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

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.

Email, the Operating System for Life

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Why you should bring your interactions to the place where people already spend their time.

Email is the #1 Destination

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Ryan Hoover published a great article the other day on the trend of using email as an interface to do other things. You probably already use it in this way by sending commands to other systems: “forward this email to my expense site”, “watch my email for interesting stuff,” and “make a to-do list out of my emails.” In my experience, managing tasks through email (though hopefully not using your inbox) increases productivity and makes you generally better at getting stuff done. And there’s a bit more that we ought to be doing.

The “stuff we ought to be doing” varies, and usually relates to long-running recurrent tasks (remember someone’s birthday, maintain a daily or weekly status), project-based tasks with a deadline (I need to get some stuff done before next Wednesday), and one-time actions (“Can you find this for me, right now?”) Email is really lousy at these things, which is why we use other applications for help.

We need a better way to surface applications and services in email without breaking the way people handle email today.

Remember. All. the. Logins.

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Awesome! You remembered all of your passwords (or have a great SaaS app to handle that.)

There are so many great applications that are out there (many are even free) that can get stuff done. Now, which ones should we hire to do the job? And what job are we actually doing? Just managing the logins can be a chore, and getting beyond that to switch contexts every time you want to start something new can waste a lot more of your time.

Getting started isn’t easy.

One of the great challenges of Software as a Service products is that there is a login to remember, a site to visit, and tasks to do in that other system that will help you to better manage the minute details of the things you do. You might use Sprintly for Agile Dev, for Customer Service Interactions, Expensify for Expenses, and so on. Yet all of these products depend upon you start an action in email and then resume it in another system.

So which app was I using to do that?

When you make constant decisions that force you to have another login, another app to pay attention to when you’re on the go, and yet another slew of notifications, you dilute your ability to make quick decisions. It’s a mental burden to understand which things really need attention and which notifications arrive as a result of long-forgotten decisions that are no longer important.

Ok, Now What?

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When you build an application – and need customers to participate – it’s your job to find the place and interface where they will get the most value out of your idea. I believe you should not only make your service responsive but also your service design responsive.

Towards a Responsive Service Design

Making a basic responsive design is pretty straightforward – making an insanely great one is really hard. I think the same is true when you invent a responsive service design. Making your service design responsive anticipates that customers will use different modalities and interfaces to access your idea, and that some customers will never cross into another way to use your idea. App customers may not behave the same as email customers, and vice-verse. But there are a ton of people using email, so how can you add value to their experience without being overwhelming?

Service Design as a concept implies that there are activities that customers take to get tasks done. Completing the tasks may require external actions and may depend on other tasks or actors. Finally, the activity you are designing may happen in multiple places.

Email to the Rescue: The Lowest Common Denominator

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Because people spend lots of time in email and there are already many ways to access it, email is a great candidate to act as an operating system where customers might do these service tasks as part of an overall service design.

There are three basic ways you can push email towards being an operating system of sorts:

  1. Create a browser extension – force your way into the experience, either passively (Klout in adding scores to your Twitter pages) or actively (Rapportive, adding persistent information to the existing real estate)
  2. Invisibly solve a problem – have a background service that listens to email and makes decisions or surfaces information based on your preferences (Sanebox, for example, which automatically files your messages)
  3. Take explicit email commands – “add note”, “send tweet”, etc and make them easier to use for “normal” people and abstract them to other media

Time to fight the blank page

All of these methods have advantages and challenges – let’s take a look.

Make a Plug-In

You could make a browser extension that will either take over the real estate or silently monitor or insert information in the places you’ll most likely interact with other services. Plug-ins are awesome for absolute control and transfer very poorly to other interfaces.

As an example, I love Rapportive because it does a great job of using the mostly empty screen real estate I used to see in Gmail and fills it with valuable information about the person who is contacting me. It even shows me the latest view that other people using the same service have of me. Rapportive is a great experience because it exposes some methods to other application services I use (send invitation, start tweet, read Facebook post) without cluttering my view. Some drawbacks of this method are that I don’t have any more mental space for more plug-ins. I’m sure that was one of the reasons LinkedIn purchased this scrappy team.

Create an Invisible Service That Does Your Work

Another way of approaching this problem is to work behind the scenes and make the changes necessary to increase productivity or other goals. This method is cool because it’s client-independent. And it still requires developers to create different interfaces in different client. (There’s less to customize, though.)

Sanebox just works – it filters the email I receive into Gmail labels and then gives me a single digest a day to take actions. From my daily email digest I can delete unwanted messages, set reminders, and see how I’m doing relative to prior days or weeks. When I want to ignore Sanebox, it’s still doing work for me and allows me to close email for long periods of time and then solve for a burst of emails all at once. I don’t have to worry about filing any more – I just search.

Another version of this implementation is the inverse of a service that is implemented everywhere – Mailbox lives only in an iPhone app and allows you to connect to many email clients and apply the same simple management effort to each one. Mailbox takes the best metaphors from the mobile interface and applies them to email: swipe to promote an email to a task or to archive or delete it.

Make external tasks possible in Email

The traditional, geeky way to make external tasks possible in email is to require the customer to send an explicit email command in a subject line or in an interaction body so that the server on the other end of the “conversation” knows exactly what task to execute. In practice, this works well for “send my stuff to you and have you process it” and is harder to execute for “do only the thing I want you to do and not that other thing based on the thing I type.” Normal people – that is, people who don’t talk to computers all day – have a hard time doing this.

Yet the potential exists – many of us use Siri, Google Voice Commands, or interfaces like Google Glass to create a graph search-like call and response with our services. So let’s do that with email – and that’s where Google is going.

courtesy of

Google’s version of this is borrowed from another company, however. Their previous versions of “do stuff in your email” were possible only for geeks to do. You needed to install a “Labs Feature,” or use keyboard shortcuts, or do other things late adopters don’t tend to do. And what’s the solution? Apps that magically show you what to do and offer fewer choices and fewer configuration steps.

