I’m quite privileged to meet and interact with executives from an extensive array of sales solution companies, at all stages and strategies of development, experiencing various levels of success. During those interactions we discuss how to really put the sales pedal to the metal, and it has everything to do with traction.

More often than not, they have a worthy product, with great potential. But, like bald tires on ice, they’re trying and failing to get the company moving forward with too few people and less-than-adequate resources. After 10 or 12 months, they invariably reach out for some form of help.

At this stage, they’ve recognized that, despite wheels spinning, they’re not getting to their destination.

It can be difficult in these situations to know where to start. And so I’ll get this question, “What can you do to help us?”

What they’re really asking is “What do you recommend we do, and in what order?” Before I can begin to answer their question, I first ask several of my own.

Here are 15 key questions I might ask you in order to gain sufficient insight into your current situation, and to identify the prime opportunities for achieving positive traction.

Question Purpose
1. How many sales presentations have you given? This gives me a feel for where your focus is and where you are in your go-to-market plan.
2. How did you come to call on those prospects? This gives me great insight. Are sales calls occurring by happenstance? Are you deciding who the right prospects are before you begin calling? Are you contacting your industry colleagues first – regardless of the suitability – because it’s safe?
3. How many prospects have converted into opportunities Could there be a problem with the sales and marketing messaging, or the way it’s being presented?
4. How many opportunities have converted into deals? Are prospects interested, but unable to pull the trigger for some reason?
5. What does your ideal prospect look like? Are you casting too wide of a net or are you focused on the highest-probability prospects first?
6. What do you tell prospects about your solution or product? Are you making it too difficult for prospects to comprehend? Are you dumbing it down enough?
7. What do you ask prospects during a sales call? Are you helping your prospects discover the applicability and need for your product or are you telling them what they should think.
8. How do they respond? What reactions do you get? Do you get the same reactions each time? What are the most common reactions?
9. How are you differentiating your company or solution? Is it memorable? Will customers get it? How will they describe it to colleagues?
10. Where is the sales process getting stuck? Do your prospects like the idea, but resist follow-up meetings? Do you get to a proposal stage? What did the prospect need to do next, when the deal got stuck?
11. What are the most common misconceptions that prospects have? Misconceptions point to where the message is not being communicated effectively.
12. What shape is your website in? Are you confusing the heck out of your visitors? Are you offering information in a way that makes it clear where to start? Are there multiple opportunities to identify your visitors and entice action?
13. What is your elevator pitch? This tells me how concisely and clearly you can communicate your value proposition.
14. What are your prospect’s most significant alternative options for solving the problem? Other than “doing nothing.” Note: options often include non-competitive solutions.
15. What reasons do your prospects have for sticking with the status quo? Why would they not want to change?

By answering these questions, you can quickly detect where the trouble-spots are. In my experience, people are too close to the issue to be an objective observer. Often, they’ve hashed it out so many times, it’s difficult to look at it with a fresh mind. Asking very targeted questions such as these can help.

There are certainly other questions that can provide clues to where you should focus your attention, energies, and resources. But this is a great list to get you on your way. Whether you would like our help, or whether you choose to go it alone, answering these questions will help you recognize what the main challenges are, and which are the real obstacles on your road to success.