Cold calling for my startup and how I learned to embrace the challenge by@golmansax

Cold calling for my startup and how I learned to embrace the challenge


As a person who gets anxious talking to strangers, I was initially intimidated by the responsibility of cold calling for my startup. If I got nervous from something as small as calling a store to see when it was open, how would I be able to sell a product over the phone? But my startup needed to talk to customers for both sales and product feedback, so I pushed myself to make the calls. A year later, it’s amazing to reflect on how most of my startup’s sales have originated from cold calling and on how I’ve grown to embrace the calling process.

The beginning of the cold calling experience was stressful. For my first few calls, I was so nervous that I spent 15 minutes per call rehearsing a 30 second script and running through all of the possible response scenarios. All of this prep was mostly wasted because very few schools actually picked up the phone. My anxiety also showed in the calls that went through; people constantly told me to talk slower. Despite the anxiety, I still booked a few meetings, which reaffirmed that calling was the right way to reach my customers.

Helpful cold calling book

Eventually, I got more comfortable with practice and refined my calling process with help from Cold Calling Techniques, a book recommended by a friend. Below are a few tips that helped me get over my initial fears of calling and turned me into an effective salesperson.

Call every day

When I first started, I chose Tuesday as the day I would make all my calls for the week. This ended up not being great for me mentally as I would dread Tuesdays and find any excuse not to make those calls.

A huge help to my psyche was committing to making at least one call a day. This forced me to go through the process of getting over my nerves every day, and after a few weeks, I was no longer afraid. In a few weeks, I went from only wanting to make 1–2 calls a day to being okay with making over 10 calls a day. A huge improvement!

Log every call

One of the most useful processes I implemented was to log every cold call I made. There were a few major benefits for this:

  1. I could easily see how many calls I was making a day, which kept me honest to my per day calling goal.
  2. For each call, I logged whether the person picked up the phone and whether a meeting was booked. This made it easy to calculate important stats like pick-up rate and meeting rate.
  3. I also recorded who I was calling and what school they were affiliated with. This ensured I wouldn’t call a school that I already talked to.
A snapshot of my sales spreadsheet

The inspiration for this spreadsheet came from the cold calling book I mentioned previously.

Take notes

Initially when I was only making a few calls a day, I was able to remember exactly what was discussed in every call. I soon realized that this process didn’t scale, as I began to forget important details (like when meetings were booked for) the more calls I made.

Now, whenever I get off a call, I takes notes on anything I feel that I should remember if I talk to that person or school again. These include:

  • Who did I speak to?
  • What name do they go by? (e.g. Jen instead of Jennifer)
  • How did they pronounce their name? (e.g. Jean as in Jean Grey)
  • Did they mention any competitors?
  • If they did not want to meet with me, what reason did they give?
  • When did they say I should call back?

Treat every call made as a win

Especially during the times when I was afraid of calling, I would occasionally psych myself out not to call a school because I didn’t think they would pick up (e.g. Mondays are bad for cold calling) or I didn’t think they would want to speak with me. However, by not calling, I was guaranteeing the worst possible outcome of not speaking to anyone.

Michael Scott said it best (image via The Office-isms)

That is why it was important for me not just to celebrate booked meetings, but also to celebrate made calls. First off, every call is an opportunity to learn about a potential customer. Even when calls went to voicemail, I would note what name the person went by, if the number was a direct line, etc. Secondly, treating every call as a win helped me stay positive when one didn’t go well. From my calling stats, I knew on average how many cold calls I needed to make to book a meeting, and each call I made would get me closer to finding that meeting.

Use your story to your advantage

When I started cold calling, I had no customers other than my former high school — for whom I built the product for — so it made sense to incorporate them into my sales script. However, I didn’t realize how much that story would benefit me until I talked with schools on the phone.

I started every call mentioning that I was a developer helping my high school, and schools would ask about how I got started and what my school was trying. Starting with my story helped the call feel more like a conversation rather than a sales call. And while the story may not have been compelling enough to book a deal, it was at least enough to get someone to stay on the phone.

When you talk to a potential customer, you are selling not only the solution but also yourself. Especially in the beginning when I had fewer case studies and less confidence, my story was an important tool to make the potential customer want to take a chance on me and on BoostMySchool.

I’m extremely thankful that my startup took me down the path of learning how to cold call. Not only am I more comfortable calling in a selling context, but I’ve gained confidence in my speaking ability in general. I don’t get nervous anymore when talking to strangers, and I’ve gotten better at thinking on my feet. This journey has also reinforced my belief that many challenges, however daunting they seem, can be overcome with a combination of persistence, self-reflection, and practice.

Have any questions or thoughts about my cold-calling processes? Tweet at me or email me and I’ll be happy to share!

Originally published at on February 26, 2018.


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