Ask the Right Questions: Don’t Make this Subtle But Damaging Mistake

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Asking open questions is a great technique for rapport-building and connection.

An open question is a question that gives the recipient the opportunity to express themselves: for example “what’s your favorite thing about living here?” or “how did you get inspired to work on that project?”

(One reason why so many conversations stall out in a haze of awkwardness is too many closed questions: asking “where are you from?” and “do you like it there?” will produce brief, one-word answers that close a dialogue, not expand it.)

However, one mistake I have seen many people make (including myself) is bad question phrasing.

Bad phrasing can carry subtle put-downs, or a passive-aggressive dig, or just an unnecessarily aggressive tone.

Even though the structure of the open question is good, the phrasing and wording of that question can sour the interaction.

In the worst-case scenario, you just come across as a jerk.

Bad phrasing looks like this:

Brian, a startup founder, is chatting with Liz, a financial advisor, at a networking event. After some conversation, Brian mentions his startup is in an early phase and is not generating revenue.

Furrowing her brow, Liz asks him, in a skeptical tone: “So… when do you think you’ll actually make some money?”

This question, while not necessarily a bad question, injects a small amount of negativity into the conversation.

Even if Liz is trying to be positive and connect with Brian, her skeptical tone of voice and word choice betray a negative attitude about him: her facial expression is doubtful, and she uses a word like “actually” which suggests it’s implausible that he will make it work.

In addition, she is assuming that money is the driving factor for Brian, which (if he is like many startup founders) may not be true. So she is creating a frame that boxes him in without giving him a chance to express his own point of view, which may be very different from hers.

She pushes Brian away and makes him feel less heard and less welcome.

Keep in mind, all of this is unconscious. Liz is probably not trying to come across as negative. She is out at this event trying to meet people and build connections.

But her effect becomes negative because she is neglecting her delivery and phrasing.

To have a more positive and welcoming effect on Brian, while bringing up the topic of money, she could keep a soft facial expression and an upbeat tone and say:

“So I’m curious, have you guys thought about the financial situation going forward?”

Here she would be leaving it open to Brian to fill in the gaps.

He is free to say “yes, it’s a major concern that we’re working on” or “no, right now we’re focused on building out the product”. Either way he feels welcome to express his own point of view.

And Liz then learns valuable information on what is important to him, which tells her whether or not he is a potential client.

These tiny conversational subtleties make a huge difference in how our questions are received.

In either scenario, the two would have a basically courteous conversation, shake hands, and exchange business cards.

But only the second scenario is likely to give Liz a response to her email, or a return phone call.

If you are trying to improve the way you come across to others, to become a leader, to be a more effective manager, or generally more persuasive, it’s very important that you pay attention to this.

Justin Aquino