Email best practices


I’ve been using email since 1980. At the time I was taught two things about using email: one, don’t put anything in email that you wouldn’t want to see on the front page of The New York Times (unfortunately innumerable people haven’t followed this best practice), and two, respond in no more than 24 hours – if only to acknowledge that you received the email.

I’ve tried to pass these best practices, and a few others, such as how to title email attachments, to my teams.

So I was pleased to see that I’m not only executive who believes in being responsive to emails. Here’s the snippet from The Wall Street Journal article How Take-Two’s CEO Powered Up, sub-titled Strauss Zelnick sought advice from a series of high-profile mentors in his quest to conquer the worlds of media, entertainment and videogames.

Mr. Zelnick says he has adopted a number of best practices from Barry Diller, Chairman of IAC/InterActiveOne example: “Respond to everyone, always within 24 hours,” Mr. Zelnick says. “It’s courteous and you never know where opportunities are going to come from.”

Mr. Diller was probably speaking not just of email, but of phone calls, faxes (!), and other forms of business communications as well.

A ringside seat at company naming trends


Crunchbase is a very valuable database of new companies and the people behind them. As such it has a ringside seat at trends in naming startups. I’m not the only person fascinated by the process of naming new companies. Sherwin Greenblatt, President of the MIT Venture Mentoring Service, presents a list of VMS companies who have changed their names at every monthly mentors meeting. And he admits it’s one of his favorite part of the meeting.

While you won’t find an entire category on my Mentorphile blog devoted to posts about company names you’ll find a few posts, including what I consider the best article on how to name a company that I’ve yet seen. But company names, like many elements in the startup ecosystem, are always changing, so the article by Joanna Glasner on Crunchbase News, Startup Names May Have Passed Peak Weirdness, is well worth reading if you are in the process of naming, or renaming your startup.

I remember being very puzzled as a kid by product names like Kleenex and Trix – these words weren’t spelled right! Only years later did I learn that the best way to trademark a product was by making up a word, like Kleenex, or changing the spelling of an existing English word, like tricks.

An then years later, with the advent of the world wide web and the gold rush for .com domains, did I see a tsunami of new company names.

Ms. Glasner’s article does a good job of listing the major ways that companies generate their names, and what’ going on within each category.

According to Athol Foden, president of Brighter Naming, a naming consultancy, founders are getting less comfortable with weird names.

Crunchbase News does an annual survey of startup naming trends. The latest trend is for startups to choose simple words to describe their businesses including companies like Hitch, an app for long-distance car rides, Duffel, a trip-booking startup named after the popular travel bag, and Coder, a software development platform. However, there’s a problem with having an overly descriptive name for your company – what happens when you pivot? This can happen to even large established companies. Apple Computer, Inc. had to drop the “Computer” when computers became a small portion of their product line compared to the iPhone. And iTunes has become a catchall for music, movies, TV, and software used to sync your iPhone with your Mac. What I like are names that are evocative, like Amazon – the largest river in the world, not descriptive. With descriptive names, one pivot and all that brand equity can disappear as your descriptive name becomes obsolete. When “fried” became a bad ting for you diet Kentucky Friend Chicken was forced to change their name to KFC.

Creative Misspellings

One of the most wide-spread, and frankly easiest way to create a unique name is to purposefully misspell a common word, like Flickr, the early photo-sharing site.

However, creative misspellings are getting less popular, Foden said. Early-stage founders are turned off by the prospect of having to spell out their names to people unfamiliar with the brand (which for seed-stage companies includes pretty much everyone).


It seems like only a few companies with pun names have gone public or been acquired, according to CrunchBase. Both Foden and Glasner are in favor of seeing more Internet startups with pub-based names. I’m afraid I can’t agree, as I find that often people just don’t get puns. And then when they do, they can be irritated at the cuteness of the pun. My original name for the company that became Course Technology, Inc. was Of Course, Inc. But the straitlaced VCs at Greylock hated that name and told me in no uncertain terms that “No company with a cute name would ever go public.: Of course, that was before the days of Yahoo, Google, et al!

Made-Up Words That Sound Real

If you are clever enough to pull this off it can be a real win, as not only will you be able to snag a valued .com domain, but you will also be able to trademark your name. Names like Invocable and  Locomation are good examples.

