Expertise Paralysis

It’s such a treat to find the right person to help us on a tough job.

Someone who has been there and has done that, who understands our context with all its nuances, who can insert herself seamlessly into this tricky situation and move us forward while making us better.

This expert might be a designer, a professional coach, or a mentor. She might be a software developer, a systems architect or a professor.

She accelerates our work, teaches us things, and moves us down our path.

And, if she’s good (and it sounds like she is), we grow by being in her presence. We learn more about what questions to ask, about how to see the whole playing field, about what’s is and isn’t important in making these kinds of decisions.

But let’s NOT let her excellence slow us down or, worse, stop us completely.

She’s here, right now, but she will be gone, sooner or later. And we can’t let her presence, and our understanding of her excellence (and the gap between what she knows and what we know), erode our confidence that we know enough to decide.

Not because we’re as skilled or experienced or as wise as she is. But because, after all, these are our decisions to make.

If we don’t make this decision and the next one and the one after that, no one will.

What You’re Worth

It’s not based on how much time it will take you.

Nor is it your opportunity cost (defined as: the value of the work you would have to not do).

And, most certainly, it’s not anchored in what the last person paid you.

Over and over and over again, we undervalue what we bring to the table: the 5, 10, maybe 20 or more years to acquire your specific set of skills.

Combine that with the promise you make: to do this in the way that only you can.

With excellence, of course, but also with care and grace and maybe a little bit of panache.

I see so many professionals underprice their work and then get stuck on a treadmill of not having the time or space to do their best work or find the right next opportunity.

The first step is believing, really believing, in the unparalleled value you bring to the table.

What’s Holding You Back?

A senior Partner at Bain, who I used to work with often, maintained that decision-making ability was the best way to assess the long-term potential and effectiveness of an organization.

According to their research, good decision-making boils down to: speed, effort, quality, and yield. The best organizations make decisions that tend to be the right ones (quality), quickly (speed), with relatively low effort, and that they nearly always turn into actions (yield).

The thinking behind this is: you might do everything else well, but if your organization is bad at making decisions, that’s going to hold you back in a fundamental way.

We can apply this thinking across multiple elements of our organizational DNA, and reflect on things like our:

Decision making

Internal communications

External communications

Who we listen to

How well we hire

How well we fire


Time management

Quality and number of meetings

Management skills



How much we are focused internally

How much we are focused externally

Strength and resilience of our external relationships

Risk management


Each of our organizations is all over the map for this list of attributes—good at some, great at a few, OK at a handful. But, most of the time, one of them is the most important, rate limiting factor for us. One of them is the cultural elephant in the room, the biggest thing weighing us down and sapping the momentum we garner from so much other good work that we do.

As you lay out plans for the coming year, remember: culture eats strategy for breakfast  (meaning: the best laid plans will fall flat if our culture doesn’t support them.)

What’s the one thing that, if you could change it, would change everything? And what are you going to do about that?

The Brand Flywheel Effect

To the casual observer, Oofos look like regular flip flops, maybe a bit on the ugly side.


The main thing that makes Oofos different is the shape of the sole. Because of that shape, and because of Oofos’ squishy material, your foot hits the ground differently from a regular flip flop, with less pressure overall. The pressure  you do feel is right in the middle of your foot. Both your heel and your forefoot are spared. That’s why it’s a “recovery sandal.” (My Oofos were what got me walking again after a bad bout of plantar fasciitis.)

The entire Oofs brand is built around this concept. They’re trying to win as “recovery footwear.”

This brand promise is so much more than a positioning statement. It wasn’t dreamed up after the fact by a branding agency, it is the thing that the company exists to be.

This allows them to ignore Gucci’s $590 GG T-Strap and Versace’s $350 Pallazo Medusa. They similarly don’t care about the latest patterns being offered in a  $34 pair of Havaianas or about being so cheap that they’ll get picked out of the sale bin at Wal-Mart. It’s obvious that none of this is relevant to them.

Because the Oofos brand is about recovery, and because this is so clear and so real, there’s a natural alignment in every activity taken by every person at the company.

