Can a lack of technical expertise be an asset?

Several years ago, I was recruited for a role in engineering leadership at an established software company. This was curious, because although I’d worked in many roles in tech organizations and had been leading people for a long time, I was not a programmer. But the company needed somebody with solid management experience and an ability to lead a young satellite office; plus, in an org with separate tracks for individual contributors (ICs) and managers, I would be expected to work with senior engineers, not be one. I thought I could probably bring useful skills to the team, but I was actively concerned I’d be laughed out of the company by the actual programmers.

In fact, I wound up developing some of the most mutually satisfying internal partnerships of my career. I’m no longer at that company, but I’ve stayed in engineering leadership. Here are some of the things I learned in that role that might be helpful if you, too, find yourself leading people with more technical expertise than you have.

Software development involves a lot more than coding

This is beyond obvious. You also need design chops! Product vision! Somebody has to sell the stuff! But beyond all those key functional skills, you also need people who have seen the common mistakes software companies make — and some of the possible paths to success. That perspective is key, and surprisingly rare, when it comes to organizing people so that you actually ship things customers want.

For example, one of the most common mistakes companies make is setting software launch deadlines far in the future and insisting on a fixed set of specific, complex features (or, more commonly, an ever-increasing set of such features on that deadline). In a best-case scenario, you meet the deadline but ship something customers don’t use, and you seriously burn out the team along the way. In the worst case, you never ship anything at all, and you seriously burn out the team along the way.

You don’t need coding skills to identify this losing pattern and suggest other ways your teams can approach their work (two possible winners: medium-length deadlines with a variable scope of work; or very short deadlines with a very limited scope of work). Convincing organizations to work differently is hard, and it’s helpful if you can explain why software projects with a fixed complex scope and fixed long deadlines will fail. But that requires understanding software development, not code. If you’re able to influence your organization to work in more productive ways, you’ll be enormously valued by engineering teams and the business at large.

Lack of technical expertise can be useful

First, being a non-programmer helps reduce confusion about roles, and it can give ICs a chance to grow as tech leads. But there are more subtle benefits, too. One handy thing about having limited coding knowledge is that nobody expects you to know much about technology, and you can ask anything at all. That’s cool because not only do you get to learn, but it also gives engineers a chance to teach you things. In an IC/manager relationship, the manager typically has more explicit power in the org chart. By giving ICs a chance to gain status as teachers, you can balance the relationship a bit which creates fertile ground for partnering on day-to-day org strategy and on bigger decisions.

At my last company, a series of reorgs left several internally-focused teams buried in groups whose customers were external. The structure made it hard for them to work effectively, which I recognized not because I was reviewing pull requests (I didn’t even have a GitHub account), but because I could see they shared a set of communication problems. I proposed that we form a new group to house those teams, that we could experiment with serving our coworkers in new ways, and that I could lead the group. The tech leads on those teams were comfortable with me in that role, even though among senior directors at the company, I had the least direct technical experience.

Among the ways I’d developed relationships with those tech leads is that each of them had answered my technical questions over the previous years and had dedicated time to teaching me about our systems. They knew that I trusted their judgment as engineers and that I wouldn’t interfere with their decisions. They also knew, in part from seeing the ways I’d used the things they’d taught me, that I had complementary skills to bring to the group — things like helping them align technical proposals with company goals.

Being technical isn’t a thing

In the weeks before starting that first engineering leadership job, I took a lot of friends out for coffee and asked them all for advice about managing engineers. I got plenty of good tips that basically boiled down to: engineers are people, too, so manage them like anyone else. That was useful to hear.

But much more intriguing was the comment a friend in DevRel at Google made: “Being technical isn’t a thing, so don’t worry about that.” She said it with such confidence, I had to reevaluate the common idea that there are categories of people, those technical and those non-technical. I’ve come to realize that what she meant is that technical expertise is a thing that people develop, not an inherent quality people have. Moreover, expertise is a spectrum — a non-linear one at that — and there isn’t a point at which you’re either technical or non-technical. (Not to mention that it’s counterproductive to discount other kinds of expertise in organizations that need a range of skills.)

Real talk: it’s one thing to understand that idea, and it’s another thing to internalize it. When I left that job for another engineering leadership role, I asked a lot of the people I’d been working with if they had advice for me in my new job. One principal, two mid-levels, and one early-career engineer all separately said to me, “You don’t need to worry about being technical enough. You’re plenty technical.” I was taken aback.

