Rebecca Weekly

We have ended year one of our little book club! 12 different books around leadership, management, goal setting, organizational behavior, and systems thinking. I hope it was an opportunity for folks to think through their leadership styles and reflect a bit on how they want to show up in the world whether they are a people manager or a technical leader, at a small or large corporation, or within an open source consortium–we have such a range of folks and styles I know I have learned from so many folks. In the new year, our book club will take an alternative shape focusing less on leadership, and more on the trends happening in technology and their ethical implications. Please sign up here and recommend a book in theme if you want to participate.

Our last book of the year was Measure What Matters, which is definitely a canonical piece. Most folks enjoyed the book, although it definitely hasn’t aged all that well (looking at the outcomes of so many of the companies he highlighted as poster children of OKRs). I loved it because goal setting and accountability are core to execution and I like to be the kind of person who accomplishes things. It is definitely a US-centric book, and we discussed as a group what that “means” in other contexts, since so many of us manage global teams or at least work closely with teams all over the world. It also is light on implementation details (more on impact of where it was rolled out successfully, but not necessarily HOW to roll it our successfully, particularly now when so many of us are in a remote-first work environment and with globally-distributed teams). There was also some commentary about the fact that the book really speaks to a time with few female leaders. Sadly I think this is just the reality of the time frame and not really a critique of the book (e.g. Andy Grove’s Intel was not all that diverse–no company was 40 years ago, and that was the birthplace of OKRs).

In general though we had a great discussion on the value of these efforts: the checkpoints and discussions. Whatever systems you use for goal setting (V2MOM , OKRs, etc.) the magic is in the discussion with your teams and employees. It is in the bottoms up strategic alignment WITH upper management (it cannot just cascade down, it has to go in both directions) and it is in the discussions when you grade them with your team. I have learned so much with my team members: the folks who CANNOT handle seeing anything less than a 1, but who also didn’t quite feel like it was a WIN; those who grade themselves at .95, when they clearly didn’t do the work they said they would do; and the folks who have nailed all but one of their key results, but still feel horrible that they left anything undone. There is no right way to do this, but an engaged manager learns so much from discussing output in a framework with their employees. Too few do this, but there is no better recipe for helping someone be successful in their career than setting clear goals and helping them make progress against them to drive the objectives of the company.

Corporate-wide OKRs also help everyone see that the enemy is outside the walls, and not within. So often in my career I have seen different teams fighting over headcount or budget, but when leadership is clear about the priorities and goals, and there is transparency and visibility in who is doing what and the dependencies on each other, THAT is when I’ve seen leaders say “don’t fund me until you fund that team; I won’t have anything to do/scale/sell/etc.” Ultimately leadership is not just about vision, it is about execution, and ensuring folks execute collectively means aligning on what success looks like, and then enabling each other to get there. This book is a great reminder (even if a little light on the how-tos). Definitely read all the way to the resource section at the end with the how-tos from Google. That is the most concrete “how to do it”, and know you will have to iterate. No one company does OKRs in the same way.

For October’s Book Club session we read Leadership and the New Science by Margaret Wheatley. This book felt more like a metaphor than a guide. Dr. Wheatley pokes at what is wrong with the traditional 19th century leadership mindset (hierarchical in nature, where the organization runs best in an autocratic fashion–think Henry Ford and factories where every person performed a specific physical function in the line). She uses Newtonian dynamics to describe both why we are inclined to believe this is “the way”, but also what we have learned about how the world functions at the subatomic level invalidating this approach. The heart of her argument is that as descriptive and measurable as these kinds of cause and effect relationships are for describing the dynamics of large objects, it isn’t actually how humans, relationships, or organizations function.

