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.



The Value of Just Deciding

I recently reserved a rental car for a four day trip in January.

The difference in price between full flexibility / cancel any time and paying fully upfront was more than $200. Put another way, I’d have to pay more than 50% more to keep full flexibility.

I can rationalize until the cows come home about why this flexibility might be valuable to me. Something might change! (The weather, my plans, the number of people I need to drive somewhere…)  But the reality is, I’ve already bought the flight and have sunk other costs into this trip, and it’s happening.

Nevertheless, it’s hard to pull the trigger.

The emotional labor of pushing through all of those “what if’s” and just deciding is big. Big enough that I could even put off deciding all the way until January.

In fact, by the time January rolls around, my future self might have forgotten about the $200 wasted. Worse, my today self has an irrational disregard for the well-being of my future self, and is more than happy to have future-Sasha spend 50% more in four months time.

The point, as always, isn’t about the car rental, the odds of bad winter weather, or the fine print.

The point is that for most things, deciding now, and deciding quickly, saves us time and money, and brings with it countless other benefits, cultural and otherwise.

We allow ourselves not to decide by telling ourselves that we’ll know more in the future, and that preserving optionality has real value.

Just as likely, though, is that this is a story we tell ourselves to justify our unwillingness to push through the resistance.

The costs of indecision are big, and they build upon themselves.

Decide today so that you free up your financial and emotional resources for more important things.

25 Keyboard Shortcuts that Save You 5 Hours a Week

Since last week’s post was such a hit, I thought I’d follow it up with a very practical How To on getting faster using your computer.

If you’re a knowledge worker, these 25 shortcuts, once mastered, will save you five of the 10 hours per week that I promised you last week.

But first, a bit of backstory.

This topic has been on my mind because I got a fancy new keyboard a couple of weeks ago. The is a split, ergonomic keyboard, similar in many ways to the very funky Kenesis Advantage I bought 20 years ago.

I bought the Kenesis because I was struggling with the early signs of carpal tunnel syndrome, and, having had a friend sidelined from typing for years by her crippling symptoms, I was not going to mess around. The Kenesis, combined with a trackball mouse that I learned to use with my left hand, solved my carpel tunnel problems, and I’ve been using both ever since.

The only problem with the original Kenesis is that it’s exceptionally ugly…as in, everyone who sees it stops and says “woah, what’s that?!”

Kenesis has, finally, upgraded the color scheme from the original Apple IIe beige, and you can now get an Advantage in a sleeker gray. Still, I was intrigued by the when I saw it on Kickstarter two years ago, so I backed it and was eager to upgrade.

Out of the box, the looked and felt amazing: it was the souped-up version of my old Kenesis, in burled wood, of all things!

But, while the looked familiar, I discovered something terrifying when I plugged it in. While all the letters are in their normal place, everything else (the space bar, the Enter key, Control, Option, Command, all directional arrows, Page Up, Page Down, Esc and Tab) had been moved!

This might not seem like a huge deal…maybe it would impact me every now and then. But since I’m a relentless user of keyboard shortcuts, the new location of this set of keys ground my workday to a halt: while I could immediately type at a decent clip, I couldn’t do a single one of my keyboard shortcuts.

The result was that, for the first day with the, I felt like I was operating at 20% speed when working. I was unable to use keystrokes to switch between apps. I couldn’t easily jump the cursor around, or highlight text, or switch channels in Slack. I was doing everything with my mouse instead, and it was tragically slow.

It occurred to me that this new pace is the pace that anyone who doesn’t use keystrokes has to work at. Terrible!

I was so frustrated, and also so unwilling to give up on my new keyboard, that I resolved to figure out and re-learn the essential keystrokes I use every day.

I’m happy to report that, four weeks in, I’m at about 90% of my original speed, and I’m loving the new so much that I’m going to get myself another one (as soon as they are available.)

So that my pain and frustration don’t go to waste, I thought I’d share my list for anyone looking for more (free) throughput in their workday.

Master these (and, I’m sure, many many more that I don’t currently use but your friends/colleagues might) and you’ll be recapturing loads free time throughout your workday.

And yes, there are plenty of websites with lists of ALL the shortcuts for a given app, but you don’t want all of them, you just want the essential, must-use ones…these.

