#tbh - Asking the Wrong Questions Is Holding You Back

To be honest, I received a DM recently that stayed with me longer than it probably should have.

An artist wrote to me asking where he could send his music, because he had heard that I’m a manager in Berlin.

I asked him a simple question back.

What should I be listening for?

His answer was that he wanted to know what kind of artists I work with, and what I could do for him.

I don’t think I need to explain why this threw me off.

He was pitching to me so that I could pitch myself to him.

And this isn’t an isolated case.

I see the same pattern again and again, not only in DMs, but also inside the course I’m currently running. There’s often a big gap between what people say they want and what they actually put on their to-do list.

One thing stands out in particular.

Many people don’t know how to ask the right questions.

I see participants sitting in front of some of the best guest speakers they could realistically have access to. People with years of experience. People who have made mistakes, learned from them, and built something real.

And yet, the questions they ask are often about templates.

How to write this email.

What wording to use.

What structure works best.

That’s where things start to go wrong.

Not because templates are useless, but because they become a way of avoiding the harder work. The thinking. The positioning. The clarity about what you actually want and why.

If you don’t know what you’re asking for, no template will help you.

If you don’t know what you’re trying to build, no manager, agent, or mentor can magically fill in that gap.

Authenticity doesn’t come from wording.

Uniqueness doesn’t come from structure.

They come from understanding your own direction well enough to ask questions that actually matter.

Instead of asking, “How should I pitch?”

It might be more useful to ask, “What am I really trying to communicate?”

Instead of asking, “Who should I send my music to?”

It might be better to ask, “Why would anyone care about this right now?”

Instead of asking, “What can you do for me?”

It’s worth asking, “What am I already doing, and where do I actually need support?”

When those questions aren’t clear, the responsibility quietly gets pushed onto someone else. Onto an agent. Onto a manager. Onto a guest speaker. Onto a template.

And that’s usually when things stall.

I don’t say this to discourage anyone. I say it because learning to ask better questions changes everything. It changes how conversations go. It changes how people respond to you. And it changes how seriously your work is taken.

The people who stand out aren’t the ones with the cleanest emails.

They’re the ones who know why they’re reaching out in the first place.

alma x