Hitting Send – Guiding Questions for Writing Better Business Emails

January 11, 2015 in Work Smarter

“Don’t worry if I write rhymes, I write checks” – P.Diddy

A big part of getting deals done boils down to sending the right email.

It seems almost trivial at first, but upon further reflection, this is actually one of the most important things you’ll need to master if you’re hoping to acquire early customers for your company.

For anyone who spends a lot of time thinking about the perfect way to word an email, having a list of key questions to mentally go through can make the difference between a response and radio silence.

Here is a checklist of questions that I’ve found useful right before I think about hitting the Send button:

1) Benefit Focused: Is the email customer centric? Is each sentence phrased in a way that is useful information for the reader? If the reader was thinking “So what? What’s in it for my company or me?” after each paragraph of your email, would the “So What” be answered?

2) Tone: What is the tone that I want to convey? What do I want them to feel after reading it? (Examples include urgency to act, grateful for your help, relieved, etc)

3) Desired Result: What is the targeted advance? (Will this help me get to a further stage such as green light from the decision maker or help towards another important step in the process?)

4) Anticipating the Response: What is the next desired step to take after sending this email? Can I preempt any objections with this email? What are the red flags or FUDs (fear, uncertainty, doubts) that I hope to uncover with this email and can I ask directly to uncover them or find a way to address it in the next meeting? (Examples: who will be in the meeting? What is the agenda and can I prepare ahead of time to set the agenda of the call/meeting)

5) Timing and Brevity: When do I want to send this email? Is there a better or more opportune time? Is the email phrased in the most concise way possible while still hitting all the goals above?

Startups & Fear

December 15, 2014 in Start Something

To the critic, startup is a noun. To the entrepreneur, startup is a verb.

This piece of wisdom is adapted from a recent book that I read (which I really enjoyed and highly recommend), called Art & Fear – compliments of a Hacker News thread on best books in 2014. The book is one of the most comprehensive descriptions of what it takes to create art and understanding the artists’ emotional journey. It speaks volumes on how to achieve anything difficult, (whether it is sports, tech, art, business), and I found it highly applicable to the journey that entrepreneurs face.

My personal interpretation is that whenever you hear someone critiquing a startup idea, they are observing the idea as a finished product whereas most successful entrepreneurs view their product as a work in progress, something which they constantly look to improve on a daily basis. What matters is whether or not they are getting better at the process.  In short, I think the metaphor rings true, a startup in the eyes of an entrepreneur, is an active verb and never a concrete noun.

Thiel Lectures

September 10, 2014 in By Innovation Only

Lots of things going on at Skillz and I’ll be back shortly. In the meantime, I highly suggest that you read Peter Thiel’s lectures (now turned into a book!) I reread them over the weekend and they have always provided much insight + inspiration.

Tech Isn’t Enough

July 15, 2014 in By Innovation Only

A useful reminder:

“It’s in Apple’s DNA that technology alone is not enough. It’s technology, married with liberal arts, married with the humanities, that yields us the result that makes our heart sing.” – Steve Jobs

The Only Sales Book Startup Founders Should Read

July 13, 2014 in Start Something

It should come as no surprise to anyone that sales is an integral part of a young company’s biggest needs. Getting the first few deals is one of the biggest morale boosts for the team and even greater confirmation that you’ve achieved product-market fit with paying customers.

When building a company, you’ll inevitably get to the point when you have to construct a partnership or business development opportunity that does not rely on a quick one-off transaction at a low price point. The most commonly used word for this is the complex sale. (I’ve also heard it called the consultative sale). The reason this type of sale is differentiated from other types is because you’re usually dealing with higher spends with multiple decision makers, where post-sale support is just as important as getting the deal done.

Examples of this could include any type of B2B sale, an advertising deal with a third-party traffic source, a referral/affiliate revenue share, a licensing deal, etc.

Aspiring technologists/entrepreneurs should embrace these types of deals but information on how to excel at doing them is sparse. The best book that I have found on this subject is called SPIN Selling. Don’t let the title put you off as the word SPIN is merely used as an acronym to help you remember the methodology.

  • The book’s core idea is that complex sales are done not by selling or pushing your product in someone’s face but instead, asking questions and uncovering implicit/explicit needs.
  • The difference between implicit needs and explicit needs are that implicit needs are the implications of a result of a problem and challenge. A rough example, having a car that is 10-years old and having it break down every 5 drives is a problem. The implicit need is the desire to have a car that doesn’t break down. The explicit need is a verbal commitment to do something about this. To get from implicit -> explicit need, what you need to do is do a better job of investigating and asking what Rackham calls SPIN questions.
  • SPIN stands for Situation, Problem, Implication, Need-Payoff.
  • Situation Question: What type of call logging software do you run here?
  • Problem Question: How do you keep track of all your customer’s phone calls between 20 offices?
  • Implication Question: How many dropped customer calls did you have this year? How did the 20 offices deal with this? When something went down, how long did it take to fix? (in days, dollars, etc)
  • Need-Payoff: To deal with the thousands of dropped calls and X dollars in foregone revenue/year, would it be helpful if you had a service that has 24/7 uptime and synchronized call logging/sharing? In what other ways could this help you?
  • By asking these types of questions, you are much more likely to get a deal done and in a way that benefits your customer’s problems.
  • A few other gems:
  • Building rapport is not as useful for complex sales as you probably think.
  • Whether you ask open-ended or closed-ended questions (aka Yes-No questions) matter less, it’s to what end the question is being asked and whether they fit the SPIN framework.
  • There is no set order which you should ask these questions but planning the call ahead of time with these types of questions has been tested time and time again to get results.

