How the Right Question Transforms Your Business

In this episode, we dive into one of the most transformative topics for business growth: asking the RIGHT question.

Ever felt stuck in your business, working hard but not seeing the results? I’ve been there, and I’ve learned that sometimes it’s not about doing more—it’s about asking the right question.

I share how I went from asking safe, ego-boosting questions to asking ones that could radically change my business. Plus, I’ll walk you through the step-by-step framework I use to uncover the one big question that leads to massive results.

Ready to learn how the right question can transform your business? Let’s dive in!

Click play to hear all of this and:

[00:00] Learn why the key to unlocking growth in your business is not doing more, but asking the right question that drives real change.

[02:00] From asking safe, ego-boosting questions to discovering the ones that truly move the needle, discover how this shift can supercharge your growth.

[03:41] Explore an example from 2023 about a safe question asked in a mastermind event—and why it didn’t have the impact expected.

[05:30] Discover the valuable advice from a former CEO on hiring and paying top talent for better results and higher productivity.

[08:30] How raising the pay for a part-time executive assistant led to massive reductions in administrative responsibilities and improved business efficiency.

[10:00] Get a step-by-step framework on how to uncover the one big question that will solve your business challenges and lead to transformation.

[12:00] Learn how asking deeper questions can help you get unstuck and start solving business problems more effectively.

[14:30] A deep dive into why some problems require courage to face—and why accepting the challenge will lead to a greater business outcome.

Listen to Related Episodes:

• What $100M CEOs Taught Me About Growth
• Building Boring Businesses, Embracing Questions, and Doing Hard Things with Codie Sanchez
• How to Ask Questions that Get Results

📧 Join my Newsletter for a weekly cocktail of insider business strategy, personal reflections, and the journey of being a thought leader: https://jasminestar.com/newsletter 📧

For full show notes, visit jasminestar.com/podcast/episode625

Transcript

Jasmine Star 00:00:00  That is the power of asking the right question. A question that I felt left me like open and vulnerable, and it showed how many cracks there were in my foundation. I didn't want to say it out loud. And then I did, because if I wasn't real and honest about the largest gaps in my understanding about what truly moved the needle, everything else was just a waste of time. At the time of this recording, I'm preparing to attend a mastermind for eight figure entrepreneurs. It's not the first time I've attended an event for business owners doing over 10 million in revenue per year, but it is the first time that I'm attending with this group, and whenever something is new, I get nervous. I am a huge introvert, so getting in new rooms with new people, it definitely kind of drives my anxiety. But if my goal is to continue to grow, the cost is getting uncomfortable. If I am not uncomfortable, I am not growing. And I've always maintained I don't want to be the dumbest person in every room, and there's a good chance I will be that person in this group.

Jasmine Star 00:00:56  So my goal is to record a vlog style video to bring you in the room with me. So I've packed my mic and I can't wait to share it on a future podcast episode. I've spent a few weeks thinking about number one, what do I want to get from this event? And then number two, who do I want to connect with this event? And then number three, what is the one most important question I want to ask and get answered? Yes, I always have a lot of questions, but I don't need a bunch of notes or small answers or a list of things to try. What I need is an answer to one big question with one big answer. No. Big answers are usually the single thing that has a huge perspective shift in my outlook, performance, and my business results. So in a future episode, I am going to chat more about what I wanted from the event and who I wanted to connect with. And my one big question. But right now I want to discuss how to know the right questions to ask.

Jasmine Star 00:01:54  So let me back up. Okay, so I used to ask questions that were safe, that kept me from being seen, that kept people from seeing my weak points. And that was great for my ego. But it really hurt my personal growth. Okay, so I'm going to share an example. This is how it played out for me until I decided to change it. So let's go back in 2023, I attended an event in Beverly Hills for seven and eight figure entrepreneurs. Cody Sanchez was one of the keynote speakers. I love Cody, I think she's brilliant. She spoke about how she organizes her content and the team that she's built for each one of her social channels, as those social channels are the main marketing forces in her business. There was about 60 people in the room, so all of us weren't able to ask a question, but we were told, hey, come with a question. Ready? You don't know if you're going to ask your question. And here was this incredible opportunity.

Jasmine Star 00:02:42  I was in a very coveted room. I was sitting with somebody who's literally breaking the frame of informational marketing content. I had spent so much time and money to be in that room. And my question, my one opportunity to ask something that could really move the needle in my business. What was that question? My question was about how she planned and built her content schedule in notion. Okay, for those of you who don't know, notion is a platform for organizing, building databases and a lot more. Okay, that question might not sound like a bad question, but allow me to explain that. Number one, I already used a notion. Number two, my team had created a working system. And number three, after her presentation, I realized that our systems were similar. Okay. Of course, hers was a lot more robust since she was creating about five times the amount of content that I was at the time. The truth is, if I'm looking across from you and I'm talking to you, my question was not the one question that would have radically changed my business.

