How to do exploratory calls on a job search
A client of mine secured an exploratory call with a CTO last week.
No job posting. No formal process. Just a conversation with a senior leader at a company they were interested in.
This wasn’t their first time, but it was their first time after we started working together. His previous calls didn’t lead to good enough outcomes, so we upgraded his strategy.
Let me walk you through what we talked about so it helps you on your own journey.
Here was the old way:
Prepare like it was an interview. Rehearse a pitch. List accomplishments.
It was like trying to pitch yourself into a role that doesn’t exist yet (or you don’t know about).
And here’s how those typically end:
The senior leader is polite. Says "great chat, let's stay in touch." You never hear from them again.
If that sounds familiar, let’s talk about what to do instead.
Lead with curiosity, not credentials
You’ll probably have to introduce yourself if it’s your first time talking with someone live. You can use my elevator pitch framework for that (my clients use my FIT Pitch writer).
But that’s just the first couple of minutes. This call is going for 15 or 30.
And you probably aren’t able to adapt that pitch to a specific job, so you can go lighter on the details.
Think years of PM experience, 1-2 cool things you’ve worked on recently, and turn it back to them.
And that turn needs to be towards demonstrating your curiosity.
You want to better understand their world before you position yourself in it.
Start with questions like:
What's the biggest problem your team is trying to solve right now?
Where are you blocked—people, process, product, or market?
What have you tried so far, and why hasn't it worked?
What gaps exist on the team to make that happen?
These aren't "networking questions." These are the questions experienced leaders ask each other.
And they do something helpful: they let you decide whether this is a place where you can actually add value.
Most people walk into exploratory calls trying to prove they're good enough.
That’s not the end game.
This is more like a discovery call, and you’re trying to learn what problems or opportunities exist.
And if those excite you, great, now you know how to position yourself better to be the solution.
And if they bore you, also great, now the stakes are lowered and you can move on if you want.
Don't declare your role shape
This one trips up people up a lot.
You walk into the call and say: "I'm looking for a Director of Product role."
Now the conversation is boxed in.
If they don't have a Director opening or that’s not what they need right now, you’ve hit a dead end.
And that’s fine if you’re only looking for a Director of Product role.
But in this job market, some of my clients are happy to flex between strong individual contributor, player/coach, or a pure leader.
The fix is to stay flexible.
Just ask what they actually need:
A strong people leader to build and scale a team?
A player-coach who can lead and ship?
A hands-on IC to go deep on a hard problem?
Let them describe the shape of the gap. Then position your experience to match it.
This is how roles get created for people. Not by asking "do you have an opening?" but by making it obvious you're the answer to a problem they already have.
I've seen clients get offers at companies that had zero open headcount because the conversation revealed a gap the company hadn't scoped yet.
Roles don't always exist before you show up. Sometimes you're the reason they get created.
Always close with a concrete next step
The worst outcome of an exploratory call isn't a "no."
It's a vague "great chat, let's stay in touch" that goes nowhere.
Sound familiar?
That's the inbox graveyard where good conversations go to die.
You have to name the next step.
Not aggressively. But explicitly.
At the end of every call, try something like:
"Based on what we've discussed, what feels like the most logical next step?"
That might be an introduction to someone else on the team. A follow-up with HR. A more detailed conversation about a specific problem.
If they don't offer one, suggest it yourself:
"I'd love to meet someone on your leadership team to keep the conversation going. Would that make sense?"
This is how exploratory calls build momentum instead of dying quietly.
And if moving forward with that company isn’t aligned with where you want to go next, just hit them with this:
"I really appreciate the chat, and this is the exact kind of insight I was looking for. Are there other people in your network you’d be open to introducing me to for another conversation like this?"
It doesn’t have to be those exact words, okay? But you get the gist.
Always think about what the next step could be and keep it going.
Think of it like the growth-hacking techniques used by LLMs to keep the conversation going. But in this case, its growth-hacking for your career.
The best exploratory calls don't feel like interviews at all. They feel like two experienced people figuring out if there's a way to work together.
That's the energy you want.
And hey—if this kind of guidance resonates with you, it’s the exact stuff I teach my clients. That’s probably why you’re here.
My Job Search Accelerator is opening its doors again this week. I’ve got 8 spots and I’d love to have you in the room.
Here’s everything you need to know.