These were people who’d reported to me and had to teach me very basic things, like how a monolith is different from service-oriented architecture, or what React is. And yet, they didn’t think my lack of technical depth was a problem. That didn’t mean it was time for me to stop learning. Instead, it meant that I could approach conversations confident that we could figure out software problems together, each bringing useful questions. It also meant I wasn’t personally lacking as a “non-technical” leader, and it wasn’t helpful to broadcast any suggestion that I was.

Not every organization is a good fit for engineering leaders who aren’t programmers

When I was ready to leave that company, it took a while to find a new role. That’s in no small part because lots of companies want engineering managers to roll deep in code — either because that provides an efficiency in the way they’re organized, or because their culture values a specific kind of technical fluency. That’s fine; in fact, it was a strong signal that those companies weren’t a fit for me. I looked instead for companies that already had separate tracks for ICs and managers. That suggested they were sufficiently mature to value management skills. I also looked for companies that needed engineering managers to lead teams and build cross-functional relationships, especially with Product. Those are all responsibilities that benefit from experience in software — but not specifically with code — and are things I enjoy doing.

Since moving on, I’ve talked often with ICs who used to work with me. They commonly say that they hope we get to work together again. None of them has laughed me off.

Originally published on LeadDev.com, May 2021.

I first did the Great Saunter in 1996-ish, and I first wrote the post below in 2014. I’ve updated it several times since, after additional trips around the island, including 2026.

Every year, I send out a note to NYC friends, inviting them to join me on the Great Saunter — a 32-mile walk around the perimeter of Manhattan on the first Saturday in May. Every year, dozens of people reply enthusiastically, declaring that this year, they are definitely — definitely! — in. Every year, about three of those people actually show up, and all year long, everyone else says that next year they are truly — truly! — going to make it.

This post contains all the info you need to make this the year you really — really! — do the Saunter.

The event is organized by Shorewalkers, and I first tried it, as best I can remember, in 1996 — inexplicably inspired by this New York Times story — when you really needed a guide, because there was no path around the island as there mostly is today. It was a crappy experience. Held on a rainy day, the walk drew about 75 people. Only 13 of us finished, and I was the very last one. I hadn’t trained for the walk, so I developed serious aches and blisters halfway through. I didn’t have any friends participating, so I was lonely. Plus, not only was I thoroughly soaked a quarter of the way into the day, but all the water caused the lining of my hiking boots to disintegrate into tiny, painful shards. I limped across the finish line in the dark, thirteen and a half hours after I’d started, miserable, soggy and alone.

Disliking adversity, I avoided the Saunter for the next decade. But then my friend Marci got excited about it. I do like walking, I do like New York adventures, and I do like Marci, so I gave it another shot. Turns out that walking it with friends on a nice day and with some thoughtful preparation can make the Great Saunter a terrific experience. We’ve done it many years since, and, more important for you, we’ve taken notes about what works. Most years, the notes are so effective, Tony and I finish easily with no pain and feel fine the next day. In contrast, I cannot run a mile.

Herewith are decades of wisdom on how to prep for and enjoy the Great Saunter. (Nowadays, you can also find lots of TikTok and Instagram tips under #greatsaunter; they may not incorporate as many years of experience, but they often offer a visceral sense of what the day is like.)

Before the Saunter

Save the date. Right this minute, click over to your calendar and block off the first Saturday in May from 7a to 8p. (Do not make evening plans, or you’ll be tempted to drop out early in order to go home to rest and shower.) Congratulations: You’ve just done 70% of the work required to Make this Your Year.

Do some training. I’m sure you can find elaborate training plans online. If that’s your jam, go for it. Or do what we do: from February (or even March) through April, schedule training walks of one to four hours approximately once a week. On some weeks, do two training walks; on some weeks, do none.

Start with hour-long walks and work up to four-hour walks. Do three or four of those long walks by the end of April. Boom, when the first weekend in May rolls around, you’re good to go. As one friend says, if you can walk twelve miles, you can do it two more times in the same day.

Incidentally, if you live in NYC, you can do some of your training along the Saunter route: It starts near South Street Seaport and heads clockwise around the island. If you’re traveling during the spring, training walks are a good way to get acquainted with other cities.

Train at a pace slightly faster than the Saunter. What with the crowds (which are now considerable) and the chatting and the bathroom breaks and the eating (see below), the Saunter tends to roll at a 20-minute mile. If you train at a 16- to 19-minute mile, it makes the Saunter feel like, well, a saunter. In recent years, we’ve used apps from Strava, Nike Run Club, and MapMyWalk to gauge our pace. (In previous years, I used Gmaps or a pedometer to gauge distance, kept an eye on my watch, and then did the math to determine the rate we were walking.)

