Good Decision-Making

Ultimately, our job as leaders boils down to a few things. Having a vision and strategy that is shared, understood, motivating and that inspires action. Creating a great culture. Hiring and supporting great people. And, maybe less obvious, creating an organization that’s good at making decisions.

It turns out that there’s a very high correlation between organizational effectiveness and the quality of organizational decision-making. And the best, most actionable article I’ve found on understanding the quality of an organization’s decision-making says it’s function of:

  • Speed: how fast do you decide?
  • Effort: how much work goes in to making decisions?
  • Quality: how good are the decisions?
  • Yield: how well do you turn decisions into actions?

As someone who’s transitioned from the non-profit to the for-profit sector, my experience is that non-profit organizations typically decide more slowly and with more effort, all without resulting in consistently high(er) quality / higher yield decisions.

I think this is a function of the more multi-faceted accountability in the non-profit world (multiple criteria for success, multiple stakeholders). This in turn leads to slow(er), high(er)-effort decision-making which begets a culture that accepts slower, higher-effort decision-making, even when it’s not always needed.

This is not to say that faster is always better: speed is not useful if we make lots of quick, poor decisions.

Indeed, one of our jobs as leaders is to consistently walk the line of always moving quickly while managing to get the right input from the right people, so that decisions are (mostly) high quality.

The nuance is that how we decide develops into a cultural norm: people watch how decisions get made, learn that behavior by osmosis, and replicate whatever your decision-making culture is.

For example, is it OK in your organization to:

  • Make decisions without formal authority?
  • Change a decision after it’s been made? After the deadline?
  • Leave a decision-making meeting without a decision getting made?
  • Have a more junior person be the decision-making in a meeting with someone more senior?
  • Make a decision that is not documented?
  • Make a decision that doesn’t turn into action?
  • Be unclear who the decision-maker is on a given topic?
  • Have one decision-maker?
  • Have many decision-makers?

While there’s no right answer to any of these questions, my view is that organizational growth creates complexity, and complexity slows things down and allows people to hide.

That’s why most of the time, most organizations would benefit from faster decisions being made by fewer people who take more ownership around being “the decider.”

One helpful way to jumpstart these conversations is by starting to frame decisions as either Type 1 (irreversible, make them very deliberately) or Type 2 (reversible, prioritize speed). You’ll quickly discover that most decisions are Type 2, and that just might give you the freedom to move faster on them.

One final thought: one of the easiest ways to lead, no matter where you sit in an organization, is by choosing, today, to make more decisions without triple-checking if it’s OK. The worst thing that will happen is that you’ll discover that deciding really isn’t allowed (which is important information). The best thing is that more people will start turning to you to decide more things, because you had the courage to step up in the first place.

Stop / Start / Keep

I was first introduced to the concept of After Action Reviews by Colonel Patrick Tierney, a retired U.S. Army officer who I got to know in my time at Acumen.

An After Action Review (AAR) is a review of a completed operation, typically run by the commanding officer and with all members of the operation present.

In an AAR, your job is to answer four questions:

  • What was expected to happen?
  • What actually occurred?
  • What went well and why?
  • What can be improved and how?

My sense, from talking to Col. Tierney, is that there’s a level of (harsh) objectivity in an AAR that serves two purposes: surfacing the truths about what happened and building a culture of transparent accountability. Col. Tierney would describe going into an AAR as, “you have to strap on your thick skin before heading into that room.” The feeling was that any and all critiques would come out in the AAR, and then, afterwards, you were done and would put the AAR behind you.

While there’s a full AAR process that is itself very powerful, at a practical level I’ve often found our teams boiling AAR’s down to a simple start / stop / keep rubric: What do we need to start doing? What should we stop doing? What should we keep doing?

