How to follow up with sales prospects in 2019 [1 hour crash course]

The first call. The first email. The first meeting. Getting the ball rolling is the easiest step but if you don’t have a follow-up plan, you’ve already lost. Why? Because amazing deals and valuable relationships don’t happen on the first try, or even the second or third try.

If you truly want to become a priority for someone, you have to follow up. You have to push past the fear of rejection and half-hearted maybes to get results.

In this 1-hour crash course, Steli Efti is going to show you how to master the art of the follow-up in order to win in life and business. You can watch the video or read the transcript below.


All right guys, welcome to the special Close webinar, The Follow Up: How to Master the Art of the Follow Up! And crush it in business and life. All right. The follow up is one of the most important things to do if you truly want to master the game of sales and life and entrepreneurship if you ask me if you want to master the hustle. So this is one of my favorite topics and it’s the single highest ROI piece of advice I give on a daily basis. Measured by the feedback I get every day by people emailing me the amazing results they were able to generate by amping up their follow up game and following some of my follow up advice.

So I’m super thrilled if we just get some of you people to do a little bit more follow up and be a little bit more persistent in life and we will create insane value in the next 60 minutes.

From running outsourced sales to creating our “secret sales sauce”

All right. So let me first tell you a little bit about myself and give you some context and background why I care about the follow up. Obviously, I’ve been a serial entrepreneur my whole life. I’m completely unemployable. I never had a real job. And my entrepreneurial super power has always been the hustle. And one way or another, I’ve always been able to sell people my ideas, sell people on our products, get customers to buy in and get investors to invest, get the press to write about, get people to join the company.

More recently and more relevant to this topic, I started a company called Elastic Sales. And what we did with Elastic originally was we helped over 200 venture-backed startups in Silicon Valley scale their sales operations. We were the entire outsource sales department for some of the hottest B2B SaaS companies out there.

And in the process of doing sales for so many different companies, we learned a thing or two about how to do sales and how to do sales well especially for startups and new companies, and we utilized the power of the follow up to create outsized results and returns for our clients.

Now, from day one as we were building Elastic Sales, we started also developing internal software, piece of sales software that allowed us to outcompete our competitors, to make our salespeople more productive, and to scale sales at that level of complexity. And that piece of software eventually got named Close.

Close was originally called our secret sauce and was just meant for internal purposes and use but eventually, the software got so good that our customers started asking us if they could also buy the software and not just the services. We got our salespeople to show other salespeople Close and go, “Ha ha ha! You can’t buy the software. This is only for people that work at Elastic.” And we started getting salespeople giving us sales calls, trying to sell us on the idea that we should sell them our sales software. There’s a lot of selling going on there.

And so, the outside market started showing us and signaling us that the software we built was pretty powerful and they wanted it. And eventually in January 2013, we decided to release the software, launched Close and what we thought as a parallel small business in comparison to our big services business and what ended up happening was the Close grew so fucking fast that within a year, it was a bigger business than Elastic and we fully focused on it.

And today, Close is insanely profitable, high-growth SaaS business. We’re one of the best, if not the best sales software out there especially if you’re doing inside sales, which means if you are doing a lot of emailing and calling, we’re the best piece of software out there and we’re going to help you close more deals and make more sales happen.

What a Thai fruitseller can teach you about following up

All right. Enough about the background. Let’s jump right into the magic of the follow up. Here is a little story I want to start the webinar with. Thirteen years ago, I was travelling through Thailand in Southeast Asia and I was travelling with a special group of people, those people were all hypnotists. And the group was led by a master hypnotist that is probably one of the best hypnotists around the world. So this is a special group of people. We’re about 20, 25 people that are all studying hypnosis. Don’t worry. You’re not going to get hypnotized today. It’s not part of this webinar. And these people are all experts in communication, really interesting personalities of people, and we’re travelling through Southeast Asia together. It’s a pretty wild adventure.

One day, we arrived at a little town. And what we want to do is we want to go to the ocean and rent a little boat to get to one of the most southern islands in Thailand called Ko Lipe. It’s a beautiful, tiny, tiny island, and probably it’s like 30 people living on it. And we were super excited to go to this like little jewel on the ocean.

So we go to this little town and that master hypnotist is like, “I’ve done this before. Let’s get to that house. I think that’s where the captain is and we’re going to try to get a charter boat to get to Ko Lipe.” All right, cool.

So here we are, 20 guys and gals, we’re standing around in front of a house. We’re waiting for this master hypnotist to rent the boat and we’re just standing there waiting. We just had lunch and we’re just like getting barbecued in the sun.

And all of a sudden, there’s a lady on a bike and she sees us. She sees there’s a group of people that appeared to be tourists and she is biking over to us. And at the back of the bike, she has like a little stand with like fruits on it. So, she bikes her bike with a mobile fruit stand in front of us. She jumps off the bike and she starts approaching all of us with a big smile going, “Fruit, fruit, fruit, fruit.” And she’s waving her hands and showing us her fruits and she goes, “Do you want some fucking fruit?” And we all laugh and we smile and we nod and we go, “Yes, thank you so much but we had just lunch and we’re so full and no thanks. We’re really not in the market for fruit right now.”

So, she just continues going on, “Fruit, fruit, fruit.” Not giving a fuck about us rejecting her one way or another. Eventually, the master hypnotist comes down, he approaches the group and says, “You know, this was the wrong house. It’s the other house, a few houses down. Let’s just go right over there and I’ll go in and I’ll try to get us the boat.”

All right. So we all walk down a block or two. He walks into this new building and what do we see? The fruit seller lady jumps back on her bike and she follows us on her bike. She stops right in front of the group. She jumps off the bike again and she again approaches us going, “Fruit, fruit, fruit, fruit.” We all started laughing again, “Ha ha ha! Yes, we can see that it’s fruit. We totally get it. We appreciate your hustle but thanks but no thanks. We’re so full we really don’t need any fruit.”

Eventually, the master hypnotist comes down again out of the building and goes, “Guys and gals, I booked us the boat. That boat is that blue boat over there. Let’s go and stand over there. He said he’s going to be over in 10 minutes and we can get started to get to Ko Lipe.”