If you use an app that lets you share your location (including Google maps), consider letting friends and family see where you are on the day of the walk. It’s good boost to get a friendly text cheering you on ten hours into the day: “Looks like you’re near Gracie Mansion. Wave to the mayor as you walk by!” (Your family might suggest flipping off the mayor, which can be energizing, too.) As an added bonus, if you have compatriots joining you after the start of the walk, they can find you on the app map, eliminating the distracting and often frustrating attempts to text your way to a meeting point.

Test the gear you’re going to use. I understand from real athletes that everyone knows you’re supposed to train with the equipment you plan to use on game day. Same goes here. Because you start training when the weather is quite different from a May morning, it can be hard to try out the proper lightweight clothes. But do make sure you test your sneakers and a bag that’s comfortable when it’s loaded up. (See below for detailed notes on clothing, bags and shoes.)

Sign up online. Shorewalkers is a lovely group, and if you sign up ahead, they’ll snail mail you your number. Technically, you don’t need to register at all, but I do like supporting this small organization. Also, having a number makes it easier for the thousands of other walkers to spot you and chat; it’s a diverse, friendly crowd, and this can be a real benefit. Plus, you can get a certificate when you finish, though I usually blow that off to go get a milkshake instead.

On the Day of the Saunter (and Some Training Days)

Meet up with friends, preferably chatty friends. The Saunter takes twelve or thirteen hours. They go by much, much faster if you have good company. Marci, Tony and I now have a semi-regular crew of about a dozen friendly people who make some part of the walk most years. (People can, of course, walk segments without doing the whole thing. While it can be nice to have fresh legs join down the stretch, it’s easiest to coordinate at the starting point.) We tend to start the day together but then walk in pairs or triads and reconfigure ourselves as we loosely regroup at bathrooms, bandaid breaks and lunch. Over the course of the day, you get in a lot of interesting conversations, and you get to try everyone’s snacks.

It’s not possible to walk as a pack in Manhattan, and it’s a ton of work to keep track of everyone at each minor stop, so we don’t do those things.

Wear sneakers. Hiking boots are not only overkill for a mostly flat, paved walk, they’re also too heavy for a 32-mile day.

Wear a white t-shirt. The temperature in early May varies a lot, and if it’s sunny and warm, you’re in for a harder day. Plan accordingly. Most of my t-shirts are black, but if it’s hot out, the dark fabric makes a big (bad) difference. If you run warm, wear a light-colored top. Tony also likes to bring a second shirt to change into later in the day, plus a plastic bag to stash the sweaty layer he sheds.

Bring a long-sleeve top layer. It can be cold in the morning and especially in the last hour or two.

Running tights that hit just above or below your knee are generally right for early May temperatures. If you don’t do running tights, wear a layer of bicycle shorts or long boxer briefs or something similar. Without a body skimming lower layer, chafing is an issue. A really unpleasant one.

Wear a hat. You’re an adult. You understand this principle.

Consider a bag that converts. Tony carries a lightweight backpack, and Marci has switched from a small messenger bag to a lightweight backpack, too. But I use a lumbar pack (which is a fancy name for big fanny pack). Although it is not the lightest bag I could carry, I can wear it around my waist so the weight is on my low back or in front, or as a cross-body bag with the weight on either of my shoulders. Moving the weight around really helps prevent aches of various kinds, especially for my back.

Carry your water bottle in your hand. Dehydration is one of the things that will tire you out most quickly and thoroughly. To help you keep drinking, hold onto your water bottle — don’t stow it where you can’t reach it.

Take ibuprofen every four hours. It can only help.

Take short breaks. I find that momentum is key — plus, when I break for more than a few minutes, I tend to get stiff, so I prefer a small number of short stops. In 2026, I didn’t sit at all during breaks and ate lunch while walking. It was a good call; I felt far more fluid throughout the day than most years.

Notably, the bathroom situation changes from year to year, as new parks get built and old bathrooms go out of commission. In 2026, there were a ton of bathrooms heading up the West Side to around 75th St—and then none until 148th St. For the first time in years, the bathrooms at Inwood Park weren’t flooded beyond use. While a couple of the old East Side bathrooms had closed, creating some long, bathroom-less stretches, a few new ones were so appealing, I used them just for the novelty of a nice public bathroom.

But some of them are always crowded, especially during the first half of the day. The hottest tip I can offer on shortening bathroom breaks is that if there are long lines, women and non-binary people can and should use the men’s bathrooms.

Things to bring on the day of (and on your longer training walks)

Sunscreen and chapstick with SPF. Apply early and often.

