Great Questions

When we’re stuck with a problem we simply cannot solve, what we need is a great question.

The funny thing about a great question is that it is often hard to recognize.

It can feel slightly off topic.

Like a critique.

Or even downright irrelevant.

Like the person wasn’t fully hearing us and the core assumptions that we know to be true.

But sometimes, if we’re patient enough or stuck enough, we find ourselves sitting with a great question. It germinates in the back of our minds. We process it in the midst of doggedly re-treading the beaten path to our wrong answers.

And then, if we’re lucky, a eureka moment happens. We see something new. A door opens.

What that perfect question did was poke at the heart of a truth that wasn’t true, a strongly held assumption that was just plain wrong.

Suddenly, the impossible becomes possible.

We can’t predict when these moments will happen, but we can pay a bit more attention to off-beat questions before dismissing them.

How Much Impact Measurement is Enough?

Recently I was speaking with a sophisticated, experienced impact investor. She’s been investing impact capital for more than a decade. Her fund has a well-developed investment thesis and a clear impact measurement system.

This system, as I understood it, thoughtfully looks at preexisting research on social impact: things like whether a particular type of software improves learning outcomes for kids; or whether a given healthcare app results in better patient outcomes. In addition, post-investment, the companies she invests in study the efficacy of their offerings—it’s part of what is required by their (mostly) public sector customers. These studies test whether each company is replicating the results expected from the research.

However, in a few sectors, she’s not easily able to get this deeper data.  In that context, she asked me, “What’s your view? Do we really need more impact data?”

Meaning: in these sectors, they have good background research along with a general indication that the products being sold have a net positive impact on their customers. They just don’t know how those positive impacts translate into changes in customers’ lives. Isn’t that enough?

Why Are We Gathering Impact Data?

It depends, I replied, on why we’re gathering impact data.

If we’re doing it to gather evidence—to prove something—then by all means let’s gather only the data needed to cross the threshold of proof. After that, we should stop.

But what if that is not the right objective for impact measurement? The phrasing, “Do we really need more impact data?” assumes that gathering this data is at best a neutral activity for the business, and at worst it’s burdensome, a diversion of resources, and a distraction.

If this is the case, then managing it down to a minimum is the right thing to do.

Flipping the Question

My view, however, is that it’s high time we flipped her question from, “Do we really need more impact data?” to “Do I know all I need to know?”

“Do I know all I need to know?” about my customers, my beneficiaries, and how they experience my service?

“Do I know all I need to know?” to serve them better?

“Do I know all I need to know?” to create a deeper change in their lives, one that will both improve their well being and make them more likely to be loyal and to recommend my service to others?

We perpetually ask the wrong question because we’ve been trained to assume that social impact measurement will forever be a ponderous beast: large-scale, expensive studies that take years to deliver results. That heavyweight approach, the standard in our sector, is extremely useful in a very narrow set of cases. It’s also almost never the answer for growing, dynamic organizations that are still evolving how their solution can best serve customers.

Stop Taxing Social Businesses

For these sorts of social businesses, social impact measurement must be optimized for learning and improvement cycles. It must move as fast as these nimble, dynamic social businesses. It must feel like customer insights, and not like academic research.

If we fail to make this shift, impact measurement will forever be what it feels like today:  a compliance exercise that is a tax on social business, rather than a way to increase knowledge and insight. (More on this risk from my recent panel at the SOCAP conference)

Because, let’s be real: it’s hard enough to build a business that solves a social problem AND is financially viable. Adding a measurement tax onto that business makes no sense.

Conversely, if social impact measurement can help that business grow, improve, and better serve its customers (and yes, at any point feel free to substitute “nonprofit” or “community organization” for “social business”)…well then we’re really on to something.

A Real Example from Nigeria

Imagine, for example, that your social impact report helped you do real things, immediately. For Psaltry, a Nigerian company that helps smallholder cassava farmers, impact data gathered by our team at 60 Decibels helped Psaltry decide to open three new processing plants closer to customers (they discovered that customers’ earnings were taking a hit due to high transportation costs).  This same impact report uncovered that farmers had cashflow issues. Psaltry is using this data to help them get a loan from a local bank: the data helped them convince the bank of the need for this loan and how it would be used to help farmers. You can read their whole story here.

