1. Quick Tips for Effective Customer Interviews

    I work with many entrepreneurs who often mistake the concept of “talk to customers” as a sales pitch or an online survey. They go into salesman mode, pitch hard without hearing what the customer has to say, and ask leading questions that steer the customer into responding in ways that reaffirm his beliefs.

    The goal of customer interviews is to collect detailed stories on customer mentality, behavior, and frustrations. Ideally, this is done in person, or over Skype, so you can dig deeper into the answers they provide. This builds empathy, uncovers richer insights, and reveals opportunities you could solve for that you may not have considered before. 

    Here are some quick tips to help you get the most out of customer interviews.

    Interview Preparation:

    1. Effective exploration starts with having a clear customer in mind.

    2. Get rid of any preconceived notions you have about your solution; focusing too early on testing the solution makes you prone to biases that will prevent you from hearing what customers have to say.

    3. Jot down a list of questions that test your riskiest assumption. It’s not necessary to write out the questions one by one. The best approach I’ve found is keeping in mind key objectives you’re looking to get insight on, and having a casual conversation with your subject around those objectives.

    Interview Techniques:


    1. Never start off by saying that you’re working on an idea. This biases the interviewee and they will feel inclined to be nice or reverse engineer your questions.

    2. Never ask leading questions. You are priming the interviewee for the answer you want to hear.

      Bad: It’s really awful to wait in long lines, isn’t it?

      Good: Tell me about the last time you waited in a long line.

    1. Never put the interviewee in hypothetical scenarios. The more you ask them to imagine a situation, the less you can trust their answers.

      Bad: If you were stopped by the police, what would you do?  

      Good: Have you ever been stopped by the police? What did you do?

    2. Never start a question with “would.” This asks them about future behavior, which they cannot predict and is not reliable.

      Bad: Would you pay for this?

      Good: Actually test if they will through a Pitch experiment. 

    3. Never start a question with “do,” unless it’s a qualifying question.

      Bad: Do you want more free time?

      Good: How do you manage your time?

      Qualifying question: Do you have kids?


    1. Qualify the person you’re talking to and make sure he/she fits your customer hypothesis.

    2. Always ask about past behavior.

    3. Always start questions with “who, what, why, when, where, how.” Why and how questions surface the most insightful answers.

    4. Always close by asking for their contact information and an intro to others who fit the customer profile. Chances are they have friends or colleagues who do.

    5. Always make sure your interviewee is not your mom, dad, or friend.

  2. When should your startup focus on UX?

    When do you optimize your User Experience and when does it take a lower priority? Contrary to popular belief, User Experience will not solve all your product problems. The key is to understand the context under which your product operates. 

    Part 1. What kind of startup are you?

    There are 4 kinds of startups I have identified. Vitamins, Painkillers, Addictive Drugs, and Extinct (I don’t have a name for this 4th one, but it might as well be extinct).

    You can easily identify which category you’re in by understanding the depth and frequency of the problem you’re trying to solve.

    Which quadrant do you fall in?


    Most startups fall in the vitamin quadrant. This means, you are solving a problem that is not very painful, but frequently encountered. Since there are many players in this space, you need to strategically enhance the experience of your product in order to compete in the crowded marketplace. Sometimes you’ll find that in this saturated environment, most customers are already content and occupied with the existing options in the market. In this case, even a great UX may not be enough.

    Addictive drug. This is where you want to be. They cannot get enough of you. Most users have this problem so badly and frequently that they are finding workarounds to solve it themselves. Their current workarounds are so broken, cumbersome, long, tedious, and inefficient that your product will streamline their experience and they will be forever grateful. They exclaim, “How did I live without this thing?!” because they’re so elated with any solution that is better than their workaround. They will be highly active on your product even if it doesn’t have a great initial UX. If you trip up, they will be frustrated, but forgiving. Although, be strategic about your UX moving forward, as other competitors creep in.

