Do Something Different: A Leadership Podcast

The Critical Leadership Question You Never Think to Ask

Rusty Gaillard Season 1 Episode 32

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There’s one deceptively simple question that most people never stop to ask, but it holds the key to clarity, confidence, and success. Whether you're facing a career crossroads, navigating workplace conflict, or stepping into a new opportunity, this question can shift your entire approach.

This episode breaks down how three professionals—each facing wildly different challenges—found their way forward by starting with this one question. You’ll hear how leaders get trapped by external pressures, and how to strip them away to find the clarity that fuels powerful action.

Key takeaways:

  • Why clarity and confidence are the building blocks of personal power
  • How external noise—like social pressure, past experiences, or fear of judgment—distorts decision-making
  • The question that every leader should ask themselves in moments of uncertainty
  • Why too much information can paralyze decision-making
  • Real examples from leaders navigating career decisions, conflict, and strategic opportunities
  • Why personal power isn’t about control—it’s about alignment and conviction
  • The mindset shift that leads to authentic leadership and long-term growth

This episode is a practical, inspiring guide to reclaiming your power, redefining your path, and making decisions that align with who you truly are.

Episodes referenced

The Hidden Career Killer for High Performers (Episode 29)

More Strategic Decisions in 3 Steps (Episode 19)

Rusty Gaillard is an executive coach, helping mid-level corporate leaders create more career success while working less and enjoying it more. That's real freedom.

Get more leadership tips to grow your skillset and mindset at rustygaillard.com, and follow Rusty on LinkedIn.

[0:05] There is one critical question that most people never ask themselves,

[0:10] but it is the key to your success as a leader in your career and more broadly in your life. I'm Rusty Gaillard and this is Do Something Different. It is a leadership podcast to help you be more successful. I have three clients who are facing very different challenges. One of them, Sarah, is at a turning point or an inflection point in her career and trying to figure out what to do next. David is facing a big opportunity and trying to figure out how to capitalize on that most effectively. And Grace has a conflict at work, an interpersonal conflict, and is having to navigate that. Those three situations may seem very different on the surface, but underlying them is this one question that can be key to help you successfully navigate any situation that you're in and be more successful. Over the last several weeks, the last several episodes of Do Something Different, I've been talking a lot about mindset and the power of clarity and confidence.

[1:12] Clarity is knowing where to go, knowing what success looks like, knowing what your next step is. You have to be clear about how to move forward. And confidence is your ability to execute that successfully. Now, a couple episodes, I talked about confidence and where does confidence come from. And I encourage you to go back and listen to that because it doesn't mean you have to have experience doing that thing in order to feel confident doing it. If you believe that, you're going to be stuck because there's a first time for everything. But you can still have confidence. So go back and listen to the episode from two weeks ago. It's got a lot of great information there about how to develop your own confidence. But let's look at these three examples and tease them apart a little bit so we can understand what is this key question and how can you ask yourself that question so that you can build the clarity and the confidence to move forward. Sarah was the first example, and she is facing a career inflection point. She has just coming out of a difficult phase of her career where she worked for a bad boss and some of that negative reputation and negative energy rubbed off on her, and she had to build her way out of that place. That's where she spent the last year investing in recovering and establishing herself, rebuilding her credibility. She has now done that. And now she's facing this question. What next?

[2:34] She had so much of her energy focused on recovery that now that she's back to even, she's trying to figure out where is my next step? And she is not yet clear on that answer. That's obvious as you hear that story from the outside. How could you possibly move forward when you don't know what forward is? The second example I mentioned is David, who's facing an opportunity at work. David is a technical engineering leader and has great credibility with the business. David was invited by the executive team to step up and identify opportunities across the business for technical projects that can drive significant business growth and efficiency. The challenge is some of those technical projects that David sees opportunity in are in areas of responsibility of his best business partners. So now what do you do? Do you advise the corporate leadership to say, oh, we need to go solve this problem in my co-workers business area? It's a little bit of a tricky spot for David. And he's trying to figure out how do I navigate that situation?