Normal-Sounding Names

In the industrial age companies had boring and obvious names like Standard Oil, U.S. Steel, General Electric and International Business Machines.  But the problem with the latter two, and many others, is that their names quickly became shortened to just their initials: GE and IBM, not to speak of AT and T. Know what that stands for?

Compound Names

There’s a major category that Ms. Glassner leaves out of her article, the category that probably works best now that virtually every word in the English language has either ben taken by a startup or by a domain squatter. That category is the compound name. Two of the best known examples being Facebook and Microsoft . The approach is to concatenate two short words, like Bitpipe. I’m sure any good coder could whip a program to auto-generate compound names. In fact domain squatters probably have. But even so, this is a proven way to generate an easy to spell, easy to pronounce company name.

Gud lukk!

The name game – naming is changing

Midsection Of Woman Holding Name Tag With Text

One of the biggest challenges for startups has been and still is coming up with a name for the venture. Decades ago, when I began my startup ventures with Real Time Audio, which I thought was a great name for a sound reinforcement company, one didn’t have to worry about urls. In fact I was so naive at the time I didn’t even worry about trademarks!

But today’s founders have a lot to worry about when it comes to naming and I have several posts on Mentorphile on the subject.

Sherwin Greenblatt, the head of MIT’s Venture Mentoring Service, always enjoys the monthly meeting time slot when he announces the name changes of VMS ventures. It’s a favorite of mine as well. Sometimes the changes are for the better, other times we collectively scratch are heads and wonder if the new name is actually worse! There’s always a few laughs mixed with groans at the oddball names.

The good news is that according to Joanna Glasner‘s article on TechCrunch Startup names may have passed peak weirdness. She quotes Athol Foden,  president of Brighter Naming, a naming consultancy: “As we reach the edge of strangeness… they’re saying: ‘It’s too weird. I’m uncomfortable.”

Crunch News does an annual survey of startup naming trends (news to me!) and the trend is that startups are choosing simple words that describe their business, including companies like Hitch, an app for long-distance car rides; Duffel, a trip-booking startup named after the popular travel bag; and Coder, a software development platform.

Joanna Glassner lists the common ways founders generate unique names:

  • Creative misspellings
  • Puns
  • Made-up words that sound real
  • Normal-sounding names

For some time now my advice to startups is that if they have some capital to invest they should simply buy a name that meets the common naming rules, that will save them much time, effort, and anguish. And domain squatters have plenty of names to sell. If you can’t afford to buy a name, one method that works for many companies is compounding two simple words; the best example being “face” and “book.”

While it’s true that your name is your brand and .com is the most highly valued domain, both are shifting. Companies change their names or create new parent companies like Snap for SnapChat or Alphabet for Google and other ventures. And even Alphabet eschews the .com domain, Alphabet’s url is

One of my current mentees is in the midst of name change – I’m looking on, hoping they can improve on their current name, which doesn’t seem hard to do, but it is!


The value of diagrams

data flow

I’ve posted previously about the value of diagrams in presenting your business. In fact by creating some of these diagrams you will also better understand your business.

In discussing the value of diagrams for founders with MIT VMS mentor Beth Kahn she mentioned that she had a number of types of diagrams she would share with me and the mentee. Thanks to her for providing a full deck of diagrams, of which I’m just going to present a few.

Process diagrams are useful in three ways:

  • Information: how decisions get made
  • Activities: who takes action
  • Products: how the product is delivered
  • Money: the flow of funds

There are three types of process maps:

  • Ecosystem: who are the stakeholders
  • Workflow: how your product is built or your service is delivered
  • Value chain: how value is added during the product lifecycle

I generally ask founders to first map their ecosystem: who are the suppliers? competitors? sales channels? value-added resellers? service providers? substitutes for your product? analysts who track your market segment?

Here’s an example of the ecosystem of the stakeholders in a company called LimeFinder.