    Painkillers. High pain, low frequency. Many entrepreneurs have ideas that fall in this space. It usually happens when they’re in the midst of tossing around various startup ideas, and suddenly encounter a huge, frustrating problem. For example, their car gets towed while they were at some tech Meetup about mobile apps. “Argh! Why is there not a fix for this??” they ask. So, they decide to jump in and solve it with an app. Does UX matter here? It depends - are you here to build a sustainable business? Or are you happy building a one-time use solution? If you’re looking to build a scalable business, you don’t want to be here either. If the latter, sure, save users the torture by making it dead simple to use, but, it won’t get much use.

    Extinct. So…what problem are you trying to solve?

    This is Part 1. My next article will walk through examples of how you can design UX tailored for these different contexts. Sign up to stay tuned.

  3. What’s it like at an all female entrepreneurs’ conference?

    Yesterday was the third annual Women Entrepreneurs Festival from ITPHaving attended many male dominated entrepreneurship events, I noticed many interesting differences in the unfolding atmosphere of this conference. Most notably the format of the conference and the traits of the entrepreneurs I met.

    The usual business networking event is structured in a way that is reminiscent of a hunt for game. Each entrepreneur fends for themselves as they zigzag their way through the crowd, armed with business cards and conversation starters. Aggressive is the rule in play. No time to hesitate. 

    At WeFestival, the organizers, Midori, Joanne and Nancy, were very thoughtful and attentive in catering to their particular audience, creating a comfortable, inviting environment for new entrepreneurs timidly looking to step out.  

    The centerpiece of the event was clustered seating arrangements with other females you’d have things in common with and a thought-provoking prompt to get the conversation started. I was surprised by how open and honest everyone was. These entrepreneurs were willing to admit and share their challenges, and the community encouraged it.

    A side note: My takeaway from this interaction was conferences organized by women who understand how to create the right atmosphere will attract more women, not necessarily more women on speaking panels.

    Then came the pitches. The ideas came from different verticals like skin care, civic engagement, social good, wedding, food, healthcare and media. There was no flaunting of shiny new apps, or flaunting the latest technology. Their businesses were less tied to technology as a platform, but rather used the websites to reach a wider audience. It’s fine, because not all problems must be solved with a website or mobile app. 

    I was impressed by how customer focused they all were. Each of them were operating close to the ground, getting constant customer feedback. They knew their customers well and told their stories. Each demonstrated a transparent thought process and were refreshingly honest in their pitch, even admitting flaws, challenges, and things they needed to look out for.

    These were raw founders who didn’t go through accelerators or have perfect pitches, but were building revenue generating businesses from the ground up because there was demand for their services and they were answering and solving that real human need. Technology was almost an after thought in some cases. Each idea was realistic and practical, even bootstrapped.

    There were no lofty claims of taking over the world with an app, rather, a quiet knowing that their work has already changed their customer’s lives and impacted the world.

    As the conference drew to a close, with the last speaker finishing up her final sentence, Charlie shot straight for the VC judges, while the women patiently waited for the full close. “That’s how men do it,” my friend, Farrah, remarked.


  4. The ugly flaw of design at startups

    There is a huge misconception of design at startups. Design is not the deciding factor for a successful startup. It is easy to look at successful companies like Twitter and Apple and rationalize that their beauty and brand led to success. You are just looking at an end result. You cannot emulate an end result.  

    If you are optimizing for brand and user experience at your startup, take a step back, understand what kind of startup you are and test whether you are creating customer value first. The existing design mentality of emotional optimization is an artifact of working with established companies with proven models. 

    In established companies, the problem is given.  

    They refine their brand and UX to create the emotional connection needed to differentiate from competitors offering similar value. It is a marketing strategy to optimize because they have proven their business model and value to customers. 

    In a startup, the problem must be challenged and explored.

    If you have a great brand and UX, customers will want to love you. But when they realize you don’t solve their needs and don’t fit into their lifestyle, you drop off and gather dust like the pretty souvenir they bought abroad.