Tissues. Like Douglas Adams’s towel, these are useful for everything. One key use case: There are a lot of bathrooms on the Saunter, but only some have toilet paper.

A small bottle of hand sanitizer. There are a lot of bathrooms on the Saunter, but only a few have soap.

Snacks, snacks, snacks. I’m pretty sure we gain weight during the Saunter. But it is helpful to feel your pack get lighter as the day goes on. Our crew tends to share food, and we generally bring goodies that can be passed around: a veggie frittata or kugel, cut into squares; a mix of salty soy nuts and dried cranberries; carrot sticks; power bars; fruit leather; cookies; hard candies; gum; and a gooey PB&J for lunch. (The obvious Saunter lunch point is at Inwood Park, and there’s a nice farmers’ market right outside the park, but it doesn’t reliably have lunch food.)

One refillable water bottle. On the Saunter route, there are lots of fountains, so you need only one bottle. One with a squeeze top or built-in straw is easier to use while walking, and it’s helpful to have a ring or wrist strap to hold it.

A first-aid kit (i.e., Ziploc baggie) with: moleskin; small scissors; bandaids of several sizes; blister bandaids; athletic tape; that slithery anti-chafing stuff; nail clippers; nail file; gel foot pads; ibuprofen. Except for the ibuprofen, I hardly ever use any of these things, but people with me almost always use all of them in the second half of the walk.

An extra pair of socks. Actually, I’ve never needed these, but they provide psychological comfort.

Sunglasses. Obvs.

An extra battery for your phone, maybe. I start every day with my phone at 100%, and it lasts just fine for the whole Saunter, even if I’m sharing my location. But if you tend to start low or plan to listen to something for a lot of the walk, an extra battery might be smart.

A little cash. In case you want to buy something from an ice cream truck or other ad hoc food purveyor along the way. This is less relevant every year — but it is still a thing.

Things to leave at home on the day of

Your dog. Tony and I like to debate whether our previous dog, Eggs, a super-atheletic Aussie shepherd mix, would have made it the whole way. (Consensus: On an overcast day, he would have covered 32 miles no problem. But he was anxious in crowds, and he would have nipped other walkers and eaten all of their snacks. Our current dog, a 110-pound St. Bernard/Great Pyrenees mix, would be a hit with other walkers, but has no interest in strolling more than about two miles.) One year — a cloudy year — we saw a Cocker Spaniel do the whole walk. That was an anomaly. We cannot recommend bringing pets to this event.

Your young children. I’m not great at judging kids’ ages, but I’m going to say that I’ve seen teenagers and kids as young as twelve walk the Saunter. I have not once seen anyone attempt it with a stroller.

Your rings. Saunter regular Katherine Klein has pointed out quite accurately that your fingers swell a bit on very long walks, and rings do you no favors.

Two final tips

If it rains, we stay home and catch up on TV. The Saunter will always happen again next year.

I also want to emphasize that fitness-wise, if I can do this, nearly anyone can. I hate running, and I’m not a fan of biking, either. Swimming involves getting wet, which, no. I get completely exhausted and out of breath standing still, watching the marathon stream by my apartment every year. But I can do enough mild training to walk 32 miles comfortably. You very likely can, too.

Though nearly invisible to startups, LPs are higher up the money chain than VCs, and their concerns dictate how venture investing is done. If you’re seeking early-stage or first-time investment — or if you like to complain about VC attitude, which is common among frustrated entrepreneurs — you should understand LPs, because they play a bigger role in the venture stack than most startups realize.

Here’s how it works. Contrary to popular imagination, venture capitalist aren’t just rich people who invest their own money. Instead, VCs, who may or may not themselves be rich, invest primarily other people’s money. To get money to invest, VCs “raise a fund,” which involves touring a dog-and-pony show to convince bigger investors to give them money to gamble on startups; it’s not unlike the dog-and-pony that startups do for investors. A venture fund can be anywhere from about ten million to more than a billion dollars, with the money coming from a collection of institutional investors like pension funds, large foundations, university endowments, and sometimes high net worth individuals (at many firms, the VCs also contribute to funds). The VCs who raise and run a fund are the general partners, and the investors in that fund are the limited partners. (Angel investors, by contrast, invest their own money directly in early-stage startups, and they often behave differently than VCs. An influx of angels in the past few years has contributed to shifts in the VC industry overall — another thing worth understanding, particularly if you’re seeking early-stage investment.)