Here’s the value chain for an electric car:

value chain electric cars

Here’s the work flow diagram for LifeFinder:

workflow Limefinder

There is one other diagram I will share with you that outlines the customer discovery process, which should be the starting point for founders:

customer discover

Once you actually have a product and are selling it you need to understand who are the players in the sales process:

  • Decision maker – makes the final decision to purchase
  • Influencer – can sway the decision maker but is not the decision maker
  • Economic buyer – issues the PO or signs the check – not necessarily a user of the product
  • End user – the actual end user of your product or service
  • Early evangelist or product champion – an early adopter who advocates for your offering
  • Saboteur – someone who seeks to undermine the adoption of your product due to real or perceived negative impact of your offering – you may be seen as a competitor

These are the major types of diagrams that are useful for both learning about your processes and presenting them to interested parties, such as investors or candidates for hire.

If a picture is worth a thousand words, in business I would say a diagram is worth ten thousand words. Yes, they are a lot more work that just snapping a photo with your smart phone, but the work that goes into them with have real value in proportion to the time you invest in developing and modifying these diagrams for your business.

What’s the highest bandwidth communication medium?

nyt reporter

My introduction to email came in 1980 when I joined Software Arts, the inventors of VisiCalc, the first electronic spreadsheet. We all had VT100 terminals on our desks that were tied into a Prime minicomputer. The Prime was used for software development as well as for our internal email system. I quickly became a heavy user of email, as was everyone else in the company. We had a connection to the ArpaNet, the precursor to the Internet, and I could have sent email to scientists and researchers around the country, who were the only users of ArpaNet, but I didn’t know any of them!

Email has a lot of advantages, but for me it had several specific ones:

  • It enabled me to communicate asynchronously with everyone in our company as well as with our distributor Personal Software, located two time zones away. Trying to get people together for a meeting wasn’t easy and often was totally unnecessary. Email worked well as a one-to-one and one-to-many communications medium.
  • I hate making phone calls. People’s voices didn’t sound quite right, as the phone company restricts the bandwidth of the telecom system in order to increase capacity. And you never know if someone is paying attention or not while talking to you. I could go on but everyone is familiar with the hassles of phone tag and the annoyance of voicemail
  • It served as a record of my work and a to do list. Email wasn’t designed to do either, but by putting most work related communications into a written form I could keep track of what people “owed” me and vice versa.
  • It allowed me to work from home and feed my work addiction by enabling me to send and read emails every hour of the day or night.

Even today with Facebook Messenger, WhatsApp, Signal, and dozens of competitors to plain old email, I’m still a heavy user. But neither email, nor phone calls, is a high bandwidth communications channel. Face-to-face or F2F is by far the highest bandwidth channel. I was reminded of this today when reading the New York Times article Digital Privacy Is a Big Concern in Europe. For This Reporter, Too, subtitled When the investigative journalist Matt Apuzzo moved from Washington to Brussels, he noticed that distrust had a different focus. And he adjusted some of his own tech tools. This story is part of a series that The New York Times runs about how journalists use technology in their jobs and in their personal lives. I read three newspapers every day: The Times, The Wall Street Journal, and The Boston Globe. I have great respect and admiration for journalists. But beyond that I believe that mentors need to act like investigative journalists themselves. We need to find out what’s the story behind a founder’s presentation. Asking the right questions at the right time is one of the core skills of both journalists and mentors. And, of course, communicating with our mentees outside of our F2F meetings is important.

What are the most important tech tools for you as an investigative journalist?

Tech is great, but there’s no substitute for personal relationships. I prefer face-to-face conversations whenever possible, and I almost never record them. I use small, discreet notebooks like the Moleskine pocket journal. A lot of my interviews are over coffee, drinks or meals, and I want something as unobtrusive as possible at the table. I love the feel of the Rhodia pocket webnotebook, but let’s be honest: I’m not picky. Some of the best, most surprising nuggets of information have been scribbled on napkins or the backs of envelopes or tapped in text messages to myself.

Face to face communications is considered so important by the MIT Venture Mentoring Service that VMS does not support remote mentoring of any kind.  Aside from occasionally accommodating mentors who may be traveling or otherwise not able to come in to MIT by using a speaker phone, the emphasis is always in meeting founders F2F and in teams of mentors. Why is face to face so powerful in this technology mediated age? For one thing we all have grown up talking to those around us. We had to learn how to use the telephone and then the computer and smartphone. But F2F also provides a much broader field of view than typical video conferencing tools. Facebooks’ new Portal uses AI to move it’s camera to follow the person talking. While I haven’t tried this, I’m sure it’s an improvement on Skype or Zoom. But sometimes when meeting with a team of founders I like to look at the members of the team who aren’t speaking. As a mentor you can learn a lot about team dynamics by watching the team while one of them is talking. Are they paying attention? Are they leaning in, which demonstrates interest, or leaning back which demonstrates disengagement or even boredom? Do they have their arms crossed, which often signals anger or disagreement? Are they looking at their phone rather than at the people in the meeting? These are important questions which are impossible or hard to answer during a phone call or video conference.

