I Get a Cookie

It turns out that Jerry Seinfeld has a 24 hour rule.

Whenever he writes any new material, his rule is not to show it to anyone for 24 hours.

The rationale is that writing is a brave, creative act. We humans need and deserve positive reinforcement every time we engage in that act of bravery.

Part of the way we preserve that is by shielding anything new we’ve created from others’ eyes. This allows us to experience the halo of “I did it” before experiencing the crush of “maybe it’s not any good.”

In fact, Jerry advises that when we do a brave act of creation, we should give ourselves a (metaphorical or actual) cookie.

Time and again, I find myself skipping this congratulatory step, the one in which I get to bask, for just a moment, in the knowledge that I was brave today, that I created something new.

Instead, I nearly always ship off that new thing to someone for their quick reaction and feedback (time’s a-wastin’). Or, just as bad, I finish my first draft, put down my pen, and notice how much time that took and all the other undone things on my to do list.

One solution that helps me is having time in my calendar for “brave work:” empty spaces that are only for creating new things. This way I know what that time is for, and I cannot beat myself up for other tasks that remain undone. This also helps me remember that brave acts of creation and efficient time management exist on different axes.

Finally, I remind myself of the advice of one of my favorite yoga teachers: we can leave our problems and our worries outside of the studio door, because we can be sure that they’ll be there waiting for us when our practice is done.

So, maybe it’s time to resolve that our best work should be free from prying, critical eyes for a day.

Without knowing there’s some psychic reward waiting for us on the other side, why will we ever dare to take the plunge?

Bugs or Features

Most organizational change efforts frame things that aren’t working as bugs in the system.

As in, “That’s not working the way we want it to. We’re not doing this the way we’d like to. We just need some help with…”

One of the great insights of the Adaptive Leadership work of Ron Heifitz, Alex Grashow and Marty Linsky  (great short summary PDF here) is that systems are optimized to deliver exactly the results that they deliver.

Put another way: those things that are going wrong aren’t bugs, they are features.

This means that things are the way they are because it serves someone’s purpose – most often the purpose of someone with authority. That thing that everyone says they’d like to achieve (that better result, that clearer strategy, that adoption of a new decision-making process) is less valuable than something that’s going on today.

So, any time you see a gap between what people say they value and how they’re behaving, stop and look more closely. Look more closely to figure out what that valuable “something” might be.

If you don’t do this correct diagnosis upfront, you’ll be unnecessarily surprised when:

…the new person hired into that just-created, change agent role fails after 12 months.

…the guy who endlessly complains at the water cooler never seems to quit his job.

…the new mission statements end up as empty words on a page.

…and Facebook, to much fanfare, creates a Oversight Board, funds it with $130 million, and then systematically hides information from and misleads that Board (link to a free WSJ article for readers).

If we want to make change, whether in our own family, our organization, or in a social system, our first step is to remind ourselves: this system is delivering exactly the results it was designed to deliver.

This system—all systems—is not flawed. They are functioning perfectly at delivering the results that they currently deliver.

Once we see this, our next step is to figure out: who is being served by the results that are being achieved today?

And then, finally: how do we tip the scales so that the actors in our system are willing to do something different, something that makes it harder to allow things to continue the way they are today?



When we sit down, first thing in the week or first thing in the morning, to our desk, what do we do?

At this precious moment when the sun is still low in the sky and our mind is clearest, how do we choose to act?

Because so many of us are working remotely, we aren’t starting our days pushing through the stress and distraction of our morning commutes. There’s no need to fight our way through traffic, people and transit systems to finally land at our desks.

What an opportunity, then, to take advantage of the calm of the morning.

What a chance to quiet the chatter, to pull back our aperture and think bigger…

…about what this week would look like if it were really successful (planning).

…about what we could look like in one month or three if we really invested in our own professional development (self-reflection).

…about a piece of work that we’ve been stuck on, and a new way to approach it (problem-solving).

…about the direction of travel of our organization, and whether it needs a tweak or an overhaul (strategy).

A quiet morning is a terrible thing to waste with cleaning out our inboxes and “just checking” our social media feeds.

This is our most productive time, and its ours to do with as we choose.