Jasmine Star 00:03:41  My question? Well, it kept me safe. It was like a flex to keep me unseen. I didn't get a chance to ask that question in the room, but what I now realized was that if I had, it might have improved my business by like, I don't know, 2 or 3%. I needed to learn ways to ask one question that would change my business by 90%, or at least attempt to. Okay, so that was back in 2023. Let's flash forward to 2024. I attended a two day workshop for seven and eight figure founders in Austin, Texas, and it was hosted by nobody else. Then. Wait for it. Cody Sanchez. Now I'm going to be sure to link to a vlog that I created. I made this video about the behind the scenes of the experience and what I learned, so I'll be sure to link to that. But this time around, I went in with two questions that I believed could make a 90% change in my business, and they were both related to expanding my team.

Jasmine Star 00:04:35  We're going to pause here. 2023 I asked a question that kept me safe that would maybe have a less than 5% change on the overall outcome of my business 2024 when speaking to the same person and getting into a similar room, I asked two questions that potentially could have a 90% change in my business. I want to create two distinctions between what was going on here and what I was learning. So when I walked into the room, I was really focused into Cody's two day workshop was question number one. How do I find, test and empower a content strategist? Question number two, how do I train an executive assistant to be what I need? So let's start with that second question training an EA. Okay. So at this point in my life, I was being pulled in so many different directions and I needed help organizing it all. I had hired three other people in the past. I had used a recruiter, I hired a chief of staff, and then nothing worked. I knew that it was me.

Jasmine Star 00:05:31  I had to be the issue, but I didn't know what to fix. The only commonality at every single one of these situations that didn't work in the past was me. And the fact of the matter is, I didn't know how to train them better. Cody has quite a few assistants, so I knew that if she helped me with the answer with this one question. Things would improve in my business in massive ways. I'd get more done in less time because someone was thinking one step ahead of me. I actually asked Cody this question during a break. I didn't want to ask in front of other people, but I got an answer from one of her guest speakers who was also in the room, and then he overheard her conversation. So Ayman al Abdullah, please forgive me. Ayman, I probably butchered your last name. My apologies. With deep respect, Ayman was there and he was a guest speaker at Cody's event. Now he's the former CEO of App Sumo. And when he went in, he took the business from 3 million to 84 million.

Jasmine Star 00:06:20  And so Ayman was there. And then he leaned over and he looked me in the eyes and he said, you're not paying them enough. And I looked at him. I was like, do you even know what I'm paying an executive assistant? He said, here, I don't know what you're paying them, but I can tell you, I know it's not enough. Ooh. So when I asked what he recommended paying an EA, I scoffed because he was right. It was much higher than I was willing to pay, and I was like, oh my gosh, if that's what I have to pay to get a really great EA, oh, I'm going to be out of luck. So then I felt stuck. I couldn't pay what it would cost to get a world class EA. So then what was I going to do? And then he said something that blew my mind. And so I want to make sure that I'm sharing it here. The best people work one fourth of the time, so pay them three fourths more.

Jasmine Star 00:07:09  Okay. So in other words, the best people get task done in only 25% of the time. In other other words, what it takes the average EA to do in one hour. It takes a world class EA to do it in 25 minutes. He said I can still stay within my budget, even paying them more because they would be handling things in less time. So boom, right there and there. I change the role from a full time EA to a part time EA, and then I raise the pay rate and he introduced me to a recommendation there at the event. He was like, hey, I want to make a recommendation, I want to do an introduction. And boom, I have been working with my EA for over two years now. She's incredible. She organizes my life. She plans my days, she plans my travel, she handles my speaking events, she schedules my appointments, and I'm talking about everything from getting drivers to manicures to dentists to a fitness trainer. Literally, I feel like I got my life back and she's not even working 20 hours a week.

Jasmine Star 00:08:06  She's a beast. And guess what? Hiring her has changed my admin responsibilities by 90%. And that is the power of asking the right question. A question that like I felt, well, it left me open and vulnerable, and it showed how many cracks there were in my foundation. I didn't want to say it out loud. And then I did, because if I wasn't real and honest about the largest gaps in my understanding about what truly moved the needle, everything else was just a waste of time. So how can we determine the one question to ask? Let's use a real life example as I head into this eight figure mastermind in Vermont later this week, I am going to be thinking what question to ask. And I learned a framework from Alex Hermosa, and then I made a few tweaks to it, so it made more sense for me. So it aligned with my life and my business. I'm going to share it with you, but I definitely want to give him credit for getting the starting block of my thinking path and how I got here.

