Executive Interview Tips for Senior Leaders and Directors

Some of the most capable professionals I meet keep finishing second when they go for executive and director roles.

Not because they’re not qualified. Not because they don’t interview well. And not because they didn’t 'prepare enough'.

At senior level, interviews aren’t really about competence. They’re a 'real job' conversation. The panel is assessing what it will feel like to have you in the room when things get challenging, messy, political, high-stakes or exposed.

In this episode, I unpack the shift that helps you stop sounding like a brilliant participant and start sounding like the leader who can hold the role.

I talk about the job behind the job, the three things senior interviews usually come down to, how to answer in a way that shows leadership under pressure, and how to handle the dreaded weaknesses question without doing the “I’m a perfectionist” dance.

If you’re going for a senior leadership role, an executive position, or a director appointment, this will help you walk in steadier, clearer, and far more appointable.

If this episode resonated and you want something practical to work with, I’ve created two complimentary Blueprints you can download.

If you’re often the youngest woman in the room, or you’re in male-dominated spaces, and you know you have a habit of over-preparing, over-proving, or second-guessing yourself, you’ll want The Unshakeable Woman Blueprint.

And if you’re an accomplished woman who’s done the career, done the responsible adulting, and you can feel a “what’s next?” chapter calling, you’ll want Success Was The Warm-Up.

They’re both free. They’re both practical. And they’ll help you take this work further in a way that actually changes how you show up.

