How to Answer Questions From Executives Strategically
Does it feel like you're too in the weeds? Learn how to start with goals and strategy before diving into details to stay strategic and high level in your approach.
(Summer Naps are the Best. Teddy the Corgi, Bay Area, California)
Client: Whenever I’m in executive-level conversations, I consistently feel like I’m not having the impact I should be. When an executive asks a question, my instinct is to answer the question directly and quickly. I then realized my peers were not doing that. Their answers are more strategic. How do I do what they’re doing?
You’re delivering a presentation and a senior leader asks you a question:
“How does this affect other projects we’re working on?”
“How will the Go-To-Market work?”
“How do we architect this part of the feature?”
After taking in a deep inhale, you dive straight into the answer, adrenaline pumping. You attempt to answer the question succinctly and clearly, possibly without drawing another breadth.
“We will need to move 1 engineer from the other project but it should not affect its delivery timeline.”
“For the GTM, we have 3 workstreams planned — Lifecycle, Radio, and Paid ads. We’ll spend $100k across them and will kick off 1 week after the initial launch.”
“For the architecture, we will add a new column to table the user table while we work to refactor xyz.”
After you finish, there is silence. No follow-ups. You continue your presentation. However, you can’t help but feel like you missed an opportunity to sound more strategic. Or to somehow share more.
In another meeting later, you watch one of your peers rattle off goals, expected outcomes, and tradeoffs differently, sounding very strategic, thorough, and…like a true leader. How is she doing it?
What are the Leaders Really Asking?
To uplevel your answers and be more strategic in your responses, it’s helpful to understand the mindset of the leaders in the room and where they are coming from. This way, you can meet them where they are and give them the most relevant information they need to make a decision, rather than (or perhaps in addition to) the direct answer to their question.
First, leaders spend a large amount of their time working across teams and organizations. They are constantly on the lookout for incoming changes in direction that will affect their team roadmaps. They typically want to know if and how what you’re presenting changes the work of their teams and by how much. As a team member, you appreciate this.
Second, most senior leaders and executives are not up to speed on your project. They are busy. They have many projects. They may not remember exactly what the goals of the projects are, what the expected outcome is, and why it’s important to the company. But they always want to know this, because they’ll need to relay this back to their teams.
Third, leaders want to know you’ve done the work and that you’ve given this project the right level of thinking. They want to know that you know who’s for it, who’s against it, what might go wrong, and have covered all your bases on execution. They care less about the exact details versus knowing that someone (you) has thought through it.
So with these three factors in mind, let’s look at how we can uplevel the response and answer the question behind the question.
#1 Start with the Goal
Always take the chance to reiterate the goals and the impact of the project. Yes, it was probably slide #3 in your presentation, but by slide #10, some people have forgotten it. Start with the goals and outcome.
“Great question. As mentioned, the goal of the project is to increase the revenue of product X by 30% through a new multi-user feature that has been preventing larger customers from using our product.”
#2 Give a bit more context
Summarize the relevant context you’ll need to get to the answer. Give them the relevant history and a lay of the land for tradeoffs.
“We’ve prioritized serving our current single-user customers for the last 2 years, have seen growth slow down, and therefore have agreed that it’s now time to invest in multi-user. We’ve had two previous conversations on this new direction, and the slides can be found linked in the appendix.”
#3 Highlight Key Data Points
Use this opportunity to highlight and emphasize critical data or research that drives your decisions. Leaders don’t just want to know what the answer is, they also want to know what data points support the answer. Bring them along.
“This is our first foray into medium-sized businesses with more than 100 employees, and we believe investments here will lead to $300M in additional revenue in the next 5 years. More than 50% of potential customers list a lack of multi-user as their primary barrier to adoption. Our competitors have also touted this as a key differentiator to win accounts in the last 3 of 7 deals we’ve lost.”
#4 Articulate The Strategy
Now that you have everyone nodding along with why this is such an important project, it’s time to start addressing the question at hand. But we’re not quite ready for the “answer” yet. Instead, spend some time articulating the strategy and tradeoffs you’ve considered.
“How does this affect other projects we’re working on?”
To figure out where this project falls in priority, we looked at the tradeoff between impact and cost, and considered how far along work is on existing projects to reduce churn for the team.