So we all walk over there to the boat. What does the fruit seller lady do? Exactly! She jumps back on her bike and she bikes right in front of the group again, in front of the boat, jumps off her bike and does the same routine, looks at us with a big smile and starts hand waving and going, “Fruit, fruit, fruit, fruit.” And eventually, one of us goes, “You know what? It’s a 3-hour boat ride. Fuck it! I’ll buy some fruit.” And then the next person goes, “You know what? Maybe it’s not a bad idea. I’ll buy some fruit too.” And eventually, everyone buys fucking fruit. Everyone! Twenty-five people, we all buy fruit from her.

An hour later, we’re on a boat, a little boat, shaky boat all the way to this little island and we’re all eating fruit, looking at each other going, “Fruit! This was an amazing idea.” This fruit seller lady knows the secret of the follow up hustle and she realized in one way or another, consciously or subconsciously that it doesn’t matter how well you communicate, it doesn’t matter how influential you are or how persuasive you are, this was a bunch of people that hypnotize other people for a living, people that are masters in communication. And here we are being influenced and sold by this nice fruit seller lady. Why? Because the person with the highest clarity in the room always wins and because the person that is most persistent always, always wins.

Here is one of my favorite quotes from Paul Graham, if you’re into startups, you know who P.G. is? The founder of Y Combinator, “You can be surprisingly stupid if you’re sufficiently determined.” That’s the magic of the follow up.

What happened when I followed up with a billionaire over 48 times

So I’ve told this story plenty of times but I will summarize it again for those that haven’t heard it before. A lot of times when people wanted me to tell them what kind of a magical result I’ve been able to create through the power of follow up, I tell them all the time I followed up with a billionaire over 48 times before I got him to invest in our company.

And here’s the whole magical rundown, step-by-step of what happened. We got an investor to invest in us and we asked him to connect us with this billionaire guy. He says, “Yeah, I’m good friends with him. I’m more than happy to send an email.” He sends an email and that billionaire guy replies and goes, “Yes, I’m happy to meet. This sounds interesting.”

I respond and I go, “Oh, this is so exciting. How about meeting Tuesday or Thursday in this or that time?” Silence. I send another email. Silence. Another email. Silence. Forty-eight emails later, you know what his reply was? “Steli, thank you so much for the follow up and the follow through. I had a big crisis going on. I had to leave the country and go overseas and this and that happened. I’m back. Can you make it tomorrow at 1:00 PM to my offices in San Francisco?” I made it and he invested. That’s the magic you can create by just being persistent and following up no matter what happens until you get a result.

“Yes” is good. “No” is good. But “maybe” will kill you.

Now, my follow-up philosophy is very, very simple. I never ever, ever, ever stop until I get a result. Yes is good. No is good. Maybe or silence isn’t. And that’s by the way what is crushing startups is typically not that they’re getting a lot of bad results. What crushes and kills startups is not that they’re getting too many nos. What crushes startups is that they get too many maybes, is that they are living in that maybe zone, that “I emailed them, they liked it, and now, I don’t know what’s going to happen next.” Oh, how is this big deal coming along? “Kind of good, they are talking about it internally. We’re waiting to hear from them. I’m really hopeful that it…” that shit is what’s going to kill your startup.

If you get rejected by everyone, that’s not a problem. If you get a no from everyone immediately, that’s awesome. You know what that means? “Shit! What we’re doing isn’t working. Let’s completely change what we’re doing.” That’s a clear result. If you’re getting a yes from everyone and everything is going well, that’s obviously amazing. The thing that kills most startups is that they live in a zone in between the yes/no. They live in a zone where there’s no clear result. And that is going to kill you. The fortune is in the follow up because the follow up will generate results, outcomes, yes or no.

I really don’t care what I get. If somebody tells me no, I’ll stop following up with them. But until they do, I will never ever stop following up. If you just follow this simple rule, I guarantee you, I’ll bet you any amount of money you want if you just follow this simple rule, it’s not rocket science, if you just start following up with people indefinitely until you get a response, you will generate results in your life and in your business that you only dreamed of yesterday. It’s as simple as that.

Why most people suck at following up

Now, why are most people bad at this? Why do I even have to tell this to people? Why do I have to give webinars about following up? Why isn’t this so simple and so obvious that everyone does it? It’s very simple. It’s two things. It’s really just one thing to be honest. It’s fear. It’s as simple as that. We are all afraid of being rejected. And every time we send an email and we don’t hear back from people, we feel more rejected. People don’t like to be rejected. We all don’t like to be rejected.

So what happens as a result of that is that once we send one or two emails, we’re like, we can’t take anymore the silence which really translates into direct rejection, and we stop. We all are afraid of being rejected. We all are also afraid of being somebody that’s needy. Like we all have egos and our egos want us to look great and be amazing and be cool. So we don’t want to seem desperate and needy. We don’t want to be annoying. And because we try to avoid all these negative things, we don’t want to keep following up with somebody because we think we’re now an annoying and needy loser.

All that is bullshit because what that implies and what that needs to exist is some form of mind reading. You need to take the silence you’re getting when you’re emailing somebody and I’m going to address what I told to that billionaire how many times I emailed him in a second so these questions are really good ones, guys. I see them coming through. I’ll address them in a few slides down the line.

So, the reason why we are afraid of that rejection, the reason why we don’t want to be annoying and all that is because we take that silence and we make up a story in our mind that’s bullshit. When you get silence from somebody that you’re following up, your story is probably, “This person doesn’t like me. He or she thinks I’m ugly or stupid. They don’t like our idea. They are arrogant. How dare them not responding.” You make up some fucking story in your mind. I’m not a mind reader. I don’t make stories up in my mind.

You know what my hypothesis is when somebody hasn’t replied to me? They are busy. They have something better to do than reply to all my fucking emails. We might have had a good conversation. The reason why they are not responding right now is something happened, maybe in their life, maybe they are sick, maybe with their family, maybe in their business, maybe there’s a crisis, something. They got busy with something else and I am not the highest priority in their life right now. And that’s fine with me. I’m going to take it up in my hands and it’s my responsibility to manage this relationship until they get a chance to respond. That’s the story I have in my mind. If they don’t reply, they are busy. That’s as easy as that.

