Keep Your Eyes Open: Culture, Red Flags & Trade-Offs Before You Take The Job

“Scott, I knew in the first week that something was off.”

That’s what a client—let’s call her Dana—said in our coaching session. New role, big name company, shiny new title. From the outside? Career jackpot. Inside? She felt like she’d just boarded the Titanic… and no one told her about the iceberg.

But here’s the kicker: She had seen clues. In the interview process. During onboarding. Even in the job description, if she looked closely. But like so many people eager to grow, she swept those instincts under the rug and told herself it was fine. The company was “too big to fail,” the opportunity “too good to pass up.”

Sound familiar?

That’s why I coach clients to create an Eyes Open List before they start—or even accept—a job. Think of it as your personal risk/reward lens for navigating organizational culture. Curious what an Eyes Open List might include? Drop me a message, and I can share a sample.

This article is part of “pulling back the coaching curtain.” I share different perspectives and lessons learned from coaching work with clients. So, let’s talk about this concept of an Eyes Open List.

Why You Need an Eyes Open List

The Eyes Open List isn’t about being paranoid. It’s about being prepared. It’s knowing what you’re walking into, what you’re willing to tolerate (for now), and what’s a dealbreaker.

Let’s be honest: No organization is perfect. Every workplace comes with trade-offs. You’re not looking for unicorns. You’re looking for alignment.

So before you sign that offer letter (or if you’re wondering why you feel out of place where you are now), ask yourself the following:

1. What am I hoping to gain?

Is it a brand name that opens doors? A new title that boosts your resume? Deep technical training or a chance to lead for the first time? Meaningful mentorship?

Action: Write down the 2–3 real reasons you want to make a change and why you’re interested in the role or organization. Consider your expectations. Be honest. That clarity helps you weigh trade-offs when things get uncomfortable.

2. What are my “worth it” trade-offs?

You might put up with clunky systems, bureaucratic processes, or even quasi-poor leadership if you’re gaining prestige, learning opportunities, or strong benefits. That’s fine, if you go in with eyes open.

Action: List 3 things you might be willing to tolerate (temporarily) in exchange for the growth you’re seeking. Set a time limit. “I’ll reevaluate in 6 months,” not “I’ll suck it up for eternity.”

3. What are my culture red flags?

This is critical. Think back to past workplaces. What behaviors or environments sucked the energy out of you? Was it top-down communication? A lack of psychological safety? Toxic leadership or culture? Lip-service DEI efforts? Burnout disguised as “grit”?

Action: Identify your top 3 culture dealbreakers. These are your non-negotiables. If they show up consistently, it doesn’t matter how cool the logo is. The role is not the right fit.

4. What signs should I look for during interviews or onboarding?

Sometimes the red flags wave softly. Other times? They’re flapping wildly and smacking you in the face.

Examples to watch for:

Everyone you talk to seems exhausted.
They use a lot of vague language about “fast-paced” or “wearing many hats” without explaining support structures.
They dodge your questions about turnover or team dynamics.
The expectations for success sound unrealistic.

Action: Come to interviews with 3–5 specific questions that dig beneath the surface (e.g., “How does your team handle disagreement?” or “Can you describe how success is measured beyond KPIs?”). If you aren’t satisfied with the answers, take a pause before you commit.

5. What positive cultural signs matter to me?

Not everything is a warning sign. Look for the green flags, too. You might value:

Leaders who share personal stories of failure or growth.
Teams that joke around and seem like they actually like each other.
Clear expectations for the role and deliverables.
Boundaries about things like after-hours communication.
Internal mobility programs or structured mentorship.

Action: Define 2–3 positive signals that make you feel supported and aligned. When you see them, name them and appreciate them.

A Coaching Moment: Dana’s Do-Over

Back to Dana. After six months of burnout, internal politics, and micromanagement, she reached out for coaching. Together, we unpacked her experience, built her Eyes Open List, and helped her get clear on what she wanted instead of just running from what she didn’t.

Fast forward: Dana just landed a new role at a smaller org, a better fit, and she interviewed them just as much as they interviewed her. She traded the flashy brand name for a culture where she thrives. Where she feels she can make a positive impact. Dana is happy. Her leadership is happy. She enjoys working for the organization, and she feels valued and appreciated for her efforts. That’s what alignment looks like.

Let’s Get Real

You deserve more than a paycheck and a polished mission statement. You deserve an organizational culture that supports your growth, your values, and your well-being. Whatever that looks like and feels like for you.

So the next time a job offer lands in your inbox, or if you’re rethinking the one you’re already in, pause. Pull out your Eyes Open List. Ask the tough questions. And choose with clarity, not just desperation or FOMO.

Because great careers aren’t built on luck. They’re built with intention and alignment.

Are you ready?

Ready to create your Eyes Open List and make sure your next move aligns with the leader you want to be?

Let’s talk. I help professionals and teams navigate change with clarity, confidence, and culture in mind. Contact me to get started.

About Scott Span, MSOD, CSM, ACC: is CEO at Tolero Solutions. As a people strategist, leadership coach, and change and transformation specialist, his work is focused on people. Through his consulting and training work, he supports clients to survive and thrive through change and transition and create people-focused cultures and a great employee experience. Through his coaching work, he supports people willing to dig deeper to identify and overcome what’s holding them back, change behaviors, accelerate performance, and achieve their goals.

_______________________________________________________________________