Career, Generous, On Writing, Startup, Uncategorized

When you get a chance to go back to a great team, jump at the opportunity!

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Have you ever been on a great team?

I mean the kind of team that people and alumni talk about years later. I’m talking about a team that produces results, leads the market, and is the kind of team that spawns other great teams. It’s hard to produce these kinds of results once, so it’s all the more remarkable when the same team produces another high-performing team (and highly correlated to success in the new venture)

In my career, I have been on great teams, and also participated in not-so-great teams.

Here are a few things that great teams do that mediocre teams do not do:

Great Teams Focus Their Efforts

In a startup (or really inside any company) there is always too much to do and almost always not enough time and resources to do it. Great teams build a culture where people focus on the next best thing they can do to improve the company, and make it easy for people to work together to gain results. For example, when you cut a lightly used feature and take the time to improve an existing feature, you are lowering the surface area of your product and helping the whole team to feel better about the quality of your software.

Mediocre teams work on many projects at once and never ship. On these teams, someone always claims credit for doing the work instead of giving kudos to another team member to congratulate them on a job well done. Mediocre teams endlessly add features without taking the time to ask customers whether the existing features meet their needs.

Great Teams Identify and Amplify Team Strengths

On a great team, it’s easy to find specialists. They are busy doing what they do best – not struggling at tasks they do the worst – and producing strong results. Some of the specialists have a specialty of getting other people to make decisions, push themselves to do new things, or to reduce the overall quantity of work to produce higher quality work. Great teams form around individuals who have strengths the whole team can use. These teams ask “how can I help?” to each other rather than saying “I’m too busy – can you ask someone else?”

On a mediocre team, it’s hard to determine what anyone does well, because everyone is meeting with each other in the same meetings. There is no time for work during the work day, because no one comes prepared to discuss items at meetings, and people spend the meeting time multitasking and doing the work they could not complete in their previous meetings. Mediocre teams leach away the strength of their individual specialists by creating an environment where no one knows how to make a decision and where no one feels empowered to ask for that decision.

Great Teams Are Resilient

Having a great team does not isolate you from conflict. Great teams are effective at meeting conflict head-on, discussing the problem, finding a solution, and then moving forward either by “disagreeing and committing” or by genuine consensus. These teams are resilient because during times of trouble team members lean on each other’s strengths and find solutions to seemingly intractable problems.

Mediocre teams fall apart or descend into chaos during stressful situations. There are few things more disappointing than thinking you’re on a great team, encountering a stressful situation, and then realizing your team is rather mediocre. Instead of the support you get from a great team, on a mediocre team it ends up being every person for themselves.

Great teams are hard to find.

I recently joined the team at Kustomer because this is a great team solving a hard problem in an important market – CRM for support customers – and I wanted to be part of that effort. So far, working at Kustomer feels similar to the atmosphere I shared with some of the team members when we worked together at Assistly. We work hard, we play hard, and we are building a business centered on our customers. But what makes a team great?

Great teams sometimes form by themselves and sometimes are made. People know a great team when they experience it. Great teams do not last forever, because culture is hard. When you get the band back together, it doesn’t always work. But when it does, it’s amazing.

Kustomer is a great team. We are crushing it. That doesn’t mean we’re always right – it means we are going after a great market with proven technology expertise, deep domain expertise, and a kick-ass attitude.

Career, Customer Experience

The first goal is to keep learning

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My first goal as a college senior was to have the kind of job where I would never have to wear a tie. Achievement unlocked. But that didn’t really get to the core of the issue. I was really trying to decide what I wanted to be when I grew up. A person who helps customers every day was the answer.  Continue reading

Career, Life Hacks

What is your Superpower?

Courtesy of ap-photographie on Flickr
Courtesy of ap-photographie on Flickr

What is your Superpower?

Are you Super? Some programmers are 10x+ times better than their peers. And this distinction applies to team productivity in general. It makes it really important for you to know the thing you do better than anyone else. Doing more of that thing will make you happier at work and in general.

What is the one thing you do better than anyone else? If other people were to talk about how you interact in the world, what’s the “signature strength” they would talk about when they talk about you? Continue reading

Career, Innovation, Life Hacks, Startup

We do startups because we can’t not do startups.

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This essay is written in collaboration with Startup Edition – find this week’s essays here.

The startup life seems glamorous from afar, and sometimes from up close. There are rebels, pirates, and ninjas here. There are rags-to-riches stories and others who fall from grace after flying too close to the sun. In short, there are all of the archetypes you wish to see in the startup world. So how do you get a job here?

The short version of this answer is: we do startups because we can’t not do startups. Startups are the fastest way to level up personally and professionally. Startups make powerful friendships and lifetime bonds among teammates. And startups are a place where people do amazing things and learn how to do things they’ve never done before.

Startups are also emotional roller coasters that demand the routine of a monk to fight the continual randomness of change. Startups give you the opportunity to make bigger mistakes than you’ve ever made before. And startups are the place where you can’t hide behind a meeting or a title to avoid doing work. You must own your problems, and your successes.

So, Why should you work for a startup?

