Categories
Foundational Values Vulnerability

Hey, What’s Your Angle?

For the very first blog post here, I want to address my motivation.

A good friend of mine recently shared:

“I have always feared executives. They always have an agenda and they have the power to hurt me. I have trusted very few executives in my career.”

Can you relate to that?

If you are an executive or a manager of any kind, there is authority baked into your role, and that very authority all-too-easily gets in the way of our human relationships. People are conditioned to follow people in positions of labeled authority, whether it is in their best interest or not. While it is one thing to be followed, it is an entirely different thing to be trusted. Early on in our journey on The Progressive CIO, it bears noting that this dynamic will be at the very heart of our discussions.

The notion of vulnerability is something that springs to mind, and there is a reason that I list it first on the values that you see on this site.

We are born vulnerable, and if we are lucky enough to grow past childhood into adulthood, it is our very vulnerability that encourages others to protect us, to guide us, and to groom us.

As adults, when we see a young adult, our minds seem to appreciate the independence of the creature who stands before us. We do not attempt to steer or offer guidance to that person in the same way we would an infant. You must recall the feelings you sometimes have when you speak with young adults who think they “know it all” — you know that nothing you could offer will give them what time and experience will.

As we grow, others around us are much less likely to guide us in the way we were when we were young…when we were vulnerable.

But if we can show vulnerability to others as adults — as leaders — something remarkable happens. If I say to someone:

I am afraid of something.
I am lacking something.
I need help with something.
I am sad about something.
I am confused about something.

…what happens? Others are more likely to step in to help me and to guide me, and I stand a much better chance of learning something as a result. Why is that? Because humans are so well-conditioned to help others who are willing to show vulnerability and ask for help. It is immediately relatable, because inside, we are all filled with doubts. We too often hide those doubts in the interest of looking confident. But that gets us absolutely nowhere good and is, in fact, the ultimate manifestation of the lack of true self-confidence.

Truly self-confident people know who they are inside. They can admit when they do not know something because they are not ashamed of it. Most importantly, they know that if they expose those vulnerabilities, they are much more likely to learn and grow through the help of others.

The fear of executives — of anybody in a position of authority — has a clear mitigation strategy for those who are feared: Develop the ability to show vulnerability at the times you are feeling vulnerable. You will help others to do the same, it will be easier for others to come to trust you, and you will see remarkable results in your teams, from those who elicit software requirements to those who provide help desk support. You will spark a chain reaction that will bring joy to those who you serve. We’ll talk in great depth about this in posts to come.

My angle for The Progressive CIO is to provide thoughtful discussions in print form that can be shared, digested, and considered by teams of technology leaders as they face their own challenges. The goal is to build a central repository of information that is easily available to help foster what I believe is a more rewarding approach to technology leadership.

Any questions?

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🎹 Music for this post: https://www.youtube.com/watch?v=r7etn2czISU

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Categories
Humility Vulnerability

We’re All Impostors

Thanks go to my brother Rich for sending this Guardian article to me, allowing me to share a final thought for this very long year:

Some pretty smart women claim to be racked by impostor syndrome. Do men just not get it?

The headline asks an interesting question, and I have an educated, but admittedly unscientific, answer: yes, men “get” impostor syndrome. All the time.

What Catherine Bennett describes as “the association of authority with traditionally male exhibitions of extreme assurance” is, from my perspective, the defining mark of a deeply-buried case of male impostor syndrome.

What does true self-confidence look like?

Is it the way that Donald Trump or Boris Johnson or David Cameron or Vladimir Putin behave?

Conversely, what about when Ronald Reagan admitted his mistakes in the Iran-Contra scandal? Or when George H. W. Bush apologized for raising taxes? Or when John F. Kennedy took responsibility for the Bay of Pigs invasion?

Are those illustrations of weakness, or of strength?

Friends, true self-confidence is marked by the ability to openly admit mistakes or lack of knowledge…true self-confidence is all about vulnerability and humility.

Why might you not want to admit mistakes? Do you feel that it might amplify a certain lack of ability, and that others might think less of you? Both of these are strong indicators of personal insecurity. If you are afraid to admit mistakes, you are, by definition, afraid of people knowing your weaknesses. All signs point to some amount of impostor syndrome at this point.

