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3 Key Questions to Win the Complex Sale

Great B2B salespeople focus on the right deals and leave unqualified prospects for reps who are content spinning their wheels.

Have you ever analyzed exactly why you lost that last key deal?

One thing that great business-to-business salespeople do on a consistent basis is focus on the right deals. They seem to have a built-in GPS system that enables them to accurately and effectively assess their current sales opportunities. They don’t waste their time chasing every deal that’s placed in front of them. They can quickly examine 10 deals and determine which ones should receive their immediate attention and which ones can easily be placed on the back burner. They are masters of qualification.

3 Compelling Qualification Questions

There are three compelling questions that should be used throughout each sales campaign to help qualify the opportunity. Things change. People change. As a result, salepeople should not just qualify early, but often. The three compelling questions are:

Should we pursue this opportunity?

Is this project or application (associated with this sales opportunity) connected to a key business initiative and has funding been approved and allocated? Do you understand the client’s business drivers, business initiatives and the driving reasons for the client to change or make a decision to implement this project or application, or is the client simply gathering information?

Developing an in-depth understanding of the client’s business, their key customers and competitors is an important aspect of this question. Since time and resources are limited, it’s important to determine that the opportunity being assessed is real and represents a worthwhile investment in time and resources.

Can we effectively compete for this opportunity?

Solution fit is one component of whether you can be competitive in a sales campaign. Are there enough internal or external resources available to compete successfully for the business? Are there existing business relationships established with the client? Does your solution offer specific business value that enables you to differentiate yourself from your competitor(s)?

Knowing how your company, as well as your solution, relates to the specific sales opportunity can be a key ingredient to winning the deal. Being able to realistically contrast that information with that of your competitor(s) is an important factor when assessing this compelling question.

Can we reasonably expect to win this opportunity?

This is the most important question, yet it’s the one that is most often overlooked in sales campaigns. Many opportunities are lost even if the salesperson has the best solution, the best delivery and even the best terms and conditions. This question deals with how well the salesperson understands the client’s organizational structure that ultimately allows them to identify the inside support necessary to win the deal.

The answer to this compelling question also reveals which key executives wield the most power and influence within the client organization, as it relates to this sales opportunity. Most importantly, the salesperson must determine the relevant executive associated with the opportunity – as outlined above – the executive who stands to gain the most or lose the most as a result of the application or project associated with the sales opportunity.
Do the most powerful people in the client’s organization want you to win? Do you have credibility with the client’s key players? Most importantly, is there political alignment with the key players in the client organization who either affect or are affected by the buying decision? Finally, what facts support these assessments of your client relationships?
Contrasting these factors with that of your competitors can have a significant impact on your decision to continue to pursue a sales opportunity.

These three compelling questions, and the underlying criteria, should be asked multiple times during a sales campaign. They should certainly be asked near the beginning of a campaign to determine if a legitimate sales opportunity exists and should be pursued. They should be asked again if there’s a significant change to the client’s business profile or to the competitive landscape during a sales campaign. It might also be appropriate to pose the questions again if there is a major change to the profile of the sales organization (i.e., the introduction of new solutions).

Examining each of these three compelling questions at multiple times during a sales campaign can be compared to an airline pilot examining a pre-flight checklist. No matter how many times a pilot has flown a certain plane, he or she meticulously examines that checklist before each and every flight, probing each question, using an exact, non-negotiable approach.  The pilot clearly doesn’t want to be surprised midflight and does not want to leave anything to chance because the stakes are too high.

Salespeople must use the same approach in a sales campaign. Nothing can be left to chance. They have to not only know the information they have, but the information and intelligence they are missing. That can only be accomplished by applying a structured, repeatable methodology that sales reps have internalized and apply consistently.

Top-performing salespeople clearly demonstrate the proven paradigm that executives don’t buy because they understand, executives buy when they feel they are understood. What do those top performers know that most salespeople don’t?

Key Reasons for Losing Deals

Recent surveys have indicated the four key reasons that salespeople lose deals are:

  • Lack of relationships at the executive level
  • Client is unconvinced of the service provider’s level of commitment and/or credentials
  • No clear strategies exist to effectively address the executive’s risk sensitivity
  • Inability to effectively articulate a compelling value proposition that accelerates the client’s goals, objectives or aspirations

You’re may be wondering why price didn’t make the list. Price is not on the list because anyone can be a winner for a day. It’s called a discount. Funny thing about offering rock bottom prices, once you hit bottom, there’s nowhere else to go. But that won’t stop your clients for asking for more. There are very few deals that cut to the bone to win a client that have been able to keep that same client long term. To consistently win, you’ve got to demonstrate value above and beyond the price point.

Keys to Winning Sales

If you want to take your sales to the next level, here are a few things you can do today to make sure you win more deals tomorrow.

  1. Begin to expand those executive-level relationships in the client organization. Start by identifying the relevant executive for the sales opportunity and identify the other key players of power and influence. Consider focusing only on your top opportunities to see how this approach might be of value to you. This represents a good first step to implementing a consistent, repeatable process for all major sales opportunities.
  2. Look to learn as much as you can about each client’s business, their customers, their competition and their industry so that you can begin to deliver value to each one.  Take the steps necessary to elevate your level of knowledge, as well as your business relationship, with several key clients so that you can see the benefits of those efforts. Then apply those same techniques to all of your top sales opportunities.
  3. Examine the specific ways you can begin to mitigate the risks associated with the solutions you propose to your clients. Look at how you can demonstrate to the client executive that you alone have the ability to mitigate any risks associated with the implementation of a value-driven solution.
  4. Begin to develop compelling, provocative value propositions that demonstrate the return on investment your solutions can provide to your clients. Start with a focus on some key deals where you can clearly articulate and differentiate your solution from that of your competitors. Share your value propositions with your sales team and challenge them to provide you with suggestions to improve them.

Leverage the techniques described in this article to enhance your relationship with senior executives in the client organization. By so doing you will significantly increase your chances of closing those key deals!

Free Webinar on Accurate Sales Forecasting

Stephen J. Bistritz is presenting a webinar for on how to get more reliable sales forecasts from salespeople. The webinar, sponsored by Sales & Marketing Management, will be at 2 p.m. Eastern on Thursday, June 17. For more information and to register, click here.


  • Stephen Bistritz has more than 40 years of high-tech sales, sales management and training management experience. He is a published author and lecturer in the field of sales, sales management and selling to executives and is the co-author of the 2nd edition of "Selling to the C-Suite."

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Stephen J. Bistritz
Stephen J. Bistritzhttps://www.sellxl.com/
Stephen Bistritz has more than 40 years of high-tech sales, sales management and training management experience. He is a published author and lecturer in the field of sales, sales management and selling to executives and is the co-author of the 2nd edition of "Selling to the C-Suite."

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