Salespeople rarely lose complex deals because they forgot to follow up. They lose because they never developed a clear hypothesis about how the decision would be made, who would influence it, and what each stakeholder needed to believe. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey explain how a practical deal plan helps an AE move beyond the purchasing contact, understand the full buying committee, anticipate competitive threats, and coordinate the internal resources required to win. Using examples from sports, construction, manufacturing, and distribution, they show how disciplined planning improves sales execution, pipeline velocity, and long-term account growth.
Key Topics Discussed
Why Every Important Opportunity Needs a Deal Plan — 00:00
Kevin compares deal planning to the preparation elite athletes complete before taking the field. Great players do not simply understand their own position; they study their competition, anticipate likely reactions, and enter the game with a strategy. The same principle applies to B2B sales. A written deal plan increases the likelihood of closing the opportunity faster, executing more effectively, and avoiding preventable losses.
Turning Assumptions into a Written Sales Hypothesis — 01:23
Sean explains that salespeople function as the quarterback of the opportunity. They must determine what they will do, how their teammates will contribute, and how the overall sales process should unfold. A sales hypothesis makes those assumptions visible: who will buy, what problem they are trying to solve, who benefits, and what conditions must exist for the deal to advance. If the hypothesis is not written down, it cannot be tested, improved, or consistently executed.
Looking Beyond the Transactional Buyer — 02:32
A purchasing contact may control the transaction without receiving the greatest value from the product. Sean uses an HVAC compressor example to illustrate the broader stakeholder network: procurement, contractors, electricians, installers, building owners, maintenance teams, and eventual occupants may all influence the decision. Effective value selling requires messaging that addresses each stakeholder's priorities—not merely the requirements of the person issuing the purchase order.
Understanding Decision Criteria and Stakeholder Influence — 05:05
Kevin expands the discussion through construction and engineered-specification sales. Manufacturers may need to influence architects, engineers, distributors, contractors, materials managers, and procurement teams long before an order is placed. Product specifications, installation requirements, availability, regional codes, service levels, and delivery capabilities can all become decision criteria. Strong business acumen allows a seller to connect those operational details to the buyer's desired outcome and measurable ROI.
Mapping the Buying Committee and Informal Relationships — 08:32
Studying competitors is not enough. Salespeople must understand everyone "on the field," including the individuals who benefit from the solution, those who may resist it, and those who influence one another behind the scenes. Sean recommends creating a simple visual stakeholder map: write down the names, circle them, and connect the people who communicate, have worked together, attended school together, or maintain trusted relationships. Mapping the buying committee helps expose the informal decision network that a CRM contact list alone may not reveal.
How Deal Plans Evolve into Account Plans — 10:45
A single stakeholder map supports one opportunity. Repeated deal plans reveal patterns across the account. Over time, the seller develops a record of who influenced previous decisions, why stakeholders supported or resisted the solution, and how internal relationships affected the outcome. That knowledge becomes the foundation of an account plan, giving sales management and Revenue management teams a stronger platform for expansion, retention, and more predictable revenue generation.
Key Quotes
Kevin Lawson — 00:57
"If you're not doing deal plans for your next deal, you're probably missing an opportunity to either close faster or more effectively, or you might even be increasing the chances that you're going to lose."
Sean O'Shaughnessey — 01:44
"You are the quarterback of the team. Your job is to figure out what all of your teammates are going to help you do, but also what you're going to do."
Kevin Lawson — 05:41
"It's just your opinion about who's going to buy, who it's going to benefit—which may be a different person—and then what are the other related people that could have influence over the deal?"
Sean O'Shaughnessey — 09:15
"You need to understand everybody on the court, everybody on the pitch, everybody on the field."
Sean O'Shaughnessey — 12:02
"Before long, your deal plans are becoming account plans."
Additional Resources
B2B Sales Lab
The B2B Sales Lab is a place where sales professionals and sales leaders can continue developing practical tools for deal planning, account planning, and navigating complex deals. www.b2b-sales-lab.com
A Significant Actionable Item from this Podcast
Choose one of your five most important active opportunities and create a one-page stakeholder map before your next sales meeting.
Write down every person who may buy, use, approve, implement, support, oppose, or benefit from your solution. Circle each name and draw lines showing formal reporting structures and informal relationships. Beside each stakeholder, record four things:
-
What outcome does this person want?
-
How will this person evaluate the decision?
-
Whom does this person influence?
-
What evidence or messaging does this person need from you?
Then identify the most important relationship you have not yet developed. Define one action that will help you reach that person directly or through an existing contact. This simple exercise turns an opportunity record into an executable deal plan and gives your VP of Sales or sales leader something concrete to coach.
Summary
Winning an Enterprise Sales opportunity requires more than activity, product knowledge, or a strong relationship with procurement. The salesperson must understand the full buying committee, recognize the informal lines of influence, align the value proposition with multiple decision criteria, and create a written hypothesis for how the deal will be won. In this episode, Kevin and Sean provide a practical framework for navigating multi-stakeholder deals without adding unnecessary complexity to the sales process. Listen to the episode to learn how a blank sheet of paper, a few circles, and the right questions can sharpen your sales strategy, improve B2B sales pipeline predictability, and turn individual deal knowledge into a scalable account-growth system.
B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com
You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/
You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/
You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin
You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/
