Return-Path: Delivered-To: andrew@sterlingcal.com Received: from reseller401.webserversystems.com by reseller401.webserversystems.com with LMTP id 6JAUGEDW5me5PQsAchKAPA (envelope-from ) for ; Fri, 28 Mar 2025 12:02:56 -0500 Return-path: Envelope-to: andrew@sterlingcal.com Delivery-date: Fri, 28 Mar 2025 12:02:56 -0500 Received: from o166.ptr78.mail.beehiiv.com ([159.183.29.70]:61190) by reseller401.webserversystems.com with esmtps (TLS1.2) tls TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (Exim 4.98.1) (envelope-from ) id 1tyD6d-000000037tB-1ZWJ for andrew@sterlingcal.com; Fri, 28 Mar 2025 12:02:56 -0500 DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=mail.beehiiv.com; h=content-type:from:mime-version:subject:reply-to:list-unsubscribe: list-unsubscribe-post:to:cc:content-type:from:subject:to; s=s1; bh=B5b4nIdiSYHXPQyiTyiCDinw4ClZ60F64SU8PUMTGt0=; b=KGE7dqqXj4rAA0ZjJVjcdhNQ9HbzKIzuR5PSZJQic6xDkUzpXoLcr9aHOCcUfk3FHzwf +6H6uj4bwuadSfaUmCbVQX/3TKBidz/c/18lJdBCp+trpBz0cjYJ9SOh2rsn2bhTbw6k5b no85xXKIFVpjHbOQzV7DDyqXYWUY2xSEK6Xt6xFGGrZkzLU41YwLD2jzcAsEW6GVNe6hpY 4Dfb3g0/WPR9sYu9uPH+7CHZ+DUqAEHezyuvlfvlBVLpjAF5nXCTsUbar9vCDR4L+otx27 Gs1epqXUAhSaStzM1OMTg79r3Y/G+UNsOjqXaa8QT45Vr+lWPHVFIg54PpI1iS8A== Received: by recvd-6c59464dcc-ggh7v with SMTP id recvd-6c59464dcc-ggh7v-1-67E6D624-AC 2025-03-28 17:02:28.858006431 +0000 UTC m=+11562029.854008457 Received: from NDAyMzQxODk (unknown) by geopod-ismtpd-28 (SG) with HTTP id HgUbROhWQ1aI9X74VOuyvg Fri, 28 Mar 2025 17:02:28.785 +0000 (UTC) Content-Type: multipart/alternative; boundary=c406880a3e98072fd07407fb4ebd9513e039487e56ab035af7bcea99234e Date: Fri, 28 Mar 2025 17:02:43 +0000 (UTC) From: Collin Stewart Mime-Version: 1.0 Message-ID: Subject: why deals die Reply-To: Collin Stewart Feedback-ID: =?us-ascii?Q?79bd2e37-5828-4b77-aed7-4f9aca6c748a=3Anewsletter=3A3c5b97ff-00a9-?= =?us-ascii?Q?4acc-916d-c137bca24b1d=3A23270855726497d?= List-Unsubscribe: =?us-ascii?Q?=3Cmailto=3A3c5b97ff-00a9-4acc-916d-c137bca24b1d+1d17dc26-c1df-44e?= =?us-ascii?Q?0-812a-883b6ad5b6bc+79bd2e37-5828-4b77-?= =?us-ascii?Q?aed7-4f9aca6c748a=40unsub=2Ebeehiiv=2Ecom=3E=2C?= =?us-ascii?Q?_=3Chttps=3A=2F=2Ffoundersedition=2Eco=2Funsubscribe=2FeyJ0eXAiOiJKV1QiLCJhbG?= =?us-ascii?Q?ciOiJIUzI1NiJ9=2EeyJzdWJzY3JpYmVyX2lkIjoi?= =?us-ascii?Q?MWQxN2RjMjYtYzFkZi00NGUwLTgxMmEtODgzYjZ?= =?us-ascii?Q?hZDViNmJjIiwicG9zdF9pZCI6Ijc5YmQyZTM3LT?= =?us-ascii?Q?U4MjgtNGI3Ny1hZWQ3LTRmOWFjYTZjNzQ4YSIsI?= =?us-ascii?Q?mxhc3RfcmVzb3VyY2VfZ3VpZCI6IlBvc3Q6Nzli?= =?us-ascii?Q?ZDJlMzctNTgyOC00Yjc3LWFlZDctNGY5YWNhNmM?= =?us-ascii?Q?3NDhhIn0=2E7kO6NPMpeSuKFjpr6iTF0mo7a8VS3V?= =?us-ascii?Q?QOsMKAKzgpyyw=3E?= List-Unsubscribe-Post: List-Unsubscribe=One-Click sId: 3c5b97ff-00a9-4acc-916d-c137bca24b1d x-beehiiv-ids: =?us-ascii?Q?{=22account=5Fname=22=3A=22https=3A=2F=2Ffoundersedition=2Eco=2F=22=2C=22campaign=5Fid=22=3A=227?= =?us-ascii?Q?9bd2e37-5828-4b77-aed7-4f9aca6c748a=22=2C=22c?= =?us-ascii?Q?ategory=22=3A=22newsletter=22=2C=22email=5Fgenerated=5F?= =?us-ascii?Q?at=22=3A1743181348=2C=22user=5Fid=22=3A=223c5b97ff-00a9?= =?us-ascii?Q?-4acc-916d-c137bca24b1d=22}?= x-beehiiv-type: newsletter x-list-id: 3c5b97ff-00a9-4acc-916d-c137bca24b1d x-list-owner: x-newsletter: https://foundersedition.co/p/why-deals-die x-newsletter-id: https://foundersedition.co/ x-newsletter-signup: https://foundersedition.co/subscribe X-SG-EID: =?us-ascii?Q?u001=2E7ozyt+tmjDsHnEocxX8pymFA2v5OOh2V4Pdr6hGVjZo99sLHT4OeEg7as?