The Why before the Why
28 June 2017 | 10:04 pm

Before “Why They Buy” there’s “Why They Shop”

Every company is interested in why people buy their products, but rewind time a bit further and you’ll find even more fundamental insights.

Before someone goes buying, there’s a reason they go shopping.

There are usually a few events that lead to the desire — or demand — to shop. Something happens that trips the initial thought. There’s a spark. This is often when passive looking begins. You aren’t feeling the internal pressure to buy yet, but you’re starting to get curious. Then a second event happens. It could be soon after the first, or months later, but this one’s more serious. It lights a fire. You need to make progress. Now you’re actively shopping.

We discovered four things

Over the past few months, we’ve been interviewing customers to understand what led up to their need to begin shopping for — and ultimately buying — Basecamp. Across the interviews, it turns out there were four common situations that triggered people to actively shop for Basecamp.

#1 “We can’t keep working like this.”

This is what what “We can’t keep working like this” looks like. (Illustration by Jason Zimdars)

We heard stories about inefficient communication. Growth was causing older, earlier, “it used to work fine” processes to burst at the seams. There was a bottleneck — too much stuff was flowing back to one person (the owner, usually) prior to it flowing back out to everyone else. A general sense of “we can’t be the business we want to be tomorrow if we keep working the same way we are today”. Growth was on the way, but they knew the way they were working couldn’t support it. Growth was making things worse, not better. There was too much load, hence a desire to streamline. A general sense of hurriedness, hair-on-fire rushing around to put out other fires. Scattered thoughts and ideas. Fear that something’s going to break at the worst possible time.

#2 “We can’t mess up like that again.”

This is what what “We can’t mess up like that again” looks like. (Illustration by Jason Zimdars)

Unlike the first example above (“we can’t keep working like this”) which mostly anticipated problems up ahead, this situation gets right to the heart of it: Something bad actually happened. They messed up big-time, and that kind of mess up simply can’t happen again. A ball was dropped, a critical deadline was missed, someone forgot something important, something slipped through the cracks. It felt like professional negligence, even though they thought they were being diligent. It often happened because people weren’t coordinated. Lots of talking, not enough coordination. One person though the other person would take care of it, but it never happened and no one found out until it was too late. The client chewed them out. A professional embarrassment. Never again. Time to get our shit organized and together.

#3 “This project isn’t getting off the ground.”

This is what what “This project isn’t getting off the ground” looks like. (Illustration by Jason Zimdars)

Common tale here. Lots of talking, not enough action. Teams may have turned to chat tools, but they’re finding their just running on a never-ending treadmill. They can’t get traction through conversation alone. Or people have enthusiastic “let’s do this!” meetings in person (or via video), but then nothing happens. The desire is there, but the means to gain traction, plan, and organize steps are absent. People may be on different schedules in different locations, so continued real-time meetings or communication isn’t possible. Nothing ends up getting done because they can’t coordinate once they stop talking. They need something that not only brings people together, but something that helps them organize, delegate, communicate at different speeds, and make progress together on everyone’s own schedule.

#4 “How am I going to pull this off?”

This is what what “How am I going to pull this off?” looks like. (Illustration by Jason Zimdars)

This one is all about someone being given greater responsibility. They’re leading people now. It’s big and important, and it’s on them to run the team and get it done right. They’ll need to track work that needs to get done, who’s working on what, what they asked people to do, and the overall status of the project. There’s a lot of coordination and communication required to pull it off. They need to have a clear handle of things so they can report up when their boss asks for an update. Such a responsibility comes with a feeling that what’s coming is going to be overwhelming without a proper process and tool that keeps everyone up to date, informed, and organized. Talk ain’t enough, “I’m going to need a system”.

What this all means

There’s lots you can do with this information. It can inform product development, it can change the way you market the product, it can influence the language you use to describe your product to your customers, it can change where you advertise, how you sell, etc.

But for me, what’s most interesting is feeling the moments, the situations people find themselves in before they’re our customers. It’s all situational. It’s not about this industry or that one. It’s not about demographics, either. It’s not even about the competitive set, yet. It’s all about the situation they’re in, the reality they’re trying to wrangle, and the progress they’re trying to make.

And it’s really satisfying that they turn to Basecamp to help them through such important moments in their business. Basecamp is often second — they’ve tried something else before, or cobbled together a series of tools they stumbled into but fumbled around with. Basecamp’s a graduation moment for them — something that helps them steer their business away from random chaos and towards intentional control. They’re now able to grab the wheel and point their business in the direction they’ve always wanted.

The Why before the Why was originally published in Signal v. Noise on Medium, where people are continuing the conversation by highlighting and responding to this story.

Work culture — important things you can learn from my salon
24 June 2017 | 2:02 pm

I’ve been seeing the same hair stylist for years — Valerie. Not only do I consider her a friend (and of course great at keeping me proud of my hair), she’s full of interesting lessons about business. She’s even recently opened up her own salon. (I’ve written about her and her partner before.)