I told you guys about like all the amazing feedback I get from people telling me the amazing shit they are able to generate in their life by following up. We’re actually putting together a book. It’s going to be like hundreds of stories of people making magic happen by just following my follow up advice. I’ll just share a few ones here in the middle with you guys to just increase your belief in this and make you realize how simple, how something as simple as this could make a difference in your life.

How real people are using the follow up to get results

Here is Nathan who is a YC founder who responded and commented on one of our videos, “On the 12th follow up I got a meeting scheduled with a potential customer that had gone silent. Also, a back channel request through an existing customer got me an intro to a potential customer in a new market. Thanks for the motivation and the kick in the ass!”

And I met Nathan a few weeks later in person and he told me they closed a 6-figure deal by just keep following up with that prospect.

Here’s another case study. “Steli’s philosophy on following up sent me back to significant prospect that had gone very cold. A mix of forty-one emails and voicemails later, I got my response. And the response was, ‘You win! Let’s connect at the trade show.’ Long story short they’re on-boarding this month as a customer.”

I could go on and on. People tell story about how they got press articles, how they got investors, how they got customers, how they convinced somebody to join the company. You will create magic in this world if you just keep following up until you get a result. As easy as that.

The nuts and bolts of following up: How to actually do it

How frequently should you follow up?

Now, let’s talk about some tactical nuts and bolts stuff about this. What should be your follow up frequency? So because somebody also in chat asked, “Hey Steli, how many times did you follow up? How often did you follow up? Was it by email daily, weekly?”

I was pretty persistent – with this particular billionaire, because we were raising money and we had to make it happen fairly quickly, we almost closed the round before he invested. I followed up a lot. And in general, the frequency that you want to have with this stuff is that you want to follow up very frequently at the beginning and then you want to broaden up the frequency over time.

So as an example, if we just had a good meeting and a good conversation, my next follow up could be today and then my next follow up could be a day or two later. And then the next follow up is like two or three days later and then a week later and then two weeks later and then a month later. And then after that, maybe every month, maybe every two months, and eventually, if could be every quarter. So what you do is you do a high frequency and density at the beginning of the relationship and then you’re broadening and spacing it out over time.

With this billionaire, I was probably very, very, very insistent and I emailed him multiple times every week for a number of weeks. And also, I’ll get to for – and I’ll get to what I was telling him but it’s really not fucking rocket science. It’s very beautiful. We’ll talk about that in a second. So when it comes to follow up frequency, what you want to do is more frequent at the beginning and then spacing it down less frequent over time.

Which channels should you use to follow up?

Now, let’s talk about follow up channels for a second because there is a hierarchy to this shit. If you take email as a follow up channel, the beauty of email, it’s very un-intrusive. So it allows the person to either read it or not, respond to it or not, delete it or archive it, or snooze it. It gives all the power to the person how and when to respond to it. It’s in their inbox and their inbox are usually pretty full so it’s not the most intrusive in your face medium.

Email is probably the medium in terms of follow up that you can use for the highest level of frequency and the longest period of time. So you can send somebody 48 emails over a few months. That’s totally fine. That’s very aggressive but it’s fine.

But with email – so email allows you to do the highest level of frequency over the longest period of time but it’s the least urgent channel. So what I mean by that is that if you don’t have urgency, if you don’t need somebody to respond immediately to what you’re doing and there’s not a deadline, email is probably the right channel.

Now, if what you’re doing or what you’re trying to accomplish with this person is more urgent, you need to move up the ladder in more urgent channels. So more urgent than an email could be, a letter, an SMS, or a fax, it could be some social media. But even more importantly, let’s go from an email to an actual phone call.

So if you call me, that’s a lot more interruption within my day. If you call me, you text me, it’s a lot harder for me to ignore. Therefore, you don’t really have the credit to call me 48 times or leave me 48 voicemails. Forty-eight emails over a long period of time is one thing. Forty-eight voicemails, way too aggressive.

So what you want to do is if you don’t have urgency, you just use email. If it’s more urgent, you might want to go one level above and pick up the phone and call somebody. And even one level above that urgency is to actually show up in person. There’s no ignoring you if you are in my office. You’re standing right in front of me and you see me and I see you, it’s very hard to ignore you. I can’t snooze you or archive or delete you. I have to acknowledge you.

So in person is the kind of the most disruptive, the most kind of – the most disruptive channel to do in follow up. But it’s also the one that you can’t use indefinitely or with high frequency. So obviously, you can’t show up with somebody 48 times in front of their house without being arrested. Exactly. That’s kind of stalking. So if you showed up in somebody’s office 48 days in a row, it might get you in trouble. But you would not believe how many multimillion dollar deals have been saved by people showing up in somebody’s office.

Like Sam Altman who is currently President of Y Combinator, he was running a startup and he shared the story once where they were working on a multimillion dollar deal for months and months and months to then the final few days of the deal get an email from the customer saying, “You know what? We’re really sorry. But we’ve decided to go with your competitor.”

And they were crushed for half a second and then you know what they decided to do? They bought a fucking ticket to New York. They were based in San Francisco. They flew to New York. And the next day, they showed up at that prospect, at that customer’s office and they went, “Hey, we saw your email. We were in New York anyways and we thought we’ll drop by and just say hi. It’s really sad that it didn’t work out but we thought we might have a chat.”

What happened? They got invited in. They sat down and they had a chat. They discovered what the customer thought and why the customer thought they needed to go with the competitor. They addressed that concern and went into a deep technical dive. An hour later, the customer changed their mind and bought from them, multimillion dollar deal saved by them just showing up in person.

There are a million examples of this, a deal going cold and then a person going – either in email and go, “Hey, I’m in the area. Can I buy you some lunch, dinner, or coffee?” Or just showing up at the office and going, “Hey, I was just in the building. I’m visiting this other customer. I wanted to say hi.” Millions and millions of deals have been saved by just showing up.

Again, it’s kind of a – it’s a thing you can’t do indefinitely, you can’t do a lot but once in a while, you get on a fucking plane and you show up somewhere to close and win and save the deal.