To operationalize this, create a table in a Google Doc and have all team members spend the first 5-10 minutes of the meeting filling in the document (or, better, do this before the meeting). In addition to writing, anyone can also +1 another team member’s entry to show they agree with it. For example:

Start Stop Keep
Sharing all spec details at the start of the project ++++
More clear pushback to the client when requests are out of scope +++++
Adding requirements late in the process +++++
Parallel conversations ++
Having daily standups ++++
Clear decision-making +
Raising hands to support each other +++

As I head into 2022, I’ve found myself switching gears more slowly than in the past, likely the result of the Groundhog Day that it we’re living through: cancelled trips, postponed back-to-office plans, tons of emails from schools about new protocols and Zoom options, and global uncertainty.

That said, I know the beginning of the year is an invaluable time for reflection, planning and intention-setting, one that we shouldn’t miss.

With that in mind, I’m planning to start my year with both a personal and an organizational start / stop / keep list.

On the personal front, the list will focus on how I manage my time and my energy, the structure of my days, and any adjustments I might make to keep myself more grounded while still getting everything that I need to get done done.

And, for our company, I’ll use this as a conversation-starter across multiple teams and geographies, a chance for everyone to share what we need more of, less of, and the things that went really well in 2021 that we need to keep.

You might want to try it too.

Happy new year, and here’s to a great start to 2022.

My Favorite Books of 2021

A number of you reached out asking for my 2021 book recommendations (including fantasy fiction). I have to say, I had more misses than hits in what I read this year, but there are a few books that really stood out.

Here are my top five books of 2021, along with 9 other good books I read this year.

My Top Five Picks of 2021

The Overstory by Richard Powers: (2019 Pulitzer Prize winner) this book was magical. It is, ostensibly, about trees and our relationship to them. It follows a seemingly-unconnected group of characters across multiple decades. I found myself transported to another world and I loved inhabiting it. The book made me look at trees, and our relationship to nature, in a new way. This was definitely the best work of fiction I read all year – though it did take me about 100 pages to get into it.

The Warmth of Other Suns by Isabel Wilkerson: this book is the story of the Great Migration in the United States, the exodus, spanning more than five decades, of more than six million Blacks from the South. Isabel Wilkerson spent more than a decade researching the book and she tells the story through three protagonists: Ida Mae Gladney, a former sharecropper who left Mississippi for Chicago in 1937; George Starling, who left Florida for Harlem in 1945; and Robert Foster who left Louisiana in 1953 to become a doctor in LA, and who became, among other things, Ray Charles’ physician. The book has such narrative beauty that it reads like a work of fiction. And, from an educational perspective, I’m embarrassed to say how little I knew about the Great Migration and more surprised still that I had such a narrow understanding of the lived Black experience in the U.S. in the decades leading up to the Civil Rights movement: not only the day to day realities of Jim Crow but also the amazing hardship and bravery of pulling up roots and setting them down again in new, often hostile parts of the U.S.

Maybe You Should Talk to Someone by Lori Gottlieb: this memoir was breathtaking in its honesty, its poignance and its humanity. Lori is a psychotherapist who, at the start of the memoir, is dumped by her boyfriend. She starts seeing a therapist named Wendell for “a few sessions” to work through her grief, but finds herself digging much deeper into her own emotional life. Gottlieb shares her own struggles while also telling the story of four of her own patients. This book was equal parts surprising and beautiful.

Between the World and Me by Ta Nehisi Coates: Coates frames this book as a letter to his 15-year old son, describing the experience of being Black in the United States. Coates describe the systemic and institutionalized racism in the United States, drawing powerfully on his own experience and perspective while paying homage to  the work of James Baldwin. Shortly after finishing this I also read Coates’ We Were Eight Years in Power which I recommend just as highly.

Such a Fun Age by Kiley Reid: (2020 Booker Prize Nominee) Emira is a 25-year-old Black girl who is hired by a white blogger and public speaker, named Alix, as a babysitter. At the start of the novel, Emira is detained by a security guard in an upscale supermarket when she’s “caught” dancing with three-year-old Briar, Alix’s daughter. The incident is recorded by a white bystander, Kelly Copeland. Emira is a powerful narrator and first-time author Kiley Reid has an exceptionally deft touch in exploring the complexities of the relationships between an ensemble of leading characters and the different worlds they inhabit. She also has a wicked sense of humor.

