5 Mistakes I Made My First Year in Sales

When I entered the startup world over a decade ago, one of the first lessons I realized was that sales drives everything. If you don’t have any sales, you won’t survive. So in this article, I’m going to dig into five of the biggest mistakes I made in my first year in sales. This way, whether you are a sales rep or thinking about going to sales, or it’s just side hustling in selling something, you will be able to avoid making these same mistakes in your sales journey.

Mistake 1: Thinking of my demos like checklists

Whenever you first start to sell something, you get into this tendency of thinking about all the features and benefits that you love to tell your prospect. But the reality is that your prospect, frankly, doesn’t care all that much about hearing every single one of those features. What this tends to lead you to is having really predictable demos. Demos that don’t really change to the different needs of your prospects and what they might be looking for in your service or product.

In the hundreds of final rounds sales interviews that I’ve run, this is one of the most common mistakes that people make. They get so caught up in making sure that they can demonstrate to their interviewer, that they learned all the things about the product that they don’t actually listen and think about what the scenario is in terms of the person that they are selling to in the roleplay.

To avoid making this mistake what I recommend is that you qualify upfront to really, really well. And then from there, outline your roadmap for the rest of your sales based off of what your prospect is telling you.

Mistake 2: Sending long follow up emails

The second mistake that I made in my first year of sales was sending super long follow-up emails. This goes hand in hand with mistake number one. And I think it’s just because in your first year of sales, you’re not really sure what your prospects want or need from you. And so you tend to send these follow-up emails that have every single case study or resource that your marketing department has given you to the prospect. The problem with this is that it overwhelms your prospect.

If you’re giving too many things for them to check out in the follow-up to your call, then they’re just going to end up checking out none of them, because you’re giving them too many options. To fix this, all you need to do is think about what you think would be most valuable to your prospect based off of the conversation you guys just had.

Maybe for example, they just talked about how they are trying to solve X, Y, Z problems. And you’ve got a case study that shares how one of your customers solve that exact same problem. That would be the best resource in that situation to share with your prospect. What I found was that by taking a step back and pulling back my follow-up emails so that they were shorter, more concise and just sharing one or two resources, I was able to significantly increase the engagement rate of my follow-up emails.

Mistake 3: Not holding everyone accountable

For the third mistake I made in sales, it was not holding everybody accountable in my calls. Meaning both me and my prospect. It’s often in your first year of sales that you’re not going to do enough nurturing or back and forth conversations with your prospect. What this means for you is that you will often leave money on the table that would have gone towards your quota.

Something that I quickly learned in my first year was that it was really important to clearly outline the things that I wanted for my prospect for the next time that we connected. In other words, at the end of my sales calls, I would provide some key takeaways and then also summarize what they could expect from me as well as what I expected them to have achieved by the time that we next connected.

By talking about the sort of accountability openly, it actually gave me an opportunity to then close the loop later on in my follow-up sequence. And this is because I could just send them an email a few days later saying, “Hey, have you gotten the chance to doing XYZ as we discussed.” Not having clear accountability is a mistake that I wish I had avoided making in my first month of sales because I know it costs me a ton of sales.

The reason why is because your prospect quickly forgets about you. If you think about the 30 minutes that they spent with you, it only represents about 1% of their entire typical workweek. So why would they care all that much about your service? By having clear next steps and desired goals in the next time the two of you connect, you make sure that there’s still momentum in the deal that you’re working on.

Mistake 4: Not listening back to my calls

The fourth mistake I made was not listening back to my calls. I wish I had done this earlier in my first year of sales because I ended up rolling out this sort of feedback approach when I started managing sales reps. I’ve consistently found that one of the easiest and fastest ways to get better at sales is to simply record your calls. By recording your calls, you quickly pick up on the phrases that you say all too often that might not necessarily land with your prospect as well as the pickup on the gaps that might be happening in your product demos.

Now it’s important to note that states have different recording laws, so make sure you abide by those. And apps like Zoom have actually started to make it easier to make it clear to the participants in the meeting when the call is being recorded. Overall, if I were to give advice to a first year sales rep, I would tell them to record at least one call every single week, and then spend some time to playback that call in VLC player at one and a half to two times speed. VLC player is a free app for both Windows and Mac, and it allows you to playback faster than normal speed that way you can actually listen to more of your sales call in the time that you would have spent just listening to one.

As you listen back at all of your recordings, I want you to think about what is the one thing I did really well in this call and what is one thing that I wish I had done a little bit better. Then from there, the next time you do a call, I want you to think back on that strength and that weakness and double down in getting better at that weakness as well as getting even better at that strength that you highlighted.

Mistake 5: Not journaling my learnings

In terms of the last mistake I’ll share for today in my first year of sales, I think that that comes down to not journaling my learnings along the way. This is something that I wish I had done in my first year of sales because it would’ve given me a launchpad for my second year of sales of having clear goals and outcomes that I wanted to achieve.

It wasn’t necessarily a huge drawback for me, but it would have been helpful for me because then later on, when I became a sales leader and manager, I would have known exactly what my first year sales reps were going through because I had previously gone through those and documented the sorts of trials and tribulations that would have been helpful for me to incorporate into my onboarding resources for them.

Because I didn’t do this, the only way that I really can reflect back on my first year of sales now is through my memory as well as the six and 12-month feedback cycles that my company had for me at that time. So in the case where you are starting, or you want to start a long sales career, my biggest piece of advice would be to be intentional in how you document your journey. That way you can continue to grow and also impact others that you might meet in your journey.

Big takeaways

There are two things that I want you to remember from today’s article:

  1. The first takeaway is listen to your prospect and learn to shut up. Seriously, by talking less, you will end up selling more. Trust me on this one.
  2. The second thing I want you to remember is that whenever you’re looking up a website on Similarweb, make sure that you are looking at the traffic sources. Look at where people are getting their traffic so that you can then reverse engineer specifically the growth strategies that they might be using in order to get more traffic and more customers.

If you liked this article, be sure to check out my YouTube channel to get new videos every single week. I’ll help take you from zero to self-starter as you grow your business, get more customers, and hone your business acumen. Also, feel free to share this with anybody that you think might benefit from the mistakes that I made in sales and avoid making the same mistakes.