The Zendesk crew is finishing packing needle kits when Vieto, the health services navigator, begins talking about Narcan, a medication that can yank opioid users out of an overdose, which his team has begun distributing to users.

“Do you have any stats on how many Glide clients are using it?” asks Zendesk’s corporate social responsibility program coordinator. In response Vieto tells an anecdote about a woman who seemed lifeless when they found her, barely breathing. A shot of Narcan and she was not only revived but chatty. Soon after, she came by Glide for training on how to administer the medication to others.

An ordinary question; a reply that didn’t quite answer it but was engaging nonetheless. I’d have given this little side step no thought if I hadn’t already discussed with various Glide workers the broader schism it seems to represent.

“We noticed early on that when people from the tech community help, they’re very interested in metrics,” Kyriell Noon, senior director of programs, tells me. “They want to see the data, and they want to know the ROI for their giving.”

“They’re obsessed with impact!” Glide’s James Lin joked.

On its surface, impact would seem a reasonable obsession if you’re sinking time and money into helping people in need. But here’s the thing: When you’re working with layers upon layers of brokenness—when you’re confronting the worst of what our economy can do to people in 2016—the ROI can be minimal.

“Imagine a client who’s doubly or triply diagnosed, someone simultaneously juggling delusion, serious illness, addiction, homelessness, a history of domestic violence,” Noon says. “Just getting this person through a day can be a massively inefficient proposition. It takes someone to pick them up at the shelter, to help them with their Muni voucher to get to a doctor’s appointment, to advocate for them at the appointment, to go to the pharmacy for the prescription and to help them take it, and so on.”

Being pressed for data isn’t a big deal, Noon says, and in a way it’s been a helpful nudge for the team to log what it can. But for all the measurable success of a program like a needle exchange, some of the most ambitious efforts at Glide move the dial in no immediately recognizable way. That can be a stark reality to absorb in an industry whose very existence is premised on transforming the world. In a way, Glide has become a lab, with the accidental effect of illuminating how tech does and does not approach nontech problems.

Needle kits complete, the Zendeskers are thanked and turned loose. The distribution of the kits falls to Glide’s harm reduction outreach team; volunteers can’t accompany them until they’ve had six months of training. With the provisions that I wear a Glide sweatshirt and generally keep my mouth shut, I am allowed to come along for a day. We set out toward Civic Center, hoisting bins of clean needles and condoms and other implements for reducing harm.

The despair feels comprehensive, a thoroughness of dysfunction abutting one of the world’s great spigots of wealth.

As we walk I try to see these blocks as a new arrival might. In many ways the Tenderloin looks like a movie version of poverty: garishly, baroquely, almost implausibly destitute. It’s not just the many humans lying on the sidewalk (unclear sometimes whether alive or dead). It’s not the overt shooting up or the public psychotic episodes or the guy in a blazer and sweatpants shouting, “Can I get a job? Can I get a job? Can I get a job?” It is the extent of all that. The despair feels comprehensive, a thoroughness of dysfunction abutting one of the world’s great spigots of wealth. The median household income in the Tenderloin was $12,210 in 2013. A few blocks away, in the Financial District, the number was $115,233, according to The New York Times.

All this makes it strange to say that the Tenderloin also feels like a happy place in ways. For the suffering, there’s a warmth here, a distinct conviviality, that stands out against the heads-buried-in-iPhones parts of town. People hang out on corners talking about how last night was or what so and so is up to. The colorful dive bars and funky theater spaces longtime San Franciscans miss? They’re still here. It feels worth noting this, if for no other reason than to draw a clearer bead on a place that can feel overburdened by outsider gloom.

“Harm reduction kits!” the team calls as we walk, and a segment of San Francisco that I’ve only ever seen in the shadows begins to emerge. Some people, lost in private trances, take what they need and drift away. But most stick around and chat. A Don Henley–looking fellow offers an assessment of the mayor. An older woman just out of prison reflects on freedom. The Glide team talks to them all with a respect bordering on deference. If they run out of a certain type of needle, Vieto or another worker apologizes profusely.

At the center of the day’s operation is Bill Buehlman, the outreach coordinator for Glide’s harm reduction programs. He’s a muscular guy with a simmering intensity; everywhere we set up shop, he grins and takes a wide power stance, as though prepping for God knows what—which, in fact, he has lived through. Before coming to Glide he was a user, did time in Texas and California. Many harm reduction workers are in recovery, giving extra resonance to the movement’s mantras, which are Glide’s mantras: No judgment. Unconditional acceptance. Meet people where they’re at.

At one point—in front of City Hall, a gold-leafed, beaux arts beauty—Vieto spots a young man struggling to get a needle into his vein. A phlebotomist by training, Vieto says he is tempted to help him with the injection. If the needle hits muscle rather than a vein, Vieto explains, the guy’s drugs will be wasted, which means he’ll likely engage in even more dangerous behavior to score again. In a way, helping would constitute the full realization of the team’s philosophy: literally facilitating heroin use in order to reduce greater harm.

Tech is always looking for that elegant little fix that leverages a small amount of work to crack an outsize problem. Except when it can’t.

Instead Vieto gives him a sterile needle kit and some wisdom about vein care. As I watch I can’t help noticing an unlikely affinity between harm reduction and tech. Both prefer evidence-based, real-world solutions over blind ideology; both traffic in a clear-eyed approach to problem solving. Meet people where they’re at. If the people aren’t happy with taxis, devise an alternative to meet their needs. Squint and you can see Cecil Williams as an early pioneer of user-­centered design, as it were.

But it’s also easy to see how a tech company could float off in a bubble of underbaked solutioneering, often most markedly in the murky realm of helping. Every few months another app promises to bring tech’s disruptive power to bear on our most intractable problems. Last year saw the launch of ­Concrn, an app that dispatches civilian volunteers to nonviolent crisis situations in the Tenderloin; sometimes the civilians play the trumpet, to bring some playfulness to tense situations. In lieu of meaningful medical intervention, they come bearing water and granola bars.

In his book Geek Heresy: Rescuing Social Change From the Cult of Technology, computer scientist and former tech evangelist Kentaro Toyama writes about tech’s enthusiasm for silver bullets—your poverty-disrupting One Laptop per Child programs, your inequality-leveling Khan Academies. Tech is always looking for that elegant little fix, he writes, that leverages a small amount of work to crack an outsize problem. Except when it can’t. In the most damaged corners of society the problems are so complex and sui generis that the reverse is true: It can take tons of effort to make the slightest headway. It’s a painstakingly analog approach Glide takes. The deepest poverty in the Tenderloin simply can’t be hacked.