Nine Other Good Books I Read in 2021

In case you’re looking for a longer list, here are some more that didn’t crack the “best” for me but were still good reads.

The Night Circus Erin Morgenstern: this one nearly cracks the “top” list, it’s a novel about Les Cirque du Reves, a magical circus that only opens from sundown to sunrise. It is escapist and magical and just plain fun.




Hamnet by Maggie O’Farrell: a beautiful novel about “Hamnet,” the young twin boy and son of William Shakespeare who died of the plague at age 11 in rural Stratford-upon-Avon in 1596. The names “Hamnet” and “Hamlet” were interchangeable, and this story centers around Hamnet himself, life in rural 16th century England, and his mother Anne’s experience of grief and loss. The book is a moving piece of historical fiction and is a wonderful read.

How the Word is Passed: A Reckoning With the History of Slavery Across America by Clint Smith: this is a powerful work of nonfiction that explains the centrality of slavery to American history through Smith’s personal experiences with various landmarks across the U.S.: Monticello, the Whitney Plantation, Angola (a maximum security prison near New Orleans), and Blandford Cemetery (the final resting place for tens of thousands of Confederate soldiers). Smith writes beautifully and he invites you to see these places through his eyes. In so doing, he shares a new perspective on slavery, on race, on American history, and he makes so much that is invisible visible.

The Shadow of the Wind Carlos Ruiz Zafon: a friend said this was one of his favorite books, and it’s sold more than 15 million copies worldwide, so perhaps my expectations were a bit too high. The book is set in 1930s Barcelona and is a fun, escapist thriller about a boy, Daniel Sempere, who sets out to find the lost novels of the author Julian Carax. Many of the characters were great and I loved the historical setting, I just felt like the book never really came together for me as much as I’d hoped.

The Invisible Life of Addie Larue by V.E. Schwab: another fun fantasy fiction novel, this one about Addie Larue, a girl who, by mistake, makes a deal with the Devil and who never ages. We follower her life from 1714 to 2020, and it’s fun to watch her through the centuries. At times, though, the novel felt a bit too Groundhog-day ish for me—not only does Addie never age, but how she shows up and engages with the world is also a bit repetitive. Still, it was enjoyable enough.

Rodham and American Wife by Curtis Sittenfeld: each book is a fictionalized account, one of Hilary Clinton and one of Laura Bush. Rodham is the better book, and it imagines a world in which Hilary Clinton never married Bill Clinton and in which she wins the Presidency in 2016. I enjoyed both books, though I had a bit more trouble following how fictionalized or not ‘American Wife’ was and its purpose seemed less clear than that of ‘Rodham.’ Still, they were interesting and original.

The Midnight Library by Matt Haig: this book was a NYTimes bestseller and on lots of ‘best of’ 2020 lists. It’s the story of Nora Seed, an unhappy woman who has the chance to visit a place between life and death—the Midnight Library—and explore the many lives she didn’t live. I enjoyed many parts of the book, and the various paths Nora explored…it just didn’t ever become more than the sum of its parts for me.


The Inner Game of Tennis by W. Timothy Gallaway: this book is a classic, published in 1972. It explores the psychology of tennis—and, really, of any sport—and, more specifically, how the mind and body interact when we compete. The simple, big idea that I took away is that, for sports we’ve played for a long time, our bodies actually know how to do all the things we want them to do, so our minds’ job is to focus on what we want to do—for example by watching the tennis ball and deciding where we want it to go—and not spending any mental energy thinking about the minutiae of technique. After I read this book, my squash game improved immediately and significantly, and mostly that was because I spent a month just trying to see the two yellow dots on a flying squash ball (which is nearly impossible).



As you can see, I had a good year of reading though I was let down a bit by my various attempts at escapist fantasy fiction (in fact, I just finished reading the three part Wildwood Chronicles which, after 1,000+ pages, was mostly a disappointment). Fortunately, I’ve also gotten to read all seven Harry Potter books again, more than once, at bedtime with my 10 year old daughter—this time the beautiful, large-format ones illustrated by Jim Kay—and I love them each and every time.

I hope this list sets you up for some good reading in 2022, and if there are books that I’ve missed that you love, please let me know!