The difference between female and male instances of impostor syndrome, I think, is that women seem to feel more comfortable exploring their weaknesses at a liminal level than men do. Men instead tend to pelt their insecurities down into subliminal territory, creating strong compensating facades of synthesized self-confidence, perhaps powered through the unique delusion of testosterone.

What man (or woman) who cannot admit mistakes and take corrective actions does so for any reason other than fear?

And what could that man or woman be afraid of, other than people beginning to see chinks in their armor?

As I have gotten older, I have developed a belief that most people lack self-confidence for some portion — maybe even a large portion — of their lives. Most people (including yours truly!) become aware of their relative lack of significance in the universe through some lonely moments of self-reflection, and they build up ugly behaviors in order to compensate for this. Ironically, it is the very ability for so many people around us to successfully fake self-confidence through “brio,” to borrow Boris Johnson’s term, that we find the seedlings of self-doubt so deeply sown in ourselves.

If our default human tendency was to openly embrace and exhibit our faults — with confidence! — the world might be a very different place, don’t you think?

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🎹 Music for this post: https://www.youtube.com/watch?v=B9dSYgd5Elk.

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Categories
Antipatterns Compassion Invisibleism Vulnerability

Revisiting Patrick Lencioni’s First Team: It’s a Fractal!

As I’ve mentioned before, I’m not an avid reader of business nonfiction bestsellers. Books that have been foundational to my thinking have been at least somewhat academic (and unfortunately esoteric) in nature, like Aristotle’s Rhetoric and Kenneth Burke’s Language as Symbolic Action. If you’ve been following me on these pages, though, you know that I delight in citing two books that are straightforward yet uncommonly seen in offices around the world. There is, however, a third approachable book that I am fond of, which you might have read before, since it is comparatively well-known. That book, nearing its 20th birthday, is Patrick Lencioni’s The Five Dysfunctions of a Team.

As with all things popular, critiques of Five Dysfunctions are in no short supply. The book’s Wikipedia entry does its job on this, citing some thoughtful summary criticism, noting that the “book is explicitly a work of fiction; it is not based on research and its practical recommendations lack empirical support.” There is truth to that, but if you have been following me on these pages, you will remember that I have a firm belief that truth is best derived from considering multiple perspectives over time. The many sorts of responses to Five Dysfunctions that have been penned over the years have brought helpful real-world framing to the book’s core concepts, adding value through a globally-shared dialog.

Here is yet another response, albeit one that I hope you find to be new and refreshing.


Like seemingly everything else from Five Dysfunctions, the “First Team” concept has been through the point-counterpoint wringer over the past two decades. If the “First Team” concept is unfamiliar to you, then let’s listen to Patrick Lencioni himself introduce it:

I’d like to suggest that, rather than eschewing ideas (such as this one!) that might not be strictly empirical, we consider them, at the very least, to be valuable thought exercises.

I am fond of the “First Team” thought exercise. Why? Well, I have been part of no fewer than five senior management teams in my career, and each one of those teams was at its weakest when we were not attendant to one another, and when we spent the majority of our time in our vertical silos. We were not as strategic, and our teams were not as tightly focused on the company’s mission, when we were more attendant to our departments than to senior teams. Anecdotal? Perhaps. But at the very least, I have developed an opinion that the “First Team” is worth talking about from time to time, wherever you may work.

A “First Team” Thought Exercise Extension, in Two Parts

Part The First

Whether we like it or not, our jobs are at least somewhat framed by our titles, whose primary purpose is, more or less, to denote our roles. These titles, apart from “President” and “CEO,” always connote some form of swim lane that we work within.

New-age management philosophies like Teal and Holacracy aim to reduce the significance of titles in an effort to encourage an organization’s members to better appreciate (and contribute to solving) the many challenges that exist across its functions. However, these management styles present their own challenges. First off, they are wholly unfamiliar to the majority of the working population. More notably, however, in accordance with the valiant mission to decentralize power and decision making, they sometimes confuse people who feel uncomfortable making certain types of decisions, and who would better serve an organization when given at least some amount of explicit direction. Human beings are animals (which we too often forget), and animals are conditioned to exist within a power structure, whether we like that or not.