Managing Text / Cursor movement / Basics

Action Mac Keystroke PC Keystroke
Copy Cmd+C Ctrl+C
Paste Cmd+V Ctrl+V
Undo Cmd+Z Ctrl+Z
Select All Cmd+A Ctrl+A
Underline / Bold / Italic Option + U / B / I Option + U / B / I
Move to next cell in a table Tab Tab
Move to previous cell in a table Shift + Tab Shift + Tab
Move cursor to next word Option + Arrow (R or L) Ctrl + Arrow (R or L)
Move cursor to the end of the line (Word) Cmd + Arrow (R or L) Ctrl + Arrow (R or L)
Highlight next word Shift + Option + Arrow (R or L) Shift + Ctrl + Arrow (R or L)
Highlight full line Shift + Up/Down Arrow Shift + Up/Down Arrow
Close a dialogue box Esc Esc


Moving between Apps

Action Mac Keystroke PC Keystroke
Switch between apps (forward) Cmd+Tab Alt+Tab
Switch between apps (backwards) Cmd+Shift+Tab Alt+Shift+Tab


Gmail (full list here)

Action Mac Keystroke PC Keystroke
Send email Tab, then Enter Tab, then Enter
Add someone to Cc: Line Cmd+Shift+C Ctrl+Shift+C
Add someone to Bcc: Line Cmd+Shift+B Ctrl+Shift+B
Mark an email as read Shift + I Shift + I
Mark an email as unread Shift + U Shift + U
Return to Inbox from msg U U
Add a hyperlink Highlight the word, then Cmd+K, then paste in the URL Highlight the word, then Cmd+K, then paste in the URL


Slack (full list here)

Action Mac Keystroke PC Keystroke
Search channels Cmd+K, then type Ctrl+K, then type
Line break in a message Shift+Enter Shift+Enter
Close a preview file Esc Esc
Add a hyperlink Highlight the word, then paste (Cmd+V) Highlight the word, then paste (Ctrl+V)


Decreasing Time on Task

So much talk about productivity is about how we block out our time.

Not getting distracted too easily by the constant influx of pings that tear our attention away.

Creating dedicated space for deep work.

Managing to do lists, prioritization, deadlines.

And all of this is essential.

We also have the option to create more time in the way we complete our tasks, by finding our own path to efficiency on the things we do often.

Do we type 30 or 60 or 120 words a minute?

Do we spend 15 minutes debating with ourselves before mustering the courage to share our point of view with a colleague?

Does a simple email response to a client question take us 3 minutes to write? 10? 20?

Do our standing meetings last 15 minutes, 30 or 60?

Have we learned both how to listen to the relevant points of view and also to keep meetings moving forward?

These sorts of shifts are easy to describe, but we’re often more comfortable with some than with others. It might help to think of them in four distinct categories, and use these categories to diagnose which types of changes we find easier / harder to make:

  1. Skills: typing speed is just one example. There are tons of tasks we engage in as knowledge workers, many of them repetitive (e.g. switching between applications on our computers). Do we invest the time to learn to do these well AND quickly?
  2. Indecision: ultimately, our day is full of hundreds of decisions big and small. If we hand-wring over too many of these, our day will be gone before we know it.
  3. Emotions: the primary one that gets in our way is fear, the kind that paralyzes us to inaction.
  4. Structure: how long our meetings are, what days we have them, which tasks we do first thing in the morning, how we block our time.

When seen this way, it’s clear how much space we can create in our days and in our weeks, by accelerating the time from start to finish of our important, oft-repeated tasks.

I’d estimate that each of us has at least 10 hours a week we could “find” by taking this all on.

Salesperson Order of Operations

We all have busy jobs and busy days.

Lots of people to talk to, fires to put out, problems to solve.

But if you are involved in sales of any kind (sales, fundraising, business development, you name it), then your must live by this rule:

I respond quickly and thoughtfully when I hear from a sales prospect.

Quickly = within 24 hours.

Thoughtfully = thoughtfully.

It doesn’t matter what else you do, who else you manage, what else is on your plate.

Sales requires attention, prioritization, and responsiveness, always.

So, when that email comes in from a prospect, replying to it is now at the top of your list.

(And a reply could be, “Thanks so much. This is really helpful. We’re on it. We will need two days to answer all these questions. I’ll send you another note then.” That counts as a quick, thoughtful response, as long as the two days really is two days, 100% of the time).

Absent this mindset, and the supporting systems to enable it, you’ll lose out on too many opportunities to be successful.

And remember it’s both mindset AND systems—not one or the other—to deliver on this consistently.


Less Intense, More Frequent

I strained my right hamstring back in April playing squash. It wasn’t too bad at first, and I figured I’d be back to 100% in six to eight weeks’ time.

I spent the subsequent four months trying, unsuccessfully, to fix my hamstring myself.

My approach, as always, was to barrel straight at the problem: intense stretching or strengthening workouts focused directly on the area that hurt.

Four months later, in early August, I had to accept the obvious: my hamstring was no better; if anything, it hurt more.

Chastened, I resigned myself to stopping most of my regular activity and starting physical therapy.

Happily, two months later, I’m finally seeing good progress.  And, as I watch how PT works, it’s easy to see how different its approach is than what I’d been doing.

