How to Follow Up with Sales Prospects in 2024 [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? 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 must push past the fear of rejection and half-hearted maybes to get results.

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

Transcript

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 life and entrepreneurship. Suppose 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 daily. I measure this by the feedback I get every day from people emailing me the amazing results they were able to generate by amplifying 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 as to why I care about the follow-up. I’ve been a serial entrepreneur my whole life. I’m completely unemployable. I never had a real job.

And my entrepreneurial superpower 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, and get people to join the company.

More recently and more relevant to this topic, I started a company called Elastic Sales. 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.

In the process of selling for so many different companies, we learned a thing or two about selling and selling well, especially for startups and new companies. We utilized the power of follow-up to create outsized results and returns for our clients.

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

Close was originally called our secret sauce and was just meant for internal purposes and use. Still, 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 calling us, 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 to us that the software we built was pretty powerful, and they wanted it. Eventually, in January 2013, we decided to release the software and launched Close, which we thought was a parallel small business compared to our big services business.

What ended up happening was that Close grew so fucking fast that within a year, it was a bigger business than Elastic, and we fully focused on it.

Today, Close is an 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.

This means if you do 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. The group was led by a master hypnotist who is probably one of the best hypnotists in 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. These people are all experts in communication and have really interesting personalities, and we’re traveling through Southeast Asia together. It’s a pretty wild adventure.

One day, we arrived at a little town. We wanted to go to the ocean and rent a little boat to get to one of the most southern islands in Thailand, Ko Lipe. It’s a beautiful, tiny island, and probably there are about 30 people living on it. We were super excited to go to this little jewel on the ocean.

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

So here we are, 20 guys and gals, 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 getting barbecued in the sun.

And all of a sudden, there’s a lady on a bike, and she sees us. She sees a group of people who appear to be tourists, and she is biking over to us. And at the back of the bike, she has like a little stand with fruits on it.

So, she bikes her bike with a mobile fruit stand in front of us. She jumps off the bike and starts approaching us with a big smile, saying, “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, smile, nod, and go, “Yes, thank you so much, but we had just lunch, and we’re so full and no thanks. We’re not in the market for fruit right now.”

So, she 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. 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 approaches us again, “Fruit, fruit, fruit, fruit.” We all started laughing again, “Ha ha ha! Yes, we can see that it’s fruit. We get it. We appreciate your hustle, but thanks, but no thanks. We’re so full we don’t need any fruit.”

Eventually, the master hypnotist comes out of the building again 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 would be over in 10 minutes, and we could start getting 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 all buy fruit from her.

An hour later, we’re on a boat, a little boat, a shaky boat, all the way to this little island, and we’re all eating fruit, looking at each other and going, “Fruit! This was an amazing idea.”

This fruit seller lady knows the secret of the follow-up hustle. 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? The person with the highest clarity in the room always wins, and the most persistent person always wins.

Here is one of my favorite quotes from Paul Graham. If you’re into startups, do 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

I’ve told this story plenty of times, but I will summarize it again for those who haven’t heard it before. When people want me to tell them what kind of 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, “Yes, I’m happy to meet. This sounds interesting.”

I respond, and I go, “Oh, this is so exciting. How about meeting on Tuesday or Thursday at this or that time?” Silence. I send another email. Silence. Another email. Silence.

Forty-eight emails later. Do 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 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 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 many 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 and 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 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. What kills most startups is that they live in a zone 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 and outcomes, yes or no.

I 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 stop following up.

If you just follow this simple rule, I guarantee you I’ll bet you any amount of money you want; 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 people this? 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 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 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 can’t take the silence anymore, 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. We all have egos, and our egos want us to look great, 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 will address what I told that billionaire. How many times have I emailed him in a second? 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 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 respond.” You make up some fucking story in your mind. I’m not a mind reader. I don’t make stories up in my mind.

Do you know my hypothesis 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 their highest priority.

And that’s fine with me. I will 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 putting together a book. It will contain hundreds of stories of people making magic happen by following my follow-up advice. I’ll share a few of them here in the middle with you guys to increase your belief in this and make you realize 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, 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!”

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

Here’s another case study. “Steli’s philosophy on following up sent me back to the 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 onboarding this month as a customer.”

I could go on and on. People tell stories about how they got press articles, investors, and customers or convince somebody to join the company. You will create magic in this world if you just keep following up until you get a result—it's 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. 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. 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 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 or a day or two later.