The dos and don’ts of following up

Let’s talk about do’s and dont’s on the follow up and this relates back to what I did and what I was saying when I was following up with that billionaire. Number one thing is you need to be friendly and you need to keep it short.

So my follow up emails honestly, lack any and every piece of creativity. All my emails sounded something like this, “Hey, another beautiful day in paradise. Here’s a new press article about our company. Can we meet this Tuesday or Thursday?” The next email would be, “Hey, another beautiful day in paradise. We just hired this amazing person. Can we meet today at this time?” The next email would say, “Hey, another beautiful day in paradise. See, we just crossed this big milestone. I want to tell you about it. I’m so excited about meeting. When can you meet in the next 48 hours?”

All my emails were just that, just one sentence saying something nice about our company, a bit of news, and then proposing a time to meet. That’s it. You never want to apologize for emailing them, “Hey, I’m so sorry that this is the 10th email.” You never want to reference back to all the emails, “Hey, this is the 47th time I’m emailing you. I don’t know if you read any of the 47 emails. But if you haven’t read any of my 47 emails, I thought I will send you the 48th.” Shut the fuck up. You’re wasting time. Just tell me what you want. Just get right into it.

Be friendly. Be nice. Don’t make me feel guilty. Don’t complain. Don’t go, “I don’t know why you’re not answering any of my emails. I mean you might think that you’re something better than me.” Don’t talk shit like that. Don’t make me feel guilty. I probably already feel guilty and bad because I know I should reply to you. I know you’re a good person. I know that I had a meeting with you and promised you a deliverable or a decision or something. I know I’m late. I know I’ve ignored you. Don’t make me feel even more guilty. I will never respond if you make me feel bad or guilty. Don’t be needy. I don’t need that in my life. Just be professional, clean, nice, and cut, friendly. Keep it short. Provide value and shut the fuck up. Like just keep it moving, very, very simple.

I have people sometimes, they are just nuts. They will send me a message on fucking Facebook. And I’m not really on top managing all my messages on Facebook. So I get a message from him on Facebook that’s like, “Hey Steli, I’m a big fan. I really need your advice about X, Y, and Z.” And two hours later, they’ll send me a follow up message on Facebook and start complaining that I haven’t answered yet. They’ll go, “Oh Steli, it’s outrageous that you haven’t responded yet. Do you think that you are star now just because you have a podcast?” And it’s like Jesus fucking Christ! Dude give me a break. Maybe I’m not 24/7 reading my Facebook messages. Maybe it’s not my fucking responsibility to answer your message within two hours. Give me a fucking break.

You know the most guaranteed response to somebody that approaches me with this level of aggressiveness and neediness and trying to make me feel guilty? You know what my response to all that shit is? I delete the message. I don’t need that in my life. I don’t owe you shit. I want to help you. I want to respond to you. But I don’t owe you anything. So don’t make anyone feel guilty because you follow up 10, 20, 30 or 100 times. Just keep it clean cut, friendly, and nice, short and simple and you’ll get good responses.

Some people ask me, “What do you do – do you follow up when somebody tells you no?” And the answer to this is really, it depends. I think first and foremost, all of you need to worry about following up more. If you don’t want to follow up indefinite – if you can follow up indefinitely, magic will happen in your life until you get a yes or no. If you get to that level, you are above the rest. You need to realize you are now running a race when you no one else is running. You are going to win.

If I can convince you of doing that, we already made this a special hour in the universe. We created an insane amount of value for the world.

Should you follow up even after hearing no?

Now, what do you do when somebody tells you no and should you follow up then even in that case? You know what? That’s black belt shit. That’s like when you already have your follow up game down to a tee and you’re always persistent and you always follow up, yes, let’s have that conversation. But I don’t want you to worry about that first.

So if you already a pro on the follow up game, yes, let’s talk what to do in there. My answer to, should you follow up when somebody tells you no is it depends. It depends how big and how valuable the conversation relationship could be for you and them and for your business in the long term. A lot of times people have responded to a no and follow up to a no then turned it into a yes.

I know about some really creative users where somebody got rejected and then – I mean you saw that these guys where I told you that jumped on an airplane and flew to New York. They got a no. They got rejected and they still followed up by showing up in person and making a final attempt to win the deal.

There have been people that I know who got a no and then they sent that person a gift and it was maybe – I don’t know. One story was like in Canada and the guy sent the person a hockey stick with a little quote card that was saying, “You will lose 100% of the attempts that you never make…” or something along those lines.

So I remember somebody sending somebody an article about why you should never accept the first no and how to handle rejections. There was a little quote that said, “Hey, this article inspired me. After getting your rejection, I was crushed. And then I read this article and it inspired me. I hope it will inspire you too.” And a day later, they called that person and went, “Did you read the article? I just wanted to make sure you got it.” The person was like laughing and saying, “Yes, this was really creative and really cool.” And they start talking again and they figured out, “Hey, why did you say no in the first place?” And eventually, he turned them around and made them a customer.

So, there are some people that will follow up even when they get a NO but that I think that it depends on the relationship, it depends on what you’re selling, the value that you’ve created for both sides, it depends on how up your game is in terms of the follow up magic that you can create.

Reaching out and following up with cold contacts

Now, I see that a bunch of people are asking very good questions about what do you do with cold emails? What do you do when you are reaching out to somebody cold that never heard of you, they never talked to you in person, on the phone or via email, they never responded or replied positively in any shape or form or way? What do you when you cold email someone or cold call someone that you don’t get a response or reply? How many times do you follow up and what’s appropriate there?

There are some studies that say that when you do a cold outreach, you want to follow up between 4 to 8 times. Four to eight times is probably the right frequency of following to a cold outreach. Forty-eight might be too much.

But then again, I know people that – there’s a company in the UK that is doing SEO services. They have been following up with me. I’ve been ignoring them of the past three years. And they probably have followed up like 24 times in the past two years, probably like every month I get an email from them. And I never delete them. I always archive them because they’re always clever. They’re always fun. They’re always short. I kind of feel for them they’re hustling, they’re young, they’re cool startup. So I’m like, yeah, I totally get it. I don’t need SEO services right now so I’m going to archive this. But I’m not deleting this. I’m not even annoyed by it. I kind of respect the hustle that they have and the follow up.