= =?us-ascii?Q?oEFtQzIa0qAOkk1QezFA4qrCcff9558yNK8x6zQ?= =?us-ascii?Q?0aLhxDCyAuB9kgcSLas3IIKR+fvCUJBBDBEwqnQ?= =?us-ascii?Q?CP3DvGXN2S+MfUAB+RoJ3x5WAizc9CWdZ85DMCs?= =?us-ascii?Q?ckwXZf4KY0QChYCGS3Y+Z6Fe1HVhLABD6ne7hYu?= =?us-ascii?Q?wbcevGO6Qz015xu+F9en8YxXveNeBPvQc9G2klB?= =?us-ascii?Q?3IHeGxTJ84b7LBL=2FWWTqLwPMrQyOo56No5UtmxW?= =?us-ascii?Q?kUkw=2FZ=2Fs=3D?= X-SG-ID: =?us-ascii?Q?u001=2ESdBcvi+Evd=2FbQef8eZF3BpTL9BgbK5wfSJMJGMsmprAVgeiC8iaV7rEmQ?= =?us-ascii?Q?+cYi2k7nc627RqQjtzspAA4hTvLOzTjD9n3ovcm?= =?us-ascii?Q?Hv3z=2FWJV+nLcEeVzuBda2rOsHlsFx=2FcfAeikMRl?= =?us-ascii?Q?bmTLKG3VkM5NKgK5NzoqukmvRaDvDfibLyqoR8v?= =?us-ascii?Q?MIoD6RJr320dtrQILm47Krb8PuhhLMZz2ev2apE?= =?us-ascii?Q?2dTF7F7NmDbB2wjnrC+9PEXRAe05bjyms22dWn=2F?= =?us-ascii?Q?qdb9QByCJqsVW=2FA0hX9lgIcJLw=3D=3D?= To: "andrew@sterlingcal.com" X-Entity-ID: u001.RuZ2+X9IBGtjUb8qq3teHQ== X-Spam-Status: No, score=-4.3 X-Spam-Score: -42 X-Spam-Bar: ---- X-Spam-Flag: NO --c406880a3e98072fd07407fb4ebd9513e039487e56ab035af7bcea99234e Content-Transfer-Encoding: quoted-printable Content-Type: text/plain; charset=utf-8 Mime-Version: 1.0 Hello Andrew,=20 _Quick book update: I=E2=80=99m on my final round of copy-edits for the boo= k and should be shipping those off early next month. Once I=E2=80=99m finis= hed there, I=E2=80=99ll be ramping up the _[_pre-sales_](https://www.amazon= .com/Terrifying-Art-Finding-Customers-Sleep-Deprived/dp/1774586134/)_ campa= ign. _ Most founder-led sales calls start great=E2=80=94prospects love the demo, t= hey're excited about the product, and the conversations leave you feeling c= onfident. But then...nothing. The deals stall, fade away, and no one pulls = out their credit card. The reason? You haven't clearly connected your produ= ct to real, measurable value that your prospects genuinely care about. **What Founders Get Wrong About Value** Too many founders mistake enthusiasm for intent. Prospects might rave about= your cool features or innovative tech, yet still never buy. The excitement= alone doesn't close deals=E2=80=94only clear, measurable business outcomes= do. If your pitch doesn=E2=80=99t explicitly show how your product moves a= needle the customer values, your sale will stall. "Interest" without a con= nection to business value is a dead end. Another common pitfall is assuming customers can intuitively connect your p= roduct features to their business outcomes. They won't do that heavy liftin= g=E2=80=94it's your job to clearly demonstrate the link. You need to bridge= the gap between excitement and actionable value clearly and explicitly, he= lping your prospects see the direct path from your solution to their bottom= -line outcomes. So, how do you pinpoint exactly what value means for your customer? **The Three Pillars of Real Business Value** When you're selling, there are only three core pillars your solution should= clearly tie to: * **Make More Money:** Accelerating revenue growth, increasing sales veloci= ty, enabling upsells or expansions. This could mean reducing sales cycles, = improving conversion rates, or unlocking new revenue streams. * **Save Money:** Boosting efficiency, improving productivity, reducing ope= rational costs. This involves clearly quantifying how your product reduces = labor, overhead, or other measurable expenses. * **Decrease Risk:** Preventing losses, ensuring compliance, reducing uncer= tainty and protecting reputations. Risk