How to, and How NOT to Communicate with a Business Contact in 2016

“What a strange title. This guy is going to teach me how to do something I’ve been doing my whole life?”

Yes. And you are going to disagree with many of my points thinking they don’t apply to you. If you are not a fan of differing opinions, we can part now as friends.

The truth is, like many of my posts, this will most likely end up being more like a rant than a blog post. The reason for that is because the idea for this post came to me after getting one too many phone calls from some random person asking me for help of some kind. A phone call. Not an email. Not a FB message. Not a tweet. Not a snap. A phone call. In the middle of the day. With no prior warning or request for a call. No calendar event. No previous discussion.

Slow down, Hillel. Pace yourself.

Here’s me laying out the topics I want to cover when it comes to business communication in 2016. But before that, this does NOT apply to family, close friends, or, as my father pointed out to me, pretty much anyone over 60. This isn’t a good thing or a bad thing. Not judging anyone. Just saying, apparently my parents and their acquaintances communicate differently than I do. When I expressed my frustration about getting a phone call to my father, he looked at me like I fell off of Mars.

Ok, now that we got that out of the way, the topics. Email. I want to talk about email. I want to talk about how to increase the chances of receiving a response to your email ask. I want to talk about email etiquette and what never, under any circumstances, to do.

The phone. As in that thing that rings. I want to talk about who it is ok to call.  When. How. What to do prior to that call. And how to increase the chances of making it an effective call. By the way, FB/Whatsapp calls, are they more like calls or more like messages? We’ll cover that too.

Then I want to cover messaging apps. Again, how to use them. When to use them. How to increase the chances of getting what you want out of that message. And of course, what NEVER to do in a messenger app.

Pretty sure there will be more topics covered in this post but those are the basics. Email, phone, messaging apps. So let’s begin, shall we?


As of now, and this might very well change, email is still the default communication tool for business. So many have tried to change that, including my own previous startup, Zula, and failed. Yes, I know Slack is wildly popular. Email is still the default.

What that means is, if you want to do business with someone or ask them for their help in a business context, don’t call them, don’t FB them, email them.


Let’s break this down for a second. The assumption is you are writing this email because you want the recipient to read it, correct? And assumption number two is that the person you are emailing gets anywhere between 10-100 emails a day. So then write that email accordingly.

Want something from the person you are emailing? Then say so! Clearly.

Let’s put it this way. If I have to respond to your email with the words “How can I help you?”, then you have failed at communicating properly.
Email is not the platform to express your most inner feelings and emotions. It is not the place to share your most meaningful experiences or your life story. Keep it short and to the point.

I know some people like to write long emails and I know some people can tolerate them. That’s fine. Others cannot. So if your email is long and does not state its purpose clearly, preferably in the subject, then take into account that many people will skim through it, others would delete it instantly.

If you want something from the recipient, then don’t bury it in a 300 word email. Say clearly what you want and then feel free to elaborate and explain the ask. But first, ask!

Things you need to take into account when writing an email in 2016:

  • Spam filters do their job well. Don’t write a spammy email.
  • The only thing better than spam filters are human filters. People will delete an email trying to sell them something.
  • People get a lot of email. Be considerate.
  • People like honesty. Say what you mean and mean what you say.


Why is it that when I hear the word “phone”, I shudder? Well, that is exactly the question we are going to answer.

Listen, I understand the power of voice. Trust me, I built a whole startup based on it. I get it. Voice is powerful and often times things get lost in text. Sometimes you just need to pick up the phone.

Now that we got that out of the way, let me say this as clearly as possible and with the full knowledge that some people will read this sentence, get offended and label me a pretentious snob. Do not, under (almost) any circumstances find my phone number somewhere online and call me about a business matter in the middle of the day without communicating digitally first and coordinating a phone call. Sounds harsh? I am just saying what many other people were afraid to tell you.

And no, calling someone randomly on Messenger or Whatsapp is no different. It is no more considerate.

Why Can’t I Call??

