Category Archives: Leadership

Book Review: Ray Dalio’s Principles

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How to read it

I just finished Ray Dalio’s Principles and found the book to be both uneven and very useful.

Sometimes I’d read a few paragraphs and think “I should probably spend the next decade trying to get that right” and sometimes I’d read 10 pages and think “that’s a long way of saying something that everyone already knows.”

Thanks to Ken Bubp, our team is also digging into the book together, which I hope will make us better.

Already, there are a couple of areas where the book made me want to get much better – a few of those detailed below.

The point of a work conversations is to find the truth

The point of social conversation is not  to find the truth: it’s to build bonds, have fun, and play status games.

These social habits tend to bleed into work conversations and it takes a lot of deliberate effort to create an environment where truth seeking is the paramount goal of a conversation.

Specifically, truth finding conversations require the implementation of two difficult to reconcile mindsets: not holding tight too tight to one’s own opinions + being aggressive enough to pressure test another person’s opinions.

So team members have to constantly toggle between:

you’re a smart person who shares my values so I need to figure out why you think I’m wrong because I might be wrong

and

I think you’re wrong because of X and I will not back down from this opinion for the sake of being agreeable

This is tough to do.

Normalize and embrace emotional and intellectual pain

In social relationships, we tend to avoid pain. Doing so is often bad for the long-term health of social relationships, and it can be devastating in professional settings.

Too often in work:

  1. It is considered harmful to cause someone else intellectual or emotional pain.
  2. The first reaction of feeling pain is often to attack others and build self-promoting narratives.

Both of these are very hard to unwind.

It’s very difficult to create a cultural where it is ok to cause someone the right kind of pain.

And it’s very hard to have the individual fortitude to build an internal monologue that goes like this: “the fact that I’m feeling a lot of pain means this is a prime opportunity for growth.”

With fluff and abuse at the polar ends of the cultural spectrum, getting this right is hard.

Leaders are defenders of the standard 

The standard for thinking and performance starts at the top, and the leadership of an organization must constantly live the standard and hold all others to the standard (this is also the principle of the great book The Score Takes Care of Itself).

It takes a lot of mental stamina to hold the bar: in 1-1 check-ins, in team meetings, in external conversations with partners…

…to never nod your head unless you mean it is flat out exhausting… to always ask the next probing question is annoying…. to say it’s not good enough yet is tiring…

But if you don’t do it you, your team, your organization will slide into mediocrity.

Getting the balance right between people, processes, and technology

Leaders have a finite amount of energy and capital to allocate across people, processes, and technology.

Different organizations, industries, and time periods require different allocations – as well as different types of expenditures.

Dalio goes deep in how he managed these as he grew his hedge fund, early on relying more on technology than most of his peers. While some his efforts are generalizable, many of them are not.

But the discipline by which he came to his approach is generalizable, and it’s something I want to keep working on as our team, technology, and industry evolve.

Application

After our team conversation, we’ll have to figure out how to apply these lessons. In some cases, it might simply be through consciously applying these principles in our conversations; in some cases, we’ll build processes; and perhaps down the road we’ll build out some technology.

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How does a MGMT team figure out what their organization does?

On its face – “what does your organization do?” – should be an easy question for a MGMT to answer.

But it’s a hard question that I doubt many MGMT teams could accurately answer.

Three Reasons for “What We Do” Failure 

First and foremost, MGMT often confuse the question “what do we do?” with the question “how will we succeed?”

Second, MGMT teams often can’t say what they do in 1-2 sentences because they have failed to achieve clarity around their core activities.

Third, MGMT teams often can’t articulate the tactics and tasks that employmees execute in the daily carrying out of “what we do.”

My Tactics Failure 

Recently, I was struggling with executing and felt that achieving my goals was at-risk.

I then tried to think of what more I could do to achieve my goals.

I then realized that I wasn’t sure I possessed the full list of tactics I could pull from.

In short, I could not articulate the tactics and tasks of what we do.

Conducting a “What We Do” Audit 

Our team of four is twenty months old. And half our team has been with us for about a year or less.

This January, we achieved clarity on exactly what we do.

But we have not yet achieved clarity on what we do each day.

In hindsight, I think we should have brainstormed a tactics list before we launched our work.

