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Revolutionize Your Most Important Meetings with Powerful Questions

Summary

This episode challenges the default approach to important meetings, where we often believe that simply sharing our thoughts will be persuasive. The host argues this method misses a fundamental gap in persuasion and introduces a simple, counterintuitive technique to make meetings more effective.

The core technique is to prepare three powerful, open questions tailored to your audience before your most important meeting. These questions should be designed to get the other person talking about the topic you want to discuss, but in a way that is unexpected and opens up their thinking, rather than using leading or yes/no questions. An example is given: instead of asking a boss “What do I need to do to get a promotion?”, a more powerful question is “If you could fast forward three months and I’ve gotten this promotion, compared to today, what would change?”

The shift is crucial: instead of thinking about yourself and what you want to say, you think about your audience—their information, interests, and perspective. This reorientation changes the entire dynamic of the conversation. The host emphasizes starting the meeting with one of these transparent, honest questions and continuing to ask follow-up questions like “What else?” to draw out more information, rather than reverting to simply sharing your own thoughts after the initial question.

The exercise is practical: take 5-10 minutes before your key meeting to write down three such questions. The goal isn’t to check them off a list, but to cultivate a habit of asking more and better questions, making your critical conversations more influential and productive.

Recommendations

Communities

  • Developer Tea Discord Community — Promoted at the end of the episode. A free community for engineers to share ideas, problems, and help each other solve issues. Listeners are invited to join for updates and discussion.

Tools

  • Square APIs and SDKs — Mentioned as the episode’s sponsor. Square offers free APIs and SDKs for developers to build tools and integrations for millions of sellers using their platform.

Topic Timeline

  • 00:00:00 — Identifying your most important meeting of the day — The host asks listeners to identify the most important meeting or moment of influence in their day. He prompts reflection on the intended outcome and the current plan for that meeting, suggesting the default approach is often to go in and simply share one’s own thoughts.
  • 00:02:53 — Introducing the simple technique of powerful questions — After the sponsor ad, the host introduces a simple, counterintuitive technique to make meetings more persuasive. Instead of leading with your thoughts, the key is to think of and prepare key questions that will get the other person to talk about the desired topic.
  • 00:03:51 — The difference between leading and powerful open questions — The host clarifies that the technique is not about using leading questions, which suggest an answer. Instead, listeners should frame open, powerful questions. These questions are often unexpected, which helps snap people out of normal thinking patterns, making them more effective.
  • 00:04:19 — Example: Asking for a promotion with powerful questions — A concrete example is provided: discussing a promotion with a boss. The default approach (sharing your thoughts) and a bad leading question (“Don’t you think I’m close?”) are contrasted with a powerful open question: “If you could fast forward three months and I’ve gotten this promotion, compared to today, what would change?” This reframes the discussion and invites deeper thought.
  • 00:07:25 — The exercise: Prepare three powerful open questions — The host gives the actionable exercise: For your most important meeting today, take 5-10 minutes to write down three powerful open questions. He advises starting the conversation transparently with one of these questions, without a long lead-up. The questions will differ based on the audience, reflecting a shift from thinking about yourself to thinking about your conversation partner.
  • 00:09:53 — Continuing the conversation with follow-up questions — A critical point is emphasized: preparing three questions is not a checklist. After asking an initial powerful question, you must continue the conversation by asking follow-up questions like “What else?” to draw out more information. The goal is to ask as many truly good questions as possible throughout the meeting, not to revert to simply sharing your own prepared points.

Episode Info

  • Podcast: Developer Tea
  • Author: Jonathan Cutrell
  • Category: Technology Business Careers Society & Culture
  • Published: 2022-09-28T07:00:00Z
  • Duration: 00:12:03

References

Podcast Info

Transcript

[00:00:00] What is your biggest meeting today?

[00:00:16] Think about it.

[00:00:17] Look at your calendar.

[00:00:18] Take a minute.

[00:00:19] What is the most important meeting, most important event that’s occurring in your life today?

[00:00:25] And I’ll give you a little more parameters here.

[00:00:29] What is a moment of influence, a moment of change that you are trying to affect today?

[00:00:39] That moment might be change for yourself.

[00:00:42] It might be change with you and another person, a friend, a family member, a coworker, a report,

[00:00:48] your boss, whatever it is.

[00:00:50] I want you to think about your intended outcome.

[00:00:55] You can do this always with important moments like this.

[00:01:01] But I specifically want you to think about the intended outcome and your current plan

[00:01:08] going into whatever this meeting is.

