How to Ask Engaging Questions

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From an excellent discussion on Scott Gould’s blog, @juliewalraven raised that one of the biggest barriers most of us have for engaging, is the ability to ask probing, useful questions.  Which got me thinking…

Why is it useful to get good at asking questions?

For me it has been the key to breaking out of the 9 to 5 lifestyle and if your goal is generating discussion, then knowing how to ask the right questions to engage people becomes essential.  We have a tendency to stumble around looking for an answer to our problems before we know what the question is.  The net result is a lot of frustration and wasted effort.

Asking the right question at the right time has the added benefit of catching the ear of some very bright, and engaged individuals.  By building connections and sharing your question with a group, the result is a far better answer than stumbling towards a solution alone.

A solution is never complete.  There is always a hole, always an improvement.  If you’re one of those that can always spot a better way, ask the question and make the challenge because you could really help someone develop their idea.

Contribute, good things happen as a result.  What good things? Well My Storyis one where I challenged Senior Management to consider working with the new reality of Social Media Platforms.  They listened, and it significantly benefited my career.

How did I learn to Ask Engaging Questions?

Then a wonderful thing happened.  I noticed that experience in business knows how to ask questions.  My own personal mentor John, has a knack of asking a juicy question to get the brain whirring.  ’How does this benefit our customer? How do we monetise it? Is it right for us? What do we have to do to turn it into a product?’

Apply those questions to your Product or Blog, or try applying it to someone else’s and see if you can contribute and engage with them.  People notice when you add value to their passion.  Chris Brogan is the master of asking engaging questions that FORCE you to react.  Observe

How can you Ask Engaging Questions

Be critical, be cynical, be everything in-between, but when you’re done… be constructive with it.  We react to everything around us on some level, but do you challenge the world around you?  I always loved the EA Games slogan “Challenge Everything”.  Challenge everything, and be willing to be wrong.

Now take your top 5 mentors (whether they are aware they have that position or not), and see how they use questions to make people think.  Most of all try, do, ask.

How it will benefit you

My own story is fairly intertwined with having to learn the ability to ask challenging questions.  Perhaps yours is be too?  Can you look at the big picture, challenge the “way things have always been done” and bring a diverse option to the table?  If done in a constructive way, this is a very useful skill.

Have a go at challenging the world around you, and let me know how you get on.

Email me sy@sytaylor.net contact me on twitter@sytaylor or via facebook

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  • annholman

    Like the fact you've highlighted this! Engaging people in conversation doesn't actually come naturally do us. Well it possibly did when we were kids but then something called work conditioned it out of us.

    I think you are spot on when you say challenge everything. I'd even go further and say we possibly should be asking questions that are disruptive! Nothing more sure than that to get people engaged, as long as its in a supportive environment of course. Another point – why not ask the questions no one has asked before?

    Nice post!

  • http://www.sytaylor.net sytaylor

    Ann, not sure about your experience, but earlier on in my career the natural urge to challenge was beaten out of me. The new guy 'asking awkward questions' using the corporate Intranet was tough for my line management to handle. The result was they asked me to “Stop asking questions” and “Pick your battles”.

    My questions weren't always constructive or useful, but it would have saved a lot of time if they had simply taught me how to ask questions in a useful way. There is a danger in a lot of workplaces still, sadly that comes from speaking out. Learning who to ask takes some skill, and is a subject in itself… although it's probably 9/10ths instinct.

  • annholman

    Agree Sy, it was knocked out of me too. Then I was fortunate to work for a manager in Leeds for three years who didn't just encourage me to challenge but actually demanded it. Shock to the system though it was, I would say it was one of the best times in my career because of that.

    You make a good point, I can't remember being taught to ask great questions other than the which, why, where, how and what? Which seem a little rudimentary these days. Great having a conversation with you though! :)

    Lets keep it going!

  • http://scottgould.me/ Scott Gould

    Great stuff Sy – nothing to add, but have retweeted as it's very valuable info you have here!

  • http://www.sytaylor.net sytaylor

    It's my belief that we were not alone in our initial run-in with the “law”.

    You can tell a good company, and a good manager by how they react to a challenge. A glint in the eye followed by a “Ok, so how would that work?”, and you're on to a winner.

  • http://scottgould.me/if-your-blog-is-really-your-home-then/ If Your Blog Is REALLY Your Home, Then: – scottgould.me

    [...] Being a good host is about drawing conversation out of people – for help with this, read Sy Taylor’s view and Robin Dickinsons’s [...]