How to Overcome Red Flags on Your Resume

Landing a job is never easy — but a resume full of red flags makes it even harder. What does it take to win over an interviewer if you’ve got employment gaps, short stints with multiple employers, or an unplanned departure on your resume?

As an HR executive that’s worked with companies ranging from multi-billion-dollar conglomerates to small, equity-backed ventures, I’ve led hiring for dozens of organizations and interviewed more than 3,000 candidates over the course of my career. I’ve seen many imperfect resumes, and I’ve seen how candidates can effectively position discrepancies or spotty job histories.

Ultimately, overcoming these red flags comes down to developing and controlling your own narrative. Red flags can — with good reason — call into question a candidate’s commitment, performance, and reliability. But by unapologetically owning your decisions and planning out concise, forthright talking points, you can proactively address these concerns and make the best possible impression on your interviewer. Below, I discuss three of the most common red flags I’ve encountered, and share some of the strategies I’ve found can be most effective for candidates looking to address these issues.

Employment Gaps

One of the most common resume red flags is an unexplained lengthy employment gap between previous roles. These gaps can sometimes lead hiring managers to assume that you have struggled to land jobs in the past, potentially indicating poor performance or some other shortcoming.

Of course, while an interviewer may assume the worst, there are in fact a number of perfectly valid reasons for a gap in employment. Interruptions in job history run the gamut from taking time off to care for yourself or a family member (including parental leaves), to education or reskilling, long-term unemployment due to a recession or other external factors, or a shift to a consulting or contractor role.

There are two ways to approach these gaps. First, if you’re not yet back on the job market, think about ways to fill your time with some sort of professionally relevant activity that you can later fit into a consistent narrative. For example, if your primary reason to take time off was to care for a family member, that doesn’t mean you can’t also complete a short online workshop or attend a weekly class at your local adult education center.

Similarly, even if you’re not working full time, consider adding some limited contractor or consulting work to beef up your resume. One of my executive coaching clients, Monica,* was facing a period of unemployment after leaving a high-profile marketing role. She felt burned out and knew that she needed time to recharge before making her next move — but she wanted to be able to demonstrate her skills whenever she was ready to embark on her job search, and she also knew it would be important to keep her network up to date. We strategized about how to allow her the time she needed while remaining professionally engaged, and ultimately, she set up an LLC and began doing light consulting work for friends and former colleagues. By the time she was ready to start her search, she had real-life examples of her work in her field — and she’d had time to rest and reconnect with her family.

Of course, in some cases, it may be difficult to take on additional side projects. In these situations, keep in mind the meaningful ways you’ve spent time between roles, and make sure you’re able to clearly articulate them. You may not have joined a formal program or pursued a degree, but did you volunteer? Take a class? Pursue a personal project? Find ways to demonstrate how whatever you spent your time doing does in fact reflect your strong candidacy.

In addition, if part of the reason you were unemployed for a little while is that you choose your roles carefully, emphasize that. Being selective demonstrates that you’re taking ownership over the job search process and that you’re not going to jump at any opportunity — you’re waiting for the right fit. The more you convey that an employment gap was (at least to some extent) your choice, the less likely your interviewer is to view you as desperate and unemployable.

One way to do this is to reference the specific attributes of the company and role that make it a particularly good fit for you. That might be skills or types experience listed in the job description that match with your unique background, or it could be the ways in which the job would offer opportunities you’re especially interested in, such as an industry change, a faster-paced environment, or the chance to work directly with customers. For example, this might sound something like:

“Since my last full-time role, I’ve had the opportunity to focus on developing my strategic acumen in a few different ways: I completed a Master’s level course on business strategy, and I also consulted with two early-stage companies on their strategic planning processes. Those experiences would be particularly valuable in the Finance role we’re discussing, where I’d play a major role in the planning and execution of the company’s strategy, including the establishment of financial metrics and dashboards to provide visibility on progress against strategic objectives.”

Job Hopping

The next red flag I’ve seen time and again is candidates who’ve had multiple jobs over a short period of time. This can raise a couple of concerns with interviewers: Will this candidate struggle to sustain a commitment to a single role or organization? Does this candidate have chronic performance issues? Either of these can make an employer wary about taking a chance on you, regardless of your qualifications. Especially for roles in which it can take six months or longer for an employee to fully ramp up in their new role, the employer may worry they’ll be short-changed if you end up leaving after a brief tenure.

