Labcast: The Three Sales Habits to Break

Listen in as speaker, author and strategist Dan Waldschmidt stops in to discuss what he thinks are the three sales practices that should be put out to pasture. Dan took a timeout from his popular blog, Edge of Explosion, to talk about the bad techniques that too many salespoeple still fall prey too and offer tips for breaking the habit.

Episode 28: Three Sales Habits to Break


Corey O’Loughlin: This is Labcast, insights and ideas for the expansion-stage
senior manager, hosted by OpenView Labs.

Thanks for joining us for this episode of Labcast. Today’s
podcast is guest hosted by Devon Warwick, Sales Analyst from
OpenView Labs. Her guest is Dan Waldschmidt, author of the blog
“At the Edge of Explosion,” and they will be discussing three
sales habits that all salespeople must try to break now. We hope
you enjoy it.

Devon Warwick: Today we here with Dan Waldschmidt. Thank you, Dan, so much for
being here today.

Dan Waldschmidt: Thank you for having me.

Devon: Dan, in early April, you released a blog series on bad sales
habits that we are addicted to. I thought today, for the
purposes of our podcast, we could capitalize on three of these
bad habits. I’d like to kick off the discussion with talking
about this phrase “always be closing.” What are your thoughts on
that? Why is it a bad habit?

Dan: Yeah, so the idea of “always be closing,” it’s one of those phrases
that’s kind of cheeky, and it would be more De Niro-esque if he
was actually in the movie. But it’s one of those movie lines
that we kind of repeat to ourselves as if everyone automatically
gets it and cares. So the idea of “always be closing” is the
fact that, no matter what you do, you’re always asking sentences
that end with the possibility of someone saying, “All right. I
will buy your stuff.” Usually it’s in that tone of voice, with
mild to more than mild annoying ring to it.

But the problem with it is it might only work for a one call
close. Might. But it certainly doesn’t work for any additional
revenue you want to get from customers. Sales stats have shown,
over the last 10,000 years that we’ve been humans, that the
first time you close a customer, it’s probably not the lifetime
revenue you’re going to get from that customer. When you buy a
car from a dealership, you’re probably going to buy multiple
cars from the dealership if you live that same area.

So the “always be closing” line just kind of smacks of 1960s
rhetoric. So I think a better alternative is what I mentioned in
there – always be caring and collaborating. So when you care
about a customer, it comes through. So a customer sees that.
They know that, and they want to do business with you.

Then collaborating. Sometimes it’s not even about you making
revenue. It’s just about you trading ideas. Problem solving with
a buyer, you’re not charging them anything, right? You’re just
helping them out. Then when it does come time to take the
revenue, down the road, because that is the end game, we do need
revenue, is that you’ve created this collaboration where they’re
the first person you’re going to come to.

Devon: Yeah, I think it’s actually particularly relevant with a lot of
the companies that we invest in, which are SaaS models, software
as a service.

Dan: Yeah.

Devon: So, you close that deal you’re closing, but a month down the
road, two months down the road, they unsubscribe.

Dan: Yeah, that’s right. Yeah, that’s a big problem. Getting them back
after they unsubscribe, it’s like getting your girlfriend back
after you’ve cheated on her or something like that. Not that I
have any experience with that. That illustration came out way
too fast.

But, I mean, it’s just really hard to do, right? Like you’ve
burned their trust and you’re done. It’s like you’re dead to
them. A lot of times, it’s just maybe annoying newsletters we
send. It’s a series of things where we just seem like our
relationship isn’t enough, we want more. So yeah, that whole
“always be closing” thing is really damaging, actually.

Devon: Yeah, I would agree. The second habit that I would like to talk
about today is the concept of I and we. Can you expand on that
at all, Dan?

Dan: So, if we look at our e-mails that we’re sending, a lot of them are
things like, “I just wanted to check in on you” or “We have a
great product.” “We have a great team.” “I wanted to reach out”.
If we look at our e-mails, it’s all I’s and we’s.

One way to eradicate this problem, and I helped a company, one
of the rules we set in place, it was a fireable offense to start
any e-mail without the word you in it. So the opening word for
every e-mail had to be you. You had to invent a way to start
every e-mail with the word you. But it’s almost like you asked
me to follow up with you in a week. Boom, you’re into it.

