5 Things Downhill Skiing Taught Me About Sales Coaching

Why is sales coaching important?

Just months ago, I jumped into my first sales development job ever here at Lessonly. To say that I was fearless of my transition into a completely new career and industry would be a lie. This new job meant my first time in the SaaS sales training space, a drastic culture change, a significantly longer commute, endless skills to learn, and 170 new names. 

Since day one on the job, I’ve been comparing this journey to my early days on snow skis—I spent a lot of time learning how to get down a run without injuring myself. And while I’ve never once been scared of throwing out a knee or taking a nasty fall at work, I am constantly thinking about the people and processes that help make those metaphorical falls less frequent. So, you might be asking, “What does skiing have to do with sales coaching?” Here are a handful of ways I think they carve together.

1. Don’t be afraid to fall

One pivotal thing to always remember when starting out skiing is that you can’t be afraid to fall. If you’re picking up too much speed and can’t stop yourself, you have to accept the fall, and learn from that mistake. Eventually, you’ll need to learn how to stop. 

In sales, learning from your mistakes is important as you progress through your development. When thinking about sales coaching best practices, one of my favorites is that our managers coach us by providing honest and kind feedback, challenging us to get better, and supporting us in taking risks with creativity. If something fails, at least we took our chance at the slope and come back having learned something. 

2. Start slow, have patience

Life has taught me that most good things come with patience. When I started to ski, I naturally wanted to join my brother and cousins on the big hills, but I obviously couldn’t keep up at the time. I had to work my way up to bigger slopes, and I knew that with practice and coaching, I would get there. 

When I started my sales development role at Lessonly, I also naturally wanted to start hitting quota the first month and contributing to the team along with the more experienced teammates, but I learned to rely on the numbers. Our managers coach us to understand metrics and how they help diagnose where to improve, but it takes patience. 

3. Get a lesson from a trainer

My dad was my trainer when learning to ski, and if I didn’t accept or listen to his guidance, I would’ve never been able to develop and eventually ski on significantly bigger mountains and extreme runs. The same goes for listening to my managers at Lessonly. Starting out, I needed to indulge in sales training courses for beginners and make myself teachable and adaptable to different situations and sales coaching techniques.

4. Positioning is key

Beginners need to focus on the basics—knees bent and legs parallel. Understanding proper positioning on the slopes allows a skier’s body to absorb bumps and moguls instead of being rattled by them. My managers’ sales coaching styles took a similar approach and engrained that we should not be afraid to pivot, but always remember the basics of putting the customer experience first.

5. Be consistent

I quickly realized that constantly changing your approach to skiing without fine-tuning the core skills would be detrimental to my long-term success. In my time at Lessonly, I’ve learned that consistency is key, especially in my individual sales coaching with my manager. We have weekly 1-on-1 meetings, and one thing we really value is being consistent with those. The frequency and length of our 1-on-1s will fluctuate depending on the week, but what matters most is that we are having them. 

Sales reps need to know someone is always on the slope with them, celebrating where they’re winning and providing tips on new ways to improve. In the same way that consistency in skiing builds confidence, consistency in coaching relationships allows reps to feel vulnerable enough to ask for feedback, learn, test new tactics, and ultimately grow.

Practice is for more than skiers 

To wrap up, I’d like you to think about your favorite athlete. They are constantly practicing their skills and learning new ways to perform. We believe businesses should be doing the same thing. That’s why we built Lessonly to make learning and practicing easy for busy teams. I hope this contrast between skiing and sales coaching will help you as you evolve your sales training curriculum

Below are two pictures of very different times in my skiing journey. The goal one day is to have similar recollections on my sales career of how I’ve sculpted my skills to best help our customers. 

Me (right) preparing to learn how to ski in 3rd grade!
Me (middle) Skiing in Utah, February 2020!


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