Dr. Wheatley draws analogies between “new science” (chaos theory, quantum physics, and deeper understanding of biology) and organizational dynamics. In many ways we are chaotic, but our chaos is actually a path to self-organization, and her postulate is chaos is actually how we maximize creativity, learning, and fundamentally innovation. Chaos Theory is derived from the discoveries of “strange attractors” and fractals. “Strange attractors” prove that amidst seeming chaos and randomness, patterns evolve revealing an order that is at work in the universe. This evolution is non-linear which means that the slightest variation in the inputs can result in vastly different outputs. Applying this to organizations implies organizational behavior can be unpredictable (which anyone who has lived through change management knows).

On the other hand, fractals prove that the same simple pattern can be found repeated at many levels of observation forming an intricate object when viewed as a whole. Wheatley draws the analogy between an organization’s culture and fractals implying that “simply expressed expectations of purpose, intent, and values, and the freedom for responsible individuals to make sense of these in their own way” will enable individuals to self-organize without strict enforcement, and in fact that will be more predictable than a “structured” approach, since it is fundamentally how we all work. My engineering mind has a hard time believing values alone will enable self-organization, but I have definitely seen how clear goals with transparency around the measured results can rally people to a cause more effectively than tops-down micromanagement. Align with the team on what success looks like, and how we will measure; then see them execute.

One of my favorite sections was on Quantum Physics and its applicability to organizational dynamics. The analogy here is between humans and subatomic interactions “…no particle can be drawn independent from others (p. 34)” and “what is critical is the relationship created between two or more elements. Systems influence individuals, and individuals call forth systems (p.36).” This feels incredibly true in my observations. How someone shows up in a meeting depends on who else is present, and how that individual relates to those others. We are points on a wave, not individuals fixed in time and space. I have seen how teams can overdeliver (or under) relative to their intellectual capacity based entirely on the relationships between the individuals and their partners and customers. Our relative position is what matters most.

This book is an alternate paradigm to describe work and human relationships, and it is in no way a guidebook for managers. As such, I found myself seeing these analogies across work and life at every turn, but in no way felt clearer on how to execute effectively in that world. Sometimes uncertainty is the kind of discomfort that drives insight and breakthroughs. Nearly everyone in the book club enjoyed this book, and felt similarly around its lack of direct applicability, but beauty in terms of insight. I definitely recommend this book philosophically to question your assumptions about life and work. It reminds me of one of my favorite quotations from one of my favorite books of all time “Live the questions now. Perhaps then, someday far in the future, you will gradually, without even noticing it, live your way into the answer,” – Rainer Maria Rilke

For book club in September we read Quiet: The Power of Introverts in a World that Can’t Stop Talking by Susan Cain. I found that I got a lot out of this book. I self-identify as “extroverted for a purpose”: being around people doesn’t exhaust me, except if I’m around people without purpose or authenticity; when I have to assume a role rather than be myself, I find that exhausting. I also absolutely recharge through running, reading a book, and quality time with one person or small familiar groups (which is more synonymous with introversion according to Cain’s definition). I enjoy people, and I can be energized by being around them with the right motivation and purpose (a work event with meaningful connection time, working through major challenges in a group, discussing a book with others to see multiple perspectives, etc.), but walking into a party without a purpose (just a casual thing or networking event just to “meet people”) feels…awkward to me.

The book talks about many aspects of introversion and extroversion. The key domains the books delves into are: how introverts and extroverts tend to differ around motivation and sensitivity, the impact of nature vs. nurture with respect to introversion and extroversion, Western vs. Eastern cultural norms on extroversion and introversion, the history of extroversion, how introverts may enact purposeful behavior changes to simulate extroversion, advice for corporations on how to grow and nurture introverts as well as extroverts, how leaders can embrace the diverse perspectives that groups with introverts and extroverts provide, and that introverts and extroverts benefit most when they cooperate. Fundamentally the book encourages understanding differences of human reactions to particular stimulus, and encourages empathy for those which may not reflect your cultural norm, but are still quite normal.

In terms of feedback, most of the book club enjoyed this book. We self-identified as half introverts and half extroverts in the group. Unilaterally the extroverts said they felt that their empathy and understanding for introverts expanded through the book. There was feedback on whether the inverse was true given the pathologically extroverted examples that were referenced in the book (e.g. Tony Robbins, Winston Churchill, etc.). The feeling was that the intention was to shun extroverts into “checking themselves” vs. helping people gain a better understanding of alternate mental states.