Humor is important in all human relations, but even more so for founders, who are often very stressed out by the rigors of startup life. I find it’s a lot easier to crack a joke during an inn-person meeting than over the phone. And most of us know that email is the worst medium for humor. Without the nuances of vocal tone and inflection and non-verbal communications, humor often falls flat, or worse yet, can be misinterpreted and even come across as offensive.

I also find it’s a lot easier to start off a meeting with non-business chat, which helps build personal relationships amongst mentor teams and with founders, than using a video call. Perhaps it’s because none of us have grown up with video calling, but we seem to see it as a more formal and constrained medium. Perhaps millennials and Generation Z  don’t have this issue.

For me the goal of a mentor meeting is conversation, not presentation. So I don’t encourage founders to start off meetings with their decks. Conversations help build trust, which is vital in a mentor-mentee relationship. And I often coach founders to treat sales calls as conversations, dialogs, not monologs nor presentations. We learn a lot by listening; we learn little while talking.

Of course there are drawback to any medium and F2F is no exception. People can talk over each other, they can mumble, they can pontificate, they can wander off the subject. Having an agenda, objectives, and structuring the meeting can help avoid these problems.

And speaking of problems, I learned the hard way that problems need to be solved face to face. While it’s far easier and faster to send an email doing so can make a problem worse, not better. If the person you need to communicate with is out of town then pick up the phone, even if making phone calls seems foreign to you. Problem solving needs real time communications, and though text messaging is real time it is a sparse medium unlike the rich medium of face to face meetings.

So when you need to communicate, choose your channel wisely. But keep in mind Times reporter Matt Apuzzo’s words: Tech is great, but there’s no substitute  for personal relationships.


“Mentor” now chasing “Innovative” as most used and misused business term



I was dismayed by the use of the word “mentor”  in the Business Insider article by Rosalie Chan Larry Ellison says that Oracle was once a week away from not being able to pay employees — here’s the lesson he learned from the experience.

Ellison hosts a cocktail reception to mentor startup founders each year. Last week, he hosted the founders of 22 startups at his San Francisco home — and eWeek was in attendance to report on the advice he gave.

First of all it is impossible to mentor 22 people at once! Second and perhaps less obviously, mentoring is not a one-time thing, it’s relationship between the founder and the mentor that can last months or even years. Larry may well be advising 22 startup founders and perhaps he mentors a handful of them – the article doesn’t say. But mentor is starting to get overused just as the words innovate and innovation have before it. This blog devotes an entire category to mentoring.

However, the article does include two good lessons learned by Larry Ellison when Oracle was a startup, not the behemoth it is today, 40 years later.

First, is to balance doing whatever it takes to pay the bills with whatever it is that you actually want to do. One of my newest mentees is struggling over earning money from a first client, but a client that’s a real outlier on the distribution of target clients. The number one need in all startup is cash. Even if you are sharing an apartment with six other engineers and living on ramen noodles you still need cash. So I totally agree with Larry’s advice – do whatever you need to do to earn cash even if it’s NRE – non-recurring engineering. 

Second, once your startup crosses the chasm and becomes an on-going concern you can’t get complacent. As Ellison says:

The old solution to customers’ problems may no longer be the best solution. When you see that, it’s an opportunity—or a threat,” Ellison said, according to eWeek. “It’s our job as founders and developers to constantly change our companies based on technology available today that wasn’t available yesterday.

And like every other company, Oracle is realizing that AI is not just a science experiment any longer, Oracle has been focusing on its autonomous, AI-powered database and its cloud solution.