Good Mistakes, Bad Mistakes, No Mistakes

We all know we’re supposed to be OK with mistakes, that they happen.

And yet, if you’re like me, you hate mistakes. You hate making them. And, sometimes, you can’t help being frustrated when those around you make them as well.

Which, of course, is both right and wrong.

Some mistakes really are a problem.

Careless mistakes—a term I mean literally, a lack of care taken for something important—really must be avoided. The discipline of a professional requires us to do our work with care and attention. This is the promise we make to ourselves, to our colleagues, and to our customers, and it’s our job to honor it each and every day.

Repeated mistakes are also a problem. They mean we’re not learning.

But no mistakes…that’s not OK.

It’s our job is to move at a certain pace, with a certain sense of forward motion, and with a willingness to walk out on limbs we’ve never stepped out on before. If we are doing all these things, we will have to get some things wrong some of the time–either because we moved too fast, or because we are trying things that are truly new to us, things that we’re not yet good at specifically because they are new.

If this seems counterintuitive, think of it this way: if we are getting nothing wrong all the time, that has to mean that we’re either absurdly lucky or that we’re not moving fast enough, not moving forward quickly enough, and we’re not walking out on limbs in the way we’d like to think we are.

Viewed in this light, mistakes aren’t just “not a problem,” they are valuable. They are the data that tell us: look at that, we are moving fast enough, we are being brave, we are taking enough risk.

We might still reflectively dislike mistakes in the moment, but it’s our job to praise the right kind of mistakes, and to praise the mistake-maker (whether ourselves or someone else) for their courage and bravery.

They (or we) are moving in the right way, taking the right risks, walking out on enough limbs, and, naturally, sometimes mis-stepping.

That’s good news indeed.

Awesome Hiring, Awesome Team

I’ve always found First Round Review’s articles to be exceptionally useful. Lately, they are on a roll.

Our company, 60 Decibels, is going to be doing a bunch of hiring in the next six months, so I shared this article with our team:

First Round Review: 20 Underrated Qualities to Look for in Candidates — And 50+ Interview Questions to Suss Them Out

I particularly appreciate both the list of the 20 traits and the practical interview questions for each trait. As interviewers, we often do a poor job of assessing whether a person is right for a job (and whether the company is right for that person). This is because most of us interview infrequently, so we give little thought about how to do it well or we’ve gotten comfortable doing it the way we always have and stick with what’s familiar.

The reality is that there are few things more costly—in terms of money, time and culture—than bad hires, so it’s worth investing the time to try new ways to interview.

But wait…there’s more.

If you squint, you’ll see the other side of the coin: this list is also a helpful guide for what makes a great team member.

Here are the 20 traits of great hires / team members. They:

  1. Embrace change and exhibit adaptability
  2. Can get their team to open up (remotely)
  3. Care about empathy
  4. Tell true tales of failure — not humble brags
  5. Keep DEI top of mind
  6. Sell the team, not themselves
  7. Look for ways to improve processes and reduce administrative burdens
  8. Challenge the defaults
  9. Can iterate and introduce change
  10. Focus on outcomes, not (just) shipping
  11. Will help you avoid bureaucracy
  12. Apply a long-term lens
  13. Are fueled by curiosity
  14. Are clear on the things they don’t want to do.
  15. Exhibit thoughtfulness
  16. Can point to a pattern of taking initiative
  17. Show a need for speed
  18. Are good at spotting superpowers
  19. Demonstrate a knack for finding the 10X — not 10% — improvements
  20. Can tell you what you should be looking for.

As I spent time with these 20 traits, I found myself bucketing them into five categories:

  • Flexible, moves fast, avoids bureaucracy: 1, 11, 17
  • Takes initiative, is curious, is always trying to make things better: 7, 8, 9, 13, 16, 19
  • Empathetic, values diversity, is humble, communicates & connects with others: 2, 3, 4, 5, 6
  • Keeps an eye on the big picture: 10, 12, 20
  • Is self-aware: 14, 15, 18

These five categories are an excellent jumping off point for what makes a great team member and, consequently, the building blocks for culture.

(Bonus: here’s a google doc with my cut-and-paste of the 50+ interview questions from the article. I hope you use it.)

