Conversations are critical to your business – asking great questions is a great way to lead conversations in the direction of your desired outcomes.
Conversations are a critical element to business. Nothing encourages great conversations better than well formed questions. Great conversations are a required component to virtually every new sale, partnership, and hire. They play such a critical role in business yet we take the basic tenants of fostering great conversations for granted.
My least favorite conversation participant types:
- Person who believes talking the most proves they are in control
- Person who talks so fast that asking a question only occurs via an abrupt interruption
- Person who believes they need to answer everything (even if they didn’t understand the question or have no idea what the answer is)
My favorite conversation participant type:
- The person who sits back and then asks the questions that build, clarify, and take the conversation to another level.
A great question says so much about you:
- Proves you are listening (respect)
- Proves you have the ability to analyze in real time (care)
- Proves you are willing to expose that you don’t know everything (trust)
Is there a conversation in our lives that wouldn’t benefit from more respect, care, and trust?
Most people suck at asking good questions. It’s a lost art. It frustrates me. It kills conversations. It wastes so much time.
Question Types I Hate:
Multiple Choice Questions
A conversation isn’t the SAT; please don’t ask a question and then try to offer options a), b) and c). 99% of the time you don’t know the answer (that’s why you’re asking right?) and more importantly you don’t want to lead the person, you want to hear what they think. Don’t be fooled into thinking giving multiple choices will prove your expertise – it won’t, it will laser focus the audience on finding the flaws to your answers so they can reestablish themselves as the expert! (instant backfire – especially in a sales process).
Vague Questions
People work best talking within their area of expertise; layer some context into the question to make them comfortable. For example, if you’re asking about how they do their job, don’t ask “what do you do everyday” ask “how do you manage your marketing campaigns?” It shows you have context and will generate a higher quality response.
How can you ask better questions?
Listening is the critical ingredient to killer questions. You can give yourself an advantage by spending some time preparing for important conversations. A lot of us prepare by researching facts, looking at spreadsheets, preparing mind numbing PowerPoint slides. Next time take 30 minutes and just sit and think about what questions would lead the conversation where you want it to go and provide the understanding your require to meet your objectives. Don’t underestimate this activity – it takes a hell of a lot more brain power than adding silly animation to your slide deck!





Great topic Jen – and by the way, I know you’ve been busy – glad to see you posting again!
I’m constantly reminding myself to listen FULLY to the answers folks give me when I ask them questions. It’s easy to get caught up in your own mind framing your response to one aspect, and then miss something interesting and important in what they are saying.
Another thing I’ve started doing – after I’ve asked a client WHAT they want to do, I’ll ask them WHY they want to do it. Even if I have a pretty good idea what their motivation is (get more business, increase profit, etc.), listening to them say it in their own words gives me great insight into how they are thinking about what it is I’m selling. I wouldn’t get that if I just worked on what I think I know, even if I’m correct.
Hi Jennifer,
Another entertaining read. Your tone, style is refreshing and straight to the point (ie: Most people suck at asking good questions). Made me chuckle at my desk.
Anyways, I’m a big fan of listening first and asking second. Most people take that as being quiet, not interested or involved in a discussion – but I don’t. Too many times people ask a question that would have been answered later on in the discussion anyways. It’s like, “Ooo I thought of a question, so I’m going to interrupt and ask it right now.” It goes back to your point about respect.
An interesting follow-up for you might be to tackle “Answering too Quickly,” when folks provide answers immediately without fully understanding the question.
Joe