    Design at a startup is not just about optimizing brand or user experience. Design is an encompassing mentality of questioning the given, uncovering true problems, and making informed decisions. The fundamental aspect of design at a startup is to realize and validate the true function of your startup. Then, form follows function.

    Thanks to David Cole, Seth Godin, and Alex Payne for helping me crystallize these thoughts.

    Stay updated on my next post, where I delve deeper into this topic.

  5. 7 Huge Mistakes to Avoid as a Lean Startup

    Lean Startup Machine requires you to abandon all ego going in. Remember to leave all ego behind going out. 

    There are so many nuances to the Lean Startup methodology that it’s easy to think you’re doing it, but you’re not.

    Many make the mistake, thinking “Of course I talk to people before I build. That makes total sense. I’m lean.” Although, the concept is easy to understand, it requires self-awareness and an objective mind to effectively maintain it in practice. I especially emphasize the importance of properly structuring interview questions to get reliable data, and avoiding the traps of confirmation bias. I emphasize these as the foundational structure to starting out lean because this is where I tripped up myself.

    2 years ago…

    I was another young entrepreneur, fresh out of college, trying to get my startup idea off the ground. As a first step, I decided to attend a 3-day workshop on Lean Startup methodologies. At the time, I had no idea what Lean Startup was, it was just recommended as a good starting point for entrepreneurs. What I took away from that first Lean Startup Machine experience was get out, talk to customers early on and test your riskiest assumption. So that was the only education I took into running my own startup. Sounded easy enough.

    My vision was to create a more semantic web. The initial problem I saw was in hiring the right people for personality fit. I started off with a people search engine product for friends to tag each other with skills and characteristics, similar to skills.to and the now defunct, Honestly. After building out the MVP, in which we only had the main functionality of tagging friends working, I went out and talked to people. I learned that the motivation wasn’t enough for people to continuously go into an app to tag their friends. So I killed that idea and focused on something else that would give more semantic meaning to search results. 


    • Didn’t talk to customers early enough
    • Wireframed and designed the product before talking to customers
    • Spent more time talking to investors instead of talking to customers

    Time wasted: 

    2 months implementing until the pivot in mid November


    • Didn’t raise $1M to fail. 
    • Shaved a few months off by learning from customers early enough.

    Pivot to semantic image search. 


    Textual search is limiting, how do you learn more about the world if you have a visual query you cannot put into words? 


    Photo Q&A app that would become a crowd-sourced alternative to Google Goggles. 

    We built out a website MVP in a few hours, with the one functionality of uploading an image and asking a question. The riskiest assumption we wanted to test was, do people even have visual questions to post? 

    In my first try, I found 1 person who enthusiastically responded, 

    "Oh my god, yes! I actually snapped a photo of some kind of bird when I was in Florida. I’ve been wanting to find out what it was, it’d be awesome!" 


    This guy actually had a photo sitting on his phone that he wanted to learn more about! The learning was, we had to go mobile first.

    The second riskiest assumption was, will there be people who are able to answer the photo questions that are posted?

    I sent the photo out and, immediately, someone signed up to answer the question,

    "It’s a Muscovy duck, it’s very common in Florida." 

    Validation, yet again! 

    I tested a few more photo questions through emerging photo platforms, Pinterest and Opinionaided. 2/3 of the questions were successfully answered. It was sufficient validation for us to move full steam ahead, so we went back into the building and hacked away.


    • Fell victim to confirmation bias.
    • Believed insignificant data.
    • Didn’t set a minimum success criteria. If I had determined this, finding one yes out of the few interviewed would not have made it a worthy pursuit.
    • Forgot to talk to customers continuously.
    • Got caught up in features. 

    3 months in… 

    My cofounder and I had a falling out and parted ways. But he was convinced it was a million dollar idea and went back into his room to work on it for another 6 months before he finally launched it in the Apple App store. Everyone flocked to it and it blew up overnight! No one showed up. No one cared. No ratings. No reviews. Nothing.

    Convinced it was a problem in design and marketing, I started up again with another team. Same idea, but more beautifully designed!