And I guarantee you, if I ever need SEO services, they’re one of the first companies I’ll look up because I just know, I know who they are. I know about the company because they never let me forget. So it depends on your philosophy. It depends on what’s authentic to you, how aggressive you are. But I personally would not follow up indefinitely with a cold contact. We follow up typically 8 times with a cold outreach. That’s probably a good rule of thumb.

The break up email, or how to become a priority if someone has ignored you

All right. Now, I’ll go against everything I’ve said and I’ll give you a tip or a hack. This is usually used in automated communication, how to break up with somebody when they don’t respond to your emails. So, there’s an email that’s called the Breakup Email. It’s a specific format and if you use it, you’ll get an insanely high amount of response rates to these emails. It’s going to be very, very successful.

I most of the time would not use this in my personal follow up although you can. But if you use drip emails, if you have some kind of a funnel where people come and they sign up for a free trial or they contact you or they download an ebook or a whitepaper or anything, they get into your funnel and you send them a number of drip emails, automated emails that say, “Hey, shall we jump on a call? Hey, read this book we wrote. Hey, do this. Hey, do that.” And it’s kind of like customized email communication that’s automated.

What you want to do is you want to have a breakup email that’s so on point when they don’t respond. And here is how that breakup email goes. A lot of the biggest and most successful B2B SaaS businesses are using this email template because it works. Here is the simple format. You write a subject line that says something like, “Goodbye from Trunk Club” or goodbye from – this is an email I got from Trunk Club. It’s a B2C company. I got the exact same email from HubSpot which is a B2B company. And there’s a bunch of other companies that do this.

You write, “Goodbye from Steli” or goodbye from your company. And then in the email basically what you say is you say, “Hey dude, I’ve been trying to reach you multiple times over this period of time. I never heard back from you. So what I need to do right now is I’m going to assume that you don’t care about this anymore. I’m going to take you off my list. You will never ever hear from me again. Whenever you’re ready to talk, here’s all my contact information. I’ll be excited to chat with you but you will not hear from me again. Goodbye.”

This email is insanely successful. You take something away from people and they will jump off their seats to get it back. It’s so funny. It’s just psychology 101. You take something away even if they didn’t really want it that much, you will make it more valuable. So the breakup email which is an email where you basically tell him, “Hey, I’m going to stop emailing you. You will not hear from me again. If you want something, if you were interested in this topic, you can get in touch with me anytime but I’m taking you off my list.” It’s money. That email is killer. It gets insane open rates, insane reply rates. So use it at your own discretion and use it wisely.

Now again, for the follow up ninjas, what’s the response – so Evan asked what the response rate is for this goodbye masterpiece. It depends. Every company gets different response and reply rates. I think the open rate, what I’ve seen is 50 to 70% when you have a “Goodbye from Steli” in the subject line. It’s going to get very high open rates.

And then on the response rate, it’s really depending on the quality of list, the quality of the company that you’re at. So those vary but I’ve seen response rates for this that are very, very high. I mean we’re talking 30, 40, 50% response rates which is insanely high for a group of people that have ignored your prior 7, 8, 9 or 10 emails, very, very high.

I’m sure there are companies that are much lower, some companies that even higher than what I say. But I’m telling you, out of all the emails that you sent us, it’s probably one of the emails that get the best open and response rates.

Put some funny in your follow-up


All right. So let’s talk about the – again, for those of you that have the ambition to become the black belt master in follow up, a ninja in follow up, you can put some fun in your follow up to just brighten it up and make it a bit better.

So there is this guy that runs a business that basically coaches people in business to be more funny. And he sends me an email one day and he goes, “Steli, I love your talks. I love everything you do. We need to work together blah, blah, blah.” I ignored it.

I got another email from him that says, “Ha ha ha! I know that you’re ignoring it to test if I’m really good at follow up. I’m reading all your shit, Steli. I am going to follow up forever. You can’t shake me off. I got this follow up thing down.” In my mind, I go, “Oh really? Let me see if you truly live that.” So I archived that in my don’t respond.

He sends me another email with some funny thing going, “Hey, I’m going to start showing you some badass follow up moves.” And I think, “All right. I’m going to ignore you.” What does he do? He sends me another follow up email. In that email, he has a cookie monster GIF and that’s all that’s in the email. It’s an email with this GIF. And it’s the cookie monster waiting. I started laughing when I saw that. I’m like, “Jesus! This guy is really truly good. This is kind of funny. All right. Archive.” I’m thinking, “Hey, let’s see what else he can do. He has been pretty creative so far, let me see what else he can do for me.”

After this GIF, he sends me another one or two GIF. One is of a haywire that’s going through an empty town and there’s something else. It’s just some funny GIFs that are basically communicating to me, “Dude, I’m waiting. Please give me a reply.” All funny, all good shit. I’m saving everything. I’m laughing. I’m like, “All right. I’ll still keep ignoring this guy and just see what else he can teach me.”

Then the next thing he does is he sends me a video. He says, “Hey Steli, since you’re not replying to any funny GIFs or any messages, I made a video for you.” I say, “All right. I’ll check it out.” I click on the play button. And it’s this dude and he starts talking and he’s like, “Hey Steli, it would be really great to get a response from you. I’ve been following up for this time. I really think we should do something together. Come one, my man. Blah, blah, blah.”

And while he’s talking, I’m thinking, “All right. That’s not that creative. I mean OK, you made a video. I watch it. I appreciate it. But it’s not that good.” And the moment I think that, left and right, there are two guys showing up with guitars and they start singing in the video and they’re like, “Oh, it’s the follow up blues. Oh, it’s the follow up blues.” And they sing this follow up song. And I started laughing and I think, “Oh, all right. This is much better than what I thought.”

Then I’m thinking, “How did they do this?” And I’m thinking, “They are not – they did not just do this for me.” So now I’m thinking, “Oh, they created this follow up song and then every time he sends an email to somebody, he just creates that first part of the video where he’s alone and he goes, ‘Hey John,’ and then he creates the next video and he’s like, ‘Hey Steli, we should really blah, blah, blah.’ Then he creates another video and he’s like, ‘Hey Bob,’ and all he needs to do is he has to edit the second part where he does the generic song.” I’m thinking like how did he scale this?

