Talent signaling

An incredulous friend texted me the other day: “when are you guys going to stop putting new hires on the about page??”

She had a point. Navigating almost 600 facepiles is getting a bit unwieldy. I’ve already forsaken the scroll bar (comparable to traveling by Segway) and resorted to CTRL+F.

Interesting question, though.

When should a company stop listing all of their employees on /about? Why would you do this in the first place?

One hypothesis is that in the early stages, startups should pimp their employees—especially if they have A players—because it signals to potential candidates that they’re an attractive place to work with lots of other smart people.

After a certain point, however, the company grows big enough and has enough momentum to attract awesome talent regardless, and the risks of publicizing this information outweigh the benefits. Bios disappear when a company moves from poacher to poaching target.

Rethinking what it means to sell

Word association time:

I say “salesperson,” you say ________?


What’s ironic about these stereotypes is that they’re only true if you’re not very good at your job.

As I’ve shadowed sales calls over the past weeks, I’ve realized that the best aren’t “selling” at all in the traditional sense. In fact, I think the most successful salespeople actually view their job as two different roles:

  1. User researcher

  2. Problem solver  

The first requires the ability to listen, empathize, and draw out the underlying problem that you’re solving for. The second calls on your creativity, resourcefulness, and flexibility.

What this approach highlights is that the foundation of the entire process is understanding the use cases and paint points your product needs to address. Which means most of your time should be spent listening and asking thoughtful questions, not talking. I wouldn’t be surprised if there’s an inverse correlation between number of words spoken and deals closed.

This philosophy is helpful on a tactical level too. When you’re fielding questions or handling objections, try taking a step back to understand what’s motivating the concern. Otherwise you miss a valuable opportunity to gather context; it’s like being asked to pack a lunch without knowing if you’re going on a lazy picnic or an eight mile hike. To take a couple of examples:

Customer: “How much do you cost?”


You: “$795 a year for the first five licenses and $125 for each additional seat.”


You: “Annual billing is our most popular option and that’s $795 for the first five licenses and $125 for each additional seat. Are you looking to replace an on-prem server or switch from an existing cloud solution?”

Customer: “We have an on-premise server at the moment.”

You: “Ok, well let’s do a quick calculation of how much you can expect to save over five years…”

Customer: “I need something that’s more secure.”


You: “We encrypt your files at rest and in transit using the same technology as banks — 256-bit AES encryption and SSL for data transfers.”


You: “I’m happy to talk more about security. Can you tell me a bit more about your specific concerns and what your team needs?

Customer: “Well, we work with a lot of external vendors so the ability to set different access permissions is really important.”

You: “I see. There’s a couple of ways you can do that with Dropbox…”

Wearable optimism

Some observations after ~2 weeks wearing the Fitbit Force. Overall, I’ve been surprised by how quickly it’s impacted my day-to-day habits.

1. Favorite feature is the combo of the sleep tracker & silent alarm. I can now turn my phone off when I go to bed since I don’t have to rely on it to wake me up. Having the entire world at your fingertips is generally great but not conducive to falling or staying asleep. And the simple action of turning on the sleep tracker has become a powerful trigger for “go to sleep NOW.” Amazing how quickly you can focus your attention on improving something once you start measuring it.

2. When I’m stressed or thinking through a problem, I’m more inclined to duck outside for a walk instead of raiding for snacks.

3. If you’re thinking about buying an activity tracker, I’d encourage you to gift a few to family and friends at the same time so you can start tracking together. Seeing how you stack up adds an extra degree of motivation. Who knew virtual taunts could be so much fun?

How to disagree constructively

I’ve been in my fair share of meetings and have noticed that the best collaborators and leaders do one thing especially well: they know how to disagree constructively. That is, they can express a conflicting point of view in a way that moves the conversation forward and keeps the focus on the ideas instead of the people.

This skill also happens to be one that less effective communicators stumble over frequently, either by failing to voice their opinions assertively enough or bruising egos and their reputation along the way.

Liane Davey recently wrote an article in HBR with actionable advice for improving how you communicate a differing perspective. The key recommendations are:

1. Use “and” instead of “but.” It’s not necessary for others to be wrong for you to be right. Rather than try to override someone else’s idea, just add your reality. For example, “You think we should do X and I’m proposing Y. What are our options?” This engages your teammates in problem solving instead of competition.

2. Use hypotheticals to get people imagining a different scenario. This is especially effective if people don’t seem receptive to your ideas. For instance, “I hear your concern about XYZ. If we could address it, what could the campaign look like?”

3. Focus on the underlying goal. When you disagree with an idea, start by trying to understand what’s behind the suggestion. For example, “I’m surprised you suggested XYZ. What’s your aim in doing that?” Many conflicts arise over approach as opposed to the end goal. If you can agree that the problem you’re both trying to solve is the right one to prioritize, that’s common ground to start looking for a solution.

