Author: Sasha

The Social Entrepreneur Product-Market Fit Paradox

~ Sasha ~ Leave a comment

OK, here’s one to think on.

Product-market fit is fundamentally about customer discovery.

You get excited about an idea, build an MVP, shop that MVP to potential customers.

You listen like crazy, inevitably discovering that your first idea wasn’t (quite) right, and that your potential customers have other important pain points that a different version of your product could address.

You tweak and adjust and maybe even pivot, until you find your way to an offering that meets a big enough need profitably. Away you go.

Except…

Social entrepreneurs have signed up for a slightly different gig.

In some cases, we are here to meet an as-yet-unmet acute need with a better something. But, just as often, our job is to meet needs that aren’t well-articulated, for which the demand is not well-formed.

It’s possible that our most important job is to shape that demand, to push markets, to find things that don’t quite work (for now) and bring together different actors until it is possible—often in some creative way—to make something that’s never worked before work today.

It’s possible we’re in the market creation business.

So, the question, boiled down to its essence, is: how is discovering product-market fit different for social entrepreneurs? And is the traditional, Silicon Valley version of product-market fit just the narrowest version of demand discovery?

 

Part of the answer, of course, is that we need to discover enough demand to build a viable product in a viable market. That much is clear.

What’s more subtle and tricker is: how do social entrepreneurs engage differently in listening to (potential) customers?

Because the customers surely know what they want today.

But we are in the business of meeting today’s demand while we nurture tomorrow’s demand.

Striking that balance is no easy feat.

Perfect at Recovery

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I loved this perspective on U.S. Open semifinalist Emma Navarro.

Navarro’s longtime coach Peter Ayers knew his charge was a perfectionist even before he became her primary coach when she was 14. Years ago, Ayers charged Navarro to apply that perfectionism in a ‘healthy sustainable way’ by striving for a very specific goal.

‘Here’s what I want you to strive to be perfect at,’ he recalled telling her… ‘I want you to strive at being perfect at bouncing back. Stuff’s going to happen. You’re competing in tennis; there’s going to be adversity every time you play. So instead of worrying about being perfect at a given shot or playing a perfect match in terms of never missing a ball or whatever…let’s strive at being perfect at bouncing back.

I find athletics and physical activity very helpful in pinpointing how improvement happens, and how our psychology helps or hurts us. But this article helped me see that most of my focus has been on versions of Navarro’s perfectionism: how sports can teach us to achieve our (accomplishment) goals.

2024 has been one curveball after another for me. It’s been pretty humbling to recognize where my control starts and ends, and what I can and cannot to be “perfect” at.

Life, like tennis, is full of curveballs. No amount of diligent effort will protect us from disappointment and from falling short—because “we” aren’t falling short, we just cannot always achieve what we want to achieve when we want to achieve it, no matter how hard we try.

If this image from @butlikemaybe reminds you of your 2024, maybe it’s time invest more in how you’re recovering.

And, for my fellow perfectionists, “recovering” doesn’t mean “fixing the thing” it means taking care of you.

Not only will this make for a healthier you, it means that, soon, you’ll be back to full (emotional) strength…and you at your best is unstoppable.

Genius…or Folly?

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I’ve been working hard all summer, and am going to take my foot a bit off the gas these next two weeks before Labor Day.

I don’t have any big trip planned. Instead, I’m going to be welcoming this pup to her new home and showing her the ropes.

Her big sister, Birdie, is excited for the company.

Welcome, Peanut.

Make it Twice as Easy

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If we’re trying to get others to take action, we have to start with the big things.

We need to understand their worldview, the story they tell themselves—about themselves and about status and power. We need to align our narrative to these elements and make them the hero of this story.

Hopefully, we’re getting most of these pieces right most of the time.

But our job is to do more than this.

Our job is to also smooth the path towards action in a million tiny ways. These small tweaks add up to big changes in behavior, and we can practice them all the time. Think of this as the things we do to file down the big pieces, so they snap together.

The purpose of these steps is to make it that much easier to get a person to do what we hope they will do.

And that starts with empathy.

What does it feel like to be them?

What is their day like?

How much of their attention have I earned?

How many steps am I asking them to take?

How easy is it to take these steps?

How obvious is what I’d like them to do?

How much trivial stuff am I asking them to ignore along the way?

So often, we are, unintentionally, us-focused. We give people information in the way we’d be happy to receive it—an orientation clouded by our hope that (of course!) they’re inclined to do what we’d like them to do, so they’ll be OK pushing through these small inconveniences. Things like:

Using language that makes sense to us (including jargon).

Assuming that they have the same context we have.

Thinking that they’ll correctly choose between multiple paths.

Or fill in the blanks.

Or wade through uncertainty and clutter.

Think of it this way: Amazon spent millions developing the patent for ‘Buy With 1-Click,’ and that patent led to billions in new revenues.

