Escaping Employees – Jack and Diane Chapter 8

Diane sat in her office, staring at her computer screen. The resignation email had just landed in her inbox—another employee leaving.

“Oi, that’s the third one this month,” she muttered.

Jack, leaning quite casually against the doorframe, raised an eyebrow. “Let me guess—blindside resignation? No signs, no warning?”

Diane sighed. “I thought everything was fine. Engagement scores were great But apparently, Mason,one of our best project leads, was miserable and already interviewing. I just don’t get it.”

Jack pulled up a chair. “Sounds like he was on the Escape Journey. By the time you realize it, they’re already gone.”

Diane frowned. “Escape Journey?”

Jack nodded. “Every employee is on their own personal journey, informed by their backgrounds and personal goals” He took a sip of what we believe to be water and continued “The Escape Journey is the worst of these, it’s when employees don’t leave for something better—they leave to get out. They aren’t running toward a great new opportunity—they’re running away from what they have here” 

Diane groaned. “Okay, so why do people end up on this path?”

Jack leaned back. “Three big reasons.” He counted them off on his fingers:

1. Bad Role Fit – They feel stuck in a job that doesn’t align with their skills or career goals.

2. Personal Conflicts – Life circumstances—long commutes, family issues—make staying in the role unsustainable.

3. Toxic Leadership – A bad boss, poor communication, or a dysfunctional team can drive someone out fast.

Diane crossed her arms. “So Mason didn’t just wake up one morning and decide to quit?”

Jack shook his head. “Nope. Escape Journeys happen over time. Little things build up until leaving feels like the only solution.”

How Leaders Can Stop the Escape Journey

Diane exhaled. “Alright, so what could we have done differently?”

Jack smiled. “Funny you should ask.” He confidently strode up to a white board “Here’s how you keep people from quietly disengaging and heading for the exit.”

1. Identify Role Misalignment Early

“Not every struggling employee is a lost cause,” Jack said. “Sometimes they’re in the wrong seat—but they don’t know how to fix it.”

Diane leaned forward. “So we should… what? Check in more often?”

Jack nodded.

• “Ask employees if they feel challenged and engaged.”

• “Look at what they’re good at—can we tweak the role to fit?”

• “Make internal moves easier—people shouldn’t have to quit to find a better fit.”

Diane scribbled a note. “Okay, so stop assuming employees will come to us if there’s a problem.”

Jack pointed at her. “Exactly.”

2. Address Leadership Issues

Diane sighed. “I already know what you’re going to say.”

Jack smirked. “You probably do. Toxic leadership is one of the top reasons people leave.”

Diane nodded. “So we need to…?”

• Make sure employees feel heard. If they don’t, they’ll stop speaking up altogether.

• Create psychological safety. People need to know they can bring up concerns without consequences.

• Model the culture. If leaders don’t walk the talk, employees won’t buy in.

Diane rubbed her temples. “So it’s not just about fixing individual employees—it’s about making sure leadership isn’t the problem.”

Jack grinned. “Bingo.”

3. Catch the Warning Signs

Diane tapped her pen on the table. “Alright, but how do we know when someone’s on the Escape Journey before they quit?”

Jack held up three fingers. “Watch for these early warning signs:”

• They disengage in meetings. Less talking, less participating.

• They slack off. Work gets done—but just barely.

• They start saying vague things like, “I don’t know, I just feel stuck.”

Diane sat back in her chair. “Mason did all of those things. We just didn’t see the pattern.”

Jack nodded. “Most companies don’t, until it’s too late.”

The Bottom Line

Diane sighed. “So this is all preventable?”

Jack shrugged. “Not 100%. But the key is to catch it early. Employees don’t end up on The Escape Journey overnight. It happens slowly, over time, with consistent mismatches between what they need and what they experience.”

Diane glanced at the resignation email again. “Okay, next time, we’re going to see this coming.”

Jack smirked. “That’s the spirit. Now, let’s talk about The Control Journey—the people who are looking for stability, autonomy and balance.

Diane glances at her watch. “But let’s do it next week, if I don’t get home at a decent hour I will be the next Escape CEO”

Jack chuckled. “We can’t have that”.