Week 1: Wheels Up


I can’t believe it’s only been 1 week since I started classes here. Over the last 5 days, I have felt like I am drinking from a firehose while simultaneously making 90 new best friends. I spent some time reflecting with friends this week, one of whom made me promise that I wouldn’t “keep it vague.” So here it is, week 1 insights in a nutshell.

Part of the reason I want to be sure to keep sharing insights about my experience here is because I benefitted greatly from the blogs of people who have done this before me (h/t @ellenchisa) when I was deciding whether or not to go to business school.

The start of anything can shake you to your core, and this experience puts you in a blender and burns the candle at both ends. It’s great, but profoundly exhausting. We’re just getting started.

With no basis for comparison, Harvard feels like I am running a marathon at a sprint’s pace. The week started with Section reveal at 7am Monday morning – when you find out who you’ll be spending the whole year learning, debating and making friends with. It’s also the crew you do reunions with and probably the better half of your business partners/friends/colleagues for the rest of your life. I have a great, lively, brilliant group of section mates who make the day go by in a breeze. Go Section F!

HBS teaches by using the case method: practical stories with demonstrable applications of business principles, and nuanced lessons that can be debated in every possible way. We spent 2 days learning about the case method by doing none other than 2 cases. The days were peppered with social activities, alumni panels and an opportunity to meet 2nd year students (ECs) who answered questions.

The crux of the week came at the end, when we had our first 2 days of classes each of which had 3 cases. The courses we are required to take in the first semester spread from Finance (FIN1) and Accounting (FRC) to Leadership (LEAD), Technology and Operations (TOM) and Marketing (MKT).

My initial observations about business school are the following:

  1. There’s no such thing as isolating one business problem: every case could be examined from each of these 5 lenses, and you would unearth something that sways you in a different direction each time.
  2. Practical learning is much more enjoyable than textbook learning: I’ve never taken accounting, but it’s a lot more enjoyable to contextualize a problem than to create sample balance sheets.
  3. Everyone is social all the time: I am giddy every day by the idea of getting to know such a brilliant cohort of people. Taking time to really get to learn about them seems overwhelming at the start – there are a lot of people I want to know and many group events that connect us. People are warm, friendly and gregarious in a way I’ve never seen in a professional environment. I am looking forward to being in a routine that allows me to do this in a more in-depth way.
  4. Listen: this has always been a weakness for me. I started by always having my hand raised in class, but I’m learning that it’s much more valuable to listen to the conversation around you and to interject only when you have something truly meaningful to say. People in the room are much smarter than I am, and often bring to light ideas that had never crossed my mind. Be discerning about hand raising – and only speak once per class.
  5. Collaboration is highly encouraged: unlike in grade school where it was important to do your own work, we excel when we work together. Discussion groups are a valuable forum for this – leverage the experience of your peers and let them do the same with you. The reason to take several years in between college and business school is to be able to give genuine perspective from personal experience on certain topics.
  6. Figure out what you want to be known for, and move fast: Everything moves very quickly here. People are constantly posting ideas, gatherings, questions, etc on social media. In observing this, it’s helping me figure out what kind of role I can play and how I can add value to the group.
  7. Introspection is critical to growth: Harvard asked us to submit personal portraits about what we’d like to get out of these 2 years. The application process is a way to step back and reflect, and the act of taking yourself out of the work force most likely forced us all to think about these things before we acted. Nonetheless, this task was extremely challenging but very rewarding: I now have a stronger sense of what motivates me, what my values are and how to think about being introspective and reevaluate during this time.
  8. Bring your own lunch: the Spangler cafeteria is insane from 12:10 to 1:25.
  9. Be punctual – not to be taken lightly: This is seriously critical and indicative of better business behavior. On the contrary, the business formal thing isn’t really all that.
  10. Business school is genuinely fun: it’s a time to step back and reflect, and also to enjoy meeting new people and reconnect with old friends. Smile!
Week 1: Wheels Up

10 Lessons I Learned While Working At Twitter

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I have been fortunate to have worked for this great company for the last 3.5 years, and even more lucky to work alongside some of the best and brightest minds in the industry. Yesterday, I culminated my Twitter experience by delivering something called The Last Lecture, an oratory style based off of Randy Pausch’s own last lecture at Carnegie Mellon.