4. Ask about the impact. If you have concerns about a plan of action, ask people to think through the impact of implementing it. For instance, “How will this launch affect XYZ?” The key here is showing that you’re genuinely open to ideas and curious about the right approach.

5. Ask for help. If something really catches you off guard, be a bit self-deprecating. For example, “I think I’m missing something here. How will this help us with XYZ?” Be careful that your questioning doesn’t come off as insincere or leading. As with #3, people can quickly sense whether you’re making a real effort to understand someone’s reasoning.

360 feedback experiment

Inspired by this Quora post, a friend and I decided to reach out to people whose opinion we valued for feedback on our strengths and weaknesses. Here’s what we asked:

  1. What role does Alice play in your life? (How do you know her)
  2. What is Alice good at? Describe her at her best.
  3. What are some ways you’d love to see her build on these strengths?
  4. What is Alice not so good at? Describe her on an off day.
  5. What are some ways Alice can improve on her weaknesses?

What I learned

Three themes that came up most frequently in my off day feedback were: being more assertive, dealing directly with conflict, and handling unmet expectations. Alice and I actually shared a lot of the same areas for improvement and I was kind of disheartened to see how much of it broke down along gender stereotypes.

Most of these were things I knew in the back of my mind but hearing them crystallized by others makes me feel empowered to “get an ounce cockier,” as someone put it. It was interesting that more than one person pointed out I could benefit from behaving in what feels like an extreme way but that won’t actually be extreme at all.

Things that surprised me

Going through Alice’s feedback, I was surprised at how consistent the comments were after just a few (~3) responses. I imagine most of us think that only our family and closest friends see certain sides of our personality. The reality is that though the degree to which we express them might vary, our quirks and inclinations are relatively stable across contexts.

The majority of the feedback focused on the “how” rather than the “what”. Less of a surprise, but I was still struck by how strongly the comments skewed towards approach as opposed to accomplishments. How do you make people feel when you’re around them? What’s your process for tackling problems and disagreements? It got me thinking that there has to be a better way to incorporate this qualitative measure into the job application process.


Make sure your list of people includes a range of perspectives. Some dimensions to consider: relationship (friend, family, coworker, mentor, etc.), how long you’ve known the person, gender, and age (older points of view can be especially insightful).

Per the consistency point earlier, you really only need a handful of insightful responses to start seeing patterns. Alice and I had between 15 and 20 people on our list and a ~55% response rate. Some ways to improve this percentage:

  • Give people a heads up this is coming…so your dad doesn’t ask your friend if the experiment is real after the second reminder email (oops).

  • Insightful comments take some reflection. Allow two weeks for people to send in their thoughts.

  • We probably could have cut questions three and five as a lot of people ended up answering them in their responses to two and four. Additionally, while many of the suggestions raised were actionable, you’re going to be the best judge of what next steps make sense in your situation.

Use this as an opportunity to test your self-awareness. Write down what you think are your biggest strengths and weaknesses and see how it compares to others’ perceptions.

If you’re interested in giving this a try, here’s the email we sent and a spreadsheet to track responses. Would love to hear what you learn!

Dessert, video games, and excuse my language

On Thursday I attended a web development workshop put on by Girl Develop It. The audience, naturally, was all female. We started the session with a round of introductions where the last piece of information we were prompted to share about ourselves was our favorite dessert.

The next day, I went to a JavaScript workshop sponsored by Code Fellows. The event was open to everyone but the room was probably 80% male. When it was time to introduce the concept of JSON, one of the instructors launched into an extended Legend of Zelda metaphor. I realize that’s pretty mainstream as far as video gaming references go, but there was a level of understanding and satisfaction that escaped most of the women in the room.

Both Girl Develop It and Code Fellows are spearheading wonderful initiatives to promote programming literacy. My experiences this week just reminded me that gender imbalance in either direction comes at a cost. Sometimes the trade-off is worth it because it creates a welcoming environment for people to pick up valuable skills. And other times a lack of representation can lead half the population to think that programming isn’t for them. I hope some day in the near future I’ll attend a coding event where I’ll find points of connection with my peers and be challenged by a diversity of perspectives.

On a separate but related note, I’ve never understood that moment in a conversation when a guy turns to the women in a room and prefaces a curse word or other colorful phrase with “Excuse my language…” before breezing ahead. What’s the point? To preempt my ability to be offended? If you’re really worried about upsetting me, find another way to express yourself. Otherwise, just treat all of your listeners as equals. Not all men are crude conversationalists and not all women are sensitive ingénues.

The useful answers are always the more forgiving ones

I spend almost eight hours every week commuting to and from work on the bus. (Not ideal, I know).