As a mentor I hope that the it remains a term of art, unlike innovative, too often used and misused as in “new, innovative” which is redundant, as the very definition of innovate includes the word new.

innovative |ˈinəˌvādiv| adjective(of a product, idea, etc.) featuring new methods; advanced and originalinnovative designs | innovative ways to help unemployed people.(of a person) introducing new ideas; original and creative in thinking: an innovative thinker.

Well I’ve hit my pedantry quota for the day!



What’s your product narrative?


I’ve posted previously how at Amazon developers’ first step in new product development is to write a press release about the product they plan to create. But Scott Belsky in his new book The Messy Middle takes narrative well beyond the press release.

Carmine Gallo, one of my favorite business writers, writes about Belsky’s book in the Forbes article An Early Uber Investor Reveals A Creative Strategy To Build An Irresistible Brand. His key take-away from the book is that founders should build their narrative before they start developing their product.

According to Belsky, “Most entrepreneurs jump in and build a product. They’ll spend months, even years, building an MVP (minimal viable product). Right when they’re about to share it with the world, they realize it doesn’t resonate with consumers. People don’t understand why it helps them and why they should use it instead of something else.” Belsky recommends that entrepreneurs avoid this problem by starting with a story before the product is built—paint a picture of what the world will look like when the product is finished.

Belsy recommends that developers build a private web page for the product that should answer the following questions:

·     What inspired the idea?

·     Why does it need to exist?

·     Why is it relevant?

·     How does it make the future better?

The narrative services not only as the roadmap to how you develop your product but how you will market it as well. All stakeholders, from investors, team, or partners are helped to visualize the future.

Being able to recite a narrative—tell a story—about a future customer and how the product will solve a real-world problem is a powerful exercise that few leaders do in the early stages of the development process. “It’s very powerful and most teams don’t spend a lot of time on it,” says Belsky.

It’s a truism that investor pitches need to tell a story, but Belsky’s concept of the narrative goes beyond that to acting as the lodestar during the entire lifecycle of the product.  I see Belsky’s approach as similar to what I recommend to founders, using the journalists who? what? why? why” where? and how? to tell their products story. But what is different about Belsky’s approach is that it helps everyone envision the future. He gives a great example, how Garrett Camp, co-founder of Uber imagined a future where where everyone could call up a private driver, something only reserved for wealthy elites at the time. He imagined it as a superpower that ordinary people would have at their fingertips, literally. The story evolved into Uber’s first tagline: Uber is everyone’s private driver. Journalists report on the present; you narrative is a report from the future!

This also ties in with how Alan Kay recommends founders develop their products which I wrote about in the blog post How to invent the future. Belsky’s put his money where his book is, he was an early investor in Uber, in addition to founding Behance, an online portfolio company for creatives that he later sold to Adobe for an estimated $150 million. Today, Belsky is Adobe’s chief product officer and a venture capital investor.

He uses as an example Garrett Camp. the cofounder of Uber. (Belsky was an early investor in the company) Before Uber was a product—or a company—Camp was working on the narrative. Camp began to imagine an experience where everyone could call up a private driver, something only reserved for wealthy elites at the time. He imagined it as a superpower that ordinary people would have at their fingertips, literally. The story evolved into Uber’s first tagline: Uber is everyone’s private driver.

To recap, while Jeff Bezos’s practice of writing a press release for a new product that has yet to even begin development acts as a guiding light, a narrative envisions the future how the product will change life for consumers. Both approaches will not only guide developers but help them communicate the nature and value of their product to all stakeholders from investors to users.

How to manage information overload



There’s a plethora of advice out on the web for founders, not to mention magazine articles, newspaper articles, videos, and books. How do you deal with it all? There isn’t enough time in your day, let alone your lifetime, to read all the blog posts and articles offering advice to startups, including this one. Here are some ways you can manage information overload:

