How to design products that delight your users with Slack’s VP of design Ethan Eismann

03/25/20 • 56 min

On this episode Abadesi talks to Ethan Eismann, VP of Design at Slack. He has previously worked on flagship products at Google, Uber, and Airbnb, as well as at Adobe back when Flash was still a thing!

In this episode they talk about...

The consumerization of the enterprise and bringing personality to software

“You need somebody who is really able to think of your customers first and who can translate your customers’ perspective into your own unique tone and personality.”

Ethan talks about the trend of the “consumerization” of the enterprise, why workers are demanding better software, and how Slack has played a role in the trend. He talks about how they’ve brought some personality to software that is typically utilitarian, to the delight of millions of users. Ethan tells the story of the pivot that Slack made from being a gaming company called Glitch to a communication tool for the enterprise. He also talks about how one of the early employees helped to shape the unique personality that Slack has today.

The design philosophy at Slack and how they use hypotheses in designing their products

“It’s critically important to have a perspective on what your customers need. They will often tell you where to focus. They have these unsatisfied needs and deep wants and desires. They will tell you the path.”

Ethan breaks down the design philosophy at Slack, explaining some of the unique processes that they use to develop software. He says that they iterate rapidly, and are constantly testing new features on their own live data from their internal Slack channels. He says that they encourage their engineering teams to contribute design ideas as well.

“We try to keep a history of our prototypes and we document the learning that comes along with each prototype. We have a library of the past experiments that we’ve tried and what we’ve learned.”

He explains their process for testing their hypotheses and how they determine what to do based on the results of their experiments. He says that sometimes they find unexpected results which change the direction of their efforts.

“When you're thinking about your product, consider that people only have so many cognitive calories to spend at any given moment. If you have a complex product that could be okay, as long as you break it down into simple concepts that people can consume.”

Customer-centric design and what it means to communicate energy as well as information

“Fundamentally, the companies that have been most successful are the ones that have prioritized their customers. They’re always making time every week to get closer to customers. Having a customer-centric company means that everyone has a perspective because everyone in the company is spending time with them.”

Ethan talks about the importance of listening closely to what your customers have to say. He says that at Slack they are constantly co-creating with their users. He breaks down exactly how they do this, including how they uses shared channels to interface with power users around the world who are always sharing feedback and helping them shape the direction of the product. He also breaks down why communication is not only about information, how they are using things like emojis to communicate energy in addition to information, and how this is allowing workers to express their unique voice.

“Communication is information as well as energy. Software tools are often great at allowing you to create information but don’t always let you express energy. We try to design in a way that allows individual personalities to shine.”

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin, Safety Wing, and Trulioo for their support. 😸

Companies and Products Recommended on This Episode

OP-Z Synthesizer — An advanced fully portable 16-track sequencer and synthesizer.

OXO Spatulas — Designed to serve dishes with comfort, efficiency and style.

Slack Shared Channels<...

In this episode they talk about...

The consumerization of the enterprise and bringing personality to software

“You need somebody who is really able to think of your customers first and who can translate your customers’ perspective into your own unique tone and personality.”

The design philosophy at Slack and how they use hypotheses in designing their products

Customer-centric design and what it means to communicate energy as well as information

Companies and Products Recommended on This Episode

OP-Z Synthesizer — An advanced fully portable 16-track sequencer and synthesizer.

OXO Spatulas — Designed to serve dishes with comfort, efficiency and style.

Slack Shared Channels<...

Previous Episode

How to sell your product to enterprise customers with Michelle Bacharach

On this episode Abadesi talks to Michelle Bacharach, founder and CEO of FINDMINE, a retail technology company that uses machine learning to scale the currently manual and tedious process of product curation. They are a fast-growing company with clients like Adidas, Perry Ellis, and Callaway.

In this episode they talk about...

What led Michelle to found FINDMINE, and how they’re changing the buying experience

“We’re trying to close the information gap between the customer, who isn’t an expert on what they’re buying, and the brand, who is an expert at what they’re selling. The customer gets better information and spends more money and the brand is happier because they make more revenue and they save time."

The inspiration for FINDMINE came from Michelle’s experiences as a shopper. She says that she struggled with buying things that might have looked intriguing at the point of purchase, but realized later that she didn’t have the use for it that she thought she did, or it didn’t work with the rest of her purchases, as with a couch that didn’t match. She says that she started the company to help the people at companies who know the most about products and their potential use cases transfer that information to the buyers of those products. She says that they are using machine learning to hone the marketing campaigns for products and in the process saving time for those selling products and increasing customer satisfaction on the buyer’s side.