So while I’m thinking, “Oh, probably this is a generic song,” these motherfuckers start saying my name and our company and they’re like, “Oh, follow up song. Come on Steli, respond. Oh, Close.” And they just – it’s clear, holy shit! They made that whole video just for me. They created that whole song just for me. And I’m like, “Holy shit! These people are legit. Like this is fucking gold.”

And what do I do? Did I respond? No! I archived. Why? Because I’m thinking this guy is on a roll. I want to know what he’s going to do next. He sends me another one or two emails. One of them is just like, “Hey Steli, now I’m concerned if you’re still alive. Just type any random number or keys and hit reply so I know you’re fine.” And he does a few more of these jokey things.

And then eventually gives out and he writes me. He goes, “Steli, come on man. You’re killing me! I’ve nothing else I can do here.” And eventually I responded. I’m like, “All right dude. You did an amazing job in your follow up hustle. All I wanted to know is to see what else you can do.”

And you know what I did, I took all his emails and all his tactics and then turned them into a blog post, Put Some Funny in Your Follow Up. If you type that into Google, you’ll find the article. And that article got picked up by a bunch of other blogs and it got him tons and tons of business. And we got tons of traffic and new sign-ups through that article. So we all won.

The reason why I show you this is a) to show you how you can be a little creative. By the way, if you want to use any kind of GIFs, you can just go into Google and type in cookie monster waiting and you grab that GIF and use it. But more importantly, I want to show you who you are competing with. There are people out there that will not give up. These people will crush you. Become one of these people and you will crush it in your market and you will crush your competitors.

Optimize for being valuable over being liked

So, Julia is asking an important question here which is like, “Hey, what do you do when you are serving a super conservative and very professional customers?” So I mean you probably – you need to speak in a voice and in a tone and tonality that will speak to your audience. So maybe you don’t want to have a follow up song or a cookie monster because maybe that will not work for your audience. But you definitely want to follow up and you definitely want to be persistent.

And you need to think about it this way. Sometimes people ask me, “Hey Steli, what if I piss off someone by following up so much?” And here is my response to this, Julia and Nigel. If there are ten people and seven of them hate me and three of them love me and the three that love me, they and I, we create massive value together, that’s fine with me. I’d rather have seven people hate me and three love me than if I have ten people that are equally indifferent above me and we created zero value, we made nothing happen, and we had all these conversations that led to nothing.

Business is not about being liked. Business is not about being loved. Business and life in my opinion is about creating value, making things happen. So I’m not optimizing for being liked. I’m not optimizing for not being convenient to other people. I’m optimizing for creating value.

So maybe in your audience, 48 follow ups is too much and this is probably true for many audiences. Maybe 4 or 5 or 6 is the max that you can do. I don’t know what the right number is. But I challenge you to challenge yourself and try to double or triple the amount of follow ups that you would usually use and see what kind of results you get.

And please, when you look at the results, look at them holistically not by did I piss anyone off? But by, “Hey, I kept following up with these ten people. Three of them responded and we made the deal happen. Five of them said nothing. They still ignored me. And two of them told me to piss off and that it’s unprofessional what I do.” And then compare that with your prior results where you didn’t follow up with any of those ten people and you generated zero.

Maybe in your world if you’re looking at those numbers and you say, “Well, if I piss off two people and three people make business with me, that’s still not good because I don’t want to piss off anyone.” If that’s the case in your business and in your market then that’s an unusual situation.

In my opinion, if I can get three deals out of ten I would lose even if I piss off somebody, that’s fair. And you know what? If somebody is pissed off by you following up, I really truly question that person. I mean don’t follow up 48 times in a day. But if you follow up like today, three days later, a week later, two weeks later in email and somebody is getting upset about that, in my mind honestly, fuck them.

Hiring the right type of salesperson

So let’s take the next one. And I really truly appreciate the question. I think it’s a really, really, really important question so I’m really happy that you’re asking it, Julia. So the next follow up question that you have on that is, “We want to hire…” it’s not really – well, it’s partially a question like how do you hire someone that’s like me? All right. So that’s a tough question. That’s a question like how do you hire the right type of salesperson.

I don’t know. It’s tough. It’s tough like anything else out there. First, you might not just want to look for “salespeople” with a sales career but look at anyone and everyone out there that’s persistent, that has a high tolerance level for pain and rejection. You want to look for certain personality traits. And a minority of people out there has it even if they are not in sales. Just go in and look at anyone out there that you know that’s kind of the most like me in that sense. Maybe it’s a cousin, maybe it’s your grandfather.

Anyone and everyone goes. It doesn’t have to be somebody professional in your market. Anyone that you know that’s really persistent, that’s really not afraid of rejection, that’s really hustling and ask them who else they know that’s really out there and hungry and hustling and then ask them and just referrals, you get to know more and more of these type of people and you’re going to be able to find somebody that eventually and hopefully you can get to join your team.

Yeah, there you go. Vasa has a good tip. Just reject everyone and the people that keep persisting might be the right people to join your team. That’s not a bad piece of advice.

Get a free copy of The Ultimate Startup Guide to Outbound Sales and more!

All right. So here are a few goodies before we do more Q&A and you guys keep the questions coming. First of all, I’ve written a book for outbound sales for startups. There’s a discount quote for 50% but I don’t feel like giving a 50% discount quote today. Let’s make it 100% discount quote. I want to give you this book for free if you don’t have it. If you already have it, I’ll give you something else. Just shoot me an email at Steli@Close and I’ll find a goodie for you. Maybe I’ll send you some chocolate. Maybe I’ll send you something else. Send me an email, Steli@Close and I’ll give you some little gift as a piece of appreciation for free to get things rolling.

Also, just two weeks ago, I launched something completely new. If you go to “” and put in your email address, what you can get is every morning, a 1-minute video from me giving you quote as well as action item to help you motivate yourself and help you crush your sales day.

