Initiative Over Experience

Scott Belsky, co-founder of Behance and author of the Messy Middle, did a fantastic interview on 20VC the other day.

The whole thing is a great listen, but one of my favorite insights is how Scott values initiative over experience, particularly in the startup world.

Startups are inherently turbulent. Your idea about the market need might be wrong. Your strategy for reaching customers may not work. That killer operations tactic you used at your last stop may be outdated. What you don’t know almost always outweighs what you do.

This level of uncertainty means that, no matter how experienced you might be, you almost always have to invent new tactics to solve problems. What matters most in these situations is your ability to roll up your sleeves and get shit done.


Most startup leaders I know pay lip service to transparency.

“We tell our employees everything we reasonably can,” is an all too common refrain. Implicit in this sentiment is the idea that employees just couldn’t handle the full truth. If they knew about the VP of Product’s concerns about product-market fit, the CEO’s worries about running out of cash, or the Director of Marketing’s disagreement with the CTO, they’d be searching for another job immediately. After all, “we need to keep morale up.”

But I’ve never once seen a team that’s unaware of the cash flow problems, the market misalignment, or the healthy (and sometimes unhealthy) disagreements on the leadership team.

They may not say anything, but the team always knows. And little by little, as management pretends these issues don’t exist, the rank and file team members that actually make, market, and sell the product lose faith in the CEO and the leadership team.

The folks at VentureFizz did a great interview with Andy Cook, CEO of Tettra on some of the benefits of more transparency. Check it out.

Product Standups

The real problem with scope creep isn’t missed timelines.

It’s not that it takes too long, or costs too much, though these may be true. The real problem with scope creep is that you lose sight of why you were doing something in the first place.

An engineer adds a feature here, a designer makes some UX improvements there, a marketer requests a “simple” change, and suddenly your MVP has turned into something else entirely. Yes, the functionality is all there, but the analytics are incomplete, the test is muddied, and your team hasn’t validated or invalidated its hypothesis.

Product teams need to be careful to keep their eyes on the prize.

At Hipmatic, we solve this by doing a daily Product Standup. Unlike your typical engineering standup, our product standup focuses less on tickets and blockers and more on the big-picture strategy. Are the things we’re working on still moving us closer to our goals? What’s the best next action we can take to move us forward.

Sometimes these meetings take 5 minutes, and they assure everyone on the time that we’re doing the right things. Sometimes they take 45 minutes, but we course correct before wasting weeks on something we didn’t really need to do.

Does Your Product Matter?

I don’t want a bendable phone. I don’t care about the next generation of wearables. And I definitely don’t need the vast majority of Internet of Things products.

The sad reality is that most products don’t solve a problem, even a tiny one for a small group. They’re just more landfill.

Even in the world of User Centered Design, Lean Product Thinking, and more user data than you can shake a stick at, most companies seem hell-bent on creating useless products nobody’s asking for.

If your job is focused on squeezing that last iota of value out of ambivalent customers, maybe it’s time to leave and tackle something bigger. People are begging for solutions to big problems like these:

  • High-quality, aesthetic housing that everyone can afford
  • Paradigm-shifting replacements for major utilities like fuel, food, water, and internet
  • Transparent, affordable alternatives to traditional health-insurance
  • High-quality replacements for Universities (yes, we can do better than bootcamps)
  • High-trust solution to evaluating the quality/fit of existing products and services

Yes vs. No

Purveyors of conventional wisdom can’t seem to agree if we should say yes to more things, or say no to almost everything.

According to Warren Buffet, “Really successful people say no to almost everything.” According to some respected academics and plenty of self-help writers, there are numerous benefits to saying yes to nearly everything.

Instead of these black and white rules, I’d propose an alternative.

Say yes when you’re in a mode of exploration, and say no when you’re in a mode of execution.

Feel stuck? Not sure what your life’s purpose is? Say yes to any opportunity that could broaden your horizons or introduce you to new and potentially helpful people.

On a mission? Can’t find enough time in the day? Say no to anything that’s a distraction from your core values.

Knowing which mode your in is critical to making the right choice.

Top 5% UX Designers

As Seth Godin notes, extraordinary benefits go to those seen as part of the Top 5% of their fields.

This is as true in UX as it is anywhere else. Perhaps more important, the top UX designers have an outsized impact on the industry and the world at large.

But what do the top UX designers do differently?

Yesterday, I asked some of my favorite designers, and the discussion snowballed:

Here are some of my favorite answers:

Forcing Functions

When you’re facing a particularly challenging task, it can be helpful to incorporate a forcing function into your routine.

A forcing function is any task, activity or event that forces you to take action and produce a result.

Need to stay productive at a meeting? Make everybody stand. Want to cut online time wasting? Leave your charger at home. Having trouble writing enough? The Most Dangerous Writing App forces you to keep typing until the timer ends, or you lose all your work.

When designing the most important steps of your app—or your life—think about ways  to incorporate behavior-shaping constraints.

Why Your Product Needs Research

I’ve lost count of the number of groans I’ve heard when the subject of user research comes up.

Most UX designers hate talking to users, and most non-design executives consider research a navel-gazing exercise.

Here’s the thing though: users don’t care about your product.

They don’t care that your product has better specs. They don’t care that it’s newer. They don’t care that it’s technically or aesthetically superior.

User only care about their problems. They care about the nitty gritty details that make something that should be easy difficult and something that should be fun frustrating. So you’d better understand those details like you understand every frustrating moment of your morning commute. And you’d better have a detailed plan for addressing those issues that you’ve vetted with actual users.

User research isn’t about asking users to evaluate their problems. They may not know what they are. It’s not about asking users to design a solution. If it’s a real problem, they’ve already pieced together the best solution they can.

User research is about giving the entire team enough information to make informed decisions about a solution as if they were solving the problem for themselves.

Unless you can honestly say that everybody in your organization is already empowered with that information, your product needs more research.

Content Discovery is Broken

Content discovery is broken.

Android’s news feed shows the same 5 stories. There’s an entire industry dedicated to helping you find new content on Netflix. Medium only recommends more of the same content you’re already reading.

This is partly because most content is crap. It’s derivative, verbose, and designed more for search engines and recommendation algorithms than actual people.

But there’s also a bigger discovery issue at play.

Today’s AI is bad at navigating the line between novelty and your current interests. While a person might understand that their friend likes Game of Thrones not for its fantasy setting but for its political thriller overtones, most of today’s algorithms default to the lowest common denominator: “people like you.”

Collective sorting was a useful stepping stone. But it’s time for something better.

Disrupting Utilities

GoDaddy has horrible UX and predatory pricing.

Yet GoDaddy, and companies like it, maintained virtual strangleholds on the domain registrar market since the 1990s. Domain registry was a commodity, and companies like GoDaddy the utilities that provided it.

Pundits said the registrar world wasn’t going to change any time soon because registrars needed to mark up Top Level Domain prices because navigating the deluge of TLDs, and ICANN’s stringent rules, was so complicated.

But every industry is disruptible.

In September, Cloudflare announced that it would offer registrar services with zero markup. It would include WHOIS privacy for free. And the experience of using Cloudflare would be nothing like the bloated, complicated process of working with other registrars.

When Cloudflare decided to give away free SSL certs in 2014, they doubled the size of the encrypted web. If Cloudflare’s entry into the world of domain registry goes anything like that, the space will look markedly different by this time next year.

All utilities—power, communication, you name it—are ripe for this type of disruption. All it takes is a company willing to treat commodities like commodities in service of a different business model.