Not long ago, I spoke with a university graduate who'd landed an account executive role at a giant company right out of school. Given how rare it is for an entry-level salesperson to skip the development (lead generation) role, you can imagine my surprise.

Even so, I knew she was doomed. And predictably, she didn't last six months.

Yes, she'd diligently researched both the company and the position, and compared it to other offers she had received. But when it was her turn to ask a few questions during the interview, she--like the majority of new salespeople--failed to ask the critical questions that would have written "avoid" all over the walls of her future cubicle. 

I'm talking about the kinds of questions that challenge management, so they can't hide behind fancy marketing speak or gaps in their knowledge. The interview should be a chance for you to uncover what daily life as a salesperson is like at the company. The best professionals know that asking the right questions can mean the difference between a fulfilling, productive sales job and one that feels tantamount to a prison sentence. 

In the case of this woman, not asking the right questions meant she had more than a few surprises once she started the job, impossible quotas and slow pay cycles among them.

So before you suit up and head to your next interview, be sure you're prepared to ask the following questions: 

1. What percentage of staff hit quota last quarter and last year?

A job advertisement can attract anyone if it vaguely promises a six-figure salary, but that number doesn't mean anything if a good percentage of people don't hit the associated quota.

You might be the best salesperson in the world, but it's still going to take time to learn the landscape of your new company well enough to earn or out-earn the top performers.

So this question is critical to determine the likelihood of how fast that happens and how likely you are to actually reach those six figures in the mentioned in the job posting. 

If the person interviewing you can't give a straight answer, watch out. When a friend of mine asked this question in an interview, the Vice President responded that attainment was poor because the company's salespeople were terrible and management was weeding them out. That's a glaring red flag.

Great organizations will have between 70 and 80 percent of reps consistently hitting quota; good teams will have 60 to 70 percent, and the average is 50 percent. Hopefully, they'll also have stories of people who exceed their quota, too. If they don't mention any of this, proceed with caution.

2. Can you walk me through your funnel math?

So you discover everyone at this company hits quota. Fine, but how hard do they have to work to do it?

Asking this question should inspire management to walk you through exactly what you must do to reach quota, basing these steps on the sales team's past performance and a well-thought-out sales funnel. And it should come down to basic math.

You should know roughly how many leads you'll need to generate and convert every month to hit your goals.

If the Vice President can't walk you through the numbers at each stage, you should be skeptical of the position. Having to bring in 40 new opportunities a month instead of four makes a big difference when it comes to hitting your goals, not to mention managing your stress levels and productivity.

3. When do I get my first commission check?

You'd be appalled at how often companies fail to pay their salespeople within a reasonable timeframe.

Some organizations don't pay salespeople for a deal they closed until the customer has fully paid, their check has cleared the accounting cycle, and the customer has started using the product. Since customers often buy business-to-business products well in advance of use, you could be waiting months for a commission check.

It's great to hit your quota in your very first quarter, but that doesn't mean much if you don't see the money until the end of the year. World-class sales organizations will pay out every month for the previous month's closes. Why? Because a system like that incentivizes people to close. 

If the idea of asking these questions intimidates you, practice on a friend before the interview. It's better to ask and have someone refuse to provide answers than to be tricked into a lousy sales job. There are amazing opportunities everywhere for salespeople. It's worth going through a few extra interviews to get to them.