No Backstop

In teams, in organizations, in families, there are certain roles that are played.

“Are played,” which is different from “roles that we play,” because the roles exist independently of their players. They exist to be filled, whether by the person filling them today or by somebody else.

Roles like:

The one played by the person who makes sure we keep moving forward fast enough.

The one played by the person who keeps us safe.

The one played by the person who expressed doubt, asks questions, makes sure we look at things from all angles.

The one played by the person who speaks up.

The one played by the person who lurks on the sidelines.

And the one played by the person who acts as a backstop.

The backstop role is essential: it’s the role of making sure everything is good enough to ship. This isn’t just about dotting i’s and crossing t’s. It’s things like making sure the story hangs together, that it connects to the big picture, that it’s on brand and that whole is more than the sum of the parts.

Sometimes, the person playing the backstop role really does have more experience, context and knowledge than the person who handed her the “almost finished” product. She’s been here before and can see and do things that others cannot.

But, just as often, the backstop person is just playing that role, because somebody’s got to do it and we’ve gotten used to being able to count on her.

While it’s a great relief to be able to rely on that kind of person, it also presents a risk. The risk is getting used to that role being played by someone else. The risk is teaching ourselves that someone else is going to put themselves on the line, to sit in the client’s shoes and always ask “is this good enough to represent us?”

And then, by definition, we’re not on the line, we’re not the arbiter of good enough, we’re not making the tough calls.

Behaving as if it’s OK to fall, because we have a net, is one way to teach ourselves that falling is OK. And then, day by day, almost imperceptibly, we start to become a person who falls.

The solution, of course, is to act as if there’s no backstop, to practice as if there’s no net.

Nets are essential if you’re on a literal high wire. But since, for most of us, our day-to-day work is rarely life or death, we’re much better off acting as if we didn’t have one, so we practice to putting ourselves on the line.

It’s Not Working

Just because something isn’t working today doesn’t mean it will never work.

It doesn’t mean it is impossible.

It doesn’t even mean that this will always feel this way.

Often, this feeling either means “it’s been a while” or “this is new.”

Most of our biggest mistakes in judgment and prediction result from over-extrapolating from the present.

What’s happening today is not meaningless.

It is, however, temporary.

The Spelling Bee Forum and Our Best New Ideas

Lately, my family and I have gotten obsessed with Spelling Bee on the NYTimes Crossword. Someone in our family does it nearly every day.

The game refreshes daily and we’ll typically spend 10-20 minutes playing it across all devices. The rules are simple: make as many words as possible with the 7 available letters; all words must be four or more letters long; and all must use the middle letter at least once. Also, there’s a Pangram every day, a word that uses all 7 letters.

Recently, the Times added a something called the Spelling Bee Forum. It has hints for each day’s puzzle, and is divided into two sections: (1) A grid that shows the number of possible words and their length, listed by letter…

..and beneath that, (2) A list that tells you the first two letters of the words listed in the above table.

So, for example, for last Sunday’s puzzle there were (per the grid above) 11 words that started with C: one with four letters, two with five, two with six, three with seven, two with 9, and one with 10.

Of these, per the next section of hints, 9 of the C words start with ‘CO’ and 2 start with ‘CU.’

As a family, whenever we play, we try not to click on the hints. But when we do check out the hints, I try to look first at the top table and then, if I’m really at a dead end, I’ll look at the bottom list as well.

It is difficult to overstate how helpful the first table is. I can be absolutely stuck, having stared at the same seven letters for 5 minutes straight, sure that there are no words left that I can find. Then, after a glance at the first table of ‘hints,’ and armed with the information that there are 7 words that start with the letter ‘G’ when I’ve only found three…it practically makes more ‘G’ words appear as if by magic.

This is a version of looking when know something is there (in the pantry, in your organization).

The new information—in this case about the number of words that start with the letter G—is telling me two things:

  1. To narrow my field of vision: looking for words that start with G will be fruitful.
  2. That I’m on the path to success: there are four more words that start with G. Hence, the (previously credible) voice telling me I’m at a dead end is silenced.

