Seeing the Problem Clearly

We waste a lot of time because we misunderstand the problem.

Our poor diagnosis leads to the wrong mental models. We then waste energy focused on addressing things that aren’t really a priority.

Worse, we incorrectly assume that “correct diagnosis” is binary: either we see things the wrong way or the right way.

In reality, we don’t flip from not seeing to seeing.

Rather, we have a first glimpse of true understanding, and we sharpen what we see over time.

If, tomorrow, you finally figure out what the problem is, in your enthusiasm you might rush to turn that eureka moment into a plan for action.

Let me suggest, instead, spending some time sitting with your new understanding.

Keep doing things the way you’ve been doing, while all the while keeping your hypothesis about what needs to change in the back of your mind.

Letting this gap persist—the gap between today’s practice and your (new) view of what things should look like tomorrow—will automatically force your diagnosis to sharpen. As your understanding deepens, you will have:

  1. A more complete understanding of what you need to do differently
  2. Much more conviction behind starting down that new path

The clarity of understanding will itself be hugely valuable.

The strength of your conviction will make it much more likely that you’ll successfully lead those around you to rally around the changes you want to make.

Terror/Freedom, Calm/Structure

I was talking with a colleague about what makes us most productive, and we came up with this fun 2-by-2.

We were discussing whether he was, in fact, most productive in the top-right corner: namely, when he’s got as much Freedom as possible, and has massive, important goals that are so big that they’re Terror-inducing.

We had a chuckle about this—it’s a caricature, to be sure—but it did get me thinking that this simple 2×2 might be a great shortcut for getting to know each others’ work styles.

For example, I’m also at peak productivity (though not sustainably) when I’m somewhere in the middle of the ‘Terror’ quadrant. A bit of fear leads me to crank out a ton of good work, whereas if things are too calm for too long they feel flat to me.

That said, Terror for too long does wear me down. What’s best for me is hanging out somewhere between Calm and Terror, with enough Calm for predictability and self-care and enough Terror to keep me motivated.

Similarly, I’m comfortable with, and like, a strong foundation of structure; and I find too much structure stifling. I need to be in the middle of that axis to thrive: structure as a jumping-off point for the freedom to dream about and create new things.

I find this 2×2 diagnostically helpful. For example, when I think about work groups that have trouble, the four that jump out are:

  • (Usually) One high-Structure person and one high-Freedom person. The exception is if this high-structure person is an awesome, self-aware supervisor who knows how to give their freedom-seeking team member tons of white space and motivation, while not constraining her too much. Conversely, a high-freedom person managing a high-structure person seems particularly hard to pull off. The high-structure junior person often ends up confused, stressed out or frustrated.
  • (Always) One strongly Structure/Calm person with another strongly Freedom/Terror person unless both are super-self-aware. These two environments are so different that these pairs struggle to find common ground.
  • Too many high-freedom people working together without someone to create structure. Also known as “chaos.”
  • High-freedom people who have been forced into high-structure roles. This is a tricky one because we naturally associate seniority with more management responsibility. That’s why we give management job to successful high-Freedom folks, and then get confused when they (and their teams) struggle.
  • Finally, I wonder if the High Structure / High Terror profile exists and, if it does, what makes that person thrive.

A parting thought, lest we lose the nuance here: maximum productivity does not equate to maximum well-being.

I expect everyone wilts eventually when they feel too much terror for too long. However, I do believe there are folks who have higher ‘terror’ thresholds and who find low-to-medium levels of terror exhilarating rather than off-putting.

We all surely inhabit parts of the framework in different settings and moments. The useful point for introspection is to explore our emotional reaction to each of the four quadrants, and unpack how that reaction impacts our energy levels, our focus, and our productivity.

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.

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.

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.

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.)

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.

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.





Goodbye Notebook, Hello Notion

For years I carried around a nice, small Moleskin notebook to every meeting. I had various systems, each typically lasting about a year, to distinguish between note-taking content and next steps.

Moleskin Notebook
Photo by Stationary Nerd

My notebook was a sacred object which, if lost, set my productivity back by weeks or more. That said, the constant iterating on how to manage the space and my to do list, the inability to search for anything, and my crummy handwriting combined for a system that I knew needed improvement.

This last year, when Zoom meetings started, I stopped using my notebook almost immediately.

This wasn’t a conscious choice: it had more to do with the physical setup of my desk and where I was sitting around my house. For a while I wasn’t taking notes, and I used other systems to track to do’s. It felt like things were working well enough, though I was nervous about what was falling through the cracks.

Then, in March when I really ramped up my external sales and fundraising, I started taking notes in Notion.

Notion is a very powerful tool, and I use about 1% of its functionality (probably less). For me, it’s just Google Docs on steroids, but it’s so fabulous at what I’m using it for that I would miss it terribly if I couldn’t use it.

I like it much much more than Google Docs because:

  1. The interface is slicker, particularly the keystrokes (e.g. I type ‘/to do’ and a to do list appears; I type a dash and hit ‘tab’ and I’m making a bulleted list).
  2. I find file storage in Google Docs disorienting: it always feels like a jumble of searchable docs, instead of “here’s everything all in one place.” With Notion, I click on one URL and all my meeting notes are there, easily organized, and well-structured.
  3. Google tracking all my keystrokes and suggesting what I type next wigs me out.

I create one Notion page per meeting, with clear follow-ups, organized in a super-simple week-to-week structure. It looks like this.

Notion Sales Meeting Notes

This has transformed my work in two ways.

The more obvious point is that it’s so clean and organized. Everything is in one place, I know exactly where to find it, and the to-do’s are so black and white (and so fun to check off) that it makes staying on top of everything a breeze. Plus, because of the simple interface, I find myself using it consistently. At the end of a day with 8+ external meetings, I cannot remember what I promised anyone in the first half of the day…thankfully it’s all there in Notion.

The more subtle point is that taking notes during a meeting keeps me more focused. I listen harder and stay fully dialed in, something that can be difficult with hours of external calls every day.

I like this approach so much that I wonder what I’m going to do when in-person meetings come back, since I don’t think banging away on my keyboard with someone right in front of me is going to work.

Until then, I’m totally devoted to Notion, and I think you might like it too.