Ultimately I would have loved to see the conclusion own the oversimplification in the title and reiterate the nuance in the research cited throughout the book. There is a spectrum between introversion, ambiversion, and extroversion; stimulus, purpose, and environment alter how people manifest, and your upbringing and culture have a significant implication to how you will represent yourself. We are individuals, and we get to choose how we show up. I really enjoyed the messages around empathy and inclusion in this book, and wished there had been more moderate examples of extroverts to highlight that not all the good ones are introverts masquerading as extroverts because of Western society’s expectations and cultural norms, but even with that caveat I really did appreciate the book.

For book club this month we read Technopoly: The Surrender of Culture to Technology, which I have to admit was hard at times to read as a technophile. Still, sometimes the best books are the ones that force you to question your assumptions (and our book club selects books by popular vote), so I dug in.

First off I will say most of the folks in our club did not like the book: struggled with determining what the thesis was, and even if they resonated with a point here or there, it didn’t feel actionable. I will attempt to summarize the thesis I took away: part of what makes us human is lost as we become a more processed, controlled, technology-driven culture. The tradeoff is real, and he illustrates many things that change with new technology (religion, family, culture, politics, medicine, etc.) but he juxtaposes this as always negative, rather than just different, and that is where most of us, as a book club full of technologists, struggled. Just because new technology is invented doesn’t necessarily imply that society is net better or worse. Yes, it changes how society approaches something: if you always had to visit your family to connect with them and now you can do it on the phone or via text, is that really worse? Yes, the quality of the connection may not be as strong, but the frequency even as people have had to move farther from one another feels like a reasonable tradeoff to stay connected than just growing apart. Infant mortality being reduced through vaccination…these are just a few examples where it is clear that technology is net beneficial. Fundamentally change shouldn’t be seen as a zero sum game.

Still, I actually really enjoyed the book, not for the anti-technology bent, but because I resonated with one key premise: bias towards belief without knowledge and context leads to chaos, and we have to build educational systems, and norms that ensure we don’t fall into that trap. This line of thought is prescient in my mind given what we are seeing with ChatGPT and LLMs. Fundamentally these tools give definitive, and sometimes very wrong answers, and people believe them because of the form they take. In the book Postman talks about Eliza, an AI project that responded in the forms humans expected (as a teacher, therapist, etc.) and how in a study the humans reacted as if Eliza were in fact a real person when in reality it was just AI. This was done as an experiment, but fundamentally we are living this daily with our LLMs. If we don’t teach the humans interpreting the output a framework for critical thinking, then we will double down on the kind of bias/echo chamber that social media helped sew.

For Book Club this month we read Give and Take: A Revolutionary Approach to Success. In this book, Adam Grant categorizes people into three types: givers, matchers, and takers. Givers proactively help others, matchers try to give exactly as much as they get, and takers attempt to get more than they give, believing that this is required to be successful. Grant writes about the advantages and disadvantages of adopting a giving “reciprocity style” in the workplace, and highlights that givers can be both the most and least successful with data; the primary difference between successful and unsuccessful givers is knowing how to establish boundaries.

It was an interesting discussion at book club. Everyone enjoyed the book, either as a reflection to understand one’s personal style and whether or not we consistently show up that way in all contexts, or as a way to think through strategies when you are confronted with a person who isn’t matching your reciprocity style. The examples are clear in the book: people who accomplish great things can be all styles across any profession (Frank Lloyd Wright and Jonas Salk are examples of takers who met with great success in architecture and science respectively, and Adam Rifkin and Abraham Lincoln are given as examples of givers who met with great success in fields of entrepreneurship and politics), but he makes the case that givers are the MOST successful based on several studies in the long run. Fundamentally, we all appreciated a world view in which the “good guy” wins in the end.

