39 Essential Questions to Ask Before Accepting Your Next Sales Job
As a top-performing sales professional, you know that success in this field requires more than just a knack for persuasion and a driven personality. Thriving in sales means working for the right company, selling the right product, and operating within the right culture and environment to support your efforts.
So when it comes time to make a career move, you can‘t afford to just jump at the first exciting opportunity that comes along. Choosing the wrong sales job can stall your career momentum, torpedo your earnings, and leave you feeling frustrated, burnt out and demoralized.
In fact, a recent survey by sales strategist Marc Wayshak found that a whopping 61% of salespeople are actively looking for a new job at any given time. The top reasons cited? No room for advancement, low pay, and a lack of belief in the product. All factors that could have been uncovered during the interview process with the right line of questioning.
The lesson? You need to approach the job search as strategically and methodically as you do a complex sales deal. This starts with the job interview, where it‘s critical to engage in a two-way exploratory dialogue, not a one-sided interrogation.
Yes, the hiring manager will grill you with questions to gauge your sales acumen and culture fit. But it‘s equally important for you to drill down into the key aspects of the role and get a true picture of the opportunity. Only by asking the right questions can you determine if the grass will really be greener or if you‘re better off staying put.
With that in mind, here are 39 vital questions to ask, grouped into five key categories, before accepting any sales job offer:
Company Performance & Growth Potential
First and foremost, you‘ll want to understand the overall health, direction and upside potential of the business. Some key indicators to probe into include:
- How is the company performing this year in terms of revenue and growth?
- How is the sales organization tracking to plan?
- Which products, divisions or market segments are leading or lagging?
- What is the company‘s competitive win rate and positioning?
- What are the major growth levers and initiatives for the next 1-3 years?
The goal here is to gauge momentum and opportunity. Ideally, you want to join a rocket ship, not a sinking vessel. A company that is on a clear growth trajectory, taking market share, and well-positioned for the future.
For example, if the business is flat or down versus last year, dig into why. Is it a execution issue or are there larger headwinds in the market? If certain products are underperforming, try to uncover if it‘s a temporary lull or a sign of deeper issues with the offering.
On the flip side, if the company is killing it, look for evidence that the growth is sustainable. Press for specifics on where revenue is coming from and the investments being made to drive continued expansion. The more you can link the company‘s upside to your earning potential, the better.
Sales Team Culture & Collaboration
You also want to get a sense of the overall sales environment you‘ll be walking into. As the saying goes, culture eats strategy for breakfast. Some questions to ask include:
- How would you describe the sales culture?
- What are the common traits and skills of top performers here?
- What types of people tend to struggle or not mesh well?
- How collaborative vs. competitive is the team?
- How tenured are most reps and sales leaders?
- What is the approach to sales coaching, training and mentoring?
- How are territories and accounts assigned?
- What does a typical month look like in terms of activity and cadence?
The answers you hear can speak volumes about what your day-to-day experience will be like. You‘re looking for signs of a positive, energizing, team-oriented environment, not a pressure-cooker or shark tank.
Pay attention to turnover rates and average rep tenure. While some churn is normal in sales, an exodus of talent can be a major red flag. According to a study by The Bridge Group, average rep turnover in B2B sales is 34%. If the number you hear is much higher than that, dig into the root causes. It could signal issues with how the team is managed, comp plans, product quality, or broader culture challenges.
Also listen for how performance is evaluated and rewarded. Is it a you-eat-what-you-kill environment or are there mechanisms to promote team selling? How are top performers recognized? A Gallup survey found that companies with highly engaged teams have 21% greater profitability. Probe to understand how the organization creates energy and shared purpose.
Sales Process & Enablement
To hit the ground running and crush your number, you need a strong sales methodology and the right enablement resources at your fingertips. Questions to pressure-test the sales engine include:
- Can you walk me through the sales process from start to finish?
- What are the key stages and typical sales cycle length?
- What percentage of leads come from marketing vs. outbound efforts?
- How many accounts does a typical rep manage at any given time?
- What tools and technologies does the team leverage?
- Are reps provided with effective scripts, decks, collateral?
- How are customer insights captured and leveraged?
- Is there a sales playbook or set of best practices to follow?
The responses you get should paint a picture of sophistication and strategic thinking, not seat-of-the-pants execution. Top companies arm their salespeople with a clear process, proven messaging, and packaged insights to boost efficiency and effectiveness.
For instance, research from Vantage Point found that firms with a defined sales process see 18% more revenue growth versus those that don‘t. And companies that follow a well-defined methodology are 33% more likely to have reps who achieve quota.
So if the sales leader struggles to clearly articulate the process and supporting tools, or worse, admits that reps just "do their own thing", consider it a warning sign. Lack of standardization can lead to inconsistency and wild swings in performance. It can also make ramping and reaching productivity much more difficult.
Compensation & Career Pathing
Next, get into the nitty-gritty on total earnings potential, not just base salary, as well as longer-term career advancement opportunities. Some questions to broach:
- What is the on-target earnings (OTE) for this role?
- How is the variable compensation structured?
- Historically, what percentage of reps hit quota?
- What do the top 10-20% of reps earn?
- How often is the comp plan changed or adjusted?
- Outside of pay, how else are reps rewarded and recognized?
- What does the career path look like for successful reps?
- How many reps are promoted per year and into what types of roles?
- Do you primarily promote from within or hire externally for sales leadership?
The key here is to determine not just starting pay, but realistic upside and growth trajectory. According to data from the Bureau of Labor Statistics, the median annual wage for all sales roles is $31,500. But top earners can clear well into the six-figures. Where will this position likely fall on that spectrum based on historical performance?
Also consider the stability and predictability of the comp plan. A survey by CSO Insights found that 81% of companies change their sales compensation plans every year. Too much tinkering can make it difficult to gain traction and forecast your income.
Finally, think about your long game. If you crush your number, what‘s next? Look for a company that values promoting from within and offers a variety of attractive paths forward. Great sales organizations are always grooming the next generation of leaders.
Potential Challenges & Roadblocks
Finally, probe to uncover any major hurdles or headwinds that could hamper your success. Remember, no job is perfect. By surfacing issues early, you can make an eyes-wide-open decision. Questions to pose:
- What are the biggest challenges facing the sales team currently?
- What internal or external roadblocks come up most often?
- If you could wave a magic wand, what would you change tomorrow?
- What are your top priorities for the sales organization this year?
By inviting the interviewer to step back and get real about areas for improvement, you may unlock valuable insights. Perhaps the product needs work or the team is understaffed. Maybe there‘s friction with another department or disappointing customer churn.
Whatever comes up, consider how it could impact your ability to perform. Then probe further to understand what‘s being done to address it. Strong, transparent leaders will have a plan and a path forward. Weak ones may try to downplay problems or pass the buck.
As you can see, there‘s no shortage of questions to ask in a sales job interview. By drilling down into these five areas – company growth, culture, process, compensation, and challenges – you‘ll turn over the rocks and kick the tires to make sure the opportunity is truly right for you.
Remember, the best questions will be specific to the role and your situation. So use this as a guide, not a script. And augment your learnings by doing independent research and tapping your network for intel. The more data points you gather, the clearer the picture will become.
Lastly, listen to your gut. If something feels off – an evasive answer, an overly rosy claim, a lack of enthusiasm – dig deeper. Choosing your next sales job is a major decision with big implications. Take your time and trust your instincts.
With the right approach, you‘ll gain the clarity and conviction to make a great choice. One that positions you for success, maximizes your earning potential, and keeps your sales career on an exciting upward trajectory.
