Sales can be one of the most rewarding career paths—both financially and personally. In fact, I spent most of my career in sales. The best salespeople can often earn more than their managers, enjoy flexible schedules, and develop skills that transfer to any industry. But not all sales positions are created equal, and the wrong opportunity can leave you stressed, broke, and questioning your career choices.
Recently, one of my godsons told me he was leaving his hourly job for a sales position. The reason he was leaving was because of the potential increase in take home pay. I was a bit surprised since he’d never expressed an interest in sales before. He’s a young adult and fully capable of making his own decisions. However, since he’s my godson and, you know, I love him, I had a few questions about the job. For instance, what’s the pay structure? Is there a base salary or is it purely commission? Is the commission capped? Is there a draw against commission? Well, it turns out that the potential money he could make is what he had focused on during the presentation. But he at least knew that it was door to door sales. Unfortunately, that’s not enough information to make an educated decision about leaving one job to go to another. In fact, it’s not enough information to accept any job unless you’re really desperate.
Here’s the thing, whether you’re considering your first sales role or evaluating a new opportunity, asking the right questions upfront can save you months of frustration and set you up for success. Here’s your complete guide to assessing whether a sales position aligns with your goals and circumstances.
Understanding the Compensation Structure
“How exactly will I be paid?”
This is the most critical question you can ask. Sales compensation varies dramatically, and understanding the structure upfront prevents nasty surprises later.
Follow-up questions to ask:
- Is this straight commission, base salary plus commission, or salary only?
- If there’s a draw against commission, is it recoverable or non-recoverable?
- What’s the average earnings of someone in this role after one year?
- How often are commissions paid out?
- Are there any caps on earnings?
- What happens to my commissions if I leave the company?
- Why is this position open at the moment?
“What are the quotas and how realistic are they?”
Every sales role has targets. Make sure they’re achievable based on the company’s track record, not just wishful thinking.
Questions to explore:
- What percentage of the sales team hit their quotas last year?
- What’s the average time it takes for new hires to reach quota?
- How are quotas determined and how often do they change?
- What support do you provide to help salespeople hit their numbers?
Evaluating the Product and Market
“What exactly am I selling and to whom?”
You need to believe in what you’re selling. If you can’t get excited about the product or service, your prospects won’t either.
Dig deeper with:
- Who is the target customer and what problem does this solve for them?
- What’s the typical sales cycle length?
- How does this product compare to competitors?
- What’s the price point and how price-sensitive are customers?
- Are there any legal or regulatory issues I should know about?
“How do you generate leads?”
Some companies provide warm leads; others expect you to find your own customers. Know what you’re getting into.
Important follow-ups:
- Will I be cold calling, or do you provide qualified leads?
- What marketing support exists to generate interest?
- Am I expected to prospect entirely on my own?
- What tools and resources are available for lead generation?
- What sales tools will I receive?
Understanding Training and Support
“What does training look like?”
Great sales organizations invest heavily in training their people. Poor ones throw you to the wolves.
Key areas to explore:
- How long is the initial training program?
- Will I have ongoing coaching and development?
- Is there product training as well as sales skills training?
- Who will be my direct manager and what’s their background?
- What happens if I’m struggling to meet expectations?
Assessing Company Culture and Stability
“What does career advancement look like here?”
You want to know there’s a path forward, not just a dead-end job.
Questions to ask:
- Can you show me examples of people who’ve been promoted from this role?
- What skills or achievements typically lead to advancement?
- How stable is the company financially?
- What’s the turnover rate in this position?
- Why is this position open?
“What’s the team dynamic like?”
Sales can be competitive, but toxic environments hurt everyone’s performance.
Explore with:
- How collaborative versus competitive is the culture?
- How does management communicate with the team?
- What happens when someone is having a bad month?
- Can I speak with someone currently in this role?
Red Flags to Watch For
Be cautious if you encounter any of these warning signs:
- Vague answers about compensation: If they can’t clearly explain how you’ll be paid, walk away
- Unrealistic promises: “Everyone makes six figures in their first year” is usually too good to be true
- High-pressure tactics in the interview: If they’re pressuring you to decide immediately, it’s often because they know you’ll change your mind if you think about it
- No successful examples: They can’t point to current employees who are thriving in the role
- Excessive focus on motivation over skills: While attitude matters, good companies also provide systems and training
Questions About Work-Life Balance
“What does a typical day/week look like?”
Sales schedules can vary wildly. Make sure the expectations align with your lifestyle.
Consider asking:
- What are the expected work hours?
- Is weekend or evening work required?
- How much travel is involved?
- Ho much do you pay for mileage?
- Do you provide a vehicle or do we use our own?
- What’s the policy on working from home?
- How much administrative work versus actual selling?
Making Your Decision
After gathering all this information, reflect on these key factors:
Financial viability: Can you survive the ramp-up period? Do the earnings potential justify the risk?
Skill development: Will this role teach you valuable, transferable skills?
Company trajectory: Is this organization growing or struggling?
Personal fit: Does the product, industry, and culture align with your interests and values?
Remember, sales roles often come with more risk than traditional jobs, but also more reward potential. The key is making sure you’re taking a calculated risk based on solid information, not a blind leap based on promises.
So, did my godson take the job. Well, it turns out that he did. His best friend decided to leave his job and hop on the sales wagon as well. But unfortunately, the job wasn’t all it had promised to be. For the two of them, it was a lesson learned. It’s also part of life. I’ve been there. However, now, he’s equipped to ask better questions when considering the next opportunity.
One last note: Whatever your pay structure is in a sales position, your compensation will vary from week to week, month to month, and year to year. Make sure account for that. Just because you had a great week this week doesn’t mean you’ll make the same next week. A sales position with a good base salary helps to offset some of those swings. However, the mistake many salespeople make is that they spend as if the money will be the same very paycheck. If you make a base salary that allows you to live decently, try saving your bonuses or commissions. Living below your means and saving the rest is a great way to build wealth.
Sales Compensation Glossary
Base Salary: Fixed amount you’re paid regardless of sales performance. Provides income stability but may be lower than commission-only roles.
Commission: Percentage of sales revenue you earn on top of (or instead of) base salary. Usually ranges from 2-20% depending on the industry and product price.
Draw Against Commission: Advance payment against future commissions. Think of it as a loan from your employer that gets deducted from your earned commissions.
Recoverable Draw: If you don’t earn enough commission to cover the draw, you owe the company money back when you leave.
Non-Recoverable Draw: Company can’t ask for the money back if you don’t earn enough commission to cover it. Much safer for employees.
Quota: Sales target you’re expected to hit within a specific timeframe (usually monthly or quarterly).
Sales Cycle: Average time from first customer contact to closing the deal. Can range from days (simple products) to years (complex B2B sales).
Territory: Geographic area or type of customers assigned to you exclusively.
Residual Commission: Ongoing commission payments for recurring customers (like subscriptions or service contracts).
Commission Cap: Maximum amount of commission you can earn, regardless of how much you sell. Avoid these when possible.
OTE (On-Target Earnings): What you should earn if you hit 100% of quota, including base salary and expected commission.
Remember: The best salespeople ask tough questions and do their homework. If a company gets defensive about these questions, that tells you everything you need to know. The right opportunity will welcome your thorough evaluation—they want people who are serious about success.
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