Given these considerations, there are a few key strategies you can use to preempt your interviewer’s concerns if you’ve hopped between multiple positions:

• Emphasize how the experience of working alongside different leadership styles has accelerated your learning and professional growth.
• Focus on your accomplishments in each role rather than your time in the role.
• Highlight how the experience you gained by working across industries and the exposure you acquired to best practices in different types of organizations increased your breadth of knowledge and competence.

For example, one of the best examples I’ve witnessed of articulating the value proposition of job hopping was a sales executive I’ll call Jared. He’d held a couple of sales leadership roles in rapid succession, each for about a year, and I was interviewing him for a role with a company where I worked as an HR executive. Based on Jared’s spotty resume, the interview team was concerned about whether he could commit to staying with the company long enough to have an impact. When I asked about his history of job hopping, he acknowledged it openly, but then elaborated on the advantages of his diverse experience, explaining:

“I’ve recently moved around more than I would’ve liked — but an upside of that are the outcomes I’ve been able to drive with multiple organizations in a short period. I was able to implement sales frameworks, training programs, and incentive compensation models in two different organizations and industries, which resulted in revenue growth of 8% and 11%, respectively — all in just a few months.”  

He went on to thoughtfully describe the diversity of leadership styles he had experienced and industries with which he had become familiar to demonstrate the breadth of skills that he could bring to our company. While we ultimately chose another candidate for the role, we were so impressed by Jared’s transparency, demonstrated agility in different environments, and hustle that we ended up offering him another position in the company.

Unplanned Departures

Finally, another potential landmine in the job search process is unplanned or involuntary departures. Most hiring teams generally prefer candidates who are currently employed, and will likely assume that a strong candidate wouldn’t leave their previous role without a new position lined up. Given this, if a prospective employer sees from your resume that you’ve recently left a role, they will likely ask you about the circumstances surrounding your departure. Whether you resigned, were laid off, or fired, there are a few key considerations to keep in mind when thinking about how you’ll explain the situation:

• While you may still harbor bitter feelings, leave blame at the door when you step into an interview with a new organization. Instead of focusing on the problems with your last position, do the difficult work of finding the positive aspects of your experience with your former employer: What did you learn? What relationships did you build? What goals did you accomplish?
• Reflect on the environments in which you thrive — i.e., a high-growth company, a focus on innovation, a faster pace. Articulate these needs to your prospective employer, and they will read between the lines that the prior organization did not support you in these ways.
• If you were fired, address it head on. Prepare a concise response to explain why you left — i.e., the company/environment/role was not the right fit, there was a change in leadership or direction that changed expectations/dynamics, etc.
• Emphasize the lessons you learned from your time in the role and how they’ve contributed to your professional development.

One of my former clients, Hannah, left her position as Chief Human Resources Officer for a technology company due to a disagreement with the CEO. It was a hasty departure, with Hannah tendering her resignation after a particularly heated discussion with the CEO. We did some work in our coaching sessions to counteract her bitterness and dejection about the situation, and then we thoughtfully prepared an honest, concise description of the reasons she left. Here’s how she articulated the situation to prospective employers:

“I had intended to be with my former employer for many more years. I was hired to lead several key people initiatives, and during my time there, I made substantial progress toward those objectives. However, the CEO decided he wanted to change our approach and reduce funding mid-stream, but still expected to reach our original objectives. This represented a fundamental shift — one with which I disagreed — and I shared my concerns with the CEO on several occasions. I want to emphasize that I am on board with shifts in strategy where necessary, and I view flexibility as one of my strengths. This particular shift, however, was not supported by my team’s research and data, and I believed there was no way the new approach could be successful. I continue to wish the team well, but I just could not sign on for a direction that I didn’t believe would ultimately drive results. And the CEO was not willing to consider that point of view, so we agreed to part ways.”

This approach seemed to resonate well, and after several interviews, Hannah landed a role. The executive teams she interviewed with appreciated her transparency about the circumstances surrounding her last position, and the frank discussion around the importance of collaboration and data-driven decision-making both highlighted some of Hannah’s key strengths, and helped her to better ascertain which organizations would offer an open, supportive environment.

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Especially after a year of uncertainty and widespread job loss (planned and otherwise), it’s more important than ever for candidates to position themselves in the best possible light. There’s no such thing as a perfect resume, but candidates whose job histories include long periods of unemployment, short stints, or unplanned departures must take the initiative to proactively overcome interviewers’ assumptions about these red flags. With the strategies outlined above, candidates can take control of their narrative, present themselves to prospective employers both positively and honestly, and set themselves up for success — in this job and the next.

* Names have been changed for privacy.