It’s Time to Stop Minimizing a Core Activity

The point, though, is not about this particular impact study—though the results, and the company’s responsiveness to them, are all outstanding.

The point is to ask ourselves: how have we allowed the data we gather about mission achievement to become peripheral to how we run mission-focused organizations? How have we created an approach to understanding our impact that should be minimized so we can “get on with our actual work?”

To the question, “How much social impact measurement is enough?” I’d give two answers:

One: if you’re doing it to prove something to someone, then gather the least data you can to demonstrate that proof, and then stop.

Two: if you’re doing it to learn, if you’re doing it to serve better, if you’re doing it to listen better, so that you can accelerate achievement of your mission, then I’d be really careful about marginalizing or minimizing it.

Instead, I’d bake it in right at the core.

The Stillness is the Rest

I travel a lot for work. After more that 20 years of these trips, I’ve learned that I have no special abilities at conquering time zones. If anything, because I keep a pretty fixed schedule at home, and try to sleep at least 7 (or more) hours every night, going to new time zones takes a lot out of me.

Things that help me adjust include: exercise, meditation before going to sleep, not looking at my laptop or phone within an hour of sleeping, earplugs, and, if I’m flying East, Benadryl. I wrote a post about these, with a bonus recommendation about the world’s best suitcase.

That collection of approaches notwithstanding, I still often find myself lying awake, either at the start of the night trying to fall asleep, or some time very early in the morning try to stay asleep.

When I find myself sleepless in Seattle (or Nairobi, or Bangalore), I will lie still and do some version of savasana (yoga corpse pose), with the intention of focusing on my breath going in and out. I often count my breaths in a cycle of eight, one breath corresponding to each finger on my hand (thumb, second, third, fourth, fifth, fourth, third, second…and then start again). I mix this with a progressive body scan, paying attention to one part of my body and then the next, focusing my attention on relaxing that part of the body, or feeling it bathed in warm light (Headspace has lots of great guided body scan meditations). Through all of this, I aim to keep my mind clear and not let myself get hijacked by each passing thought.

In truth, all of this helps, but that doesn’t mean it puts me to sleep. I spend a lot of time resetting myself, clearing my thoughts, breathing and counting…and then quietly getting frustrated that I’m both exhausted and awake.

When this happens, one new thought that has helped me a lot is: this stillness, right now, is the rest. My mind is clear, my body is relaxed, and that is what rest entails. It is enough.

It’s a freeing thought that can release me from the goal orientation / failure cycle that trying to fall asleep inevitably entails.

I’m am here.

I am breathing.

I am resting.

And that is good.

The Difference Between Winning and Losing

In any close contest, the line between winning and losing is thin.

In sports, it’s a few points that go to one team or another, a couple of plays that were close, a few steps between being ‘safe’ or ‘out.’

These few moments create one winner and one loser. They last, at most, a couple of minutes over the course of a few hour.

And yet the story we tell ourselves afterwards is about the whole contest: “this time it was different” or “I really showed him,” or “I can’t believe I blew it, I’m no good.”

In our desire to make meaning, our story dwarfs the fleeting moments that were the difference between winning and losing.

It’s the same thing with any close call—job interviews when you’re one of a few finalists, promotions that are right on the fence, a client who says yes or no to a big sale you’ve been working on.

If it was a tough decision, then a few small (maybe arbitrary) things made the difference.

This helps us remember that “I’m so [adjective]” statements aren’t the right conclusion in these situations.

Instead, try out “it was close, and I [did/didn’t] get it this time.”

This mindset helps us focus more on those few clutch moments, the specific, small thing that kept us from winning—this time. It also frees us from unproductive self-criticism (or unfounded self-praise), shrinking the emotion of both the win and the loss.

Then, instead of telling ourselves a big, unfounded narrative, we can get on with our important work of giving it our best shot the next time around.


Stretch Assignments

I may be looking at Ye Olden Days through rose colored glasses…

…but I can’t help but notice a difference in attitudes about work today compared to when I had my first jobs 25 years ago.