It’s like we need a spam filter for our emotions, and we’re very
needy people. Without safeguarding ourselves, we start going I
and we and me, and it really kind of oozes out of us. So we kind
of have to go, whoa, whoa, cycle that back in in, and let’s make
it about you. The easiest way . . .

Devon: Right. If only there was a tool, right, that could point out
how many times you’re saying I, me, my in your e-mails, just
highlight them. Wouldn’t that be interesting?

Dan: Yeah, it would be. There’s actually a product, and now that I’m on
the spot I can’t think of it, but it spots passive aggression in
your e-mails.

Devon: No way.

Dan: It’s an Outlook plug-in. I don’t use Outlook, but I did bookmark it.
I’ll have to send it to you later. But it spots passive
aggressive words. If we set some basic principles like that,
like that’s an idea for your companies. Start every e-mail with
the word you. No e-mail more than five sentences long. Start
every e-mail with the word you.

All of a sudden, it gets you thinking. What does the other
person want? Not what you want to say, not what you want to
close them by, but you. You had a problem with X. You were
concerned about your servers not working right. Our product
helps work them right. You were going to make a decision by the
end of the month, where do you stand?

All of a sudden, in our minds, it’s like wow, cha-ching. We’re
now focusing on the other person. Talk about selfishness, it’s
instantly like the selfishness antidote.

Devon: One thing I had heard you mention previously was not starting
off an e-mail asking a question.

Dan: Mm-hmm.

Devon: Because you want to put your question at the end of the e-mail.

Dan: Yeah.

Devon: You don’t want to start off your little spiel by asking them
something. I think that’s a great point, because I think so many
of us kick it right off with, “How are you doing? What’s our
plan for the next step?” Then go into another five sentences of
what they’re actually really trying to get there on the instant

Dan: Yeah, that’s right. That’s right. I think most of what I’ve learned
as I try to stay with that four to five sentence e-mails, is
that . . . a lot of times when we write e-mails, we try to add
like back story to it. Like, “Last time we spoke, there were
three main issues, and they were blah blah blah.” They know
that. They may not remember it perfectly, but you can delete
that out.

So if you really hold yourself to the five sentence rule, I’m
only going to have the five most relevant sentences, what you
find yourself cutting is like back story. It’s like a big thing
that you cut out of it, which is actually the next thing on the
list was writing too long of e-mails. It’s like a perfect segue
into this.

We talked about this earlier, but we’re reading more e-mails on
mobile devices now than ever before in the history of mankind,
since the caveman days. Mobile devices are the in thing. It’s
just, when you think about a busy executive in an airport,
heading to train, heading to a meeting, even in a setting like
this, you’ve got your mobile devices out. We’re sending these
long books.

So four to five sentences. Some brief stats on long e-mails is
that an executive, statistically, Exact Target tells us they are
only going to spend 15 to 20 seconds acting on an e-mail. I
mean, that’s reading your e-mail and then deciding if they’re
going to act on it.

Devon: The subject line too. I mean, especially with a mobile device,
that’s the first glimpse that the prospect’s going to get at
your e-mail.

Dan: ExactTarget said that 73% of the people who mark your e-mail as spam
didn’t even open it up. They just looked at the From line and
the Subject line. So I think, for me sometimes, when I’ll send
something, like if I was coming up to Boston, I may go
Boston/Speaking/Dinner or something like that where it’s like
okay I think Dan wants to talk about Boston and dinner and
something like that.

So you have the key points in your subject line. Also one
mistake that people make, which is crazy, is the From is like
“Do Not Reply” It’s like, okay, you’re pretty full of
yourself to send me an e-mail and then say don’t reply. It’s
like I’m having a discussion where my son goes, “I don’t want to
do that.” I go “Don’t talk back to me.” You know what I mean?
It’s like, okay, Mr. eBayer, I’m using eBay as an example
because I just got one from them recently like that.

But instead of saying “Do Not Reply,” why
not change it to something like, “Important information from
eBay.” Something that’s emotionally intelligent.

Devon: Something so simple. Like you said, it’s the little things.

Dan: Yeah. Do not reply. Like, “I’m going to send you an e-mail but do not
talk back to me over e-mail.”

Devon: Now here you are, ranting about it on a podcast. Thousands of
people are going to be listening to this.

Dan: Yeah, I’m 32 years old, I will talk back to you. How dare you tell
me not to talk back? Or like our From is Admin or From is Info.
Like really? Really?

Devon: Boring.

