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.


The Only Thing Instagram Stories Killed for Me is… Instagram

Instagram stories, Snapchat, yada yada. So much has been said about Zuck’s repetitive and systematic ripping off of Snapchat so I will not be adding to that echo chamber. Before I talk about how the launch of Instagram Stories affected my personal usage of both platforms, I would like to talk a little bit about the phenomenon of copying. It sucks. No, really. Speaking as someone who has been plagiarized and blatantly copied, it royally bites.


An Interview with Saul Singer, Co-Author of the Book ‘Startup Nation’ and One of Israel’s Greatest Thinkers

Over the years, I have done quite a few killer interviews and I am very proud of the long list. Having said that, the opportunity to have interviewed Saul Singer is definitely at the top of my list. If you are not familiar (how are you not familiar?), Saul wrote the book “Startup Nation” along with his brother in law, Dan Senor.


10 of the Most Annoying Things People Have to Stop Doing on Social in 2014

Gosh, I hate posts like this. Not only is it somewhat of a rant, and if you follow me online, you must have realized that I am highly allergic to negativity, but it is also about annoying things people do on the social web. So much has been said about it and again, nothing I dislike more than repeating what has already been said… Having said all that, this is, sadly, an important post for too many people.


The Two Words You Need to Know in Order to Effectively Market your Brand on the Web in 2014

So I was asked to come speak at a Microsoft Bispark event last week. The topic I chose was how to market your brand in 2014. I know, shocker. The thing is, I genuinely believe that my whole “philosophy” in marketing can be summed up in two words. Of course, you are going to have to watch the entire speech to learn what the two words are.