We have thousands of people already on the email list. People seem to love it. Please make sure to check it out, “”. Put in your email and every morning, seven days a week, forever, I’m going to send you a 1-minute video to motivate you and help you and inspire you for your day.

And then last but not least, if you are a fan of podcasts and you want to not just hear myself coming from a startup and sales perspective but listening to the opposite end of the spectrum, somebody that’s more introverted, somebody that’s smarter than me and more experienced and somebody that’s coming from the marketing and sales perspective, go to “” and make sure to subscribe to our podcast.

It’s Hiten Shah, co-founder of KISSmetrics and Crazy Egg and myself chatting about business and life. We are very tactical from like how to do sales and marketing for your startup and how to create content. We’re talking about topics that almost nobody ever talks about like how do you deal with death when you’re in a startup? What were our darkest moments as entrepreneurs? Like we talk about some real deep shit that you don’t hear a lot about out there so, make sure to check it out if you haven’t already.

All right. Let’s keep going with Q&A time. So we have another 10 minutes. If you want to – if you’ve got everything you needed out of this webinar and you want to go back to crushing it, go ahead and crush your day today and have an amazing time. If you have more questions and want to discuss things, just put your question in chat. I’ll go through them one by one. I’ll hang out at least for the next 10 minutes and answer as many questions as I can.

Q&A section

All right. Let me go scroll up and see what’s the first question or comment I can pick up on. Here you go. Vasa says she gives the interns the book to read in their first week. That’s not a bad idea. We have tons of customers that their whole onboarding process with new sales hires is they give them the book, they give them a bunch of follow up talks and webinars and content to read and they put together kind of a training plan based on the content that we generated. Not a bad idea.

Hey Miles, I appreciate the kind words about the podcast. You are awesome. I really appreciate it.

How do you reach the decision-makers in large organizations?

All right. So here’s a question from Miles. Any best practices for triangulating on the decision-maker within large organization? Is the question here, how do you get to the decision-maker in large organizations? How do you get to that person?

In figuring out who the right decision-makers, yes. So yes, I do have some – I do have one simple hack. There are many. But I’ll share one of the more popular and more successful ones. This is another book. If you guys haven’t read Predictable Revenue by Aaron Ross, you might want to go out there and get that book.

But here is a simple tactic. What you can do if you are approaching large organizations and you want to find the right person in there, what you want to do is you want to reach out very, very high in the ladder and ask for a referral down.

So what do I mean by that is you can go and email the CEO or the CMO like some super senior high level executive in that org. There’s a quick email that you can write that just basically is, “Can you put me in touch with the right person or point to the right direction?” And in that email, all you say is, “Hey, dear CEO, what we do in a sentence is X, Y, Z. I think this would be an amazing fit for your company. Can you put me in touch with the person that’s responsible for X, Y, Z? Thank you so much.”

And you will be amazed. On average, 30 to 40% of the time, you will get a very high level executive to actually connect you with somebody down the line in the org chart. And once you get a referral down from the org chart, once the CEO sends an email that says, “Yes, John is our project manager about this and he should be the right person.”

Your chances of a) now knowing who the right person is but also then getting that person’s attention is dramatically higher. There’s a whole book that revolves around this tactic and strategy. It’s called Predictable Revenue. And Aaron Ross really wrote it, break through an email. It’s an email that uses that template. That template has been used and propagated many, many times in many different ways. It’s very simple. It’s basically just like, “Hey, here’s what we do. Here’s the right person to talk to.” It’s very, very simple. So that can be an effective way to get to somebody in a large organization. So take that as a tip.

All right. Next question. So you figure out the right decision-maker. Next question from Jonathan, best copy follow up for driving users to sign up for trials. Jonathan, is the question, how do we get someone that we interacted with to now sign up for trial if they haven’t already? Please clarify the question out. I’ll try my best to answer it. I just want to make sure that I answer the right question.

What’s the best way to find phone numbers for people listed in lead databases?

In the meantime, I’ll just go to the next question. Amit says, “What’s the best way to find phone numbers for people who probably only have emails for” I don’t know my man. I mean this is a tough one. Phone numbers is tough. Yes, you can get – you can go to something like or Hoovers or something like database site and try to buy the phone number. You need to just have realistic expectations., I don’t know the exact and most up-to-date numbers but last time I used it and the last time I heard about it from other people, 30 to 40% of the data in those databases is obsolete or late.

Like think about it. Somebody puts in a contact in and they get a credit which allows them to get a contact for free. A lot of people do this. But these people now, you have their business card and you put it in and that person has moved on to a different business or different position. So a high quantity of the data that you can get at those databases is just wrong. So you need to just account for that. You need to just know, “If I buy 100 phone numbers on, 30 to 40 of them will not be correct anymore.” Just keep that in mind.

All right. I don’t have a good way. Like you can – like there’s no beautiful perfect way to get people’s accurate phone numbers out there. It’s a lot like buying the data, guesswork. There’s a bunch of things that you can do that are hacks but nothing is really great.

Which CRMs should small businesses use?

All right. Let me see what the next question is. So Ron is asking, “I think Close might be overkill for my situation. I’m a solo founder. I’m hustling. I do what I can. Do you have any advice on CRMs for us tiny businesses? I’m struggling a bit to keep all of my outreach efforts coordinated.”

Ron, I mean my man, if you’re too small for Close, just try out whiteboard or a spreadsheet and keep it simple. If you are reaching out to tons and tons of businesses and you send hundreds of emails, you make hundreds of cold calls, you might want to consider Close. If not, an alternative to just pay attention to just have like a super lightweight CRM that’s living in your inbox could be Streak, S-T-R-E-A-K. It’s a Gmail plugin. You might want to check it out. It might be – if a whiteboard or a spreadsheet is not complex enough then Streak might be your next best option before Close. Check it out.

Aaron is asking – oh, Aaron is telling Ron, “Hey, I use Insightly. It’s very user-friendly. Always adding new features.” Yup, I heard good things about them.

How to use cold email to drive trial sign-ups?