Jasmine Star 00:09:01  Okay, so here we go. I'm going to dive into what I've come up with when I'm feeling stuck. I always tried to identify the exact spot where it begins. So what is the center point like? What is the nucleus? What is that main point? Where am I feeling stuck? If I find that, then the right question reveals itself. So right now ask yourself where am I feeling stuck? So once I identify where I'm stuck, I ask myself five questions to determine why. Like why am stuck when I know where I'm stuck and I know why I'm stuck? I can then frame my question clearly, concisely, and directly on what I should do. Okay, so let's break this down with an example, let's say I am trying to figure out my one big question before I go to this mastermind in Vermont. And let's say I really want to fix my conversion rate to book a call. Okay? And let's say I want to focus on my conversion rate from direct message to getting people on a call.

Jasmine Star 00:09:58  Great. I have a focus. Conversions. I have a sticking point. Direct messages. Question one if I did more, would it help? Okay, so in this case doing more wouldn't help me. So like sending more direct messages might not help me because doing more wouldn't fix the conversion rate. And what I'm focusing on is the conversion rate. Question number two I ask myself to find the main question to get the 90% change of an answer. Question two if I had more data, would this help me? Well, in this case, in this particular example, I have a lot of data. Tons of data. I love data, I collect data the way other people collect pennies or stamps. I love it, I'm obsessed. So conversations per day. How many responses on average to conversations, timed response to conversations, conversation rates. I'm telling you, I have all the data I need. Getting more data wouldn't help me find the main question I need to get answered. So then I move on to question number three.

Jasmine Star 00:10:59  Do I actually want to solve this problem in the business? And this is where questions get a little bit deeper. We're going to get be real real. This is where I need to get a real deep understanding. If this is the type of business I actually want to build. Like let's just get real, because sometimes many of us feel stuck, not because of where we are, but because we're tired of building a business we don't want anymore. And like I admit, like, does that hurt to hear? Yeah, I know I asked myself that question a lot of times, and sometimes the answer was painfully clear. I didn't believe in the business model, and if I didn't believe I wasn't stuck, I was over it. And let me just save you a lot of time and pain and energy. If you're over it. You're going to have a hard time getting through it. In this example, building the business model I believe in. Yeah, I'm doing that right now. So yeah, I very much want to solve this problem.

Jasmine Star 00:11:52  But in order for me to solve this problem, I need to take a moment and say something that I think has been misconstrued over the years. Just because I'm willing and wanting to solve this problem, it doesn't mean it's going to be easy. In fact, many people this is this exact problem that I am trying to solve in my business right now. Many people have tried it and they failed. I must believe that if I solve it, I will get disproportionately high returns because so few people have. But when I say that, I must also accept it's like drinking gasoline for breakfast. It's like walking on hot coals. It's like dragging an anvil in a race. Like people quit building businesses because it's crazy and it's hard and the failure rate is absurdly high. So, Yeah. If we want to build a business, we must accept that it will be one of the hardest things we ever do in our life. Question number four. Do I have money to solve this? No. I'm going to be very clear, and I'm going to tell you straight out, I grew up poor.

Jasmine Star 00:12:50  I have more money issues than Vogue. I think money is the root of every solution. Now, I know, like physically, mentally, spiritually. I know that's not true, but my childhood hard coding is a default belief that money can fix it. And after a lot of work, a lot of studying, some therapy, I can now suss out what types of things can be solved with money. So for this example, is the cost of leads to high? Are we paying the sales team too much that it's eating into the profit? Are the sales team not performing well enough to justify the cost of the leads? Okay, I could clump all of these together and say, oh, we just don't have enough money to solve this. But if I really honed in on which precise One that that was like a specific factor to money. I could ask if we could afford to address just that one thing, which acts like a catalyst for everything else. So it's becoming very clear on understanding what would the money solve? Do we have the money to solve that one problem? Question five do we have enough people to solve this problem? So there was a time back, like a 2017 and 2018 when we were building social curator and we created caption templates for social media.

Jasmine Star 00:14:03  So they were like, ad libs fill in the blank style captions that business owners could use easily, and they're gonna post on social media. And we got feedback that people wanted industry specific captions. And okay, so back then, at the time, there were four major industries represented within our app. If we created industry specific templates for those four and also more like general templates, it would require four times the amount of work, right? So four industries times the normal stuff that we're already doing. And we just didn't have that many people on the team to handle that load. It didn't financially make sense to make that happen. Now, this was before technology could customize content with a press of a button, like with AI. But the example like what I'm talking about right now, it just serves to show that sometimes you simply don't have enough people on the team to take on the growth that's needed to get unstuck. Okay, so now let's bring this back to my current example as I'm figuring out what question is going to be the best question to ask in this eight figure entrepreneur mastermind.

