Podcast

120. Answer Any Executive Question

You give an executive a thorough answer and they still look unsatisfied. One question turns into five, you walk away wondering what you missed, and a week later you hear they were uneasy with where things stand. What gives? In this episode, discover the three underlying needs behind almost every executive question and how to diagnose which one is driving any given question in seconds so you sound more influential and convincing. 

You’ll Discover:

▪️The reason a thorough, well-organized answer erodes an executive’s confidence in you 

▪️ Scripts that show a senior leader they can trust your team without having to step in

▪️ How to sound decisive when you’re put on the spot, even when you don’t have all the data

120. Answer Any Executive Question Transcript

How do you become fully confident and in control of your emotions and experience at work? It’s by mastering your own psychology and that of others. On this show, we decode the science of success, exploring how to get out of your own way and advance your career to new levels without becoming someone you’re not.

I’m Melody Wilding, bestselling author, human behavior professor, and award-winning executive coach. Get ready, and let’s put psychology to work for you.

The number one thing that makes or breaks success at your level, how much trust senior leaders have in you. Not how smart you are, your effort, how technically brilliant your work is. Your success comes down to how much those in power believe in your ideas and your grip on the business. Getting buy-in from above is the linchpin for everything else.

Nearly every listener I talk to, every client who joins us in our Speak Like a Senior Leader program, they know convincing, persuading, mobilizing support and sponsorship up the chain of command is non-negotiable. It is the mechanism by which their team gets funded, their ideas see the light of day. It’s what makes every downstream result you need and want possible.

How you get more autonomy, more satisfying work, how you build your case for a bigger role, or what goes on your resume for the next one. And yet sometimes trying to build that buy-in and trust, it can just feel like running into a brick wall, even when you have been somewhere for years and you have tons of credibility with your direct team.

So what most of our clients end up doing is they prepare an airtight argument. They come armed with the data, the context, the plan, and somehow, despite your best answers, your most thorough explanations, you walk away with senior leaders less confident in you, not more. So today we’re demystifying why this happens, what goes wrong, and what to do instead.

Before we get into it, though, if what I’m describing sounds like something you have been running into, you have got to RSVP for my Overlook No More Summit. It is happening September 14th through 18th. This is for you if you want your communication to finally match the depth of your expertise, if you wanna close what we call the gravitas gap between your track record, how you come across, and how much authority gets assigned to you, the opportunities that come your way as a result.

This is a free five-day summit. It is one hour a day where I will be teaching you the exact system for doing just that. So register, it’s melodywilding.com/summit. Link is also in the show notes. Okay. I want you to imagine you are presenting a project roadmap to your leadership and maybe some peers from other teams.

You have spent weeks getting this together. You feel great about the plan, but then you’re barely halfway through your slides and the head of your business unit chimes in and says, “Hey, uh, can you remind me what’s the status of the legacy system migration?” So you pull up your tracker, you walk her through the dependencies, you cover what’s going on in the current sprint, and she nods, but she keeps digging and says, “And, um, how about that pricing experiment we tried a few months ago?”

Once again, you provide all of the data. Everything seems fine when the meeting ends, but in your next one-on-one with your boss, they mention, “Oh, uh, by the way, Ariana pinged me, took me aside after the road mapping call. She seemed a little uneasy about where the migration and the fee structure are at.” And now you’re frustrated.

You can’t help but wonder, “I gave her all of the information. What went wrong here?” There are countless situations like this where you are put on the spot and questioned by an executive. It might be in a steering committee when the head of finance asks why costs are going up, or your boss’s boss asks for your take on whether a project is going well.

A customer pulls you aside and grills you about a feature. It could be a hallway conversation, a tense Q&A after a presentation, a last-minute Slack message from a C-level who wants a gut check before they hop on another call. No matter what, in all of these situations, they want an answer fast, and your reply can determine whether your team gets the funding you need, something gets the green light, or you’re considered for a promotion the next time calibration rolls around.

Your natural impulse in those moments may be to stick to the facts, cover all of your bases. So you launch into the chronology, what happened, when, who was involved, where you are now, what’s coming next. You walk through all of the numbers, you list the dependencies, you name who the stakeholders are.

You figure that if you cover it all, the executive has everything they could possibly need, and they feel confident knowing you know your stuff. But often, you have probably seen this firsthand, a detailed response backfires. So first of all, it’s harder for the executive to separate out what’s most important from what is just context.

