Win Planning Approach for Sales

“It’s not the will to win that matters – everyone has that. It’s the will to prepare to win that matters.” – Paul Bear Bryant, Former University of Alabama football coach (6 national & 13 conference championships)

New opportunities are exciting… the next big sale, blowing away quota, commissions…. That’s why when a new opportunity comes up, it’s very enticing to start rallying the troops and jumping in with both feet. In fact, with deadlines looming (and management adding pressure to get the deal signed before the end of the year/ quarter, etc.), it becomes very easy to cannonball into the pool before you grab your goggles or sunscreen.

With a simple transactional sale you may be able to get away with this, but if you are managing big deals with multiple buyers and complex solutions, selling becomes less of an isolated activity and more of a project with multiple team members, timelines, milestones, and buyers. In this case, the cannonball approach is definitely not effective, and can, in fact, be quite detrimental to the sales process. However, what we see time and again is that the pressure to sell (and sell now) can give even the most experienced salesperson the sense that action is more important than strategy and planning. They act and act until… they reach a gate… either they have an opportunity review coming up, they require internal approvals to move the deal forward, or they have to submit a proposal or develop a presentation. It’s at this point that they start pulling all of the pieces together… often during crunch time… and often with a lot of comments like “I wish we had…” and “we should…but it’s too late now.”

A win planning process can provide sales teams with the format and the structure they need in order to effectively get organized around a big deal. This process includes the development of a win plan, the use of an opportunity scorecard to assess the opportunity progress, and a cadence to ensure regular sales team communication throughout the opportunity lifecycle.

Win (or opportunity) planning has been around in many formal sales methodology approaches for almost 20 years but still continues to be a challenge with many sales organizations. Companies invest in deploying win planning processes, but without consistent reinforcement, the bias for action can quickly prevail, leaving win plans to catch dust on a shelf. That said, with the proper tools, coaching, and oversight, an effective win planning process can become engrained in the culture of any sales organization.


Win plans are tools that facilitate the organization required to effectively execute a complex sale. They are designed to ask the questions that guide the sales team to think about a coordinated set of strategies and tactics necessary to win, and they are also quite helpful in integrating new sales team members, SMEs, or executives into the process midstream. Win plans are working documents, which means that they should be continuously updated throughout the opportunity lifecycle – they are not intended to be static documents that are developed and put on the proverbial shelf. These plans often start out as a basic framework to get everyone on the same page, and they become more robust as the sales team learns more about the opportunity and further develops their win strategy.

Key components of a win plan should include…

  • A definition of the problem: What is the customer’s specific problem and overall scope of the opportunity? Are all of the customer stakeholders aligned on the definition of the problem? What is driving the customer to act now? Note that, in some cases, the sales team may see the problem but may first have to introduce insights that will help the customer come to the same conclusion. In this case, the team should both define the problem and outline a plan to bring the customer on board. Similarly, the sales team may need to create the sense of urgency for the customer and outline their plan to do this.
  • A win strategy: What is the solution that you can offer? How will you structure the deal? What is the value proposition? What win themes, or key messages, will you convey to the customer throughout the sales process? What supporting insights might you use to help the customer look at the problem in a different way or otherwise view your solution as unique?
  • A competitive analysis: Who are your key competitors? What is their strategic advantage? How can you win against them?
  • A stakeholder analysis: Who are the key customer stakeholders (buyers, influencers, gatekeepers, and the individuals who can override the decision)? What are their motivations and decision criteria? How can you gain access to them and structure an effective call plan to “win their vote” when it comes time to make a decision?
  • An internal alignment plan: What needs to be done internally to both sell the deal and deliver the solution? Who should play what roles in the sale?
  • A credential overview: How will you credentialize yourself with the customer? What is your history with the account and with delivering similar solutions? What references can you/should you use (if applicable), and who needs to secure these?
  • Closing logistics: What are the tactical items that must happen to close the deal (e.g., MSAs, NDAs, rate cards, etc.)? What is the decision timing and any key steps in the buyer process (e.g., proposal due dates, vendor conference calls, etc.)?
  • An action plan: Based on what is laid out in the win plan, what are the specific actions that the sales team should be taking to execute the win plan?


Opportunity scorecards are another critical component of the win planning process. They ask the simple question… “Does the customer evidence show that we are on the right track to win?” Like win plans, opportunity scorecards should be revisited throughout a lengthy, complex sale. There are many reasons for this:

  • The sales team may learn new information that changes the likelihood of the sale or the ability to meet customer needs
  • The buyer landscape may change, especially for considerably lengthy opportunities
  • The competitive landscape may change as competitors enter and exit and as key competitors begin to execute their own win plans

The opportunity scorecard should ask these fundamental questions:

  • Does the client have a clear need and an urgency to solve it?
  • Does the sales team have the right level of buyer access to help decision makers understand the value of the solution?
  • Does the proposed solution provide the customer unique value? Can the organization deliver the proposed solution?
  • Has the sales team met the necessary contractual requirements to sell to this account?
  • Is it a win-win? Is there enough value?

In order to develop an appropriate scorecard, sales teams should, using the questions above, outline the key factors that indicate an opportunity is moving in the right direction and standardize on a scorecard for the sales organization.

In order to ensure that the team answers scorecard questions objectively, the way an opportunity is scored should be based on customer evidence that clearly answers each question with yes or no, where customer evidence can be listed to support each yes and a strategy can be outlined to change any no response to a yes. If the sales team doesn’t know the answer to a scorecard question, it should be part of their action plan to find out. Sales leaders should regularly review opportunity scorecards and question the customer evidence that is driving the score in order to eliminate any optimistic bias that may preclude the sales team from seeing the need to take corrective action or re-evaluate whether to pursue the opportunity.