is often overlooked but can be an e= xtremely compelling reason for a prospect to buy=E2=80=94particularly in re= gulated industries or where reputation and stability are critical. Your solution must clearly map onto one or more of these pillars to resonat= e with real decision-makers. Identifying these pillars in your own product = isn't guesswork=E2=80=94it starts with effective customer development. If y= ou=E2=80=99re still building out your product, incorporate the following qu= estions into your future interviews to make sure you=E2=80=99re setting you= r future salesperson-self up for success. If you have an established produc= t but you=E2=80=99re struggling to close deals, I recommend sitting down wi= th your existing customers and asking them these questions.=20 **Use Customer Development to Uncover Real Value (Three Magic Questions)** Your customer development conversations aren't just about validating your p= roduct=E2=80=94they lay the groundwork for your future sales process. Your = goal is to find people with unmet needs that are worth solving. The first t= wo questions help you quantify the size of the unmet need and the last one = helps you understand how solving it would tie to one of the core value pill= ars: 1. **Importance:** =E2=80=9COn a scale of 1-10, how important is solving th= is problem to you?=E2=80=9D Dive deeper here=E2=80=94why is it important, a= nd how does it impact their broader business goals? 2. **Satisfaction:** =E2=80=9COn a scale of 1-10, how satisfied are you wit= h how you're currently solving this?=E2=80=9D Probe further by asking about= specific pain points or gaps that their current solution leaves unaddresse= d. 3. **Impact:** =E2=80=9CIf you solved this, what would the impact be on you= r business?=E2=80=9D Encourage them to quantify this impact explicitly. Pus= h them to tie this specifically to making more money, saving money, or decr= easing risk. The answers to these questions will clarify exactly which pains your custom= ers care most about solving=E2=80=94and how urgently they need solutions. I= t will also guide your product roadmap, making sure you're building feature= s that your market truly values. Once you clearly understand these value insights, the next critical step is= integrating them directly into your sales process. **Turn Customer Development Insights into Your Discovery Process** Insights from customer development should directly shape your sales discove= ry conversations. Think about it this way, you invested time interviewing 5= 0, 100, 200 potential customers and understanding where the gaps are. They = showed you their problems and why they=E2=80=99re a priority. Now, we need = to use what we learned about our typical buyer to determine whether the pro= spects in our funnel are a good fit for us right now. Your goal in a discov= ery process isn't simply to check off the qualification boxes=E2=80=94it's = to build a concrete business case that your prospect can confidently presen= t to their internal stakeholders. Without real, numerical evidence of your = solution=E2=80=99s value, it=E2=80=99s nearly impossible for prospects to j= ustify buying from you internally. Remember, no one buys software for the sake of "good vibes." They buy solut= ions that have a meaningful impact on their business. To help prospects mak= e the right decision, you need to be able to clearly articulate the value y= our software provides and ask questions that uncover whether it aligns with= their goals. But! Not all people that are in pain care about solving it.