If there is any critique I would personally give this book it is two-fold:

1. The classifications of styles are singular and ascribed to the individual vs. the context, and that has not been my personal experience. I have met many people who are givers at home, but not in the workplace, and arguably it is the culture of the workplace that leads to their choices in this matter. A company who celebrates giving back (in the form of mentorship, sponsorship, industry contributions, etc.) nurtures a culture of “give as much as we can give without hurting the business” vs. a “take more than you give” approach. That percolates into every decision one’s employees take, and how they interact with one another–the best in people will come out if you reward it. If you work at a company with a “winner takes all” business mindset, I have seen that trickle into who gets promoted/recognized/etc. and in those companies a giver will struggle to succeed.

I honestly believe most people want to give to others (and Grant also calls this out in the book), but they have to feel that they can, and companies/leaders/managers can do a lot to foster that kind of community and trust. Grant focuses on the individual as if this is entirely their choice and control, and doesn’t tackle the systems which contribute. That notion clashes with my world view that people are usually good, and systems create the majority of the bad behavior. I appreciate the individualism in his approach, but I think we as leaders need to tackle our systems for rewards in order to ensure that we are cultivating environments to enable people to work best together.

2. All of the givers, takers, and matchers given as examples in the book are men of European descent. I can see two reasons for this: one, Grant is trying to normalize the data and therefore stick with one “type”; two, there is bias in the historical record making it harder to discern a consistent signal on female and minority figures of the past.

In book club I brought up the observation that there were no female examples in the book. It was a difficult conversation: bias is a touchy subject, and I almost felt bad mentioning it, yet it stood out to me that there wasn’t an account of a woman in the entire book who was noted as a giver, taker, or matcher. Research done by women and underrepresented minorities was cited, so I don’t believe this speaks to Grant’s bias against people, but rather the possibilities above: this was a conscious decision to normalize, or he felt there wasn’t enough historical information to make a strong conclusion.

It was interesting to me that no one else noticed this (indicates that I might be over-sensitive), and that the response to me bringing it up led to a discussion about safety to have difficult conversations, and even the concept of meta conversation (discussions about discussions rather than the actual topic) in order to align upon how we would approach this observation. (Aside: I love that this little community we have built will delve into the concept of meta communications to frame a discussion and then dive in!)

We did have a short conversation about the observation (our time was running out), and the conclusion was that there are gendered norms around reciprocity, and there are gendered expectations around communication styles, but delving into those would be a different book. Examples of books which attempt to tackle the research include Lean In: Women, Work, and the Will to Lead, You Just Don’t Understand: Women and Men in Conversation, and I’m sure more, so maybe this was indeed a conscious choice by Grant to stick to examples in one gender and race profile, which maybe could be applied to others, but he didn’t attempt to do so.

Within our book club we represent a wide array of races and genders and we all could think of examples of givers, takers, and matchers across all of these lines, so I believe Grant’s observations of types hold. What was less clear to us was whether or not his conclusion about givers being the most successful over time would hold. It is truly hard to say, and maybe should delve into a discussion about what success is (which often changes throughout one’s life)…that too is a different book (The Second Mountain, and Designing Your Life come to mind as books I really enjoyed tackling that realm).

Ultimately I like the notion of living in a world with Karma, and trying to give more than we get. Most situations are not “fixed pie” scenarios, and finding ways to reframe decisions into win-win situations has been one of the most important insights in my professional life. I really enjoyed the book and recommend it highly.

Happy Reading!