Most of the time I actually don’t mind the opportunity to read, nap, or just think. And most days, I’m free to do exactly that. But public transportation necessitates a certain amount of exposure to a wide range of occasionally amusing, often distracting behavior from fellow passengers.

There’s the woman on her phone two rows over, busy informing the entire bus about her weekend plans. The man who insists his dog have a seat to itself when it’s standing room only. The guy next to you whose briefcase is poking you in the side the entire trip.

I could go on, but the point is there’s no shortage of opportunity to be annoyed about something if you wanted to be.

In the past I would just try to take these moments in stride, with varying degrees of success. And then this quote happened:

“The useful answers, the answers that help us solve problems, are always the more forgiving ones. They’re based on a line of inquiry that assumes there is always a good reason for everything.”

- Barbara Sher

It wasn’t a sun-bursts-through-the-clouds moment when I first read it. I remember thinking, “Hm, that’s interesting, I should put that in my Evernote.” So I did, and kept reading. But I couldn’t get the idea out of my head, and the more time that passed, the more profound it seemed.

Maybe the woman on her cell phone is in a long distance relationship and her significant other is coming to visit this weekend for the first time in three months. Maybe the dog doesn’t handle crowds well and is much more at ease on a seat than on the ground. Maybe the guy sitting next to you just bought a new briefcase and can’t get over how nice the leather feels in his hands.

It doesn’t matter how implausible any of these explanations sound. By directing your awareness out instead of in, you change a potential source of irritation into an opportunity to exercise creativity and empathy.

The beauty of this philosophy is that it’s applicable in many other contexts as well:

Practicing user-centered design

I was on an email thread the other day where the product team was discussing findings from a usability study. Participants in the lab were overlooking the placement of a new answer on the results page and there was debate as to whether we should break the answer framework to make it more prominent.

One argument against doing so was a principled desire to avoid “designing for failure.” I agree it’s not possible to solve for every corner case, but a blanket stance like this assumes your users are robots instead of humans.

Some might also contend that a forgiving approach is at odds with having a strong product vision. I disagree. Steve Jobs was unyielding in the pursuit of his vision, but the devices and experiences he created were successful precisely because they were so intuitive to use and crafted with deep attention to the needs—and imperfections—of the people who would be interacting with them.

Change is hard. Creators have a responsibility to push the envelope, but you have to allow for the fact that not everyone is going to get it on day one. Roll out gradually and give people the option to go back to the old experience if they’re not ready.

Leading and managing teams

Effective managers have a habit of asking “Why?”

When you invite their feedback on an idea or problem, they first want to understand the assumptions you’re making and the motivations of the parties involved. They usually have an instinct about the right course of action, but rather than jumping to conclusions, they learn how you’ve approached the issue before offering advice.

As a leader, it’s tempting to equate an approach where you assume there’s a good reason for everything with weakness and being a pushover. But in the same way you can show respect even if you don’t agree with someone’s perspective, there’s a difference between acknowledging where a person is coming from and endorsing their point of view.

Whether it’s in the workplace, classroom, home, or even just on the bus, I’ve never regretted taking time to consider the more forgiving explanations behind people’s behavior.

The metaphor test

I was talking the other day with someone who works at LinkedIn about the direction the company wants to take its product and brand. She articulated a few interesting metaphors (paraphrased) to describe the gap between where they are today and where they want to go:

“Right now we’re kind of like an insurance product, something people have as a ‘check the box’ kind of thing and don’t really turn to until they’re looking for a job. We want to be a lot more than just a glance in the rearview mirror of your career. We want to be a place of opportunity, knowledge, and insight; a place to celebrate professional achievements; a place to be inspired by and engage with people who are passionate about the same things you are. In today’s world, you need to think about your career as a lifelong beta test. And we want to be your partner at each step of that journey.”

I’m always fascinated by the language people use to talk about their product and the metaphors they employ, in particular. The latter is often a good barometer of two things: 1) how well a company understands the job that users are hiring its product to do, and 2) the strength of its vision for the future.

To take the example above, it’s evident the team has a keen understanding of how people perceive LinkedIn today. The association with an insurance product isn’t ideal—by definition, insurance is a safeguard against bad outcomes. I‘m guessing most people don’t relish spending time on LinkedIn; their profile is something they feel compelled to keep up.

The analogy to a “glance in the rearview mirror” highlights the reactive mentality many users have towards the product: finished an internship –> update my profile; closed a deal –> update my profile; group just got downsized –> really need to update my profile. By and large, external events are what prompt engagement as opposed to a proactive pull towards the platform. Initiatives like LinkedIn Today and the Influencers program are attempts to start this shift.