=20 I once hit a speed bump in my old Jetta that knocked a hole in my exhaust. = Any mechanic would say that I should fix it - and I knew that too - but I s= imply didn=E2=80=99t have the time. I was aware of the problem but I didn= =E2=80=99t care about solving it right now. The people you meet in a sales = process will be the same, so when you=E2=80=99re conducting your discovery,= it=E2=80=99s important to try and understand where they are in their buyin= g journey. Are they aware of the problem? If so, do they care about solving= it? Here=E2=80=99s how to categorize potential buyers.=20 * **Problem Unaware:** Prospects who don=E2=80=99t realize they have an iss= ue. Your task: educate first, gently guiding them from unawareness to aware= ness by clearly illustrating the hidden costs or missed opportunities they = face. * **Problem Aware but Don=E2=80=99t Care:** They acknowledge the problem bu= t aren't motivated to fix it immediately. Your approach: understand what wo= uld need to change for it to become a priority and then keep in touch.=20 * **Problem Aware & Motivated:** They recognize the problem and want to get= it solved. These are your ideal buyers=E2=80=94prioritize these conversati= ons and provide clear, compelling evidence of how your solution directly re= solves their urgent pain points. Being aware about your prospect's buying mode helps you understand how to s= erve them best. While I=E2=80=99d love to say that I=E2=80=99ve had great s= uccess changing people=E2=80=99s buying mode, the reality is that people ra= rely change their perception of reality based on a sales conversation. The= best you can do is ask good questions and find a way to support them as th= eir thinking evolves. Their muffler might be hanging on by a thread but the= y don=E2=80=99t care because the engine is on fire. The more you uncover in= the sales process, the better equipped you=E2=80=99ll be to understand whe= ther a deal is going to move and how / when you can make an impact.=20 **Conclusion & Takeaways:** Before your next call, run this quick value checklist: * Do I clearly understand which pillar of value (make money, save money, de= crease risk) my product addresses? * Have I quantified the business impact to clearly build my prospect=E2=80= =99s internal case? * Do I know which buying mode my prospect is in, so I can adjust my sales s= trategy accordingly? Remember: If you can't clearly tie your product to real business value, you= don't have a deal. Make every sales interaction count by ensuring your pro= spects see, feel, and can confidently communicate the concrete business val= ue your solution offers.=20 Happy closing,=20 Collin=20 PS - my latest product market fit journey episode just came out, this one h= ighlights Kathleen=E2=80=99s journey with Ecomedes. Check out the [blog pos= t](https://predictable.fm/kathleen-egan) here / our the episode on [Spotify= ](https://open.spotify.com/episode/51vfVNzWIhtpf4jStR9nJC).=20 =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-deals-die --c406880a3e98072fd07407fb4ebd9513e039487e56ab035af7bcea99234e Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset=utf-8 Mime-Version: 1.0 why deals die
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March 28, 2025   |   Read Online