For June book club we read Brené Brown’s book Dare to Lead. Full disclosure: I had already read this book and really enjoyed it personally. I felt SEEN and really had to dig deep on two concepts:

1. Speaking about others when they are not in the room. There is a section where she mentions that in order to build trust, you should always bring issues TO someone and never speak about someone else without them in the room. I have always found this to be daunting. I like to believe I don’t gossip, but as a manager, often people bring personnel issues to me, and it is hard to discuss that without in some sense discussing the other person. I always seek to encourage direct dialogue with the party in question, but in order to coach I find myself sharing insights about my interactions with that person (trying to help them understand if that individual is biased to action and maybe that is why they came across as gruff, or more shy and reserved and so maybe they are not engaging yet, but will utilizing alternate media such as a blog or chat, etc.) I find this specific feedback hard to execute in practice, although I agree that the underlying concept (talking behind people’s backs) is unhelpful. I would just caveat that intention matters, and I hope if I share the intention behind the discussion then it will be ok to have these kinds of discussions, but I am far more deliberate about that framing than I used to be.

2. Showing sympathy vs. empathy. When I was going through the hardest part of last year (watching my nephew and my family suffer and not being able to do anything) I really got to see this in action. People, quite accidentally, often say “I’m sorry for your family” or “I’m sorry that your nephew has to go through this.” Fundamentally this is sympathy, and it is distancing–it separates you from the subject. Then there would be folks who said something more along the lines of, “Please take care of yourself. I remember when I was going through my father’s illness–it is a marathon and not a sprint. If there is anything I can do to help you or your family, please let me know.” Here that person was relating to my experience, and showing me they were there, holding my hand, willing to support me if they could. I had never learned these concepts in school (not really an engineering subject) or felt I necessarily needed them before last year, but after going through such an experience, I now know: be WITH people in their pain. There is no “right” thing to say, just show you are there to hold their hand, share a book on grief (that was incredibly thoughtful gift from a friend of mine), or just send a text checking in. I hope I will always show up for others this way after having been on the receiving end, and I’m sorry to all the friends/colleagues I may have accidentally isolated or made worse before I knew better.

Our book club session was lightly attended given the holiday in the US, but I was glad to have had the discussion with other folks in different phases of their careers and leadership journeys because I always learn something. Some of the feedback shared was that Dr. Brown’s colloquialisms were too outdated and/or “Southern” and were triggering/hard to relate to for that person since he came from the South himself. Many of us felt that she uses the term “rumble” a lot, and honestly outside a 1950s reference to car racing, it really isn’t a term I know or relate to very well. However, I can see where it could get triggering based on background, or just be difficult to relate to for someone earlier in their career journey or not from the US. I personally found her style charming and relatable, but not everyone has the same reaction to these sorts of things.

The other feedback was that she had a strong underlying principle for the book, but it was potentially redundant. Fundamentally the book’s premise is that being a good leader requires you to lean into your discomfort, have hard conversations, be vulnerable, authentic, and brave. There is a fair amount of repetitiveness of this theme throughout the book. I read that as reinforcement of the key concept through different stories/lenses, but if you prefer books with more brevity, I could see where that style might not appeal. There was actually the observation from one of our attendees that this almost felt like a set of essays rather than a book. Again, that was not how I read it, but I can see the perspective.

Something everyone really loved was distilling and sharing one’s core values. What are the one to two things that are core to who you are, and how can you ensure that the work in your life relates to those values? If you are clear about those values, can you share them with the folks you care about? If someone you work with has shared their values, do you find that making sense of their behavior and interactions is clearer? If we are honest about our core motivations and willing to share, then working together can become significantly easier. I personally value learning and people above everything. Note I use the word “people,” not community, purposefully. I value you, the individual, and I want to know you. I never want to know people solely through context (we work at the same company, our kids attend the same school, etc.) because then our brains use archetypes to generalize about the other person rather than really understanding who people are and what motivates them.

This set of values means I tend toward smaller groups: I like one-on-one discussions, and team-building is particularly important to me (grabbing a meal, taking a walk, going on a hike together, etc.) to establish trust with people. Anyone who knows me or has worked with me probably knows the learning piece–I love learning, and whenever I have successfully figured out how to frame an experience as a learning one, I have nearly infinite motivation to grind through it. Similarly, if the work is for a person I care about (be it a customer, partner, etc.), I can almost always make it happen, and if I cannot it is particularly hard for me. The heart of this exercise from Dr. Brown is to reflect on this about yourself, and share it with your team/teammates., so you find ways to work best together.

