy — the ability to make choices and direct our own lives, free from the control of others.

Complexity conscious

There is a subtle but important distinction between words "complicated" and "complex".

A complicated system is a causal system—​meaning it is subject to cause and effect.

Unlike complicated problems, complex problems cannot be solved, only managed. They cannot be controlled, only nudged.

Car engine is complicated, while traffic is complex. You can fix engine but cannot solve traffic, only manage it.

If we continue to treat the complex like it’s complicated, we’ll spend our careers frustrated that control is always just beyond our grasp.

Being brave

We may like to think we’re making rational choices all the time, but the fact is we’re biased. We prefer to stick with what we’ve got.

It’s often easier to make something 10 times better than it is to make it 10 percent better. . . . Because when you’re working to make things 10 percent better, you inevitably focus on the existing tools and assumptions, and on building on top of an existing solution that many people have already spent a lot of time thinking about . . . But when you aim for a 10x gain, you lean instead on bravery and creativity—​the kind that, literally and metaphorically, can put a man on the moon.

Good quotes

The man who grasps principles can successfully select his own methods. The man who tries methods, ignoring principles, is sure to have trouble. — Harrington Emerson

Technological progress has merely provided us with more efficient means for going backwards. — Aldous Huxley

Part two: the operating system

In part two the book offers "The OS Canvas" - a guide to see and shift organisation identity.

The OS Canvas

Purpose How we orient and steer
Authority How we share power and make decisions
Structure How we organize and team
Strategy How we plan and prioritize
Resources How we invest our time and money
Innovation How we learn and evolve
Workflow How we divide and do the work
Meetings How we convene and coordinate
Information How we share and use data
Membership How we define and cultivate relationships
Mastery How we grow and mature
Compensation How we pay and provide

The canvas helps us to assess how different our beliefs from our reality. Unfortunately in my experience it’s very common to see people say one thing and do the exact opposite.

If we say we want to hear every voice but spend most of the day talking over others, that tells us something. If we say we value agility, but every decision requires a dozen approvals, the opportunity is clear.


business of business is business.

Jim Barksdale, former CEO of Netscape, once quipped, "`Saying that the purpose of a company is to make money is like saying that your purpose in life is to breathe.

Evolutionary Organizations aspire to eudaemonic purpose—​missions that enable human flourishing.

steering metrics should, in fact, result in steering.

Don’t confuse your customer with your purpose.

essential intent, a goal that sits between your ultimate vision and your quarterly objectives.

every six months, we take another look at where we want to be in 30 years to plan out the next six months.

Ensure that any group in transformation—​whether it be a team, a unit, a function, or the whole organization—​has a strong sense of their collective purpose.


How we share power and make decisions; the right to make decisions and take action, or to compel others to do the same.

In complexity, our job isn’t perfection, it’s building a culture that is always learning.

This part mentions 'The Waterline' metaphor. It is an interesting practice to give people autonomy while securing yourself from big risks. In short you must consult with other knowledgeable people before taking action that might be 'below waterline' and cause serious damage.

It’s very similar to 'The Advice Process'. It allows anyone to make a big decision after they seek advice from colleagues who have experience with or will be affected by their choice.

Decision making process is another key pillar in the organisations. 'Consensus' is impossible at scale. Instead 'consent' is the way to go. The book suggests Integrative Decision Making method (IDM).

Above all, the method prioritizes inclusion and forward momentum. The final round is the breakthrough: someone who objects to a proposal cannot simply veto it but must try to shape it further to make it safe to try.

Integrative Decision Making Process steps: propose, clarify, react, adjust, consent, integrate.


How we organize and team; the anatomy of the organization; formal, informal, and value-creation networks.

Three structures. Every organisation has three structures:

  • The first is the formal structure, the realm of hierarchy, which exists purely for compliance with the law.

  • The second is the informal structure, the realm of influence.

  • And finally, the value-creation structure, the realm of reputation.

When we talk about organizing and teaming in new ways, about the inner workings of Evolutionary Organizations, it is their value-creation structure that we’re talking about.