<= h1 style=3D"text-align:left;font-family:'Trebuchet MS','Lucida Grande',Taho= ma,sans-serif;font-weight:Bold;font-size:32px;color:#2A2A2A;padding:2px 0;l= ine-height:38px;"> why deals die
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The Three Pillars of Real Business Value

<= /td>= = =

Hello Andrew,

Q= uick book update: I=E2=80=99m on my final round of copy-edits for the book = and should be shipping those off early next month. Once I=E2=80=99m finishe= d there, I=E2=80=99ll be ramping up the = pre-sales c= ampaign.

Most founder-led sa= les calls start great=E2=80=94prospects love the demo, they're excited = about the product, and the conversations leave you feeling confident. But t= hen...nothing. The deals stall, fade away, and no one pulls out their credi= t card. The reason? You haven't clearly connected your product to real,= measurable value that your prospects genuinely care about.

What Founders Get Wrong About Value

<= span style=3D"color:rgb(44, 62, 80);">Too many founders mistake enthusiasm = for intent. Prospects might rave about your cool features or innovative tec= h, yet still never buy. The excitement alone doesn't close deals=E2=80= =94only clear, measurable business outcomes do. If your pitch doesn=E2=80= =99t explicitly show how your product moves a needle the customer values, y= our sale will stall. "Interest" without a connection to business = value is a dead end.

Another comm= on pitfall is assuming customers can intuitively connect your product featu= res to their business outcomes. They won't do that heavy lifting=E2=80= =94it's your job to clearly demonstrate the link. You need to bridge th= e gap between excitement and actionable value clearly and explicitly, helpi= ng your prospects see the direct path from your solution to their bottom-li= ne outcomes.

So, how do you pinp= oint exactly what value means for your customer?

When you're selling, there are only thre= e core pillars your solution should clearly tie to:

    = Make More Money: Accelera= ting revenue growth, increasing sales velocity, enabling upsells or expansi= ons. This could mean reducing sales cycles, improving conversion rates, or = unlocking new revenue streams.

  • Save Money: Boosting efficiency, improving producti= vity, reducing operational costs. This involves clearly quantifying how you= r product reduces labor, overhead, or other measurable expenses.

    =

  • Decrease Risk: Pr= eventing losses, ensuring compliance, reducing uncertainty and protecting r= eputations. Risk is often overlooked but can be an extremely compelling rea= son for a prospect to buy=E2=80=94particularly in regulated industries or w= here reputation and stability are critical.

Your solution must clearly map onto one or more= of these pillars to resonate with real decision-makers. Identifying these = pillars in your own product isn't guesswork=E2=80=94it starts with effe= ctive customer development. If you=E2=80=99re still building out your produ= ct, incorporate the following questions into your future interviews to make= sure you=E2=80=99re setting your future salesperson-self up for success. I= f you have an established product but you=E2=80=99re struggling to close de= als, I recommend sitting down with your existing customers and asking them = these questions.

Use Custom= er Development to Uncover Real Value (Three Magic Questions)

=

Your customer development conversations are= n't just about validating your product=E2=80=94they lay the groundwork = for your future sales process. Your goal is to find people with unmet needs= that are worth solving. The first two questions help you quantify the size= of the unmet need and the last one helps you understand how solving it wou= ld tie to one of the core value pillars:

  1. Importance: =E2=80=9COn a scale of 1-10, how important is solving this problem to= you?=E2=80=9D Dive deeper here=E2=80=94why is it important, and how does i= t impact their broader business goals?

  2. Satisfaction:<= /span> =E2=80=9COn a scale of 1-10, = how satisfied are you with how you're currently solving this?=E2=80=9D = Probe further by asking about specific pain points or gaps that their curre= nt solution leaves unaddressed.