That being said, codifying what we do each day after 20 months of work is not a terrible place to be in, given that you need time under your belt to figure out what you do each day.

To ensure we’re all learning from each other’s tactics – and building out a what we do toolkit – we’re conducting a three step process.

First, we’re going to articulate the major categories of daily work; i.e., “coach CEOs” and “coordinate with other philanthropists.”

Second, we’re going to list out all the tactics that fall within these categories.

Then we’re going to pressure test our categories and tactics, and debate if / why they are things we should be doing.

Building for Effectiveness and Scale

Conducing this “what we do audit” and codifying the tactic toolkit will ideally help with efficacy (each of us is drawing from a great toolkit built with our collective knowledge) and scale (if the team grows new members won’t have to learn solely from modeling and direct experience).

Of course, it’s impossible to codify everything it takes to execute at the highest level. No team is self-aware enough to codify everything, and the work is complicated enough that new situations will require first principles analysis of execution tactics.

But efficacy and innovation are born out of deep knowledge. And codification is a way of increasing knowledge.

How to make strategy less confusing by getting rid of the word strategy

For many years I thought strategy was one thing when in reality it is two things.

I thought strategy was answering the question: (1) how will you achieve your mission?

In reality, strategy is answering two questions: (1) what will you do? and (2) how will you succeed?

I thank Patrick Lencioni for helping me achieve this clarity, as well as our current team for thoughtfully working through both of these questions when initially I had only worked through the first.

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For example: a non-profit’s mission might be to increase economic opportunity for low-income families.

This non-profit might then say that their strategy is to operate charter schools, raise money for post-secondary scholarships, and partner with local employers for job placements.

In this answer, the organization is answering the question: what will we do?

Alternatively, the non-profit might not mention the above and instead say that their strategy is to form incredibly deep partnerships with their families, develop the best teacher coaching program in the country, and use data analysis to find great college and career matches for their students.

In this answer, the organization is answering the question: how will we succeed?

Because “strategy” has evolved in to too broad of a concept, either answer might be deemed acceptable.

But it’s vial that an organization answers both questions.

As a leader, you need to be very clear about what is that your organization will do to achieve your mission.

As a leader, you also need to be very clear about how your organization will out-perform other organizations that are doing the exact same thing.

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Most often, I see leaders in the non-profit sector make the same mistake I made: they have only thought hard about what they will do.

Too often, leaders don’t spend enough time answering the question: how will we outperform everyone is who doing the exact same thing?

Rational compassion is a competitive advantage

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Paul Bloom recently wrote a book called Against Empathy.

The thesis of the book is: rational compassion > empathy.

In other words: empathy (caring how someone feels at the moment) is poor guide for moral decision making when compared to rational compassion (which is more utilitarian in nature).

The difference is easiest to see when it comes to parenting: an overly empathetic parent might respond to a child’s failure by giving the child a cookie (thereby immediately decreasing the child’s suffering), while a parent utilizing rational compassion might help the child process her emotions (thereby reducing the probability of future instances of suffering).

While the idea is rather intuitive, we’re so hardwired for empathy that practicing rational compassion, especially at work, is very difficult.

Because it’s so hard to practice, and because most people are not good at it, the consistent use of rational compassion can be a competitive advantage for doing good in both the for-profit and non-profit sector.

List of Areas Where Rational Compassion > Empathy at the Work Place

Executing strategies that cause short-term harm for long-term gain: Tough decisions (such as school closures) cause short-term pain to others but can provide significant long-term outcomes. Being guided by rational compassion can help you get through this pain.

Pivoting and cannibalizing: Similarly, at times an organization needs to destroy existing program lines and harm existing beneficiaries of their work in order to pivot to a more productive model which will eventually add move value to more people (think Netflix going from mailbox to streaming). Empathy for existing employees and customers can blind one from the rationally compassionate act of eventually serving more people better.

Performance feedback: Rational compassion will lead you to give very direct and practical feedback so a colleague can improve her performance and achieve her and the organization’s goals. Having empathy for underperformance will lead to the avoidance of direct conversations, which in the short term causes more pain.

Firing people: Too much empathy for an individual who needs to be let go can cause immense harm to the people you are trying to serve. Especially in philanthropic work, firing a relatively privileged person in order to better serve people in extreme need is the rationally compassionate thing to do.

