#108 - Building for the Future: the J-Curve or the Stairs? (Part 1 of 2)

In the middle of 2021, I was heading a small business unit that was building a smart writing assistant. The product was to be available as a web app, a plugin, and an online editor. We were 15-odd and were looking to add a third more.

The people we were looking for were far less specialists or ‘farmers’ who optimized for a more efficient business as usual. These were more of ‘builders’ who would set up a foundation and determine our velocity for the next couple of years.

We didn’t have brand prestige to attract the best talent. On top of that, the world was opening up to work from anywhere following the initial waves of COVID and we had lost our product designer and backend lead to Danish and Silicon Valley startups. At the time, though, I hadn’t read the room.

We had designed a rigorous test for screening applicants but few, if at all, seemed to reciprocate our enthusiasm. It was a seller’s market. That much became clear after a frustrating month or so.

Our product head and I decided to reframe the proposition. Instead of expecting takers to spot a diamond (of an opportunity), we decided to sell the diamond to them.

We took it up like the challenge of assembling the cast for a big production. We pitched the roles. Our product head—one of the first employees at Siri before it was acquired by Apple, and subsequently a founder of an AI startup (that my employer had acquired)—would carve out 15-min slots and pitch 1-on-1 to those whose CV showed promise. I can’t say that the specific intervention resulted in us making better hires, but it certainly helped up our success rate in getting applicants to take our test and give us something more to assess them on.

Looking back, I think we missed a trick. We could’ve used a different frame. But what exactly?

Over the last few weeks, I have come to understand two concepts from elite practitioners from starkly different domains. These two ideas are more congruent than would be apparent at first. And I think these two concepts from very diverse entry points approach the heart of what hiring is / should be about for early-stage startups and 0-to-1 units. Understanding them would furnish answers to the most common points of indecision and questions that come with hiring. 

If this sounds like a tad puffed up, I ask for your patience. Veteran readers of this newsletter will tell you, or at least know, that such thematic matching and lateral thinking is the usual fare for this weekly gathering. I only hope this kind of lateral thinking squares with you. If you’re a founder, business head, or operator, I think it will.

Here’s the first concept. Next week I’ll bring to you the second one, and tie up the two.

Before we jump in, like most weeks, here are the highlights of the piece:

1. The earliest hires are your builders. The later hires are your farmers. The two are—should be—fundamentally different.

2. Early hires should be crazy enough to see opportunities in adversity and push through it without blaming circumstances or colleagues.

3. A J-Curve is a risky career choice with a potentially big payoff. You take your skills and jump into an unfamiliar terrain. If it works, you’ve now proven yourself in another set of conditions.

4. Making a J-Curve leap is an exercise in self-discovery. You figure new things out and you figure yourself out by betting on yourself.

5. The alternative to a J-Curve leap is walking up the stairs. It is linear, predictable, and safer. You may or may not know your limits because stairs don’t test you like a J-Curve does.

6. As a founder or operator looking for builders, you may not always see direct evidence for building in prior careers of applicants. That’s when you can look for broader signals in other domains of their lives.

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What do you look for in a hire for your early-stage startup, for your less-than-30-member unit, or for your tiny 0-to-1 unit? Who can be your answer to a hundred shape-shifting problems that keep you in the weeds every day? Who’ll raise their hand when the team is behind score and it is moments before the buzzer goes off (a launch, a deployment, a crucial client meeting) and say let me make a play?

Someone with eagerness to learn, founder’s mindset, high agency, and so on? Yes, but there’s too much jargon packed in there to be helpful. 

You are, truth be told, looking for someone crazy enough to push through unfavorable conditions without blaming circumstances or colleagues. Nothing less. So, let’s come out and call those attributes like we would in a chat with a colleague when describing a special new hire. Here are a few that come to my mind. 

• Doesn’t wait to be told 

• Makes a habit of considering alternatives

• Wide open to the idea of being thrown into chaos

• Has failed somewhere else before and is open about it

• Has a unique talent stack (think of it like a loose identity)

• Does not actively mind (complain, whine) being put under pressure

• Spends time doing things that’s sometimes hard to explain to a group

• Rejects the way most problems are framed when handed by the bosses 

• Borderline pathological in seeing opportunities in adversity

• Comfortable with being in transition. Permanently.

• Spends a good amount of time mitigating risk

• Willing to revisit beliefs on things held dear

• Learns in themes, not just skills 

Do any items on this list come off as counterintuitive? If you had showed me this list back in 2021, I would’ve raised an eyebrow at at least a couple of items. But today this is more or less what I’m settled on.

Now, I will let you think about it (and please share your thoughts in the comments). But I won’t sweat over that because my object here is something else. It is to introduce to you, curious readers, two seemingly unalike concepts and then show the common thread that runs through them in a way that offers you a helpful frame for making those big early choices in the life of your startup, 0-to-1 setup, or hatchling of a business unit.

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Idea #1: Molly Graham’s J-Curve

Molly Graham spent her earliest years at Facebook on the People team. She then worked on the Facebook phone; joined Quip, a start-up that was later sold to Salesforce for $750m; and was COO for CZI. By her own account those years earned her a reputation as a ‘figure it out’ girl. 

In a recent post on Substack, Graham talks about her approach to career building. She calls it the J-Curve approach and identifies the decision to work on the Facebook phone—a secret project led by investor Chamath Palihapitiya, then Facebook’s VP of Growth, Mobile, and International—as the first J-Curve leap of my career.

What is a J-Curve? Let’s hear it from Graham.