Before I answer the question of why a phone call without prior discussion is a big no no, let me describe to you a scenario I’ve found myself in countless times.

There I am, sitting in an important meeting, and my phone rings. I don’t recognize the number and automatically assume it’s something important enough to interrupt the meeting for. Perhaps a teacher from my kids’ schools? Maybe a relative whose contact got deleted from my phone. I’ll answer.

“Hi Hillel”, the voice on the other side says.

“Hi”, I reply.

“David recommended I speak to you. I’m looking for a job and I’m told you have a large network and might be able to help.”

At this point, I always have that dilemma. Do I politely respond explaining to the person that email is a better option to discuss this, especially since if I am going to help them, I’d need their resume and you can’t attach a file to a phone call? Or do I give in to my urge to tell them quite um, directly that it is not ok to call me mid day to ask me for a favor, while making sure to get in the question of how on earth they even got my number?

I usually choose the former and am nice about it.

That scenario happens to me, and many other people, several times a week. Yes, I can spend the time making sure my number does not appear anywhere online… or… I can have a little faith in humanity and assume people will come to their senses and understand that just because they found my number and **can** now call me, does not mean they **should**!

So why is calling someone in a business context in the middle of the day, or at any time for that matter, without previous communication, not ok?

A phone call is, in my opinion, a more intimate form of communication then email or messaging. I’m assuming that’s why you called, to communicate in a more personal manner. Except, you forgot one thing. I don’t know you. So personal communication with a stranger is a bit out of order. First; email me. Establish trust. Then we can jump on a call if we decide to do so.

Forget the philosophical/psychological aspects of a phone call. There are much more practical reasons not to call someone.

When I answer the phone, I need to stop what I’m doing. As long as we are speaking on the phone, I need to stop what I’m doing. Unlike email or messaging, you can’t multitask when talking on the phone. At least, not without sounding like you’re somewhere else and not paying attention to the conversation.

“Well, if we are talking, then you shouldn’t be multitasking anyway!” Ok, and there shouldn’t be wars or internet trolls in the world either but there are and people multitask. It’s a fact. Deal with it.

Calling someone is intrusive and without prior discussions, obnoxious. Again, if you’re over 60, apparently this doesn’t apply to you.

So then, when? 

On the flip side, often times I actually reply to an email with “Let’s jump on a call.” When? When the content of the email involves a very complex question/discussion and to reply, would require me to spend 10 minutes or more writing.

“How do I get users for my startup?”

“How do I gain more followers online?”

“How do I launch my startup?”

Really? Do you also email your doctor and ask them to teach you about medicine over email? Some things just cannot be answered by email. In fact, some things cannot be answered on the phone either and require a face to face. In any case, the underlying rule with all forms of communication is to think about the recipient and not only what you hope to get out of the email or phone call.

Messaging Apps

If you look at my home screen at any given time, you will see anywhere between 25%-75% of the screen populated by messaging apps. Messenger, Whatsapp, Slack, Instagram (Yes, it has messaging too), Linkedin (ditto), Snapchat, Wechat, Twitter, and Zula are on my home screen right now. Nine messaging apps on my home screen. Think about that for a second.

Just like email and the phone, messaging apps have their etiquette too. Of course, there is no rule book but there are certain things that just don’t work, like sending a FB message that requires me to scroll more than twice. Don’t. Just don’t.

Oh and voice messaging. I get it. It’s easier. I don’t care. I can always read. I can’t always listen.

With messaging apps, each platform has its own characteristics and what is done on Slack is not necessarily what is acceptable on Whatsapp or Snapchat, for that matter. Again, some will most definitely disagree with me when I say that I do not like business communication beyond a casual intro to be done on FB Messenger. I most definitely do not want someone sending me their resume for help with their job hunt on FB Messenger. Again, think of the recipient. What exactly am I supposed to do with that resume in FB Messenger? Email it to me!

Same goes for business discussions, especially if they are ongoing. Email or maybe Slack, not Messenger, definitely not Snapchat or Whatsapp.

