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My Tips for Starting a Career in Sales


I recently had the pleasure of addressing a bright group of aspiring sales professionals while visiting UMass Amherst.

The conversation and their questions inspired me to want to share a little of what we discussed.

Whether you are just starting out in sales or you have been in business for a while, it is always good to be part of an engaging dialogue about trends, statistics and tips that impact the role you are in, or aspire to have one day.

Sales Stats, and Why It’s Important to Follow-Up:

  • 48% of sales people never follow up with a prospect.
  • 25% of sales people make a second contact, and stop.
  • 12% of sales people only make three contacts, and stop.
  • Only 10% of sales people make more than three contacts.
  • 2% of sales are made on the first contact.
  • 3% of sales are made on the second contact.
  • 5% of sales are made on the third contact.
  • 10% of sales are made on the fourth contact.
  • 80% of sales are made on the fifth to twelfth contact.

Source: grantcardone.com

People underestimate how much follow-up is needed in order to be successful, especially in sales. In the fast-paced, oversaturated and overstimulated world we live in, just because someone doesn’t get back to you the first time (or the second time or the third time) doesn’t mean they will not eventually buy from you or need your services.

In sales, it’s important to be motivated by the long-term relationship, rather than by any short-sighted, transactional sell.

Which is why the most successful people in sales are authentic, persistent and deliberate. They build success on relationships, and make genuine and consistent connections.

Tip no.1 – Grow your network by one person every day.

What You Should Know About a Career in Sales

It is the most challenging, and rewarding career you may ever have.

Sales is hard, and requires hard work. But, most people love to buy and they especially love to buy from people they like. Relationships are key to this.

Relationships are also key to leading someone through the sales funnel – and activity almost always makes up for a lack of skill. So, don’t worry if you don’t come with years of esteemed experience. As long as you are genuine and making the calls and getting the meetings, the sale will follow – no matter what it is you are actually selling.

One aspect of sales that nobody ever talks about are the challenges. Everyone always talks about the upside of sales and how much earning potential there is, which of course is true – the sky is the limit you’re willing to travel to in my office – but it’s important to recognize the adverse reality that is sales.

The numbers I shared tell a story, and that is that persistence leads to success, but also that rejection is constant. It’s important to build up a tolerance and to not take ‘no’ personally. I like to tell my team that you can’t have a glass jaw in this job.

Tip no.2 – Prepare for objections so you can proactively address them head on.

The Science of Selling

Numbers do not lie, which is why in sales, the most successful people follow key metrics and their performance is constantly measured.

By the way, every job has metrics associated with it. In sales, we embrace them and are always trying to exceed them. But if the thrill of being measured against your own best self, your peers and your competitors is not something you enjoy or take pride in, sales might not be the best career for you.

Tip no.3 – Stay hungry.

Another key measurement in sales is information.

Information is power, no matter what you do, but in sales information directly correlates to success. It means knowing your customer, researching their business and providing value that can only be delivered when there is knowledge.

Knowledge also means having a plan.

Tip no.4 – Know your plan, and work your plan.

More often than not, people come up with great ideas, but do not execute on them. That’s because they didn’t have a plan and an idea not executed is just a dream.

Don’t be a dreamer, be a doer.

Perfecting the Art of Selling

I’m going to give away the secret sauce: the art of selling is your likability.

People do business with people they like and who they feel they can trust. Period.

If you can find common interests with the people you do business with and make the relationship personal when possible, you will be successful.

Tip no.5 – Always be working on your people skills. You’ll need them wherever you go.

Read, Network and Never Stop Learning

There are a lot of great quotes out there about the importance of networking – especially if you’re in sales – but here’s what I’ll say about it: if you network, you’ll never have to do any “hard prospecting” or look for work another day in your life.

Networking ties into a few of the principles I’ve shared about a career in sales. Namely, that you should always be building new connections, you should make those connections genuine and personal when possible and you should always be working on your people skills.

Networking does it all.

Be your best by surrounding yourself with the best. Build a network full of great coaches and mentors, business connections, colleagues, people who share your interests and causes you’re passionate about – just build it. And keep on building it.

Tip no.6 – Never stop learning, from the people you meet to the books you read.

My recommended reads for people interested in sales include, but are not limited to:

  • “How to Win Friends and Influence People” by Dale Carnegie
  • “How to Swim with the Sharks without Getting Eaten” by Harvey McKay
  • “Think and Grow Rich” by Napoleon Hills


Lastly, I wanted to share a great question I got asked last week from one of the students in the sales club presentation I gave:

“One of my goals is to have a career where I wake up every day and enjoy going into work. You know the saying ‘If you love your job, you never work a day in your life’ – this is something I am really striving to find. I have an entrepreneurial mindset and right now I think that doing sales in an entrepreneurial environment or with some type of new technology would make me extremely happy. However, I’ve received some advice from different salespeople that out of school it would be smart to work for a big company (Oracle, Salesforce, etc.) that can provide me with excellent sales training, and then move on from there. What do you think about this plan? Do you think it may be better jumping into a small startup to gain my experience hands on? I’d love to hear what you think.”

Here’s my response:

There are pros and cons to both, and it really depends on the fit and feel for you as a person. No doubt, Oracle or Salesforce would pop you into a well-oiled machine, with state-of-the-art training, and a household brand behind you. On the flip side, a smaller firm affords you the opportunity to build something, and get those entrepreneurial juices flowing. I also tend to believe people learn at an exponential pace in a start-up environment because of the myriad of tasks mixed with opportunity that are constant and evolving. That said, it takes a lot of hard work and perseverance to grow a small firm. It really comes down to fit, and how it feels to you.

What are your questions about a career in sales? Comment below, or email me: darrin@labur.com.