Adventures in Sales #2: Losing and Regaining Confidence

female sales person on phone call

“You’re trying to sell to Fortune 500 companies?? And you’re doing this all by yourself, with NO experience? WOW, I couldn’t imagine being thrown more into the deep end than that!”

I was on a call with a sales professional I had connected with after reading his book, and he evidently thought there was no way I’d be successful. He had been a fractional VP of Sales for 20+ years and was a prominent figure in my local sales community. His words definitely shook my confidence.

“But it’s great that you’re taking the initiative to read books and improve your sales skills – lots of people don’t take the time to do that.”

Well, at least I had that going for me! We talked about sales a bit more and I thanked him for connecting. But his words made me rethink taking on my new role. Like lots of people, I had a mental image of an experienced sales pro who always knew the right thing to say and could win anyone over with their graceful conversational skills.

In contrast, I felt awkward picking up the phone, believing I’d say all the wrong things or not know the answers to the most basic questions.

Then I remembered what Mary Jane had told me about looking for ways to connect with people on a personal level and spark a genuine conversation. I realized that since starting my new role, I had become increasingly interested in the field of learning and development. I continually asked my colleagues a ton of questions about their work and knew that I remained deeply curious. 

I decided to use this enthusiasm to kick off my conversations.

So one of the first things I told prospects was that I had just started my first role in the industry and how excited I was to connect with them and learn about their company’s programs. As well as being a starting point for conversation, I figured if people knew I was brand new, they’d probably expect me to say the wrong thing from time to time!

Fast forward to my first meeting…

And my prospect enthusiastically congratulated me on my new role, welcomed me to the industry, and asked what she could do for me. While it didn’t exactly feel ‘smooth’, I asked lots of questions about her team’s current needs and challenges and listened carefully, expressing my genuine interest in her work, her team and the company.

It turned out they were looking for new vendors and would be making decisions over the next couple of months – perfect timing. Considering they’re one of Canada’s top employers with 10,000+ staff, I was thrilled the conversation had gone so well!

Will it turn into a sale?

Only time will tell – but I was really happy to have had such a positive first conversation, and it made me feel a lot more confident about picking up the phone. 

In the meantime, I’ve been leaving lots of voicemails, sending follow-ups, and navigating a seemingly endless stream of summer holiday autoresponders.

What remains top of my mind is that I’m working with my new company on a trial basis, and my contract will be extended after reviewing my first few months go of outreach to prospects. I’m really enjoying this sales journey so far, so fingers crossed – stay tuned to find out if I can pull it off!

With this series of posts, Tegan Samija is sharing with us, in real-time, how she navigates learning to sell … everything from picking up the phone, speaking with potential clients and booking meetings. I’m joining her on this journey as her occasional coach and I’m really pleased that she’s agreed to write about the experience. 


Closing a sale is the natural outcome of inspiring great conversations and listening intently to our potential customers.

This natural approach still involves a process – a plan that moves potential customers through a journey of discovery with you. So ... what's your process? And am I the right sales coach for you? Let's find out.

2 thoughts on “Adventures in Sales #2: Losing and Regaining Confidence”

    • So glad that you’ve agreed to create these updates, Tegan. They are valuable for all of us who spend time on the phone as part of our sales and business development activities.


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