Salespeople are curious by nature. You have to be -- if you genuinely have no interest in learning more about your prospect’s business, you’ll have to spend every day fighting your instincts to do your job. And when you spend your entire day fighting your natural instincts, it’s not likely you’ll be successful.
Curiosity is a crucial trait. Sales qualification -- the process by which you learn more about your prospect and their business -- is the only way you can make tailored recommendations for their businesses and the only way you can provide value. We all know that salespeople who don’t provide value don’t make sales -- ergo, to make sales, you must be curious.
But curiosity can go too far. While you can find out a ton of information about your prospect and their business online and through tracking prospect activity on your website, you’ll never get a complete picture just by reviewing online activity.
That’s why the best salespeople enter calls with prepared questions and a few assumptions about the prospect’s business that they’ll as their point of contact to confirm or deny. They’ve prepared just enough to come up with informed questions that’ll actually drive the conversation forward, instead of asking about banal details they could have easily discovered themselves.
Unfortunately, many of the best salespeople get so excited about their list of questions that they immediately shoot themselves in the foot.
I’ve heard it happen a hundred times on live sales calls and in call reviews. The salesperson will start out with a great open-ended question that will reveal a key business challenge or goal. They take a breath. And before the prospect can respond, the rep asks four more questions.
It sounds something like this:
In my research, I found out that you have separate recruiters assigned to each department at your company. How does each team source candidates? Was there a specific reason for dedicating recruiters to specific teams, and do they work well together? Do you have an internal communication system to track all candidates in one place, or does each department have their own system?”
Whoa. This salesperson clearly has done their research and has an assumption about the recruiting structure at his prospect’s company, but he’s trying to do too much. In one sequence of questions, he’s trying to find out six pieces of information:
- How recruiters find and work with candidates
- The rationale behind assigning recruiters to specific teams
- Whether there’s any communication among recruiters assigned to specific departments
- Whether that communication is productive or not
- Whether there’s an overarching candidate tracking system in place
- Whether each department has its own specialized process for recruiting
That’s six different pieces of information necessary to start forming an educated recommendation to this product. But because this salesperson asked the questions in this way, he probably won’t get more than one or two key points.
If you ask questions like this, you’re hurting your deal in four major ways.
Why Salespeople Should Only Ask One Question At Once
1) You’re making assumptions.
Asking multiple sales questions at once inherently contains assumptions. An effective line of questioning unearths one piece of information at a time, then builds upon that information with more questions. You should always be prepared to pivot your questioning strategy based on the answers your prospect provides, and asking multiple questions at once prevents you from doing so.
It also comes off as presumptuous to prospects. Asking a lot of follow-up questions is essential to discovering their challenges, and prospects are usually happy to give you more detail when prompted -- after all, they want your help too. But asking a string of questions without even waiting for one response tells the prospect you care more about confirming your own assumptions than keeping an open mind and learning about their situation.
2) You’re overwhelming prospects.
Read that example again. Can you imagine getting on a call and being asked for six different pieces of information in a row, some of which might not even be relevant to you? It’s completely overwhelming for prospects to be posed with this many queries at once. Some might tell you to reiterate one question at a time, but many will be polite and just attempt to answer everything in one fell swoop. The result? You won’t get a complete answer.
3) You’ll have to repeat yourself multiple times.
If your prospect doesn’t try to answer every question at once, they’ll ask you to repeat your questions, one by one. Not only will you have to recall the entire sequence of requests, you’ll also be putting your prospect in an uncomfortable position. Right off the bat, they’re revealing that they weren’t able to follow you -- which can make them embarrassed, defensive, and feeling like they have less power than you in the conversation.
Save yourself some time and your prospect some grief, and ask questions one at a time.
4) You’re priming your prospect to give you a certain response.
The multiple-questions approach often rears its head when you’re asking a question with multiple possible responses. For example, the sales team I work with consistently asks prospects about their sales processes -- specifically, where prospects get new leads and how they follow up with them. There’s multiple possible answers -- maybe the prospect has a steady stream of inbound leads and follows up with a predetermined email and call sequence. Maybe they’re cold-sourcing leads and following an outreach playbook. Maybe they have no process in place at all.
It’d be easy to fall into the trap of naming these options after asking, “Where are you currently finding leads and how do you follow up with them?” But doing so primes prospects to answer questions a certain way. A prospect with no sales process who’s embarrassed by his lack of sophistication is more likely to make up an answer to make himself sound better if you’ve already provided him options of what a sales process could look like.
Prospects who do follow a certain process might omit parts of it, and just respond, “Yes, I do X.” The second you start answering your own question, you automatically build walls around the prospect’s answer because you’ve anchored them to the options you’ve already provided, and you’ll learn less as a result. Keep things open-ended by asking one question and shutting up.
Restraint is the mark of a seasoned salesperson. You won’t be successful until you can keep quiet and let your prospects’ answers guide the sales conversation, rather than trying to drive and damaging your ability to make an informed recommendation in the process. So start asking better sales questions today.