[00:01:12] If my assumptions about the average person are correct, then it’s very likely that you

[00:01:19] are thinking that you’re going to go into the meeting and share your thoughts.

[00:01:26] This basic way of approaching a meeting where you walk in and you expect that sharing your

[00:01:32] thoughts is going to be persuasive.

[00:01:36] Fundamentally, this is missing a huge gap, a huge gap in what it means to persuade another

[00:01:45] person.

[00:01:47] I want to challenge you today to do something slightly different.

[00:01:51] I’m going to give you a simple technique to make your meeting today more persuasive.

[00:01:56] We’re going to talk about that right after we talk about today’s sponsor, Square.

[00:02:07] Today’s episode is brought to you by Square.

[00:02:09] There are millions of sellers across the globe that are using Square to run every aspect

[00:02:14] of their business right now.

[00:02:16] And they are right now looking for custom solutions that are deeply connected with what

[00:02:22] they are already building and easy to use.

[00:02:26] This is where you as a developer come in.

[00:02:28] You can grow your own business by extending or integrating with Square’s free APIs and

[00:02:33] SDKs to build tools for sellers.

[00:02:36] Learn more by going to developert.com slash Square.

[00:02:40] That’s developert.com slash Square.

[00:02:43] Thanks again to Square for sponsoring today’s episode of Developer Team.

[00:02:53] This technique is so simple and it’s going to be a little bit counterintuitive at first.

[00:03:01] But once you try it, once you see the actual effects, I can almost guarantee that you’re

[00:03:08] going to want to continue doing this in every important meeting that you have.

[00:03:13] Here’s what I want you to do.

[00:03:15] I want you to think of the key questions, the key questions that you can ask to get

[00:03:23] the other person to talk about what you want to talk about.

[00:03:28] Now I want to be clear here because people can quickly see when you’re trying to use

[00:03:33] leading questions.

[00:03:36] Leading questions have obvious answers or they suggest an answer that you want to hear.

[00:03:43] They suggest a course of discussion without giving options to the person to actually share

[00:03:49] what they really think.

[00:03:51] Instead, I want you to frame these as open questions, open questions, and more specifically

[00:03:59] open, powerful questions.

[00:04:02] These tend to be, these powerful open questions tend to be questions that are a little bit

[00:04:07] unexpected on average.

[00:04:10] It’s not always true, but usually it is.

[00:04:14] Let’s say, for example, that you want to talk to your boss about what it will take for you

[00:04:19] to get a promotion.

[00:04:21] Now an example of what you might do by default, you might walk in and say, you know, I’ve

[00:04:27] been thinking a lot about my job and about my future and I think it’s probably time

[00:04:32] that I get a promotion and I’d really like to figure out how to do that.

[00:04:38] Really you’re just telling your boss what’s on your mind.

[00:04:41] Now they may glean from this that they need to provide some kind of information or that

[00:04:47] you’re kind of trying to ask the question of what’s necessary for me to get there, but

[00:04:53] it’s not a very effective way to really get that clear information from your boss.

[00:05:01] Often the ask needs to be clearer than this.

[00:05:04] So we’ll go one step up.

[00:05:06] We’ll ask a question, but it’s not going to be a very powerful or open question.

[00:05:10] The question might be something like, don’t you think I’m getting close to getting a promotion?

[00:05:17] This is a bad question in many ways.

[00:05:19] One, it’s kind of leading when you say, don’t you think you’re kind of suggesting that they

[00:05:24] should answer with a yes.

[00:05:26] This is not a very good question because it makes that person feel boxed in.

[00:05:30] They may have more context they want to provide.

[00:05:33] You’re also asking a yes or no question.

[00:05:35] That means this is not an open question.

[00:05:38] Instead, you may want to focus on a question that sounds a little bit like this.

[00:05:42] If you could fast forward three months and I’ve gotten this promotion, compared to two

[00:05:48] compared to today, what would change?

[00:05:53] This question is kind of putting them into a different thinking mode.

[00:05:58] It’s unexpected because people don’t often think about an alternate future or specific

[00:06:03] future unless you provide them that context.

[00:06:06] You’re asking an open question.

[00:06:09] You know, you’re saying what would be different, right?

[00:06:11] What kinds of questions tend to be open questions?

[00:06:15] So you’re asking an open question.

[00:06:17] You’re giving them some kind of guidance and it’s a little bit unexpected.

[00:06:21] Now, why does it matter that it’s unexpected?

[00:06:24] This is not necessarily a critical factor in asking a powerful question.