The topic was on the 10 lessons I learned from working at Twitter. Looking at this list, I believe that I’ve had the best job at the best company. I don’t take for granted the fact that I’ve been able to learn all of these valuable lessons in such a short amount of time, and that I’ve been surrounded by great people who have taught me these wonderful things.

  1. You don’t get what you don’t ask for. Some of the greatest ideas start with a question, and you don’t get 100% of the things you don’t ask for. I challenge myself to ask a question at every possible avenue.
  2. Challenge assumptions, even though you respect those who made them. The beauty of working at a small and rapidly growing company is that there doesn’t exist precedent for a lot of the things we’re doing. As a result, I found myself constantly challenging the status quo: why are we structured this way? Why doesn’t this exist, or how can we be more efficient? Nothing is set in stone, and we have to thrive on malleability.
  3. Be an entrepreneur within a growing organization. I had the fortune of working on a project early in my time at the company. It was suited to my skills and my background, and conveniently something that the company desperately needed. I had the best manager support and was able to write my own job description to help found a new team – the opportunity of a lifetime.
  4. Own something: become an expert and do it well. Being the “go-to” person for an industry, a workstream or even a market can put you on the map for projects you may never have otherwise had. I have been privy to many interesting things happening across the company because of my historical understanding of certain things, and it’s opened my eyes to many new schools of thought.
  5. Meet as many people as possible. Twitter is made of people, and those people have exceptionally interesting stories and backgrounds. One of the beautiful things about working in tech is that you have a variety of people with many different backgrounds, and we all have so much to learn from each of them. I made a point of trying to grab coffee with 2 new people every week, and I have started to forge lifelong friendships and business contacts with many of these brilliant people.
  6. The only thing you can count on is change. You only have to read the newspaper once in the last 6 weeks to know that Twitter is a company that undergoes constant change. But we are also the kind of company that thrives on it. We strive to be the best, the boldest, and do good for the world. That’s not possible without embracing change in all forms – trying new things in new ways allows us to achieve greatness.
  7. Work with the goal of leaving Twitter [or any company] a better place than you found it. This principle guides me in everything I do. My hope is to change people’s lives and leave a legacy that will help people move and grow. I feel humbled that I was able to work on the Super Women at Twitter initiative to help the industry start to think about how to strive for gender and diversity fairness.
  8. Use the product. There are times when we all take things for granted. But working for a company with a product as powerful as Twitter’s makes me step back all the time and realize that we are working on something great. I find myself with my breath taken away almost every time I open the app. The fearless communication that takes place, the revolutions, the idea generation and even the humor are awe-inspiring.
  9. Surround yourself with bright spots. When I started, my organization had 5 tenacious people. Today, we have over 120. I had a hand in helping grow our talent pool and our scope, and one of the most important things I learned in the process was to be sure that I worked, hired and managed people I could learn from and people who inspired me. We’ve built an exceptional team of people, and we’re hiring!
  10. Life can’t be contained in 140 characters, but you can do a lot with constraint. This company is built on 10 core values, all of which can be contained within a tweet. They are our integrity, our guiding light and our savior in times of confusion. These are beautiful pearls of wisdom that have helped us achieve greatness, and will continue to shepherd us through. The power of a Tweet is endless.


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10 Lessons I Learned While Working At Twitter

Next Steps


I’m excited to announce that I’ll be embarking on my next big adventure in the fall: Harvard Business School. I feel lucky to have such supportive friends and family, and I have a few more important life milestones to achieve before I head to Cambridge in September.