This is not to say that Holacracy or Teal are unworthy of further work and refinement; they most certainly are. What’s more effective to say is: work is not what we want to do in comparison to the better parts of life (if it were, we wouldn’t get paid for it), and doing what we can to help it be less of a drag will vastly increase the likelihood that our employees will stay with us to solve the problems we are paid to solve. One thing that seems to resonate with all workers is when power structures are absent enough to allow people to breathe and bring their own values to the table, yet present enough to provide clear direction when needed.

All of this is to suggest that there is a desirable balance between power presence and power absence, and that power absence is something that needs focus, since it is not as natural as power presence. The “First Team” thought exercise is most useful, in my opinion, in helping organizations find that better balance. That’s because, when we encourage a First Team mentality, we have to work hard ensure that the teams of people who report into the First Team have healthy team dynamics of their own. More on that in a bit.

I think teams struggle to identify when it’s time to engage further with the “First Team” thought exercise, to calibrate their work toward its prescribed dynamic. Here are six questions that will help you know:

  1. Are the team members aware of each other’s professional issues, and are they willing to spend the time to contribute to each other’s success in overcoming those issues?
  2. Are the team members aware of each other’s personal issues, to the extent necessary to help others empathize with their challenges meeting professional expectations?
  3. In the spirit of invisibleism, are all team members paying attention not only to what they see, but what they do not see?
  4. Do the team members have a rapport that allows for vulnerability on a routine basis, wherein a team member can openly share a personal deficiency or fear without reprisal, and with compassion?
  5. Does any member of the team feel that it’s a “drag” to spend time with their “First Team” when compared to spending time with the team who reports into them, or with their customers/stakeholders?
  6. Are there “factions” within the team that draw a subset of the team together more powerfully than the entire team is drawn to itself?

If you can answer yes to any of these six questions, it’s time to recalibrate your First Team dynamic.

It’s entirely possible for the First Team concept to go too far. That is easier to identify through these two anti-patterns:

  1. When the team too often feels like an “escape” from the difficult work any of its members have to do, and First Team members abandon their responsibilities to their Second Teams.
  2. When (you are lucky enough to hear grumblings that) the team is a “clique” who merely likes to enjoy lunching and drinking together, and is inaccessible to outsiders.

Remember, this is all about balance.

Part The Second

Sometimes the best way to see where you are is through triangulation.

In this case, let’s consider what all of the above means to the team of people who report into you, who students of Lencioni might call your “Second Team.”

As a leader for your Second Team, you would do well to encourage them to be a First Team unto themselves (and I do mean that they, without you, comprise this First Team). Despite all that has been written about Patrick Lencioni and his work over the years, this is not a conclusion that most people seem to draw, yet I suggest that this is, in fact, your most important responsibility as your Second Team’s leader.

In other words, don’t limit the “First Team” thought exercise to your executive team. Understand that it is fractal in nature, and you would do well to encourage it wherever you find leadership groups in your organization. Wherever a First Team exists, the Second Team will need to be able to better self-manage when their leader needs to tend to his or her First Team needs, and the First Team thought exercise will be especially valuable to prepare that Second Team for those moments.

Are you creating an environment where your Second Team can answer “yes” to the six questions above, while avoiding the two anti-patterns?

If so, then congratulations.

If both your First Team and Second Team are exhibiting the optimum balance, then hats off to you: it’s time for a well-deserved, relaxing vacation.

But we are imperfect creatures, living in an imperfect world. Most of the time, we will find ourselves working on maintaining the right balance between nurturing our First Team while helping our Second Team nurture its own First Team dynamic.

Remember: what we are looking to achieve, in the end, is an appropriate balance at any given moment between power presence and power absence for the people who are looking to us for leadership. If your Second Team is able to be its own First Team, then step away and work on your First Team. If your First Team and Second Team are both having problems, do not focus on your Second Team at the expense of your First Team, but don’t walk away from them, either. Seek to help your Second Team regain its balance while you remind them that your First Team needs balancing, too. Make the balance part of the conversations you have with both of your teams.

But keep a close eye on anti-pattern #1. None of the above is to suggest that your Second Team should ever feel like they have been abandoned by you. They deserve your leadership. Power abhors a vacuum, and our animalistic conditioning for leadership structures will ensure that your unofficial replacement is eventually found. That would be a tragedy for your team.

