How To Ask Your Way Into An Engagement
Be inquisitive and be genuine
What do you think about opening a conversation with a question? See what I did there? Oh my, I did it again.
Using a question as an ice breaker for engaging with someone is a well-known technique. This is a recommended approach for both the spoken and the written formats. The question should, of course, be purposeful. Importantly, it should be of interest to the audience.
But do you stop with just one question? Is there something as too many questions?
Ask many questions
I was in an online session with Elliott Bisnow recently and he elaborated on this idea. His suggestion was not just to ask a leading question, but multiple questions throughout the conversation.
He made a further point. These questions should not be basic or routine, but thoughtful and deep questions that get the other person fully engaged.
As an example, you don’t want to ask a runner what got them into running or keeps them in it — something they have probably been asked too many times already. You should get deeper and personal. Maybe a question on their running method or about something that they are trying to achieve. Knowing the person upfront is therefore critical in this regard.
Other Situations
Ok, I hear what you are thinking. This approach may work in an interview that you are conducting or a one on one discussion. How do you do this in other situations?
- Let’s take the case of presenting to an audience. Elliott mentioned that this method can be applied there also. He used the example of TED talks, where some speakers start by asking a question, give the audience some time to think, and then move on. Some may even end the talk with a question.
- What about an interview, where you are the interviewee? This one is doable too if you are clever enough. You have to be careful though, not to make the interviewer uncomfortable or upset.
- What if you are in front of a panel? Here, your questions should be in a format addressed in general to the panel. There is a possibility of asking questions directly to one person, but you would risk alienating others. And have them lose interest in the question, or worse, you. With a common question, it is also possible to have the panel interacting among themselves, which can work in your favor under certain conditions.
- What if you are trying to sell an idea or pitch something to a client? In this situation also, it is a good idea to ask questions that lead to the pitch rather than just talking to them. Remember, an engaged client is more likely to buy.
Build a rapport
The primary idea behind this is simple. You want to ‘build a rapport’ with your audience quickly. Why is that so important? It is because you want time to fly for them. It could become so good, that they want to give you more time in the end than they had planned.
Journalist Cal Fussman who was also in that session spoke about the time he interviewed Mikhail Gorbachev. He had been given only a few minutes for it, but he ended up spending more than 30 minutes with him. Granted it was an interview where he was asking questions anyway, but his point was that he had to start with a good question and continue that to keep his audience engaged.
Ask questions such that it lets your audience speak about their feelings and desires, and that will help you gain their trust, which will result in a longer, deeper, and meaningful engagement.
Be prepared
How do you come up with the right questions? Think of the purpose behind it. You want to get your audience interested and engaging in a good conversation with you. This requires that you research the person or organization and understand what motivates them beforehand. This should be done in both formal and informal situations.
Other than researching the subject, it is a good idea to have additional information that you can use to connect with them. This cannot be achieved by studying their business alone. While that is important, you also need to know about multiple topics that you can use. This is a very good reason for you to read widely, so your questions will be based on sound as well as interesting information.
Do not stick to the run of the mill with your reading. Spread your thought wings wider and start reading authors and topics that others are not reading.
“If you only read the books that everyone else is reading, you can only think what everyone else is thinking.” — Haruki Murakami
As a bonus, you will be in a position to provide new insights back to your audience as well.
Use tact
Asking questions is an art.
Don’t lead with too much information before asking your question. You will end up rambling and likely lose your audience before you even start.
Don’t make the question too curt. Either you will lose your audience or they will have to start asking you questions back to gain context, which defeats your purpose. While counter questions are unavoidable, it is better to have the other person answering your questions mostly and be limited to some questions, if any.
Be thoughtful
There is no good definition for what a thoughtful question is, as it varies by subject and person. This is where research and being prepared comes to play.
David Kadavy suggests a process for having an original thought: – Read widely (not the same sh*t as everyone) – Stop having opinions (stop defending your “beliefs”) – Stop wanting to be liked (start being intellectually honest) – Write regularly (explore what you really think)
You can the same or a similar process to come up with the right questions.
Be genuine
Remember though — it is not a contest of one-upmanship. Don’t make it a series of rapid-fire questions. You do have to be genuinely interested in the person and listen to their answers. This will also help you generate new questions of value. Be a charlatan and your audience will catch on real quick and turn on you.
The idea is to have a free and natural flow of questions, so the other person is truly and happily engaged. The desired result is that it is beneficial to both parties, even as you manage the conversation.
The end
I thought of placing a question at the end, but I did not want it to be artificial. And that’s a good rule to use — don’t force questions in, for the sake of asking one.
Be inquisitive and be genuine, and you should have your audience eating out of the palm of your hands.