To say that the last 3 years at Twitter have been transformative would be an understatement. Twitter has completely changed my world view: the people I’ve had the opportunity to work with, the ability to help grow a business from a promising new entrant to a $1b+ annual market definer, and the experience of watching a product change the world have all been breathtaking. I feel especially honored to have been coached by the best and brightest in this industry, and without question the nicest, most supportive and innovative people I will ever have the opportunity to surround myself with. Furthermore, I am humbled by Twitter’s continued commitment to its values, most importantly growing our business in a way that makes us proud. I feel proud to represent the blue bird, and that will not stop despite the change of scenery.

I’ll be taking these next two years to figure out what the next steps are for me professionally (and documenting it along the way!) Business school is a time to learn, meet people, and reflect on what I expect will be fun career choices to come. In the meantime, you can expect that I’ll be live-Tweeting the whole thing, so follow along here.

Next Steps

Musings On Hiring


I’ve recently embarked on a very exciting professional journey: hiring a team. I could not have imagined how drastic the transition between being an “individual contributor” and a hiring manager would be unless I experienced it firsthand. I wanted to catalog some of the things I have been learning through this process of endless phone screens and team definition.

For full disclosure, I feel lucky to have the support of my peers, direct reports and my own manager who are helping me stumble through some of the challenges of being a first-time manager. The first and most important lesson so far is that it’s a marathon, not a sprint. These things take time but it’s worth the effort. Oh and hey, I’m hiring!

1. Have a clear vision of your team structure before you begin hiring.

Even if you have been given a distinct number of headcount, envision what your team will look like in 12 months. 2 years. 3 years, etc. How do you expect to grow and scale the team, and how will this person play a part in that expansion? What are the expectations you have of this person as the team changes?

2. Keep phone screens to 15 minutes of talk time. +5 minutes for questions at the end. 

Keeping it short and concise allows me to have some time at the interview to reflect. The truth is, you don’t really need a full 30 minutes to get to know someone, and there is no way that person can tell you everything he or she has done in depth in that amount of time. Keeping it surface level means you can reduce the amount of time actually spent on the screen.

3. Trust your gut. You know within the first 3 minutes whether or not this is someone you can work with.

Follows from the last point. When you know, you know. And generally you know pretty quickly.

4. If you talk more than you’ve listened, you’re doing something wrong.

I talk a lot so this one has been particularly hard for me. You can’t get a strong sense for what a person has done unless you give them unbridled time to speak freely. It also indicates how well this person knows to discern what is important to tell, and what is better left for a longer conversation.

5. Care more about the questions they ask you than you ask them.

It’s a 2-way street: they’re testing you as much as you’re testing them. A smart interviewee will know that and will take time to ask intelligent questions that will help them assess whether or not this is the right opportunity for them. The savviness of the questions is also indicative of the kind of work they’ll do and the way they work with other people

6. Assume they’ve done their homework. Ask the kind of questions you would ask someone on your team and see how they respond.

When it comes to really testing how qualified someone is, assume that they are another member of your team. If that person is able to answer questions in a way that would be satisfactory for anyone else on the team, you’ve found a suitable match. Sometimes these things are coachable (especially when they are product- or company-specific) but often you can deduce if they have the soft skills or not.

7. Ask your peers if they would hire that person for their own team. Rely on other people’s feedback. 

This is the most accurate benchmark of whether or not you should hire the person. As my colleague says “A players hire A players – so get the opinion of the other A players on your team”

8. Ask yourself if you would work for that person some day. 

One of the smartest people I work with gave me this advice. Some day, the tables may be turned. Hire people you genuinely want to work with and who can teach you as much as you can teach them.

9. Hire people who have skills you do not. Think holistically about your team.

For example, I’ve never done sales. My function is a support function for revenue generating teams, but without the perspective of someone who has actually done that job, it’s hard to put myself in a seller’s shoes. Hiring someone with that vantage point can fill a void on the team.

10. Once you’ve made the hire, set expectations for your current team and your new employee.

It’s better to have transparency than to keep people guessing. Be honest about that person’s leveling, and what it will take to see the new hire grow and flourish in this role. Also, be honest about the kinds of opportunities this role affords after that person has grown out of it. This way you can work toward a shared set of goals.