We should thank Facebook and Apple for priming customers to act this way – the app economy makes customers expect one-click actions to solve their problems. So now it will be possible for publishers like Google to create structured, in-context actions for customers to complete and interact with other systems. Some will call this backsliding and the new “Death of Email.” I call this the birth of “Email, the Operating System for Life.”


originally published at Medium.

The Customer Experience Report for Jan 26, 2013

Hello! I’m sharing insights about customer experience.
Please let me know what you like, don’t like, and if you’d like to subscribe, you can get an email in your inbox here.

The Customer Experience Report

January 26, 2013 – An Occasional Newsletter (Vol. 2, No. 1)
Rules for Better Customer Experience: Hacking Your Brain

Brad Feld shared a story about meetings and making them better this week, including the memorable rule #0: Do We Need To Meet? This story made me think about the process of customer engagement and of a few suggestions that can make the process of delivering and receiving the experience better all around (and not just in meetings).

Hack Your Brain to Change the Situation
These suggestions have to do with brain hacks: specifically, the idea of reframing the situation and of suggesting a “Best Practice.” Reframing means to present the scenario so that you can change the way that people see things and suggest an alternate solution.

In my experience, one of the most powerful reframing tools is “The Happy Path” – it’s basically a way of saying “when nothing goes wrong, this is the best expected outcome for the process” – and suggesting this path to the customer. When the customer is closest to the ideal persona (a user model popularized by Alan Cooper), then the combination of the Happy Path and the ideal persona can produce a documentation of the ideal customer experience.

Matching the Happy Path with the Real World
Except when it’s not the ideal customer experience, because as we know, the Happy Path and the Ideal Persona rarely meet. It’s also really important to be able to say no instead of maybe to a customer who’s trying to do something that doesn’t really fit the experience.

It’s tempting to let them wander on and come up with an “almost” solution, and this often causes problems later on from a support or experience perspective when the “almost” solution encounters a hitch or a bug or a change of mind. So how can you introduce a bit of the Happy Path to the customer without diverting them dramatically or by trying to create a kind of customer model that they can’t ever meet?

The Just-in-Time Happy Path
One way to do this – especially in a feature rich product – is to uncover the right solution to a problem that they didn’t know that they have yet. An example from the CRM and Customer Service world is the ability to combine merge text (variables that substitute values from a case, customer, or company) with pre-written or “canned” content. By adding this very simple change, you can turn formulaic content into something a bit more personal, and streamline what could be a tedious manual process.

How can I learn more about Personas?
To get started, you can read the Cooper Group’s Guide to Personas. You should also read this article about making personas your team can actually believe in and embrace. Finally, consider this article about making sure that the details of your personas are grounded in fact and not just in vague description.

tl;dr: Customers may have a hard time finding The Happy Path on their own, and as an expert, you need to share multiple happy paths they can traverse.

Great stories from this week

Why our brains like short-term goals (from Entrepreneur Magazine)

Setting an experience and a reward is better than just money (from Digital Telepathy)

Using Bloom’s Taxonomy to Teach Critical Thinking (via @getlittlebird)

You can also find up-to-date customer experience tidbits here

You should learn to code today

stretch your brain by coding
Even if the code is simple, there’s lots to learn.

What can you get done in a day, or a weekend?

Today, I learned how to call my phone automatically today with a REST API and to play background music when the caller picked up. Yeah, you say, that’s easy if you know how to use Twilio (which is what I used) but the interesting thing was how I learned it. I used Codecademy – a web site that helps you to learn how to code – and it was completely free.

While some folks might think that learning how to code is a waste of time, I’d like to politely rebut that statement and say that it’s absolutely necessary for you to learn how to code and that it’s a vital use of your time. There are a few reasons you should learn to code today, even if you have no intention of ever completing a program or shipping code in a production environment:

Ask and Answer Better Technical Questions

The first reason you should learn to code today is to begin the process of translating geek to english. If you can ask programmers and techies types better questions you will annoy them less, get better at getting answers to the questions you want to answer, and build a better rapport with your technical team. In my experience, the practice of asking better technical questions helps you to understand the basics of a technology as an engineer does (what actually happens when you post an HTML form, rather than thinking of it as a black box, can help you grok the limitations of submitting and validating a post to a web page.) You won’t be able to deliver production code by working on a Codecademy course, and you will start to understand the scope of the problem and get closer to the actual doing of the work.

Make Your Brain Better

The second reason you should try coding is that identifying, trying (and sometimes failing), and succeeding at a new skill will stretch your brain. Among other things, learning new skills provides dopamine to your noggin and gives you a feeling of accomplishment. Even if you’re lousy at coding, there’s something cool when you type puts “hello, world” and the computer echoes back what you wrote. No, you’re not ready to ship code, but it’s the smallest big thing that you know how to do and gives you a framework for learning additional tasks should you get interested in learning additional new skiils. You’ve got to crawl before you walk, and learning new things may even make your brain grow.

You might have fun

Much like the lean startup idea popularized by Steve Blank when he tells entrepreneurs to “get out of the building”, learning a new skill like coding is constant practice in getting out of your comfort zone. It feels uncomfortable to learn new syntax, be specific enough so that an interpreter running inside of a web page understands what you’re trying to do, and to speak computerese. You might have fun and learn a new skill, or you might just stretch your brain. The effort is worth the effort, and “learn to code” isn’t the only skill you want to build, it’s your brain’s plasticity and resilience. Learn one thing, and you can learn more things effectively.

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