The LPs who represent institutional funds typically put a very small percentage of the money they manage into venture capital funds, and they expect that percentage to be among the highest risk and highest return of their overall investments. Notably, institutional investors have a reputation for being risk averse. Note, too: A typical venture fund lasts 10 years, which means that VCs and LPs often have relationships that last at least a decade. But that’s just the start. VCs make initial investments from a fund in the first three to five years and reserve the rest of the money for follow-on investments in the successful startups. That means VCs are commonly looking for fresh investment every few years, and they like to go back to their existing LPs. Because their investments won’t actually pay off until later in the fund, they can demonstrate success when their startups’ valuations grow from subsequent rounds of funding. In other words, given their relationship with LPs, VCs have a direct interest in their startups’ taking on additional investment, regardless of whether that’s good for the businesses in the long run. This investment structure is not a secret of any kind, but it’s very rarely discussed among startups.

Entrepreneurs like to do the math to figure out what it takes for a VC fund to pay out its LPs at the rates they’re seeking (the big conclusion is invariably: Wow, a couple of the VC investments have get HUGE for the whole thing to work). So it’s pretty well understood among startups that the kinds of returns LPs are looking for require that VCs invest in startups that can grow very big, fast. But LPs don’t just promise money and then wait for an annual report on how it’s all going. For smaller VCs, they may be in touch monthly. For bigger firms, quarterly. And they ask hard questions about individual investments. One VC puts it this way: “If you’re an entrepreneur, you should know that I’ll have to explain your business to somebody else when you’re not in the room.”

Think of it like this: VCs report to another group of people. Those people care deeply about big returns, they are conservative spenders who like familiar patterns, they hold regular meetings with VCs to learn how their investments are faring, and their relationships can run for many years. If a VC wants to keep raising funds in the future, they have to keep their LPs happy — often for years before their investments start to pay off, which means making investments that the LPs can get behind.

Entrepreneurs understandably get upset when VCs don’t grasp your business’s potential or tell you your idea is too complex. While those things happen, and they’re shitty, it’s not just that VCs are under-informed. It’s also that their LPs won’t support investments they don’t understand. Additionally, to keep attracting LP money, VCs need to put their money in startups that other investors will like down the road. VCs thus have little incentive to try to wrap their heads around your obscure idea, even if it’s possibly ground-breaking. VCs are money managers; they do not exist to throw dollars into almost any idea.

It’s well documented that women of all races and black, Latino and Native American men draw disproportionately little venture investment as founders. Do LPs play a role in that dynamic, too? Because a lot of LPs represent public money and institutions that have social missions, they should, arguably, push VCs to invest in entrepreneurs who better represent the population overall. But if such LPs exist, they are spectacularly rare. In fact, VCs, LPs, and the investors who will jump into later rounds that prop up valuations all hold the same biases that favor a narrow group of entrepreneurs. So while LPs don’t say, “I’m not interested in these Latina founders from companies I’ve never heard of. Get us two white guys from Google!”, VC’s don’t have a particular incentive to invest in startups run by people that others in the venture stack don’t readily recognize as good bets. (Notably, a fairly high percentage of institutional funds are run by white women and people of color. That has yet to have an appreciable trickle-down effect in venture capital, which tells you a lot about both hidden bias and Reagonomics.)

If you are seeking venture investment, you should understand all of this. Not only whether your company can become a rocket ship, which we all want to believe, but also whether you can submit to a grow-at-all costs approach and to taking on additional investment, which involves giving away more of your company. And, if you’re part of an under-represented demographic, know that your company’s story will have to be particularly clear and strong. (It’s also a good idea to understand all of this when you want to complain about VCs; makes your arguments smarter.)

OK, so what if you aren’t sure whether you can grow super-fast, or whether you want to? Good news: VCs aren’t the only game in town. In fact, there are a growing range of options, many of which can be more attractive than venture capital, depending on your company and your disposition (boot strapping, crowd funding, good old revenue, etc.). This gets covered a lot, so I’m going to take a pass on re-writing the wheel. But I will note that if you’re seeking early-stage investment, you should understand the difference between angel investors and VCs, and you should know that seed-stage investors — i.e., VCs who make angel-like investments — are still institutional investors, motivated by institutional concerns.

Once you know the game VCs are playing, you can make a good decision about whether to engage. If you do go for it, read Danielle’s advice. It’s better for you as an entrepreneur when raising investment is demystified.

Disclosure: I currently work on indie.vc, a project within OATV to fund startups that want to grow on their own revenue rather than on valuations.

Special thanks to Ross Fubini and Tony Stubblebine for reading earlier drafts.

Published in Startups, Wanderlust, and Life Hacking

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Startups Almost Never Talk About This — But They Should was originally published in The Startup on Medium, where people are continuing the conversation by highlighting and responding to this story.