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The one skill that all entrepreneurs desperately need

Founder & Editor in Chief at Collective Hub

05:06 | Sep 19 , 2016 | Lisa Messenger -Startup

The one skill that all entrepreneurs desperately need

I ask questions all the time. All the time. About everything. To everyone in my path. On just about any topic. I can’t help myself… I have a curious mind!

But, I’ve discovered asking questions is not only a window for personal reflection and betterment, it’s also one of the most powerful weapons available to us as innovators and entrepreneurs – and it doesn’t cost us a thing. One of my favourite sections of any speaking gig is the Q&A at the end. I know some speakers who quake, and actively avoid this finale: ‘What if someone asks me a question I don’t have a smart answer to?

What if I don’t fully understand the question and say something stupid in return? What if I freeze or am hit with something controversial that I would have preferred to think through in-depth and rehearse my answer for?’ Not me, I don’t think like this. For me personally, I love Q&A time because it’s the most honest, authentic and revealing part of any speaking gig, and is often when the best breakthroughs happen. No matter how successful you are, if you stop questioning yourself, your purpose and your place in the world, that’s when stagnation happens. Sometimes, you need a total stranger to stand up in a conference centre and ask you, “But, why?” to pause your mind, remove any hype and get you to honestly ask yourself the same thing. Asking questions – and the right ones – is not a new concept, but nevertheless it’s so crucial to our success in life and business.



Motivational speaker Tony Robbins says, “Quality questions create a quality life. Successful people ask better questions and as a result get better answers.” I also love this quote from British author, James Allen: “For true success ask yourself these four questions: ‘Why? Why not? Why not me? Why not now?’” I’ll never forget hearing Ashton Kutcher speak at an innovation event recently, where he talked about his love of questioning. “Great questions cause us to sit for days and ponder a solution,” he said. “Great questions expose problems and problems are the seeds to solutions. Great questions expose roadblocks which are an entrepreneur’s opportunity. A great question sometimes will arrive at a no, which is the playground for a rebel’s spirit.” How amazing – and true – is that? If you don’t ask, you don’t get – that’s something I truly believe. I’m not just talking about questioning yourself constantly, but also your staff, your acquaintances, your friends and other people in your industry.

It helps you understand more and think through things at a deeper level, but it also shows others you are genuinely interested in them. A lot of people think they ask questions but they don’t, really. We ask small-talk questions, which scratch the surface: ‘What did you do at the weekend? Are you going on holiday this year? How’s your partner?’ But, we don’t always delve further and ask the insightful questions we can actually learn from, like, ‘Why did you choose to spend your free time doing this activity?’, ‘How did you balance work while you were abroad?’ or ‘What is it about your partner which makes you feel uplifted and whole?’ We worry that we’re ‘overstepping’ or probing too deeply. But it’s the other person’s prerogative how much they wish to reveal in their responses, and you’ll usually find most people are happy to talk about themselves if they have an authentically interested audience (rather than someone who is clearly just waiting for you to stop talking, so they can start again). The art of questioning takes practice but is the most powerful tool you can have in your repertoire. How do you get better at asking questions? Good question! Here are my top tips:


I first read this advice on an online forum for teachers. It warned that, typically, teachers ask their students questions which the teacher already knows the answer to. And, even as the student is answering, the teacher is really just thinking about the response they would have given. It’s an interesting point for leaders who can be held back by ego – you ask what you know because you don’t want to appear inexperienced. But admitting to your team, “I don’t know the answer to this but I’d love to explore it together,” shows you still want to learn and grow.


In psychologist and creative thinking expert Edward de Bono’s book How To Have A Beautiful Mind , he dedicates an entire chapter to the art of questioning, and the different types – aside from shooting questions (when you’re looking for a ‘yes’ or ‘no’) and fishing questions (an open-ended search for information), questions can be used to check on the validity of a statement (“is that your direct personal experience?”) or used to search for possibilities (“What are the alternatives? Would you consider this?”). He also says questions should be used to investigate someone’s value system, by asking their view on a current affair or global crisis. If your questions usually only fall into one category, strive to mix it up a little. 


What do you look like when you’re listening? I know it sounds funny, but it’s an important factor in successful questioning. Some people just have terrible listening expressions: eyes flitting to things going on in the background, unable to meet the speaker’s gaze.

Most body language experts seem to be in agreement that you should aim to make eye contact for 30-60 per cent of a conversation. Oh, and don’t ask a question and then start scrolling through your phone whilst the other person is responding… no matter how tempting.


In the adventure documentary 180° South, with Patagonia founder Yvon Chouinard, it said that, “The best journeys answer questions that in the beginning, you didn’t even think to ask.” I think an enlivened conversation works in the same way – allow a question to lead to answers that go in a completely different direction. One minute you’re talking about company culture, then you veer into religion, love, sex, spirituality and end up talking about the price of avocados. The best conversations are freeflowing, spontaneous and unpredictable. You never know at the start where you’ll end up.


In 2015, Oxford University released a list of the most obscure questions that tutors ask candidates during course application interviews. They included, “Ladybirds are red. So are strawberries. Why?” and, “If the punishment for parking on double yellow lines were death, and therefore nobody did it, would that be a just and effective law?” Meanwhile, students who applied for the university’s psychology course were asked, “What is ‘normal’ for humans?” and given no further direction. After all, if you ask the same questions all the time you’re likely to get similar answers – and where’s the fun in that? 


I have a friend who routinely asks people in his industry, “What was your biggest career f**k-up?”. He particularly likes to ask anyone who has been working in the field for more than a decade, “because no one gets to that point without having some colossal uh-oh moments.” There are so many reasons this is a brilliant question, especially when meeting new people: it’s humbling and reassuring and it’s a perfect icebreaker. Just make sure you give as good as you get and share a f**k-up of your own (with a good sense of humour).

Lisa Messenger is the CEO of The Messenger Group, as well as founder and editor-in-chief of Collective Hub™, an entrepreneurial lifestyle magazine distributed in over thirty-seven countries with a mandate to disrupt, challenge, and inspire. In addition, she has worked globally in events, sponsorship, marketing, PR, and publishing. Lisa has authored and coauthored over a dozen books, including her latest Daring & Disruptive: Unleashing the Entrepreneur.