The Actual Messaging in Messaging Apps

Due to the nature of most messaging apps, the communication there is somewhat casual. I read my Messenger in between meetings or during the occasional downtime. That means you should write your messages accordingly. Get to the point!

Honestly, long messages are annoying anywhere, even in email, but that annoyance is magnified when you are talking about a casual platform like Snapchat or Whatsapp. These platforms are built in a way that the communication there is snappy and immediate. Use them that way.

What that also means is that sending a question via Messenger then disappearing for hours so the person responding is talking to a wall is not ok and moderately (not moderately) obnoxious behavior.

One Last Thing…

I think my point is clear, and even if it is not, here I am complaining about long messages in my 5 million word blog post. But the point is, be considerate of the recipient in all forms of communication.

If that is the guiding principle for all our communication, then I have one more thing I must beg of you to avoid. Ok, two more things.

If you are emailing, calling (don’t), or messaging someone to ask for a favor of any kind, for the love of God, do your research before. There is nothing quite as annoying as getting an email asking for help on something that is totally 100% irrelevant to what I do. Research before reaching out.

The second thing is, please, and I cannot stress this enough, do NOT add someone to a group, tag someone in a post, or opt someone in to get notifications of any kind without their consent.

This includes, but is not limited to, adding someone to a mass email thread with their address in the To field, tagging someone on a group tweet, adding someone to a FB group, tagging someone in a FB pic not of them, and on and on. I think you get the point.

Be considerate of the recipient.

Communicate responsibly. Bad communication can lead to disasters and communication done right can literally cultivate long lasting relationships and facilitate tremendous success.


Anonymous: Hacktivist Heroes, or Bandits?


Unless you’ve been living in a cave, you have for sure heard of the operations carried out by the hacktivist collective known as Anonymous time and time again in recent years. They are they ones that have taken down thousands of ISIS-related Twitter accounts. They also received press for acts such as threatening to expose the names of thousands of KKK members; taking on NSA over censorship of free press; hacking government sites that don’t support LGBT rights, and more. On smaller scales, they have been known to use their Internet wizardry to combat police coverups; track child predators; and find evidence to support victims of assault cases. Pretty impressive stuff, right? But who are they?


The Complex Web of Anonymous


Anonymous is an amorphous group of hacktivists (hacker + activists.) As far as my understanding, they are mostly based in the US, and they make great use of the freedom of speech and accessibility of information in the public domain. They are not a static group of people. They are not an organization that would meet every week to discuss what their next mission would be. They seem to have a constant rotation of members coming and leaving. Members of Anonymous are particularly difficult to track because everyone is considered an equal, and there is no hierarchy. They constantly shift and change things up from within.
For the most part, Anonymous feeds off of ideas and concepts for the greater good. Here is an overly simplified description of how they work:


  1. A member notices that something wrong is going on
  2. Other members check to see if the problem can be fixed using the Internet
  3. An operation leader steps up, gathers troops, and organizes the operation
  4. Maybe create a video detailing the cause and outlining the plan of attack
  5. FIRE!
  6. They maybe organize a protest or two
  7. Members disband from the operation and never talk about it again.

Some of the members might join forces for other operations. Others might just leave. The amorphous nature of it all is pretty fascinating. Are you wondering if they can be stopped? Don’t bother, the answer is no. Authorities have busted members a few times here and there, and those members were quickly replaced by several more.

Characteristics of Anonymous

According to Brian Kelly, there are three characteristics that tie-in with Anonymous:

  • An unrelenting moral stance on issues and rights, regardless of direct provocation
    (Makes sense, because they usually fight against large groups for the greater good)
  • A physical presence that accompanies online hacking activity
    (They go out and talk about their missions with their videos, social updates, newsletter, protests, etc.)
  • A distinctive brand
    (Their use of the Guy Fawkes mask is no joke. The logo with the question mark, suit, and tie- woah. And their tagline is so creepy: “We are Anonymous, We are legion, We don’t forgive. We don’t forget. United as one. Divided by zero. Expect us.”)

