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…”

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!

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.

Why you should embrace vulnerability

Stay optimistic. Life can wear you down. Every disappointment followed by lowered expectations. A defense mechanism to curb the pain of future disappointment. It’s a horrible way to live, hoping for less each time. Have the courage to always shoot higher.

– A Letter to My Godson, Hsu Ken Ooi

I like to think I would have made it if it wasn’t for the flies. Attempting “Haystack” scramble at the summit of Mount Si was hard enough with both hands at my disposal, let alone just one because the other was too busy swatting flies.

Whatever my excuse, I didn’t make it to the top, turning around about a third of the way up. Consoling my pride on the retreat, I reasoned there were plenty of fears to conquer that didn’t involve a potentially fatal impact with rock from hundreds of feet up in the air.

One thing that’s never left me about that experience was how completely exposed I felt clinging to the rock face, so physically vulnerable.

This is a post about another kind of vulnerability. About extending your hand with no idea if the other person will take it. About throwing yourself into a creative challenge and offering up your effort to the world for critique. About telling someone the story of the time you messed it all up.

Quick quiz:

  1. How often are you the first to say “I’m sorry”?
  2. When was the last time you asked someone to explain something you didn’t understand?
  3. How likely are you to be the first to say “I love you”?
  4. When was the last time you acknowledged to someone you made a mistake?
  5. When was the last time you asked for feedback on something meaningful to you?

Why do the answers to any of these questions matter?

Most of us go through our daily lives inhabiting a narrow band of emotion, teeter-tottering between bored and anxious on the low end, and content and comfortable on the high end. It’s a safe but uninspired way to live.

Why do we settle for a monotone palette when we all want to experience more moments of bright color — emotions like joy, connection, and gratitude?

Instinctively, we realize that pursuing intense happiness also exposes us to intense fear, disappointment, and pain.

“Instinct” is a funny word to use in this context. Humans are wired to seek understanding, confirmation that others share our hopes and struggles. As kids, our instinct is to operate from this place of openness. We go into each interaction and lay it all on the line, with no sense of holding back. It’s not until our first taste of rejection that our instinct becomes one of caution and withdrawal.

The degree to which we’re able to laugh, celebrate, and love is directly related to our willingness to take the uncomfortable stuff hand-in-hand. And many of us simply don’t have a very high vulnerability tolerance. In an attempt to dull the impact of loss and rejection, we also end up closing doors to life’s happiest possibilities.

As an example, many of us have probably experienced a situation where we downplay how much we want something to minimize embarrassment in case things don’t work out. The reality is that this doesn’t ease the pain of failure, it only prevents others from sharing in our happiness when we succeed.

One of the most empowering realizations is that it’s possible to build up your tolerance over time, even learn to embrace vulnerability.

Ground rule #1 (and really the only rule), is that you need to come to terms with your own strengths and weaknesses. Nothing is gained from putting yourself out there if it’s not the real you, imperfections and all. You can’t hope to find acceptance and generosity from others if you don’t have it for yourself.

I’m often reminded of this quote by Barbara Sher: “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.”

The next step is just to go out there and practice a little bit of vulnerability every day.

You can start with something as simple as meeting every stranger’s glance with a smile and a steady gaze. Many will look away. Some will look confused. A few might even smirk, or frown. No matter. The ones who smile in return make the exercise worth it many times over.

As with all things in life worth pursuing, you get back as much as you put in. Don’t let the possibility of rejection keep you from extending your hand.

Have the courage to always shoot higher.

Life lessons from learning Lindy Hop

1. There’s no substitute for getting out on the dance floor.

Taking classes but never going social dancing is like learning how to scuba dive in a pool and then deciding, “Yea, I think I’ll stop here. This is practically the same thing as diving in the ocean, right?” You miss out on the best part of the experience.

Confidence comes after action, not before. You’re never going to feel 100% ready, so if that’s what you’re waiting for, I hope you’re blessed with Yoda-like patience and plan to live forever. Turns out the fastest way to become a better dancer is to just go dancing.

2. Self-awareness and humility go a long way.

It’s funny how some partners’ first instinct when a move doesn’t go as planned is to point out what the other person did wrong. Other partners will proactively ask for feedback on what they could have done better, regardless of who was technically at fault. Guesses as to which approach makes more friends?

3. Don’t overthink it.

When I first started social dancing, I worried about getting my footwork exactly right. The result was a negative feedback loop where I was so caught up in not making a mistake that, naturally, I noticed every little mistake, which led to less confidence, more nervousness, and more mistakes. Not to mention it’s impossible to establish a connection with your partner when your eyes are glued down at your feet.

It took me an embarrassingly long while to realize that it’s more important to just go with the music and fake it than to get the steps exactly right. Trust that your feet will know what to do even if your brain can’t keep up. You’ll look like you’re having more fun because you will be having more fun.

Why you should never miss an opportunity to demo your product

Even in the tent’s shade my t-shirt keeps sticking to me. It’s way past lunch time and hunger gnaws at my stomach; we’re approaching hour four of being up on our feet. My voice has turned into a sexy rasp thanks to non-stop talking. I steal a quick sip of water before it’s time to face the next group. Their impatience is palpable. Many are eyeing the swag table, no doubt wondering how long they have to listen to me before they can grab their free stuff.