You should work for a startup if you like challenges. You should work for a startup if you like the idea of lifelong learning. You should work for a startup if you’re a person who is resilient and doesn’t want to know what they are going to do day after day. And you should work for a startup if you want to push yourself to do more than you ever thought possible and only realize it when you look back and see what’s happened.

Ok, I’m good – how do I get started?

Startups need doers. They also need people who can seamlessly shift between strategy and tactics. You need to be able to roll up your sleeves and do whatever is necessary to ship your product, make your launch date, and finish your code. You also need to remember that you have a life – and to make space for yourself and the things that you believe it – or you will be consumed rather than tempered in the startup fire.

Start by doing, and with a beginner’s mind. That doesn’t mean that you need to do things at a beginner’s level, but rather to find the thing you know and can do better than anyone else. Now, find a way to present that skill as a benefit for a business. Next, find the business that need that benefit.

Finally, never think that you’re done learning. We’re all wired to think that life is static. In fact, there’s change happening all of the time. So if you want to survive in startups – and elsewhere – you need to be resilient and practice improving the way you respond to change.

This essay is written in collaboration with Startup Edition – find this week’s essays here.


Career, Learning, Life Hacks, Productivity, Startup

There is always more work to do.

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This post is part of the Startup Edition series on Enterpreneurship

What’s on your To-Do List?

Right now you have something else to do. Later today you will also have something else to do. And tomorrow you will have the opportunity to pick new things to do and catch up on the things you did not get done from today. There are also the other things in your life that need attention – they might be family time, your spouse or significant other, that run you are putting off, or any number of side projects and obligations – so how do you manage stress and life balance as an entrepreneur?

I start from routine. Knowing what I’m going to do in a day helps me to prepare for the uncertainty that will also happen. I make sure that I cover my bases – eating well, making sure that I sleep enough, and going home at the end of the day. Eating well often means explaining to people that I avoid gluten, dairy, and egg, and it also makes it hard to eat while I’m on the road or away from my house. Sleeping enough is challenging. You can always get more done late at night, and I’ve learned through experience that late night learning  is just not as effective as the benefit you get from sleep. And I go home. There’s a lot of pressure in any office to be the first one at work and the last one leaving. Even better is the feeling that you can go home and still know what you need to get done.

What can you get done today?

You also need to know (and be able to identify) Your Most Important items to be able to leave the office and still be productive. I do spend the time at home to get done whatever needs to get done, and I usually do that after my kids are in bed. Protecting family time is one of the best ways I know to reduce stress and feel like I have a more balanced life.

Except when your life isn’t so balanced. Because as an entrepreneur, there are often times when the business/problem/idea is all-consuming. If you have built up goodwill with your family and/or significant other to be able to ask for the time you need, you’ll feel better about being fully present in your startup – and being able to put your phone/computer/work brain in the other room during family time.

Balancing Stress is an Ongoing Challenge.

Is this a perfect system? Heck no. It’s a strategy to balance the stress of being in a startup and to maintain the smallest version of a big goal that I have: to be present for the people who matter to me, in the moment when we are present together. I’ve made the mistake in the past of trying to double, triple, and multi-task. It feels successful while you’re doing it, and results in action, but doesn’t identify, move forward, and solve the most important things you need to get done. So spend your time focusing on the biggest small thing you can get done. Eat well. Get enough sleep. Move around. And hang out with the people you love.

Managing stress and life balance as an entrepreneur means getting very comfortable with ambiguity. The sooner you internalize that and learn what you need to do to cope with that uncertainty, the better. The bad news is that there is always more work to do. The good news is that there is always more work to do. Get that work done on your terms and be able to tell a great story about it, and you’ll feel like you are managing your startup on your terms. Finally, Perfect is the Enemy of Done.

This post is part of the Startup Edition series on Enterpreneurship

Career, Learning, Life Hacks, On Writing

Be right when someone asks.

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This essay is written as part of the Startup Edition project – check out the other essays here.


When was the last time you were right? Absolutely, positively certain with no chance of being wrong. Now, think of the last time you knew you had the answer, and someone asked you to be right? How did that feel?

If there’s one lesson I could share with young entrepreneurs (and with my younger self), it would be that you should only try to be right when someone asks you for that absolutely certain answer. The rest of the time, be nice – wait for your moment until you get asked the question you’ve been anticipating.

Can you gather facts? Sure. Can you prepare persuasive arguments? Absolutely. And until someone’s listening, those facts and arguments don’t matter much.

What does it mean to be right at the wrong time?

Being right doesn’t prove you’re smart – it often proves that you are impatient and can’t wait for the right moment to make your point and back it up with the information the other person or people need to understand. Being right also doesn’t make you right in a given situation (sounds strange, right?)

Compare and contrast the feeling of blurting out the right answer in a crowd that hasn’t asked for it yet against the feeling of being just the right person to answer just the right question at the moment it’s asked. Answering the call for an important question can be an amazing feeling – you get to show how smart you are, you know you’re solving an important problem, and you know someone actually wants to hear the answer.

