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The Magical Power of Questions

Have you ever questioned yourself (pun very much intended), on how you could be more effective in different situations, be it work or play, professional or personal relationship?

If you have, then consider this a cheatsheet for getting more out of almost every situation by taking one very simple action…

Substitute statements for questions.

Not in every situation of course. This isn’t Succession where Logan Roy’s underlings are pathologically incapable of giving their own opinion before asking what his is…I doubt anybody is aspiring to be Tom W in real life.

Yet in more contexts that you’d realise, a question can be more powerful than a statement when it comes to improving your outcomes from a particular interaction.

Here are 8 examples of situations where that’s typically the case.

1. Unlock budget and win deals

From a sales perspective, the most obvious place to replace statements with questions is during the initial ‘discovery’ or ‘qualification’ call…the clue is in the name!

But for many organisations (and reps) the initial meeting is actually a demo or pitch meeting, and can frequently be devoid of questions Instead the time is taken up by a sales rep running through the rubber stamped deck full of statements that prospects don’t care about, from ‘we were founded in x’ or ‘we’re based in y’ to ‘we’re the [unverified] leader in z’.

Instead of leading with assumptions about their challenges, or statements about how great your company is, replace them with gently probing, open ended questions like:

  • Can you tell me more about your company and its current priorities?
  • What challenge is going on that is driving those priorities?
  • What metric(s) are suffering because of that?
  • What blockers are you experiencing in resolving that challenge and achieving your priorities?
  • How have you attempted to solve these challenges in the past?
  • What’s your take on the reason the business is experiencing this challenge?
  • Can you walk me through your current workflow or processes related to this challenge?
  • If you solved it, what would good look like? How would you measure success?
  • What criteria are you using to evaluate potential solutions?
  • What are your expectations from a vendor or partner like us?
  • Who else in the organisation is feeling this pain?
  • What is your timeframe for implementing a solution?

This is a non-exhaustive list…and remember discovery calls shouldn’t be a 1-way interrogation and your questions should be interspersed with observations, mini case studies and industry knowledge. 

But asking the right questions will unlock the real pain felt by prospects, then uncover the implications of not solving it, and weed out the root cause (which then puts you in the position of a trusted provider). This is how great deals are won.

2. Build credibility

Following on from the above point, asking the right questions is a sign of expertise and genuine understanding.

There’s a common (and I believe true) perception that if you can summarise a prospect’s pain better than they can, they’re far more likely to trust you with being able to deliver the solution.

That’s captured in this great quote from ​​Wyatt Wood Small, who said: “When you can articulate another person’s problem better than they can, they automatically and unconsciously credit you with knowing the solution.”

Leading with a bunch of statements that may be missing the mark is effectively playing the lottery and hoping one sticks, whilst asking open-ended questions gives you the context needed to articulate the problem better than they can.

And you don’t need to be an analytical genius to do this either…here’s a super simple trick. Next time you’re in a discovery call and they share an answer, simply say ‘Thanks for sharing. So what I’m hearing is…[repeat back in your own words what they said]. Did I get that right?’

This simple approach signals to them that you listened (and understood) and gives you the ability to re-articulate the problem in a way that now makes you sound expert in understanding it!

And if you didn’t get it right, that’s no issue either…it avoids any crossed wires and gives them a chance to correct you.

3. Unlock your team’s potential (and your own)

This is one of my favourite ‘life hacks’ which works beautifully with teams but also on yourself.

If you’re faced with a challenge, most statements will be limiting or unhelpful.

E.g. I could never run a 4 hour marathon (limiting) or I’m going to run a 4 hour marathon (nice, but not particularly instructive)

Much better is to reframe the statement into a question…’how could I run a 4 hour marathon’ or ‘what would it take to…’

When speaking to direct reports, when they come to you with a limiting statement ‘I’m too busy’ or ‘this is too complicated’ why not reframe it: ‘what would it take to free up time’ or ‘how could you break it down to simplify things’?

You’ll be amazed at how the subtle shift empowers them (and you!) to overcome those limiting beliefs and find a way.

4. Build your network (and friendships)

Who wants to be friends with the motormouth in the room that can’t stop talking about themselves? Just about nobody!

Yet when we’re in a room full of new people, we often feel intimidated by their perceived achievements or social status (particularly at networking events), and so our ego kicks into self-defence mode and we spend most of the conversation trading statements about how worthy we are of the others’ attention.

It’s generally a recipe for both parties coming away with the impression that the other person thought a lot of themselves and there wasn’t really a connection there.