Everything we do in PT feels more moderate and measured than what I would do. Very little strain, absolutely no pain.

But, miraculously, real gains over time thanks, no doubt, to the consistency of the effort. Week in, week out, whether convenient or not, I’ve been putting in the time, even in the absence of obvious improvement. I’m finally getting somewhere.

It’s easy to make the mistake I made with any new thing we’re trying to learn: we get inspired, decide to “go for it,” and put in a bunch of effort for a few weeks, expecting results. When we don’t see them, or when the novelty quickly wears off, we give up. As in:

  • Vowing to get more organized, finding a new To Do list software, filling the list, and feeling super-accomplished in week 1…and then giving up when the list gets too full to manage
  • Reading a great article about setting aside quiet time in our schedule, crushing it in the first week or two but then schedule a “really important” meeting during that time, and then another, and another…
  • Going to a training about the value of professional feedback, studiously setting up three formal feedback sessions with peers per the facilitator’s instructions, and then snapping back to the old way of doing things
  • Dreaming of becoming a better writer, writing for an hour a day for a week and then being so terrified of the blank page that we close Word, convinced that we tried and we failed.

The too-large dosage, the version of the story where we dive in with massive commitment and enthusiasm, can be part of the problem. This is because big, symbolic shifts start with fanfare but are often hard to sustain. Worse, when our “new thing” requires a lot of effort, we invariably look too soon for results and, when they don’t materialize, we take that to mean something about our ability to learn or do this new thing, and we desist.

The reality of most change is that it is much slower than we expect or hope it will be.

So, in planning to make change, we must ask not only “what is the new habit I would like to nurture” but also “what is the new practice I believe I can sustain, not for a week or two, but for a few months until it becomes ‘the way I do things?’”

Drip, drip, drip.

Changes that become part of who we are happen because we make them part of our lives over a long period of time.

Small, consistent doses make that kind of sustained change possible.

L’Shanah Tovah (Happy New Year)

September 26th to October 5th, 2022 are the Days of Awe in the Jewish calendar, the time between Rosh Hashanah (the Jewish New Year) and Yom Kippur (the Day of Repentance).

As happens most years, I’ve found myself scrambling a bit to remember when these holidays fall, putting them on my calendar and canceling meetings a bit too late, adjusting my schedule so I leave work early enough today so I can get home for a meal before evening services and a day of fasting.

This is all a manifestation of what it feels like, to me, to be a Jew: while I live in community with one of the highest concentration of Jews in the U.S., being Jewish is still something that I have to actively claim, something that is out of kilter with the mainstream.

I talked about this a little while ago with a longtime peer in the impact investing space. In our conversation, one of us said something that made the other realize that we both were Jewish, with similar post-Holocaust histories. From there we shared our stories.

This is a not-infrequent occurrence, because it’s not obvious who is and isn’t Jewish, and, somehow, it doesn’t come up as often or as easily as you might expect.

Indeed, while I’m not proud of it, I’ve made the conscious choice not to talk much about my Judaism on this blog. I take it as a given that the world, and the Internet in particular, is full of lots of crazy, hateful people; and I’ve assumed that anti-Semitism is lurking, just in the shadows, but not far out of sight: 2021 saw the highest level of anti-Semitism on record, a 167 percent increase in violent attacks. So, I apparently concluded, why invite that kind of attention?

I similarly haven’t worked out exactly when, or if, to bring up the fact that I’m Jewish in a professional context. In practice, that means that mostly I don’t do it, which seems normal until it doesn’t—a holiday that I take off; a family story that I share; explaining why I have a Russian first name and a German last name when neither I nor my parents / grandparents are Russian or German. These moments end up feeling like I’m revealing something a little too late, but I’ve yet to figure out a better way to navigate this.

I share all this mostly as a point of reflection: my cultural and religious identities are important to me, and they make me proud. But somehow, I don’t behave as if this is the case, and I’m not sure why.

It could be because there remains, for many Jews, the lurking fear that history could repeat itself, that any society we are part of might turn against us. So, why not take the path of least resistance and lay a little bit low?

And while that thought sounds crazy when I say it out loud, I can think of no better explanation for my paradoxical behavior.

At a minimum, this is food for thought for me tomorrow, as I reflect on the last year and think about the next one.

And, to end on a more positive note, I thought I’d share my favorite part of the Yom Kippur tradition. In our tradition, we believe that while G-d can forgive us for our sins against G-d, only people can forgive each other for sins against people.

And so, we ask for forgiveness from our friends, families, colleagues and loved ones in the days between Rosh Hashanah and Yom Kippur.

So, at the very least, for my sin of omission, I ask for your forgiveness. And, l’Shanah Tova: may you be inscribed and sealed in the Book of Life for a sweet new year.