  • As your friends, colleagues and mentors who they follow on Twitter, whose blogs they subscribe to, and what sources they have found most helpful. Build up a list of trusted sources you can rely on to make the time you spend with them a worthwhile investment.
  • Brand names matter! The New York Times business section and The Wall Street Journal both feature stories about startups or technology virtually every day. Subscriptions to these newspapers are expensive. If you can’t afford them here’s a trick: do a Google search on the article you want to read that is mostly blocked behind a pay wall. Often you’ll get access to the full article. And , of course, see if any friends or colleagues subscribe. Forbes is a another great source of advice on startups. And every public library has subscriptions to these newspapers as well as business magazine like Forbes, Bloomberg Business Week, and Fortune.
  • Take note of authors; There are several authors, like Nick Bilton, who I can rely on to write a helpful article. Often authors provide a link to their bio from their byline. You may even find their email there or even at the end of articles they have written. If you have a media relations program start building a list of writers to contact.
  • Use a news aggregator: The news aggregator I’ve been using since it first launched is Flipboard, not only is it free but it’s available on PCs, tablets, and smartphones – at least of the Apple variety, which I is what I use. Flipboard enables you to customize what amounts to an online magazine, based on your interests or publications you want to follow. It’s also beautifully designed. Unfortunately since it’s ad supported it has to drive eyeballs so there are many more listicles featured than when they first launched. But if you only have time for one “publication” make that Flipboard.
  • Learn to scan and skim. Professional writers are taught to use the inverted pyramid for their articles. That means that the most important information will be at the beginning of the article and the level of importance decreases as your read the article, until you hit rock bottom. Journalists are also taught to use what is called the topic sentence. The topic sentence is usually the first sentence in a paragraph and it summarizes the main idea of the paragraph. If you don’t have time to read a full article you can skim by reading only the first paragraph and the topic sentences of succeeding paragraphs. You can also scan the article for keywords. But much more effective is to use article search: Command F on the Macintosh. Using article search I can quickly find every mention of keywords that are important to me, like mentor, as each occurrence is highlighted in yellow.
  • Use the Reading List feature of your browser. I often come across articles on the web that I don’t have time to read, but I can save them for later by adding them to the Reading List feature of my browser, which is Safari on my iPad and iPhone, where I do most of my reading. Alternatively, if you use Evernote, as I’ve been doing for years, you can save any article to a notebook on Evernote. I often copy a salient paragraph and add it to the note – that helps me remember why I saved it in the first place – not always obvious!
  • Make use of dead time. We all spend lots of time waiting in lines or sitting in waiting rooms. Make sure you have a backlog of articles in Evernote or your browser’s reading list and take advantage of dead time to scan and skim an article or two. Make productive use of dead time!
  • Limit notifications. Virtually every app I use wants to send me notifications. If I said yes to all of them I’d be doing nothing else. Limit your notifications to a very small number, then cut out a few. Getting interrupted is very distracting and can wreak havoc with your productivity.
  • Share the wealth. If you find an article that you think would be important for a friend or colleague send them a link. All browsers have sharing built in, as do most news apps. If you prove to be a trusted source of helpful links your colleagues may reciprocate in kind.


What’s good about email?


email insert.pngAfter bashing email yesterday in my post Email – the app we love to hate! I came across an article on Medium this morning by Aytekin TankHow email can actually enhance your productivity. I’ll post what I think is good about email, adding in any benefits I’ve missed from Mr. Tank’s article. But keep in mind he is the founder of JotForm, which according to its home page enables users to: Create online forms and publish them. Get an email for each response. Collect data. So Mr. Tank may just be slightly biased in favor of email. Nonetheless he begins his article with a quote from UI/UX guru Don Norman‘s quote,  “email is the office memo turned cancerous, extended to home and everyday life.”

So what’s to like about email?

  • It’s asynchronous. I much prefer either meeting face to face or communicating by email. I hate talking on the telephone to a disembodied voice. Real time communications apps like iMessage or Slack do have their uses but I find them to be overly terse and overly used.  Because email is asynchronous I can reply, if at all, on my schedule, not on the sender’s. I can give real thought to composing my response, commensurate with the importance of the message.
  • It’s a good way to keep track of projects. I’m a big user of Apple’s reminders app, but I still find it useful to save emails from colleagues and others that are still relevant to whatever project we are working on.
  • I can attach files – documents or images. This feature has been copied in most real time apps, but it’s still a benefit of email. And I can tell at a glance which emails I’ve sent or received have an attachment. Sometimes it’s the only way I can find a file that’s gone missing!
  • You can communicate one-to-one or one-to-many. Apple and others have made conference calling, either voice or video, much easier. But scheduling a conference call can be more trouble than it’s worth. Emailing everyone with a stake in my message is much more efficient, even if the request is to use a scheduling app to set up a meeting.
  • It improves my writing. I learned business writing by writing three to five press releases a week for over three years. I started using email in 1980 at Software Arts where although there were only about a dozen of us in 1980, email was heavily used by the founders, which, of course, meant that everyone used our in-house email system heavily.
  • It enables me to get feedback in writing. While I do prefer f2f meetings, taking notes is a chore and distracts from fully participating in the meeting. Getting written feedback on a proposal I’m working on is usually more helpful.
  • You can easily copy and paste. It is very easy to send a personalized version of basically the same email to several people. And I often copy a salient extract from a full article I’m sending to someone so they don’t need to read the entire article unless they wish to.
  • Mail forwarding is easy and helpful. And yes, like the cc function it too can be just as easily misused.

