Adventures in Sales #4: Even When You’re “Weirdly Lucky” There’s More to Learn

woman talking on the phone while looking at computer screen

This week I’m just over four months into my new sales role and it’s been quite an exciting journey. Of course, not without some bumps along the way!

A quick refresher for anyone new to my adventures in sales – I started making my first calls in July with zero experience in sales or in the industry I’m selling in. Knowing I’d have a lot to learn, I quickly enlisted Mary Jane’s help to connect with prospects and have great conversations.

In my last update, I shared how I overcame my struggle to book my first calls by experimenting with targeting and outreach. Since then, my success rate in booking calls has steadily increased as I’ve gained experience. Most recently, I’ve booked calls with 43% of the people I’ve reached out to, resulting in 28 calls booked – while working part-time.

Each of my calls has been with my ideal prospects at amazing companies, and almost everyone has expressed an interest in having additional discussions. The conversations have been flowing! While I do schedule short 20-minute meetings, some of my calls have lasted up to an hour as prospects share details about their current training programs and various challenges they’re facing.

Describing my experience to Mary Jane, I told her my conversations have even been weirdly lucky! In almost every conversation, I’ve been able to identify a prospect’s need for which my team’s training solutions could be a potential fit. For example, one prospect’s company recently made two acquisitions and needs to quickly develop training for hundreds of new staff. Another, with only one learning and development employee in the organization, is looking for additional external partners to support upcoming programs.

However, despite the opportunities I’m uncovering, a new worry has been sneaking up on me and making me wonder if I’m really on the right track. I’ve moved from being concerned about my calls being ‘too salesy’ to thinking they aren’t sales-focused enough.

Although I’m having high-quality conversations, I still need to figure out how to book follow-up calls for these prospects with my colleagues. I need to keep these conversations going and allow the prospects to learn more about how we can become their training partner.

And another worry is … am I working hard enough? Things feel too easy. Surely I should have to reach out to hundreds of people just to schedule a few calls?

When I mentioned my worries to Mary Jane, we strategized about how to bridge the gap between my initial calls and booking a second conversation with my colleagues. She was emphatic that my being “weirdly lucky” with uncovering opportunities on my calls wasn’t luck at all. It’s the result of my allowing my endless curiosity to guide my conversations and actively listening.

To start booking follow-up calls, I need to share with prospects how these opportunities indicate the need for a second conversation. That there is value for them to learn more about our work and how we can serve. This is the path to having them say “yes”. As Mary Jane says, the prospect is the one who books the meeting – not me!

That means my next challenge is to leverage all the energy and enthusiasm I’m encountering on my calls to book secondary conversations that will help my prospects reach their goals. Stay tuned to find out if I’m able to book my first follow-up calls over the next few weeks.

On another note, I mentioned in my last update that my new sales work was on a part-time trial basis and I would soon be finding out if I would get to continue in my role. I’m excited to share that my contract has been extended and my hours will increase starting this week. I’m really excited about this next step in my journey and looking forward to sharing it with you. 

And I’m wondering … what’s your reaction to being “weirdly lucky” in sales? What are you doing to create this luck for yourself? Share your ideas and stories in the comment section below. I’d love to learn from you.

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, sending out LinkedIn messages, 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.

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What's The Phone Lady doing?


  • Remote learning experiences + one-on-one coaching for women entrepreneurs (More info about this three-year program here.)
  • Team and individual coaching with a national moving company to refine their sales process
  • Remote half-day training for provincial tourism representatives
  • Remote seven-part sales training program for US-based SaaS
  • Remote webinar on accounts receivable communication for industrial-services company
  • Remote webinar on validation to college students in entrepreneur program
  • In-person workshop on job search skills for women in the trades
  • Remote half-day webinar on written correspondence to customers

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