Then, the next follow-up is two or three days later, a week later, two weeks later, and then a month later. And then after that, maybe every month, maybe every two months, and eventually, if it 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 broaden and space it out over time.

With this billionaire, I was probably very, very, very insistent, and I emailed him multiple times every week for several weeks. And also, I’ll get to for – and I’ll get to what I was telling him, but it’s 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 frequently 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 is that it’s very unintrusive.

So, it allows the person to either read it or not, respond to it, delete it 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, which is 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 frequency and the longest period of time. So you can send somebody 48 emails over a few months. That’s totally fine. It’s very aggressive, but it’s fine.

But with email—email allows you to do the highest level of frequency over the longest period of time, but it’s the least urgent channel. 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 trying to accomplish with this person is more urgent, you must 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 a phone call.

So if you call me, that’s a lot more interruption in my day. If you call me or 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 are way too aggressive.

So what you want to do is if you don’t have an urgent matter, 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 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 sleep you or archive or delete you. I have to acknowledge you.

So, in-person follow-up is the most disruptive channel. 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 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. He shared a story once where they were working on a multimillion-dollar deal for months and months and months, and then, in the final few days of the deal, they got an email from the customer saying, “You know what? We’re 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. The next day, they showed up at that prospect's and customer’s office and said, “Hey, we saw your email. We were in New York anyway and thought we’d drop by and just say hi. Sadly, it didn’t work out, but we thought we might have a chat.”

What happened? They were invited in, sat down, and chatted. 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, a 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 person or via email—and saying, “Hey, I’m in the area. Can I buy you some lunch, dinner, or coffee?”

Or just showing up at the office and saying, “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 discuss the do’s and do n’ts of following up, which relate to what I did and said when I followed up with that billionaire. The number one thing is that you need to be friendly and keep it short.

So, honestly, my follow-up emails lack any and every piece of creativity. All my emails sounded like, “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 refer 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 my 47 emails, I thought I would 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 met 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, cut, and friendly. Keep it short. Provide value and shut the fuck up. Just keep it moving; it's very, very simple.

I have people sometimes who 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 got a message from him on Facebook: "Hey Steli, I’m a big fan. I really need your advice about X, Y, and Z.” two hours later, they sent me a follow-up message on Facebook and started complaining that I haven’t answered yet.

They’ll go, “Oh, Steli, it’s outrageous that you haven’t responded yet. Do you think you are the 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. Perhaps 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 who approaches me with this level of aggressiveness and neediness and tries 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. Keep it clean-cut, friendly, 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 indefinitely, ‎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 no one else is running. You are going to win.

If I can convince you to do that, we have 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, 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're already a pro at the follow-up game, yes, let’s talk about what to do next. My answer to the question of whether you should follow up when somebody tells you no is that it depends.

It depends on how big and how valuable the conversation relationship could be for you and them and for your business in the long term. Many times, people have responded to a no, followed up with another no, and then turned it into a yes.

I know about some 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.

I know people who got a no, and then they sent that person a gift, and it was maybe—I don’t know. One story was in Canada, and the guy sent the person a hockey stick with a little quote card that said, “You will lose 100 percent 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. A little quote said, “Hey, this article inspired me.

After getting your rejection, I was crushed. Then I read this article, and it inspired me. I hope it will inspire you, too.” They called that person a day later and said, “Did you read the article? I just wanted to make sure you got it.”

The person was laughing and saying, “Yes, this was really creative and really cool.” And they started 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 who will follow up even when they get a NO, but I think that it depends on the relationship, what you’re selling, the value that you’ve created for both sides and how up your game you are 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 you do with cold emails.

What do you do when you are reaching out to somebody cold who has never heard of you, who never talked to you in person, on the phone, or via email, and who never responded or replied positively in any shape or form or way? What do you do 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?

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

But then again, I know people who have a company in the UK that provides SEO services. They have been following up with me. I’ve been ignoring them for the past three years. And they have probably followed up about 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 startups. So I’m like, yeah, I get it. I don’t need SEO services right now, so I will archive this. But I’m not deleting this. I’m not even annoyed by it. I respect their hustle and 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 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 and how aggressive you are. But I would not follow up indefinitely with a cold contact. We follow up typically eight times with a cold outreach. That’s probably a good rule of thumb.