Back then, my colleagues and I would talk actively about whether our responsibilities would ever extend beyond making copies, sending faxes, and answering the phone. There was enough clerical work and hierarchy that “entry level” was truly menial. When a superior asked us to do anything that involved thinking, we jumped at it. Non-clerical work was a perk, and when it came our way, it was our job to find time to make it happen: do all our menial work, and do this too. These projects were a chance to demonstrate that we could do something other than stand by the fax machine, and each mini-assignment served as a testing-ground of whether we should be given another useful thing to do.

While there are countless flaws in that old system, the mindset around how to approach “stretch assignments” stands the test of time.

A great stretch assignment is a chance to do something new, challenging, and exciting. By definition it’s beyond our current levels of mastery, so it requires additional time on our part to learn and to get it right.

Often, though, I’m hearing just the opposite (including from job applicants): I can only take on that new thing if there’s a 1-for-1 trade of getting rid of this existing thing.

I don’t think it works that way, at least not in environments that are moving fast and trying to grow: the organization only grows its reach, its scale, and its revenues profits and impact, if the things that make up that organization—software, systems, processes and people—can stretch and grow.

Whether it’s a one-off project or an expansion of our role, the best way to take on stretch assignments is, literally, to stretch: our mental capacity, our willingness to be uncomfortable, the number of hours we put in to make the “stretch” possible on top of everything else that’s on our plate. That means finding time around the edges, whether early in the morning, late in the evening or on a weekend, to get that job done. Hopefully the opportunity and learning are more than worth the trade.

(Better yet, in the process of adjusting to this fuller plate, we often discover a bunch of non-essential things that we were spending time on that don’t require nearly as much polishing).

The reality is, the path to leverage in our job requires us to constantly shift, adjusting to new opportunities and new sets of responsibilities.

Learning the skill of sprinting, and getting adept at shifting and stretching time, is the way that we discover what our maximum output really is. It’s also how we discover where it is that we really shine.

How many times?

I can’t help wondering: will there ever come a day when we skip all the hemming and hawing and just get on with our important, daily work?

Will we ever, finally, manage to completely ignore all our excellent excuses:

The setting isn’t right.

I have less time than I thought.

I didn’t sleep well last night.

A very important other problem is raging through my head, unresolved.

Something aches–my head, my heel, my heart–and there’s no way I can do my best work today.

The pain of noticing how bad this paragraph seems, of how loud the “stop!” in my head seems, of how far away I feel from “the zone, is real.

That familiar mantra, “this isn’t working this time, why bother?!” is running on repeat at top volume. I could just put this off until tomorrow, couldn’t I?

On and on and on and on.

How many times until this all fades away?

I couldn’t tell you.

I’ve not gotten there yet.

But I suspect that the noise never disappears, nor is it my job to un-see it.

Instead, over time and with enough practice, while that noise remains, it becomes something that IS while I continue to DO.

The real secret is this: the IS and the DO exist on different planes. That’s why they don’t need to fight it out, because they can coexist if we just put our heads down and get on with it.

Nothing needs to be vanquished for us to do important work today.

The (false) dream of mastering the world

While I was in temple earlier this week, celebrating the Jewish New Year, I was struck by the words of this prayer:

We are stiff-necked and stubborn; teach us to bend before you.

Convinced we’re right, entrenched in our own perspective, we resist Your call to repent.

Convinced we’re self-sufficient, entrenched in the illusion of control, we resist Your call to humility.

Convinced we can have it all, entrenched in the dream of mastering the world, we resist Your call to wake up.

Today You summon us out of our arrogance, out of rigidity, fantasy, shallowness, self-deception.

Teach us to bend our knees, to bow our heads before the Mystery; to realize our frailty and our finitude.

When I think about the big problems our species has created in the world—most notably the climate emergency and mass extinction, but also the entrenched separations and divisions wrought by income inequality, racial injustice, gender discrimination, xenophobia and all of our manufactured fear of the “other”—I can’t help but feel that much of it is summed up by our collective stiff-neckedness and stubbornness.

The illusion of control.

Our dream of having all the answers.

Our desire to master the world.

Humility is a powerful, subtle thing. We often misunderstand it, thinking it cannot coexist with boldness, determination, and an unyielding belief that we can create something better tomorrow than that which exists today. It can.

Humility is the recognition that we know a lot, but we don’t know it all.

That we can control many things but not every thing.

And that, just maybe, mastering the world isn’t the point at all.