I was chatting with Valerie about what makes a great place to work. She mentioned two things.

First, Valerie sees so many salons pretending that cutting hair is way more important than other aspects of employees lives, like their family or extracurricular activities. She wants to see salons encourage employees to go after what they want. Whether it’s performing in a band, or auditioning for an acting job, she’s wants an environment that works around the real lives and schedules of employees.

Second, Valerie doesn’t want employees to feel stuck doing a certain thing. Many salons silo their employees. You can only cut hair. You can only do color. Valerie wants her employees to be able to explore any facet of the business they want to learn and get better at.

As Valerie talked to me about what’s important to her, I realized those were the same things that drove my career direction and entrepreneurship goals.

One of the first jobs I had was as a consultant. I was on the road, living in other states 5 days a week. My life at home was completely ignored by my employer.

And it’s not just consulting companies. How many work places expect their salaried employees to work as much overtime as possible for free to help make the founders wealthy?

I also saw how companies stuck me into siloed places. I kept finding myself in positions where I wanted to learn and contribute to more aspects of the business, but didn’t see a path to do so. I didn’t expect my employer to hold my hand, but I felt shut out of even the ability to try and learn.

So when I would switch jobs or create my own companies, my objective would often be to overcome these obstacles.

Now don’t get me wrong. These goals are still aspirational to me as I run Highrise. I’m positive I’m still not the best at executing on these ideas, but I want to be.

I realize employees here at Highrise have important things going on in their lives other their work here. So instead of the typical “end of week retrospective” about work, during our end of week meeting we focus on everyone’s weekend plans and life updates. Or we try to promote and encourage the outside efforts of employees, like Alison Groves’ work to give girls a wonderful environment to learn about business, technology, working together, and more with Girls to the Moon.

I also try to provide an environment where Highrise employees can participate and learn about any facet of the business they want to. Any team. Any project. If someone in engineering wants the raw data to customer interviews or our website analytics to see what drives business decisions, it’s all open to them. If someone on customer support, wants to help with marketing and SEO efforts, the contributions are more than welcome. If anyone wants to sit at the trade show booth with me talking to people, they can. If anyone wants to develop, they can. If anyone wants to design, they can.

I want Highrise to be a place where you can absolutely grow into the person you want to be. I know I can get a ton better at this and hope I can. But if you are looking at building your own company and looking for some advice on the people side of things, those are two big ones that stand out to me.

P.S. Please help spread this by clicking the ❤ below.

You should follow my YouTube channel, where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a no-hassle system to track leads and manage follow-ups you should try Highrise. And if you need a hair stylist in Chicago, go say hi to Valerie.

Work culture — important things you can learn from my salon was originally published in Signal v. Noise on Medium, where people are continuing the conversation by highlighting and responding to this story.

Uber’s CEO is out because of pressure, not some ethical epiphany from the board
21 June 2017 | 2:33 pm

It’s hard to predict exactly how much pressure is needed to affect change, but it’s clear to see when there is enough. And there was finally enough to flush out Uber’s CEO.

But let’s not kid ourselves. Kalanick didn’t get the boot because Uber’s board had some ethical epiphany. They presided over his misdeeds for years. Fat, golden years steered by toxic leadership and fueled by depraved acts.

Now greed has taken a backseat to fear. Fear that the pressure that once seemed so easy to ignore will suddenly drown them all. Flushing out the CEO goes from “impossible to even consider” to “impossible to avoid” in what seems no time at all.

On the board, it probably did look like “life comes at you fast”, but that’s only because they’ve been ignoring a dashboard full of warning lights for years. Blinded by those seventy billion dollar headlights.


No, it isn’t pretty, and it isn’t sincere, but it’s change. That’s what it looks like when the status quo gets a sucker punch from pent-up reality. It wasn’t going to happen any other way.

It’s easy to become jaded in this age of constant, social media outrage. To start thinking that none of it will ever matter. Because it doesn’t, as long as the levies hold. And then the final drop lands, and all of the sudden everything is different.

This is the social equivalent of an overnight success. The one that actually takes ten years to materialize. Uber’s fall didn’t just happen in 2017, it’s been years in the making. Susan Fowler’s expose was just the tipping point.

The important thing to note here is that we don’t actually need Uber’s board to have an ethical epiphany for things to get better. Do you think that United’s CEO suddenly came to realize the prudence of treating his passengers with a modicum of respect because he saw the light? Come on. United, like Uber hopefully will, changed its policies because they felt no choice.

This is how we improve matters. Once the survival of a company, or at least its reputation, hangs in the balance, all sorts of impossible things suddenly become possible.

Pressure works. Every drip counts. Be a drop.

Uber’s CEO is out because of pressure, not some ethical epiphany from the board was originally published in Signal v. Noise on Medium, where people are continuing the conversation by highlighting and responding to this story.

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