< Back to All

Never Make a Cold Call Again

March 16, 2022

By Derek Dickow, originally featured in our FOCUS magazine

Is there a moment in your career when you decided cold calling was not for you?

I remember it vividly.

It was late in 2009 when I made a professional transition into the world of political and non-profit fundraising. I was relatively unknown to my client’s industry (a non-profit trade association) and to the world of fundraising overall. As such, I was provided with a commissionable opportunity to sell memberships, advertisements in their monthly magazine and sponsorships for their annual gala.

I didn’t personally know anyone who would join the association, pay $2500 for an ad, or donate $5000 – $25,000 to sponsor an event. But I needed to make a living, and this was the exciting new career path I had chosen.

I dove in headfirst.

On my first day, I was directed to my client’s conference room, given a landline, piles of (mostly old) leads, a bottle of water and the well wishes from the executive director—“Good luck. Let us know if you need anything.”

I learned a lot about cold calls after the first week—I hated them. I didn’t enjoy hoping people would answer, having to explain how I got their number, or why I was bothering them at dinner time.

I believed in the mission of the organization and was confident I was creating value for both my client and the prospect. But I needed to quickly create a better reason for why anyone should listen to me, or it would be a wasted opportunity. So I learned to make cold calling easier—I turned a cold call into a warm call by researching as much as I could about the prospect before even picking up the phone.

Here’s how it worked:

I leveraged Google and yahoo!, studying the prospect’s business and personal history. I asked my colleagues at the association for background. I cajoled gatekeepers and made small talk with every executive assistant, always learning and repeating their names (something my uncle, lawyer Ron Acho, taught me). I shared quick jokes (but never talked about the weather or traffic), and mentioned that I’d much rather visit their office and bring them a coffee than call them (which I did from time to time).

I’d ask the prospect’s staff everything I could to learn about the big boss before ever asking to be transferred: Questions like:

“Remind me. How long ago did the company get started?”

“Who’s your ideal client?”

“What’s important to the company?”

“What’s the biggest issue your boss is focused on?”

When I finally had enough to sustain a decent (albeit brief) introductory call, I’d reach out to the big boss and start with what I knew about them. I’d say something like:

“I’ve read about you, and I’m interested in learning more about your business, and more importantly, how I can add value to your business. I know we don’t have a scheduled call today, so I’ll keep it brief. Would you tell me a little about your ideal customer and what separates your company from your competition?”

Then, I’d pause and listen.

I engaged more and conveyed my curiosity as to why they weren’t members of the association, what they needed as a ROI for their membership, who they needed to meet and what was holding them back from sponsoring the upcoming gala.

Then, I paused and listened more.

After our initial call, I’d get creative with sponsor packages and call them back to make deals specific to their goals.

This was a rinse-and-repeat model leading up to my client’s annual gala, where we generated significant revenue selling sponsorships and ads, as well as signing up new members. After a few months, my client provided me with an office, a proper retainer, success fees and a title. I had figured out this cold calling thing!

Fast-forward more than a decade. I’m soliciting some of the most successful business leaders in America for substantial political contributions with calls that sometimes last no more than two minutes.

By turning cold calls into warm calls, I parlayed much of my methods to reach these leaders. With the following simple steps, here’s how you can do this, too:

  1. Identify your target and set a timer for 60 minutes.
  2. Leverage Google and all social media platforms. Call assistants, employees or anyone that is a mutual contact to get a snapshot of the prospect. You want to learn who they are, and uncover their wants, political and philanthropic interests and usable information specific to their industry (be it a trend or statistic).
  3. Write the top three or four points of information you’ve gathered on a sheet of paper in order of what will capture their interest first. Here’s a hint—it won’t be what you’re trying to sell. It must be about them and directly related
    to what you learned from your research.
  4. Capture their attention. From my experience, you have about eight seconds to captivate a decision maker before they hang up to attend to more pressing matters.

Start the call like this:

“Hi Cynthia, I know we don’t have a scheduled call. My name is [your name], and I read about your recent [two quick points of information]. I’d like to ask a few follow-up questions. Is this a bad time? I’ll be brief.”

Then pause.

“Great. The reason for my call is, through my research, I noticed we are both supporters of [insert college, political, philanthropic, or relevant commonality, etc.].”

Finally, “I know I asked you for a few minutes and our time today is up. May I circle back with you in a few days or a week to present an idea that I’m confident will add value to [your organization, family, charity, etc.]?”

Or, if you need to close them now:

“Since I only have another minute, are you ok with me making a brief ask?”

Then make the ask, and pause.

You might be thinking, does this work?

Let me tell you about the time billionaire philanthropist, Stephen M. Ross, Chairman of Related Companies, was on my call sheet for one of my political clients. If you don’t know Stephen M. Ross, he is the single largest benefactor to the University of Michigan, and the Ross School of Business is named after him. He’s the developer of the Hudson Yards, one of the most expensive real estate developments in the history of America. Yes, that Stephen M. Ross.

Some might try their luck at cold calling him, or instead, you could take my warm call approach instead.

Within 15 minutes of research on Wikipedia, I learned he is the nephew of Max M. Fisher, the preeminent businessman and pioneer of the metro Detroit Jewish community from a generation ago. That makes Stephen, the cousin of Phillip Fisher, who is a friend, a mentor and philanthropic leader I’ve known for years.

Coincidentally, Phillip sent me the book “Quiet Diplomat,” written about his father to help advance professional growth. Now this isn’t some ordinary book. It’s 500+ pages on the life of one of the most successful, benevolent and caring leaders in the history of our country, and the world for that matter.

So how did I turn this Stephen M. Ross call from cold to warm? I read the entire book before picking up the phone.

It took me a few weeks before I was ready. I had to stop and turn to Google to learn more about Max Fisher’s life. I had to draw a connection.

In addition to gaining information, I was genuinely inspired by the book. It changed me in great ways, especially as a fundraiser and relationship builder. I understood Max’s passion and drive to help his community and country. And within my notes, I found the points of information to share with Stephen to separate myself from any other solicitor that ever had the chutzpah to call him.

I made Stephen laugh. He asked, “You read the entire book?”

“Yessir, I did.”

He replied, “Tell me, how can I help you young man?”

In total, I researched 12 hours to craft an eight second opening to bridge a three minute pitch, which eventually led to a substantial contribution for my client.

I promise you this works.

When you’re out there soliciting, calling on prospects and doing everything you can to put food on the table, be mindful that research matters; your up front, due diligence matters. It’s that investment—the extra time you take to know who you’re talking to—that helps you win in business in America today.


Derek Dickow is a keynote speaker, executive coach and power connector known for facilitating high-potential introductions. He’s raised tens of millions of dollars and the profiles of projects, political candidates and charities he’s passionate about. Visit derekdickow.com for more.

Share On: