Envelope-to: andrew@sterlingcal.com
Delivery-date: Fri, 15 Aug 2025 11:04:04 -0500
Content-Type: multipart/alternative; boundary=0fc44c6b0b8b6e17ec90552f12363d11e89ddd46eae1478323daca2c7491
Date: Fri, 15 Aug 2025 16:03:52 +0000 (UTC)
From: Collin Stewart <predictablerevenue-newsletter@mail.beehiiv.com>
Mime-Version: 1.0
Message-ID: <DZY7cs6KSfeLqaxWVuIDmQ@geopod-ismtpd-5>
Subject: Why Your "Sure Thing" Deals Slip
Reply-To: Collin Stewart <collin@predictablerevenue.com>
Feedback-ID: 
 =?us-ascii?Q?f7d00ab9-1f08-4b81-a05f-98118378d58b=3Anewsletter=3A3c5b97ff-00a9-?=
 =?us-ascii?Q?4acc-916d-c137bca24b1d=3A23270855726497d?=
sId: 3c5b97ff-00a9-4acc-916d-c137bca24b1d
To: "andrew@sterlingcal.com" <andrew@sterlingcal.com>

--0fc44c6b0b8b6e17ec90552f12363d11e89ddd46eae1478323daca2c7491
Content-Transfer-Encoding: quoted-printable
Content-Type: text/plain; charset=utf-8
Mime-Version: 1.0

Hello Andrew,=20

_**Book update**__: I had to go back to square one with the audiobook edito=
r, they didn=E2=80=99t do a great job so I decided to start over. I=E2=80=
=99ll hopefully have them to share later this month.  _

**_Pre-order benefits_**_: For anyone that pre-orders the book, I have a mo=
nthly zoom call where we work on revenue problems plus you get access to th=
e Investor list I shared a few weeks back. I have something interesting com=
ing next week or two and you=E2=80=99ll get that too once it=E2=80=99s live=
=E2=80=A6 _

_You can order the _[_book here_](https://www.amazon.com/Terrifying-Art-Fin=
ding-Customers-Sleep-Deprived/dp/1774586134)_. Email me your receipt and I'=
ll add you to the event/share the sheet. _

Ok, now onto the newsletter.

_The deals you're most excited about? They're often the ones that crash and=
 burn._

I learned this the hard way with a $600,000 Olympic security contract. I ha=
d the PO, had verbal approval from four different organizations, had 76 gen=
erators sitting in a yard ready to deploy. Then got the call: "Sorry, we're=
 not going to do it."

That one still stings. But it taught me something important about enterpris=
e deals: they're unpredictable as hell, and the stuff that kills them is us=
ually hiding in plain sight.

The Vancouver Olympics were coming up, and there was real concern about sec=
urity after the London tube bombing and 9/11. They wanted to test all the s=
ecurity systems ahead of time, but couldn't get 220-volt power to the remot=
e locations in time. So I organized 76 generators from across Canada to pro=
vide temporary power for a two-week testing period. We had everything lined=
 up, contracts signed, generators sitting in the yard ready to deploy.

Then they called and said they'd run out of time to do the testing properly=
. They were just going to wing it during the actual Olympics. Six hundred t=
housand dollars, gone. My boss gave me a 2% consolation prize from the $60k=
 consulting fee we negotiated for our trouble. I was livid. But that deal t=
aught me more about enterprise sales than any course ever could.

## Why Big Deals Really Stall

Been thinking about this after a client call this week. Their pipeline is l=
ooking strong=E2=80=94multiple six-figure deals moving forward, champions e=
ngaged, verbal commitments. But I've seen this movie before.

Big deals typically stall because you missed something. It could be a holid=
ay with a key buying influence, a requirement that's really a deal killer, =
or an influencer with a competing project. When all you're focused on is gi=
ving your demo, you're not spending enough time asking the real questions t=
hat will de-risk the deal and find the things that will stall or kill it.

Most sales reps fall into the demo trap. They get excited when a prospect s=
ays "show me what you've got" and rush straight into product mode. But what=
 they should be doing is digging deeper. Who else needs to see this? What h=
appened to the last vendor you evaluated? What would make this project not =
happen? What other priorities are competing for budget this quarter?

The stuff that kills deals is rarely about your product. It's about timing,=
 politics, budget cycles, and personalities. Your champion gets promoted an=
d their replacement has different priorities. The CFO decides to freeze all=
 new spending. A key stakeholder goes on sabbatical right when you need the=
ir approval. Someone in procurement has a relationship with your competitor=
.

Every unknown in your deal is basically 100% risk. The more unknowns you ha=
ve, the more likely you are to get that "sorry, we're not moving forward" e=
mail. This is why I've become obsessed with what my friend Megan Wilson (on=
e of the best enterprise closers I know) calls "de-risking deals." Every pi=
ece of information you gather, every process step you understand, every sta=
keholder you identify removes a bit of that risk.

The problem is most of us treat sales like we're fortune tellers. We look a=
t a deal and make up a probability based on gut feel. "This one feels like =
80%." But what if there's a technical requirement you don't know about? Wha=
t if your champion doesn't actually control the budget? What if they're pla=
nning a hiring freeze next quarter? Your 80% might actually be 20%.

Even deals with verbal commitments can disappear overnight. I've seen it ha=
ppen more times than I can count. Your champion gets fired. Budget prioriti=
es change. A competitor comes in with a relationship you didn't know about.=
 The company gets acquired and all purchasing decisions get frozen. Wild st=
uff happens in enterprise sales, and the bigger the deal, the more opportun=
ities there are for things to go wrong.

## Two Things That Actually Help

**Ask About Their Timeline (But Do It Right)**

On your second or third call, ask: _"When do you ideally want to have somet=
hing like this in place?"_ Not "when do you want to buy?" Just when they wa=
nt the problem solved. This question is magic because it gets them thinking=
 about their own process=E2=80=94what approvals they need, when budget cycl=
es hit, if anyone's going on vacation.

You'll learn more from this one question than from three discovery calls. T=
hey'll start thinking out loud about all the steps that need to happen. "We=
ll, we'd need to get it through security review first, and Jennifer handles=
 that but she's going on maternity leave in October. And then legal would n=
eed to look at it, which usually takes about six weeks. Oh, and we can't im=
plement anything new in Q4 because of the product launch."

Suddenly you understand their real timeline and all the potential roadblock=
s. You're not selling to them anymore=E2=80=94you're helping them solve a l=
ogistics puzzle. This one question reveals the decision-making process, the=
 stakeholders involved, the budget cycle, and potential timing conflicts. I=
t's the difference between hoping for the best and actually understanding w=
hat needs to happen.

But here's the key: you have to actually listen to what they tell you. When=
 they mention that Jennifer handles security review, ask about Jennifer. Wh=
en do you need to get this to her? What does she typically look for? Has sh=
e killed deals before? When they mention the Q4 implementation freeze, dig =
into that. Why the freeze? Who decided that? Are there any exceptions?

**Use a Mutual Action Plan**

Sounds fancy, but it's just a shared project plan before they're a customer=
. Once you know their timeline, work backwards. When do we need to finish t=
he trial? When does this need to go through legal? When do we need budget a=
pproval? Who needs to sign off at each step?

Put it in a simple spreadsheet with owners and dates. Include things like "=
Security review completed by Jennifer" and "Legal approval received" and "B=
udget confirmed with finance team." Share it after they're engaged (never o=
n the first call=E2=80=94that's weird).

The beauty is you're not pushing them to buy. You're helping them figure ou=
t their own process. You become their sherpa, not their vendor. And when th=
ings start to slip, you can point to the plan and say, "Hey, we agreed Jenn=
ifer needed to finish the security review by the 15th. Should we push every=
thing back a week, or is there another way to handle this?"

I got this idea from Tom Williams at Clari Align when I had him on my podca=
st. He's the head of their sales collaboration platform and has been thinki=
ng about this stuff for years. He even shared a template, which I'll dig up=
 and send to anyone who replies to this email asking for it. The whole conc=
ept is about lowering risk through collaboration=E2=80=94not just with your=
 champion, but with everyone involved in the buying process.

The mutual action plan works because it forces everyone to be honest about =
what actually needs to happen. No more vague "we'll probably sign next quar=
ter" conversations. Instead, you have specific milestones with specific own=
ers and specific dates. When someone says they can get budget approval "soo=
n," you can look at the plan together and say, "Okay, if we want to go live=
 by January 15th, we need budget approval by December 1st. Does that work w=
ith your finance team's schedule?"

Tom's approach goes beyond just timeline planning though. He maps the stage=
s to the buyer's journey instead of your sales process. What do they need t=
o educate themselves about? How do they validate vendors? What jobs do they=
 need to get done internally? Then you build the plan around helping them a=
ccomplish those things, not just hitting your sales milestones.

_Reply with the word MAP and I=E2=80=99ll share Tom=E2=80=99s template._

## Your Next Move

Pick one thing to try this week. Ask that timeline question on your next ca=
ll and really listen to what they tell you about their process. Sketch out =
a simple action plan for your best deal=E2=80=94just a list of the steps th=
at need to happen and when. Start tracking where your champions go when the=
y change jobs.

The deals you're most excited about will probably crash and burn. The ones =
that sneak up on you become your biggest wins. My client's biggest deal thi=
s quarter came from a guy they thought had gone dark months ago. He just re=
-engaged out of nowhere because his priorities changed and suddenly the pro=
blem became urgent.

Focus on the process, not counting the money. Every deal teaches you someth=
ing about how these things really work. Even the ones that blow up in your =
face=E2=80=A6 Especially those ones.

_Hit reply if you've got a deal that went sideways in a weird way. I love h=
earing these stories.=C2=A0_

Collin=C2=A0

PS - reply back with MAP if you want the mutual action plan template from T=
om Williams - I'll dig it up and send it over.


=E2=80=94=E2=80=94=E2=80=94

You are reading a plain text version of this post. For the best experience,=
 copy and paste this link in your browser to view the post online:
https://foundersedition.co/p/why-your-sure-thing-deals-slip

--0fc44c6b0b8b6e17ec90552f12363d11e89ddd46eae1478323daca2c7491
Content-Transfer-Encoding: quoted-printable
Content-Type: text/html; charset=utf-8
Mime-Version: 1.0

<!DOCTYPE html><html lang=3D"en" xmlns=3D"http://www.w3.org/1999/xhtml" xml=
ns:v=3D"urn:schemas-microsoft-com:vml" xmlns:o=3D"urn:schemas-microsoft-com=
:office:office" style=3D"font-size:16px;"><head></head><head><meta charset=
=3D"utf-8"/><!--[if !mso]><!--><meta http-equiv=3D"X-UA-Compatible" content=
=3D"IE=3Dedge"/><!--<![endif]--><meta name=3D"viewport" content=3D"width=3D=
device-width,initial-scale=3D1"/><meta name=3D"x-apple-disable-message-refo=
rmatting"/><meta name=3D"format-detection" content=3D"telephone=3Dno,addres=
s=3Dno,email=3Dno,date=3Dno,url=3Dno"/><meta name=3D"color-scheme" content=
=3D"light"/><meta name=3D"supported-color-schemes" content=3D"light"/><titl=
e>Why Your &quot;Sure Thing&quot; Deals Slip</title><!--[if mso]><xml><o:Of=
ficeDocumentSettings><o:AllowPNG/><o:PixelsPerInch>96</o:PixelsPerInch></o:=
OfficeDocumentSettings></xml><![endif]--><style>
  :root { color-scheme: light; supported-color-schemes: light; }
  body { margin: 0; padding: 0; min-width: 100%!important; -ms-text-size-ad=
just: 100% !important; -webkit-transform: scale(1) !important; -webkit-text=
-size-adjust: 100% !important; -webkit-font-smoothing: antialiased !importa=
nt; }
  .body { word-wrap: normal; word-spacing:normal; }
  table.mso { width: 100%; border-collapse: collapse; padding: 0; table-lay=
out: fixed; }
  img { border: 0; outline: none; }
  table {  mso-table-lspace: 0px; mso-table-rspace: 0px; }
  td, a, span {  mso-line-height-rule: exactly; }
  #root [x-apple-data-detectors=3Dtrue],
  a[x-apple-data-detectors=3Dtrue],
  #MessageViewBody a { color: inherit !important; text-decoration: inherit =
!important; font-size: inherit !important; font-family: inherit !important;=
 font-weight: inherit !important; line-height: inherit !important; }
  span.MsoHyperlink { color: inherit !important; mso-style-priority: 99 !im=
portant; }
  span.MsoHyperlinkFollowed { color: inherit !important; mso-style-priority=
: 99 !important; }
  .a { background-color:#FFFFFF; }
  .b { background-color:#007b8a; }
  .c  { background-color:#FFFFFF; }
  .d { background-color:#b4d9d8; }
  .d2 { background-color:#FFFFFF; }
  .d3 { background-color:#FFFFFF; }
  h1 a { text-decoration:none;color:#0079ad;font-style:italic; }
  h2 a { text-decoration:none;color:#0079ad;font-style:italic; }
  h3 a { text-decoration:none;color:#0079ad;font-style:italic; }
  h4 a { text-decoration:none;color:#0079ad;font-style:italic; }
  h5 a { text-decoration:none;color:#0079ad;font-style:italic; }
  h6 a { text-decoration:none;color:#0079ad;font-style:italic; }
  h1, h1 a, h2, h2 a, h3, h3 a, h4, h4 a, h5, h5 a, h6, h6 a, ul, li, ol, p=
, p a { margin: 0;padding: 0; }
  h1 { font-family:'Trebuchet MS','Lucida Grande',Tahoma,sans-serif;font-we=
ight:400;font-size:28px;color:#2A2A2A;line-height:42px;padding-bottom:4px;p=
adding-top:16px;mso-margin-top-alt:16px;mso-margin-bottom-alt:4px }
  h2 { font-family:'Trebuchet MS','Lucida Grande',Tahoma,sans-serif;font-we=
ight:400;font-size:24px;color:#2A2A2A;line-height:36px;padding-bottom:4px;p=
adding-top:16px;mso-margin-top-alt:16px;mso-margin-bottom-alt:4px }
  h3 { font-family:'Trebuchet MS','Lucida Grande',Tahoma,sans-serif;font-we=
ight:400;font-size:20px;color:#2A2A2A;line-height:30px;padding-bottom:4px;p=
adding-top:16px;mso-margin-top-alt:16px;mso-margin-bottom-alt:4px }
  h4 { font-family:'Trebuchet MS','Lucida Grande',Tahoma,sans-serif;font-we=
ight:400;font-size:18px;color:#2A2A2A;line-height:27px;padding-bottom:4px;p=
adding-top:16px;mso-margin-top-alt:16px;mso-margin-bottom-alt:4px }
  h5 { font-family:'Trebuchet MS','Lucida Grande',Tahoma,sans-serif;font-we=
ight:400;font-size:16px;color:#2A2A2A;line-height:24px;padding-bottom:4px;p=
adding-top:16px;mso-margin-top-alt:16px;mso-margin-bottom-alt:4px }
  h6 { font-family:'Trebuchet MS','Lucida Grande',Tahoma,sans-serif;font-we=
ight:400;font-size:14px;color:#2A2A2A;line-height:21px;padding-bottom:4px;p=
adding-top:16px;mso-margin-top-alt:16px;mso-margin-bottom-alt:4px }
  p { font-family:'Montserrat','DejaVu Sans',Verdana,sans-serif;font-weight=
:400;color:#2c3e50;font-size:16px;line-height:24px;padding-bottom:12px;padd=
ing-top:12px;mso-margin-top-alt:12px;mso-margin-bottom-alt:12px; }
  p a, .e a, ul a, li a, .h a, .h2 a, .h3 a { word-break:break-word;color:#=
0079ad !important;text-decoration:none;font-style:italic; }
  p a span, .e a span, ul a span, li a span { color: inherit }
  p .bold { font-weight:bold;color:#2c3e50; }
  p span[style*=3D"font-size"] { line-height: 1.6; }
  .f p { font-size:12px;line-height:15px;color:#2c3e50;padding:0; }
  .f p a { color:#2c3e50 !important; }
  .g p { font-family:'Helvetica',Arial,sans-serif;font-size:14px;line-heigh=
t:20px;font-weight:normal;margin:0; }
  .g p a  { text-decoration: underline; }
  .i p { font-family:'Helvetica',Arial,sans-serif;line-height:23px;font-siz=
e:15px;color:#2D2D2D; }
  .i p a { color:#2D2D2D !important; }
  .i2 p { font-family:'Helvetica',Arial,sans-serif;line-height:23px;font-si=
ze:15px;color:#2D2D2D; }
  .i2 p a { color:#2D2D2D !important; }
  .i3 p { font-family:'Helvetica',Arial,sans-serif;line-height:43px;font-si=
ze:24px;color:#2D2D2D; }
  .i3 p a { color:#2D2D2D !important; }
  .h p a { color:#595959 !important; }
  .h2 p a { color:#595959 !important; }
  .h3 p a { color:#595959 !important; }
  .f p a, .i p a, .i2 p a, .i3 p a, .h p a, .h2 p a, .h3 p a { text-decorat=
ion:underline; }
  .j { border-top:3px solid #b4d9d8; }
  .k p { padding-left:15px;padding-bottom:0px;padding-top:6px;mso-margin-to=
p-alt:6px;mso-margin-bottom-alt:0px;mso-margin-left-alt:15px; }
  .o { background-color:#FFFFFF;border:1px solid #F1F1F1;border-radius:5px;=
 }
  .o p { font-family:'Helvetica',Arial,sans-serif;padding:0px;margin:0px; }
  .l p,
  .l p a, .l a { font-size:14px;line-height:20px;font-weight: bold;color:#2=
D2D2D;padding-bottom:6px;mso-margin-bottom-alt:6px;text-decoration:none; }
  .m p,
  .m p a { font-size:13px;line-height:18px;font-weight:400;color:#2D2D2D;pa=
dding-bottom:6px;mso-margin-bottom-alt:6px;text-decoration:none; }
  .n p,
  .n p a { font-size:12px;line-height:17px;font-weight:400;color:#2D2D2D;pa=
dding-bottom:6px;mso-margin-bottom-alt:6px;text-decoration:none; }
  .p { background-color:#FFFFFF;max-width:520px;border:1px solid #E1E8ED;bo=
rder:1px solid rgba(80, 80, 80, 0.3);border-radius:5px; }
  .q { font-size:16px;font-family:Helvetica,Roboto,Calibri,sans-serif !impo=
rtant;border:1px solid #e1e8ed;border:1px solid rgba(80, 80, 80, 0.3);borde=
r-radius:10px;background-color:#FFFFFF; }
  .q p { font-size:16px;font-family:system-ui,Helvetica,Roboto,Calibri,sans=
-serif !important;color:#222222;padding:4px 0; }
  .r { border:1px solid #E1E8ED !important;border-radius:5px; }
  .s p { font-size: 14px; line-height: 17px; font-weight: 400; color: #6978=
82; text-decoration: none; }
  .t p { font-family:'Helvetica',Arial,sans-serif;font-size:12px;line-heigh=
t:18px;font-weight:400;color:#000000;font-style:italic;padding:4px 0px 0px;=
 }
  .v { border-radius:10px;border:solid 0px #f5bf83;background-color:#f5bf83=
;font-family:'Montserrat','DejaVu Sans',Verdana,sans-serif;color:#FFFFFF; }
  .v a { text-decoration:none;display:block;color:#FFFFFF; }
  .w p { font-size:12px;line-height:15px;font-weight:400;color:#FFFFFF; }
  .w p a { text-decoration: underline !important;color:#FFFFFF !important; =
}
  ul { font-family:'Montserrat','DejaVu Sans',Verdana,sans-serif;margin:0px=
 0px 0px 25px !important;padding:0px !important;color:#5e5e5e;line-height:2=
4px;list-style:disc;font-size:16px; }
  ul > li { font-family:'Montserrat','DejaVu Sans',Verdana,sans-serif;margi=
n:10px 0px 0px 0px !important;padding: 0px 0px 0px 0px !important; color: #=
5e5e5e; list-style:disc; }
  ol { font-family:'Montserrat','DejaVu Sans',Verdana,sans-serif;margin: 0p=
x 0px 0px 25px !important;padding:0px !important;color:#5e5e5e;line-height:=
24px;list-style:decimal;font-size:16px; }
  ol > li { font-family:'Montserrat','DejaVu Sans',Verdana,sans-serif;margi=
n:10px 0px 0px 0px !important;padding: 0px 0px 0px 0px !important; color: #=
5e5e5e; }
  .e h3,
  .e p,
  .e span { padding-bottom:0px;padding-top:0px;mso-margin-top-alt:0px;mso-m=
argin-bottom-alt:0px; }
  .e span,
  .e li { font-family:'Montserrat','DejaVu Sans',Verdana,sans-serif;font-si=
ze:16px;color:#2c3e50;line-height:24px; }
  .rec { font-family:  ui-sans-serif, system-ui, -apple-system, BlinkMacSys=
temFont, "Segoe UI", Roboto, "Helvetica Neue", Arial, "Noto Sans", sans-ser=
if, "Apple Color Emoji", "Segoe UI Emoji", "Segoe UI Symbol", "Noto Color E=
moji" !important; }
  .rec__button:hover { background-color: #f9fafb !important; }
  .copyright a {color: inherit !important; text-decoration: none !important=
; font-size: inherit !important; font-family: inherit !important; font-weig=
ht: inherit !important; line-height: inherit !important;}
  .txt_social p { padding: 0; word-break: break-all; }
  .table, .table-c, .table-h { border: 1px solid #C0C0C0; }
  .table-c { padding:5px; background-color:#FFFFFF; }
  .table-c p { color: #2D2D2D; font-family:'Helvetica',Arial,sans-serif !im=
portant;overflow-wrap: break-word; }
  .table-h { padding:5px; background-color:#F1F1F1; }
  .table-h p { color: #2A2A2A; font-family:'Trebuchet MS','Lucida Grande',T=
ahoma,sans-serif !important;overflow-wrap: break-word; }
  @media only screen and (max-width:667px) {
    .aa, .w100pc { width: 100% !important; }
    .bb img { width: 100% !important; height: auto !important; max-width: n=
one !important; }
    .cc { padding: 0px 8px !important; }
    .ee { padding-top:10px !important;padding-bottom:10px !important; }
    .ff ul, .ff ol { margin: 0px 0px 0px 10px !important;padding: 0px !impo=
rtant; }
    .ff li { margin:10px 0px 0px 10px !important; }
    .r {height:140px !important;}
    .s p { font-size:13px !important;line-height:15px !important; }
    .mob-hide {display:none !important;}
    .mob-show {display: block !important; width: auto !important; overflow:=
 visible !important; float: none !important; max-height: inherit !important=
; line-height: inherit !important;}
    .mob-stack {width:100% !important;display:block !important;}
    .mob-w-full {width:100% !important;}
    .mob-block {display:block !important;}
    .embed-img {padding:0px 0px 12px 0px !important;}
    .socialShare {padding-top:15px !important;}
    .rec { padding-left:15px!important;padding-right:15px!important; }
    .bodyWrapper { padding:10px 4px 10px 4px !important; }
    .social-mobile {float:left !important;margin-top:10px !important;}
  }
  @media screen and (max-width: 480px) {
    u + .a .gg { width: 100% !important; width: 100vw !important; }
    .tok-heart { padding-top:75% !important; }
    .tok-play { padding-top: 250px !important; }
  }
  @media screen and (max-width: 320px) {
    .tok-heart { padding-top:65% !important; }
  }
  .u { border: 1px solid #CACACA !important; border-radius: 2px !important;=
 background-color: #ffffff !important; padding: 0px 13px 0px 13px !importan=
t; font-family:ui-sans-serif,system-ui,-apple-system,BlinkMacSystemFont,"Se=
goe UI",Roboto,"Helvetica Neue",Arial,"Noto Sans",sans-serif !important;fon=
t-size: 12px !important; color: #767676 !important; }
  .u a { text-decoration: none; display: block !important; color: #767676 !=
important; margin: 0px !important; }
  .u span, .u img { color: #767676 !important;margin:0px !important; max-he=
ight:32px !important;background-color:#ffffff !important; }
</style><!--[if mso]><style type=3D"text/css">
    h1, h2, h3, h4, h5, h6 {font-family: Arial, sans-serif !important;}
    body, table, td, p, a, span {font-family: Arial, sans-serif !important;=
}
    sup { font-size: 100% !important;vertical-align: .5em !important;mso-te=
xt-raise: -1.5% !important;line-height: 0 !important; }
    ul { margin-left:0px !important; margin-right:10px !important; margin-t=
op:20px !important; margin-bottom:20px !important; }
    ul li { margin-left: 0px !important; mso-special-format: decimal; }
    ol { margin-left:0px !important; margin-right:10px !important; margin-t=
op:20px !important; margin-bottom:20px !important; }
    ol li { margin-left: 0px !important; mso-special-format: decimal; }
    li.listItem { margin-left:15px !important; margin-top:0px !important; }
    .paddingDesktop { padding: 10px 0 !important; }
    .edm_outlooklist { margin-left: -20px !important; }
    .embedImage { display:none !important; }
</style><![endif]--><style>
        @font-face {
          font-family: 'Montserrat';
          font-style: normal;
          font-weight: 400;
          font-display: swap;
          src: url('https://fonts.gstatic.com/s/montserrat/v24/JTUSjIg1_i6t=
8kCHKm459WlhyyTh89Y.woff2') format('woff2');
        }

        @font-face {
          font-family: 'Montserrat';
          font-style: italic;
          font-weight: 400;
          font-display: swap;
          src: url('https://fonts.gstatic.com/s/montserrat/v24/JTUQjIg1_i6t=
8kCHKm459WxRyS7m0dR9pA.woff2') format('woff2');
        }
</style></head><body class=3D"a" style=3D"margin:0px auto;padding:0px;word-=
wrap:normal;word-spacing:normal;background-color:#FFFFFF;"><div role=3D"art=
icle" aria-roledescription=3D"email" aria-label=3D"email_name" lang=3D"en" =
style=3D"font-size:1rem"><table role=3D"none" width=3D"100%" border=3D"0" c=
ellspacing=3D"0" align=3D"center" cellpadding=3D"0" class=3D"gg"><tr><td al=
ign=3D"center" valign=3D"top"><table role=3D"none" width=3D"670" border=3D"=
0" cellspacing=3D"0" cellpadding=3D"0" class=3D"aa" style=3D"width:670px;ta=
ble-layout:fixed;"><tr><td class=3D"bodyWrapper" align=3D"center" valign=3D=
"top" style=3D"padding:10px 5px 10px 5px;"><table role=3D"none" width=3D"10=
0%" border=3D"0" cellspacing=3D"0" cellpadding=3D"0" align=3D"center"><tr><=
td align=3D"center" valign=3D"top" style=3D"border-width:0px 0px 0px 0px;bo=
rder-style: solid; border-color: #FFFFFF;border-radius:10px 10px 0px 0px;ba=
ckground-color:#FFFFFF;" class=3D"c"><table role=3D"none" width=3D"100%" bo=
rder=3D"0" cellspacing=3D"0" cellpadding=3D"0" align=3D"center"><tr id=3D"h=
eader"><td style=3D"padding:15px 15px 0px 15px;"><div style=3D"padding-top:=
0px;padding-right:0px;padding-bottom:20px;padding-left:0px;"><table role=3D=
"none" width=3D"100%" border=3D"0" cellspacing=3D"0" cellpadding=3D"0" alig=
n=3D"center"><tr><td class=3D"f" align=3D"right" valign=3D"top"><p> August =
15, 2025 &nbsp; | &nbsp; <a href=3D"https://link.mail.beehiiv.com/ss/c/u001=
.r7o6LfRLXwQ-3g4cvdmKtd8SJB4D4z2stBRrWAMoYsgzdkPstelHgSfySiH86utEKZIEKq97xn=
LV3ETfW2M34IoThJ6FZQK91j2okb740jgGhy6phJ__zxIm9Cm4i92IUS0ybcrl-FzKNZIaJl2rc=
JnwT13Y63NlTfvdj_OB8UHmrGbtpLcqi3swN95IHQ-uwiPB83kFBD7fl1y6u-nYmF0P1chiaQNZ=
-iMo725EbbbGIr8ot57FB8VKh5bL8Uel_uZlyhEjeewdlv6rqY8tScwsuoeJoAO4B2miBLVbnFI=
xqRWg7spwZcvOaYEZOM47uM1EV93Viab9JEHvcalT9Um5cz7BJtYzHoNVkkwii6hCzLpHOnoLFE=
mvxnnqZGJr3x6r4fwm1kwrknKpQh6IF3C5iG-mrtDaBp-qvXG-GsPmzxKsC_kucFZDGs-dlS92Y=
X5kryGJYKbPm3hiFw3R9muERIFK2yMMt5FwxRcuewJJOQD4o1xR2uOv2tw-uPGuF0ereURr0NYq=
Tm3dr1iV8ETB4b0MPESgrVvPhBKSlNbh0OMv_IEuJMkClaX-0uarRsMrIzrNyMx3tL5952txDTZ=
baYrU7W5s3Ds1JjO7qWP0KVM3QwFMblopiSOz1kFuwx-6Z0WR4aCQP7k401SdY1ctxIu5Cw7MYH=
4GVtICTlU8APTxjPC-T67AnobWi6NlIm6c_1ugALxOQeDf9MgylWkhGG29xxSxEYVwXYQG6GatU=
TqIdRqkiKVpuEuKteIFeMiNwjsxzC_xYBQIodGi6UG5edW7EOPNemSHXMOdP4A/4j2/xGBCh4XL=
R7yh8uZsdNduhA/h0/h001.LB278SiPp9amJpIDmyGQt22efwVWbBvnksCFxc0wiEw"><span c=
lass=3D"translation_missing" title=3D"translation missing: en.templates.pos=
ts.email.header.read_online">Read Online</span></a></p></td></tr><tr><td cl=
ass=3D"dd" align=3D"center" valign=3D"top" style=3D"padding:15px 0;"><table=
 role=3D"none" width=3D"100%" border=3D"0" cellspacing=3D"0" cellpadding=3D=
"0" align=3D"center"><tr><td align=3D"center" valign=3D"top"><h1 style=3D"t=
ext-align:left;font-family:'Trebuchet MS','Lucida Grande',Tahoma,sans-serif=
;font-weight:Bold;font-size:32px;color:#2A2A2A;padding:2px 0;line-height:38=
px;"> Why Your &quot;Sure Thing&quot; Deals Slip </h1></td></tr></table></t=
d></tr><tr><td align=3D"center" valign=3D"top" class=3D"dd"><table role=3D"=
none" width=3D"100%" border=3D"0" cellspacing=3D"0" cellpadding=3D"0" align=
=3D"center"><tr><td align=3D"left" valign=3D"middle" class=3D"mob-stack"><t=
able role=3D"none" border=3D"0" cellspacing=3D"0" cellpadding=3D"0" align=
=3D"right" class=3D"social-mobile"><tr><td align=3D"left" valign=3D"middle"=
><table role=3D"none" border=3D"0" cellspacing=3D"0" cellpadding=3D"0" alig=
n=3D"left" style=3D"width:100%"><tr><td align=3D"center" valign=3D"middle">=
<a href=3D"https://link.mail.beehiiv.com/ss/c/u001.UY7-jEMcRLZ5W6M0bzLpmxH7=
-WTt-1gChtTcndEMyBoSwgSdDaOALV1MAeTHOBSUWCqEjdMxJtRDlZvsKnAu88fuP77Fa517iEn=
n6h_MBewxdd3SeXqPU_GPLJG7D5JnVwmYqVACYXBKXebYSZSYo3ngqi4r3RcpXvjOfNgPeB9-PM=
IhABIQ6un-WJ5M9tq82gbFtkLam4w-l0ZUQg7lkZ9a-sFDmdB-tD8hsBSoGlQcRXfbmNdCUFGDu=
1kFHx-OkkIfWZfJQMBrV0YNG9QN-V-rF6wEvAheJXRMg-LV3Pbs0qkZ39Qny765Susl3JHhO_Xd=
2M5OoSd0Cd15ZiGONxxVVObzGRCEfX2t_pjwb3Y/4j2/xGBCh4XLR7yh8uZsdNduhA/h1/h001.=
-182kSrPUv5EJrxcs1JsSjcJIPJA5gDadv2UkPwtiJY" style=3D"text-decoration:none;=
 display:block;"><table role=3D"none" border=3D"0" cellspacing=3D"0" cellpa=
dding=3D"0" align=3D"center"><tr><td align=3D"center" valign=3D"middle" sty=
le=3D"border: 1px solid #E5E7EB; border-radius: 100%; width: 18px; height: =
18px; padding: 8px;"><img style=3D"display:block; width:100%; height:100%; =
max-width:18px; max-height:18px; object-fit: contain;" alt=3D"share on face=
book" width=3D"18" border=3D"0" src=3D"https://media.beehiiv.com/cdn-cgi/im=
age/fit=3Dscale-down,format=3Dauto,onerror=3Dredirect,quality=3D80/static_a=
ssets/header/facebook.png"/></td></tr></table></a></td><td width=3D"8" styl=
e=3D"width:8px;">&nbsp;</td><td align=3D"center" valign=3D"middle"><a href=
=3D"https://link.mail.beehiiv.com/ss/c/u001.eT_HH9j2kUx6jXW0PHemwzOjQOpuqUK=
Cn7LAbiCzlo1oxUN44u16xvalV9lCzdHNf-2oVWwF8nFIujoz8Z4ultPayspV7EV3WtW764jIYd=
FWxBuyQQicUWPEW211e72nGj7cE9YYeG52ST5zcyJW-4BkdfkWOJzHSJkBTzQDHnh_tIqApqKZt=
AmFJRv0MMDmnNfg5gnnbd5zvZZ_zeUIx2jTkPkhudFbFjHmnz2MjYDnVvyrhS-qp8ei2Q3Fc_cN=
i4En7_4uYGIEwIOqjwCA5wgiNbX-Fya8DWAeeZcFBGK8BC8b_nZMgB_INy8XxL3NmPbI-0xQA_w=
OC8hpcpAAuINuIbTLQzfHqmAg6HZLJhI/4j2/xGBCh4XLR7yh8uZsdNduhA/h2/h001.Zv4Bdl8=
i4nkxpxxhZj8ReuZcR70VR93ttpRadBbZEPE" style=3D"text-decoration:none; displa=
y:block;"><table role=3D"none" border=3D"0" cellspacing=3D"0" cellpadding=
=3D"0" align=3D"center"><tr><td align=3D"center" valign=3D"middle" style=3D=
"border: 1px solid #E5E7EB; border-radius: 100%; width: 18px; height: 18px;=
 padding: 8px;"><img style=3D"display:block; width:100%; height:100%; max-w=
idth:18px; max-height:18px; object-fit: contain;" alt=3D"share on twitter" =
width=3D"18" height=3D"18" border=3D"0" src=3D"https://media.beehiiv.com/cd=
n-cgi/image/fit=3Dscale-down,format=3Dauto,onerror=3Dredirect,quality=3D80/=
static_assets/header/x.png"/></td></tr></table></a></td><td width=3D"8" sty=
le=3D"width:8px;">&nbsp;</td><td align=3D"center" valign=3D"middle"><a href=
=3D"https://link.mail.beehiiv.com/ss/c/u001.UY7-jEMcRLZ5W6M0bzLpm9U9S1JYcj8=
zH88ooT01vXOKGqw1BJYJi8XJOykB3s2LWl1rCZfKcz3DAnKFS5ActNz6yZIhzmMblfyjAusUfx=
0Ud58Qp1r24BDsVWrEM6f8cLdCIXfA6bEl7Hm_2PmsdbqOQ_QpPeFZqhcxwatd761VH-7q3Asbz=
1nbpOSqxoy3HEQuWQHozPXqzq_OTHvY14fASrppF9el62-svbg4Jp1I0n82yLm1tC7fPCiaLiWb=
Uu5BGuQyOeKJ6os6to2Ov9oBMNQq_2VNyr3zLEfNso2wpxsQgaiVrG5iPdLh2Oj4mHj544V2vNy=
kDmQNnsv0XpKTHMrwzgdrGNJbXySPSM0/4j2/xGBCh4XLR7yh8uZsdNduhA/h3/h001.mzUrbh6=
g77LjWLhTRH6Wtu2JjMDTEGvipMVIHDzh0qU" style=3D"text-decoration:none; displa=
y:block;"><table role=3D"none" border=3D"0" cellspacing=3D"0" cellpadding=
=3D"0" align=3D"center"><tr><td align=3D"center" valign=3D"middle" style=3D=
"border: 1px solid #E5E7EB; border-radius: 100%; width: 18px; height: 18px;=
 padding: 8px;"><img style=3D"display:block; width:100%; height:100%; max-w=
idth:18px; max-height:18px; object-fit: contain;" alt=3D"share on threads" =
width=3D"18" height=3D"18" border=3D"0" src=3D"https://media.beehiiv.com/cd=
n-cgi/image/fit=3Dscale-down,format=3Dauto,onerror=3Dredirect,quality=3D80/=
static_assets/header/threads.png"/></td></tr></table></a></td><td width=3D"=
8" style=3D"width:8px;">&nbsp;</td><td align=3D"center" valign=3D"middle"><=
a href=3D"https://link.mail.beehiiv.com/ss/c/u001.UY7-jEMcRLZ5W6M0bzLpm5Vso=
l3-4mO68bGpSvtYIyCFMPHZM3NHfCQCEvGpU3U82219i03ZXpcWbsDp4yL-p4wFphx3jgPGkl4R=
GiC6osrPmeON1utPuYLqtNp-cn74RuURMm38Tf8s5mwuV_deQwfaWOiKTSa410OEO-CEZ7N46z6=
NjTdJ_FwX1hiIlRqZQ3ksGKwEeTBi_IHXgCLrP3AGWESVSCkIr2EbEr3akPndKg98p4nuzQVNMQ=
40fuB1bNBTg7Qgi98qo9w9TQRM5DRj04lhYnXIZurv27QFiuAY48088l9MdbFgknIzRXAPPUOJE=
4NDXDKhnE31FncF9aSCUBSFzoagI-3HmCTpHzA/4j2/xGBCh4XLR7yh8uZsdNduhA/h4/h001.P=
wWWeOn_6TFAxcmtLxLuM9Y5TUjawnJiU0GG18YIgY4" style=3D"text-decoration:none; =
display:block;"><table role=3D"none" border=3D"0" cellspacing=3D"0" cellpad=
ding=3D"0" align=3D"center"><tr><td align=3D"center" valign=3D"middle" styl=
e=3D"border: 1px solid #E5E7EB; border-radius: 100%; width: 18px; height: 1=
8px; padding: 8px;"><img style=3D"display:block; width:100%; height:100%; m=
ax-width:18px; max-height:18px; object-fit: contain;" alt=3D"share on linke=
din" width=3D"18" height=3D"18" border=3D"0" src=3D"https://media.beehiiv.c=
om/cdn-cgi/image/fit=3Dscale-down,format=3Dauto,onerror=3Dredirect,quality=
=3D80/static_assets/header/linkedin.png"/></td></tr></table></a></td></tr><=
/table></td></tr></table></td></tr></table></td></tr><tr><td style=3D"heigh=
t:0px;width:0px;"><div style=3D"height:1px;" data-open-tracking=3D"true"> <=
img src=3D"https://link.mail.beehiiv.com/ss/o/u001.QDl44NxZBc1mRkS74rGpGQ/4=
j2/xGBCh4XLR7yh8uZsdNduhA/ho.gif" alt=3D"" width=3D"1" height=3D"1" border=
=3D"0" style=3D"height:1px !important;width:1px !important;border-width:0 !=
important;margin-top:0 !important;margin-bottom:0 !important;margin-right:0=
 !important;margin-left:0 !important;padding-top:0 !important;padding-botto=
m:0 !important;padding-right:0 !important;padding-left:0 !important;"/> </d=
iv></td></tr></table></div></td></tr><tr id=3D"content-blocks"><td class=3D=
"email-card-body" align=3D"center" valign=3D"top" style=3D"padding-bottom:1=
5px;"><table role=3D"none" width=3D"100%" border=3D"0" cellspacing=3D"0" ce=
llpadding=3D"0" align=3D"center"><tr><td class=3D"dd" align=3D"left" style=
=3D"padding:0px 15px;text-align:left;word-break:break-word;"><p style=3D"ms=
o-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">Hello And=
rew, </span></p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"padd=
ing:0px 15px;text-align:left;word-break:break-word;"><p style=3D"mso-line-h=
eight-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);"><i><b>Book update=
</b></i></span><span style=3D"color:rgb(44, 62, 80);"><i>: I had to go back=
 to square one with the audiobook editor, they didn=E2=80=99t do a great jo=
b so I decided to start over. I=E2=80=99ll hopefully have them to share lat=
er this month. </i></span></p></td></tr><tr><td class=3D"dd" align=3D"left"=
 style=3D"padding:0px 15px;text-align:left;word-break:break-word;"><p style=
=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);"><b>=
<i>Pre-order benefits</i></b></span><span style=3D"color:rgb(44, 62, 80);">=
<i>: For anyone that pre-orders the book, I have a monthly zoom call where =
we work on revenue problems plus you get access to the Investor list I shar=
ed a few weeks back. I have something interesting coming next week or two a=
nd you=E2=80=99ll get that too once it=E2=80=99s live=E2=80=A6 </i></span><=
/p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;=
text-align:left;word-break:break-word;"><p style=3D"mso-line-height-alt:150=
.0%;"><span style=3D"color:rgb(44, 62, 80);"><i>You can order the </i></spa=
n><span style=3D"color:rgb(44, 62, 80);"><a class=3D"link" href=3D"https://=
link.mail.beehiiv.com/ss/c/u001.UY7-jEMcRLZ5W6M0bzLpmzKZu4CMZ-4VPqYNLlg6yrG=
xR2XQhddm9dZyX6mpnTOell2BYjET-Y8l9HDSfj1AJQh-u__Ozm5nzjGP54xQkGt8BkBwNf31D7=
9F3CPl6rqE0csmgiDjAQi8JfWYU1YHq8qLIL3rukeIoNRtPc66neihCiQ-9xchQDhpEmGm0BdyF=
g1kVTvEDUOwOymK-8vfxWfNXwR81Uw9_ZQJmYyVzyLY-63U1RJVH3q1-cLqXQQsg4WG161D0j3E=
roxaBwnSn0g1my3Lu8t6XUojy0mDM2MPkAVGtno3Rug3HPHvM-SB/4j2/xGBCh4XLR7yh8uZsdN=
duhA/h5/h001.LVbWbm9_MrARWgSBkI_erTs-HemQMCgr4HWahozDN1M" target=3D"_blank"=
 rel=3D"noopener noreferrer nofollow"><span><i>book here</i></span></a></sp=
an><span style=3D"color:rgb(44, 62, 80);"><i>. Email me your receipt and I&=
#39;ll add you to the event/share the sheet. </i></span></p></td></tr><tr><=
td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:left;wo=
rd-break:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span style=
=3D"color:rgb(44, 62, 80);">Ok, now onto the newsletter.</span></p></td></t=
r><tr><td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:=
left;word-break:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span=
 style=3D"color:rgb(44, 62, 80);"><i>The deals you&#39;re most excited abou=
t? They&#39;re often the ones that crash and burn.</i></span></p></td></tr>=
<tr><td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:le=
ft;word-break:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span s=
tyle=3D"color:rgb(44, 62, 80);">I learned this the hard way with a $600,000=
 Olympic security contract. I had the PO, had verbal approval from four dif=
ferent organizations, had 76 generators sitting in a yard ready to deploy. =
Then got the call: &quot;Sorry, we&#39;re not going to do it.&quot;</span><=
/p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;=
text-align:left;word-break:break-word;"><p style=3D"mso-line-height-alt:150=
.0%;"><span style=3D"color:rgb(44, 62, 80);">That one still stings. But it =
taught me something important about enterprise deals: they&#39;re unpredict=
able as hell, and the stuff that kills them is usually hiding in plain sigh=
t.</span></p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"padding=
:0px 15px;text-align:left;word-break:break-word;"><p style=3D"mso-line-heig=
ht-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">The Vancouver Olympi=
cs were coming up, and there was real concern about security after the Lond=
on tube bombing and 9/11. They wanted to test all the security systems ahea=
d of time, but couldn&#39;t get 220-volt power to the remote locations in t=
ime. So I organized 76 generators from across Canada to provide temporary p=
ower for a two-week testing period. We had everything lined up, contracts s=
igned, generators sitting in the yard ready to deploy.</span></p></td></tr>=
<tr><td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:le=
ft;word-break:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span s=
tyle=3D"color:rgb(44, 62, 80);">Then they called and said they&#39;d run ou=
t of time to do the testing properly. They were just going to wing it durin=
g the actual Olympics. Six hundred thousand dollars, gone. My boss gave me =
a 2% consolation prize from the $60k consulting fee we negotiated for our t=
rouble. I was livid. But that deal taught me more about enterprise sales th=
an any course ever could.</span></p></td></tr><tr><td id=3D"why-big-deals-r=
eally-stall" class=3D"dd" align=3D"left" valign=3D"top" style=3D"color:#2A2=
A2A;font-weight:normal;padding:0px 15px;text-align:left;"><h2 style=3D"colo=
r:#2A2A2A;font-weight:normal;mso-line-height-alt:150.0%;"><span style=3D"co=
lor:rgb(44, 62, 80);">Why Big Deals Really Stall</span></h2></td></tr><tr><=
td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:left;wo=
rd-break:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span style=
=3D"color:rgb(44, 62, 80);">Been thinking about this after a client call th=
is week. Their pipeline is looking strong=E2=80=94multiple six-figure deals=
 moving forward, champions engaged, verbal commitments. But I&#39;ve seen t=
his movie before.</span></p></td></tr><tr><td class=3D"dd" align=3D"left" s=
tyle=3D"padding:0px 15px;text-align:left;word-break:break-word;"><p style=
=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">Big=
 deals typically stall because you missed something. It could be a holiday =
with a key buying influence, a requirement that&#39;s really a deal killer,=
 or an influencer with a competing project. When all you&#39;re focused on =
is giving your demo, you&#39;re not spending enough time asking the real qu=
estions that will de-risk the deal and find the things that will stall or k=
ill it.</span></p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"pa=
dding:0px 15px;text-align:left;word-break:break-word;"><p style=3D"mso-line=
-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">Most sales reps=
 fall into the demo trap. They get excited when a prospect says &quot;show =
me what you&#39;ve got&quot; and rush straight into product mode. But what =
they should be doing is digging deeper. Who else needs to see this? What ha=
ppened to the last vendor you evaluated? What would make this project not h=
appen? What other priorities are competing for budget this quarter?</span><=
/p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;=
text-align:left;word-break:break-word;"><p style=3D"mso-line-height-alt:150=
.0%;"><span style=3D"color:rgb(44, 62, 80);">The stuff that kills deals is =
rarely about your product. It&#39;s about timing, politics, budget cycles, =
and personalities. Your champion gets promoted and their replacement has di=
fferent priorities. The CFO decides to freeze all new spending. A key stake=
holder goes on sabbatical right when you need their approval. Someone in pr=
ocurement has a relationship with your competitor.</span></p></td></tr><tr>=
<td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:left;w=
ord-break:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span style=
=3D"color:rgb(44, 62, 80);">Every unknown in your deal is basically 100% ri=
sk. The more unknowns you have, the more likely you are to get that &quot;s=
orry, we&#39;re not moving forward&quot; email. This is why I&#39;ve become=
 obsessed with what my friend Megan Wilson (one of the best enterprise clos=
ers I know) calls &quot;de-risking deals.&quot; Every piece of information =
you gather, every process step you understand, every stakeholder you identi=
fy removes a bit of that risk.</span></p></td></tr><tr><td class=3D"dd" ali=
gn=3D"left" style=3D"padding:0px 15px;text-align:left;word-break:break-word=
;"><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62=
, 80);">The problem is most of us treat sales like we&#39;re fortune teller=
s. We look at a deal and make up a probability based on gut feel. &quot;Thi=
s one feels like 80%.&quot; But what if there&#39;s a technical requirement=
 you don&#39;t know about? What if your champion doesn&#39;t actually contr=
ol the budget? What if they&#39;re planning a hiring freeze next quarter? Y=
our 80% might actually be 20%.</span></p></td></tr><tr><td class=3D"dd" ali=
gn=3D"left" style=3D"padding:0px 15px;text-align:left;word-break:break-word=
;"><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62=
, 80);">Even deals with verbal commitments can disappear overnight. I&#39;v=
e seen it happen more times than I can count. Your champion gets fired. Bud=
get priorities change. A competitor comes in with a relationship you didn&#=
39;t know about. The company gets acquired and all purchasing decisions get=
 frozen. Wild stuff happens in enterprise sales, and the bigger the deal, t=
he more opportunities there are for things to go wrong.</span></p></td></tr=
><tr><td id=3D"two-things-that-actually-help" class=3D"dd" align=3D"left" v=
align=3D"top" style=3D"color:#2A2A2A;font-weight:normal;padding:0px 15px;te=
xt-align:left;"><h2 style=3D"color:#2A2A2A;font-weight:normal;mso-line-heig=
ht-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">Two Things That Actu=
ally Help</span></h2></td></tr><tr><td class=3D"dd" align=3D"left" style=3D=
"padding:0px 15px;text-align:left;word-break:break-word;"><p style=3D"mso-l=
ine-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);font-weight:70=
0;"><b>Ask About Their Timeline (But Do It Right)</b></span></p></td></tr><=
tr><td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:lef=
t;word-break:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span st=
yle=3D"color:rgb(44, 62, 80);">On your second or third call, ask: </span><s=
pan style=3D"color:rgb(44, 62, 80);"><i>&quot;When do you ideally want to h=
ave something like this in place?&quot;</i></span><span style=3D"color:rgb(=
44, 62, 80);"> Not &quot;when do you want to buy?&quot; Just when they want=
 the problem solved. This question is magic because it gets them thinking a=
bout their own process=E2=80=94what approvals they need, when budget cycles=
 hit, if anyone&#39;s going on vacation.</span></p></td></tr><tr><td class=
=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:left;word-break=
:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"color=
:rgb(44, 62, 80);">You&#39;ll learn more from this one question than from t=
hree discovery calls. They&#39;ll start thinking out loud about all the ste=
ps that need to happen. &quot;Well, we&#39;d need to get it through securit=
y review first, and Jennifer handles that but she&#39;s going on maternity =
leave in October. And then legal would need to look at it, which usually ta=
kes about six weeks. Oh, and we can&#39;t implement anything new in Q4 beca=
use of the product launch.&quot;</span></p></td></tr><tr><td class=3D"dd" a=
lign=3D"left" style=3D"padding:0px 15px;text-align:left;word-break:break-wo=
rd;"><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, =
62, 80);">Suddenly you understand their real timeline and all the potential=
 roadblocks. You&#39;re not selling to them anymore=E2=80=94you&#39;re help=
