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How to Succeed in Sales: 5 Things I Wish Someone Told Me When I Was Starting Out

Let me guess. You started your career in sales because someone said you’d be good at it.

You’re outgoing and competitive, so you should be great at sales… Right?

While these are both excellent traits for salespeople to have, there’s a lot more to it if you want to succeed in sales.

If I had someone tell me this when I started my career in sales, I would have avoided a lot of unnecessary stress and self-doubt.

So, today, I’m doing just that and sharing five things I wish someone had told me when I first got started, so you can get started on the right track and succeed in sales long term.

#1 New Doesn’t Mean Unskilled

When you start something new, it’s easy to think of yourself as unskilled. But don’t be so quick to shortchange yourself.

You have a background of experiences that uniquely qualify you for this role. Maybe you played high school or college sports. That means you learned how to be part of a team. You learned that changing your technique is awkward at first, and you may even regress before you get better. You learned how critical it is to master fundamentals. These are all transferable skills.

Proudly claim what you’ve acquired throughout your life. And instead of thinking of yourself as unskilled, think of yourself as unproven.

In time, you’ll find you know more than you think.

#2 Avoid Comparisons

Like I mentioned above, chances are you’re a competitive person. You’re fueled by being number one. You might even consider competition as a Strength of yours.

But while comparison is a great motivator in stack ranking, it becomes a de-motivator in the nuances of how you sell. This is because, while there are core fundamentals to selling, the ultimate key to success lies in being authentic.

Authenticity means you make it yours. If you ask a discovery question and it feels awkward rolling off your tongue, take note of that. Explore how you can achieve the same purpose of that question but in a way that feels natural to you.

Comparing yourself to other salespeople early on will only lead you away from your authentic self. It will lead you to copy others and that simply won’t work in the long run.

If you’re struggling with it, talk to the best performers on your team, find out what their secret sauce is, and see how you can adapt it to your unique personality and style.

The key is to invest time in finding your secret formula for success. As a new sales rep, your job is to learn sales fundamentals, the methodology your company uses, and what your authentic self looks like.

Take the best of what others are doing, find your authentic voice within the sales methodology, and lean into the awesomeness that is YOU.

#3 Ask for Help

There are two traps I see new reps fall into when it comes to asking for help.

Not asking for help

New reps often fear they’ll look like they don’t know what they’re doing. This was my biggest hurdle hands down, and it took me much longer than I want to admit to ask for help.

What helped me get over this was asking myself the following questions:

Should I even be the person who knows that? 

For example, a super technical question from a prospect.

What is the cost of not asking someone? 

Time is money in sales. How much does it cost you to spend an hour figuring out an answer on your own rather than taking 5 minutes to ask someone?

Have I asked this question before?

Be mindful of this. If you find yourself asking the same question multiple times, consider a better method of retaining information. I write things down to help cement them in my brain and have something to reference quickly.

If you’re still reluctant, use the “Check 3 before Me” strategy. Check 3 resources before asking someone for help. (ex. Slack channels, sharepoint site, or a buddy.)

Asking the wrong person

If you get assigned a buddy or if you have a teammate they really like, this person can become your go-to-person for ALL questions.

And while I’m a big fan of the buddy system for new hires, a new rep should be building additional relationships. If you’re at a bigger company, take time to get to know your solution engineers, sales enablement team, and account managers.

When you have a question, ask yourself, “Who is the best person to answer this?” If you can’t answer that question, then ask your buddy.

The key is to seek out the expert on the topic rather than defaulting to the person you’re most comfortable with.

#4 Learn Your Motivators 

Most people assume the number one motivator in sales is money. That seems like an inherent motivator for anyone. But the truth is, it’s rarely that simple.

In, The Dream Manager, Matthew Kelly uncovers how our dreams can be a strong motivator for how we work.

As a leader, I make a goal of getting to know my direct reports personally. This helps me understand what their dreams are. Then, I can maximize their production in a way that fulfills them personally.

Don’t wait for your manager to take this approach. You can do this exercise on your own.

Ask yourself, what do I dream about?

Maybe it’s a big trip, buy a house, or pay off student loans. Now, tie these dreams to your goals as a sales rep.

How much do you need to make to do this?

How many deals will it take?

How much pipeline do you need to achieve that goal?

At the core, money is not the motivator. It’s simply a means to achieving your dreams. This may seem like a small change, but knowing what your true motivator will help you stay excited and motivated even in down periods when you’re struggling to make quota.

#5 Tune in to How You Feel

Here’s the honest truth — not everyone who starts in sales will want to stay in sales as they progress in their career.

That’s okay.

There are other ways to grow your career in sales besides moving up the corporate ladder into management.

If this sounds like you, you can identify your next step by asking yourself:

  1. What drains you?
  2. What energizes you?
  3. When you’re at your best, what are you doing?
  4. When you’re happiest, what are you doing?

As you answer these questions, look for recurring themes. Typically, the next step for you lies in those answers.

Most people struggle to answer these at first. If that’s you, take a few weeks to track interactions that make you happy, energized, or drained.

What are you doing? Who is involved? Is there anything else that might have elicited positive or negative feelings?

After a few weeks, look at your notes and look for themes in your answers. Chances are you’ll be able to quickly answer the questions above.

Start Your Career Right

Sales can be a rewarding, satisfying career. The key to succeeding in sales lies in finding your unique voice, knowing if sales is for you (or not), and defining a career path that is right for you.

If you’re new or struggling, take control of your success. Someone might have told you that you’d be good at sales, and they were probably right. But your success and happiness in sales won’t necessarily be that automatic.

Like anything else, a little bit of intention and focus can set you on fire.

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