One to many roles. Job titles are very abstract group for the roles you hold in a company. Within the company we should be talking about the roles. They give move precision and clear responsibility. Job titles are simply an agreed group roles. Such simplification is great when you are applying for job or want to summarise your job in one sentence.


How we plan and prioritize; the process of identifying critical factors or challenges and the means to overcome them.

Wild Swings and Sure Things. Keep 90% in safe investments and place 10% in highly speculative bets.

Careful with OKRs. You can meet the target and destroy the company. The perfect alignment eliminates divergence and serendipity.

OODA loop. Military strategist John Boyd created the OODA loop—​observe, orient, decide, act—​to explain how expert fighter pilots continually processed information in the heat of battle.

The even over statement, which is a form of strategy, does a great job of indicating that even though we value the thing on the right, we value the thing on the left more.

A red team is charged with one mission: putting you out of business.


How we invest our time and money; the allocation of capital, effort, space, and other assets.

The Beyond Budgeting folks believe that individual performance doesn’t really exist. Performance is a team sport.


How we learn and evolve; the creation of something new; the evolution of what already exists.

One of the primary goals of global brands and institutions is to eliminate variation and ensure conformity.

When we don’t know what’s going to work—​in a startup or new division, for example—​we need to increase exploration, randomness, and variation, even if it feels a little counterintuitive.

Defaults vs Standards. Defaults are exactly like standards with one exception: you don’t have use them. A default says: If you don’t know what you’re doing, do this. If you don’t have time to think, try it our way. But if you’ve achieved some level of mastery in an area and you think you see a better way, feel free.


How we divide and do the work; the path and process of value creation.

Keep the org chart for regulators and use the structure that delivers the most value for day to day.

Nothing but Projects. Treating everything as a project allows us to be more intentional—​starting, stopping, and evolving activity with the same level of scrutiny. A project has a purpose. A project has a cadence. A project uses feedback to learn. A project lens allows us to share a common language about the work of the organization.

Limit WIP, it increases flow and overall productivity.


How we convene and coordinate; the many ways members and teams come together. One-on-ones are often used as a salve for hidden dysfunction. When members lack the authority to make decisions, these meetings become the only mechanism for moving things forward. When members lack the ability to resolve conflict, these private audiences with the leader become a forum for politicking. Great one-on-ones can provide feedback and mentorship, deepen relationships, or give us a chance to collaborate on the work.

Governance meeting The goal of this meeting is for everyone to have the chance to voice their concerns and propose local changes to structure, strategy, resources . . . anything that will help the organization pursue its purpose.

Start meetings by checking in. Beginning with a question allows us to connect on a human level. We want to hear from everyone. Typical questions include: What’s on your mind? What are you looking forward to? What’s the biggest risk you’ve ever taken?

Speak and participate in rounds. When we want to prioritize speed and inclusion, we’ll go around the table and give everyone one chance to provide updates, ask questions, offer feedback, or give consent, depending on the type of meeting we’re holding. Everyone else is invited to listen respectfully and wait for their turn to speak.


How we share and use data; the flow of data, insight, and knowledge across the organization.

Transparency. It’s difficult to overstate the degree to which Evolutionary Organizations value and practice transparency.

Because we can’t predict when the information reaches the right person at the right time, we have to aspire to what economists refer to as information symmetry—​a condition in which all relevant information is known to all participants. This is a continuation and expansion of earlier concepts such as open-book management, in which employees have access to financial information such as revenue, profit, cost, cash flow, and expenses. E.g.

Push vs. Pull. Legacy information sharing is “push,” meaning that the information is delivered to us without our consent. When information is pushed, we have to wade through it and separate the signal (what we need) from the noise (what we don’t). But when information is abundant, a “pull”-based system where information is tagged, stored, and ready to search is far superior.

If you’re legally obligated to keep certain information protected, you can adopt a policy of default to open. That means everyone starts with the assumption that all work should be open and searchable by default, unless there’s a good reason to secure it.

One powerful way to break patterns of secrecy and rumor is to host a regular Ask Me Anything (AMA) session with your function, division, or organization.