A cadence is a regular series of activities and calls/meetings with defined objectives, roles, and tasks. In the overall business of sales, sales leaders and managers should run regular cadence events to review pipelines, account planning efforts, and other tasks critical to running the sales organization. In the case of complex opportunity management, cadence provides the opportunity for leaders to contribute and add value to their most important sales. Each big deal should have an opportunity cadence, facilitated by the opportunity owner.

The opportunity cadence defines when the team is going to discuss the opportunity, the role each person involved in the sale will play in the win planning process, and how/when updates to the win plan and scorecard will be made. An opportunity cadence is critical to ensure consistent oversight and coordination for opportunities that involve multiple team members who must work together over a long period of time to close a sale. This becomes extremely important when team members span multiple opportunities and have a variety of conflicting priorities.

For sales leadership, the cadence clearly outlines when sales leaders will participate in the process and how they will participate, whether they get involved at a gate in the process or for regular quality assurance. A defined cadence not only ensures that the team regularly communicates about the opportunity and makes the appropriate adjustments to continue advancing the sale (or to exit the selling process), but it also provides a vehicle for sales leaders to provide deal coaching, bring new perspectives to the deal, and assist in managing through any potential internal hurdles.


Without the proper deployment and oversight of the win planning process, win plans can easily be seen (and used as) an administrative task, rather than the tool that can facilitate proactive opportunity planning and management; and opportunity scorecards can be seen as performance reviews or metrics that need to be “gamed” in order to proceed with business as usual. In a similar manner, cadence can become a series of calls where people go through the motions or regularly cancel calls due to conflicting priorities. Following are a series of critical success factors for effectively implementing a win planning process:

Critical Success Factors that turn win plans into sales…

  • Establish guidelines for win plan creation. Recognize that not every opportunity requires a full-blown win plan. Some may require several bullet points, but more complex deals may require several pages. Ensure the level of effort put into the win plan is proportionate to the size of the opportunity.
  • Standardize on where to store win plans. Win plans become great communication vehicles and historical documents of record. Don’t lose them on a salesperson’s hard drive. Standardize on a central place to store both working and completed win plans.
  • Start the win plan as soon as the opportunity is identified. Recognize that the win plan will be incomplete at this point, but use the unknowns to plan your next steps.
  • Involve multiple players in the win planning process … either develop a draft and ask others to review it, or facilitate a session with key sales team members to jointly develop the win plan.
  • Establish roles and a regular cadence for managing the win plan. Who will own/contribute to the plan, how will updates be communicated to the team, how will you track progress, when will you meet to discuss win plan progress?
  • Regularly update your opportunity scorecard to manage whether you are moving in the right direction. Score yourself based on customer evidence – what the customer is doing or saying that proves you are advancing the sale. Depending on your scorecard analysis…
  • Don’t be afraid to (thoughtfully) change course. If moving your scorecard to green requires changing your win plan, consult with others, make the tweaks, and move forward. Since you won’t have all of the information at the beginning of the opportunity, it makes sense that your win plan will live in draft format until the deal is signed. As long as tweaks are intentional and are for the purpose of advancing the sale in the right direction, you should not feel like a win plan has to be set in stone at the outset.
  • Always question whether your scorecard is asking the right questions. You may not get it right the first time. If the questions in the scorecard make it impossible to say yes right up until you close the deal, perhaps you aren’t asking the right questions. At this point, regroup as a team and re-evaluate your scorecard.
  • Use the win plan to communicate internally about the opportunity. If you have to use the plan as a communication vehicle, you will ultimately put more thought into it, and you will have one document of record on the opportunity.
  • Use your win plan as input to your win/loss analysis. After you have closed a significant opportunity, it is wise to do a win/loss (or post-mortem) analysis. Your win plan document will serve as a valuable input to reflect on your strategy and how it ultimately played out in the sale.


A number of sales process methodologies emerged in the late 1980s and 1990s as standardized best practices for assessing, strategizing, and managing complex sales opportunities. These sales methodologies included Jim Holden’s Power Base Selling, Miller Heiman’s Strategic Selling®, Mike Bosworth’s Solution Selling®, Art Jacobs’ and Alston Gardner’s Target Account Selling® (TAS), and numerous others.

Each of these methodologies had slightly different questions and tools, but ultimately, the objective was the same – create a common way to converse and organize around a complex opportunity. Our point of view around win planning is that you should review standard tools and objects to determine core components and best practices but that you should configure a solution that aligns and adjusts uniquely to your company’s different sales teams and selling situations. You can dial-up or down certain components, depending on the needs of the sales teams, but we recommend that you maintain a consistent vocabulary that has your sales team talking the same language, regardless of the sale. By creating your own win planning process, you will create a way to win that becomes a unique competitive advantage for your organization.

Rolling out win plans is not easy. We see clear evidence that, even though win planning methodologies have been around for 20+ years, many people still aren’t using them consistently today. Consider, however, a recent study that shows that going from a random sales process to a defined sales process can improve your win rate by over 10%. Of course, the act of stepping back from a sale in order to develop a strategy and plan can seem counterintuitive, especially when the energy and excitement is high. However, the discipline to prepare to win can help ensure that you take advantage of all that you can bring to the sale so that there will be no regrets when you yell “Cannonball,” take the plunge, and go after the sale.

Download This Point of View Whitepaper in PDF Form: Symmetrics Group Point of View – Win Planning