I think the company is still figuring out the much harder challenge of what it wants to be going forward. While “a place of opportunity, knowledge, and insight” feels too broad to be actionable, the idea of being a co-experimenter as people continually beta test their careers has legs.

A metaphor brainstorm is a good test of your user empathy and storytelling skills. When you find something that resonates, it’ll be valuable not just in a marketing context, but also as a way to motivate your team and bring them along on the journey towards a longer-term vision.

You can live with less stuff than you think

An inventory of my belongings when I moved from New York to Seattle a year ago yielded one carry-on suitcase, two larger suitcases, and two small boxes. Situational factors played a role, no doubt. When your bedroom is a little over 50 sqft you economize out of necessity. And how much stuff can a single 23 year-old possibly have, anyway.

But I’ve since adopted the “less is more” philosophy as a conscious part of my lifestyle, e.g., for every new item of clothing I buy, I try to donate one, ideally two, equivalent pieces from my closet. I’m not advocating this approach for everyone, but it’s worth laying out some of the obvious (and not so obvious) benefits of owning less stuff:

The obvious:

You never live beyond your means.

You’re more productive. You spend less time, mental bandwidth, and physical energy maintaining, organizing, and replacing things. Time that can go towards more personally meaningful pursuits (like writing!).

Moving is way less stressful. You can feasibly ask friends to help out and be confident no one will hate you for it by the end of the day.

It’s where our (sharing) economy is going. Most of our media is already subscription-based: Netflix instead of DVD collections, Spotify instead of iTune libraries, Oyster instead of one-off ebooks. And services like Airbnb, Lyft, and Artsicle are making it more attractive to rent all kinds of physical goods.

The not so obvious:

You develop a better taste for quality. Everything you do own is usually pretty high quality for a given budget. This discernment translates to other aspects of your life—you learn to hone in on just the essential elements of a product or service.

You flex your creativity muscles. Instead of buying everything you think is cool, you think about what qualities make it so and how you can integrate more of that spirit into the things you create. You give more thoughtful gifts, favoring shared experiences over material things.

You’re more adventurous. You’re more inclined to spend time out and about, meeting people, experiencing new sights, sounds, and emotions.

You’re more adaptable. It takes less time to adjust to other cultures and settle in before you feel at home. The less physical baggage you have, the less cognitive biases you bring to interactions. You realize there are many ways to fulfill the same need.

No matter where you are on the spectrum of “owning stuff,” it doesn’t take much to practice less consumption. Start small—knock off one or two things from your holiday wish list this year and spend time with loved ones instead. You’ll be surprised at how little you miss the things and how much you appreciate the shared moments.

Does your app pass the "Is it painfully obvious what I'm supposed to do next" test?

Two new apps have wrangled coveted page one real estate on my iPhone. Both pass the test in the title of this post with flying colors. The benchmark scenario? Whether I can hand the phone to my mom and she can start using the app without explanation.

If you compare successful mobile-first communication apps like Instagram, Snapchat, or Vine, to web-first products like Facebook, Quora, or even Twitter, two things stand out. The apps in the first group do one thing and they do it very well. In addition to laser-like focus, these apps adopt a stripped-down, linear experience.

Tinder and Frontback share these same qualities. Right from launch, the one-way flow guides you from screen to screen with a limited number of options at each step. The mental effort required to engage is minimal. It isn’t a prerequisite for success, but I think this constrained approach will be a hallmark of more mobile apps going forward.


The first time you launch Tinder, you see a person’s face with two buttons below it: a green check and a red x. Not exactly subtle. After you make your first yay or nay decision, a notification shows you how to swipe left to pass on someone and swipe right to show them some love. At this point, even if you’re the kind of person who winces at the idea of making superficial, split-second judgments, I can almost guarantee you’ll be busy swiping for the next ten minutes.

When there’s a match, a full-screen notification asks if you want to chat or keep playing. If you decide to try and strike up a conversation, the app practically goads you into doing so with copy like “You’re too afraid to say hi? Wuss,” and “In many cultures silence is considered rude.”

The result, in my case, was pretty successful—four dates within two weeks of downloading the app. Contrast this with my experience on OkCupid, where I invested much more time in creating a profile (since disabled), waded through messages that were 90% spam, and didn’t go on a single date. I only wish there was an intermediary step between messaging on Tinder and an in-person meeting where you’re committed for at least an hour. A quick video chat, maybe?


The name says it all: take a picture of what’s in front of you, direct the camera back on yourself, and then stitch the images together, one on top of the other.

Opening the app immediately launches the rear-facing camera (perhaps taking a page from Snapchat’s playbook). The bottom half of the screen is obscured to keep your focus on capturing the moment in front of you.

After you snap the first image, the lower half of the screen activates and engages the front-facing camera. A second tap and you’re ready to share.