    This time, being more familiar with Lean Startup and being more self-aware doing a startup a second time, I started hearing the feedback I had previously tuned out. 

    "Um…what would I use this for?" The hesitant response came up over and over again. 

    One guy, after thinking a bit realized, ”Oh…yea… I took a picture of a poster the other day and was wondering what it meant…”

    Another girl perked up, “Oh cool! So I can take a picture of myself to ask about an outfit I’m wearing?”

    "Well, yes…you could…" But that’s not what this is for…

    I started to see. The problem didn’t seem to exist for people. If it did, it wasn’t painful enough for them to actively be seeking a solution. People weren’t pulling at me demanding to use it. My vision was for the app to be filled with thought-provoking content, a visual way to learn about and tag the world.

    Reality was, there was no problem.

    The three problems that did surface consistently were bird watching, skin conditions (another team validated this idea and won LSM a few months later), and fashion. None of which I was interested in focusing in on. I killed the idea and joined Lean Startup Machine. Since joining, we’ve fleshed out our curriculum to enhance the learning process and train entrepreneurs in the nuances of Lean Startup methodologies through real-world application. 

    It’s hard to change the way you think.

    It’s taken me complete immersion in Lean Startup Machine, failed startups, wariness of subjective bias, and emotional detachment from my own startup ideas to actually look at ideas objectively and see what won’t work.

    Biggest mistakes YOU need to avoid:

    Mistake 1:

    Cofounder didn’t attend Lean Startup Machine, resulting in some lack of understanding. If you have a cofounder or startup team, you should all attend Lean Startup Machine together.

    Mistake 2: 

    MVP doesn’t need to be built. Now we’ve broken down MVP into 3 stages to really emphasize MVP is any experiment you run that will increase your learnings about your customer.

    Mistake 3:

    Stop selling on vision! Start listening.

    Mistake 4:

    Don’t ask leading questions. The way you phrase your questions determine the level of reliability in the answers you get. 

    Mistake 5:

    Don’t think or pitch on features of the future.

    Mistake 6:

    Beautiful design will not cure an ugly baby. (Product that no one wants)

    Mistake 7:

    Don’t fall in love with your solution and romanticize it in your head.


    I shaved time and $$ off of being unproductive building something no one wants.

    Based on my insights from talking to customers, I realized early on that, without a significant problem or passion unifying users, there is lack of structure. This leads to poor quality content being generated. Interestingly enough, that behavior is being manifested on another photo Q&A app.

    Can you think of more mistakes?
  6. Starting up Female

    There is a giant push for more female entrepreneurs right now led up by empowering initiatives and resources like Change the Ratio, Women 2.0, WITI, and The Daily Muse.

    With so much support and encouragement from the growing women in tech community, now is definitely a great time to take your step and run after your dreams.

    But as a female entrepreneur myself, I would like to take this time to share some of my experiences and missteps as a female starting up in tech, so other females can look out for and avoid similar situations.

    Before we begin: This is a very personal story that has been hard for me to share. I was finally prompted to write about my experience thanks to a few other women sharing their voices through recent articles. In particular, the recent post and advice from Rachel and Cindy.

    The search for a cofounder isn’t that different from the search for a soulmate. You’ve heard it many times before - picking a cofounder is like picking a husband or wife. It is. You are looking for someone who gets you, your way of thinking, why you’re creating the product, and where you want it to be. You are looking for someone to be completely in sync with.

    This creates a rather challenging situation for female entrepreneurs seeking a technical cofounder, most of who are male.

    What I’m about to share is probably a very unusual startup horror story:

    I left my first job shortly out of college to work on my startup. I was working with a guy I knew of from high school. We met up for coffee when he learned I was into startups and working on a side project. We had a great conversation, really hit it off and he offered to help me on the technical side of my project. He was an iOS developer and I was a mobile UX designer. We thought on the same wavelength, were able to bounce ideas off each other, and enjoyed hanging out together. We were a solid, well-balanced team. Or so it seemed.

