If you’ve ever landed a coffee chat with a senior executive, you know it can feel like a golden opportunity—and a high-stakes one.
You want to impress.
You want to connect.
You want to make it count.
But too often, these chats end up feeling… forgettable.
Why?
Because most professionals show up with generic questions like:
- “Can you tell me about your career path?”
- “What advice do you have for someone like me?”
- “What’s your leadership style?”
There’s nothing wrong with those questions—but they don’t make you stand out.
If you want to build a real connection and be remembered after the meeting ends, you need to ask questions that make executives pause, reflect, and say, “That’s a great question.”
Let’s talk about how to do exactly that.
The Real Goal of a Coffee Chat
A coffee chat is not about pitching yourself.
It’s about building a relationship, showing curiosity, and demonstrating the way you think.
You’re planting a seed—one that could grow into mentorship, sponsorship, or even an opportunity down the line. To do that, you need to:
- Show respect for their time
- Ask questions they don’t hear every day
- Leave them thinking, “I’d like to talk to this person again”
5 Powerful Questions That Leave a Lasting Impression
Here are five questions that will help you stand out, spark meaningful conversation, and be remembered:
1. “What’s something you know now as an executive that you wish you’d known earlier in your career?”
This invites reflection—and gives you insight into how they think and what they value. It also flatters them by acknowledging their experience without sounding forced.
2. “What do you look for when deciding who’s ready for a bigger leadership role?”
This is a strategic question that opens the door to insights most people never hear. It gives you inside information on how promotions are really decided—and subtly signals your own ambition.
3. “What’s a tough decision you had to make recently, and how did you approach it?”
Executives often operate in grey areas. This question gives you a window into their judgment and leadership style—and shows you’re thinking at their level.
4. “What’s one thing rising leaders in this company often overlook?”
This shows you’re focused on growth and willing to challenge blind spots. It also gives them a chance to share advice that feels specific and actionable.
5. “What’s the best way for someone in my position to contribute more strategically?”
Instead of asking, “How do I get promoted?”—this reframes it around impact. It demonstrates that you’re already thinking like an executive: focused on outcomes, not just tasks.
Bonus: The Follow Up That Most People Forget
Don’t end the chat with “Thanks for your time.” Instead, follow up with a thoughtful note that does three things:
- Thanks them again
- Mentions one insight that stuck with you
- Offers a small value-add (an article, reflection, or project update)
This turns a one-time conversation into an ongoing relationship.
What Should You Do Next?
Here’s how to turn this into action—starting this week:
1. Schedule One Coffee Chat
Look at your calendar and reach out to someone more senior—ideally someone you admire or want to learn from. Keep the ask simple and respectful:
“Would you be open to a quick 20-minute chat over coffee? I’d love to learn from your experience.”
2. Choose 2–3 Great Questions
Pick a few from the list above (or tailor your own). Focus on the ones that show curiosity, thoughtfulness, and strategic thinking.
3. Be Present and Listen Well
Remember, this is about connection, not performance. You don’t need to impress—you need to be real, engaged, and intentional.
4. Send a Thoughtful Follow Up
Within 24 hours, send a short message thanking them and reflecting on what stood out. Bonus: mention how you’ll apply what you learned.
5. Repeat Monthly
Start making this a habit. One meaningful conversation a month can change the trajectory of your career over time.
Notes from Drew
When I was working toward my first executive role, I assumed hard work would be enough.
But over time, I realized the most important career doors didn’t open because of what I did—they opened because of who knew me, trusted me, and believed in me.
That trust started with simple conversations.
Not pitch meetings.
Not performance reviews.
Just coffee chats.
The kind where you ask a great question, share a bit of yourself, and let the relationship build naturally.
Executives don’t promote resumes.
They promote people they believe in.
If you want to lead at the top, start by having better conversations today.
You’ve got this.
