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Interview with Diana Kander: Four Questions That Lead to Better Business Decisions

Business leaders can fall into a trap where they think they always need to be the ones to have all the answers.

However, many successful leaders have a different approach to problem solving. They focus on what are the right questions to ask, rather than what are the right answers to give.

In this week’s Expert Insights, Diana Kander, entrepreneur and author of The Curiosity Muscle, talks about the four questions that can lead to stronger insights and better decision making: 1) what are my blind spots; 2) am I prioritizing; 3) am I measuring the right thing, and 4) how can you involve others to get what you want.



Greg Corombos: Hi, I'm Greg Corombos. Our guest this week on Expert Insights is Diana Kander. She is an entrepreneur and author, most recently of the book, The Curiosity Muscle, a story of how four simple questions uncover powerful insights and exponential growth. She is also the author of the novel All in the Startup, which we’ll be referring to as well. And Diana, thanks so much for being with us.

Diana Kander: I'm excited to be here. Thank you.

Greg Corombos: I should correct myself. It's All in Startup. There's a poker reference there. So it's important that everybody understands the reason for the title there. So let's start with your new book. Asking questions is something that sometimes leaders are reticent to do. Talk about why it's important to ask questions, instead of having more of an instinct of proving that you're right.

Diana Kander: You know, I think most leaders think that they got promoted to their current position because they had all the right answers. So they feel even more pressure to have the right answers. But all of the best leaders that I've worked with are more focused on asking the right questions as opposed to having the right answer. And when you start thinking about better questions to ask, you're going to significantly improve the results that you get.

Greg Corombos: Do you get the sense that leaders are understanding this more as we get into a new era here? Or is it still the instinct, like you just said just a moment ago, that having the right answers is how you got here. So everyone's gonna expect me to have them going forward?

Diana Kander: I think they have a natural pull to have the right answers. But the new economy is changing so quickly, that a lot of people find themselves in positions where they're like, I have no idea how to answer this question. And so they're kind of being thrust into that position. But I think our natural instincts are, I was promoted for a reason. I need to have the right answer to this problem, as opposed to, who can I go to understand insight about this problem? Where do I find my blind spots about this problem? And how can I involve others to help me come up with a much better solution?

Greg Corombos: All right. [We] won’t keep folks waiting any longer here. What's question number one?

Diana Kander: Question number one is, what are my blind spots? So any problem that you're trying to solve, there's all these things that you think you need to solve about it. But then there's this whole other list of things that you aren't even aware of. So a great example is in writing the book, I actually challenged myself to do a 10-minute plank. The book is a business fiction book. And so one of the characters in it, it's trying to do a 10-minute plank. And I thought, it sounds crazy. But I'm going to try to do this crazy thing. And I'm going to use the tools in the book to try to accomplish this crazy goal. And, you know, the first thing I tried to do is just to see how long I can hold a plank. And I thought I would just do my best. I would work really hard to do it. And...took me to three minutes. I plateaued. I couldn't get any further. And the most important question is, what do I not know about holding a plank? Who are these people who are world record holders? Who can hold a 10-hour plank? What is it that they're doing that I don't even know about? And understanding those blind spots, and whatever problem you're trying to solve is going to get you incredible insights into directions, you'd even know we're going to bring up such strong results to your problem.

Greg Corombos: So once you've identified your blind spots, what's your next question?

Diana Kander: The next question is, am I prioritizing? Like, where do I get started? So now I've come up with instead of one possible thing to try it out, now I’ve come up with 10, 20 solutions that I could possibly try. How do I prioritize which ones are going to get me the most value? Am I being selective enough with my time? So one of my favorite innovators, Steve Blank used to say, you know, focus is not about spending time on what you want to work on. It's about saying no to every other thing that might be a distraction. And he was just as proud of the thousands of great ideas that he said no to as the few incredible ideas that [he] said yes to.

Greg Corombos: Before we get to the other questions, in addition to yourself, obviously, who should you be asking the questions to?

Diana Kander: People, no matter what you're trying to solve in your business, or what incredible goal you're trying to get to, somebody has done something like that. Maybe it's in a comparable industry. It's usually somebody outside of your organization. So I would find experts, people who have been there and done it. And then I would try to, you know, learn from everything they learned from. So the guy who can do a 10-hour plank, it took them a lifetime to figure that out. So what can I learn in an hour conversation to help me save like 10 or 20 years of trying and failing things that he tried and learned from? Where can I get those kinds of insights so that I can leapfrog the people who have done it before?

Greg Corombos: We're talking with Diana Kander. The new book is The Curiosity Muscle, a story of how four simple questions uncover powerful insights and exponential growth. She's also the author of All in Startup, which we'll get to in just a moment, as well. But we're just in the middle of questions here. So we've talked about figuring out the blind spots and researching those and figuring out different options to take and then figuring out which ideas to pursue. So where do we go in question three?