“Artificial intelligence and automation are very valuable when there’s a bottleneck of human effort, and we scale out creative human effort. The starting point is a human they set the vision for what this fashion brands stands for and how they define style.”

Her advice for startups pitching big companies as potential clients

“Pitch the companies that you’re trying to land as clients. Maybe one takes a chance on you and if nothing else, you’re going to learn a lot, like what features are important and what the product feedback is.”

Michelle explains how, as a relatively young company, they have landed contracts with so many big-name brands. She explains the process that she used to pitch them, and talks about her key pieces of advice for smaller companies pitching bigger ones. She says that it makes sense to aim for clients that have fewer legal requirements for suppliers when you’re just getting started.

“People don't necessarily always know they have a problem or the severity of the problem that they have or how to tackle it. You can get analysis paralysis from a customer sometimes. When they realize there's a problem, that's half the battle. They may realize we are the solution, but they don't know how to start using the tools.“

How to close enterprise customers

“It’s so funny because our whole mission is to help the buyer understand how to be successful with the product that they’re buying and that’s exactly the same thing that we have to do for our customers. They have less information about how to be successful with our FINDMINE technology than we do and we have to close that gap for them. It’s so full circle.”

She walks through the process of landing a client from the initial pitch to signing the contract. She says that it’s important to educate your customers on the true value of the product to them when they don’t know exactly what kind of problem they have or how to solve it, let alone with new technologies that they may be unfamiliar with. She talks about the value of case studies and why successfully landing just one client can lead to many more.

Next Episode

How to get acquired with Waseem Daher of Pilot

On this episode Abadesi talks to Waseem Daher, founder and CEO of Pilot. Pilot is bringing bookkeeping into the modern age. He has started (and sold!) two other companies prior to Pilot.

In this episode they talk about...

The story of starting Pilot and what Waseem learned from his two previous companies

“The end-to-end solution is really what made the business work. We are going to be your bookkeeper, your finance team, rather than sell you software.”

The story of Pilot goes back to his first company, where they tried to do their books themselves, but realized how tedious it was and how much could be automated.

He explains why he tries to have a more focused approach to company-building now:

“I try to have a better sense of what is actually important. We were so worried about all of the stuff that we thought represented an existential threat but in practice literally zero of those things mattered. Of all the things I remember agonizing about, none of them had any actual effect on the business.”

He also says that he makes sure to take time to rest and recharge, rather than working all the time:

“In the first company we worked all the time, 6 days a week, 12 hours a day. Despite having worked that long, there were Saturdays where I still felt behind so I worked then as well, and every time I did that, it was always a mistake.”

When it makes sense to take venture capital versus bootstrap a business

“There’s a very pervasive and harmful narrative in Silicon Valley that the VC way is the only way to do it. I actually think the VC way is the unnecessarily difficult or hard way.”

Waseem explains how to think about starting a company and talks about the principles to keep in mind when you’re thinking about the risk and reward of different approaches:

“If your objective is wealth creation, you should not start a startup, you should go work on Wall Street or something. The easiest way to make $10M is to own 100% of a company that’s worth $10M, not to own 1% of a company that’s worth $1B.”

He says that “lifestyle is not a bad word” and that as a founder you don’t need to care about serving a massive market unless you’ve taken venture capital funding.

“Venture capital is not right for 99% of businesses. You have to be building something that is targeting a gigantic market to have a company worth billions of dollars doing hundreds of millions of dollars of revenue.”

How to think about a potential acquisition

“By raising a bunch of institutional capital, you’re prevented from taking exits that are otherwise very good or very profitable.”

Waseem shares what he’s learned from two previous exits, one to Oracle and the other to Dropbox. He says that it’s most important to think about how you and your company will mesh with the acquirer and choose the offer that provides the best fit rather than the highest dollar amount. He says that if the fit is good, you will create much more value through the relationship together than the value of the acquisition.

“Look at the acquisition as the start of a new relationship, not the end of something.”

How Waseem stays productive

He explains that he keeps most of his apps on his phone in folders rather than on his home screen. This creates friction and ensures that he has to be intentional about what exactly he is doing when he takes out his phone.

He also explains exactly how to write emails that get responses from busy people:

“Craft something that is really short, that is to the point, and that has a very crisp and clear call-to-action at the end of the email. Ideally the call-to-action is as easy to respond to as possible.”