What Interviewing 31 Sales People Taught Me About “Sales”

sales person

Over the past few months, I have interviewed 31 potential hires for a sales position. I’ve posted openings on job boards, used recruiters and even tapped into my network. The one thing I quickly realized is that it’s really, really hard to find the right sales person.

Although I haven’t found the perfect fit yet, luckily interviewing 31 people hasn’t been a complete waste of time since I learned much more about “sales” than I did before. Here are some of the “ah-ha” moments I had over the last few months:

You can’t hire without testing the waters

If you want to grow your sales, what’s the first thing you would want to do? Hire a sales person, right? It sounds like the logical thing to do, but it isn’t.

You won’t know what problems the sales person is going to run into unless you try being one yourself. So, before you try to hire someone to sell for you, make sure you do it for a few weeks, if not a few months. It’s not easy to teach someone to sell something if you can’t even do it yourself. Even if you’re not the greatest sales person in the world, you need to spend time training your new hire on the particulars of the job.

Also, from a compensation perspective, you can get an idea of how much each sale will be worth to the company and how many deals a sales person can potentially bring in each quarter.

Not all departments are equal

When you are selling a product or service to a company, you have to pick a department to sell to. Whether it’s marketing, customer service, sales, or engineering, you have to pick a department to tackle.

If you are trying to sell to multiple departments, your sales cycle can become a lot longer. The easiest department to sell to within an organization is usually sales. It doesn’t matter what budgets other departments have – sales makes money for a company. Other departments, like marketing, cost companies money.

For example, if a sales person tells her boss that she needs a specific piece of software to make more sales, her boss is likely to say yes. If a marketing person needs software to make better marketing decisions, her boss is likely to ask if it is in the company’s marketing budget.

Look at Salesforce as an example. The company sells its software to your sales people to help them track and manage their clients so they can make more sales. Plus, it allows your boss to keep tabs on you if you are the sales person.

You need a process

Having a sales person or two is great, but it won’t make your company successful. You will need to scale your sales department and have different groups focusing on different aspects of sales. For example, your company may end up having enterprise, inside sales, account management, and lead generation teams.

Having different groups focus on different things is a great way to scale your sales. But, you won’t be able to do this unless you come up with a process.

From having materials to train new employees quickly to creating a list of FAQs asked by customers, you need to put the time and energy into creating processes for your sales team. If you don’t, you’ll end up having a lot of sales people who aren’t meeting their quota.

Pay doesn’t matter

I don’t care if a sales person wants $50,000 or $250,000 a year. Although you may think that you are getting a better sales person if you pay more, it isn’t always the case.

Some people love selling no matter what you give them or pay them. And some people just like sitting around even if you incentivize them to sell more by giving higher commissions.

You have to find candidates that are hungry, scrappy, and willing to do whatever it takes to make a sale. Pay is great and all, but you just have to find someone who has a passion for selling.

Numbers are deceiving

If you ever interview a sales candidate, he will tell you his quota, which is a number that he is supposed to hit each quarter or year in his current (or past) job. For example, if a sales person works for Oracle, his quota may be one million dollars per year in sales.

So, if you hired that person, you would expect him to do fairly well, right? Sadly, it doesn’t usually work that way.

Your new hires can paint a picture of how much money they brought in for the company they are currently working for, but to really figure out how many sales they did, you have to ask the following questions:

  1. How much of your quota was made up of new sales?
  2. How much of your quota was from renewals?
  3. How much of your quota was made up of up-sells?
  4. What was your average deal size?
  5. How long is your current sales cycle?
  6. Out of all the sales you closed, how many of those leads were given to you?

Asking those questions will help you determine how much money the candidate can potentially bring in if he is not given any leads and has to start selling on his own.

Selling is only half the battle

Just because someone is a good sales person doesn’t mean that this person is right for the job. There are two important aspects that you have to look at other than the person’s ability to sell:

  1. Does she fit within your company’s culture? – if she can’t get along with your team, you don’t want to hire her. As your sales grows, it will require support from other departments within your organization. And if the other departments hate sales, you won’t hit your numbers because they won’t get the support they need.
  2. Does she understand what you are selling? – if a sales person doesn’t get what your company is selling, how can she possibly sell it? Now, granted, she may get lucky and make a few sales, but she’ll be a lot better off if she understands what you are selling.

The best way you can figure those two things out is to have other members on your team interview the person as well as test her to see if she understands what your product or service does.

If you can’t find someone who fits within your company culture or understands what you are selling, you shouldn’t hire for the sake of hiring. Keep looking.

Pick a niche and go for it

When you first start selling your product or service, you need to pick an industry to sell to and just go for it. The industry can be whatever you want: health care, bio-tech, or even construction.

The industry you pick should be one that you think can benefit from your product or service and, more importantly, is one that you or your sales person has a strong Rolodex for.

Don’t spend much money on tackling that one industry; just hope that it works out. And if you don’t see it working out, make sure you quickly shift or refine your approach.

Once you tackle one industry and you have built up some marquee clients, you can go after others. If you decide to go after multiple industries at once, you will be more likely to fail as each one will bring its own set of problems.


Sales isn’t an easy thing to get good at. After interviewing 31 candidates and doing sales myself for years, by no means am I an expert in it. Heck, I would even say I am still a novice.

But one thing is for sure, when you are hiring for a sales position, make sure you hire slowly and fire fast because sales people are expensive. The last thing you want to be doing is spinning your wheels and wasting money.