Dear Friends,

Master the two line email.

It’s short, sweet, and gets a response.

Best Regards,



Assume the Damn Sale

Unless your product sucks people want to buy it. The idea that if you come into a conversation assuming the sale you are “playing hardball” or “going in for the kill” drive me up a wall. Why the hell would we be having a conversation with a prospect if they weren’t either A) Mildly Interested or B) A damn good fit for our product (in the case of a cold-call).


In my humble opinion if, in the sales conversations you are having with a prospect, it feels like you are trying to convince them of something it is not going to end well. You need to bleed confidence in your product. These people are coming to you because you offer the solution to their problem. They need what it is that you have, and all you are doing is making sure your product delivers. There is nothing sleazy, nothing unethical about this practice. Your confidence is transferrable, and when the prospect feels that they are infinitely more likely to move forward.


Assume the damn sale!

Who the hell still uses Internet Explorer anyway?

“I swear to God Barbara if you tell me one more time that you followed my directions exactly I’m going to drive across the country and snap your laptop in half. If you followed my directions we’d have fixed this problem by now…and by the way…. who the hell still uses Internet Explorer?”


Customer support can be a real joy, but unfortunately it is arguably the most important part of any successful sales position. In today’s era of instant gratification it is even more important that customers be able to either resolve their issues on their own, or with as few phone calls or emails as possible. This is where you need to be on the offensive. If you don’t have a procedure in place for how you are going to handle the vast majority of problems that are going to come up the probability of losing clients just because they can’t get an issue resolved will skyrocket.


Being able to collect as much information from your clients as quickly and efficiently as possible when your clients have an issue will prevent you from having to go back and forth with them multiple times. I promise you that if they have to send you more than 2 or maybe 3 emails your client will be pissed. Apart from this you also need to either be an expert in troubleshooting whatever you’re selling, or be able to get them in touch with an expert immediately.


If you can’t fix your own problems you’ve already lost.


Clients: Your unofficial sales team

I occasionally catch some flak for the amount of time that I spend dealing with current customers instead of prospecting for new ones. However, I am telling you right now that this is hands down the best way to maximize your sales. If I receive any type of inbound contact from a current client my goal is to get them an answer within 20 minutes. If that is completely impossible I try for an hour, with the very last resort being the end of the day. If this cuts deeply into prospecting, which it certainly does on the busiest of days, then so be it.

Here’s my philosophy: The people buying your product don’t know crap about it. It’s your job to make sure they get what they need as soon as they need it otherwise your product becomes useless. If you think about every client this way you might start to better understand the importance of instant feedback. We live in a society where we have almost every answer to every question we could ever have at the tips of our fingers. If you don’t blend seamlessly into that same model you are going to struggle.

So what if you don’t spend 2-3 hours a day prospecting. I sure as hell don’t and you know what…my average sale is 3x the size of company average. You want to know the reason for that? Most of them come from current clients. Because these people know that I am going to get back to them right away with an answer to their problem they come to me before consulting the Google. Think about the power in that. Apart from now having monstrous upsell and add on sale opportunities think about what happens when these folks get together with their colleagues and talk about work. Whose name do you think is going to be top of mind for all of my clients?

When your clients prospect for you your job gets a whole lot easier.

Budget Issues

Client: “Welllll…..I just don’t know if we’ve got room in our budget for this next year.”

              Snarky: “Sure, I understand. Times are tight, cutbacks are happening. *silently* …I mean maybe cut down on the 47 legal pads you blow through in a month and try writing on both sides of the page for once Jimmy…*aloud* so how do you plan on moving forward to solve problem x?”

              Client: “We aren’t really sure yet. We are considering various options.”

              Snarky: “Well, why don’t you just let us handle everything. Soup to nuts. We’ve got this great product you might be interested in that builds on what you currently have. Cost is 3x what you’re paying now. But…are you ready for this magic? If you buy 3x we will give you your original product for free!”

              Client: “Hmmm…that is interesting…send over a proposal and I’ll get back to you.”

**1 Week Later***

              Client: “Snarky! Sign me up for 3x! We love it! But the original product is still free right?”

              Snarky: “Well…if that’s what it’s going to take…you got it Jimmy.”


People just want free stuff. It is truly incredible to me the lengths that some people will go to feel like they’ve gotten something for nothing. I want to know where all that extra cash miraculously came from! Are the growing it in the backyard? Now…it is obviously important to make sure that the product delivers on that value, but I promise you that budget issues are very rarely budget issues. You’ve just got to be creative.

Good Touch, Bad Touch

Why the hell haven’t you responded to my email Judy? You’ve opened it 17 times, Salesforce tells me so! I mean I know you didn’t come back to it or forward it to your co-workers just for kicks and giggles. “Hey guys, check out this completely uninteresting, spammy email I just got!” Said nobody ever…

Does this drive anybody else nuts? If I see that an email gets more than 3 opens I cannot help but check in on this prospect obsessively. But does this mean I should reach out? The unfortunate answer is: maybe. As a general rule of thumb I won’t drastically increase or decrease my usual outreach based on email opens. At the risk of seeming totally creepy I try and avoid anything that indicates too strongly “oh by the way…I know what you’ve been clicking ;)”

What I will do, however, is hang on to a prospect a little longer than usual if they are consistently coming back to old outreach. Maybe try and mix in an additional phone call or two, or potentially try and get in touch with someone else in the organization who might have decision making power.

Unfortunately there is no good benchmark for how many touches are going to be necessary to close a sale. I had two prospects finally close last week. The first had 5 touches starting Oct 1. The second had 87 freaking touches starting Sept 15. There aren’t even 87 days in that stretch of time!

The takeaway? Some prospects are cool with Netflix and chill, and others wont put out for anything less than the Surf n’ Turf. How badly do you want it?

The Value of Being Liked

You want to know the secret to customer retention? Be nice. I mean damn, is it that hard for people to understand?

Do you want your retention rate to be over 90% where industry average is 75%? Half the battle, in fact I would say almost all the battle, is making sure that your customers like you. This doesn’t mean that they have to invite you over to their house for dinner, but you also don’t want them rolling their eyes every time your number shows up on their phone.

As long as your product is good why the hell should your customers go anywhere else? I hate to break it to you, but you’re probably the reason why! Think about this tomorrow as you go through your day. Are you smiling while you talk to prospects or clients? Does your voice inflection change? Do you laugh? If the answer is “no” I promise you the person on the other end of the call isn’t enjoying it either.

You know why my retention rate is better than yours? People like me better than you.