Let Me Think About That

I’m an engager.

Meaning: put a problem, a question, a concern in front of me, my instinct is to dive right in. Always.

So, I found it confusing when, a few years ago, a coach I was working with encouraged me to practice saying, “That’s a great point, let me think about it and get back to you.”

To me, this response felt tepid and disingenuous, a way to feign interest in reflection to avoid meaningful, heated debate.

But, much as I love Star Trek and the inimitable Jean-Luc Picard, I’ve come to learn the limitations of my always-on engagement approach.

The first and biggest problem with always engaging is the inadvertent trade between listening and responding. When we (always and immediately) jump into “let’s solve that problem” mode, we can, ironically, make people feel less heard. Diving into potential fixes can skip past properly sitting with the problem. The result is missing the opportunity to express solidarity and empathy. Worse, we ignore the fact that often what people care most about is being heard – it is nearly always more important than finding any big solution.

So, try, “It sounds like what you’re saying is [this]. And I imagine that is challenging because [this],” and see where that leads.

Second, jumping ahead to problem-solving means we typically are accepting—hook, line, and sinker—that what the person has said is an accurate representation of what is wrong / of what they are feeling. In truth, it’s just as likely that the first presentation of the problem is what is easiest to say. Before we start solving the problem, we need to make sure we understand what it is. The answer, then, is to express curiosity and inquiry before jumping in.

Such as, “I see. That makes sense. Can you say a little bit more about that?”

Finally, any successful discussion of a difficult topic requires both (all) people involved to be able to productively manage their emotions. This means that we must dance in the productive zone of disequilibrium, maintaining the “heat” of the conversation we’re having without either letting it either (a) dissipate to quickly or, more likely; (b) overwhelm our ability to stay engaged in the conversation.

I don’t want to encourage avoiding serious, real conversations. But I also have seen how easily these conversations can spiral negatively when not managed properly. If one or both of the people involved lacks the skill to navigate heat successfully, no solution is possible: when pushed too hard too fast, our minds can only process emotions like fear, anger or shame.

“That’s a great point, let me think about it and get back to you,” when said honestly and with good intent, really means, “this is important to me, and I need time to process it.”

It also might say, “I’m concerned that my emotions are spiking to a place where I can’t productively engage in this right now. So let’s come back to it later.”

Now, if you’re not an engager—if you know that you’re more likely to avoid the “real” conversation—then this strategy is probably not for you.

But if you’re like me, this might be an important tool to add to your arsenal.

Because, on top of everything else, we’re all less able than we think to hear and process, in real time, a different, difficult perspective.

Buying ourselves a little time allows us to properly reflect on new points of view. It’s a way to give ourselves time to do the work that we, individually, need to do before engaging with our counterpart to work through the issue at hand.



Close to the Bone

The more people I’ve gotten to reconnect with this summer—our respite, in the US, between wave after horrible COVID-19 wave—the more I’ve seen a pattern.

Each of us, no matter our circumstance, background, and personal situation, has found our resilience shaken. Our reserves are low. At some point in the past 18 months, we’ve gotten cut too close to the bone.

We carry the accumulated toll of month after month of fear, uncertainty, new responsibilities and isolation.

And while we had a brief window when it felt like the worst was behind us, now we’re entering yet another season with a rising caseload and rising uncertainty; the prospect of putting COVID-19 behind us might be replaced with the prospect that this is the new world we all live in.

Most of this change in us is invisible. From the outside, we look OK. But when we dig a bit deeper and ask more questions, we can see the cracks in the foundation, a shift in our emotional structural underpinning that places us on less stable ground.

I, for one, don’t have a quick answer for how to address this in ourselves. Surely part of the answer is to go easy on ourselves, make time in our days to be in nature, to quiet our minds, to put down our devices and to break a good sweat.

I would also suggest that we can help one another by remembering that no one will come out of this unscathed: while we may emerge stronger in the end, we have some deep valleys to get through from here to there.

Since we don’t need a special occasion to do so, let’s choose to act towards each other with more forgiveness, kindness and generosity of spirit.

Let’s commit to being more open-hearted with each other.