[3:37] And then there's Grace. Grace works at a relatively small company without a lot of firm process. They tend to be reactive as problems come up. And the result of that is that things can go off track. One of Grace's co-workers escalated an issue to the CEO that was an area that Grace was responsible for. Grace was not happy, especially when she figured out that the escalation was wrong. It was a red herring. There was no issue at all, but it got called to the attention of the CEO and Grace had to deal with it. So now what does Grace do? How does she handle the interaction with the CEO? How does she handle interaction with this person who falsely escalated something that turned out not to be an issue?

[4:20] When you look at these situations, we're talking about career. We're talking about responding to opportunity. We're talking about handling conflict how are those things the same well they're the same because in order to handle them you require clarity and confidence but where does that come from and that's where this key question arises and the question is actually quite simple it's this what do you want.

[4:47] It's a simple question, but most people don't ask it. Or if they ask it, they cloud their answer or they limit the sense of possibilities because they start to think instead of what they want, they start to think, what are other people going to think? Or what is possible? Or what have I done in the past that works? Or how do I optimize? How do I make the best decision or optimal decision? Or how do I avoid putting myself in a situation that in the future will become a trouble? All of those things are considerations when we think about what do I want, but we rarely ask the very most basic version of that question, which is stripping away all of those constraints, all of those externalities. Just tune in to what do I want? The simple example I like to use is going into a restaurant. When you go into a restaurant, rarely do you ask to see all of the ingredients of the things on the menu and the nutritional breakdown and all of that because that's not how you make a decision about what you want to eat. When you think about what you want to eat, you tune into, what do I feel like eating? I don't know about you, but if you've been in a restaurant where there's calories listed on the menu, which I have, I find that completely disorienting because I go in saying, oh, you know what, I feel like eating a hamburger. And then I look at the calories on the hamburger. I'm like, whoa, I'm not going to eat that. That's out of that's out of control. That's way too many calories. The extra information actually can make it harder to make a decision.

[6:12] It's the exact same thing in the case of Sarah and David and Grace. There are so many external factors at play in all of those situations. It makes it difficult to make a decision.

[6:26] A few months ago, I also recorded another episode and I talked about decision making and I offered two different pieces of information. The first set of information is about factors that make decisions difficult. I actually described that as seven factors that make you stupid. Go back and listen to that episode on decision making because those seven factors, which are present all the time in the work environment, degrade our ability to make good decisions. Notice those and be able to counteract them with the three positive decision steps that I offered, one of which we're digging into today, which is this notion of simplicity. Make the decision simple. Just ask yourself, what do I want in this situation? And strip away all of the externalities.

[7:14] When you get clear on what you want, now you're in a position of clarity and you can execute that with confidence. And when you combine those, clarity and confidence, what you get as a result is power. And when I talk about power, I don't mean power over other people. It's not like you all of a sudden you can tell people what to do, but you are in power of yourself and you're in power over your own decisions. And that makes a huge impact. In fact, it's one of the critical ingredients to executive presence.

[7:46] So if you want executive presence, it has to start with the question, what do I want? And when you get clear on what you want and what's important to me, then you've got clarity, you execute it with confidence, and the result is power.

[7:59] One of my friends, Mike, gave me an example of what this looks like. His company was, he had just been, he was in a small startup company that had been acquired by a larger company. And after the acquisition, the larger company said, hey, we've got this big corporate initiative. We need you to be a part of it. And we have status updates every Monday morning. And Mike's like, okay, fine. Until he finds that the status updates are at 9 a.m. in New York. We live in California. 9 a.m. in New York is 6 a.m. in California. And Mike said, I don't really agree with this initiative. This is what he told himself. I don't really agree with this initiative. I don't think it's that important. I don't want to be up at 6 a.m. because it interrupts my morning time and my family time. And so I'm not going to do it. He got clear on whether it was important to him, whether he would do it or not. Very simple decision. He wasn't worried about what are they going to think and this other people. He just got very clear and he had the confidence to go out and execute it. And so he told his boss, I'm not going to be there. His boss, of course, didn't like this because his boss wanted him there. He said, look, you need to be there, Mike. This is important for the company. It's something that you really need to be a part of. And Mike said, no, I'm not going to do it. Now that is power.

