The Secret to Asking Sales Questions Assertively, Not Aggressively



Questions are some of the most valuable tools in a salesperson’s arsenal. With a well-crafted inquiry, reps can open their prospect’s mind to a new possibility, compel them to action, discover relevant information, or secure buy-in for the next step.

But if reps ask questions aggressively, they won’t get that far.

Instead, they’ll alienate prospects or even anger them -- and unsurprisingly, angry prospects aren’t eager to talk.

The silver lining? There’s a simple test for differentiating between aggressive and assertive questions.

How to Tell an Aggressive Sales Question From an Assertive One

When attempting to determine whether a question is aggressive or assertive, length is your first clue. In general, longer questions usually feel more aggressive than assertive ones. When the salesperson leads with intent or context, prospects can feel pressured to respond a certain way. Getting right to the point, on the other hand, makes prospects feel like they can answer however they’d like.

That brings me to the second indicator -- the format. Aggressive questions start with the rep’s reasoning and then segue into the actual request, like so:

“It’ll probably take less time if I speak to your HR department myself. Who should I contact?”

Compare that to a question that cuts to the chase:

“Is anyone in HR assigned to this area?”

The first variation comes across as far more pushy. The decision to speak to HR sounds like a foregone conclusion, because the rep has introduced their reasoning first. The salesperson is also taking for granted their choice is the right one for the buyer -- and that’s a dangerous assumption to make.

The second variation leaves room for the buyer to introduce an alternative (like talking to HR herself, or suggesting a different contact), enabling buyer and rep to come to a mutually agreed-upon next step.

The Formula For Assertive Sales Questions

Reps can turn an aggressive question into an assertive one by asking it in one sentence. This rule forces them to cut out all preface, leaving only the core ask.

Here’s an example:

Before:“The events team will definitely want to come to the demo so they can evaluate our offering too. When would be a good time for all of us to meet?”

After:“Is there a good time for you, me and the events team to meet for a demo?”

Of course, the salesperson should provide an explanation if their prospect requests it. Imagine that in the above scenario, the buyer says, “Wait, why should the events team attend this meeting?”

The rep might reply, “If the events team manages their mobile bookings through the tool, it would free up operations to focus more attention on assisting your team.”

With that context, the buyer can either approve the events team’s attendance, or say it’s not necessary.

There’s an added benefit to asking one-sentence questions. When reps keep their queries short, they never fall into the trap of nervous rambling. It’s easy to accidentally ask a two, three, or even four-part question -- but doing so can easily confuse or even overwhelm a prospect.

Seasoned salespeople usually find that brief, focused questions keep the conversation on track and decrease potential hesitation. While it can feel awkward or rude at first to immediately get to the heart of the question, the more reps practice this technique, the more comfortable they become.

Walking the line between assertive and aggressive takes effort -- and the way salespeople ask questions is just one aspect. However, if you want to project confidence, involve your prospect in the decision-making process, and keep them focused, it’s always best to stick to single-sentence questions and skip the upfront explanation.

For more of Jeff’s advice and expertise on sales prospecting and management techniques come see him live in San Francisco on 10/17 or in Boston on 10/24. Learn more.

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