Think on your feet like an executive
Which means master the art of executive updates
👋 Hi, it's Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.
When I work with rising executives, I expect them to be able to think on their feet. But what does that really mean?
It's not about coming up with a brilliant, original strategy or solution in 60 seconds. It's about mastering what I call “executive updates” – the ability to take complexity and reduce it to a cogent takeaway in real time.
This is a high-leverage skill that will make you seem more senior than you are … and other execs expect it. Here’s my advice for how to do it.
Greg
What “thinking on your feet” looks like in practice
Thinking on your feet happens any time you’re asked a question you haven’t prepared an answer to. That could be anything from, “How’s the new hire doing?” to “Which product feature should we prioritize next?”
If an executive asks you a question like this, take it seriously – even if it seems casual. They’re looking for you to prove that you can do four things:
Keep track of the conversation (aka, what’s already been said, and what are you actually being asked?)
Process lots of data or inputs fast
Reduce that complexity to a suggestion, opinion, recommendation, or outcome
State it crisply and time-efficiently
There are lots of situations where you’ll need to do this, but here are a few that come up a lot (and the good/bad way to respond).
Scenario 1: The battlefield brief (“I heard there was a client problem – what’s the situation?”)
When there's a crisis, I want to know right away: the scope of the problem, how many employees or customers are impacted, in what way, and what timeframe we're dealing with.
Good: Get the update out immediately – not the complete story, just the key points about what happened and the options. “We sent inaccurate enrollment data to a medium-sized client, Sherwood Industries, which they cascaded to their board. They’re generally happy with the account but upset with our sloppiness in this instance, and we’ve committed to speaking on the phone at 4:30 with a mitigation plan and sending accurate data by end of day.”
Get it out, then be okay with an awkward pause at the end. Stop talking and let the other executive think.
Bad: A long intro story about how it happened and what went wrong (“So we put an AE in charge of pulling enrollment data for Sherwood Industries, and the system wasn’t pulling reports accurately…”)
I don't care about the details at that moment – I might care later during the retro, but right now I want to understand with enough (but not too much) information. And don't bury the ask – end with it clearly. Your job is to take that crisis in all its complexity and net it out to "here's the plan” or “here’s what we now need.”
Scenario 2: The napkin math request (“How many users would we need to make this worth it?”)
Napkin math makes people panic, because most people aren’t great at math, and they think they’re being given a test. And they are, in a way – but the test is whether they can be directionally accurate, in a way that sets up a strategic conversation.
Napkin math isn’t a math skill – it’s a decision-making skill. The key is to state your assumptions upfront, and frame the math around the answer you’re trying to solve (not the numbers themselves). Use the "50% rule" – even if we're 50% off with our numbers, what does this tell us?
Good: Start with what you know, then expose the assumptions you’re making. “We’re talking about investing $50,000 to build this, and I assume about 5% of users will result in enterprise contracts, which are currently around $10K ACV – so we need at LEAST 100 users, but realistically more like 300, to make this worth our investment.”
As you can see, this is mostly directional. 5% conversion might be high or low – but exposing your assumptions will help you course-correct if that number is off.
Bad: Getting too caught in the numbers themselves (“I’m not exactly sure what our enterprise conversion rate is, let me check real quick…”). Or – what most people do – floundering and then asking for a day to “work on it”. You need to do one of two things: attempt directionally accurate napkin math, or ask for time (hours not days) to pull some data and come back with an answer.
Scenario 3: The random “what should we do?”
You're being asked for your opinion on the fly – what product to promote, what customer to invite, who to hire. Don't panic and think you HAVE to make the perfect call. Again, it’s about exposing some of your thinking and buying yourself a few seconds to make the recommendation.
Good: Confirm the established options and the outcomes they’re pointing to. “To clarify, we’re deciding whether to prioritize X feature to drive widespread usage or Y feature to satisfy our highest-dollar client?”
Then make a call based on the outcome, not the strategy. “Based on that, I’d prioritize Y feature because we need the client to renew to hit our Q4 target and their renewal date is coming up soon.”
Bad: Say you don’t have an opinion (you should), or hem and haw between the options. Nothing drives me crazier than an executive saying, “This isn’t really my call, so you guys should do whatever you want.” You shouldn’t be on a leadership team if you can’t quickly form a smart opinion.
Scenario 4: The elevator pitch (“So what do you guys do?”)
For your company, product, or team, you need to be able to deliver a crisp elevator pitch – even harder on Zoom than in an actual elevator. The pitch should be anchored in the transformation your product or service provides, and for whom. And you should be able to tailor it based on your audiences – friends and in-laws, investors, prospects etc
Good: You sound like you understand both the problem and the opportunity to solve it. You have multiple ways to discuss the problem and solution, not just one script. When you can describe the problem and solution clearly, you can then adapt it to different audiences. You are optimizing for memorability, not completeness.
Bad: Memorizing a script that sounds robotic. Junior people usually think they need to “nail” a memorized version of the elevator pitch, then get flustered when they realize it's the only version they know.
The mistakes people make in “thinking on their feet”
There are two mistakes people make when they get a question they weren’t expecting:
1. They tell the whole story. Instead of reducing their thinking to the most important facts, they start at the beginning and give a bunch of details no one needs (“So, we rolled out this product back in 2019 … ”). As a CEO, I quickly get annoyed when someone does this and will usually cut them off or start peppering them with questions.
2. They inject their personal opinion too early. Instead of presenting the facts, they start with their opinion (“Well, Joey has been frustrating me with his poor project updates…”). This makes me distrust their judgment and makes me think they can’t step back from their own personal opinion to observe the facts neutrally.
My advice
“Thinking on your feet” is all about quickly building scaffolding around a conversation: the inputs, the data so far, the options and potential outcomes, and your recommendation.
You don’t have to be right every single time you are put on the spot– you just have to be able to build the scaffolding quickly and get to a point of view.
If you need a little time to think, that’s okay (but 30 seconds, not 10 minutes). Take a beat. Then say less than you think you should. I much prefer executives who are "slower" to respond but then are crisp.
And once you finish your update, pause. The silence can be awkward, but it shows you have delivered your opinion and gives your audience time to respond – hopefully as succinctly as your update!
Remember: less is more.
Have a great week,
Greg