The 5 Questions That Change Every Conversation
A simple question framework to sound strategic, not reactive
Junior professionals answer questions.
Senior professionals ask them.
The right question at the right time demonstrates strategic thinking and leadership—even if you don't have a senior title yet. These five questions come from real executive meetings between Latin American tech teams and North American clients.
"What does success look like for you on this project?"
The Strategy
You're focusing on outcomes, not tasks. You want to understand their definition of success—not just what they need you to do.
Project kickoffs, scope discussions, when receiving new assignments
The Script
What do you need me to do?
This sounds like you're just taking orders.
Emphasize "for you." This makes the question personal and shows you see the person, not just the client.
"...for your team" / "...from your perspective" / "...in your ideal scenario"
"How does this connect to your top priorities this quarter?"
The Strategy
You demonstrate that you understand business cycles. Every project competes for time and money.
When someone asks for something new, budget discussions, resource planning
The Script
When do you need this by?
This only asks about dates, not importance.
Pause slightly before "top priorities"—this shows you're thinking carefully, not reading a script.
"...your board goals" / "...your growth targets" / "...your roadmap"
"Who else needs to be aligned before we move forward?"
The Strategy
You understand how organizations work. Decisions rarely rest with one person.
Before committing to timelines, after presenting recommendations
The Script
Is this approved?
Too passive—you're waiting for permission instead of leading.
Use "aligned" or "on board"—they're more professional than "okay with this."
"What's the risk if we don't solve this problem?"
The Strategy
You shift the conversation from "maybe we should do this" to "we need to do this." You're thinking about consequences.
Budget discussions, priority conversations, when the client seems uncertain
The Script
Do you want to move forward with this?
Too passive.
Drop your voice slightly on "risk"—this adds weight without sounding dramatic.
"If we deliver this successfully, what new opportunities does it unlock for you?"
The Strategy
You're connecting your work to their career goals and business success. You become a strategic partner, not just a service provider.
Relationship-building moments, project kickoffs, when discussing project expansion
The Script
Do you need anything else?
Sounds like a waiter, not a consultant.
"Deliver this successfully" is direct and clear. Avoid casual phrases like "knock this out of the park" in executive-level meetings.
The Pattern
All five questions share these characteristics:
Quick Reference
| Situation | Senior Question |
|---|---|
| Project kickoff | "What does success look like for you on this project?" |
| New request | "How does this connect to your top priorities this quarter?" |
| Before committing | "Who else needs to be aligned before we move forward?" |
| Budget discussion | "What's the risk if we don't solve this problem?" |
| Relationship building | "If we deliver this successfully, what new opportunities does it unlock for you?" |
Robert Cushman
I help Latin American tech professionals communicate with executive-level confidence so they can close bigger contracts, command premium rates, and advance their international careers.
After coaching 200+ professionals from Smarttie, Grupo Kopar, Terramar Brands, and Sourceability, I know that what separates good from great in high-pressure meetings isn't vocabulary—it's leadership communication.