The challenge

As salespeople, we’re 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 their prospects feeling unheard and misunderstood.

Poorly executed questioning

There are three primary reasons why salespeople execute their questioning poorly.

1. 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 this product learning too easily 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’re all too quick to jump into.

2. Time pressure

Most salespeople feel that they need to get to the deal as quickly as possible. The temptation is to *run* 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’s the slightest suggestion that the prospect could be interested. Even the limited questioning that is done often makes customers feel that they are being hurried into a “trap”.

3. 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, and no sense that their inputs are guiding the dialogue. Failure to listen is profoundly disrespectful and deeply irritating. In fact, in some ways, it’s worse than show-up and throw-up selling, which might (purely by accident) be valuable to the customer even if ineffective for the salesperson.

Questioning for understanding

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

1. 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 is your prospect 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 a sense of the individual(s) you’ll be talking to:

• What’s their background? How long have they been with the organisation? 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 organisation and the people you’re meeting. At best, you’ll sound patronising; at worst, like some kind of stalker. The objective is to ensure that you’re focused on the customer and their issues, you have some degree of empathy for their personal circumstances, and you’re ready to ask intelligent questions and understand their answers.

2. 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 discussions. There is no magical shortcut – it requires dedicated effort to build a calendar of prospect meetings, and strict discipline to prepare for them all adequately.

Without this effort and discipline, however, your funnel will look like a tube. You will be desperately trying to squeeze every meeting into a close. There’s no chance for good questioning technique to thrive in those circumstances.

3. 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 summarise what’s been discussed, both during the meeting itself and in subsequent follow-ups.
• 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:

1. 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). However, doing so sends the message that the top-of-funnel activity is not important.

2. 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.

3. 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.

4. Don’t reflexively snap into a presentation of your organisation’s structure, ownership, values, financial results and strategic goals.

This is as bad as the salesperson jumping into a product pitch.

5. 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.

6. Finally, work with salespeople to help them overcome confirmation bias.

Salespeople often seek out only information that supports what they want to believe – typically, that there’s a great opportunity they can win. Confirmation bias is the enemy of good qualification; it leads salespeople to 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.

To discover more about effective questioning techniques, let’s talk growth.