Accepting flaws of ambitious people: Sometimes ambitious people have a lot of flaws, which can lead you to empathize with all the people they are negatively impacting. However, these flawed people can also change the world for the better. Analyzing their actions through a rational compassion lens will help you understand if it’s worth supporting or partnering with people who are flawed but who can help the world become amazingly better. It will also help you avoid working deeply with nice people who are not effective.

The Risk of Rational Compassion 

One of the hardest parts of rational compassion is that it often involves overriding the legitimate short-term needs of others.

In other words: you’re saying you know what’s better for someone than she does.

While this is less of a tension in managerial situations (it’s your job to make feedback, coaching, firing decisions) and for-profit work (the customer will ultimately hold you accountable), in philanthropy (where it’s your job to help others) this can be a deadly sin.

It’s a blurry line between rational compassion and technocratic hubris.

There’s no easy way around this, though research and accountability can help.

In education, test scores, attainment, and parent demand can provide medium term feedback loops to provide a check on incorrect rational compassionate assumptions.

But while there are risks with rational compassion, most of society is so tilted toward empathy (especially in the education sector!) that an increase in the practice of rational compassion would be a welcome turn.

 

Applying portfolio reforms to postsecondary problems

I just got back from a trip to New Orleans, which continues to be a well of friendship and inspiration.

I. Where should you spend the next philanthropic dollar? 

In a few conversations, the following questions came up:

  1. Are the kids we serve going to succeed in life after high school? What will their lives be like when they are 30? Will they be living meaningful and happy lives?
  2. Is the marginal dollar of philanthropy best spent on making the K-12 system better (after 10 years of improvements) or trying to overhaul the post-secondary landscape?
  3. If you wanted to radically improve post-secondary, what would you do?

II. Post-Secondy portfolio 

The K-12 portfolio mindset entails viewing an educational system in terms of operators (running schools) and seats (how many students are served).

This mindset could also be applied to post-secondary.

By 2020 or so, New Orleans will be graduating around 3,000 students a year.

Let’s say that about 1,500 of them will be prepared to succeed in a four year college; 1,000 of them will be prepared to succeed in a 1 to 2 year credentialing program; and 500 of them will need deep support to enter the workforce and exit crisis situations.

Of the four year college students, you might need 500 to 1,000 “KIPP to College” type supports to ensure students make it through.

For the credentialing programs, you’d need 1,000 seats that can reliably produce students with employable credentials.

For the crisis students, you’d need employment and social service operators that could transition students into jobs.

III. Post-Secondary investment intermediaries 

Instead of assuming this will naturally happen in New Orleans (or any other city), you could capitalize a new or existing non-profit intermediary to launch, recruit, and support post-secondary providers.

At the outset, the intermediary would create a business plan where it laid out how money it would need to get X% coverage on the aforementioned 3,000 seats.

High-Quality existing local providers (like the coding bootcamp Operation Spark) could cover some of the seats, and national providers like Match Beyond could be recruited in.

Overtime, you’d expand what was working, close what wasn’t, and support new entrepreneurs to keep innovation going.

IV. Getting funding streams right

Most states subsidize mediocre public universities; the federal government tops this off with Pell grants.

To make the 3,000 seat post-secondary strategy viable, you’d need to blend a mixture of public support and tuition to make providers sustainable.

Louisiana’s course choice provides a revenue stream for programs that started working with kids while they’re in high school.

Creating a new university that housed many of these programs could allow for the accessing of Pell grants.

Wage contigent loan programs could also be an option for programs that were consistently placing graduates in high-performing jobs.

V. Who are the entrepreneurs that will seek out the 10x play?

The early New Orleans K12 entrepreneurs felt that they could deliver something to students that was significantly better than the existing system.

They were right.

A post-secondary transformation won’t happen on its own.

It will take a set of entrepreneurs to put forth a plan, galvanize funding, and spend a decade building the new system.

Is this the right play? If so, who will step up?

What I Learned from Watching Kaya Henderson Lead

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After nearly 10 years working in the district, Kaya Henderson is stepping down from her post as the chancellor of D.C. Public Schools.

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As the chancellor, Kaya consistently made the case that it is vital that the district thrive and provide a high-quality neighborhood option for students across the city.