[9:13] It is powerful because Mike isn't trying to control anyone else. He's not trying to tell anyone else what to do, but he's very clear on what's important to him, what he wants, and he has the confidence to go out and execute it. And when you are clear and confident, you show up with power. And people who are powerful are going to command some degree of respect because they are clear about who they are and what's important to them. I'm not talking about using this in some kind of irresponsible way or again it's not power over other people it's about being very clear with yourself about what it is that you want, this is important question to me and frankly it's a personal question to me because when i was making the decision to leave apple and start my own business as an executive coach this was the question that got me to the clarity of what I wanted and the confidence to move forward and execute that. Before that, really asking that question, I was stuck. And I was stuck because all of these external factors were part of my decision process. I thought I was asking what I wanted. But what I really was asking myself is, what do I think is possible within all of these constraints, including what are other people going to think of me? What is my dad going to think of me? Is this consistent with what I've done in the past?

[10:37] Is there a higher risk of failure? Are people going to think less of me because I make this choice and it does or it doesn't work out? I had so much noise around the decision, I couldn't get to what I wanted. So I had to deliberately strip away the noise. And that was at someone's invitation, helping me see the noise, which is why I'm telling you this today. So let's go back to Sarah and David and Grace. Sarah, who's facing a career decision. There's no right path in your career about what is the best next step. The question is what is right for you. So when I work with someone like Sarah, all of my energy goes into understanding Sarah and what's important to her, helping her tease away some of the noise so she can get to the core question of what she wants.

[11:24] And one of the key premises there is don't make it so hard. You don't have to make a forever decision. You just make a decision today to take a step forward and go in that direction. It's something you can always change. When it comes to David and the opportunity, once again, there is no right answer. David was presented with a business opportunity. On the one hand, he could say, hey, this is an opportunity for promotion and advancement and executive visibility. I'm going to take it. On the other hand, he could have said, well, my primary alliance is to the people I work with, and what's most important to me is relationship, so I'm going to honor those relationships, and I'm going to say no to the executive opportunity. Either one of those is a totally justifiable response. I would also argue there's a lot of room in the middle for finding a third way. It doesn't have to be at one of the extremes.

[12:13] But again, the question here is for David. What does David want? To get clear on what his values are, what's important to him, and explore ways of finding that third way, which allows him to move forward, capture the opportunity, and maintain relationships.

[12:29] And of course, there's Grace, who is dealing with interpersonal conflict. And interpersonal conflict is one of my favorite topics because so many people get all wrapped up in what can I say? What's permissible for me to say in the business environment? What will the other person hear? Or how can I say what I want to say without really ruffling feathers or disrupting the relationship? And that's too much constraint. That's too difficult a question to answer. Start with the most simple question. What do you want to say? And so that's the conversation I had with Grace. What do you want to say? If you took away all the filters and you took away the who cares how she's going to respond or any of that stuff, and you just, what do you want to say? Get to make it very simple and clear. Then afterwards, you can start putting in all of these other considerations to figure out how do you frame this in a way that is constructive?

[13:17] If you've listened to any of my podcasts, you know that my primary principle is to be true to yourself, to know yourself, to do that self-reflection, to do the introspection, know what's important to you, get that clarity and have the confidence to move forward and do something different. Because it's doing something different rather than doing it the same way you've always done it, that's what leads to growth. And growth always is more important than your short-term performance. Your long-term growth outweighs short-term performance every time.

[13:47] The truth here is that you have unlimited capacity to grow and that's why i get so excited about a work that i do because you can grow you can keep growing you can do new things you can learn new skills you can have more impact you can grow your executive presence and it starts by knowing what you want take that time to get clear don't feel like it has to be this big complicated question and you have to solve for 28 different people's interests. Solve for your interests. Get clear on what you want and then be willing to take a step forward to do something different and act on it. And that is the pathway to success.


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