Orwell on Un-slovenly Thoughts

In Politics and the English Language, written in 1946, George Orwell mused, “Most people who bother with the matter at all would admit that the English language is in a bad way.”  Imagine if Orwell had been able to see what unfolded over the next 70 years.

You may not consider yourself a ‘writer,’ and it’s possible that writing doesn’t feel integral to your work. Even so, consider this a nudge to invest in your writing—the yields are broader than you might imagine. Writing is not a narrow skill, like juggling or doing a cartwheel. It is a mirror into the mind: we cannot write clearly and persuasively if we are unable to think clearly and persuasively; and as we move the needle on our writing, we sharpen our powers of observation, analysis and storytelling.

Writing with the intention to change minds hones our abilities—to see what’s around us and develop insights about what we see, to understand the worldview of the people whose minds we aim to change, and to communicate in ways that shift thinking and actions.

Begin by choosing to write more. This is much more helpful than choosing to write well. Trying to write well is the best way to end up not writing a lot, and you cannot write well if you’re unwilling to write poorly. This means finding places to write: that could be investing in making your emails 50% better by making them shorter and more human; or you could sign up for a site like, a private site where you commit to writing every day, just for you.

Imagine having this kind of transparency and accountability about your writing!

Then, stop writing the way we think we are “supposed to” write. It’s hard to pin down when, exactly, business-speak was created (though the Atlantic has a few theories), but the main function of so much passive tense and invented verbs (“downsize” “rationalize” “incentivize”) and catchphrases (“run up the flagpole”) is to obscure rather than to clarify, making your writing worse.

© Scott Adams

Your job isn’t to “increase the frequency of your articulation of stated arguments and objectives through engagement in writing- and writing-related activities,” your job is to “write more often and be more persuasive.” Please, please, write like you speak. We, your readers, want to read something written by another human being, and we experience human-ness when your voice comes across in the words you put down on paper.

To practice, before you hit the “publish” or “send” button, read what you’ve written, to yourself, out loud. Ask yourself: does this come out naturally? Is this how I speak? If not, cut, edit, and replace: remove words, replace words, say things in 5 words instead of 12. In the end, your writing will sound like your spoken voice: clear, simple, natural. Your goal is to express formed thoughts and emotions in as few and as precise words as possible.

Read more. Pick the kind of reading that speaks to you. The more you read the more good writing becomes part of your world. You may even inadvertently start mimicking authors you like, which is fine as a start: over time, your own voice will come out.

In the end, all of this is an investment not just in your writing but in your clarity of thought. It’s a chance to avoid the pessimistic concerns that Orwell describes as the self-reinforcing loop of poor language:

A man may take to drink because he feels himself to be a failure, and then fail all the more completely because he drinks. It is rather the same thing that is happening to the English language. It becomes ugly and inaccurate because our thoughts are foolish, but the slovenliness of our language makes it easier for us to have foolish thoughts.

As we give attention to our writing, we rescue ourselves from our own “foolish” thoughts. Over time, we clarify our own thinking, increase our capacity to persuade, and develop the skill of taking unstructured observations and turning them into clear, structured, persuasive words on the page.

Great Job

If you’re in a position of authority, a big part of most days is being asked for your opinion or approval.

Often, you are what stands between the things your organization creates and your customers. Naturally, an important part of your job is to quality check and do the last bit of polishing: you know the most, you are the most experienced, and you can give it that last distinguishing touch.

While it’s true that you’ll always have something to add, don’t forget to ask yourself:

Where are we in the process?

Is this just a matter of taste?

When is it too late to say what I’m about to say?

And (above all), What is the cost of communicating that, no matter what someone else does, no matter how hard they try, it could always be better?

While you might have two cents to add, some days all you should do is smile, nod, and say “great job.”

This communicates confidence in others, reminds them that they’re also on the hook, and it also lets them know that they, without your help, can create your organization’s best work.

Live Fireside Chat on Tuesday

I will be doing a live, virtual fireside chat tomorrow, Tuesday September 17th at 2pm Eastern Time (New York), part of a series hosted by Making Money More.

If you’d like to listen, you can register here to receive the dial in details for tomorrow’s chat.

They’ve got a great lineup in the next few weeks, you also might want to tune in for:

Hope to see you there.