Here are to additional benefits from Mr. Tank’s article:

  • It builds trust. I’m not a CEO, but when I was an executive my teams new I expected quick responses to my emails, if only to acknowledge the “ask” and inform me when they could get it done. Likewise, I tried to respond to everyone in the company’s email with a couple of hours unless I was traveling.
  • You don’t forget important details. Mr. Tank points out this as a benefit of cleaning out your inbox daily. And I do agree with this, especially for busy executives with a lot coming at them continuously

In the section of his article, Writing email, Mr. Tank includes one of my global principles: show, don’t tell. He uses screen shots heavily, as well as tables. Adding graphics to an email is almost as easy as adding text and can be far more effective. He also recommends using @tags. That’s a trick this old dog has never learned, perhaps because I’m not a Twitter user, so I can’t comment either way of this tip. Otherwise we closely agree on the principle ways to craft and effective email message.

Mr. Tank ends his article with four tips on how to process your email. I’m not sure I’m in total agreement with these so I’ll leave it to readers who are interested to read that section of his article.

He closes his article with a quote from Slack cofounder Stewart Butterfield that email isn’t going away any time soon. “Maybe by 2080,” he said. “It’s got decades left at least.”

So you might was well get good at composing, sending, and managing it.

Email – the app we love to hate!


Despite the rapid growth of intra-company apps like Slack and business use of text messaging, email remains the primary communications tool in business, both within and between companies.

Everyone complains about email, but it seems that no one does anything about it. However, Adobe’s annual consumer email survey, reported in an article in Mental Floss  provides some hard evidence for what not to do with your email. But fefore we get into the don’ts, let’s list the do’s.

The “To” Field

Autofill has made it easier than ever to send previous recipients email, even if they would have no interest in it. Think long and hard about the following before you fill in the address field or let your email app do it for you:

  • Who really needs to know about your topic? Think about the way secretive organizations like Apple operate – they keep information on a strictly need-to-know basis. While you don’t want to develop a reputation as secretive, people already get way too much email. According to Adobe their survey of 1,000 white collar workers with smartphones found that they spend 3.1 hours a week checking email.
  • Why are you sending it to them? If it’s just to keep your colleagues “in the loop” you may be doing them a favor by not sending it all or moving them to the cc field.
  • What action do you expect? If you aren’t clear what you expect your recipient to do about your email how can they be? And if you send the email to more than one person it can be fuzzy about which person is expected to do what. If there’s not action expected, go back to point number two – why would they want to know about your topic?
  • If action is expected when do you expect it? Everyone is busy. If you don’t attach a deadline to your expected action, even if it’s just “get back to me by next Monday or I’ll assume it’s ok.” your to do will slip to the  bottom of their list, if not off it entirely. Redundancy helps avoid confusion. Rather than just saying “next Monday” use “next Monday, the 25th.” And notice the use of the default above? A default is the action that will take place unless the user intervenes. Defaults are very powerful in computer interaction design, as they reduce the decision making load on users. Defaults can provide the same benefit in emails.
  • Why are you sending it? Unless you are replying to an email, you need to make the reason for sending it clear from the get-go. See “The Subject line” below. If your reason is too complex to fit a subject reline you may need to rethink it. Again, though, redundancy can help, so it doesn’t hurt to restate the reason in the first line of the email less tersely than in the subject line.