Jasmine Star 00:14:59  So in this current example, remember it's like I'm going to get my conversions increased by way of DM. In this current example, I have enough people on the team to handle the work that's needed. Great. I used two examples to show the polarity, sometimes I didn't. I currently have it now. Okay, so let's review the five questions I ask myself to find the one big question that I need to get unstuck. And then to be really clear here, I want to ask this one big question so that I get one big answer to help create a 90% change in my business. So questions are one. If I did more, would it help? Two if I had more data, would it help? Three. Do I actually want to solve this problem? Four do I have the money to solve this in five? Do I have enough people to solve this? So in a future episode, I'm going to share my biggest question that I ask in this future mastermind, as well as what I learned and some behind the scenes.

Jasmine Star 00:15:56  Okay, so like always, I will be taking JD, my husband. I'll be taking my daughter Luna. So there may be like also secrets about how we've built like the most epic snowmen of all time. I mean, y'all, this is the first time we've ever gone to Vermont. And I think, is it Vermont is for lovers? Or is it Virginia for lovers? It's whatever. Some American state that begins with, like the letter V. We've never been to Vermont. We also have never been in this amount of snow. It's going to be very snowy. So we're very excited. And you want to know what I learned? I just feel like this was Mom hack 101. I read that you can rent the ski gear like a bib, like warm clothes for your kids, and you can have it delivered to the hotel. I'm a Southern California girl. Do you think I ever knew this stuff existed? I don't even own warm clothes, so the fact that I am having an outfit shipped to the hotel for my daughter so she can play in the snow.

Jasmine Star 00:16:43  I mean, epic snowman's coming through. Be prepared. I will be posting all behind the scenes in real time on Instagram, and then be taking a lot of that content and building out a bigger story and narrative for my vlog on YouTube. But before I end this episode, I mentioned that I took two questions with me to Cody Sanchez's event. Question one how do I find, test and empower a content strategist? And question number two how do I train and hire an executive assistant to be what I need? It's been a year and a half since that event, and I am still looking for a content strategist. And to be totally honest, I believe I struggled because I wondered if I wanted to build my content channels. So this is me being very real. It is very difficult to create content, especially in like an expansive way, and do it more and more frequently. At the time of this recording, I was just telling the team I was like, I took a sleeping pill last night and my head is not really in the game, and yet we show up.

Jasmine Star 00:17:42  It's been a rough two years on a personal level, like just legit. It's hard creating content when there's a lot of pain and confusion behind closed doors. I am not going to get into the details, but I will say that my brother is an addict and he struggles deeply with his mental health. My parents have paid for his rehab and I have paid for his rehab and therapy and recovery programs. But this past year has a lot has happened and it has taken a toll on me, and it has taken a toll on my parents. And as they get older, I've stepped in to help with their financial planning and life plans. But watching them in so much pain as their son goes through this process has caused deep pain for me to. So I'm not going to get into the other factors at play, but it's been a very heavy couple years for my family and for me personally. I have known for all of 2025 that my content needed a new strategy, but before I did that, I needed to know whether I had it in me to push again.

Jasmine Star 00:18:40  So maybe you've seen I've been consistent. I've kept things going. Even when friends and families and coworkers said, hey, you should take a break. But I knew that if I stopped then, then I would stop for good. I knew that about it. I would not get back on. I prefer and I wanted to make a clear headed decision about when and how I'm feeling. Like when I'm feeling low, that's not the best time to make a decision. So as I began 2026, I spent time alone thinking about what I wanted to do versus what I needed to do in the business. I went through those five questions, and many of them I couldn't answer when it came to hiring a content strategist at the time. But this year. Okay. I started the year silently asking myself real questions. Say, do you count the cost? I began digging deep for content ideas that looked and felt real to my journey that were happening in real time. I asked myself, how could I build a content system for where I was going? Not where I've been or not even where I am.

Jasmine Star 00:19:42  When I look back, I wasn't ready to hire a content strategist because really, I didn't know what I wanted in 2026. That's changing and it makes me so hopeful and excited. I want to say thank you for holding space for me on this crazy ride. Thank you for watching this video and listening to this podcast up until this point. Thank you for being here. Thank you for allowing me to document the journey and be very open about. Things are changing. I don't know exactly how, but I am excited and I'm all in to bringing you in on the journey as we expand. So thank you for watching and listening to The Jasmine Starship.