Transcript

SPEAKER_00 0:52

Welcome to or welcome back to Sky High Coaching Conversations. I'm Janelle Ryan. Let's dive in. Today I want to talk about something I see often in my work. And if you've clicked on this podcast episode because of the title, it's probably going to land for you. So as you listen, I invite you to take notice of what comes up for you. And maybe you might even wish to make some notes. Let's go. Some of the most capable, talented, experienced professionals I meet keep finishing second when they go for higher roles. Second. Not because they're not good enough, not because they don't have the experience, not because they're missing something obvious. They're often wildly qualified, but they keep missing out. And yes, sometimes there are reasons completely outside your control. An internal person has been quietly groomed and they've already, you know, they've already decided that's the person they're appointing. Someone comes into the interview with a very niche piece of experience. A panel has politics going on behind the scenes that you know nothing about. That happens. But when it isn't that, when you're genuinely in the mix and you're still not getting over the line, it's usually not the basics. It's something more subtle. And I want to name it because once you see it, you can't unsee it. At executive and director level, the interview isn't really an interview. It's not a test of competence. It's a real job conversation. It's an appointment conversation. And as I said, the shift is subtle, but it changes everything. Most interview advice is built for us when we're in earlier stages of our career. Research the organization, know your CV, dress well, prepare examples, answer the questions clearly. All true and all useful. But if you're going for senior roles, you already know that stuff. You've hired people, you've sat on panels, you've been in the room, you know how to prepare. So if you've been doing all the right things and you're still finishing second, you're probably not being assessed on what you think you're being assessed on. So let's talk about the trap. A lot of senior candidates still show up as if the goal is to prove they can do the job. So they list experience, they explain what they've done, they demonstrate competence, they answer every question earnestly, thoroughly, responsibly. They give context, they give detail, they give proof, and they walk out thinking, well, you know what? I think that went really well. But the panel isn't actually deciding whether you can do the practicalities of the role. They already know you can from your resume and your background. They've probably done a little bit of research on you. They're deciding whether they trust your judgment inside the pressure, politics, trade-offs, and consequences that come with the role. They're deciding what it will feel like to have you in the room when things are messy. When a stakeholder is annoyed or angry or sharp, when a decision is unpopular, when the numbers are tight, when the culture is fragile, when the board is watching. They're deciding whether you can hold your position inside the real job. That's what an appointment is. And that's why two people can look equally qualified on paper, yet only one feels inevitable in the room. So here's a key idea I invite you to take with you today. The job ad is not the job. The job description is the polite version. It's the story they can say out loud. But the real job is usually an unspoken set of pressures. Something inside the organization needs to change or stabilize or grow or be repaired. Someone needs to be handled or some risk needs to be reduced. So one of the smartest things you can do before you walk into a senior interview is stop preparing for the role as described and start preparing for the role behind the job. Ask yourself, what are they really hiring for underneath the words? What's the real ask here? What does this organization really need from the person they're about to hire? Because if you can name that clearly, you can stop sounding like a candidate and start sounding like the leader who's already begun doing the work. Now, there are a lot of factors in hiring decision, of course there are. But at senior level, it often comes down to three things: judgment, influence, and presence. And let's unpack these really quickly. Judgment is how you think, how you decide, how you prioritize, how you handle uncertainty, how you make trade-offs without pretending there aren't any. Influence is whether you can move people, and not through force, through clarity, through relationship, through timing, through stakeholder maturity, through credibility and presence. Presence is the part most people underestimate. And I'm not talking about charisma as performance. It's the felt sense of steadiness you bring. It's how you hold yourself when you're challenged. It's how you speak when you don't have the perfect answer. It's whether you rush to prove, overexplain, or whether you collapse under pressure. At this level, the panel is listening to your words, but they're also reading your nervous system. Even if they themselves don't even realize they're doing it. Now I want to offer you one of the simplest ways to shift how you show up instantly. Before you launch into my background is, orient the conversation around success. And you can do this warmly, you can do it with curiosity, you don't have to be intense about it. You can say something like, I'd love to check where aligned on what success looks like in this role. 12 months from now, what would make you say we made the right appointment? Now that question does two things. First, it signals you think in outcomes and not tasks. Second, it moves you into the seat of leadership because leaders define success. They don't just respond to questions. And once they answer, now you have a thread. Now you can weave your experience through their reality. You're no longer listing achievements. You're demonstrating relevance to their real job. Now let's talk about something else that's a game changer at this level. You don't need a brag list. You need a value thesis. A value thesis is a clean, grounded articulation of the value you create, the problems you solve, and the patterns you're known for handling. This is where you stop sounding like, wow, here's everything I've done. And start sounding like, here's what changes when I'm in a role. Here's the kind of environments I thrive in. Here's what I stabilize. Here's what I build. Here are the kind of problems I'm strongest at solving. Here's what tends to shift in a team or division when I'm in a role. It's not loud, it's clear. And clarity is very persuasive at senior level. And another thing: senior interviews are not won by listening responsibilities. They're won by stories that demonstrate judgment and consequence. And I don't mean 20 stories. Three, one story where you stabilized something messy, one story where you drove growth or transformation, one story where you navigated people, politics, or stakeholders with maturity. And when you tell those stories, I invite you to think like a leader. What was the context and what were the stakes? What decision did you make and what trade-offs did you hold? What did you do first and why? What changed as a result? And what did you learn that you now bring into every similar situation? That last part matters because it signals wisdom. It tells them you're not just describing the past, you're showing them how you think. And when you answer like that, you stop sounding like someone who's participated, you sound like someone who's led. And while we're here, let's talk about the question most people love to dread: the weakness question. At a senior level, this is an acute question. It's a risk question. So please don't do the old, I'm a perfectionist dance. You'll feel the eye roll from across the table. Instead, name a real edge and show how you manage it. And not with self-criticism, with self-awareness and leadership. So you can say something like, I move quickly when I see patterns. My edge has been ensuring I bring stakeholders with me early, because speed without alignment creates drag later. So I've built a discipline around pausing for clarity and buy-in before we execute. That answer communicates maturity. It tells them you know yourself, you don't hide, and you can lead with responsibility. Now, can we talk about the part nobody likes to admit is true? Sometimes the difference between second place and appointed isn't your resume. It's how you hold the room. And this is where so many brilliant women, especially high performers, slip into what I call good girl mode. They become overly polite, they second guess their certainty, they overexplain, they give too much context, they rush their answers, they try to be likable instead of being clear. And I'll I'll, you know, now I want to be clear. I'm not judging that. This is generational conditioning. It's survival, it's what many women learn to do to stay safe and accepted. But in senior rooms, in these interviews, it can cost you. Because the panel is unconsciously asking one question beneath every question. Can she hold her position? Not aggressively, not defensively, steadily. And this is why I love coaching around soft strength, because soft strength is not niceness. Soft strength is emotional authority. It's the ability to stay connected to your body and regulated in your nervous system so you can hold a clear line without speech, without over talking, without needing to prove anything. And before I go any further, there's something else I want to be really clear about. You don't need to be perfect. You do not need to deliver every line flawlessly. You don't need to become a different personality. You simply need the capacity to stay within yourself when the stakes rise. That's what people feel. Okay. Let me leave you with a few questions that can instantly position you as a peer and not a hopeful candidate. Not because you're trying to impress, because you're doing proper due diligence. So you can ask things like, what's the real job here that no one's saying out loud? What needs protecting as we drive change? Where have previous leaders struggled in this role? What are the key stakeholder relationships that will make or break success here? What does good look like in the first 90 days? And what would be unhelpful to do too quickly? When you ask questions like that, my beautiful friend, you're showing them how you think. And senior roles are appointed on thinking. So if you keep being the nearest candidate and not the appointment, I invite you to consider something gently. It might not be that you need more experience. It might not be that you need more qualifications. It might be that you're presenting as competent when what they're craving is leadership. And leadership isn't louder, it's clearer, it's steadier. It's a calm ability to name what matters, hold the line, and lead the conversation into the real job. Now, if this episode hit home and you want something practical to work with, I've created two complementary blueprints you can download right here, right now. If you're often the youngest woman in the room or you're in a male-dominated space, if you know you have a habit of over-preparing, over-proving, or second guessing yourself, you're not alone. Just rest assured, you'll want the unshakable woman blueprint. If you're an accomplished woman who's done the career, done the responsible adulting, and you can feel a what's next chapter calling, you'll want success was the warm-up. Or download both. You're more than welcome to. They're both free, they're both practical, and they'll help you take this work further in a way that actually changes how you show up. The links are waiting for you in the show notes. Thank you for being here. I um invite you to write down anything that came up for you, any insights, light bulb, or aha moments. Until next time, keep expanding, creating, and leading, and I'll catch you again on the airwaves. Have a beautiful day. Bye.