Riddle Me This Please Sales Leaders…

This post is about asking better sales questions – the answer to the riddle below is one of them.
Here’s a riddle for you?
We explore without traveling. We make a point without telling.We discover the pain and the pleasure, the truth and the lies.We are not to be judged by our sound or our size.We are what salespeople need, want and hardly use.We are what buyers expect to share their views.What are we? [Answer at end of page]
If there is only ONE thing that is THE most important task salespeople have to do well, that MOST are not doing at all, it is asking carefully constructed questions with a purpose.
It’s time to forget the cliche of ‘open and closed’ questions because if the truth were known, we hear that phrase and don’t really understand what is behind that curtain, or even care to understand.
But by understanding the background to questions, makes a HUGE difference to the way salespeople interact, qualify and create relevance.
There are SO MANY different kinds of questions and with buyers not wanting to be ‘sold’ and by salespeople wondering what else they can do to differentiate themselves further without ‘selling’ per se, it’s important we consider a more conscious approach through guided, coaching instead.
Anyone who is au fait with a true coaching style, as opposed to a managed style, will know that it is all about creating the rapport and trust for someone to be open enough . From there it is reliant on really great quality questions – some designed to discover, some designed to simply make you think and others designed to challenge.
Here are a few different categories of questions found in any good coaching manual and from my own experience as someone with a Diploma in all things coaching – business and personal, past sales and business coach for APAC for Anthony Robbins, and Board Certified from USA, I can vouch for these questions contributing to some pretty powerful outcomes.
First a word of warning:
Be careful of any question that starts with WHY, no matter how innocent and well meaning the question. WHY will put anybody into a subconscious defensive and justification mode.
These are some of the categories of questions you might ask instead:
Power Questions that move somebody up into a bigger purpose and away from specifics:
- What can we do to shift this?
- What do you think is not effective and what might turn that around?
- What is your outcome?
Purpose Questions are similar to Power Questions but are focused more on the bigger picture:
- For what purpose are you wanting this meeting?
- What is the intention of this discussion?
- What would doing xyz give you?
Possibility Questions will lead someone to think about doing something versus them thinking they can’t
- If you could do xyz, then what would that allow you to then do?
- If you were able to meet with the buyer, what do you think that would lead to?
- If you could do this without failing, then what would you do next?
Necessity Questions are the opposite to Possibility Questions and are designed to focus on what has to happen in stead of what might happen.
- What must you do to turn your results around this month?
- What do you specifically need from me to help you move this forward?
- What is the next action you absolutely have to take?
Laser Questions cut straight to the chase
- What is stopping you picking up the phone right now?
- What will get you from here to there in the shortest possible time?
- How are you sabotaging your time management in this moment?
Kaizen Questions which come from the Japanese concept of continuous improvement through small steps
- What is one extra call you could make?
- What is the next conversation you could have?
- If you were to stretch your thinking just a bit, what direction would you go?
Questions all all have a part to play in the effectiveness of communication, clarity and qualification.
As you can see some of these are closed questions and some of them are open questions so by not exploring the different types of questions we leave ourselves short and therefore leave multiple opportunities on the table.
Your task is to take each category and create a couple of new questions that will form part of your toolkit to better serve you and your buyer. Is that a great idea?
No question about it!!
5 Habits for Asking Better Sales Questions
Asking better sales questions is less about memorising a list and more about which mode you are in: discovering, provoking thought, or challenging. Most salespeople only ever use the first one.
The salespeople who get noticeably better at asking better sales questions usually make one change first – they stop planning their next question while the buyer is still answering the last one.
If you want your team genuinely asking better sales questions instead of running through a script, Bernadette McClelland’s keynote presentations are built around exactly this coaching-style approach.
Asking better sales questions is a skill you can practise in any conversation, not just sales ones – which is exactly why it improves so fast once you start noticing it.
I’m Bernadette – founder of the Decision-Led Revenue™ Operating System and The Revenue Leader of Influence™, where I work with CEOs and sales leaders to build a sales team they can rely on to think, make the call, tell the truth about pipeline and own the result.
If any of this resonated – or if you’re staring at a revenue problem that feels like it should have been solved by now – I’d love a conversation.
BOOK A NO-OBLIGATION 20-MINUTE CALL
And if you’d rather join the discussion, you can also join me on Substack. That’s where the Revenue Leader of Influence community is starting to have these conversations in real time.