On the Importance of Timing

Wait, you say. Aren’t some of the most important questions the ones that haven’t yet been asked? Yep. That’s true also. And if you can manage to lead an individual, a group, or an audience to ask you the question that you know how to answer and help them to feel that it’s their question? That’s charisma – the ability to lead and inspire without the implication of being a know-it-all – and it’s a great goal to pursue.

There are other lessons young entrepreneurs need to learn. These are ideas like “do more of what you love,” “hang out with lots of smart people and interesting things will happen,” and “don’t spend too much time at big companies without also talking to people at small companies.” You’ll find lots of these ideas (and the ones that work for you) by continuing to learn and meet new people.

When you meet new people and want them to listen to your ideas, answer the questions they ask. If they haven’t answered the question you wanted to ask yet, guide them to ask it. You’ll be happier when you see the spark in their eyes as you enthusiastically answer the right question.

This essay is written as part of the Startup Edition project – check out the other essays here.

Career, Lean, Learning, Life Hacks, Product Strategy, Productivity, Startup

Two of the Dumbest Business Mistakes I’ve Ever Made

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//Read about more mistakes in the newest Startup Edition

“Do not fear mistakes. There are none.”
-Miles Davis.

We all make mistakes.

I’ve made a few mistakes in my time. I’m not talking about the garden-variety mistakes you might make in the course of the day. I’m talking about product development whoppers, or the kind you look back on several years later and wonder, “What was I thinking!?”

You make the best decision you can based on the information you know at the time and your framework for making decisions. There are a few decisions I wish I could take back, because if I could change them now, they would be great companies (or at least, I could feel like I made the right decision 10 years later). They were ideas for products that I still want now, that still solve a concrete problem, and that people are still willing to pay money to solve. (These ideas also work because they enable the businesses that use them to make more money and get more yield out of their current investment.)

What was my biggest mistake?

My Biggest Mistake was not trusting myself to make the right decision with the information I knew at the time. I didn’t have all of the answers – how to execute, how to find the money, how to deal with the ups and downs of being an entrepreneur – and I let that feeling of being out of my comfort zone make my decision for me. The lesson for next time? Be comfortable with being uncomfortable. Trust my gut more, and be in the moment when struck by a big idea that wants to be real.

Now, you decide whether I should have gone forward.

Here are the ideas that I had and decided not to do. Read them with the knowledge that you have in 2013, and decide whether you would pursue them today: I would.

Big Idea: Make the Grocery Store Easier.

Idea #1: Imagine if the next time you went into your local grocery store, there was a way for your phone to tell you the location of every product in the store, to remember your past preferences for shopping, and even to direct you in an optimal aisle-by-aisle route to minimize the time in store? And what if you received loyalty rewards and marketing offers that pertained to you? And what if you could check out of the store simply by scanning each item with your phone as you placed into the cart. That idea sounds promising and real in 2013, and quite similar to the idea my friends are pursuing at qThru.

When I thought of a very similar idea in 1999, even though the hardware and software was off the shelf and readily available, I didn’t go and build it. I made the decision that “I wasn’t the type to do that,” and “I’m not an idea guy” and let self-doubt make my decision for me. I can’t have that decision back, and I know that what I was really feeling in the moment was, “oh crap. I have no idea how to even begin thinking about that much less how to build and monetize it.” And, it happened again.

Big Idea #2: Make Waiting at a Restaurant Better.

Idea #2: Imagine you arrive at a popular restaurant. Because they are very busy, they ask you for your phone number so that they can text message you when your table is available. At the same time, they ask you to join their loyalty program so that you can participate in drink specials, learn about special events, and play games or trivia while you are waiting in line. It exists today – it’s called TurnStar – and I’ve used it. It’s pretty slick.

Why didn’t I build my version? It was called TextMyTable, and I was ready to go with the vision, the business plan, and the execution play. It was September 2008. Then all of a sudden the economy did a flip-flop and all of our assumptions about what was a normal business turned on their head. Or did they? I was stuck because I didn’t know how to raise the money to start the business or to grow the business in such a way that it generated operating capital.

What’s the Commonality?

In both of these ideas (and in others it’s not important to share here), I had an idea for a product or a service that was innovative. The ideas capitalized on a consumer need, solved an actual problem and had a reasonable chance at being successful. We could argue about the size of the market and the relative degree of success, and the fact remains that they were good ideas. And I made a mistake in not pursuing them.

What did I learn and what would I do next time?

The first thing I learned is that you can’t find out whether you’ll succeed with an idea until you try it. (Duh.) The ideas I think that would have been successful might have been abject failures, wild successes, or more likely somewhere in between. And I don’t know because I didn’t try them.

The second thing I learned from these mistakes is that collaboration is everything. I needed to do more to ask people to tear apart the idea instead of trying to build the whole business from start to finish inside my head. Groups like Startup Edition are a great place to get feedback, learn from other perspectives, and to reframe your questions.

And finally, I learned from my mistakes that it’s impossible to know what you don’t know until you do it. (Sounds like a Zen koan, doesn’t it.) What can you do about that? Admit that you’re going to make mistakes. Try to make different ones the next time you approach a problem, and learn from the results. Trust your gut.