    The seed of the problem started when he admitted he liked me. I told him I wasn’t interested in a relationship and he let it go. I thought that was that. We had met up and were working together to start a business, so we kept working together. He soon quit his job to join me full-time and we started working out of his apartment. I ran around meeting people, researched, wireframed, designed, and he implemented the functionality. A few months in, we were looking to take our startup to the next level. But that wasn’t the only thing that wanted to get to the next level; in the midst of investor meetings, he sat me down and told me he was in love with me. This would’ve been great news had I felt the same, but I maintained I was not interested. After that, things turned sour. His demeanor completely changed. He became bitter and uncooperative, and we started arguing over the smallest things that didn’t even matter. His agreeableness and willingness to hear my point of view on the product was gone. We could no longer work together.

    But, he still gave me one last chance to keep our startup alive. His ultimatum:
    "I can make anything happen for you. If, you were to be with me."
    I was thrown into a state of shock, disgusted and insulted by how he was trying to take advantage of the situation. I refused.

    That was one crushing experience to go through. But the second one was on its way…

    After we agreed to shut down, he decided he liked the product so much, he was going to run off and launch it himself (entrepreneur’s worst nightmare right?). I’ll be writing a post later on what happened here and why, in the end, you shouldn’t worry too much if this happens.

    I spent a long time afterwards reflecting and trying to figure out what happened. What went wrong? What could I have done to prevent it? Did this happen to anyone else? Was it common, but just unspoken of?

    Here are some of my lessons learned.

    Don’t be desperate. This is something first time entrepreneurs are very vulnerable to. Many jump at the chance when they believe they’ve finally found that person who gets them and thinks on their wavelength. It’s natural but could be dangerous; and it’s easy to overlook those slight uneasy feelings when you have this great idea you just want to execute on.

    Understand motivation. It’s not enough that you guys think alike and get along. It’s important to understand their motivation. Motivation drives behavior. No matter what they say or how they behave, if someone didn’t enter a business relationship with the right intent, when push comes to shove, their true colors will show.

    Speak up. Be assertive and firm on where you stand in the situation. I have always been hesitant to speak up, be assertive or confrontational, but people will take advantage of this. Lay down the law so there is no room for second guessing. Make it known how you feel so that it is black and white. Don’t worry or be hesitant that you are coming off as harsh or arrogant. I still need to work on this.

    Don’t give up. This is most important! Don’t be daunted! Get back on your feet. After it fell through, I spent a week or two reflecting and learning from the situation, got back into a full-time job, and worked to revive my startup with a different team on the side.

    This quote from Cindy Gallop’s WITI interview really sums it up best:

    "female entrepreneurs face many more obstacles than men, the playing field is not level… know that, just grit your teeth and make your startup happen"…"only person to make things happen for you is you"

    For male-female partnerships, it’s possible to confuse romantic interest for professional compatibility or make professional decisions that are subconsciously driven by a romantic interest, whether intentional or not. There has been one other situation I’ve heard about in which the cofounder also developed an interest in the female cofounder and had to part ways. So, although not too common, it still does happen and it’s important to be wary of such a situation arising. Avoid this by making sure you two are on the same page and laying down the rules ahead of time. Any other tips on how to avoid or talk about these situations?

    It’s embarrassing to explain that such an unprofessional thing killed our startup. But the lessons learned through this experience definitely extends across areas, like figuring out if someone will actually be a good cofounder, that is applicable for both male and female entrepreneurs.

    Here is the full list of articles and relevant discussions that prompted me to finally write about this:

    NYTimes: For Women, Parity Is Still a Subtly Steep Climb

    WITI Summit: Cindy Gallop on NYC startup scene and funding for women

    HBR: Four ways women stunt their careers

    Change the Ratio: Women, apply to YC!

    TED: Sheryl Sandberg on Why we have too few women leaders

    On Startups: Choosing a cofounder

    Mark Suster: Why aren’t there more women entrepreneurs


    Thanks everyone.