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Ask tough questions


Regardless of what selling system you use (SPIN, MEDDPIC, Challenger, Sandler etc.) they all rely on one vital ingredient. Asking tough questions. Not just any question, tough and challenging questions.

They can be hard to answer. In my world the question might be something like “So when your salesperson didn’t do what they were supposed to do, what consequences did you impose as part of your accountability process?” Most business owners would want to crumble under that. There’s so much in that question that they would not want to face: they probably don’t know what their salesperson should be doing and don’t want to admit that; they don’t want to face up to the fact the salesperson has gone rogue; they have never imposed any sanctions of any kind because they want to rely on their salesperson and don’t want to lose them; they don’t want to admit they don’t really hold them accountable; and they certainly don’t want to admit that they have zero process when it comes to sales management. Alright, hard tough question to answer.

However, how hard is it to ASK such a searching, potentially fraught and downright accusatory question? After all we know they haven’t done anything about the situation. We know that because this is just one of many examples they can give. The problem isn’t that we suspect we are asking a poor question that will land miles from the bullseye. The problem is the reverse; we know that this is precisely where it hurts. When you ask the question it will hurt. As the “diagnosing doctor” you have to ask in order to be able to help. You need to ask, but it will hurt. Hurt them and be very uncomfortable for you to ask.

How can you make it easier to ask?

The most obvious way is to ask permission. It’s like that “diagnosing doctor” again. If your doctor suddenly yanks your suspected dislocated elbow you’d not be pleased. However, if your doctor gently asks, “Can I examine that elbow? This might hurt a bit…” then you’d proffer your elbow with confidence. So do the same here. “Can I ask you a difficult question? You might not like it but it would help to know how to advise you.” In fact, you could miss out that second bit. Just “Can I ask you a difficult question?” is often enough. If you feel you are going to go too far you could say “Can I treat you as if you were a client of mine and ask you a tough question?” or even more extreme “I might just be about to talk myself out of a deal here, but can I ask a tough question?”

Once you’ve asked permission a few times, the prospective client will have got into the habit of answering tough questions and feel you are doing your professional best to assist them so you can just keep on going. So long as you occasionally check in with them about how they’re feeling. “Is this alright? I know I’m asking some uncomfortable questions here.”

Be not afraid of conflict when asking tough questions. Ask permission. Check in with them occasionally. And ask the tough questions! (You owe it to them.)

When you had training on asking tough questions, what form did that take? When you are ready for help, if you are in Surrey, Sussex, Berkshire, Hampshire or Kent, contact me on 07866 518848 or email me

Paul Glynn

Paul Glynn

Sandler trainer