The “First Team” is a handy tool. It is a fulcrum for introspection, and it can help you achieve the some of the best elements of Teal and Holacracy without completely reinventing your organization. Keep it in a front pocket, use it often, and don’t neglect your duty to pay it forward to the teams you lead. It’s good for them today, and should you depart — whether through attrition, retirement, or otherwise — it will condition your organization for smoother succession tomorrow.

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🎹 Music for this post: https://www.youtube.com/watch?v=QSUD7WHzFTw.

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Categories
Commitment Compassion Curiosity Current Events: 2021 Empathy Humility Patience Vulnerability Willingness

Fixing Today’s Workplace Requires Packing Up Our Politics

Taking a look today (December 6th, 2021) at the New York Times Hardcover Nonfiction bestseller list, I see:

  1. History (THE 1619 PROJECT)
  2. Biography/Entertainment (WILL)
  3. Biography/Entertainment (THE LYRICS: 1956 TO THE PRESENT)
  4. Biography/Entertainment (THE STORYTELLER)
  5. Holiday (ALL AMERICAN CHRISTMAS)
  6. Entertainment / Food (TASTE)
  7. Personal stories (THESE PRECIOUS DAYS)
  8. Biography/Medicine (THE REAL ANTHONY FAUCI)
  9. History (THE PRESIDENT AND THE FREEDOM FIGHTER)
  10. Biography/Entertainment (THE BEATLES: GET BACK)

Compare that to two years ago at this time:

  1. Politics (A WARNING)
  2. Politics (TRIGGERED)
  3. Entertainment (ME)
  4. Politics (BECOMING)
  5. History (SAM HOUSTON AND THE ALAMO AVENGERS)
  6. Communication (TALKING TO STRANGERS)
  7. Personal stories (FINDING CHIKA)
  8. Personal stories (EDUCATED)
  9. Biology (THE BODY)
  10. Politics (WITH ALL DUE RESPECT)

Those differences are telling. Two years ago, post-election, with our cold civil war a-brewing, politics was our fascination. Today, we are weary for just about anything other than entertainment. Our brains and our souls need a rest and a reset.

Interest in work-related topics is also in an ebb cycle. People are not in the mood to read books, columns, or blogs that consist of generalized advice aimed at improving their work lives. I suspect people realize that questions about what’s truly going on right now in the workforce have no easy answers. What’s truly going on is that our cold civil war has bled into our work life.

The Progressive CIO was borne out of my epiphanies in the wake of COVID-19 — a long and turbulent wake that we are still navigating. My writings have reflected my work and encounters along the way. In recent months, however, I’ve slowed. I have nothing to offer that I think can address our cold civil war, and writing more about the eight foundational values of The Progressive CIO seems tone-deaf at the moment. While those values are — and always will be — important, getting back to considering them will require navigating out of our current wake, which requires addressing politics.

We’re not supposed to have politics in our workplaces, though, right? As it turns out, it’s too late for that. As we attempt to return to offices, COVID has brought politics into the workplace as never before, for a simple reason: the semiotics of the face covering.

I cannot think of any symbol in the workplace — or in everyday life — that has communicated a political stance so overtly in my lifetime as the manner in which face coverings are (or are not) worn. This is not to say that wearing a face covering or not is, unto itself, a form of political expression. As with a tree falling in the forest, it’s the junction of the act and the audience where meaning takes shape.

Take a look at these four different face-covering scenarios, and reflect on what they say to you:

At least one of those will strike a nerve within you, wherever you sit on the political spectrum.

Semiotics are a part of everyday communication and everyday life. Face coverings fall into the non-language communication subset of semiotics, which are distinct from the more-commonly-encountered non-verbal communication. Non-verbal communication involves a language; that is to say, a system of communication with a learned form and structure. Music is a language, for instance. Non-language communication, on the other hand, lacks any system or learned form and structure. Lines on our roads are non-verbal communication; a driver swerving around those lines is non-language communication.

Non-language communication isn’t discussed much outside of academic circles. If it were, I suppose we might have a better public dialog about face covering techniques. I suspect, however, that it wouldn’t have an impact on our current cold civil war at work. Whether we like it or not, masks have become a form of wearing one’s politics on one’s face. The bigger issue is that non-language communication, through its very nature, makes verbal analysis more challenging.

At the present, only fully-distributed workforces are in a position to avoid face covering controversies in daily work life. We know, however, that not all workforces can be fully-distributed.