  3. Impact: =E2=80=9CIf you solved this, what would th= e impact be on your business?=E2=80=9D Encourage them to quantify this impa= ct explicitly. Push them to tie this specifically to making more money, sav= ing money, or decreasing risk.

The answers to these questions will clarify exactly which pai= ns your customers care most about solving=E2=80=94and how urgently they nee= d solutions. It will also guide your product roadmap, making sure you'r= e building features that your market truly values.

Once you clearly understand these value insights, the nex= t critical step is integrating them directly into your sales process.

Turn Customer Development Insights = into Your Discovery Process

I= nsights from customer development should directly shape your sales discover= y conversations. Think about it this way, you invested time interviewing 50= , 100, 200 potential customers and understanding where the gaps are. They s= howed you their problems and why they=E2=80=99re a priority. Now, we need t= o use what we learned about our typical buyer to determine whether the pros= pects in our funnel are a good fit for us right now. Your goal in a discove= ry process isn't simply to check off the qualification boxes=E2=80=94it= 's to build a concrete business case that your prospect can confidently= present to their internal stakeholders. Without real, numerical evidence o= f your solution=E2=80=99s value, it=E2=80=99s nearly impossible for prospec= ts to justify buying from you internally.

Remember, no one buys software for the sake of "good vibes.&q= uot; They buy solutions that have a meaningful impact on their business. To= help prospects make the right decision, you need to be able to clearly art= iculate the value your software provides and ask questions that uncover whe= ther it aligns with their goals.

= But! Not all people that are in pain care about solving it.

I once hit a speed bump in my old Jetta that kn= ocked a hole in my exhaust. Any mechanic would say that I should fix it - a= nd I knew that too - but I simply didn=E2=80=99t have the time. I was aware= of the problem but I didn=E2=80=99t care about solving it right now. The p= eople you meet in a sales process will be the same, so when you=E2=80=99re = conducting your discovery, it=E2=80=99s important to try and understand whe= re they are in their buying journey. Are they aware of the problem? If so, = do they care about solving it? Here=E2=80=99s how to categorize potential b= uyers.

  • Problem Unaware: Prospects who don=E2=80=99t realize they have an iss= ue. Your task: educate first, gently guiding them from unawareness to aware= ness by clearly illustrating the hidden costs or missed opportunities they = face.

  • Problem Aware but Don=E2=80=99t Care: They acknowledge the problem but aren&= #39;t motivated to fix it immediately. Your approach: understand what would= need to change for it to become a priority and then keep in touch. =

  • Problem Aware & Motivated: They recognize the problem and want to get it solved. These a= re your ideal buyers=E2=80=94prioritize these conversations and provide cle= ar, compelling evidence of how your solution directly resolves their urgent= pain points.

Bei= ng aware about your prospect's buying mode helps you understand how to = serve them best. While I=E2=80=99d love to say that I=E2=80=99ve had great = success changing people=E2=80=99s buying mode, the reality is that people r= arely change their perception of reality based on a sales conversation. The= best you can do is ask good questions and find a way to support them as th= eir thinking evolves. Their muffler might be hanging on by a thread but the= y don=E2=80=99t care because the engine is on fire. The more you uncover in= the sales process, the better equipped you=E2=80=99ll be to understand whe= ther a deal is going to move and how / when you can make an impact. =

Conclusion & Takeaways:

Before your next call, run this quick val= ue checklist:

  • Do I clearly understand which pillar of v= alue (make money, save money, decrease risk) my product addresses?

  • Have I quantified the business impact to clearly build my prospect= =E2=80=99s internal case?

  • Do I know which buying mode my pro= spect is in, so I can adjust my sales strategy accordingly?

    • =

Remember: If you can't clear= ly tie your product to real business value, you don't have a deal. Make= every sales interaction count by ensuring your prospects see, feel, and ca= n confidently communicate the concrete business value your solution offers.=

Happy closing,

Collin

PS - my latest product market fit journey episode just came out, this on= e highlights Kathleen=E2=80=99s journey with Ecomedes. Check out the blog post here / our the episode on Spotify.

<= /td>
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