The Breakup 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, such as breaking 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 response rate to these emails. It’s going to be very, very successful.

Most of the time, I 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.

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 several 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.

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. Many of the biggest and most successful B2B SaaS businesses use 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 same email from HubSpot, 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, you say, “Hey dude, I’ve been trying to reach you multiple times over this period. I never heard back from you.

So what I need to do right now is assume that you don’t care about this anymore. I’m going to take you off my list. You will never 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 don’t want it that much, and you will make it more valuable. So, in the breakup email, you tell him, “Hey, I’m going to stop emailing you. You will not hear from me again. If you want something, if you are interested in this topic, you can contact me anytime, but I’m taking you off my list.” It’s money. That email is killer. It gets insane open rates and insane reply rates. So use it at your own discretion and wisely.

Now again, for the follow-up ninjas, what’s the response? 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 percent when you have “Goodbye from Steli” in the subject line. It’s going to get very high open rates.

The response rate really depends on the quality of the list and 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 percent response rates, which is insanely high for a group of people that have ignored your prior 7, 8, 9, or 10 emails.

I’m sure there are companies that are much lower, some companies even higher than what I say. But I’m telling you, out of all the emails that you sent us, this is probably one of the emails that gets 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 who 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 who runs a business that basically coaches people in business to be more funny. He sent me an email one day and said, “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 sent me another email with some funny thing going on: “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 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 GIFs. One is of a haywire that’s going through an empty town, and there’s something else. It’s just some funny GIFs 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 send me a video. He says, “Hey, Steli, since you’re not replying to funny GIFs or 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 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, two guys show up with guitars and 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 thought, “Oh, all right. This is much better than what I thought.”

Then I’m thinking, “How did they do this?” And I think, “They are not – they did not just do this for me.”

So now I’m thinking, “Oh, they created this follow-up to the 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 edit the second part where he does the generic song.” I’m wondering how he scaled 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 think 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 like, “Hey, Steli, now I’m concerned about whether you’re still alive. 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.

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

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

The reason why I show you this is to show you how you can be a little creative. By the way, if you want to use any kind of GIF, 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 who 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: "Hey, what do you do when you are serving super-conservative and very professional customers?”

You probably need to speak in a tone 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 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, seven of them hate me, 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 equally indifferent above me and we created zero value, made nothing happen, and 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, are about creating value and making things happen. So, I’m not optimizing to be liked. I’m not optimizing for not being convenient to other people. I’m optimizing to create value.

So, maybe 48 follow-ups are too many for your audience, and this is probably true for many audiences. Maybe 4, 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 number of follow-ups 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 do 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 an 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 truly appreciate the question. I think it’s an important question, so I’m thrilled 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 like me? All right. So that’s a tough question. That’s a question: 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 who’s persistent and has a high tolerance level for pain and rejection.

You want to look for certain personality traits. And a minority of people have 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 you know that’s persistent, that’s not afraid of rejection, that’s really hustling and ask them who else they know that’s 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. You’ll 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 who persist 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, I’ve written a book for outbound sales for startups.

There’s a discount quote for 50 percent, but I don’t feel like giving a 50 percent discount quote today. Let’s make it a 100 percent 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.

Email me 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 a little gift for free as a piece of appreciation to get things rolling.

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

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

And then last but not least, if you are a fan of podcasts and you want not just to hear me 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 “thestartupchat.com” and make sure to subscribe to our podcast.

It’s Hiten Shah, co-founder of KISSmetrics and Crazy Egg, and I'm chatting about business and life. We are very tactical, 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 you deal with death when you’re in a startup. What were our darkest moments as entrepreneurs? Like, we talk about some really 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 for the next 10 minutes and answer as many questions as possible.

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 whose 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, Thank you for the kind words about the podcast. You are awesome. I appreciate it.

How Do You Reach the Decision-Makers in Large Rrganizations?

All right. So here’s a question from Miles. Are there any best practices for triangulating the decision-maker within a large organization? The question here is, how do you get to the decision-maker position in large organizations? How do you get to that person?

Yes, I do have some—I do have one simple hack—for figuring out who the right decision-makers are. There are many, but I’ll share one of the more popular and 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 on the ladder and ask for a referral down.