If it’s worth that much to them, it’s probably worth that much to you.

So, the next time you’re asking someone to do something—especially if you’re doing it electronically (Slack, email, etc)—take a moment to ask yourself:

“How could I make it twice as easy for them to do what I’ve asked them to do?”

Here are some more ideas on how to do just that (bonus: AI could help every time. The prompt is: “Please make this note simpler and clearer, with a more direct call to action.”)

 

Good Self-Talk, Bad Self-Talk

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Longtime readers know I’ve had an on-again, off-again relationship with swimming.

I was a terrible, terrified swimmer as a kid. About a decade ago, I decided to learn to swim properly. However, because I don’t love swimming, I haven’t prioritized it. Consequently, I’ve improved slowly.

This summer, due to tendinitis in my arm, I’ve been back in the pool a lot. It turns out that doing something 3-4 days a week leads to much greater improvement than doing it once every few weeks.

That’s not the interesting bit.

The interesting bit is the shadow path accompanying the change in my swimming abilities. This path is the narrative I carry about my abilities. It moves independently of my actual abilities. My chart looks something like this:

Two points of note on the graph:

  1. The point of Delusion: Me sitting comfortably at home watching “effortless swim” videos. I feel like I’m learning from all the talk of high elbows and not lifting my head, but I’m not spending actual time in the pool, so my swimming isn’t improving. To note, this point on the graph is the difference between online education and entertainment. (Hint: if you’ve been using a language-learning app for a year and you’re still unable to order lunch in that language, this spot is for you).
  2. Dragging me Down: The pernicious point on the graph. Since I’ve carried a fear of swimming my whole life, at any moment during a swim, I can start noticing I’m swimming. That noticing leads to negative self-talk (“this is hard,” “will it ever end?” “how is my breathing?”) which can ruin a perfectly good swim. It can even make the next swim worse (“I hope that doesn’t happen again.”).

As we work to increase our skillfulness in any area, we must remember that our story and our reality are always interacting. For areas where we have a positive self-narrative, that story sustains us, even through the dips. For areas that have always been challenging, it can be doubly difficult to improve—because we need to do three things: (1) Enhance our skill; (2) Bravely utilize the new skill; (3) Do all of this, over and over again, despite (sometimes) being dragged down by our own negative self-talk.

Examples:

  • [About to walk on stage] “I’m a terrible public speaker”
  • [About to have a difficult conversation] “I hate confrontation.”
  • [Facing down a blank page] “This is so hard. What if I have nothing to say?”
  • [About to close the sale] “What if they, like the last person, say no?”
  • [Working on listening better] “How do I show them that I’m smart enough to be here?”

Every time we let our old, negative story infect our new reality, we perform a little worse. That’s OK, it’s part of the process. It’s also why all writers’ advice on writing starts with a version of Anne Lamott’s reminder to just put our butt in the chair and keep it there.

If we relentlessly keep showing up to do the new thing, our persistent work will always win the day. Our doubting voice may appear from time to time, but its power diminishes and, eventually, evaporates in the face of overwhelming new evidence.

“I’ve done this so much, it’s clear that I’ve become good at it.”

Next stop, greatness.

Podcasts Not Panels

~ Sasha ~ 3 Comments

I have, in the past, argued that the only justifiable format for conference speakers is the TED-style talk.

I’m officially reforming that view. The reality is that many potential (great) speakers are going to shy away from that. The stakes are high, as are the requirements for preparation. And it is, honestly, intimidating.

However, I still find panels at conferences infuriating nearly all of the time. They are, by design, superficial, and time after time I feel like I miss the chance to really learn from each of the amazing people on the stage.

The much better option is staring us right in the face: podcasts.

Most podcasts have guests, and nearly all of these have exactly one guest. The format is well-established: a great interviewer has prepared well to interview that guest, and she spends, on average, 30 to 90 minutes having an engaging conversation with that person.

We know that this works because it’s been tested in millions of podcasts, and because all the most famous guest-oriented podcasts have just one person on at a time.

If you’re not convinced, imagine this:

In a stroke of innovation, your favorite podcast is switching things up! They’ve invited not one but three amazing guests onto the show. And they’ve capped the conversation at 30 minutes. So, after introductions and a word from our sponsors, each guest has, if everything goes well, about 9 minutes to share their story. AND (bonus!) it’s up to the guests and the interviewer to try to highlight the unique insights and stories of each of the three guests and to weave together what they are saying into a coherent whole.

I’m pretty sure you’re not tuning in to that, and that you’d think “darn, couldn’t we have gone deeper with just one of them?”  Couldn’t we have really dug into where that one amazing guest is coming from; to learn their perspective on an important topic; to hear their take on everything from current events to how they manage to stay inspired through decades of tough work and ups and downs? What are their quirks, what makes them tick, what do they uniquely have to share with us today?