Diana Kander: Are you measuring the right thing? So once you pick something, is that the right thing? Is it actually working for you? A lot of times, we go with our gut, we pick something, and then we don't measure anything. We just, you know, stick to our gut and say, does it feel like it's working. And it means that we get stuck doing things that aren't really doing anything to help us for way too long. It means it takes us much too long to figure out that we're wasting time and resources. So find objective things that you can measure in your project to figure out if you're going in the right direction. So for me, whenever I was trying something new with my plank, I gave myself two weeks. And if it didn't, whatever I was trying, if it didn't improve my time by 30 seconds, then no matter how good I felt about it, or how I thought it could work eventually, I would just stop and move on to the next thing. And I think that significantly improved how know, I was able to do an 11-and-a-half minute plank in just four-and-a-half months. And it's because I was so diligent about only spending my time on things that were actually producing results.

In business, we frequently work on things that feel good, because we aren't strong enough to measure the real metrics that would tell us whether we're producing results.

Greg Corombos: So we figured out the right idea to address our blind spot, it's working. We've measured it. We know what's working. What's the final question?

Diana Kander: How can you use others to help you get what you want? Like, how can you include other people? So I mean, this question in two ways. Number one, how can they hold you accountable? A lot of times, again, it's very lonely being a manager, so you feel like it's on your shoulders, because you don't want to fail in front of other people. But research shows that if you share your goals with other people that you respect, you're 65% likely to reach your goals. And if you have a regular check-in meeting or somebody checks on your progress on a regular basis, you're actually 95% likely to reach your goals. And I know that sounds crazy, why wouldn’t everybody do it? Because it's embarrassing to state your goals, and then maybe not meet them. People are afraid of that accountability. So that's an incredibly powerful tool. But also in terms of coming up with really good solutions. A lot of times, managers won't go to their team and say, let's do this together. And they're missing a huge opportunity to have their team feel invested in the solutions and really feel like their voice is heard, and that they're valued at work.

Greg Corombos: Let's move now to your previous book, All in Startup. And a lot of it has to do with how to successfully launch products, which obviously entrepreneurs and small business owners would love to have tips on. So there's obviously things that generally work, things that generally don't work. Based on the research you did for this novel and from your own experience, what are the generally proven successful principles?

Diana Kander: Well, I would say, again, I write business fiction. And the first book is set at the World Series of Poker. And poker is the overarching analogy for launching new products and services. And the main thing to take away is, it's incredibly easy to become emotionally invested in the things what you're doing, in poker and in entrepreneurship, where maybe you're doing it because you feel like you've already sunk too much money in. Or maybe you have a chip on your shoulder because somebody treated poorly, I don't know. But it's easy to become emotional about the things that you're doing. And it is those people who could stay objective and say, okay, well, if I was making the decision from scratch, would I continue doing what I'm doing now, or would I change my behaviors? Those are the people that are going to be successful at the end. And as an overarching principle, I think about entrepreneurship the same way I think about professional poker. You're guaranteed to lose. Like, there's no professional poker player that hasn't lost that hand of poker, that hasn't lost the tournament that they've been in. Your [indecipherable] losses. The people who are professionals are those that can minimize their losses, still have money in the bank at the end of the day to keep playing. And that's what it means to be a professional entrepreneur to me.

Greg Corombos: And so I guess the flip side is knowing what to avoid. And people make mistakes by not minimizing their losses, sticking with a strategy that perhaps it's clearly not working. What did you stress in the novel about how not to pursue product launches?

Diana Kander: Well, again, it's so easy to become in love with your idea, and to stop being so objective about it. And really, doesn't matter how good the idea is or how much logical sense that makes. What matters is whether customers find value in it. So the sooner you can get the idea to customers, and get real feedback from them, not like they hypothetically tell you that they would buy it or that they're interested. But they're putting some kind of currency on the table to demonstrate that it's valuable to them. The faster you can do that, the sooner you'll find out what you need to change and what you need to tweak. And if you go into it, think understanding that the first draft of every business never works. And you'll have to make changes. And just thinking about what kind of changes do I need to make to satisfy my customers and to create value for them. You're going to save yourself a lot of heartache in the process

Greg Corombos: Thank you so much for being so generous with your time with us today. And best of luck with the new book. We look forward to seeing that one to be a best seller as well.

Diana Kander: My pleasure. Thank you so much.

Greg Corombos: You're welcome. Diana Kander is the author of the Curiosity Muscle, a story of how four simple questions uncover powerful insights and exponential growth. She's also the best selling author of All in Startup, I'm Greg Corombos reporting for Expert Insights.



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