Red Flags

Red Flags: When the Heart Meets the Workplace

We’ve all been there your friend pulls you aside and says, “I see red flags all over this person you’re dating.” They are signaling you to run! Your first instinct? Defend, dismiss, or rationalize.

Maybe they’re jealous. Maybe they don’t see what you see. Maybe those rose-colored glasses are just the right shade of optimism.

In romance, we often ignore red flags until they’re waving directly in our faces. By then, walking away feels like emotional surgery painful but necessary. We learn to proceed with caution in future relationships, ask different questions, and trust our gut.

What happens when red flags appear at work?

The Workplace Dating Game

These similarities are compelling.

The hiring process is essentially professional courtship they tell you everything you want to hear, painting pictures of growth opportunities and supportive culture.

Like dating, those first few weeks feel magical. You’re getting to know the team, feeling out the dynamics, optimistic about the future.

Then Reality Sets In

Maybe your manager micromanages despite promising autonomy. Maybe the “collaborative culture” feels more like constant conflict. 

Or that “growth opportunity” turns out to be doing three jobs for one salary.

Here’s the key difference: in dating, you can walk away with a broken heart. In the workplace, walking away might mean a broken budget.

You can’t simply ghost a toxic boss or swipe left on a dysfunctional team. 

You have rent, mortgages, families, and career trajectories to consider. So, the question becomes: how do you navigate red flags when leaving isn’t immediately viable?

The Leadership Lens

Leaders often have a unique vantage point. They can spot red flags in team dynamics, employee behavior, or organizational culture before others. 

Here’s where many leaders may fail: they assume others see what they see, or worse, they ignore the flags hoping they’ll resolve themselves.

Some leaders sweep issues under the rug, treating workplace conflict like a spectator sport watching from the sidelines to see who emerges with the championship belt.

It’s an uncomfortable truth, but you may have come across leaders who unconsciously allow dysfunction to play out rather than intervene.

Effective leaders don’t just identify red flags; they actively work to address them before they become deal-breakers for their people.

Let’s look at a few strategies for navigating workplace Red Flags:

1.The Reality Check Framework

Unlike dating where friends intervene, workplace red flags often go unspoken. Create your own system:

• Document patterns rather than isolated incidents
• Seek perspective from trusted colleagues or mentors outside your immediate team
• Set measurable boundaries  “If X happens Y more times, I’ll take Z action”

2.The Strategic Communication Approach

In dating, we might hint or hope our partner changes. At work, you need direct, professional dialogue:

• Address issues early before resentment builds
• Propose solutions alongside identifying problems
• Follow up in writing to create accountability

3.The Exit Strategy Plan

Even if you can’t leave immediately, having a plan reduces the panic and desperation that keeps people trapped:

• Build your network before you need it
• Develop transferable skills that increase your market value
• Set non-negotiable boundaries to know what would force your hand to leave
•  

The Leadership Responsibility

Leaders who ignore red flags in their organizations are like friends who watch you date someone toxic and say nothing. Eventually, your best people leave and often they leave for reasons that could have been addressed.

Remember: in dating, we learn to trust our instincts earlier after being hurt. In the workplace, effective leaders help their teams develop those instincts without having to experience the pain first.

What discomfort are you experiencing? What have you tried that simply is not working? 

Let’s find out how we can remove the glasses and get laser focused on the root of the problem so that we can turn it into an opportunity.