Yes, that would be much better, on a podcast and on the stage of your next conference.

There are two main reasons this doesn’t happen.

First, because it’s easier to do things the same way. No one will get fired for lining up a bunch of 3-people-plus-a-moderator panels, and trying as best they can to make them good.

Second, and more problematic, because the incentives for conference organizers are all wrong. Their first job is to get people TO the conference, and they do that by securing lots of brand-name speakers.  Lots of smiling faces on your conference website / emails sell tickets. And, the experience at the conference is better for everyone if people at the top of the food chain are roaming the halls.

So, here’s how you split the difference.

  • The core of your conference is 1-on-1, podcast-type fireside chats.
  • Some of these are live, many more are pre-recorded. Market them all as part of your conference.
  • Open up the stage for classical keynote presentations: 18-minute TED talk style, or similar.
  • And, finally, create slots for 3-minute “what I’m passionate about” talks. Three minutes to say one thing you really care about, professional or otherwise. Here are eight of them that are memorable, and one more dollop of genius called If I Controlled the Internet by Rives.
  • Open these 3-minute slots up to your would-have-invited panelists and to your audience, asking for 60-second video auditions that are accepted up to 24 hours before stage time. Music is allowed.

Have at it. And, please, write me directly if anyone complains how much they missed the panels.

7 Minutes

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I got on a call with my company lawyer the other day. I had one very specific question.

The call lasted exactly 7 minutes.

As I hopped off the call, I wondered if he was going to bill me for his time. It was just 7 minutes, after all.

Except that he told me to do the opposite of what I’d planned.

Except that he can only solve this problem in 7 minutes because he’s been working at this for 30 years. Three decades of honing his expertise, knowing the topic, understanding the nuances, and developing pattern recognition across hundreds of clients

We never think of paying artists by the minute—it’s obvious that a virtuoso is so talented only because she’s been refining her craft for tens of thousands of hours.

And yet we let ourselves get anchored to undervaluing our time and effort, thinking about things like “cost-plus” as a starting point for what we should charge.

We, too, have spent thousands and thousands of hours becoming expert at what we do.

That’s why the value of our time isn’t measured in the number of minutes we devote to this task, it is measured in what our skills and insight allowed our client to do: costs avoided, paths (not) take, opportunities won.

Don’t sell yourself short.

And don’t think of your billing in terms of time, think of it in terms of value.

“This is what I’m creating for you. It hits this standard of quality. And I stand behind it.”

As they used to say on the Mastercard ads: Priceless.

The World’s Worst Boss

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It’s you.

You are the voice inside your head, saying all those negative things.

You are the one amplifying your greatest fears.

Dwelling on your mistakes.

Focusing on your flaws.

Doubting whether you have what it takes.

Repeating again and again that your shortcomings are all that really matter, that you shouldn’t even try to play big.

You would never stand for this with an actual boss.

If a friend told you they were being treated this way, you’d be outraged.

So, when are you going to fire you?

Because you deserve better.

You deserve a voice that emphasizes all the things that come easily to you.

The things that we know we get every time we interact with you.

Your strengths, your wow, your moxie, the things that make you shine.

“That was really great, amazing job, I’m proud of you,” is not the first half of the sentence, it is the whole sentence.

Take a moment, write them down, paste it somewhere.

Five great things about you.

Personal-ish

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A few days after completing an insurance claim for my dog, who had knee surgery three weeks ago, I got the nicest email.

Subject: Checking on Birdie

Hi Sasha,

We were wondering how Birdie is recovering from her major leg surgery? We’re sorry to hear she had to go through that and send wishes for a quick recovery!

Please send a quick email letting us know how she’s feeling and give her a great big hug from us!

This pretty much blew me away. Not only did they reimburse me for the surgery, they actually care!

So, I replied. It’s been a stressful time, and I was touched that any company would even bother to ask.

Hi Leslie, it’s a big surgery but she’s coming along all right, thank you. 10 days in and she is walking with a limp and annoyed at her confinement!

And in reply I got:

Hello,

Thank you for your email. We’ll review your claims submission and contact you shortly.

Please visit us online for Frequently Asked Questions and answers about the policy at…

Cue the record scratching and the music stopping.

Here’s the thing: there is no such thing as “personal-ish,” it just doesn’t exist. There are two and only two paths:

The path of efficiency: in a modern, email-driven world, what we care about is a scaled approach that will work enough to hit the bar on our ROI calculations.

The path that’s personal: your experience matters to us. There’s no math to be done because I can’t calculate the value of trust on my spreadsheet.

Now, there’s an interesting question that emerges in the world we’re just entering. Soon, AI will be able to create an experience that feels personal but isn’t. It will walk and talk like trust-building at scale.