Let’s commit, starting today, to ask each other real questions, and to stay fully present for the answers.

Most of the time, and especially now, accompaniment is the greatest gift we can give to one another.

Because It’s Inconvenient

We make a plan and commit to something.

An initial buzz hits us, as we visualize the results that will come from our hard work.

A few days in, our commitment feels awfully inconvenient.

The time doesn’t feel right; we don’t the energy, again, for this hard thing.

Maybe we have a legitimate conflict, another something or somethings to get done that we’d have to give up.

These somethings all seem more fun or more important.

Plus, didn’t we just do this yesterday?

We did, but that was yesterday, and this is today.


We do it today, because we committed.

We do it today, because it’s hard.

We do it today, because it’s inconvenient.

And in the doing we see what it takes to hit our goal.

The things we have to give up.

The things we have to push through.

All the noise that used to scare us off but doesn’t, this time.

The Willingness to Throw it Out

A lot of my work days are about efficiency.

Tearing through my Inbox.

Having as few meetings as possible and making them as short as they need to be.

An overall feeling and attitude of moving fast and keeping an eye on the clock.

I’ve been in an overdrive version of this mode for the past few months, with an intensive focus on external sales and fundraising.

Then the other day, working on an important document, I had what I thought was a brilliant idea.

I started on it, made a terrible first draft, played around with the document, trying to make it resemble the original bolt of inspiration.

And then I had a paralyzing thought, “What if this is a waste of time? What if I work on this for the full two hours, give it my best shot, and then discover that it’s no good?”

And, if that’s a possibility, should I stop before I start—would that be the efficient thing to do?

Of course it would, and it would be a terrible idea.

The only way to create something truly worthwhile, something that only you can create, is if you walk along the This Might Not Work edge.

That means that you are actively aware that what you’re doing might not be good enough, that you’re dancing with that fear. You’re aware that even if it doesn’t work this time, the only way, in the long run, that you produce anything worth anything is if you consistently spend time doing things that might not work.

Which means that the point of all that efficiency is to create space that plays by a different set of rules.

It’s a space where you get to dance and make a fool of yourself and try daring things, many of which may end up in the trash, so that some of them can be amazing.

Looking When You Know It’s There

Entrepreneurs are famous for seeing the things others cannot. They believe in a truth that seems like fiction to everyone else.

For example, AirBnb founders Brian Chesky and Joe Gebbia failed to raise any outside money from late 2007 until early 2009. Maybe it makes sense: a business where strangers stay in each other’s homes doesn’t seem like a winner. In fact, they famously had to sell Obama O’s and Cap’n McCains Cereal to fund their startup, raising $30,000 in the process.

The big challenge, when we are attempting something new and difficult, is to know what to do with outside feedback:

Does what I’m hearing tell me a fundamental truth about the validity of my idea?


Do I have so much conviction in my idea that I’m sure it’s right, despite not having found a customer for what I’m selling…yet.

Our level of conviction determines how we interpret outside feedback.

For example, consider the widespread phenomenon of “kitchen blindness:” the inability to find an item of food that is sitting right in front of you – milk, OJ, the salt or, famously, butter.

While “kitchen blindness” is often be the byproduct of laziness, it’s also true that there are two ways that we look for things:

  1. When we look without prior knowledge, we use the data that’s coming in (“I’m not finding the baking soda where it’s supposed to be”) as information to confirm or refute our hypothesis that we have baking soda.
  2. Whereas if we are sure we bought baking soda, and we simply are not finding it in the freezer, we take that to mean that we’ve got to look in the pantry, in the shopping bags, and in the trunk of the car.

One of the hardest lines to walk as an entrepreneur or creator is the daily choice between using outside feedback to adjust / refute our hypothesis vs. sticking to our guns. (for more on learning when to quit, there’s no better book than The Dip by Seth Godin.)

Are they telling me something true that they know and I need to learn?

Or is this my “naysayers be damned” moment, and do I believe, like Steve Jobs did in 2007, that I can design and sell a smartphone that doesn’t have a keypad?

Deep down, it’s a question of conviction:

How sure am I that what I’m looking for is there?

Because if I’m really, really sure, then it really is there, and all I have to do is find it.