Being the best recovery shoe is what the Oofos team thinks and talks about. It’s what they notice in their competitors. It is the axis against which they want to win (and are winning). This clarity of orientation grounds the daily behavior and decisions of every single employee, without requiring minute repeated reminders from anyone.

While it’s true that “brand” is the promise you make to your customers, it is so much more than that.

Brand, real brand, orients your entire team to a set of priorities. It is a north star that begets a self-reinforcing dynamic.

We ARE this means we DO these sorts of things, we NOTICE these sorts of things, we CARE ABOUT these sorts of things.

This orientation explains why we’re going to keep on getting better at the things that matter, and why we’ll do such a great job at ignoring the rest.

Brand creates a flywheel effect, allowing some companies to leave everyone else—the folks who thought that “brand positioning” could come later—in the dust.

What do you stand for?


I’m not a big fan of New Year’s resolutions. I do a lot of goal setting throughout the year, and the turning of the calendar has never felt particularly useful to me for new or bigger goals.

I do, however, enjoy the start of the year as a chance for lots of small tweaks.

These are little, relatively simple changes that make things easier, smoother, or just bring a little bit of joy.

Things like getting summer caps out of my winter hat and glove basket. There was a small layer of them living in the bottom of the basket. I also put winter hats to one side and gloves to the other. This took me two minutes, max, and it’s taken something that is a low-level frustration and turned it into a tiny pleasure. (Hats! Gloves! Separated!)

I also started my day today with overnight oatmeal, made in the fridge. A colleague suggested this to me last April and I’ve never managed to pull it off. It translates into 10 minutes less rushing in the morning, and the oatmeal tastes better to boot.

Tweaks in your physical environment are easy wins: a clean desk; a fresh notebook; better lighting for your Zoom calls; throwing away old shoes, shirts, sweaters that you’ve not worn in a year or more so you can find the things you actually wear.

You can also make tweaks in your schedule: cut all your recurring meetings to 30 minutes max, with longer ones being the exception, and see what happens to your calendar.

I’m also looking for workflow tweaks: my job involves keeping on top of a million different workstreams, and, as our company has grown, seeing all of them has gotten exponentially harder. This week I’ll be playing around with Slack / Notion hacks that put all priority workstreams at my fingertips. My goal is to eliminating the friction of getting from one topic to another.

Of course there are more subtle tweaks as well: spend this week consciously not looking at your phone when you get in an elevator; put a time limit on your social media apps; leave your headphones out of your ears for your commute to work or home; allow yourself to do nothing for 5 minutes a day.

Keep you tweaks light and easy. These are supposed to be fun, quick wins that create physical or mental space.

And while not all of them will last forever (how long into warm weather before I banish winter gloves from that basket?), if you accumulate enough small tweaks and they will add up to a different energy, a different spaciousness, in 2023 and beyond.

How Might This be True?

What do we do when we encounter an opinion or advice we find hard to digest or understand?

A proposal that doesn’t quite add up, yet.

A perspective that is hard for us to embrace.

A suggested course of action that feels unfamiliar.

To start, let’s ignore how these questions play out low trust environments, and instead imagine what we do when the counterintuitive advice comes someone we trust and respect deeply.

For example, I’m reminded the professional coach I worked with for many years.

I was completely convinced she had my back, and similarly convinced that I had a lot to learn from her.

What to do, then, when she would propose a set of things for me to do that felt whacky? A course of action to do that seemed just plain wrong?

In my head, I would kick and scream, convince myself this couldn’t quite be right.

In conversation with her, I would put on a brave face, ask a bunch of questions, and try to figure out why she was giving this crazy advice.

And, in action, I would take a deep breath and do what she suggested.

And, yes, sometimes things went sideways or blew up in my face.

But more often than not, and way more than I expected, things worked out swimmingly.

And, through these surprising outcomes, I’d learn a lot about my incorrect assumptions; the too-narrow field of options I thought were available to me; my many blind spots; my ladders of inference; the huge swaths of the playing field I wasn’t seeing.

Over time, as this cycle repeated itself, it broadened my skills and, eventually, my perspective.