[00:06:29] But the reason it’s typical of a powerful question is that it tends to snap people out

[00:06:35] of their normal thinking patterns.

[00:06:37] That if you had to think about what a future, you know, three months from now looks like,

[00:06:43] that’s not a typical thinking pattern.

[00:06:46] If instead you asked a more typical or less powerful question, it still could be open,

[00:06:50] but it’s not as powerful.

[00:06:52] You might ask, you know, what do I need to do to get a promotion, right?

[00:06:55] And you can kind of hear the difference here.

[00:06:57] What do I need to do to get a promotion is a very different kind of position to think

[00:07:03] from for your boss than what looks different in three months once I’ve already gotten the

[00:07:09] promotion.

[00:07:11] At the core, you’re trying to get the same information with both questions, but you’re

[00:07:16] framing things in a different way from one question to the next, and that framing matters.

[00:07:22] So the exercise here is simple.

[00:07:25] For your most important meeting today, take five to ten minutes and write down three

[00:07:32] powerful open questions, three powerful open questions that will get the conversation rolling

[00:07:40] in the direction that you’re hoping it will roll in.

[00:07:43] I’d encourage you, as much as you possibly can control this, try to start the conversation

[00:07:51] with one of those questions.

[00:07:53] Don’t do a ton of lead up.

[00:07:55] Don’t try to couch it in a bunch of kind of, you know, I’m not really sure what to say

[00:08:00] about this, but, and then share your open question.

[00:08:03] Instead, open with something that’s transparent and honest.

[00:08:07] Say, I have a question that I’d like to ask you, and it might be a little bit different

[00:08:12] than the average question you get on a day-to-day basis.

[00:08:16] This kind of prepares the conversation in a way.

[00:08:19] Now, notice that you’re going to have different questions depending on who the audience is,

[00:08:24] and this is a little bit of a shift from the kind of default way that we would approach

[00:08:29] communication.

[00:08:30] If we were just sharing what was on our mind, we might change it slightly depending on who

[00:08:34] we’re talking to, but for the most part, it’s going to look pretty much the same from

[00:08:38] person to person.

[00:08:39] However, critical questions, open questions like this, are very likely going to change

[00:08:44] depending on who the audience is because, and here’s the critical thing I want you to

[00:08:48] understand.

[00:08:49] The reason that they’re going to change is because instead of thinking about yourself

[00:08:54] in this conversation, you’re thinking about your audience.

[00:08:58] This shift will totally change your communication in these critical meetings.

[00:09:03] You’re thinking about your audience, and more importantly, you’re thinking about what

[00:09:08] information do they have?

[00:09:11] What kind of interest do they have in this discussion?

[00:09:17] Otherwise, your questions are going to fall flat, and you know that they’re going to fall

[00:09:22] flat if you ask the wrong question to the wrong person.

[00:09:26] So, orienting your most important meeting today around these three questions, and you

[00:09:32] don’t have to ask them all.

[00:09:34] The conversation may evolve naturally towards one or the other.

[00:09:38] Whatever one feels like it’s a good opening question, you can use that.

[00:09:43] You’re not checking boxes here.

[00:09:45] The goal is to have you start thinking about asking more questions more regularly.

[00:09:53] Here’s the important thing that I don’t want you to miss here.

[00:09:57] Just because you’ve written down these three questions doesn’t mean once you’ve asked a

[00:10:01] question or two questions or three questions that you’re done asking questions and now

[00:10:05] you can start spilling all of your information.

[00:10:08] Once you ask a question like, what does it look like in three months when I have this

[00:10:13] position?

[00:10:14] What has changed?

[00:10:15] They may share some information.

[00:10:17] You may follow that question up with another question like, what else?

[00:10:22] What else has changed?

[00:10:24] They may share some detail and then kind of turn the hose off.

[00:10:28] And you’re asking, give me more information.

[00:10:31] Tell me more of what you’re thinking.

[00:10:33] What else is there?

[00:10:34] Is there more information that you haven’t shared yet or is it something that we can

[00:10:40] go and get more information on?

[00:10:43] The goal here is to try to ask as many good questions, not just fluff questions, but truly

[00:10:50] good questions as you can in your meeting.

[00:10:55] Thanks so much for listening to today’s episode.

[00:10:57] Thank you again to today’s sponsor, Square.

[00:10:59] If you want to start building tools for millions of sellers worldwide, head over to

[00:11:03] developert.com slash square to get started with their free SDKs and APIs.

[00:11:08] Thanks so much for listening to this episode.

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