Physical conditions aside, this was not an ideal situation for a classic introvert, yours truly. But demoing at our product fair this week made me realize just how powerful a tool it can be—demos are a rare opportunity to gather instantaneous feedback on both your salesmanship and your product. It’s hard to think of another form of communication that delivers a broad range of feedback so quickly.

You can spend weeks preparing for a presentation but unless you moonlight as an improv performer, there’s not much you can do to change course in the moment if your message isn’t resonating. It’s also hard to gauge exactly how things went, except maybe looking at the number of people who ask questions or approach you afterward.

Or take a blog post—you invest a couple of hours writing, maybe have a few trusted eyes look it over, and then cross publish on any number of platforms. Sometimes the views, comments, and retweets pour in (or so I’ve heard), sometimes they trickle, and other times it’s crickets. Even successful bloggers struggle to predict what will be a hit vs. a miss, which is why many have started experimenting with lightweight methods of testing potential topics before committing to a post.

Contrast this with a live demo, where you’re often inches away from the audience and can adjust your pitch based on a multitude of factors: people’s facial expressions, their familiarity with your product, the questions they ask.

Usability studies probably come the closest to mimicking the real-time feedback of a demo. But it’s usually easier for people to give honest and/or critical opinions when they’re being sold something as opposed to being studied in a research environment (see Hawthorne effect).

Demos just might be the gold standard for tight feedback loops. Below are a couple of lessons learned from my day on the front lines.

Engage your audience as early as possible.

An easy way to do this is to start with a question, e.g., “How familiar are you with XYZ product?” or “Have you guys tried XYZ before?” Getting people to respond to a simple question in the beginning increases the likelihood they’ll participate throughout and ask questions.

Welcome positive and negative feedback.

Audience members at live demos tend to come in two flavors: sympathizers and skeptics. Note the features and messaging that resonate with the former; those are worth emphasizing in your marketing. Objections and concerns raised by the latter are things to keep in mind for future releases. Invite constructive criticism by explaining that the product is evolving and the team is always looking for ways to improve. See if there are any trends in both the positive and negative feedback you receive.

Attention, identity, and Google Glass

In a 2011 post on mobile identity, Rebekah Cox wrote, “In its most basic form, your identity is the product of how you manage your attention and others’ access to that attention. Those areas where your attention is focused assemble to form a set of experiences that shape and influence where you’ll direct future attention.”

Prior to reading this post for the first time a couple of weeks ago, I had never thought to define identity in this way. In fact, the things I typically associated with identity—an email address, password, Facebook profile—were precisely those things Rebekah called out as not identity in the preceding paragraph.

But once this new perspective planted itself in my head, I started to spot other expressions of the same idea. There’s this quote from a post by Etan Zapinsky on Snapchat’s recent iOS update: “More than anything else, the people we communicate with define who were are. A timeless phrase sums it up beautifully, “Tell me who your friends are and I’ll tell you who you are.”

And this observation from a Times adaptation of the commencement address Jonathan Safran Foer gave at Middlebury: “My daily use of technological communication has been shaping me into someone more likely to forget others. The flow of water carves rock, a little bit at a time. And our personhood is carved, too, by the flow of our habits.”

And finally, this excerpt from Mihaly Csikszentmihalyil’s Flow: “Each person allocates his or her limited attention either by focusing it intentionally like a beam of energy or by diffusing it in desultory, random movements. The shape and content of life depend on how attention has been used. Entirely different realities will emerge depending on how it is invested.”

If the things we pay attention to determine our experiences, our beliefs, and ultimately, our identities, it follows that the devices mediating so much of our communication with others, our consumption of information, our management of daily to-dos—in short, where and how we direct our attention—would end up shaping who we are.

Consider the way we talk about our smartphones: “extension of myself,” “intimate connection,” “a second brain.” They’re often the first thing we reach for when we open our eyes in the morning and the last thing we put down when we go to sleep at night. For some, the thought of being away from our phones for an extended period of time is enough to induce an anxiety attack. A glimpse of a stranger’s home screen would probably tell you more about them than you’d learn sharing a meal.

In this context, it becomes easier to understand the visceral opposition Facebook Home encountered when it attempted to not so much “wrap” as smother users’ phones. Facebook is a pervasive part of many people’s daily routines. But it’s not the only aspect of our identities, or the most accurate one (as much as it would like to be). The tidy and edited lives we lead on Facebook remind me of Ingrid Bergman’s request that cameras focus on the “good side” of her profile.

One of the promises of Google Glass and its successors is technology that gets out of the way and helps us experience more of the here and now. v1 falls short, but it raises an interesting question: What kind of habits do we want to encourage in our future selves and how can devices like Glass nurture those habits? Is it reasonable to expect that they would nudge us to be more mindful, more present? To focus attention on productive pursuits and avoid distraction? To develop empathy and compassion for others? There are no easy answers, but the alternative is to wake up one day and realize we’ve become strangers to ourselves.