ing them solve a logistics puzzle. This one question reveals the decision-m=
aking process, the stakeholders involved, the budget cycle, and potential t=
iming conflicts. It&#39;s the difference between hoping for the best and ac=
tually understanding what needs to happen.</span></p></td></tr><tr><td clas=
s=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:left;word-brea=
k:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"colo=
r:rgb(44, 62, 80);">But here&#39;s the key: you have to actually listen to =
what they tell you. When they mention that Jennifer handles security review=
, ask about Jennifer. When do you need to get this to her? What does she ty=
pically look for? Has she killed deals before? When they mention the Q4 imp=
lementation freeze, dig into that. Why the freeze? Who decided that? Are th=
ere any exceptions?</span></p></td></tr><tr><td class=3D"dd" align=3D"left"=
 style=3D"padding:0px 15px;text-align:left;word-break:break-word;"><p style=
=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);font-=
weight:700;"><b>Use a Mutual Action Plan</b></span></p></td></tr><tr><td cl=
ass=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:left;word-br=
eak:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"co=
lor:rgb(44, 62, 80);">Sounds fancy, but it&#39;s just a shared project plan=
 before they&#39;re a customer. Once you know their timeline, work backward=
s. When do we need to finish the trial? When does this need to go through l=
egal? When do we need budget approval? Who needs to sign off at each step?<=
/span></p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"padding:0p=
x 15px;text-align:left;word-break:break-word;"><p style=3D"mso-line-height-=
alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">Put it in a simple spre=
adsheet with owners and dates. Include things like &quot;Security review co=
mpleted by Jennifer&quot; and &quot;Legal approval received&quot; and &quot=
;Budget confirmed with finance team.&quot; Share it after they&#39;re engag=
ed (never on the first call=E2=80=94that&#39;s weird).</span></p></td></tr>=
<tr><td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:le=
ft;word-break:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span s=
tyle=3D"color:rgb(44, 62, 80);">The beauty is you&#39;re not pushing them t=
o buy. You&#39;re helping them figure out their own process. You become the=
ir sherpa, not their vendor. And when things start to slip, you can point t=
o the plan and say, &quot;Hey, we agreed Jennifer needed to finish the secu=
rity review by the 15th. Should we push everything back a week, or is there=
 another way to handle this?&quot;</span></p></td></tr><tr><td class=3D"dd"=
 align=3D"left" style=3D"padding:0px 15px;text-align:left;word-break:break-=
word;"><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44=
, 62, 80);">I got this idea from Tom Williams at Clari Align when I had him=
 on my podcast. He&#39;s the head of their sales collaboration platform and=
 has been thinking about this stuff for years. He even shared a template, w=
hich I&#39;ll dig up and send to anyone who replies to this email asking fo=
r it. The whole concept is about lowering risk through collaboration=E2=80=
=94not just with your champion, but with everyone involved in the buying pr=
ocess.</span></p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"pad=
ding:0px 15px;text-align:left;word-break:break-word;"><p style=3D"mso-line-=
height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">The mutual actio=
n plan works because it forces everyone to be honest about what actually ne=
eds to happen. No more vague &quot;we&#39;ll probably sign next quarter&quo=
t; conversations. Instead, you have specific milestones with specific owner=
s and specific dates. When someone says they can get budget approval &quot;=
soon,&quot; you can look at the plan together and say, &quot;Okay, if we wa=
nt to go live by January 15th, we need budget approval by December 1st. Doe=
s that work with your finance team&#39;s schedule?&quot;</span></p></td></t=
r><tr><td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:=
left;word-break:break-word;"><p style=3D"mso-line-height-alt:150.0%;"><span=
 style=3D"color:rgb(44, 62, 80);">Tom&#39;s approach goes beyond just timel=
ine planning though. He maps the stages to the buyer&#39;s journey instead =
of your sales process. What do they need to educate themselves about? How d=
o they validate vendors? What jobs do they need to get done internally? The=
n you build the plan around helping them accomplish those things, not just =
hitting your sales milestones.</span></p></td></tr><tr><td class=3D"dd" ali=
gn=3D"left" style=3D"padding:0px 15px;text-align:left;word-break:break-word=
;"><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62=
, 80);"><i>Reply with the word MAP and I=E2=80=99ll share Tom=E2=80=99s tem=
plate.</i></span></p></td></tr><tr><td id=3D"your-next-move" class=3D"dd" a=
lign=3D"left" valign=3D"top" style=3D"color:#2A2A2A;font-weight:normal;padd=
ing:0px 15px;text-align:left;"><h2 style=3D"color:#2A2A2A;font-weight:norma=
l;mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">Your =
Next Move</span></h2></td></tr><tr><td class=3D"dd" align=3D"left" style=3D=
"padding:0px 15px;text-align:left;word-break:break-word;"><p style=3D"mso-l=
ine-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">Pick one thi=
ng to try this week. Ask that timeline question on your next call and reall=
y listen to what they tell you about their process. Sketch out a simple act=
ion plan for your best deal=E2=80=94just a list of the steps that need to h=
appen and when. Start tracking where your champions go when they change job=
s.</span></p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"padding=
:0px 15px;text-align:left;word-break:break-word;"><p style=3D"mso-line-heig=
ht-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">The deals you&#39;re=
 most excited about will probably crash and burn. The ones that sneak up on=
 you become your biggest wins. My client&#39;s biggest deal this quarter ca=
me from a guy they thought had gone dark months ago. He just re-engaged out=
 of nowhere because his priorities changed and suddenly the problem became =
urgent.</span></p></td></tr><tr><td class=3D"dd" align=3D"left" style=3D"pa=
dding:0px 15px;text-align:left;word-break:break-word;"><p style=3D"mso-line=
-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);">Focus on the pr=
ocess, not counting the money. Every deal teaches you something about how t=
hese things really work. Even the ones that blow up in your face=E2=80=A6 E=
specially those ones.</span></p></td></tr><tr><td class=3D"dd" align=3D"lef=
t" style=3D"padding:0px 15px;text-align:left;word-break:break-word;"><p sty=
le=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, 80);"><=
i>Hit reply if you&#39;ve got a deal that went sideways in a weird way. I l=
ove hearing these stories.=C2=A0</i></span></p></td></tr><tr><td class=3D"d=
