4 Things I Learned During My First Year in Sales

And what I’ll do differently in 2021

C. T. Chancelor
Scott D. Clary
5 min readJan 4, 2021

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2020 was a tough year for people in plenty of industries and salespeople were some of the ones whose jobs were impacted by the global pandemic. As we turn towards setting our goals for 2021 it’s important to look back on the previous year, think about our experiences, and recall what worked and what didn’t — and why.

Success is driven by continuous improvement and self-reflection is one method we can use to help us get there. Here are 4 of the most impactful lessons I learned this year.

1. Someone is Always Buying

I promise this will be the only COVID-related point here.

I spent a lot of time and effort this year chasing around “prospects” that I thought could use my goods and services even if they didn’t necessarily align with their current needs. A $100,000 customer isn’t worth a penny to you today if your services aren’t of meaningful value to them.

COVID took this concept and injected jet fuel into its veins. Many industries were hit hard for a significant portion of 2020 and are just beginning to recover, but plenty of other market sectors actually grew this year. I probably spent too much time pitching to customers that did well in the past but were simply not expending capital in the foreseeable future.

While there is something to be said about consistent touch-points with your prospects regardless of their current needs, your job as a salesperson is to drive growth and bring in new revenue. Someone is always buying and your time will be spent most efficiently working with and finding those prospects.

2. A True Prospect will do the Legwork

So, you just found a huge opportunity with a prospect. Great! Now what?

Regardless of your business or service, closing that deal will require at least some amount of buy-in from the prospect. This can come in many forms: providing additional documentation, information, contacts, etc.

Oftentimes as the salesperson we see the potential and want to drive that opportunity home so we can hit those sales goals and see our hard work reflected in that commission check at the end of the month. How many of your opportunities have died in limbo? How many of your prospects have dodged your phone calls after a meeting that was seeming full of potential for both sides?

There are plenty of reasons why this happens. Sometimes things change and you get left out of the loop. Maybe you were unknowingly doing some free consulting (“I just want to pick your brain on…”). Perhaps your contact sees considerable value in the product or service but doesn’t know how to present this value to their bosses. What do we do about this?

Learning to set expectations with your prospects and asking deeper, more thoughtful questions in the initial conversations can help keep you out of this quicksand trap. You know, the one where it seems that despite all the time and resources you have dedicated to the opportunity that it is still stuck without a decision? Here is an example:

Salesperson: Mr. Prospect, we’ve been working on this opportunity for 3 months now. I know when we first started working together on this the expectation was that a decision would be made by the end of the first month and it feels like we’re not making progress anymore. Did something change?

Prospect: Oh you know, we’re still thinking it over.

Salesperson: Mr. Prospect, usually when my customers tell me they want to think it over some more it means that they’ve decided not to move forward on this opportunity — and that’s okay. I want you to be comfortable telling me no because I’d much rather be working with you on things that are making an impact on your bottom line and maybe this project wasn’t that for you this time. Is that what is happening?

I for one spun my wheels far too long on opportunities that had gone cold simply because I didn’t want to give up on the sale. Save yourself the frustration and don’t be afraid to go for the no as early as possible. If your product or service is truly valuable to your prospect they will help you get to a purchase order because it is something that will make an impact for them and their business — not just you and yours.

3. Lean on Your Mentors

This is something I believed walking into this role but it wasn’t something I had gotten much of a chance to practice in college or my part-time jobs. Whether it is a sales leader, colleague, or manager — find someone that is the best at what they do in the company and be a sponge. Mentorship is a huge driver of future success and to miss out on the opportunity to participate could be stifling your growth.

How you do this can be achieved in many ways. Remember to be respectful of others’ time — they have a job too and likely have many responsibilities. Ask them out to lunch. You’ll be surprised how willing some people are to help and pass along their knowledge. Here are some ways I have leaned on my mentors this year:

  • Schedule a debriefing of a sales call I went on recently to see where I can improve
  • Ask a technical leader to teach a concept during the next scheduled meeting
  • Discuss strategies and tactics over lunch
  • Read/watch content from “virtual mentors”

Sales is often a solo act so a second perspective is an incredibly powerful tool you can use to improve your game. Lean on others’ experiences and ideas to help you grow. The ideal mentor would be one that is in a position of sharing in your success as their mentorship would be mutually beneficial to both parties — not just you!

4. Get to the Decision-Makers as Fast as Possible

If there is only one thing you take away from this article let it be this:

If you are not pitching to the decision-maker(s), you are relying on your prospect to sell for you.

Think of it another way. Would you want your mother to sell your product or service for you to one of your biggest prospects? Okay, pretend she wasn’t a rock-star salesperson. The point is that no one at your prospect’s company is going to be able to sell your product or service better than you. They know their problems and you know what you sell. The more buy-in you get from the influencers and decision-makers the more likely you are to close the sale. You are more likely to do that if you are the one delivering the pitch, asking questions, and handling objections. It is your job, right?

Remember, everyone wants to feel important and valued. If you directly ask, “who is the decision-maker?” The implication is that it’s not them. You can find a great list of softer qualifying questions here.

Have anything you learned this year that you’d like to share? Leave a comment below. Here’s to 2020 and a better 2021.

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C. T. Chancelor
Scott D. Clary

Automation | Sales | Robotics | Programming | Productivity