Having played Spelling Bee for a few months, I’ve become familiar with the ‘stuck’ feeling: staring at that honeycomb of letters and being fully, completely convinced that there’s nothing left there for me to find. Then my wife will come along and find ‘udon’ or ‘iconic’ or ‘epee’ or ‘naan,’ or we’ll click on the hints to look at the skeleton key for that day’s puzzle, and a new door opens.

While life rarely can tell us so cleanly which of the uncertain paths we’re exploring will be fruitful, there’s still a lesson here.

When we’re searching for new answers (how to fix a thorny problem, how to get unstuck, what our next product or offering should be) our biggest limitation is not our ability to find new and better answers. Rather, our biggest limitation is the voice, that gets louder after each passing minute, telling us we are stuck, we are done, there’s nothing fruitful here for us to find.

Perhaps, then, we all are spending too much time focused on improving our “looking,” “thinking” and “analyzing” skills…when our biggest untapped potential is the simple realization that the answer we’re seeking really is in the palm of our hands—if only we could see it.

(And why wouldn’t it be there? We’ve done the work up to this point. We are ready, we are prepared, we are the right person in the right place. Of course the answer is there!).

The moment we vanquish the thought that there’s nothing left to find, the moment we dance a bit longer with belief, the moment we dare to think that magic is within our grasp…that thought alone is what unlocks our potential.

“I’ve looked as hard as I can look. There’s nothing there that I can find,” sounds sensible and objective. But, in truth, it’s nothing more than a self-fulfilling prophecy.

More accurate would be, “I can’t find anything more because I’ve decided that there’s nothing more there left to find.”

Don’t look harder.

Don’t look smarter.

Look with more confidence.

Look with the belief that of course “it” is there for you to find, and you’re looking in exactly the right place.

Indeed, you have everything you need, right now, to make that next breakthrough discovery.

I Just Got Here

To you it probably feels, by now, all too familiar.

But to that customer or employee who just arrived today, it is all new: the product, the community, the story.

It’s easy to forget this when we’ve told our story 10 times, 100 times, 1,000 times or more.

Indeed, as the storyteller, salesperson, fundraiser, or CEO, if you don’t feel like you’re repeating yourself, you’re probably not sharing enough.

By all means, find a way to keep things fresh, but don’t stop telling the story.

No skipping steps just because it doesn’t feel new to you.

Culture Graphs

Culture (organizational or otherwise) can most simply be understood as “how we do things around here.”

There are a million “things” that make up an organization’s culture: things like meeting norms; how we talk to each other (in person, online); what it means when someone says “the deadline for this project is November 6th;” how inclusive we are.

To imagine this visually, imagine an N-dimensional chart with each element of culture on one axis.

And now, to keep things simpler, let’s collapse that N-dimensional chart into two dimensions – because otherwise all of this will be too hard to visualize.

Envision an organization’s culture represented on this graph. To explore what we mean here, let’s imagine two organizations.

Organization 1 has a loosely defined culture: we represent that with the broad shape on the graph, and the light color to show ‘low intensity.’ In organization 1, a wide spread of behaviors “works” because the culture is not strongly defined.

Conversely, in organization 2, the shape of the “culture graph” is much tighter and the culture is much stronger (darker color).

In organization 1, nearly anyone can “fit in” because anything goes in that organization. In organization 2, with a stronger culture, only a certain set of people will feel comfortable there, but, for those people, the culture will have a stronger pull that will keep them motivated and make them more productive.

Now, moving beyond thinking about the impact of the culture on the employees, let’s think about the impact of the employees on the culture.

Here’s where things get interesting, because culture is not static: each team member has their own influence on the culture, either pushing against (weakening) the existing culture or strengthening it.

Let’s visualize this as the cultural “force field” that each team member brings to our organization, each and every day. Like our two organizations, each person has a different cultural force field that they exert on those around them: it has a size, a shape, and an intensity…all of which affect how that person impacts the organization’s culture over time.

