Avoiding Buyer’s Remorse: Six Questions to Ask

Congratulations! You landed that job you really wanted: you rocked the interviews, edged out the competition, and negotiated a great salary. You’re excited to say “yes” and for good reason. 

That initial excitement is normal, but it can also blind us from seeing important red flags. As anybody who has lived it knows: the only thing worse than being stuck in a job you’re dissatisfied with is the disappointment of getting settled into your new job… only to realize it wasn’t the “fit” you thought it was going to be.

The good news is that it doesn’t have to be a game of workplace Russian roulette. Avoid buyer’s remorse at your new job by asking yourself these six questions before you sign on the dotted line and put in your two weeks notice:

  1. Have you had a conversation with a peer who will be on your team? Often times during the interview process candidates will speak with some combination of HR, managers, and a hiring committee. Speaking with a peer is a unique opportunity outside formal interview channels to get a better understanding of the day-to-day of the job, team culture, and organizational dynamics. These conversations should make you feel more confident about your decision and are also critical opportunities to spot red flags. Most organizations should be amenable to facilitating a peer conversation for you as part of your consideration of their offer. In fact, if they’re not, put that in the “red flags” column immediately.

  2. Do you understand how professional development and career advancement are structured? It’s easy during the interview and negotiation phase to be focused on your incoming role and salary. Hopefully your new organization is a place where you’ll grow, which is why it’s equally important to understand how professional development, raises, and promotions are handled. I’ve worked in organizations that are fiercely meritocratic and quick to reward top performers with raises and promotions. I also worked at an organization that didn’t have regular performance reviews. That type of variation makes for vastly different experiences, which is why it’s essential to understand where your new organization stands.

  3. If you’re in a role that includes travel, what’s the organization’s travel policy? Somebody recently told me about a company they worked at where they couldn’t travel for business during business hours. They had to first stay in the office all day and travel to client meetings in other cities after hours, either at night or early in the morning. As you can imagine, that person is no longer with that company. That travel policy isn’t just unreasonable, it clearly signals a broader lack of respect for employees and their time. On the flip side, many companies have more supportive travel policies that signal just the opposite to their road warriors. It was a small gesture but one of my former employers offered a slightly-above-average per diem when we were on the road (which was frequently). For the amount we were working and traveling, it set a tone about our responsibility to be stewards to one another: a sentiment confirmed year after year in our annual engagement survey results.

  4. If you’re a bonus-eligible employee, what does your bonus potential actually look like? How is your bonus going to be structured and evaluated? How did people perform against their bonus potential last quarter/half/year? Those are critical things to understand and it’s completely reasonable to ask about performance trends over time. I had a friend who felt “burned” when the company wooed them with numbers from a single exceptional quarter, only to discover it was an anomaly—and everyone knew it. On the flip side, I once had an executive take out a spreadsheet and (without identifying team members) walk me through how many members of the team achieved various ranges of their bonus potential. Lastly, I also like the approach my client recently took when evaluating two competing offers for a new sales job: as anybody who has ever signed a bonus or commission plan knows, there are usually pages upon pages of fine print. That “devil is in the details” mindset is exactly why she requested sample commission plans from the two companies—both of whom provided paperwork without hesitation. 

  5. Do you understand the full benefits package and how it impacts your compensation? One of the biggest surprises I see people encounter is getting into a new job and learning that their health insurance is going to cost significantly more. That’s an avoidable surprise that should be part of your decision and salary calculus. Do ask to see the full benefits package and, when you do, you may even be pleasantly surprised: it wasn’t until I received the full benefits overview at my current role that I learned how much money I’d be saving a month with their generous commuter benefit (literally almost $1,000/year). This is also where you’ll learn important information about parental leave, vacation time, telework, education benefits, 401K matching and the other benefits that matter most to you.  Lastly, also be thoughtful when evaluating equity or stock options if you are working for a company that offers them. Like bonuses in tip #4, the devil is in the details. In this case, it’s your share price, discount, vesting period and exit options that make all the difference. 

  6. Is there a non-compete or other important documentation you need to sign? Many years ago I was handed a non-compete over a week after signing an offer letter and putting in my notice. It wasn’t the non-compete that threw me for a loop, but the after-the-fact timing. The time to review a non-compete, ask questions, or negotiate is before accepting your offer. That’s why I recommend you proactively confirm if there’s any outstanding paperwork to review before formally accepting any offer.

This might feel like a long list of things that can go wrong when it's actually a list of things that should go right. So don’t feel discouraged, feel empowered: if you and the organization have been doing your job right throughout the process you’ve probably covered most of the above checklist questions during the interview process. If you’ve missed something, well, that’s exactly why I put together a checklist: let’s make sure your big new gig doesn’t come with any big (unpleasant) surprises.


Randi Braun is a career coach living in Washington, DC and the Founder of Something Major. Discover more below on Instagram or www.SomethingMajorCoaching.com. (c) Randi Braun 2019