Increased transparency is critical in the early stages of transforming your OS, because it’s a prerequisite for making sound decisions. One of the most common mistakes I see is teams taking a swing at empowerment before ensuring transparency.


How we define and cultivate relationships; the boundaries and conditions for entering, inhabiting, and leaving teams and organizations.

In a complex system, the interactions matter more than the parts.

One of the reasons organizations end up rigid and risk averse is fear.

Bill Gore coined the notion of a “lattice organization” in which "`each person in the Lattice interacts directly with every other person with no intermediary.

Instead of fit, IDEO hires for cultural contribution. It asks, What’s missing from our culture?

Research shows that rituals can reduce anxiety or increase confidence and even help us assume contextual identities (think: soldier or firefighter).

Team Charter

  • Why does this team exist?

  • How do we contribute to the organization’s success?

  • What are we accountable for?

  • What is our essential intent for the next days?

  • How will we know if we’ve succeeded?

  • What principles will guide us?

  • What will we prioritize for the next days?

  • What are the roles required to do this work?

  • What roles will we each play?

  • Are there any roles not yet claimed?

  • What do we expect of one another?

  • Who are our users or customers?

  • What decision rights do we have?

  • What can we do without asking permission?

  • Within what guardrails do we have autonomy?

  • Are we responsible for anything that we don’t control?

  • How will we make decisions?

  • What resources do we control?

  • What is our meeting rhythm?

  • How often will we conduct retrospectives?

  • What tools will we use to communicate and coordinate?

  • How will we share our work with one another and the organization?

  • What are the learning metrics that will help us steer?

  • How will we know if we’re making progress?

User Manual to Me

The idea is genius: what if we each wrote a user manual about how to work with us and shared it with our teams?

Questions about you:

  • What are some honest, unfiltered things about you?

  • What drives you nuts?

  • What are your quirks?

  • How can people earn an extra gold star with you?

  • What qualities do you particularly value in people who work with you?

  • What are some things that people might misunderstand about you that you should clarify?

Questions about how you relate to others:

  • How do you coach people to do their best work and develop their talents?

  • What’s the best way to communicate with you?

  • What’s the best way to convince you to do something?

  • How do you like to give feedback?

  • How do you like to get feedback?


How we grow and mature; the journey of self-discovery and development; our approach to nurturing talent, skills, and competence.

  • Ray Dalio’s massive best seller, Principles

  • Peter Senge suggested the concept of Personal Mastery in his landmark book The Fifth Discipline

Do you worry more about how good you are or about how fast you are learning?

Here we see the connection between mastery and maturity. Talent and skills don’t matter if we don’t have the maturity—​the courage and humility—​to welcome the conditions for continuous growth. And our ability to do this has a lot to do with what psychologists call the four dimensions of core self-evaluation: locus of control, neuroticism, self-efficacy, and self-esteem.

The other manifestation of our complicated approach to mastery is training.

We always know more than we can say, and we will always say more than we can write down.

This is my favourite highlight.

We need to create work environments with high social density where members with different levels of knowledge and competence can work and learn together. We need to enable individuals to pursue roles and projects where their skills are stretched and flow is achieved. And when we do stop, we need to create safe and open spaces for experiential and self-organized learning, where memorization is replaced with dialogue and epiphany.

Role Mix. One of the greatest inhibitors to personal growth in the legacy workplace is the fact that we hold singular fixed roles. Being rooted in one function with a standardized set of accountabilities inhibits our ability to develop different skills in different contexts. …​ To make this real for your team, start by asking everyone to articulate the role(s) they’re already playing—​including the role name(s), purpose(s), and general accountabilities.

Ritual Feedback. Yearly review is too slow and often lack the details. Here is a better process:

  1. Set a time frame for deeper feedback that makes sense in your context. I recommend 120 days.

  2. On that interval, using software (e.g. Slackbot or Google Forms) or a team willing to facilitate, reach out to each member of your team, and ask them if they’d like feedback. If they say no, let it go. They’ll get another chance in a few months.