d" align=3D"left" style=3D"padding:0px 15px;text-align:left;word-break:brea=
k-word;"><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(=
44, 62, 80);">Collin=C2=A0</span></p></td></tr><tr><td class=3D"dd" align=
=3D"left" style=3D"padding:0px 15px;text-align:left;word-break:break-word;"=
><p style=3D"mso-line-height-alt:150.0%;"><span style=3D"color:rgb(44, 62, =
80);">PS - reply back with MAP if you want the mutual action plan template =
from Tom Williams - I&#39;ll dig it up and send it over.</span></p></td></t=
r></table></td></tr></table></td></tr><tr><td align=3D"center" valign=3D"to=
p"><table role=3D"none" width=3D"100%" border=3D"0" cellspacing=3D"0" cellp=
adding=3D"0" align=3D"center"><tr><td><tr><td class=3D"b" align=3D"center" =
valign=3D"top" bgcolor=3D"#007b8a" style=3D"padding:0px 0px 0px 0px;border-=
style:solid;border-width: 0px 0px 0px 0px;border-color: #FFFFFF;border-bott=
om-left-radius:10px;border-bottom-right-radius:10px;"><table role=3D"none" =
width=3D"100%" border=3D"0" cellspacing=3D"0" cellpadding=3D"0" align=3D"ce=
nter"><tr><td align=3D"center" valign=3D"top" bgcolor=3D"#f5bf83" style=3D"=
padding:12px"><table role=3D"none" width=3D"100%" border=3D"0" cellspacing=
=3D"0" cellpadding=3D"0" align=3D"center"><tr><td><span style=3D"padding-le=
ft:1px;"></span></td><td align=3D"center" valign=3D"middle" width=3D"75" st=
yle=3D"width:75px;"><a href=3D"https://link.mail.beehiiv.com/ss/c/u001.UY7-=
jEMcRLZ5W6M0bzLpm8v47JXV6QXIAtz1TPWJq9DEryZLbI4J7WWM_PiHqFGhUv3dFjKc0YTlxsb=
6kGtkhlDDYMSkxOmwZjioCqapkMSYv3pYIrw-QlG7DD9r7iWpX7f0K4MH_zYdsqXyU91LhtYXvi=
JO2sCRn_mmzhnaSsFEiGxlZDINross-wLVDZP6ZuHQNnHqwHho-_tWwAnpf7KNoTALxfs-ePrwU=
I8j7Hf8SM1FDY8Fu_zX1e2WF8T6zSLzt9T8VsBexQmbZ7KcqA/4j2/xGBCh4XLR7yh8uZsdNduh=
A/h6/h001.6doi4uZ9cEK3XtD33j9TOLavmOcHwIc_2hVI0mmfhCw" style=3D"text-decora=
tion:none;"><img width=3D"22" height=3D"16" alt=3D"yt" border=3D"0" style=
=3D"display:block;max-width:22px;color:light" src=3D"https://media.beehiiv.=
com/cdn-cgi/image/fit=3Dscale-down,format=3Dauto,onerror=3Dredirect,quality=
=3D80/static_assets/youtube_light.png"/></a></td><td align=3D"center" valig=
n=3D"middle" width=3D"75" style=3D"width:75px;"><a href=3D"https://link.mai=
l.beehiiv.com/ss/c/u001.UY7-jEMcRLZ5W6M0bzLpm5Vsol3-4mO68bGpSvtYIyC7RTGiT9-=
zovb8Qim6eBsoZYnUTL-c3CH3zOZ6o4_EJ18kRZVqjtRHEDTV3-_Slq-mH_MOhFNLoE7ui5im_I=
9QhwMR7XuC0D6StZqcy-MBQdC2huMJ5TPdVpu_8lD0kwHHp_vcuT1H3yH2RxQ8H9leuHka3P-Bz=
DipPSNJQEjGATRDbVNWlHxINSi2gh3fDT05sEuoj3s8w03V2zAdGdMOeAX7jLdorcPCsOsKYMIF=
gA/4j2/xGBCh4XLR7yh8uZsdNduhA/h7/h001.6VFLAwGMfdyftEQ4UZj4Ct8KwFL8fbJ2KBPop=
XoS1Bc" style=3D"text-decoration:none;"><img width=3D"22" height=3D"22" alt=
=3D"in" border=3D"0" style=3D"display:block;max-width:22px;color:light" src=
=3D"https://media.beehiiv.com/cdn-cgi/image/fit=3Dscale-down,format=3Dauto,=
onerror=3Dredirect,quality=3D80/static_assets/linkedin_light.png"/></a></td=
><td><span style=3D"padding-left:1px;"></span></td></tr></table></td></tr><=
tr><td height=3D"10" style=3D"line-height:1px;font-size:1px;height:10px;"> =
&nbsp; </td></tr><tr><td class=3D"w" align=3D"center" valign=3D"top" style=
=3D"padding:15px 15px 15px 15px;"><table role=3D"none" width=3D"100%" borde=
r=3D"0" cellspacing=3D"0" cellpadding=3D"0" align=3D"center"><tr><td align=
=3D"center" valign=3D"top"><p style=3D"font-family:'Verdana',Geneva,sans-se=
rif;color:#FFFFFF!important;"> Update your email preferences or unsubscribe=
 <a class=3D"link" href=3D"https://link.mail.beehiiv.com/ss/c/u001.r7o6LfRL=
XwQ-3g4cvdmKtd8SJB4D4z2stBRrWAMoYsjkniBcmw8veChmAMJ0vo1ksC9d40gtrOqgw6X38rZ=
UI-Adnkdn-_JHdtcg6VYiUpAiGbWhO4cpRZTXLk4h-hbgzzncRp4jDZZNV_YtgWQ2IU0uFKABhn=
YHUkZJhyL1owyjLBPknkN6F6TRspknklf5xRb60z7aJ5HKO9bRXSnRJVHqn80AcldMwXohcbLC_=
1cJ-MtpcGuQqOCn_DnaS__6_3gDj-aqZZyVlLSjPZwgPUKihQpp7PC6XU3bTHhdlxW1JcYE3_Wq=
m59rScB5X6CHt_PW_NDIL4lea5RXgLzqYtIACJOAvp5EEiDC5a9zQvWA8hCfJSHnnlF17dGUqsJ=
v3tv1YLflafDSm9QLe5UBWsRDhnH2iFLAsYdu6xCH5-jwC75MsX4YCT6eSDtB_xDz4SO2T6eMy5=
M_ayvGLJX8pH_Vut7KjQHcD-FJy2bYs9gMrSPJdWOT0dv4qPCmoCS08LBjY6D49oi_OffGyxiDv=
RS2N0UXICQdZMZPyqQhqbT4j3BYgx7fQ1X06ypZ5LeODsgskNq41M2sqPLCI4sy1RdwIpZcNSPn=
vUlf-XoCTaVu1RxWv3X7naO1wVbrn42ckyN8XRa9CmZz7P8_x6d-QEfxn5utllehWDVpS9d_sJ8=
yk0mscXPst9T0kW5UkOduY7WKAFhocBA6zN0ZP82aU6T2fZf5dmSTwT6VipYvbX_8OmqrMryX-M=
e53SK3CLq2obd7coogZX2EtFNX3b_hyV3HyoVjxt1zwHO_NRmHNX_2srzR7cLmoAXdl3Wew4vsR=
8_BM30y8gx07NYFWFpCiHPVZnqkMFz6XORZIrCXeLA/4j2/xGBCh4XLR7yh8uZsdNduhA/h8/h0=
01.3PKKNIInpEubzv6i-6WEr01g-g2aHS8yNDsD5gENiHU" style=3D"text-decoration:un=
derline;text-decoration-color:#FFFFFF!important;color:#FFFFFF!important;"> =
here</a></p><p class=3D"copyright" style=3D"font-family:'Verdana',Geneva,sa=
ns-serif;color:#FFFFFF!important;"> &copy; 2025 Predictable Revenue: Founde=
rs Edition </p><p style=3D"font-family:'Verdana',Geneva,sans-serif;color:#F=
FFFFF!important;"> #304 210 Carrall Street<br>Vancouver, BC V6B 2J1, Canada=
 </p></td></tr><tr style=3D"display: table-row !important;"><td align=3D"ce=
nter" valign=3D"top" style=3D"padding-top:20px;" style=3D"display:table-cel=
l !important;"><table role=3D"none" border=3D"0" cellspacing=3D"0" cellpadd=
ing=3D"0" align=3D"center" style=3D"display:table !important;"><tr style=3D=
"display:table-row !important;"><td class=3D"u" align=3D"center" valign=3D"=
middle" height=3D"32" style=3D"height:32px;display:table-cell !important; m=
ax-height: 32px !important;margin:0px !important; background-color: #ffffff=
 !important;"><a style=3D"line-height:32px !important;text-decoration:none;=
display:block !important;" href=3D"https://link.mail.beehiiv.com/ss/c/u001.=
UY7-jEMcRLZ5W6M0bzLpm7ZVFEiXSRTIYwLhTGqSbF-WmIvKCMLikHtbp1IhPdLZ7obm_ojey4e=
Xmbb7Beivnhr-Tt56DN2SGys9QReFGAJIdrctVxuh3HAQsr0PnH1HPGMUjwcAgc74RPtvLAgh9b=
_QauRtZycA2dYfm4RdAkpBrRCBV24FqbldKH25KZJ4f6A9JIbAcAul2JVB89vlA3vy9XV-W6h7B=
zrMtOnWXrh8HMSiipSXbDXQv2icrmWsnVxblQKZ0BsM10mK28gSfA/4j2/xGBCh4XLR7yh8uZsd=
NduhA/h9/h001.vGQvykuE5NJ-fhf-mRJ4HjlHWZqfNx3jrmyOPPMw9kQ"><img src=3D"http=
s://media.beehiiv.com/output-onlinepngtools.png" width=3D"16" alt=3D"beehii=
v logo" style=3D"display:inline-block !important;max-width:16px !important;=
 vertical-align:-3px !important;width: 16px !important;" border=3D"0"/><spa=
n style=3D"padding-left:11px !important;display: inline-block !important;">=
Powered by beehiiv</span></a></td></tr></table></td></tr><tr><td align=3D"l=
eft" valign=3D"top" height=3D"2" style=3D"height:2px;"><a href=3D'https://l=
ink.mail.beehiiv.com/ss/c/u001.5yp-JOwx74Tmo9GvRWkFa1lilyjuTeq0GeW-iPG9ZdQ4=
D6ta-yqGGTKLpStdJu0g9AsLlqGMrVJp5BiQuGLb0fLI2H4xloCARxj_AejjHzw/4j2/xGBCh4X=
LR7yh8uZsdNduhA/h10/h001._XOVtcvewMzDn8CdIRv9IEcM8THpMIPgHKY1OZzBu6E' style=
=3D"color: #007b8a !important; cursor: default; font-size: 1px; text-decora=
tion: none;"> Terms of Service </a></td></tr></table></td></tr></table></td=
></tr></td></tr></table></td></tr></table></td></tr></table></td></tr></tab=
le></div></body></html>
--0fc44c6b0b8b6e17ec90552f12363d11e89ddd46eae1478323daca2c7491--