The Challenge

As salespeople we are constantly being told that we need to ask customers and prospects “the right questions”. Yet – despite years of training in different questioning techniques – salespeople still leave customers feeling that salespeople have a poor understanding of their needs.

When the challenge is so well known, why has so little progress been made? And what can salespeople – and sales leaders – do about it?


Poorly Executed Questioning

There are three primary reasons why questioning is poorly executed.

– Preparation: very often salespeople feel that the best way to prepare is to master the fine detail of the solutions in their sales portfolio. That’s not intrinsically wrong; of course customers expect salespeople to have a good level of domain expertise. But very often this product learning displaces the essential preparation that focuses on the prospect, not only their business but their role within the business. By rehearsing their product pitches instead of researching their customers, salespeople establish a question-free comfort zone that they are all too quick to jump into.

– Time pressure: most salespeople feel that they need to get to the deal as quickly as possible. The temptation is to quickly walk through some cliched openers (“Where would you like your business to be in 12 months’ time?” “What do you feel is holding you back?”) and then immediately snap into presentation mode to “progress the sale” as soon as there is a hint that the prospect could be interested in something in the portfolio. And even the limited questioning that is done often makes customers feel that they are being walked into a “trap”.

– Listening: when the salesperson’s intent is to get to the product PowerPoint as quickly as possible, it’s no surprise that they barely listen to the answers to their questions. Customers quickly sense that their replies are falling on deaf ears – there are no clarification questions, no notes being taken, no sense that their inputs are guiding the dialogue. Failure to listen is profoundly disrespectful and deeply irritating: in some ways this is worse than show up and throw up selling, which might (if only by accident) be of value to the customer even if ineffective for the sales person.


Questioning for Understanding

There are some pretty simple steps to take to improve your questioning techniques and the effectiveness of your sales calls.

Prepare properly. There’s a fine line between asking open questions and being irritatingly ignorant. Good preparation is more than just taking a flick through your customer’s “About Us” on the way to the meeting. Get a sense of the customer’s overall context:

— What are the general issues being faced by the sector as a whole? How are they positioned relative to their competitors?

— What do their customers say about them? Are there review sites you can take a look at? Any common themes in customer feedback?

— What do their employees say about them on Glassdoor?

— Who are their main vendors? Have they published any case studies with them?

It’s also important to get some sense of the individual(s) you’ll be talking to:

— What’s their background? How long have they been with the organization? How long have they been in their current role? Someone 30 days into a new role is likely to have very different concerns and priorities from a person who’s been in post for 3 years.

— Do you have common points in your LinkedIn network? Is there someone you can contact to get more detail?

— What are the general issues being faced by someone in their function (HR, Sales, Operations, Finance …)?

The goal of good preparation is not to show off how much you know about the organization and the people you are meeting: at best you’ll sound patronizing, at worst some kind of stalker. The objective is to ensure that you are focused on the customer and their issues, you have some degree of empathy for their personal circumstances and are ready to ask intelligent questions and understand their answers.

Build your sales funnel. Premature closing attempts (and inadequate qualification) are not a cure for insufficient forecast coverage. Having a broader sales funnel gives you the mental space to pull back from the driving behaviours that squeeze out good questioning and kill off meaningful follow-up discussion. There is no magical short-cut – it requires dedicated effort to build a calendar of prospect meetings, and strict discipline to prepare for them all adequately.

But without this, your funnel will look like a tube and you will be desperately trying to turn every meeting into a close. No chance for good questioning technique to thrive in those circumstances.

Take notes. Keep your laptop shut, your phone on silent and get out your notebook and pen. Start by putting the date of the meeting and the names of the attendees at the top of the page. When the customer is talking, write down the key points.

It’s the simplest technique and yet it serves so many important purposes:

— It forces you to listen properly, rather than preparing your next questions while the customer is speaking.

— It shows customers that you are genuinely interested in what they have to say – a very important signal of respect.

— It creates a logical mechanism for you to ask clarifying questions: “I’m sorry – what was her name?”, “When is the project due for completion?”, “How many people are going to be impacted?” and so on.

— It enables you to summarize what’s been discussed, both during the meeting itself and in subsequent follow-ups.

— And – last but not least – it helps you remember what happened.


The Role of Sales Leaders

Simple is not the same as easy. Sales leaders need both to demand the right behaviour and to model it:

– Set aside time to work with salespeople on their prospecting. It’s all too easy to focus only on the deals that are near closure (and in the forecast) – doing so sends the message that the top of funnel activity is not important.

– When accompanying a sales call, make time to have the salesperson present their preparation beforehand. Share LinkedIn connections to find ways to contribute to the preparation process. Ensure that you are as well-prepared as they are.

– Let the salesperson lead the call. When they ask questions, let the customer answer – don’t jump in with additional questions before they have a chance to reply.

– Don’t reflexively snap into a presentation of your own organization’s structure, ownership, values, financial results and strategic goals. This is as bad as the salesperson jumping into a product pitch.

– Take notes in the meeting, and compare notes with the salesperson afterwards. When the salesperson is leading the meeting, sales leaders have an excellent opportunity to capture points that might otherwise be missed.

Finally, work with salespeople to help them overcome the confirmation bias that so often leads them to seek out only information that supports what they want to believe – which is typically that there is a great opportunity that they can win. Confirmation bias is the enemy of good qualification; it leads salespeople to search only for confirming evidence, prefer evidence that supports their beliefs and ignore opportunities to test their understanding.

Sales leaders have a little more distance from the immediate opportunity, and can ask the testing questions that truly qualify it.


Bill Bauer, Director of Product Development

Contact Bill on if you’d like to know more about questioning techniques. All call us on +44 (0) 207 653 3740

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