  3. If they say yes, ask them whether they’d like to use standard questions (start/stop/continue or similar) or write their own.

  4. Ask participants which three to five colleagues they’d like to receive feedback from. If you’re using software to automate this process, you may even be able to recommend the people they communicate with most frequently.

  5. Send the questions to their suggested colleagues with a time limit for contribution. Make this a ritual that is prioritized and celebrated in the culture.

  6. Compile and share the responses with each participant. Let them choose who to share it with, including their manager (if they have one).

  7. Invite participants to convene their respondents for an in-person sensemaking session led by them. The question on the table is “Based on the feedback you received, what questions do you have for your colleagues?” This is chance to zero in on things that they want to work on and make real breakthroughs and commitments.

  8. Finally, don’t let this feedback rhythm become an excuse to avoid real-time conversations and retrospectives. The end of every interaction, sprint, and project is an opportunity for feedback. Teams at The Ready try to take a moment for feedback after any key event. Leaving a new business meeting, I might ask a colleague, "`What did you notice? What happened? What surprised you? And what feedback do you have for me?

Mastery in change A certain level of maturity and competence is required to participate effectively in an Evolutionary Organization. Members who lack self-awareness or self-confidence may struggle with self-management. If you’re not able to be vulnerable, radical candor can be too threatening. It’s a shock to the system even for those of us who think we’ve mastered our egos. If you’re not clear on your own talents and purpose, self-direction can seem overwhelming. Everyone’s always told me what to do, and now I have to decide?


How we pay and provide; the wages, salaries, bonuses, commissions, benefits, perquisites, profits, and equity exchanged for participation in the organisation.

In 1959 psychologist Frederick Herzberg proposed an answer to that very question in what would come to be known as his two-factor theory. In trying to understand the factors that lead to job satisfaction, he discovered that the opposite of satisfaction was not dissatisfaction. Rather, satisfaction and dissatisfaction appeared to be driven by two completely different sets of variables.

It means that increasing salaries that are too low can reduce job dissatisfaction, but increasing salaries that are already generous won’t increase job satisfaction in any meaningful or lasting way.

Market Pay. Ask these three questions to determine the market pay. (1) What could this person get elsewhere? (2) What would we pay for their replacement? (3) What would we pay to keep this person, if they had a bigger offer elsewhere?

Good quotes

The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function. — F. Scott Fitzgerald`"

Part three: the change

In a system that’s not overly constrained, changes that serve us can spread quickly. Niels Pflaeging holds a similar view. He contends that “milk in coffee is a more helpful metaphor than the widespread notion of seeing change as a journey from here to there.” Like milk in coffee, the right kind of change can unfold throughout a system quickly and continuously.

At this point you might be realizing, Oh shit, we’re not just changing the organization; we’re changing how we change the organization.

Continuous participatory change

In our work, we’ve noticed six such patterns that, held lightly, are worth encouraging:


When those with power or influence commit to moving beyond bureaucracy.

Autonomy. All members and teams should be self-managing and self-organizing. Members have the freedom and responsibility to use their skills, judgment, and feedback loops to steer and serve the organization’s purpose.

Consent. All policy decisions—​agreements, rules, roles, structures, and resources—​should be made through the informed consent of those impacted by that decision. In the spirit of agility, members may consent to using other forms of decision making, including distributing authority to specific roles, teams, or elected representatives.

Transparency. All information should be made available and accessible to all members. Individuals and teams should “default to open” when it comes to sharing data, information, knowledge, and insights.

If you’re a startup, that means recruiting people who are not just skilled but ready to reinvent how they work.


When a liminal space is created and protected.


When the invitation to think and work differently is offered.


When change is decentralized and self-management begins.

Earlier we talked about designing change to reveal the adjacent possible. Within organizations, we endeavor to do this through a process we call looping, inspired in part by Jason Little’s Lean Change Management. In our work, a loop contains three stages that are practiced recursively: Sensing Tensions, Proposing Practices, and Conducting Experiments.