In general I’m a large fan of Dr. Brown and her books, and I personally enjoyed and recommend this book, but obviously the opinion is not universal.

For May book club we read the Principles of Life and Work by Ray Dalio. This book is DENSE, so only 2 of us actually finished the book (more than 50 folks are in our book club, although only 10-20 show up monthly), and usually 95% of folks finish the book, so this is fairly rare. That being said, I don’t think it was an indictment of the book so much as the topic is written with a lot of due diligence (a deeply data-driven approach to interpersonal topics), and can be a bit robotic if you don’t relate to a numerical analysis framework. Still there are incredibly good nuggets that came out, and are worth calling out:

1. Write down one’s principles. No one teaches you this, nor is this a typical phase of development in school, at home, or at work. Truly though, don’t you want to be clear about your values and principles? Won’t that help your spouse/partner, children, coworkers, etc. to know what you value, how you think, and therefore the best ways to interact with you? What a blessing to have that insight into another person so you can understand where they are coming from and how to approach a discussion, decision, etc. to help anchor the decision in what matters to them.
2. The concept of an “orchestrator” you vs. the “worker” you. Fundamentally this notion is that you must seek to understand what you are truly good at, and where you should delegate for the sake of the overall project/organization/team. Feedback in this is your greatest friend in this process, particularly negative feedback. NO ONE is good at everything. This truth is not something to bemoan or be ashamed. You have to seek to learn where “worker” you is not good, decide if you want to improve, or enable the “orchestrator” you to ensure that part of the work is with someone else. Ultimately, you own the outcomes of your career and life, and you need to approach it objectively to have excellent outcomes.
3. For a data-driven approach, he discusses the strength of computers and AI, but also the dangers. In a sense that AI will detect patterns, but there is more that goes into decision making than directing patterns–AI without human interpretation and/or validation only reinforces bias, and our goals for our organizations and decision making should be greater than that.

So since so few folks made it through the whole book, I decided to try to write a summary. The 5 Major Life Principles Mr. Dalio states are:

1. Embrace Reality and Deal with It
2. Use the 5-step-process to get what you want in life:
   1. Set clear, audacious goals
   2. Don’t tolerate problems
   3. Diagnose the root causes
   4. Design a plan before you act 
   5. Execute to completion
3. Be radically open-minded
4. Understand how people are wired differently
5. Learn to make decisions effectively

His major work principles fall into similar themes:

1. Build a great team:
   1. Focus on great people 
   2. Build a great culture
   3. Create the machines to ensure your outcomes consistently match your goals 
   4. Align your work with your passions
   5. Do it with people you want to build a future with
2. Get the culture right by surfacing and resolving disagreements
   1. Radical Truth and Radical Transparency
   2. Nurturing Meaningful Work and Meaningful Relationships
   3. Making it a cultural norm to learn from mistakes
   4. Getting people in sync
   5. Using Believability-Weighted Decision-Making
   6. Having an agreed resolution process
3. Get the people right
   1. Put WHO before WHAT
   2. Hire right
   3. Fit the right people into your organizational design by continually training, testing, evaluating and sorting them
4. Build and evolve your machine:
   1. Running your machine as a manager/designer
   2. Not tolerating problems
   3. Diagnosing problems root causes
   4. Continually improving your machine design 
   5. Executing your plans
   6. Using tools and protocols to shape habits, and 
   7. Paying attention to governance

These concepts are simple to write down (it is what makes them so compelling), but are actually hard to execute (which is what makes the book long/detailed). I think believability-weighted decision making seemed difficult to institute culturally (but then again, we all have bias and are bringing it to work anyway, so why not be explicit about the reasons for weighting one person’s input differentially).

I highly recommend this book, as much as an exercise in how to approach an analytical person on the topics of culture, leadership, principles, and values, as for one’s own introspection. You will definitely learn something.