All right. So mostly – so Jonathan is clarifying the original question. Mostly cold but qualified audience first interaction, meaning cold emails to drive their call-to-action to sign up for the trial. I don’t know, my man. I don’t know Jonathan, if writing cold emails. If the conversion you want to accomplish in a cold email can be to get somebody to sign up for a free trial. Usually the cold convince – I have seen where people send cold emails trying to get people to sign up for a free trial had been bad.

Now, if you wanted to do that and you wanted to give people some kind of an incentive to do it now and not later. So you want to just send them an email and go, “Hey, just today, it’s expiring tomorrow, you will get a 60-day free trial versus a 40-day free trial if you sign up with this specific link. It’s expiring in two days.” Like you would want your email to say something that incentivizes people to take action right the fuck now because if you send me an email and you go, “Hey, this is what we do. I think it would be a really cool product. Here’s a link to allow you to do a free trial.” I’m just going to go, “Oh cool! I’ll check it out later.”

So, I don’t know if I would use a cold email to get people to sign up for a trial. If I try to do that, I would make sure that there’s some incentive, there’s some urgency in it.

All right. Let me see next question. So what do we got here? All right. Nigel is giving out some shout out to Close. I appreciate that. Saying, “It’s great guys. It does most of the data entry for you and it’s twice the price. Just do it.” My man, I appreciate it. And we have thousands of customers, all of them are seeing immediate results and jumps in terms of their close rate, in terms of the quantity and quality outreach they do and as a result, the deals they closed. So yeah, check it out.

If you need anything or if you have any feedback regarding Close, send me an email, directly to me, Steli@Close and let’s chat.

How to follow up with professionals?

All right. Amit says, “We deal mainly with professional teachers. Do you have examples of tone down more professional follow up than the funny biz example?” Amit, just don’t be funny. Just in your email, just go – let’s say you send a follow up email and you just say, “Hey, it was great talking to you the other day. When can we talk this week?”

And they don’t reply to you, all I want you to do is to reply to that email and go, “Hey, how about this Tuesday or Thursday at 3:00 or 4:00 PM?” If they don’t reply to you, all I want you to do is reply to that original email and go, “Hey, I hope you’re doing well. How about this Wednesday? What would be a good time?”

If they don’t reply to you, all I want you to do is reply and go, “Hey, how about next week this or that time?” That’s it. That’s all you need to do. Clean cut, simple. Just keep offering times, keep following up. You don’t have to be funny. You don’t have to be funny in a way that’s cool for teachers. Just don’t be funny.

Is ToutApp or Yesware better for email campaigns?

All right. Next question. All right. So Miles, so another question. “ToutApp or Yesware for app on email campaigns? Unless you’re using something else than Close, which I would like to learn more about, we started with Yesware but running into some issues with their tech.” Yeah. I mean both Yesware and ToutApp are cool. If you are running into issue with Yesware, chances are that ToutApp is going to create similar or even worse issues. I hear better things about Yesware than ToutApp to be honest in general.

We are using something else for Close. There’s a third party app that’s developed to be able to utilize Close to do the exact same things as with Yesware and ToutApp. Miles, just shoot me an email at Steli@Close and I’ll let you know about it and we’ll talk about this offline some more.

What are the best strategies for combining inbound marketing and outbound sales?

All right. Next question. Sid is asking, “Steli, just wondering what your thoughts are on the best strategies for combining inbound marketing and outbound sales?” Let me deliberate on that question a little bit. So what my thoughts are on combining inbound marketing and outbound sales? I don’t know. I don’t really know what you mean. I mean we – so Close is all inbound marketing. Like all we do is we create tons and tons of content. It’s word of mouth and content that gets people to us. And once they signed up, we send people tons of emails. We call our sign-ups. We sell them once they are in our funnel. But we are not doing any outbound sales. We are not reaching out to people.

If you want to combine inbound and outbound marketing and sales, I mean one thing that you might want to do is just in your outbound sales, use your content if it’s really fucking good. So, you might want to be doing – if you know that your content is so – like our content is good enough that we know if you start reading our blog and our content, within three to six months, you’re going try Close. So sooner or later, you are going to try our product once you are in our content funnel.

If you know that, you might want to do outbound campaign where instead of just trying to sell them immediately to your product, you sell them on your content first. So you reach out to people and you send them an ebook, a whitepaper, or a webinar link. You make them subscribe to your blog or something else. You get them to connect to an article and then you get them into you content machine and eventually, they’ll turn into an inbound lead. That might be kind of a strategy that you want to use in combining content marketing and outbound sales.

But besides that, I don’t know. I think inbound marketing and inbound sales is one group, outbound sales is another. So yeah, I don’t know exactly how you would combine those two. Let me know if you have any follow up to that question or my little rant, random rant about it.

All right guys, we are actually running out of time. I need to jump off to another call. I hope this was useful and valuable. Please shoot me an email, Steli@Close. Let me know about feedback about the webinar if you liked it or not, what could be done better. Let me know if you have any other questions we were not able to address in this webinar. And if at any point, there’s anything I can do to help, reach out and let me know. It’s my honor and pleasure. Until then, go out there and crush them!

When doing cold outreach emails in which you link to a piece of content, should you send them to a landing page or directly to the content?

Oh, before I let you guys go. I saw Ron has one last question. Let me quickly address that before I jump off to my next call. All right Ron, let’s quickly do this. When doing cold outreach emails in which you include a link to a piece of good content, should you send them to landing page or send them to the content directly?

It depends. It’s a good question but it depends. It depends what kind of content it is. It depends how good that content – that organic content pitch converts. If you have a lot of like opt-in options and your general let’s say, blog post page converts really well then just send them to that. If you don’t, then you might want to have kind of a gated page.

But usually, you have to think about it. If you are reaching out to somebody cold, they didn’t ask you for that email. They didn’t ask you about your company. They are not interested. You don’t want to gate the content. You don’t want to say, “Hey, I really think you should read this.” And they click on something that’s a landing page that says, “Give me some information before you can get to the content.” So you want to make sure that it’s un-gated. Besides that, I don’t know. You want to maybe A/B test the landing page versus the organic blog post page and see what converts better.

All right guys. Go out there and crush them. Have an amazing day and talk to you very soon.

Get ahead of the game by grabbing your free copy of The Follow-up Formula.

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