Sensing Tensions. In Peter Senge’s book The Fifth Discipline he briefly introduced a concept called creative tension. “Imagine a rubber band, stretched between your vision and current reality. When stretched, the rubber band creates tension. . . . What does tension seek? Resolution or release.” In Senge’s view, creative tension must be resolved by either pulling reality toward the vision (change) or pulling your vision toward reality (compromise)

Proposing Practices. Once a tension is identified, we can look for ways to probe it. In some ways, this is the hardest part of the process.

It seems that perfection is attained not when there is nothing more to add, but when there is nothing more to remove. — Antoine de Saint-Exupéry

Conducting Experiments. Our goal isn’t to make something work; it’s to learn, to see what’s possible—​what emerges. To that end, we’re going to take a moment to design a thoughtful experiment.

Operating systems are interdependent and self-reinforcing. That means that an isolated experiment might not work. Not because the change was ill conceived but because it relies on a broader context to be successful.


When the system has tipped and there’s no going back.

If you see the language changing at scale, that signals criticality. Because language is how we make meaning.

The second and perhaps more powerful sign is what we refer to as spread. This is what happens when the practices you’re introducing travel beyond the boundary you’ve set.


When continuous participatory change is a way of life, and the organization is contributing to the broader community of practice.

The operating system—​previously a black box—​has become facile and fungible. It is now a form of commons, owned by everyone, and everyone must maintain it.

The greatest athletes in the world have coaches. Why wouldn’t the greatest teams?

Psychological Safety

A system in trauma can’t transform. If we’re not safe, we can’t trust. If we’re not safe, we can’t risk. And nobody does their best work scared.

First, all the members of the team spent a roughly equal amount of time talking. The technical term for this is equality in distribution of conversational turn taking. Second, the members of the team displayed fairly good intuition about what the other members were feeling. This is referred to as high average social sensitivity.

A team is not a group of people who work together. A team is a group of people who trust each other. — Simon Sinek

At Emergent Inc. we decided to build some psychological safety right out of the gate, using a technique called ICBD. ICBD stands for Intentions, Concerns, Borders, and Dreams.

"My intention is to create a case study here that I can use in my book. My concern is that I won’t be successful in getting this group to open up. My border is that I leave work at 5:00 P.M. every day to spend time with my family. No late-night emails or calls with you just because we’re under contract. My dream is that this will spread to other parts of your organization."

The role of the leader

OS transformation is about distributing power, and while you might want to do that with one grand gesture, it actually happens one interaction at a time.

The biggest barrier to change, believe it or not, is you.

Man has no greater enemy than himself. — Petrarch

Your new job is to ensure that the conditions for change are in place, not just now but in perpetuity. While you won’t be doing as much “leading” in the traditional sense, you’ll be doing something far more rewarding. You’ll be creating and holding the space for change.

Creating space

As wonderful as your culture may be, it’s best to assume that some people in your organization don’t feel safe.

Continuous improvement is not magic; it is a discipline. It is a thing we do.

Holding space

Holding space means making room for teams to figure things out for themselves—​for failure, learning, and growth.

Principles for change

  • Through them, not to them

  • Start small

  • Learn by doing

    • The worst-case scenario is we all look at one another and agree: let’s not do that again.
  • Sense and respond

  • Start by stopping

    • The vast majority of rules and process are created because we don’t trust people to do the right thing.
  • Join the resistance

    • People can and do change. They just do so when it makes sense to them. People don’t resist all change; they resist incoherent change poorly managed

Scaling change

Clayton Christensen once told software entrepreneur Jason Fried, "`Questions are places in your mind where answers fit. If you haven’t asked the question, the answer has nowhere to go. It hits your mind and bounces right off. You have to ask the question—​you have to want to know—​in order to open up the space for the answer to fit.

Epilogue / what dreams may come

if you’re giving back, you took too much. — Ricardo Semler

Building and sustaining an Evolutionary Organization is an uphill battle when the economic OS is structured to promote growth and gains over purpose and meaning.

Whether you believe you can do a thing or not, you are right. — Henry Ford