Proposed vaccination and testing rules are about to increase the magnitude of the COVID-19 wake, before the current tide has finished going out. How a company reacts to and addresses these rules puts politics on a company’s face as well.

When we are in a place where we know the solution is: “Take politics out of the workplace” and those politics are now a way of life as a matter of public health, then where does that leave us?

It leaves us doing our jobs and trying not to think about them when we don’t have to. It leaves us tired of politics, even if we are energized by them. (Which leaves me to ponder: If one is energized by politics, then what does that say about that person and their priorities?) It leaves us retreating to our homes, our families, entertainment, and the things that truly matter in life. That’s not all a bad thing. But if our lives require us to work, we’re all in a pickle for the time being.

Back to those eight foundational values of The Progressive CIO: I would be remiss if I didn’t take a moment to reflect on them, and how they play a role in getting ourselves out of our current situation:

Vulnerability: Are we willing to be honest and open with one another about how our current world is affecting us? This will include senior leaders acknowledging that these vulnerable voices need to be heard.

Humility: Are we willing to recognize that this situation is bigger than all of us, and that it is a comedy of errors, of sorts, if not a true human tragedy? It’s difficult to laugh at, but I believe we have to if we are to collectively solve it.

Empathy: No matter your politics or attitude, will you try as hard as you can to see the validity in the other side’s point of view? This doesn’t mean that you agree that the other side is right; it merely means that you work hard enough to try to understand and not summarily dismiss.

Patience: This might be the hardest thing of all. People were tired of not getting their hair colored one month into the pandemic. Do we have the collective patience to deal with one another to move past where we are today? We don’t have a choice, because it will be a long haul. If we can acknowledge this, we stand a chance to get a clearer understanding of what the path to progress looks like.

Compassion: Do we genuinely care about each other, to the extent we are willing to go out of our way to bring comfort to others?

Curiosity: Are we willing to explore the new and unseen options that we have not yet explored to get us past where we are today?

Commitment: Are we willing to make true commitments to one another, and follow through on those commitments?

Willingness: Do we have genuine willingness to do all of the hard work above?

Given how tired we all remain, who can we expect to initiate this sort of effort on a meaningful scale?

Only those who govern us.

I’m not talking about legislation; I’m talking about leading by example, living those eight values. If that sounds like a tall order, it most certainly is. That’s because there is a chasm between politics and governance. The government I am alluding to does not exist today, and has probably not existed in our lifetimes. Until we can pack up our politics, no governing will happen. Until we can pack up our politics, no leadership will happen. Until we can pack up our politics, our workplaces will not flourish. Until we can pack up our politics, the world will not be the place we want it to be. The good news? Packing up our politics starts, apparently, with the books we buy.

Postscript

A friend shared the following response:

I loved your start – the comparison of the top books is quite telling, and I would not have thought to make that comparison. I am right there with you throughout your article until the end. Who should or will initiate these changes? For me it’s all of us, it’s the workers, it’s the everyday people in the workplace, it’s you and it’s me. I think we can be sure right now our leaders are quite absent, especially those who govern.

One of my favorite quotes I encountered along the way of my doctoral studies comes from Ralph Stacey, “Change can only happen in many, many local interactions.” For me, this means it is in the small conversations that spark other conversations and so on that we begin to change culture, that we begin to change each other. I is in those times of making space and being vulnerable that we listen to others and that we speak our truth. In those moments one or the other or both are truly changed, and that sparks a change in the next conversation that we have. For me, it is in this process that true change happens. Not in the top down, governed-inspired or directed change.

But that’s me, and perhaps I am missing some of what you are concluding or alluding to.

I agree with this in spirit—and I had wanted to end with this sentiment. But after reviewing the how the foundational values might address this, and pondering how realistic this would be, I felt this conclusion would sound trite. There is a realist at work in my brain right now. This sort of change benefits from top-down work of unimaginable magnitude. Imagine the impact our governing bodies could have if they demonstrated these values in their everyday actions!

In the “DVD bonus feature” spirit of allowing you to choose your own ending, I encourage you to do just that with this post. I would love nothing more than for everyday people—rather than government—to achieve this change.

In the end, if this post merely encourages discussion, then it will have served a purpose.

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🎹 Music for this post: https://www.youtube.com/watch?v=H-kA3UtBj4M.

