Start With Your Scariest Prospect First: Turning Nerves into New Business

Let’s be real—cold calling a tough prospect is like diving into a pool you know is going to be freezing. You inch up to the edge, look down, and think, Maybe if I just do everything else on my to-do list first… But there’s a magic in facing your fears head-on that not only builds confidence but often results in your best work. And in the world of prospecting, this translates into success.

Why Start With the Scary Ones?

Here’s a little trick I’ve learned from too many afternoons spent almost dialing numbers: starting with the hardest prospect first changes the entire game. Think about it: once you face the person who’s practically a stuff-of-nightmares type, every other call feels like a walk in the park.

Let’s say you have two prospects. The first is someone who’s likely to need a little hand-holding, and the second is, let’s just say, Mr. Unreachable. We all have a “Mr. Unreachable” on our list, right? This is the prospect you’re convinced was born to slam phones and ask questions no mortal would think to prepare for. But, the confidence you gain from tackling them first is like a one-way ticket to feeling like you can conquer anything that follows.

My First “Scary Prospect” Call

I still remember my first attempt at calling a “scary” prospect early in my career. I rehearsed, practiced my calm “professional” voice, and hyped myself up with a “you’ve got this” pep talk. But when I dialed, my hand was shaking, and my mind was running through a greatest hits list of “What if they hang up? What if they say no?”

Turns out, they did say no. But they also respected my persistence, and in the end, that prospect gave me the best feedback of my early career. They even recommended me to someone who actually became a client. From that day forward, I realized the toughest calls are often the most worthwhile.

The Science Behind Facing Fear First

Now, it’s not just me saying this—there’s a whole load of science backing up why you should tackle your fears head-on. It’s all about that sense of accomplishment. By getting the hardest call out of the way first, you experience a psychological “win” that boosts your mood and energy. Think of it like weightlifting for the brain; once you’ve lifted the heaviest weight, the lighter ones are a breeze. It’s this dopamine hit that makes the rest of the day’s tasks feel, well, less terrifying.

Starting with your toughest prospect first can also reduce procrastination (which we all know can be a sly monster). Putting it off means you’re carrying that tension all day, draining mental energy you could be using on more productive tasks.

Here’s How to Actually Do It

So, how do we face that first scary prospect and turn them into a success? Here are some pointers that have worked for me—and might just do the same for you.

1. Hype Yourself Up: You don’t have to be a cheerleader to benefit from some self-motivation. Whether it’s a favorite song or a quick victory lap around the office, get yourself in a positive frame of mind before you dial. Confidence is key, even if you’re faking it a little.
2. Picture Success: Visualize a positive outcome before you make the call. If you think it’s going to end in rejection, that nervousness seeps into your voice. Picture yourself smoothly handling every objection, and you’ll be more likely to stay calm and collected.
3. Prepare for “No”: If you go into a call dreading rejection, that’s exactly what you’ll get. But if you’re open to whatever happens, it’s a lot easier to roll with the punches. Expect objections—no big deal! The more you practice hearing “no” and calmly countering it, the more it becomes just another word.
4. Follow Up Like a Pro: So maybe the first call doesn’t land a deal. But remember: the call isn’t over until you say it is. A great follow-up game can often turn a “not right now” into a “tell me more.”

Turning Nerves into Your Next Client

Once you’ve made that first call, you’ll notice something remarkable. It’s like the pressure releases, and every call afterward feels way easier. The same principle applies to just about everything—whether you’re writing a pitch email, giving a presentation, or reaching out to a high-level contact. After facing the toughest hurdle first, you build momentum, and with it, a sense of accomplishment that fuels the rest of your day.

A Final Thought (and a Little Pep Talk)

We all know that sales isn’t for the faint of heart. But the best way to handle fear is to stop letting it call the shots. Starting with your scariest prospect first puts you in control, and that shift in mindset makes every future challenge feel a little less daunting. And hey, when it all works out, you’ll have the best story to tell your friends over coffee.

So next time you look at your prospect list and see that one name that makes your stomach do a flip, take a deep breath and dial. After all, the only way out of fear is through it, and chances are, it’ll be the best call you make all day.

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