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12 Questions Sales Leaders Must Ask to Improve Sales Opportunity Management

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Written by Mike Schultz
President, RAIN Group

If you've spent any time in complex sales, you know there's been a significant shift in how you win sales opportunities and grow accounts.

In our client work and studies through the RAIN Group Center for Sales Research, we've seen that:

  • Buyers are less patient. If sellers don't impress buyers immediately with their professional approach and competence, and continue to do so throughout all interactions, they get dismissed.

  • More sales are happening over the phone and Internet. At the same time, purchasing organizations are becoming more sophisticated, making it all the more difficult to build relationships with buyers.
  • There are more decision makers involved in every purchase and sellers are struggling to gain agreement among the full group of buyers—leading to longer sales cycles and more losses to 'no decision.'
  • Buyers have a heightened awareness of risk. They often prefer to run pilots, start small, and otherwise figure out how to test vendors before committing to larger agreements.

If sellers want to win in this environment, they must plan to win from the start. Anything short of this and they set themselves up for failure.

The sellers and sales organizations that consistently win get sales opportunity management right. They focus maximum energy on their most important opportunities and develop winning strategies for each sale.

If you want to join their ranks and improve your approach to sales opportunity planning, start with asking yourself these 12 critical questions:

  1. Does your team pursue your most important sales opportunities with high intensity and rigor?

    If they want to win, sellers need to build opportunity plans and execute them with energy, leaving no stone unturned. To inspire intense pursuit of the sale, you need a "Win Lab." A Win Lab is a collaborative, rigorous process to generate the best ideas, strategies, and action plans to win a sales opportunity.

    Read more: 4 significant characteristics of a successful Win Lab approach.

  2. Is the opportunity planning process collaborative?

    Sellers tend to create opportunity plans alone. The problem is that sellers (and people) are almost universally good at some things and not others. When they work alone, sellers make mistakes and miss key steps in the process. The real magic happens when the right players on the team collaborate to build a compelling opportunity plan.

  3. How strong is your sales process?

    It's tough to build a plan to move a buyer through a sales process if a seller doesn't know the process, or if it's not very good. According to our study, The Top-Performing Sales Organization, companies with a more mature sales process have higher win rates, discount less, and experience greater revenue growth. The first step to strengthening your sales process is to know where you are and then work on getting to the next level. Download Optimizing Sales Opportunity Management to learn more about the maturity levels.

  4. Is your opportunity management process customer-centric?

    Companies like to say they are customer-focused, but what they say and what's true often aren't the same. For example, popular opportunity plan templates contain prompts for seller mission, sales objectives, seller positioning, and so forth. It's difficult to have a customer-focused sales organization when the planning tools and prompts are overly seller-focused.

    Read more: 6 Elements of a Buyer-focused Opportunity Plan

  5. Do sellers assign a pursuit-intensity rating to their opportunities?

    Virtually all companies have limited resources and need to make tough decisions about which opportunities deserve the most time and effort. When you're analytical in how you rate the importance of each opportunity, you'll utilize your resources more effectively, investing the right amount in each opportunity and maximizing your wins.

  6. Do sellers leverage the right people and resources on your team?

    Sellers tend to miss opportunities to involve all the right people and resources, even in their biggest sales. Imagine the difference if sellers took full advantage of the following:

    • People with deep industry experience, executive-level connections, negotiation strength, inside knowledge, etc.
    • Resources at their disposal, including intellectual capital, case studies, presentation material, buyer-interaction opportunities, proposal checklists, sales messaging resources, and more.
  7. Are your opportunity management processes and tools customized to suit the dynamics of your sale?

    Some companies have individual sales in the tens and hundreds of millions of dollars. Others much less. Some companies sell in teams, with each person playing specific roles. Others don't have defined roles. Some companies have their own language around customers, their needs, company offerings, value propositions, sales messaging, and so on. Your sales process and opportunity management tools should be customized to capture what's important for your sale.

  8. Are sellers satisfying the buying criteria of multiple buyers?

    In today's complex B2B sale, sellers often find themselves selling to a team of 5 or more.1 We've found that the sellers who succeed most with decision making groups do two things: Identify buyers and categorize them into 5 decision roles; and facilitate buyer agreement (see the next question).

    Read more on the 5 decision roles in every sale and how to win over each.

  9. Do sellers facilitate agreement among buyers so the sale can move forward?

    The larger the buyer group, the more resistant they will be to change. At least one influential buyer must be inspired to put a stake in the ground and make a stand for moving forward: we call these buyers Change Champions. The best sellers motivate and equip Change Champions to advocate internally for them and their solution.

  10. Do sellers craft and communicate a compelling value case?

    If your opportunity plan doesn't include prompts for sellers to build a strong case for value for the buyer, chances are your sellers aren't doing it as well as they should. A good way to check if your value case is rock-solid is to ask these 4 questions.

  11. Do sellers plan in advance to inspire buyers with insights?

    The number one greatest difference between sellers who win and those who come in second place is that winners educate buyers with new ideas and perspectives—insight selling. Few sellers, however, plan in advance to create insights for buyers. With a little structure and support from management, they can.

  12. Are sales opportunity plans written, compelling, and built to win the sale?

    Creating sales opportunity plans is too often viewed by sellers as a chore: something to fill out quickly so they can check the I-filled-it-out box. If a plan is worth creating, it's worth creating properly—or you put the sale at risk. For your most important sales, plans should be rigorous and impressive. Once a plan is written, it increases the likelihood the seller will execute it, and it allows sales managers and others to challenge the plan, vet it, and improve it.

Sales leaders who consider these questions, and then install the discipline to approach sales opportunity management the right way, will find themselves on the path to greatly increased sales wins.


1. Kelly Liyakasa, "B2B Tech Buying Cycle Is 20 Percent Longer," CRM Magazine (Sept. 2012).

Last Updated March 29, 2023

Topics: Sales Management Sales Opportunity Management