Perhaps the main reason that I like this book is that it reframes the concept of selling, specifically as it pertains to closing. Closing is an overemphasized term that is misused in complex sales, as the author rightly points out, because what you are doing isn’t closing on a deal. In actuality, you are opening a relationship with another company. I find that when I adopt this mindset, transparency and accountability come part and parcel, aligning both parties for long-term success.

Last word: Building awesome tech is hard, but bringing it to market is just as tough. A book like this one helps bridge the gap.

Creating Knowledge

May 11, 2014 in By Innovation Only

“Centuries ago, the critical constraining resource was land. Those who controlled the land controlled everything. At some point, the constraint became skills, and guilds and merchants created more wealth than did landowners. Later, the industrial revolution moved the constraint to capital, and power became financially driven. Today, the constraint is knowledge: technical knowledge, management knowledge, process knowledge, and market knowledge. Much of this knowledge is (now) being expressed as software.”

Source: “Implementing Lean Software Development” (M. and T. Poppendick)

Resume Faux Pas: Your Objective vs. the Company’s Objective

April 8, 2014 in Work Smarter

For job seekers, your resume is make or break. It’s the first point of contact with a hiring manager, regardless of company size. When I see a friend or potential applicant make use of the Objective sentence in their resume, I feel the slightest cringe when it is structured along the lines of…

Objective: “Seeking a challenging position leveraging analytics skills that will enhance my leadership skills and technical background.”

I’ve definitely written Objective statements like this before.

The question you have to ask yourself is this: What is your objective from the POV of a potential employer? A hiring manager reading this is usually thinking just one thing: WIIFM (What’s in it for me?)

They would be more inclined to move you forward if your objective was positioned from the company’s perspective as opposed to your own.

Some alternatives that could work:

“To share my experience of sales and marketing analytics to help a fast-growing tech startup to better understand their customers, developing best in-class dashboards and reports, and training future hires to do the same.”

“Seeking a position that allows me to directly increase the lifetime value of existing customers at X through my analytics, engineering and client-facing business background.”

By taking this approach, your resume shares how you plan on actually creating value, while giving the hiring manager ammo/talking points for championing you.

Imagine him or her saying, “Take a look at Jeremy, he’s the one who wants to help our company improve our reporting and mobile app tracking. He’s got a bachelors in engineering and was also previously a consultant. Let’s have a chat with him next week.”

Yes, one could just include this in the cover letter, but I recommend putting it in the resume. Cover letters have a tricky little tendency of getting lost.

So He Put In More Windows…

April 1, 2014 in Work Smarter

Coach K on Lebron James:

“The game is a house, and some players only have one or two windows in their house because they can’t absorb any more light. When I met LeBron, he only had a few windows, but then he learned how beautiful the game can be, so he put more windows in. Now he sees the damn game so well, it’s like he lives in a glass building. He has entered a state of mastery. (Source)

Great analogy for early stage companies and picking up different skill-sets whether it is marketing, engineering, product, sales, etc.

Some places to learn “how beautiful the game can be”…


Now for a little “Get Real”:

“I’ve looked up every company that did an IPO in the U.S. since 2000. Even the best-known employers of knowledge workers often have fewer people than a local car dealer or Walmart store. For instance, real estate site Zillow has 812 employees, and travel site Kayak has only 205.”

(Harvard Business Review - Why Do App Developers Still Live with Their Moms?)

What I’m Reading

March 1, 2014 in Prevent Boredom

Met the guys at Hashicorp and I’ve been playing and dabbling around with Vagrant for a few weeks. Awesome tools for getting a run-time environment right out of the box and for the design-centric folk, being able to focus on testing designs without worrying about the nitty gritty.


Eloquent Ruby - Lots of programming language books have a lot of information. This one contains knowledge.

Running Hadoop on Mesos


Young Money: Inside the Hidden World of Wall Street’s Post-Crash Recruits

I’ve read a few of Kevin Roose’ s articles in the New York Magazine and wanted to check out his latest book. Interesting cross-profiles of young people and how they are faring after the recession in the field of high finance.

“Doing thousands of little things, day after day, inching along as consistently as you can, in the right direction, as best as you can tell, is management  - and motivating or inspiring everyone to work together for long-term purpose is leadership.” (The Partnership)

“History is a tale, Franklin came to believe, not of immutable forces but of human endeavors.” (Benjamin Franklin – An American Life)

“This means answering the most testing question of all. What will keep the scintillating twenty-three year old engineers in the world’s greatest colleges and universities yearning to hear word that they have been offered a job at the company formerly known as Apple Computer, Inc.?” (Return to the Little Kingdom: Steve Jobs and the Creation of Apple)

“Business development is not a science but it does operate by a logic that is subject to analysis.” The more people you know, the more opportunities you get. (Creating Rainmakers)

The Beginning of Infinity: Explanations That Transform the World

Weekend Inspiration

February 22, 2014 in Start Something, Travel the World