I guess most of us don’t have to worry about being attacked by Anonymous. We can sit back, grab some popcorn, and enjoy the show. But if you’re doing something wrong- some kind of injustice using the Internet- THEIR INTERNET…. oh Mister… as Stephen Colbert once said, you’re “sticking your penis in a hornets nest.”

And by the way, they are generally good to the media. They love being in the press. They love being in the headlines. That’s because they proudly stand behind all that they do, and want everyone to know that they are doing it.



The Origins of Anonymous


Anonymous is typically known to replace parts of websites, or disable them completely. They generally take on immoral corporate giants and other strong forces. And they had a pretty interesting start. Lots of people view them as trolls who are entertaining themselves at the expense of others, but that’s not quite it. They know that the Internet is a powerful tool, and they use it for moral crusades.


The way they started was on 4chan, which was created in 2003. 4chan is a website that is totally sensor free and anonymous, where no one in charge. People can post what they want to post, say what they want to say, and see how far they can push buttons. Not quite the best place for sensitive people. Anyway, 4chan quickly attracted “netizens.” People started congregating on different boards, and found that they all shared a desire to mess with bad people. Anonymous kind of evolved out of that. They were people wanting to take things up a notch and actually do good.


Well I guess I have to backtrack for a second. Their efforts started as mindless fun, and expanded onto something more. So yes, they were screwing with people first, and the goodwill came after. There is an interesting account of them messing with a racist radio host named Hal Turner. Hal got pranked by 4chan members because of his remarks, and he decided to investigate and get the data of those people. He then published the data on his site to have his fans track down the prankers, most of which were underage. That didn’t stop him from posting their addresses online. The 4chan community told Hal take it down. He said no. Then the troops assembled and got him good. Hal was soon off the air, and imprisoned. His tactic was used against him. People in that sect of 4chan then realized that they did something good there, by getting a racist person off the air. That was when they decided to continue going on that path. As long as there was a good moral dimension to what they did, they determined their actions were good.


Operations and Shenanigans


Anonymous raised hell for leaders of the Church of Scientology. That was because they didn’t like how the leaders were trying to remove certain videos from the Internet. Anonymous attacked their website, and took most everything pertaining to Scientology off the Internet. Anonymous even went as far as doing a Google bomb for Scientology, where if you were to type “Dangerous Cult” Scientology would appear as a result. Anonymous also did a series of harmless, but intense pranks against the leaders, such as having hundreds of pizzas delivered to Scientology offices, and sending jet black faxes to them, so they would run out of ink. The leaders of Scientology had enough, and went to the FBI about it.


As part of “Operation Paypack,” Anonymous took down giants such as Visa, Mastercard, and Paypal for putting an end to donations on Wikileaks. It ended up costing Paypal over $5.5M to get out of that pickle. The bottom line is that Anonymous views themselves as the Internet Police. The Internet is not to be messed with. Hal Turner posted sensitive info of underage kids- wrong move. Scientology leaders tried to sensor the Internet- wrong move. Visa, Mastercard, and Paypal giving Wikileaks drama- wrong move.

Anonymous can’t stand hypocrisy. They don’t like it when the US Government practices what they say is illegal for others to do. The government has repeatedly done DDoS attacks and shut down sites. When regular people did so, they were prosecuted. This was especially the case when people would use software for such attacks, but it was always totally okay for the government to it, and Anonymous did NOT like that. Despite being harshly punished by the US government (10 years in prison,) DDoS attacks are viewed as “virtual sit-ins” by Anonymous. I guess it goes without saying what they did to different US government sites to teach them a lesson, haha.

There was one point they even overthrew the Egyptian government. Mubarak had shut off the Internet in Egypt, which was a major no-no. Anonymous instructed people on how to get the Internet back by setting up virtual networks that cannot be shut down by the government. They even went as far as helping people send out tweets. Same in Tunisia. And China. And many more countries.

On a smaller scale, Anonymous assisted citizens in a series of high-profile cold cases, coverups, and police brutality cases. They also launched crusades to uncover truths behind assaults, and reported their findings to authorities accordingly.