Of course, not all relationships have this particular combination of extreme (trust + competence + benevolence) on the part of the advice-giver.

But surely many of our relationships have some appealing mix of trust / competence / benevolence, one that affords us the opportunity to react differently in the face of surprising advice.

Perhaps, in these cases, we have an option other than to dig in, retrench, fight back, argue our point of view, and cling to our limitations.

Instead, we might ask ourselves:

How might this (crazy idea) be true?

What am I not seeing that they see?

Where are my old patterns not serving me? 

Is this a situation in which, if I act as I always have, I’ll get the result I’ve always gotten?

Our opportunity is to embrace the strength of our relationship over our conviction in our own point of view. If the advice-giver is the person we know them to be, then there must be truth, goodness and insight in this surprising thing they’ve just shared.

We embrace these seemingly opposing forces—what our head wants us to do, what our heart is telling us to do—and then act accordingly.

Is This Us?

In the push and pulls of the marketplace, and the screaming pace of our days, there’s an ever-present question.

Are we proud to put our name on this?

Whether a product you deliver, your website, your social media, or your email comms, it’s always easiest to say, “but we worked really hard on this” and let it get out the door.

When this happens, what we stand for slowly gets chipped away until there’s nothing left.

Are we proud to put our name on this?

It’s rarely any one person’s job to answer that question.

But there’s always the opportunity for anyone to shift a conversation by asking that question.

Are we proud to put our name on this?

The vision to answer this question grows out of a combination of experience, taste, and culture.

The willingness to ask takes nothing more (or less) than courage.

Three Vignettes About Listening

I’ve been thinking a lot about what “listening” really means.

The point of entry is the literal act of paying attention to the words another person says. But true listening is hearing what people are really saying, either through their words or, as often, in spite of what they’ve said.

Here are three stories to get into the multiple layers of listening.

The Parmesan

One night, my 11-year-old daughter and I were standing in the kitchen. I looked at her and said “could you please open the fridge and get out the parmesan cheese?”

I turned back to chopping vegetables. 30 seconds later she was standing in the spot where she’d been, without any cheese.

When I asked her what was going on, it became clear that she simply hadn’t heard the words I was saying—her mind was somewhere else. She literally did not listen.

That’s OK, she’s only 11.

Dogs and COVID

The next morning, she and I took our dog out for a walk, and we ran into an older man coming out of his car with a dog we’ve never met before. The man seemed a bit hesitant at first, staying on his side of the car, but the dogs’ tails started wagging and I assumed everything was OK.

“She’s very friendly,” I said, referring to my dog.

“Oh it’s fine,” he replied, “and anyway, they don’t transmit COVID.”

The injury

My 15-year-old daughter has become a serious runner, and, at the start of the school year, she’d been running 6 or 7 days a week. This included cross country meets on Saturdays followed by 6+ mile runs on Sundays, only to start practice again for the week on Monday.

Three weeks into the season, she got injured. She’s spent the last two months trying to navigate the fine line between recovery and not dropping out of training.

We had multiple conversations about how best to manage the situation, and at various points my wife or I offered to talk to her coach, because we know it can be difficult for a high school kid to speak up for their own needs with adults.

Every time we made that offer, my daughter would resist or shut down.

Until finally, in that moment of silence, my wife said, “We’re not going to tell your Coach we don’t want you to run, and we’re not going to get in the way of you practicing. We just want to share with him what we’re seeing so we can all work together.”

Three levels of listening

The starting point for listening is simply hearing the words people say to us. This is harder than it sounds in our attention-grabbing, device-filled world. It is your version of “that person just asked me to get the Parmesan cheese.”

Beyond that, there’s the basic work of connecting the dots between what people are saying and what might really be on their minds. Outlier, non sequitur comments (“dogs don’t transmit COVID”) are a place to start: “he’s probably not worried about the dogs; he’s worried about himself.” While that particular connection may seem obvious, I’ve watched how literal my kids are in these situations and started to wonder how and when the entry-level skill of “don’t look for meaning just in the words that person said” gets developed. How often do we see the comic book thought bubbles above people’s heads when the speak? I know I was extremely literal for a long time, and that I often defended my non-listening with a version of, “well, if that’s what he meant, why didn’t he say it?” The miss was nearly always mine, not his, in these situations (let alone the extent to which that question is a wonderful expression of white male privilege….)