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Categories
Commitment Compassion Empathy Humility Invisibleism Patience Vulnerability Willingness

Look Up

When you get to know someone, do you focus more on what’s wrong with them, or what’s right with them?

Is there a benefit to focusing on one or the other?

How do you feel about your own flaws? Do you admit them, or do you try to hide them or compensate for them?

Why do you think that’s the case?

When I was a young executive, my boss once shared the following pearl of wisdom with me…it’s explicit, but this is the way I learned it:

If you look up someone’s ass, you’re always going to find shit.

—H. Eliot Subin

Every one of us has something that, once discovered, will be off-putting to others. If we look hard for these things, we are certain to eventually find them.

When we find someone else’s poop — knowing that we each have our own — why does that so often surprise us, and make us think differently about them? Perhaps because most people like to like people. When we get to know a person and we like that person, it brings us joy; it makes us feel like the world is a better place. We like the honeymoon period, before we find the poop. We like the Hallmark Channel.

When we discover flaws in people, it’s all too easy to feel let down. But it’s a terrible mistake to dismiss someone else when we discover their poop. How would you feel if the shoe were on the other foot?


If you’ve been in business long enough, you’ve undoubtedly been asked about the leaders who have inspired you on your journey. For me, the most immediate answer has long been George Martin. He’s an admittedly unusual choice. I’m a lifelong Beatles fan, and while I love the Beatles’ music, I find their group dynamic even more intriguing.

The Beatles were four young men who loved music, and who had a deep appreciation for one another. But despite a few friendly and intense years in the early half of their career, they were decidedly not in love with one another. In fact, their creative peak paralleled their social nadir. They had different values in life and in their music. They worked hard to keep themselves together in the way the world expected, and George Martin’s greatest contributions were in providing musical balance to complement their competing ideas. Watching his deft, delicate, minimalist hand at work in Peter Jackson’s recent Get Back documentary series is a powerful illustration of this. As their closest colleague in the studio, he routinely mediated compromise, helping four very different people become something much greater than they were individually.

At this point, it feels appropriate to revisit the quote from Victor Hugo on The Progressive CIO’s home page, which presaged this very post two years ago:

“But who among us is perfect? Even the greatest strategists have their eclipses, and the greatest blunders, like the thickest ropes, are often compounded of a multitude of strands. Take the rope apart, separate it into the small threads that compose it, and you can break them one by one. You think, ‘That is all there was!’ But twist them all together and you have something tremendous.”

—Victor Hugo, Les Misérables

If you lead teams of talented and smart people, they will have differences with one another — sometimes significant ones. They will find things to dislike in each other’s philosophies, politics, lifestyles, or approaches. It is your ability to embrace, cultivate, coach through, and complement these differences that paves the road from disaster to brilliance. What does it take for you to develop a deft and delicate hand to manage this?

First: Never forget your own flaws. This requires humility.

Second: Get comfortable talking about those flaws, which will be reassuring to those who you serve and who you lead. This requires vulnerability.

Third: Develop an ability to not be surprised or disappointed when you find flaws in others. In conjunction, develop the ability to lock, arm-in-arm, in your shared humanity, This requires compassion.

Fourth: Understand that what you perceive as a flaw might not be perceived that way by others. Try to look at this perceived flaw from different perspectives, and consider invisibleism along the way. This requires empathy.

Fifth: Learn to take a breath and stay calm when others find flaws and react in unbecoming ways. This requires patience.

Sixth: When walking through these concepts with someone who is struggling with what they have found: stop, smile, and share Eliot’s quote.

Then, explore the dialogue that opens this post. This requires willingness.

Finally: Teach these lessons forward.

Of course, there are limits that, from time to time, you will confront in managing this dynamic. The Tyranny of Competence comes to mind. The best way to address this, should you need to, is through compassion, and not through anger, remembering that we all have our flaws. This will give you the best shot at addressing difficult interpersonal situations before someone simply has to go.

I think many workplaces understand the need to manage differences; what differentiates the best ones is the way they manage the flaws we discover in one another. There will be failures. There will be break-ups. Even George Martin’s work couldn’t keep the Beatles together. But a great team’s finest work comes only with significant attention to managing their reactions to one another’s flaws, however ugly they may be.

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🎹 Music for this post: https://www.youtube.com/watch?v=H5ArpRWcGe0.

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