It’s just one big pile. And second, the longer you talk, the more likely you are to lose them. Executives are moving quickly. They are scanning for headlines. They are deciding whether to trust your interpretation of a situation in a few seconds or a minute. And because of that, long answers can accidentally create the opposite impression of what you want.

You think you are being thorough, you’re on top of the details, but if you cannot summarize where things stand in a few sentences or with a clear point of view, they assume you actually don’t have a full grasp on it. So this is when one question turns into five, or they seem to dismiss what you say and they go ask someone else.

Decision-makers do not just want information. They need help making a judgment call. That is why you have to speak to the deeper concern underneath the question because of the level they are operating at. They are not looking at your work in isolation like you are. They are looking across teams, customers, commitments, the politics at play.

They may have heard something from a peer of yours. They may have seen a metric move in the wrong direction that you have no idea about. They’re noticing a pattern across multiple departments. So when you answer, giving them a full download, you may technically be sharing accurate information, but you are not necessarily helping them do the thing they are trying to do, which is assess and diagnose the situation quickly.

They are trying to decide, is this fine as is? Is this fragile? Is this failing? They are trying to decide whether to trust the current plan. Do they redirect resources? Do they escalate the issue? Do they have to step in themselves? That means your answer has to do more than describe what happened. It’s not just a data dump.

It has to interpret what it means. I see so many people completely just let this go over their head, and they pay for it in ways they don’t even realize, and it’s all because they are stuck in their own head, their own perspective. They get in their own way with how they respond, and their response actively reinforces the exact in the weeds, too tactical, hard to follow reputation that they are trying so hard to shake.

So again, you give the full download ’cause you think that’s what being thorough means, that a comprehensive answer is a good answer, or so you think. You wanna prove you know your stuff, so you cover every base. You are worried about being caught off guard by the follow-up, so you’re preempting it by sharing everything up front.

And here’s the thing, no one has ever taught you that once someone reaches an executive level, the way they process information has to change by necessity, and that means you need a completely different way of approaching it, too, your communication with them. The good news here is that nearly every executive question traces back to one of three underlying needs.

Once you can spot which of these needs is driving a question, you can size up almost any request in a couple of seconds, and you can make sure that the way you answer makes you look more influential every time. Okay, the first of those needs is reassurance. Is this under control? Often what sounds like a request for a status update is really a request for confidence.

The executive wants to know they don’t need to worry, that there won’t be any surprises. So the timing, the phrasing of this tells you a lot. If the question seems to come out of nowhere without any specific decision attached to it, if the wording is open-ended, you know, how is everything going with that?

Are we good on the migration? Is there anything I should know about X? It often follows an external trigger. Maybe it’s news about a competitor, maybe it’s an upcoming board meeting, it’s a regulatory change, it’s the start of a new quarter, and they’re taking stock before they have to report out to others.

When reassurance is needed, share the takeaway up front, offer one piece of evidence, and mention you will flag anything further. So here’s what this could sound like: “The numbers are looking good. We’re pacing about ten percent ahead of our target. I’ll send you a debrief if anything shifts before our next sales meeting.”

Or, “There’s no concerns on our end. The team closed two of the highest priority tickets last week. I’ll loop you in, though, if there’s a key decision we need you to make.” The second need that underlies questions is guidance. How should I be thinking about this? With these questions, an executive is trying to orient themselves.

They want to wrap their head around a risk, an opportunity, a development, and they want your take on it. They are asking for a position or a point of view from you. They want you to think it through and tell them what your diagnosis or recommendation is. So sometimes they will invite that outright, right?

In a staff meeting, your VP might go around and ask each person how they would approach some upcoming priority. Your boss may forward you a proposal from another department and say, “Thoughts?” Right? Or a cross-functional partner pauses and says, “Hey, what’s your gut say about this?” But other times, this might not even be framed as a question.

An executive might say, “I’m not sure if we’re approaching this right,” or, “I’m trying to understand if this is the right path.” So when guidance is needed, pull out the most important piece of information, not all of the context, and share what you would do. So, for example, you might say, “I see it this way.