I don’t know how we’re going to manage through all of that.

How soon until we cross the uncanny valley, when we can no longer tell the difference between something that was programmed to act like it cares and human caring? My guess is that we will manage to give more people the experience of feeling trusted, and, when we see the wizard behind the curtain, the sense of betrayal and disappointment will be even larger, unless we are very, very transparent.

Regardless of how AI plays into all of this, if the last 30 years have been any indication, there will always be a space for personal—not in spite of its inefficiency but because of it. Raising the ante on trust, doing something surprisingly wonderful…these are the things that make you stand out.

And if you’re like the person at my pet insurance company who had the idea to make something personal, but then couldn’t line up the ducks to deliver that experience, your job isn’t to accept that something’s better than nothing.

Your job is to say “there are only two paths here, we have to pick one of them.”

The Manager Self-Projection Trap

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Many years ago, in my early days as a manager, I remember taking pride when I read, in 360 reviews from my employees, “I can tell that Sasha really cares about me as an employee.”

To be sure, that was good news: I did (and do) care, and I want the people around me to experience that.

But I’ve also come to realize these comments could have reflected that I’d fallen into a trap—the manager self-projection trap.

This trap is fueled by our righteous commitment to fix the past wrongs we’ve experienced.

“Now that I’m finally managing other people,” we say, “I’m going to do this RIGHT. I’m going to manage people the way that I’ve always wanted to be managed!”

Yet another troubled path paved with my own good intentions…

Hopefully you see the pitfall: the way I wanted to be managed was not the way everyone wanted to be managed.

I wanted strategic alignment, clarity of success criteria, and lots of leeway. I wanted to figure things out for myself. I wanted space to be creative. I wanted tons of empowerment and not a lot of direction.

For the 20% of people I managed who also wanted this, I was an awesome boss. For everyone else, not so much.

What each employee needs is specific to them—both stylistically (e.g. directive vs supporting behaviors) and for the tasks they’re working on. I describe this in more detail in Can Can’t Will Won’t and 3-D Management.

Since a good 2×2 is the answer to…everything…here’s one to help you think about whether you’re giving your employees what you want or what they need.

It’s obvious that the bottom left corner is a terrible place to be: you’re basically giving the employee nothing (either of what you value or of what they need) and are doing a terrible job as a manager.

And the top right is nirvana: you’re showing you care, you’re consistently giving the employee what they need to succeed, and you’re being your genuine self as a manger by giving the special things that matter to you too.

The top left is a funny one: hyper-personalized support that doesn’t emphasize what the manager values. This works from an effectiveness standpoint, but I wonder if, over time, there’s less blending of styles and values between manager/managee here.

The bottom right is my “aha” moment, the place where I think I was when I was hearing  “I can tell Sasha really cares about me” but not “I feel like I’m getting the support I need from Sasha.”

What’s hardest about this quadrant is that the employee is not getting what they need, but they are experiencing you trying really hard to support them. And, the harder you (manager) try, the more complicated things become: you’re giving them more of what you would want if you were them, and, because they see that effort and will, they might be less willing to say “that’s great, that’s really kind of you, but it’s not what I need.”

For example, say you’re a supervisor who feels you never got enough praise for your good work. You start supervising a super-high performer, someone who is very ambitious and whose top goal is to get better, and who came from a culture that valued “radical candor.” When they finish a project, you might spend all of your energy highlighting, with highly specific examples, the things they did that were great, without giving them actionable ways they can improve.

You’re doubling down on giving them heaping portions of what you value. I’m sure they appreciate that, but they’re not getting what they’re seeking. Worse, because they can see how much you care, they may struggle to articulate why they feel something is missing. They might even be struggling to know exactly what they need…they just have a vague sense that this isn’t sufficient.

This loop is subtle and it’s problematic: a place where relationships are strong, where employees feel themselves getting lots of care and attention, but, ultimately, something is falling short.

If any of this resonates with you as a manager, some simple questions can shed a lot of light. The next time you are giving feedback to an employee, ask them:

  • Of the feedback I just gave you, can you tell me what of it you find most helpful and what is less helpful?
  • More broadly, are there areas you’d like me to focus more on, others you’d like me to focus less on?
  • My goal is to help you succeed more—are there examples when I’ve really gotten that right that we can build on?

While it’s likely that you and your employee won’t come up with perfect answers to these questions, they are the start of a different conversation. This conversation is essential, and it will be different for with each member of your team.

This exploration will set you down a different path, one in which you are grounded in increasing clarity about what each of your employees need, both in general and for different topics. With this in mind, your job is to start adjusting towards the kind of input they want…even if that feels difficult or counterintuitive for you at first.

Don’t worry about that reaction, and stay the course!

Remember, great management isn’t about being the manager we always wanted—it’s about being the manager the people around us need. More often than not, that’s not the same thing.