Dan: It’s not even boring. Boring is exactly right, but it’s more than
that. It’s like uninspiring. It’s like I don’t want to talk to
an admin. I want to talk to Devon. I don’t want to talk an info.
I want to talk to you. So put that in there. Make me feel warm
and fuzzy, like there’s a real person back there.

What’s silly about this Devon, it’s a five-second fix, if that.
It’s like changing the From line. Another thing you can do in
the From line, I used to do this more and I stripped it out, but
I would do like Dan Waldschmidt and then a pipe, space pipe, and
then my phone number. So in the From, it was Dan Waldschmidt and
then it was my phone number. So if you needed to respond me,
then all you had to do was . . .

Devon: Yeah, I saw that on your e-mail response. It’s pretty clever

Dan: Just things like that. I’ve changed it up a few times just to get the
right fit. I used to have my URL in there too. But that way, if
you have a lot of people, like Outlook and Gmail automatically
save people you’re e-mailing or people who’ve e-mailed you to
the address book. So now in your address book, even if you don’t
have my phone number, it’s in my name. Little tips and tricks
like that can help you create better conversations with people.

Devon: You started off the list of terrible ideas with “checking in.”
What does that mean exactly?

Dan: My mom used to say if you can’t do something brilliant, try not to do
something stupid, which is kind of like how this is. The
checking in thing is kind of funny when we think about it,
because we sit down and write an e-mail and we say “Hey Devon,
Dan here. Just checking in with you, seeing where you’re at with
your decision.” What we really want to say is, “Hey Devon, are
you still going to buy from me and when?”

But we can’t say that, or we don’t feel like we can say that. So
instead we go, “Hey, I’m just checking in with you.” Then the
buyer, potential buyer, gets this e-mail that says I’m just
checking in with you, and it’s like well I’m not your mom, I’m
not your guardian. Heck I’m not even your friend and you’re
checking in with me. Leave that to Foursquare or something like

It’s just a little bit ironic. Another way to say it, it is
comical to say to a potential buyer, “Hey I’m just checking in
with you.” Here’s why. Buyers care about themselves. Even I care
about me. I care about me. I don’t have time to care about you
checking in with me. So from an emotional standpoint, it’s
really way off the mark. Even if we leave out the emotions,
there’s really no call to action in those e-mails. It’s usually
like, “Hey, I’m checking in with you, looking to see when we’re
going to move forward with your order.” The whole thing is
passive aggressive. Right?

Devon: Right. There’s not one question in there. It’s just statements.

Dan: It could all be summed up, once again, if we went back to the
principle of starting every e-mail with the word you, it’s, “You
were looking forward to getting started with our product. I
haven’t heard from you in a while. Is there anything I can do to
help you?” That’s even still not as direct as we could be. We
could just say something like, “You expressed an interest in my
product and expressed to me that you were going to be able to
make a decision in the next week or two. Have you been able to
make a decision?” Or, “Are you going to go forward with my

So there’s no reason to check in at that point. We can go
direct. So there’s no reason to do all of this passive
aggression or these kind of really fluffy, we’re not really sure
what we’re supposed to . . . I get that e-mail and I go, “You’re
checking in with me?”

Devon: Instant stress. I’m not going to lie. I’ve sent them myself.
But I’ll think twice next time. But it’s something that’s
comfortable, right? You might say that with your friends or,
you’re right, maybe even your mom, you know, just checking in.
You can’t do it with the buying/selling relationship. It’s just
not going to work.

Dan: It’s one of those things where with all of these items, it’s like I
do these things. I wrote the list. I still do these things. I
think the key thing is when you see it, it’s like a little alarm
bell. Like when you send an e-mail that’s longer than five
sentences, I may do it, but the alarm goes off to say hey this
may not be the best use of communicating with the customer. This
is one of those.

If you find yourself sending an “I’m just checking in with you”
e-mail, it’s not in the world. Just know that your sales process
is screwed up. So then just fix it.

Devon: Thank you so much for being here today, Dan. For more
information, those of you who are interested in reading this
blog in its entirety, you can check out the link that is listed
in the podcast description. Also be sure to check out my blog at

Lis­ten to more pod­casts from the Open­View Labs team.

Corey O'Loughlin
Corey O'Loughlin

Corey was a marketing analyst at OpenView from 2010 until 2011. Currently Corey is the Owner of Prep Obsessed and was previously the Marketing Manager at MarketingProfs.
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