Better to swap out your statements (and quiet the ego), and instead ask probing questions. 

What was that like? How did you get into that? What would you recommend to a beginner?

By showing interest in the other person, you’ll form a much closer bond more quickly. 

Of course, this isn’t an interrogation (as per the previous point), and you should balance your questions with your own narrative (ideally related to the topic being discussed), but lead with your curiosity (and actually listen to their responses rather than trying to queue up your next impressive accomplishment). You’ll be delighted with the results.

5. Learn new things

A wonderful byproduct of taking the above approach is that you’re likely to learn a thing or two. You can even taken the best stories you hear and repurpose them for your own yarns in the future (“I was speaking to this person at an event the other day and you’ll never guess what happened…”)

More challenging is if you hear something that jars with your current world view. The typical reaction to this is to ‘prove’ they’re wrong with more ‘factual’ statements of your own.

But if you take the time to hear them out with an open minded perspective, you’ll find that you learn new things at a rapid rate. And even if your original viewpoint hasn’t changed, you’ll have a more expansive view of the issue.

6. Resolve arguments

So many arguments (or disagreements), particularly in the workplace, are caused less by people holding opposing views than by miscommunication. Often there’s more common ground than differences, but the words used to convey one anothers views are not interrogated by the other person.

This means they’re interpreted differently than intended, and a wall is put up. Imagine how many conflicts would be resolved if, instead of answering a statement with another…

‘I think this’… ‘hm interesting, well my view is this’

…it was met with a clarifying question ‘I think this’ … ‘hm interesting, can I just clarify, by this do you mean x, y or something else’?

The result of this approach is 3-fold:

Firstly, the person feels listening to, which will immediately bring down any initial guard they were putting up.

Secondly, you’re actually forcing them to think through their own logic (which isn’t always well defined in situations that call for rapid decision making), a real benefit to everyone.

And thirdly, you are ensuring that your understanding/interpretation of what you just heard is indeed accurate.

Turning the statement to a question = win win win. Triple threat!

7. Get better outcomes from negotiations

Similarly to helping diffuse arguments, asking questions instead of trying to get your position heard, is a great to walk out of negotiations much better off.

There’s a whole book on this – Never Split the Difference (highly recommend!) – but to take one key takeaway, try this…

Next time someone is making you an offer that doesn’t work for you, instead of saying ‘no’ or ‘that doesn’t work for me’ try asking a ‘how’ question e.g.

‘How am I supposed to do that?’ or ‘How would that work’? 

This leads to several positive outcomes:

  1. It Signals Collaboration: By asking “How am I supposed to do that?” instead of outright rejecting the offer, you demonstrate a willingness to engage in a problem-solving mindset. It indicates that you are open to finding a solution that works for both parties.
  2. Encourages the Other Party to Reevaluate: This question prompts the other party to reconsider their offer and potentially propose alternative options or concessions. It shifts the burden of finding a workable solution back to them.
  3. Forces Clarity and Specificity: When the other party is asked to explain how they expect you to meet their offer, they are compelled to provide more details and potentially reveal any underlying motivations, constraints, or hidden interests. This additional information can be valuable for further negotiation and finding common ground.
  4. Buys Time: By responding with a “How” question, you gain a moment to think and strategize while keeping the conversation going. It prevents premature closure of the negotiation and allows you to gather more information before making a decision.
  5. Maintains Emotional Calmness: Using the “How” question can help prevent an overly adversarial or confrontational atmosphere. It keeps the conversation focused on problem-solving rather than escalating tensions.

Not bad for a simple question!

8. Impress your boss

Last but not least for this post, don’t forget to question your boss.

No…not question their judgement (as much as you might like to!), but ask clarifying questions when they’re giving you new work or projects to take on.

Instead of saying ‘sure I’ll get that done’ take a few minutes to calibrate expectations, check what good looks like, timeframes, who else should be involved, where it sits on their priority list (and how that translates into yours), how involved they’d like to be kept…

In just 5-10 minutes, there’s every chance you’ll save yourself and your boss hours of lost productivity and rework, exasperation (from both parties) and disappointment. 

Even better, by checking explicitly on prioritisation and sharing your current workload, and checking what they’d suggest you bump off the list or deprioritise, you may find the work goes away! 

And if it does land on your desk, you’ll be equipped to deliver killer results that meet their expectations. Winner!

Next steps

Next time you hear a statement (or find yourself making one), ask yourself this…would the situation benefit from a question?

More likely than not, the answer will be yes.

I’d also love to hear your favourite examples of questions that have driven better outcomes in business or in your personal life!