“How will the Go-To-Market work?”
“For GTM, our strategy is to rely on current channels where we see the most medium-sized businesses engaging first, adding in multi-user as a top value proposition. The goal is to get awareness and unblock current deals in progress as quickly as possible. Next quarter, we plan to test new channels and iterations of messaging to better optimize spend.”
“How do we architect this part of the feature?”
For the architecture, we are planning to do a quick tweak to launch an MVP of the feature while holding off on some of the more complex logic until after the refactor. For example, you’ll be able to add or delete users, but you cannot edit them. We think this strategy is best to optimize for a Q3 launch time and win deals in the short term.
And finally, if still needed, the very specific answer to the question and the execution detail.
Putting it together
Here’s what it sounds like put together for the three scenarios:
“How does this affect other projects we’re working on?”
Great question. As mentioned, the goal of the project is to increase the revenue of product X by 30% through a new multi-user feature that has been preventing larger customers from using our product.
We’ve prioritized serving our current single-user customers for the last 2 years, have seen growth slow down, and therefore have agreed that it’s now time to invest in multi-user. We’ve had two previous conversations on this new direction, and the slides can be found linked in the appendix.
This is our first foray into medium-sized businesses with more than 100 employees, and we believe investments here will lead to $300M in additional revenue in the next 5 years. More than 50% of potential customers list a lack of multi-user as their primary barrier to adoption. Our competitors have also touted this as a key differentiator to win accounts in the last 3 of 7 deals we’ve lost.
To figure out where this project falls in priority, we looked at the tradeoff between impact and cost, and considered how far along work is on existing projects to reduce churn for the team. We will need to move 1 engineer from the other project but it should not affect its delivery timeline.
“How will the Go-To-Market work?”
Great question. As mentioned, the goal of the project is to increase the revenue of product X by 30% through a new multi-user feature that has been preventing larger customers from using our product.
We’ve prioritized serving our current single-user customers for the last 2 years, have seen growth slow down, and therefore have agreed that it’s now time to invest in multi-user. We’ve had two previous conversations on this new direction, and the slides can be found linked in the appendix.
This is our first foray into medium-sized businesses with more than 100 employees, and we believe investments here will lead to $300M in additional revenue in the next 5 years. More than 50% of potential customers list a lack of multi-user as their primary barrier to adoption. Our competitors have also touted this as a key differentiator to win accounts in the last 3 of 7 deals we’ve lost.
For GTM, our strategy is to rely on current channels where we see the most medium-sized businesses engaging first, adding in multi-user as a top value proposition. The goal is to get awareness and unblock current deals in progress as quickly as possible. Next quarter, we plan to test new channels and iterations of messaging to better optimize spend. Currently, we have 3 workstreams planned — Lifecycle, Radio, and Paid ads. We’ll spend $100k across them and will kick off 1 week after the initial launch.
“How do we architect this part of the feature?”
Great question. As mentioned, the goal of the project is to increase the revenue of product X by 30% through a new multi-user feature that has been preventing larger customers from using our product.
We’ve prioritized serving our current single-user customers for the last 2 years, have seen growth slow down, and therefore have agreed that it’s now time to invest in multi-user. We’ve had two previous conversations on this new direction, and the slides can be found linked in the appendix.
This is our first foray into medium-sized businesses with more than 100 employees, and we believe investments here will lead to $300M in additional revenue in the next 5 years. More than 50% of potential customers list a lack of multi-user as their primary barrier to adoption. Our competitors have also touted this as a key differentiator to win accounts in the last 3 of 7 deals we’ve lost.
For the architecture, we are planning to do a quick tweak to launch an MVP of the feature while holding off on some of the more complex logic until after the refactor. For example, you’ll be able to add or delete users, but you cannot edit them. We think this strategy is best to optimize for a Q3 launch time and win deals in the short term. Therefore, on execution, we will add a new column to table the user table while we work to refactor xyz.
Et voila! It’s quite a long-winded answer no? It’s good to take up air time! And quite strategic sounding? Check.
By walking the leaders step by step from goal to strategy to execution, you bring them along in your thinking, walking them through the trade-offs and decisions you’ve already considered in the process. This enables them to better engage at the strategy and goal level and point out additional considerations or context that may change your approach.