Red Flags, Green Flags: How to Evaluate a Company Before You Say Yes

Whether you're actively job-hunting, interviewing, or just re-evaluating where you are, knowing how to properly vet a company is one of the most powerful and underrated skills you can build. It's easy to get excited by a lofty job title or a sleek company website, but often, the most critical information - the kind that determines your long-term happiness - is hidden in plain sight.

In this Glass Session, we break down how to look past the marketing, read between the lines, and evaluate a company's health, culture, and growth opportunities before you ever say "yes." We give you the confidence and clarity to make career decisions that truly align with your values.

Actionable Tips & Takeaways

Go beyond the surface level

• Read the job description, and then read it again: Look for key phrases. Does the description focus on outcomes and impact (Green Flag ) or just a never-ending list of responsibilities and a required "ability to thrive in a fast-paced environment" (potential red flag )?

• Audit their financial and industry standing: Look up recent funding rounds, major product launches, or press coverage to understand the company's financial health. If a company is announcing significant restructuring or has had multiple rounds of layoffs, this could be a red flag signaling instability.

• Audit their social presence: Look at the company's website, social media, and press releases to see what messages they're putting out. If their messaging doesn't align with your values, or if their leadership doesn't reflect diversity, this may not be the fit for you.

Dig into the Details

• Deconstruct the compensation philosophy: The salary is just the start. You need to understand their philosophy on benefits, bonuses, and equity. Do they offer a true 401(k) match? Is there a culture of actually taking the PTO they offer? A good benefits package signals they see employees as assets, not just costs.

• Read the reviews, but look for patterns: Employee review sites (like Glassdoor) should be taken with a grain of salt, but look for recurring themes. A single bad review is normal; multiple reviews over time that all mention "lack of transparency" or "burned out managers" is a significant red flag. Conversely, a company that addresses concerns and makes changes based on employee feedback can be a green flag.

Questions to Ask in an Interview

Use your interview time to gather information about stability, growth, and culture. Focus on questions that reveal actions, not just marketing slogans.

• On Stability and Investment:

  • "I’d like to find a home in my next company, and interested in the longevity of employees on your team. What has been your team’s volunteer turnover rate historically? Are you often finding that there is opportunity for folks to stay long-term and develop their careers here?”

  • "How does the company invest in career development? Are there budgets for external courses, or internal mentorship programs?"

• On Success and Expectations:

  • "What does success look like for this role in 6 and 12 months, and what is the training or mentorship path to get there?"

  • "How are you finding that folks are hitting their metrics? Has it been a challenge to meet expectations?”

• On Culture and Values:

  • "How has the company's culture changed or adapted in the last year, and what values guided those changes?"

  • "What are some common challenges you hear from the team? How are team members typically overcoming them?”

Tips for Managers: Be the Green Flag Company

If you are a manager, your job isn't just to vet the company - it's to ensure your team is the kind of environment that attracts and retains top talent. Here’s how you can make your team a definitive green flag for future and current employees:

• Build unshakeable psychological safety:

  • Normalize the conversation: Talk openly about challenges like imposter syndrome or burnout. When you model vulnerability, you create a space where your team is safe to share doubts or challenges without fear of judgment.

  • Encourage healthy debate: Set the expectation that disagreement is a part of collaboration. In meetings, actively encourage team members to disagree by saying, "It’s okay for us to disagree. That’s how we get better outcomes."

• Lead with clarity and trust:

  • Be transparent: Share your own priorities, metrics, and responsibilities so your team understands how their work directly ladders up to leadership goals.

  • Focus on output, not presence: Set clear expectations for performance and manage based on results, not response time on Slack or perceived "time in seat." Let people make their work schedule work for them.

• Invest in their career trajectory:

  • Delegate intentionally: Give your team members projects that stretch their skills and help them grow, not just tasks that fill a gap.

  • Encourage networking: Talk about the value of networking with your team members and share your own experience. Your investment in their career development will be a much stronger indicator of how long they stay and how much value they deliver while they're on your team.