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[Podcast] How many times should you reach out to a prospect?

Posted by Ilise Benun on


“It used to be so easy to sell. You could get a person on the phone on the first try usually. By the end of the phone call you’d have a job from them. That ship sailed back in the early ‘90s. It’s a struggle to get people’s attention.”

That’s a quote from my latest podcast/interview with 36-year veteran and time lapse filmmaker, Michael e. Stern, who has honed and adjusted his selling skills over the years.

Needless to say, things are much more challenging when it comes to business development. Here the questions I get from clients and prospects every day:

  • Should I make cold or warm calls? Does it even work? And if so, under what conditions? For what types of projects?
  • What are realistic expectations for this type of outreach?
  • How can you tell if someone is a waste of time, especially if you can’t get through?
  • And when do you give up?

So I tackled these questions in my 3rd podcast in a series of conversations with Michael. And here are a few of our answers….

Half of the people who try reaching out to strangers make one attempt and give up.

25% call it quits after two attempts.

90% are going to drop out by the fourth attempt.

But we all know that 80% of all sales are made after the fifth call. Some people even say 80% of sales aren’t made until after the tenth call.

So the field is wide open if you’re willing to put in five or six or seven attempts.

Here’s the strategy Michael uses to get the 5-figure projects:

Generally speaking, I give people three phone calls and three emails, Then I’m done with them. This may be completely arrogant on my part and I’ll own that if that’s what you want to label it.

On the last attempt I will say, “You know I really wanted to speak with you. It seemed we had a good initial conversation. I was hoping we could talk about some projects but I have to say that I’m not going to call you again. I just have to put my time elsewhere. Thank you and good luck and if you want to reach me please do so.” I’ll end it like that.

It’s pretty bold but I want them to know I decided you’re no longer worth my time and maybe it gets them to rethink, “You know what, maybe I’ll try this guy later.” Initially they do want to reach out but they’re just too busy. There’s all kinds of reason why it doesn’t work out. I pretty much like seven times because I just have to move on to the next person.

Sometimes when I tell someone I’m going to bail on them, I’ll calendar it for six months out, then reach out again to see if that person is no longer in the job or maybe something just hit their desk and this would be a good time to talk. It’s rare that I write somebody completely and totally off.

Listen to the rest of our conversation here….and if you aren’t sure which marketing tools to use, download the Marketing Plan + eCalendar for Creative Professionals here. It will tell you exactly what to do every day to get the work you want.

*Orange phone, courtesy, Shutterstock.


  • More in: Cold Calling, Freelancing, marketing plan, Michael E. Stern, Podcast, Posts by Ilise, time-lapse photography

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