Shut Up and Listen! 

The art of asking good questions. 

Over the years, people who were getting into podcasting would ask me for tips, knowing I’d been at it for a while. Regardless of the person’s experience, or skills as a communicator, my advice was always the same:  be yourself and listen. For better or worse, I never had a problem with the “be yourself” part – listening, however, is a skill I had to work on.  

I would listen to our produced podcasts and hear all the missed opportunities because I was busy formulating my next question or assembling in my head a witty retort or amusing anecdote. Even worse, I’d do any or all of the above and mindlessly ask a question the interviewee had just answered! I didn’t have any tricks up my sleeve to get better at listening, I just…listened. I also got better at listening and holding the thoughts in my head at the same time.   

On our homepage, we talk about “getting to exactly.” It’s essentially a process of getting the other person to the “aha moment” by asking probing questions based on careful listening. The trick is to ask questions in the flow of the conversation. Think of it as a form of conversational jujitsu in that you give in the direction the other person’s leaning; each question teases out their pain points, which shows how deeply you understand their pain and, by extension, them – you’ve been there, you’ve seen it, you’ve experienced it. When the person you’re engaged with finally exclaims, “Exactly!” it’s the aha moment that brings the conversation and the relationship to another level…it’s also a signal that they’re prepared to listen to you, which is just the opening you’ve been looking for.       

Humility and fearlessness don’t always go together, but they are indispensable ingredients in asking good questions – humility is required to willfully defer to the person you are listening to – she is the expert – and fearlessness in not worrying whether your next question will be perceived as “dumb.”  I learned the latter from a business partner who was almost invariably the smartest person in any room he walked into. His questioning was respectful but relentless, and he’d occasionally ask something that would be considered uncomprehending or ill-informed if it came from anyone else. But he had the well-earned confidence to care only about knowing what he needed to know and being certain the topic was completely within his firm grasp. Often, we pretend to understand but are afraid to betray our lack of understanding and wind up with a critical gap in our knowledge. 

Another thing that gets in the way of being an attentive listener is our tendency to talk way too much, particularly in the initial “feeling out” stages. There’s a natural urge to show what we know.  This may seem counterintuitive, but letting the other person talk, and keeping him/her talking by asking pertinent questions, shifts the power dynamic in your favor. I remember an interview with Michael Caine in which he said the reason he spoke so fast – and so much! – was because of the deep-seated insecurity stemming from his lower-class background. In England’s intensely class-conscious society (which was more acute at the time), people from the upper classes were more laconic because they could be – they expected people to lean in when they spoke. You may have many intelligent things to say, but often the less you say, the more you’re heard. Plus, sympathetic listening tends to get the other person to say more –  if you’ve ever seen a Harold Pinter play, you know how powerful it is to let the other person talk and talk…and talk.

But why listen to me when you can listen to Richard Feynman. As a youngster growing up on Long Island, Feynman was continually peppered by his dad with “why questions”: why does the sky appear blue during the day, why is ice slippery? He attributes his lifelong curiosity to these questions, an approach he applied to all the problems he tackled over his celebrated career as one of the most brilliant physicists who ever lived. Do a search online and you’ll find several fascinating interviews and lectures he gave on the subject of why questions – which actually suggests a modification to the title I’ve given this post: shut up, ask questions, and listen!  

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  1. Larry Cummings

    Charles is a masterful listener.

    Active listening, humility, and fearlessness are essential to asking good questions and having meaningful conversations. Leads2Results’ “getting to exactly” concept and the idea that speaking less often makes one heard more offer valuable guidelines for effective communication.

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