(I understand that the visuals might be breaking down a bit…stay with me here. The point is: the shape and intensity of your ‘culture graph’ today and tomorrow are a function of all the behaviors of your team between now and tomorrow: how people act, what behaviors are rewarded and punished, what people say, what they do…)

With this backdrop, we can ask a few questions about our organizational cultures, things like:

  • What is the shape and intensity of our own ‘culture graph’?
  • How does it differ by location, function, and seniority? Are these differences intentional?
  • When we think of the future, what do we imagine happening to our culture graph? Does today’s culture remain in place? Does it morph? Intensify so we stay true to ‘who we are’? Weaken so we can accommodate more people?
  • What do we do about people who supercharge our culture, who will serve as ballasts between today and the future?
  • And what do we do about people who perform well but who push against our current and future culture?
  • Most important: if you asked your team whether their job is to create and accentuate your culture, or to accept and adapt to it, what would they say?
  • What would you like them to say?

I share all this not to offer answers to the above questions, but in an effort to make the invisible visible.

Our culture either accentuates and accelerates everything we do, or it stands in the way, gumming up the works. Yet, despite these powerful multiplier effects, we often act as if culture will take care of itself.

Perhaps, then, it is time to bring it out in the open.

Perhaps it is time to invite ourselves and teams to see and own our active role in defining, strengthening and reinforcing “how we do things around here.”

Leading Indicators

Most of what we do today is going to bear fruit in a few weeks, months, or years.

This means that the feedback we’re receiving today–about how things are going around us, the results we are getting, the way people are feeling–are mostly the result of actions we took in the past.

Consider our oceans: they have absorbed 93% of the excess heat from greenhouse gas emissions since the 1970s. They are a buffer between yesterdays’ actions and today’s reality. They lull us into a false sense of security that what we’re doing today will lead to a safe tomorrow.

We are often blind to this time lag. We see what’s going on around us and falsely attribute today’s results to our current or recent actions.

Figuring out how long our actions take to create results—whether in our organizations, our families, or in the world—is one of the best ways to learn where to look to see if what we’re doing is, or is not, working. When looking for the right organizational KPIs, we’d do well to home in on those that tell us what will, or will not, happen in 6 months’ time (think: new sales leads generated, not new sales closed).

The high-leverage we should be asking ourselves is: how early do I need to adjust to make a meaningful difference?

Too Hot, Too Cold, Just Right?

I, like many of you, have spent the last 18 months working mostly from home.

In that time, I’ve experienced the challenges of more childcare, more meals to prepare, more tugs on my attention. I’ve also relished ditching my commute and the less glamorous parts of business travel, and have treasured having more time with my family.

For all the pushes and pulls, it certainly feels like, on balance, I’ve got more hours in the day to deploy.

The question is, how best to deploy them?

Do we run extra hot, finding even more time to work longer and harder?

Do we discover that we can run cold: in the absence of time wasted in planes, trains, and automobiles, can we get all that we need to get done in fewer total hours, resulting in shorter workdays.

Or is there a “just right” solution in which we spread our work our in discrete chunks across the 16+ hours we are awake?

The “just right” solution can be magical, but it also carries its own risks.

Sometimes, “just right” feels amazing: a few hours here, thirty minutes there, interspersed around a walk or cooking or driving kids around or time with friends and family. You can’t ask for more than that.

However, I’ve also noticed some important pitfalls of “just right.” For me, the whole thing falls apart when my “off” switch is faulty: rather than freedom with my time, I get stuck in a no-man’s-land of “always on a little bit.”

Here are some of my own leading indicators that I’m getting stuck in the wrong kind of “just right:”

  • Picking up my phone during every blank space (and realizing that I don’t know what I’m looking for)
  • Being confused, and a little anxious, when 30 free minutes present themselves
  • Facing the endless chatter of my monkey mind (note: that’s a great little video) during my down time
  • Trying to go to sleep but instead lying there having both sides of unfinished conversations from my day

Freedom and flexibility are beautiful things, but they require us to get really good at fully flipping our “on” and “off” switches: being hyper-focused when we are “on” (that means: no distractions or fake-work behaviors); and fully turning off the switch when it is time to stop.