A J-Curve is what I call a risky career choice with a potentially big payoff. It’s a choice where you bet that you can transfer the skills you currently have to a completely new environment and the upside, if you do it successfully, is that you get to prove you are capable of more. 

Graham goes on to shed light on the circumstances that led to her first J-curve leap:

My decision to join the phone project at Facebook felt risky at the time. I knew nothing about mobile, I wasn’t sure we should be building a phone in the first place, and even Sheryl [Sandberg] told me the project would probably die but that I could do it if I wanted to. But then a wonderful friend, Larry Yu, said to me, “You’ve proven yourself on the People team. You know you’re good at that job. Why don’t you go see how actually good you are?”

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Why don’t you go see how good you actually are? 

In my experience, some may find such a question offensive. These are likely the laurel-resters. They’ve been successful before. And it’s a badge they wear dearly. To be clear, I don’t think it’s necessarily a bad thing.

Some others may deflect such a question. Laugh at it nervously. Question its seriousness. These are the fence-sitters. They’re hoping the world thinks they’ve the chops but are too afraid to leap. 

But then there’s another group for whom this is a worm hole of a question. A question with a gravity that is inescapable. This is the kind of personality that is curious about their limits much more than they’re curious about the pay, the brand, the perks. 

And if you’re a history / sports buff, you should look no further than 1984 to understand the true nature of this third breed. That’s the year two athletes in their early twenties started their journey toward greatness. Michael Jordan joined Chicago Bulls as the third pick and Diego Maradona joined Napoli, a middling Italian first division football club. By the end of the subsequent decade, they had not just become the best in the world but also dragged their teams to the very top.  

This is the type of personality you want by your side when you’re starting out with nothing but ambition, be it in sports or in business.

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What’s the alternative to the J-curve?

Graham’s J-Curve visually explains itself. 

I call it the J-Curve because of the trajectory of emotions you go through when you start one of these roles: you leap and for the first 6 months you’re falling until you hit the bottom – you usually feel insecure, stupid, and unsure of yourself among other things. Then, eventually, you realize all that pain was a side effect of learning, and you see that this job has catapulted you to places you’d never dreamed of.

Pic credit: The J-Curve from Molly’s Substack

And what competes for attention with the J-curve?

A steady flight of stairs.

…staying in your comfortable role and getting promoted every 2-5 years, walking up to (hopefully) somewhere great. Growth is slower, but the stairs are a safer bet.

The staircase climbers tend to be worried about failing a lot more than they care about learning. There’s a negative emotional outcome associated with failing. Failure is more than an event. It feeds a narrative and becomes tied to their identity. Often, really smart folks fall into this category. If you’re a straight A through school and college, it is understandable you have the most pride at stake when accepting a new challenge with precarious odds.

Pic credit: The J-Curve and the staircase from Molly’s Substack

It doesn’t help either that the lowest point on a J-Curve is worse than the starting point. It plummets to a pride-swallowing trough. And you hear that in Graham’s words here.

When I took that mobile job at Facebook, for the first six months I felt like an idiot. I went from being an extremely high performer to feeling like a moron all the time. I literally got the lowest performance rating of my life at the end of the first six months.

Once you climb out of that trough…

But then, at around 9 months, I came back from a trip to Taiwan and drew the hardware layout for a cellphone on the whiteboard for Chamath. I remember explaining why the phone had to be a certain shape and being able to defend and discuss my ideas. I walked out of that room thinking, “whoa, I actually know something now.” And that feeling continued. From 6-12 months, I slowly crawled out of the hole and started to feel like myself again. 

What signs should we look for to validate this feeling?

The mobile job ended up being 3 of the wildest years of my life. I got to do hardware, industrial design, operations, product management, and bizdev with really big, complicated partners.

In the end, the Facebook phone was a dud. But the experience was something Graham admits she wouldn’t trade for anything else. By that measure only, anything but a failure.

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What can we look for in our future builders?

Graham’s story holds clues about what we could look for in applicants in the search for our future builders, for our own Molly Graham: Have they failed meaningfully before? How did they react to a prolonged period of poor results? How did their efforts change? How did they manage risk when they were feeling lost?

Sometimes, especially early on in applicants’ careers, I have generally found such a bank of experience to be missing. When that happens, we can search for broader signals.

Molly Graham worked at the National Outdoor Leadership School right after college. She taught their program to college students and adults alike and led 75-day mountaineering and sea kayaking trips in Patagonia and Alaska.

In a later post, she writes:

Working for NOLS and teaching their curriculum was hands down the most effective management training I’ve ever had, and I regularly rely on lessons from that time. 

I would imagine teaching leadership to groups who were out in the wilderness on their own for months on end had Graham develop a healthy relationship with discomfort. It honed her ability to make decisions in volatile situations. She may not have done a thing about launching a phone, but she didn’t need do. She had done so much more.

When you get in situations where you have to make big hiring decisions on little direct evidence, go looking for broader patterns: What’s their relationship with discomfort? Where does their confidence come from—not having been tested or having survived an examination?

I don’t claim to have a tactics playbook to have these questions answered, but the next elite professional I’m going to borrow from may do. Because whether he pulled through high-stakes situations, or not, depended on his ability to make the correct choice.

COMING NEXT WEEK: Part 2 of Building for the Future

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You gave me a few minutes of your day by reading this and for that I’m thankful to you. I’ve always found sharing my thoughts after a period of reading / introspection to enrich the experience. I hope for the same for you. So, tell me what you made of this issue. Hit the comments!