Bonus points: I’ve been taking inventory of all of the things I’ve learned from my managers. What worked and what didn’t in each of their styles. I’m even drawing upon managers I had years ago in banking or summer internships. I feel fortunate that I’ve had some positive, strong managerial influences over the last 5 years.

Musings On Hiring

25: A Year In Reflection


Tomorrow is my birthday, and generally I like to look back and reflect on the year that passed. 25 was a big one for me both personally and professionally, and I thought on my last day of this great year, I would share 10 of the most significant things I’ve learned this year (lots of platitudes, not all corny). Thanks to all of my family and friends for teaching me so much this year!

1. People don’t mind a bit of self-promotion: In anticipation of releasing a book, I wasn’t entirely sure how to “market” it to friends and family. I seldom post on Facebook and I don’t love making asks of people. But I had to get over that pretty quickly in order to begin publicizing and once I took the plunge, in good taste, I got over the fear.

2. Only take leaps, not steps: Obvious, I know. But sometimes we lose sight of this in the day-to-day routine. It’s hard to step back and ask “is this really going to propel me forward in the long run?” or to find opportunities in between the cracks. This year, more than ever, finding the hidden leaps has been critical and I hope the momentum can continue. Leaps often lead to better risk/reward situations.

3. You don’t have to know everything to get the job done: The 80/20 rule would say you need 20% of the information to get 80% of the job complete. That’s true in most circumstances. Use it to your advantage to maximize your efficiency and time spent on any one endeavor.

4. Multitask all the time: I’m the kind of person who likes to work on as many projects at once. I know my limits and I recognize when I’ve reached my capacity to output quality work, but I try to stretch that as frequently as possible. I enjoyed writing a book, advising companies, running an employee resource group and planning personal endeavors at the same time (in addition to my job). It always gives you something to do.

5. Meet someone new and completely outside of your comfort zone as often as possible: Dr. Meg Jay, who wrote The Defining Decade, talks about a concept known as “the strength of weak ties.” These ties are usually people you don’t know well, or might even be connected to as a friend of a friend and they are ordinarily the ones who help you see things from an objective perspective. They might be the person to think of you for a job or connect you to someone beneficial to your business. I try to expand my horizons as much and as frequently as possible.

6. Respond to blind reach-outs: they can be fruitful connections and can even turn into great opportunities to connect. I try to talk to everyone, schedule permitting, or at the very least correspond with email. On the flip side, I really struggle with ambiguous asks in reach-outs. So be specific and you will prosper. I try to take my own advice on this since I constantly reach out to people, and am learning about various kinds of response styles.

7. The collective is much more powerful than the individual: I have been used to doing all of my own work and taking care of matters by myself. Learning to delegate and collaborate this year, in particular, has been game-changing. Lean on others who know more than you. Don’t be afraid to delegate to someone who can do a better job and don’t let it affect your ego. Work with your team or partner instead of siloed, especially if you are working toward a common goal.

8. Challenge all assumptions, but let yourself be surprised once in a while: being discerning about minutiae usually gets the job done and gets it done well. Push back on assumptions you are given and be skeptical of other peoples’ suggestions. Letting your guard down every once in a blue moon can sometimes yield really beautiful things. I would also put into this bucket: my skepticism of targeted advertising that has a much more successful effect than I always think it will.

9. Always ask a question: 90% of the things I’ve learned in the last year, and much of my success to date, has been because I ask a lot of questions. You can seem just as intelligent if you ask a question than if you know the answer. Inquisitiveness is a virtue.

10. Nothing is better than doughnutsHonestly I learned this one 25 years ago.

Here’s to the other side of this decade…

25: A Year In Reflection

Inspiring and Motivating a Team: How to Rally the Troops


I’m back. It’s been a busy month both personally and professionally. I’ve been halfway around the world and back, and it’s been eye-opening. But I’m here again to dispense some unsolicited advice.