The YouTube videos by Anonymous are the perfect mix of creepy, fascinating, and enlightening. They do a great job in branding themselves. In most cases, they say what is happening, and what is going to go down. This keeps them from being scapegoated, and also stops others from claiming their work. Here’s a vid of Anonymous sending a message to Kanye West, which went crazy viral when it came out.


It takes a lot of work to become a member of Anonymous, it’s not a matter of just filling out a form and joining. You need to prove your worth with ideas or skillsets. You will later be invited to participate to become an Anon. They will call on you if you have other skills they can tap into. You can write web copy for them, help with videos- and contribute to Anonymous in many other ways without being a coder. Interestingly enough, only about a fifth of their members are actual hackers. The majority of them are protestors. Even though they don’t have a hierarchy, they do have a few people who take initiatives on certain operations. I guess it comes down to how organized and efficient they are.


So what are your thoughts on Anonymous? Are they heroes, or bandits? They aren’t digitally stealing money, so they are not after financial gain. They are just exposing people doing bad things. Of course, there are some members who may go astray. All groups have a few bad apples. But the ones that get the most press are the good ones. There are also repercussions to all the actions taken by Anonymous in the real world after all is said and done. There are always cases of people getting treated unfairly, post-operations. There are indeed immoral dimensions to Anonymous’ moral actions as innocent people become casualties in their crusades. I’d say that’s the darkest spot in their efforts.


I personally side with them in most of their operations. I’m all for social justices being made, especially when higher authorities decide to take the backseat. The tech aspect of it all is just so awesome. Tech superheroes for the win!

The Beauty of Pebble Classic and Pebble Time

I have been using my Apple Watch pretty heavily since I purchased it soon after it came out. It took a little bit of getting used to, but I loved it from the get go. That reminded me of how much I loved my very first smart watch, the Pebble Classic. I previously wrote about how I found the Pebble Classic to be a total game-changer, and as you can see now- it was indeed.


An Interview with Om Malik on Blogging, Tech, and The Bubble

A few months back, I decided to start something a little different with this site and in addition to posts on tech and marketing, I decided to add interviews as well. I wanted to interview the shakers of the industry, but first and foremost, I wanted to get the opportunity to interview the people that inspired me to start writing. I can now say, mission accomplished.


All Time Funniest YouTube Video

I think it is safe to say that I spend a significant amount of time on the Web and a high percentage of it watching videos. I have watched quite a few YouTube videos in my time, and although I first saw this video years ago, it remains my favorite video of all time. This guy really sums up our tech generation perfectly. Please share some of your favorite Youtube videos in the comments.


The Top Five Reasons Why 3D Has No Future

If, like me, you’ve been following coverage of the 2010 Consumer Electronics Show, you will have noticed that the big trend this year was 3D TV’s. All of the major flat panel manufacturers were in Las Vegas showing off HDTV’s capable of displaying content in 3D. This fact, coupled with the runaway success of James Cameron’s 3D film “Avatar,” has brought the third dimension back into the limelight. With so much buzz around 3D, you might be wondering whether this is the future of cinema. Don’t believe the hype. Here are the top five reasons why 3D has no future:


iPhones and iMacs in Movies: Does Apple Pay?

As regular readers of this blog know, Hillel is a huge enthusiast for all things Mac. So am I, having bought my first iMac two years ago and never looking back. Since then, I’ve also purchased an iPod (5th generation), and my husband bought an iPhone, which has bailed us out on numerous occasions. Recently, Hillel and I got into a conversation on Twitter about Mac product placement that started with the following Tweet…


8 Reasons to Consider an iPhone Over A BlackBerry

One of the few disadvantages of the mobile advancements we are making is that consumers get bored of their mobile device after a very short period of time, or when the newer model comes out, whichever happens first. This is true for a lot of people I know, and it is true for me as well. On the flip side, when I get a new phone, I generally spend the first week or two getting to know the phone, and it is usually accompanied by excitement and enthusiasm about my new device.