As an outsider looking in, I did not agree. In Education Next, I made the case that D.C. should transition to an all charter school system. And, in the Washington Post, I argued that maintaining neighborhood schools in their most exclusionary form would increase historical inequities.

But you can learn a lot from people you disagree with.

And Kaya taught me much about how a superintendent can effectively execute an ambitious agenda.

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If I had to sum up what I learned from Kaya, it would be this: communicate a clear agenda of apple pie and spinach, and make it clear that getting the apple pie is tied to eating the spinach.

Too often, reform superintendents lead with all spinach: teacher evaluations, school closures, budget cuts, accountability systems, etc.

They say: “the system needs to be fixed.”

Rarely do the put forth a crystal clear vision of what schooling should look like; rarely do they describe the rich educational opportunities that all children deserve.

They give families little to believe in.

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Kaya consistently put forth a compelling vision of what DCPS could be.

Moreover, even when she had to make incredibly difficult decisions – such as when she closed 10% of schools in the entire city – she tied these decisions to providing broader educational experiences to children.

As the Washington Post detailed:

Henderson’s proposed closures also triggered opposition, but she is widely seen to have handled community relations more deftly than her predecessor, sponsoring a series of public meetings throughout the city and inviting parents and activists to help refine the closure plan.

The savings will be plowed back into schools to improve programming, including into libraries and arts and foreign language offerings, Henderson said, adding that the public will get a detailed view when school-by-school budgets are released in the coming months.

About 140 staff positions will be lost, but given normal attrition through resignations and retirements, Henderson said, “we actually feel like the loss will be minimal.” She said she does not expect any teacher evaluated “effective” to be out of a job.

Most superintendents avoid closing schools, or if they do close schools they do so in a manner that alienates communities.

But Kaya rightfully connected these hard decisions to a better future, and most importantly, she followed through on expanding educational programming.

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The best superintendents are populists, not technocrats.

They put forth a compelling educational vision that inspires the public.

But populists are not all the same. Some put forth a beautiful vision that is grounded in pragmatism, while others put forth a beautiful vision that is pure fantasy.

Kaya, I think, was a pragmatic populist.

And she taught me that this is likely the most effective way in which to lead a school system.

I don’t think I could every lead a public system as effectively as she did; but if I ever find myself in this position, I will strive to live out the lessons that I learned from her.

Is No Excuses or Personalized Learning the Low Hanging Fruit of School Improvement?

On average, I visit a school every other week or so. For the most part, these schools are equal to or better performing than the median urban district school.

During these visits, one question I usually mull over is this: if I was leading the school, what would I focus on to drive the next phase of improvement?

Often times, what the school leader is focusing on and what I would focus on are at odds.

I don’t have extremely high confidence in my analysis, so consider the below speculative.

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Here are the things I most often here school leaders saying they need to improve on: personalization, student ownership, and critical thinking. Tactically speaking, this often leads them to experiment with new models of instruction and technology.

All good things.

But I’m often thinking that the school really needs to get better at: instructional delivery, higher ratios of student intellectual engagement, and more effective use of small group instruction.

Most school leaders seem to believe that they have the basics down and need to go from good to great.

I tend to think that most schools are mediocre at the basics of things such as cold calling, wait time, efficient time on task, and tutoring – and the other hall marks of the no excuses model.

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So here’s some questions on my mind:

  1. Should the median charter school be focusing on getting better at the basics of the no excuses model or experimenting with deeper innovation?
  2. If it’s true that the median charter school is still mediocre at the no excuses basics, what should we take from this? That high fidelity to the no excuses basics is operationally hard to scale for either intellectual, emotional, or human capital reasons? That many leaders don’t think the no excuses basics work?
  3. Is there a progression of improvement (i.e., you need to get the basics right before you work on deeper innovation) – or does shifting to more innovative models allow you to bypass the no excuses basics and still get academic gains?

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My hunch is this: only the top tier charter organizations and the very best entrepreneurs should be working deeply on the margin of innovation.

Most charter schools should be working on the margin of better adoption of the tenets of the no excuses model.

Once new models are hammered out and refined – and get better results than the no excuses model – then the median charter school should begin adopting these new models.

But not before that.

In sum, I think better fidelity to the no excuses model is the low-hanging fruit of school improvement.

Maybe I’m wrong? Maybe I’m very wrong?