Even though we are behind on two milestones, the team has a realistic plan to recover. I would keep the current timeline we have in place for now, and then we can reassess at the end of the month.” Or you might say, “My sense is that we either need to optimize for speed or cost. We can’t do both here, so I’m leaning towards prioritizing speed because of these reasons.”

The third underlying need is action. What do I need to do? These may sound like information gathering questions, but the executive is really trying to figure out whether they personally need to do something or what you will be doing next. So do they need to loop in legal? Should they slow down something?

Do they need to reset expectations with customers? Sometimes this is obvious, again. A decision-maker says “what do you need from me to get this unblocked?” Or, “How can I help move this forward?” But other times it’s more indirect. They might say, “Okay, what’s the next step here?” Or, “How are we communicating this?”

They want to know, can I trust that you and your team have the next step covered? They want to hear there’s a plan, there’s a person on it. So that’s why your answer should not stop at just giving answers like, “Yeah, we’re discussing it.” They don’t want to become the owner, so they wanna know how you, your team, or someone else is driving it forward because their top priority as an executive is momentum or resolution.

So your job here with these types of questions is to explain what you need and by when. So here’s what this may sound like. “I have one request from you to get this moving. Could you connect with Robert in accounting to get the purchase order pushed through?” Or you might say, “The most helpful thing would be for you to come to the first fifteen minutes of next week’s steering committee meeting because your presence is going to show to other people that they should be taking this seriously.”

So to recap, when an executive puts you on the spot, they are usually asking for one of three things. They may need reassurance. Tell me this is under control. They may need guidance. Tell me how I should be thinking about this. Or they may need action. Tell me what’s happening next and do you need me to do anything?

I’ve seen this pattern over and over and over again, 15 years of coaching on both sides of the table. I’ve been on the side of the C-suite leaders who are asking you these questions, and on the side of coaching you, the high performers, trying to respond to them well, and respond to them in a way that has influence, that advances you, that gets you trusted with more.

And everything we talked about today is also supported by the research, and research specifically, believe it or not, they do research on this, executive cognition and uncertainty. There was a researcher in the late ’80s, her name is Frances Milliken, and their colleagues found that leaders face three different kinds of uncertainty.

State uncertainty, which is what is happening, effect uncertainty, which is how will this affect us, and response uncertainty, which is what we should do about it. So those almost map perfectly onto the needs we talked about today. And this proves that even questions that feel like they’re out of the blue, they aren’t random, which should come as a relief because now that you know these three needs, you don’t have to scramble or be reactive.

You can better anticipate what will come your way and answer with the level of gravitas that you are capable of. So one last note I wanna leave you with on all of this. This is about so much more than answering a single question. It’s about the compounding effect this can have on your reputation, how you’re being positioned in the minds of people who decide your future.

Because trust is not earned all at once. It’s not made in one big presentation. It is earned in dozens of smaller moments where senior leaders think, “Oh, this person has a handle on this,” or, “I really appreciated his perspective and direction.” Every time you match your answer to what they actually need, reassurance, guidance, action, you are depositing into their perception of you.

And when those deposits accumulate, that’s how you start being described as, “Oh, they’re great under pressure. They’re someone who really knows the business. I think they’re ready for the next level.” And most importantly, this is also about how you feel about yourself, too. It’s about being able to walk into any conversation, especially the intimidating ones, with the assuredness, the conviction that no matter what gets thrown your way, you can respond with tact, with poise, not freezing, not beating yourself up endlessly afterwards.

That self-trust is truly priceless because how other people see you then catches up with how you see yourself. Now, if what I have been describing today feels like exactly where you are, knowing your work is strong, but wanting to make sure the way you speak and articulate it matches the caliber of what you are bringing, you need to grab your spot for the free Overlooked No More Five-Day Summit I’m doing very soon.

Do not miss this because we are also opening the doors for my program, Speak Like a Senior Leader, for the final time this year with a pretty mind-blowing stack of bonuses if you are a fast action taker. So head to the link in the show notes. It’s melodywilding.com/summit. I will see you there, and I will catch you in the next episode.

Thanks for tuning in to today’s episode of Psychology at Work. If you enjoyed the show, I’d be so grateful if you could take just a minute to rate and review wherever you are listening, it’s how we reach more professionals just like you. And if you’d like to see even more content on how to feel more self-assured, grounded, and in control of your emotions and reactions at work, follow me on LinkedIn or head to the links in the show notes.

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