So what 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. A quick email you can write is, “Can you put me in touch with the right person or point me in 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 contact the person responsible for X, Y, and Z? Thank you so much.”

And you will be amazed. On average, 30 to 40 percent of the time, you will get a very high-level executive to connect you with somebody down the line in the org chart. Once you get a referral down from the org chart, 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) knowing who the right person is and getting that person’s attention are dramatically higher. There’s a whole book that revolves around this tactic and strategy. It’s called Predictable Revenue.

Aaron Ross wrote it, breaking through an email. It’s an email that uses that template. That template has been used and propagated many times in many different ways. It’s very simple.

It’s 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. Jonathan's next question is about the best copy follow-up for driving users to sign up for trials. Jonathan, how do we get someone we interacted with to sign up for a trial if they haven’t already? Please clarify the question. I’ll try my best to answer it. I 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 Data.com?”

I don’t know my man. I mean, this is a tough one. Phone numbers are tough. Yes, you can get it – you can go to something like Data.com or Hoovers or a database site and try to buy the phone number. You just need to have realistic expectations. Data.com, I don’t know the exact and most up-to-date numbers, but the last time I used it and the last time I heard about it from other people, 30 to 40 percent of the data in those databases is obsolete or late.

Like, think about it. Somebody puts in a contact in Data.com, and they get a credit, which allows them to get a contact for free. A lot of people do this. But these people now have their business cards, and you put them 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 Data.com, 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 and guesswork. There are 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 to keep all my outreach efforts coordinated.”

Ron, I mean, my man, if you’re too small for Close, just try out a whiteboard or a spreadsheet and keep it simple. If you are reaching out to tons and tons of businesses, sending hundreds of emails, and making hundreds of cold calls, you might want to consider Close.

If not, an alternative to just pay attention to have 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 and always adding new features.” Yup, I heard good things about them.

How Do You Use Cold Email to Drive Trial Sign-Ups?

All right. 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 you are writing cold emails.

Suppose 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 people send cold emails trying to get people to sign up for a free trial, which has 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 email them 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.”

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 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 tried to do that, I would make sure that there was some incentive and urgency in it.

All right. Let me see the next question. So what do we get here? All right. Nigel is giving a 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.

We have thousands of customers, and all of them are seeing immediate results and jumps in terms of their close rate, in terms of the quantity and quality of outreach they do, and, as a result, the deals they close. So yeah, check it out.

If you need anything or have any feedback regarding Close, email me directly at 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 toning down more professional follow-up than the funny biz example?” Amit, just don’t be funny. Just go in your email – 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?”

If they don’t reply to you, all I want you to do is reply to that email and say, “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 say, “Hey, I hope you’re doing well. How about this Wednesday? What would be a good time?”

If they don’t reply, 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 and keep following up. You don’t have to be funny. You don’t have to be funny in a cool way 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 other than Close, which I would like to learn more about, we started with Yesware but ran into some issues with their tech.”

Yeah. I mean, both Yesware and ToutApp are cool. If you are running into issues with Yesware, ToutApp will likely create similar or even worse issues. I hear better things about Yesware than ToutApp, in general.

We are using something else for Close. There’s a third-party app that’s been developed 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. Then, 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 asks, “Steli, what are your thoughts on the best strategies for combining inbound marketing and outbound sales?” Let me deliberate on that question a little bit. So, what are my thoughts 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. All we do is create tons and tons of content. It’s word of mouth and content that gets people to us. Once they sign up, we send tons of emails to people. We call our sign-ups. We sell them once they are in our funnel. But we are not making 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 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 will try our product once you are in our content funnel.

If you know that, you might want to do an 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 your content machine, and eventually, they’ll turn into an inbound lead. That might be a strategy that you want to use to combine content marketing and outbound sales.

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

All right, guys, we are running out of time. I need to jump off to another call. I hope this was useful and valuable. Please shoot me an email at Steli@Close. Let me know your feedback about the webinar, whether you liked it or not, and what could be done better.

Let me know if you have any other questions we could not address in this webinar. 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 That 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 sending cold outreach emails in which you include a link to a piece of good content, should you send them to a landing page or to the content directly?

It depends. It’s a good question, but it depends. It depends what kind of content it is. It depends on how good that content—that organic content pitch—converts. If you have a lot of 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 a gated page.

But usually, you have to think about it. If you are contacting 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 think you should read this.” They then click on 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.

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