This week, I’ve been thinking a lot about how people are motivated and how teams progress day after day, week after week. Of course, there’s some energy around working in a team environment in the first place. We feed off of others’ enthusiasm. There is also excitement around the actual nature of the work itself. But there are a few additional connectors that glue a team together and inspire employees to continue working, that in my experience have catapulted teams/products/companies forward.

1. Staying organized: some leaders want to stand on a soapbox and rally the troops behind one idea. But rhetoric has to be organized effectively in order to understand exactly what the plan is. This organization must be consistently refreshed and revamped, otherwise people won’t know what plan they are executing against.

2. Innovating: Giving a blank slate can yield incredible results. Motivating a team by giving them the autonomy to come up with a completely new and innovative solution can be the ultimate driving force. If the team believes that they are simply rehashing old ideas or building on top of existing processes, the excitement wanes quickly.

3. Delegating and expanding scope of team mates: The best individual motivator is to push people’s skills beyond what they thought their capacity was. If you are asked to keep producing work at the same level, you will never feel motivated to go above and beyond what is asked of you.

4. Sharing inspiring stories: motivate your team by sharing successes. They don’t have to be directly related to whatever the team is working on, but have concrete examples rooted in the same moral lesson of perseverance that sends the same message.

5. Generating original thoughts and content: as a close confidant always says, “leaders innovate, impostors copy.” If you need to motivate your team, don’t repurpose someone else’s stories or reuse content someone else provided for you. Bring it from the heart: share your own story or first-hand anecdote. Come up with your own strategies rather than directly copying someone else’s. “Steal with pride” is ok, but make it your own.

When teams don’t do these things, they grow stale. People grow stagnant and disillusioned. Progress is not achieved. And employees lose sight of the greater vision, which makes it even more difficult to move quickly and make change. As a leader or as an individual contributor, it’s important to consider whether or not you are doing these things or providing the framework for them to happen in order to continue to motivate yourself and those around you. Occasionally, these actions shock the system that enables progress and inspires members of the org.

Inspiring and Motivating a Team: How to Rally the Troops

Work Smarter, Not Harder



People brag about working 100 hours a week – the badge of honor that you’ve slaved at the office all those nights and weekends. If you are really working on something worthy of that kind of attention, then this is a commendable effort. But for the most part, the majority of those hours are wasted on fruitless pursuits that don’t make it into the final version of the project.

Work harder, not smarter is the professional motto that I strive to achieve on every project I execute. The number of hours I work doesn’t necessarily correlate to the efficiency and scale to which the project got done. In fact, I’d like to think that if I’ve maximized the best output with the best input, I could get things done in a reasonable amount of time.

Working smarter means putting things on paper before you get started – making a project plan or an outline before diving into the work itself. It also means stepping back every 10% milemarker and assessing whether or not you are working on something relevant. For example, when I was recently putting together a business plan, I found myself going on random analytical tangents. Stepping back and saying “does this really matter?” or “Is it worth the trouble to get this one statistic?” were helpful in keeping myself tracked and focused.

In order to work smarter, you also must dissect a larger task into smaller, mutually exclusive chunks. This ensures that if you hit a roadblock on one of them, you can easily move to a different assessment while you are waiting for a resolution. Remember: efficient use of time means you are working smart.

Blindly working hard can often mean spinning your wheels on something that isn’t necessarily relevant, which is a time waster. If the goal is to get work done in an efficient manner while retaining the rigor and accuracy of high-quality work, mapping and planning will ensure that you work smarter, not harder.

Work Smarter, Not Harder

Done Is Better Than Perfect


In school we are taught to target the right answer. I envision the math problem sets that encouraged us to show our work and neatly box the correct answer at the bottom – and we were ultimately judged on the basis of that answer. But in the fast-paced world of tech, that approach doesn’t exactly work. Beyond the question of “what is the right answer?”, we have an adage on my team that done is better than perfect.

“Move fast and break things” is the motto that enabled Facebook to grow so rapidly. In the context of moving quickly, getting something done in a timely manner and on paper can actually be more valuable than being 100% accurate. Usually, getting to that level of accuracy requires modeling or precision that isn’t necessary to make an informed business decision.