Finally, we get to the higher-level work: not only tracking both the words being said and the meaning that is unsaid, but finding a way to bring the unsaid into the conversation in a tactful and non-confrontational way. This is the art of shifting a discussion from what is being said to what has intentionally been left aside because it is too difficult to bring up.

This sort of reframing is where real connection and real breakthroughs come from. The experience of someone paying close enough attention that they say out loud the thing we were thinking, the fear that we were nurturing…this act makes a person feel seen in a profound way.

In the end, it is our undivided attention, and the expression of that attention, that are the greatest gifts we can give someone.

What the Fundraising with Mallory Erickson

Philanthropic fundraising is deeply misunderstood.

In its worst caricature, the lowly fundraiser goes, hat in hand, to the wealthy benefactor, asking for scraps from the table for his good-doing charity.

For years, fundraising has been reinventing itself, taking its rightful place at the center of organizations’ missions and as an amplifying force for both community and messaging. And yet, the old imagery still hangs on, holding both the profession and the philanthropic sector back from realizing its true potential.

While I haven’t been a full-time philanthropic fundraiser for more than a decade, the lessons I learned about in that role, about connection, storytelling, and building partnerships, have continued to serve me well in the intervening years. They have informed, among other things, how I approach sales, how I understand high-stakes decision-making, and how I think about building a like-minded community for change.

Recently, I had the chance to reflect on these and many other lessons with the wonderful Mallory Erickson on her What the Fundraising podcast.

In the podcast, Mallory and I talk about overcoming the power dynamics in fundraising, the lessons to be learned from Adam Grant’s Give and Take, and how we can stay grounded in high-stakes conversations. Most of all, we talk about why fundraising is “the work,” it is not something off to the side.

As a bonus, Mallory and I touch on the wordplay between 60 Decibels and 60 Disciples [sic], why social impact measurement has just been as misunderstood as fundraising, and why #listening is the first steps towards rebalancing power and allocating capital where it can make the most difference.


Not Riding the Wave

Our jobs, and our days, naturally have ups and downs: moments that are more intense and stressful mixed in with our comfortable steady state.

These intense moments might be caused by things like:

A client who is upset, demanding, or irrational.

A sales prospect who changes her mind at the last minute.

A piece of code that suddenly stops working

A colleague who is having personal struggles.

A conflict about something important, where neither side shows a willingness to give.

For some people, the heightened state of awareness caused by stress, emotion, and conflict is what they need to perform. Whether it’s an external deadline or interpersonal strife, these folks respond to hard-core external stimuli by drowning out all distraction and do their best work.

But most of us don’t thrive when faced with big external stressors. Emotional ups and downs have real costs, both in terms of the quality of our work and impact on our well-being.

Of course, there are things we can do to minimize how often these difficult things happen. We can fire the bad clients; build a business based on repeat sales; plan and test well when building new features; bring in external experts to support colleagues who struggle; and do group work to invest in solving conflicts productively.

But, try as we might to minimize this hard(er) moments, we cannot eliminate them entirely. As in:

A certain number of clients is going to be difficult.

A certain number of sales will blow up near the finish line.

A certain amount of the software we write will go sideways unexpectedly.

A certain percentage of our teammates will go through struggles.

A certain proportion of professional disagreements will end up in pitched battles.

Indeed, these hard moments are a feature of our lives, not bugs. They arrive with predictable regularity, and, therefore, their presence in our day should not be surprising.

And, if they are not surprising, and they happen with some regularity, at some point we must ask ourselves an essential question:

 Do we have to ride the emotional wave?

 Experiencing these difficult moments fully, remaining present, and engaging completely, is not the same thing as riding that wave.

So, unless riding it helps us in some way, we might consider letting the emotions wash over us while we stand tall and do our best work.

Just because the situation gets heated doesn’t mean that we have to sweat.