The “cc” field

  • The over use of the cc field is probably the biggest problem with interoffice email. It’s so easy to add people “who just might need to know” or “just might feel slighted if I don’t include them.” Well if you develop a reputation for just emailing people who really need to know and don’t bother everyone else that will soon become a positive in your online reputation.
  • Be careful about cc’ing superiors. Think long and hard before you cc your recipient’s manager or other senior official. There are at least two bad outcomes: one, your recipient may feel like you are covering your ass by copying their boss and two, the senior person may think the same of you. Neither are good for your virtual reputation. Keep that “need to know” principle in mind. Experienced emailers who get involved in referral threads wisely say something like “moving you to cc” to me when I’ve done my job of introducing two acquaintances. Then I know I’ll soon be dropped from an email conversation I know longer need to take part in.

The “bcc” field

I never use this field. I don’t like the idea of hiding a recipient from the person I’ve directed the email to. I can imagine if you are in corporate HR or have some other internal political reason to use this – but I’m not. If you aren’t either, then don’t use it. And if you use it infrequently you may actually forget if you cc’d or bcc’d someone, which could get embarrassing in a team meeting.

The Subject field

  • Anyone who gets a lot of email – and who doesn’t? – learns to scan subject lines. After the importance of the sender – and most email packages enable you to set up a VIP list to highlight email from important people, use it – the subject line is next. Lack of clarity in subject lines is one of the biggest issues I deal with. My guess is that people just don’t give enough thought to the subject in their rush to write the actual email. But treat the subject line like a text message – it needs to stand alone and convey useful information.
  • Keep it short! Overly long subject lines may get truncated or wrap awkwardly depending on the recipients device and email app. And shorter subject lines are more likely to be read.
  • As a test bring up your own email and view just the subject lines. How many are helpful? How many are too long? Or even too short? By reviewing both the emails you receive and the ones you send you can keep tabs on how well you (and others) are making use of the Subject line.

The From field

This one seems like a no-brainer, right? But for those of us with multiple email accounts it isn’t. If your default account is your work account you don’t want to use it for personal email. And if for some reason your email defaults to your home email address, make sure you change the From field in business communications. Which brings up a pet peeve of mine: people who share email addresses with their spouse. I have no idea why they do this, or worse yet, why they use these email addresses for business, but you’d be surprised by the number of freelancers or entrepreneurs who do this. One word for this practice: Don’t!

The message

Ok, we are finally at the whole point of sending your email – seems like a lot of work to get here, but trust me it will pay off. Some simple rules for your message:

  • Be consistent in how you address recipients. If you know them, then a “Hi, Bob” is fine, though some people prefer you don’t bother with a salutation and just get to the point. For someone you don’t know you’ll want to give more consideration to the salutation and potentially be more formal, as in “Hello, Mr. Jones:”
  • Keep it short, simple, and to the point.
  • Keep separate topics or points in separate paragraphs. This makes it far easier for the recipient to read or scan.
  • Don’t mix personal with business in the same message.
  • End with an action item, even if all you want is an acknowledgement.

The major takeaway from the Adobe survey was that 25% of email recipients were enraged by getting emails  with phrases like “Not sure if you saw my last email”, “per my last email,” “per our conversation,” and “any update on this?”  It seems clear that people resent follow up emails. If someone hasn’t responded to your email there’s probably a good reason – they aren’t interested or are too busy. Sending them yet another email won’t help in either case.

The other tip from the survey is to eliminate tentative filler language like “no worries if not” from work emails. If you want to get ahead, it’s better to be assertive, clear, and direct in your emails, not passive aggressive and wishy-washy.

One final tip – replying to email

Don’t use a previous email to start a whole new topic with your recipient. Not only can this be confusing, your recipient may skip your email if they see it as a reply that they have already dealt with. If you have a new topic to email about, start a new email! They are cheap and it will keep your recipients email inbox more organized, along with your sent email box. The latter is important, if like me, you sometimes use the sent box to keep track of where you are in a project with another group.

To recap: email is dangerously easy to use, and thus to use sloppily. Keep in mind you intent in sending your email. Remember that how you handle email will make up an important part of your online reputation. Needlessly cc’ing your colleagues manager or worse yet, the manager of someone you are trying to sell to, can be self-defeating in the short run and harmful to your reputation in the long run.

We are stuck with email for the foreseeable future. So learn to use it sparingly and appropriately, just as you would with any other form of communication.


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