As a business owner, I have been asked a lot of questions by well-intentioned salespeople. In my time coaching and mentoring people, I have also heard these same questions pop up quite a lot. 

In most cases the people who ask these questions don’t really understand why, in many cases, they actually aren’t great questions to ask. Of course they are asked with the best of intentions, but unfortunately they don’t have the desired effect; quite the opposite, in many cases. Here’s the top five I’ve come across, along with some suggestions of what you can ask instead. 

Can I send you a proposal?

Other variants of this are “Can I send you a credential statement or a brochure?” The other person, whether they are interested or not, will likely say yes. Most people say yes even when they don’t want a proposal because it is easier than saying no, and there is no commitment on their part.

What happens in this sales scenario is that you go back to the office, pour your heart and soul and no doubt a little sweat and tears into a beautiful document – that your intended client never reads. You then spend then next few months chasing them, and they keep ignoring you. It’s because is they were never interested in the first place.

What you could ask instead: if it has come to the point in the conversation when they are talking about your offer and how it might help them, why not ask them, “What do you see as the next steps in our discussion?” Give them the control to decide if they want to explore your offering any further. Even if they don’t, you’ll have benefited from saving yourself a lot of time, they’ll appreciate that you haven’t wasted theirs too.

What do you think about the price?

I’ve recently been asked, “Is there anything else you need from me to help with your decision? How about the price?” Straight away you’ve opened the negation door for your buyer to beat you up on price. Even if you are dealing with someone who buys on value, this question will move them into deal-hunter mode, and their behaviour will change. They’ll most likely ask you to sharpen your pencil to help get the deal done. You may feel like this helped bring the deal in, but your impatience or desperation means this customer is likely to always expect a lower price.

What you could ask instead: if you’re looking for feedback try asking something like “How do you see X, Y or Z helping you with your business goals?” If you’re in the negotiation stage, simply ask them “What do you see as the next steps?”

What can I tell you about today?

Sometimes phrased as “Do you know anything about my company?” These questions will lead you into an uninformed, push-based sales conversation in an instant. The person you’re meeting is dreading these questions, because they know that is your lead-in to whip out your slide deck or company brochure, and talk at them about how awesome you are. Their eyes will no doubt glaze over and at the end they’ll say “Thanks, we’ll be in touch”. And we all know what that really means.

What you could ask instead: rather than take control and punch your message, ask them “What would you like to talk about today?” Perhaps even ask them “What are your 6 month or 12 month goals?” After all, you can’t really help them if you don’t know what they are trying to achieve.

What keeps you awake at night?

Classic sales question this – looking for their ‘pain points’. Firstly, it certainly conjures up an image – it makes your client think of big worries, restless nights and waking up sweating, full of anxiety. This isn’t a happy or productive place for your mind to be in, so why would it be for your client? They also start to associate you with their pain. If you want a trusted partner relationship with someone, do you think that will materialise if they associate meeting you with being in pain? I’d say very unlikely.

What you could ask instead: Why not ask them “How’s business going?” From that response maybe then ask, “Is there anything that could be going even better?” It’s a much more positive way of finding out their main challenge, without making them think of worry or sleepless nights.

Are you the decision maker?

This is usually not received very well. Variants of this include “Perhaps you should invite your boss to the next meeting?” There’s really only one way the person you’re meeting can take this. They’ll assume that you think they don’t have the clout you are looking for, and so you don’t really want to waste your time with them. This is certainly the wrong approach. In this situation, you need to build the trust with the person that you are actually meeting so that they offer to take you to whoever the true decision maker is.

What you could ask instead: “What are the next stages for you in this process?” Notice I haven’t asked “how can I help you get this through?” That is again, very pushy, and about you trying to control the situation. In this case, they are deciding how they proceed.


Ben Paul is a coach, facilitator, mentor, and director of The Business of Trust New Zealand.


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