This is predicated on the idea that there is a right or “perfect” answer, which there usually is not. In the tech world, you’re usually trying to solve problems that haven’t been solved, or answer questions that have never been answered. Cranking away until you get the right answer when the solution can usually be discerned at 80% of the way there means you’re wasting time when you could be working on something else.

Of course, there are instances in which you precision is imperative: you might need to propose 1 exact number or finish the demo of a product. For the most part, having an MVP – a minimum viable product, is enough to propel you to the next step of whatever you’re working on. If you’re going to move quickly and keep up with the market, done has to be better than 100% right.

Done Is Better Than Perfect

Ask For What You Need

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I’ve been working on marketing Pitching & Closing and am learning a lot in the process. I have never done any form of marketing before (other than perhaps my own personal brand) and it’s been an interesting experience understanding how to spread the word. Part of this marketing means asking people for various things: favors, purchases, introductions etc.

In this process, I have also had to learn very quickly how to ask for what you need, not what you think the other person wants to hear. This is a common need in sales and business development and is a very practical skill to have.

For example, Alex and I have been speaking with various universities and academic institutions about using the book in classrooms. Having to make the ask outright: is there any way a professor, teacher or department would consider adding it to the curriculum? Even if you think it isn’t entirely feasible for the other side to meet your exact needs, making the full ask makes it easier for the other side to meet you halfway.

It’s as simple as ripping off the bandaid and knowing very clearly what you need from the other side. Make your ask specific and detailed (like, I’d like you to consider using the book in this particular course for 1 semester as a trial-run), and the other side will be able to form its opinion – and hopefully say yes. The worst thing that happens is you get a “sorry, we can’t help you at this time.” But the clearer and more precise the ask, the more likely it is that you can find a compromise for both parties.

Ask For What You Need

Whom to Follow


I ordinarily keep a Chinese wall up on here in posting about the platform on which I work, but lately I’ve been solicited for advice on whom to follow. My opinion is one of many, but since I am a frequent-user, I thought I would share my latest advice on some of my favorite accounts to follow on Twitter.

Everyone has his or her own follow philosophy. I am not a static follower but rather a rotator: I follow an account of a “trial run,” and if after 30 days or so (not scientific) I don’t find I derive much value, I usually unfollow or replace the follow. In addition, I find that certain accounts do it for me at certain stages of my business cycle/personal interests/macro interests and then stop being of use, and so I’m happy to unfollow and rotate the account. As a result, I’ve followed some interesting and far-ranging accounts, but I keep my feed clean and decluttered. Follower count right now? 420.

Disclaimer: I don’t personally know anyone on this list, so it’s just my genuine sentiments here and people I enjoy following (of late).

  1. Alyson Shontell (@ajs) – Alyson is a reporter for Business Insider, and I find she always has good insights on the tech markets in an actionable way. I learn a lot about cool, interesting products or the philosophies of important people in the tech space from her feed.
  2. Faces In Things (@facespics) – I’m not sure why I find this account so hilarious or entertaining, but it never disappoints. People submit images of things that looks like faces (but aren’t meant to).
  3. Rob Delaney (@robdelaney) – sharp and incredibly sardonic stand-up comedian who occasionally challenges Walmart and Lena Dunham. It’s basically a crime not to follow him.
  4. Marc Andreesen (@pmarca) – Marc is a prolific VC and has also become an incredibly active Tweeter since the start of 2014 (he’s racked up almost 24k Tweets in that time). He’s the father of the tweet rant and inventor of the “1/, 2/, 3/” syntax.
  5. Magic Pics (@magicpixx) – autoreplies to tweets of yours, at random, with a seemingly-related photo of your tweet. They often don’t match. Hilarity ensues.

Honorable mentions:

Saved you a click (@savedyouaclick)

Karl the fog (@karlthefog)

Who are some of your favorites? What’s your follow strategy? Tweet @ me.

Whom to Follow