Cold calling: Turning fear into valuable insights

I remember when I first started reaching out to people to see if they'd let me pick their brains about their business processes and pain points.

I was scared of rejection.

I was scared of bothering people.

And if they did say yes to a meeting or call, I was nervous about how the conversation would go or if they'd view it as a waste of their time.

To try to combat that, I would plan my questions and try to follow a formula.

Over time I realized that:

• Most people are cool, and love talking about themselves (let's face it!).

• If someone doesn't want to talk to you, they simply won't respond or will say so (usually politely). So by the time you get to the conversation, they're willing, which means there's no need to be nervous or worried.

• The most valuable conversations are those where I can stay calm and relaxed and let their responses guide me to the pain I am trying to uncover. Trying to follow a prescribed set of questions is much less productive. If I’m ever not sure what to ask next, I simply say "Tell me more about that". The deeper they go, the more pain and value you will extract.

After just a few times of reaching out to people, and having these conversations, I was super comfortable with it and it became something I didn't have to think much about. Yet, I attribute my success to going through this process, as it has been the big difference in how I approached my apps that have ended up doing well and those that haven’t.

I often forget how hard it was to face those fears at first, but I was reminded of that this week with some people I've been mentoring and advising.

I want to share pieces of some of the message they sent me here:

1) This person is exploring different ideas, and after having built some apps previously that didn't result in much, is taking a different approach this time and leading with conversations instead of building.

This is what they said after their first cold call:

This makes me so happy and proud.

Within the short message, I see someone who faced their fears and came out the other side more confident and excited, and learned some valuable insights from having had the conversation.

And here's what followed:

Calls, even cold calls, aren't as bad as we fear, and the insights we walk away with are invaluable.

2) Here's a message from someone else:

This person is in the process of building while simultaneously doing audience research.

Notice there's no mention of the prospect being anything but helpful. They didn't bite!

And can you sense how many valuable insights were taken from this call?

I love seeing "[they] are worried" - that's pain right there!

There's no better way to get inside the head of your customer than to have conversations like this no matter what stage you're in.

Hopefully these stories inspire you to face any fears you have around starting conversations with prospects or customers and to recognize the value you are bound to walk away with if you do so.

P.S. I recently opened up a new offering of mentorship via 1:1 chat (Discord) as a monthly subscription (this is where one of the conversations originated).

The price increases by $50 each time 5 slots are filled in the given tier, but once locked in your price will never change. The $49 tier has sold out. Grab a spot now at $99 before it jumps again.

-Mac