There’s a classic scene in The West Wing where Leo McGarry tells a story to a spiraling Josh Lyman. It’s about a man who falls into a pit. People pass by, offering advice and judgment from above. Then, a friend jumps in with him. The man says, “Now we’re both stuck.” The friend replies, “Yeah, but I’ve been down here before, and I know the way out.”
This “pit” is a perfect metaphor for the workplace. In my 10+ years as a leadership coach, I’ve seen teams fall into it time and time again. The pit isn’t always a dramatic crisis; often, it’s the draining, ambiguous “messy middle” of a major change.
It’s the team struggling after a re-organization, the high-performer suddenly disengaged, or the group paralysis that follows a failed project. As one of my clients, a director, described her team’s “messy middle” transformation, “it was a very draining experience… I felt I ‘probably took too much… on myself,’ trying to absorb the team’s anxiety”.
As leaders, our first instinct is to fix it. We are “doers” who have been promoted for our ability to solve problems. We stand at the edge of the pit and yell down instructions, lower a rope, or simply get frustrated that they can’t “just get over it.”
But this fails. It fails because it’s rescuing, not leading. And it skips the one non-negotiable first step: empathy.
Why We Rush to Fix (And Why It Fails)
In today’s market, we’ve been sold a false choice between results and kindness. When performance dips, we are trained to apply pressure and demand solutions. We treat the pit of burnout or fear as an inconvenience to the project plan.
But high-performing, resilient cultures know that empathetic accountability is their single greatest competitive advantage.
The “pit” is almost always a symptom of broken trust or a lack of psychological safety. Team members are struggling, disconnected, or afraid to be vulnerable. You cannot “manage” your way out of this. You cannot demand innovation from a team that is afraid to fail.
Empathy is the only tool that rebuilds that safety. But empathy isn’t the final solution. It is the non-negotiable starting point for accountability.
My approach, rooted in systems thinking, is that empathy is what allows you to enter the pit. Accountability is the framework you build with your team to help everyone climb out, together.
A Leader’s 3-Step Guide: From Pit to Path
The next time you see a team member or a direct report in that hole, resist the urge to rescue. Instead, use this three-step framework for empathetic accountability.
Step 1. See the Hole (Acknowledge Their Reality)
Before you can solve anything, you must first validate the struggle. This means acknowledging what you see without judgment. This act alone creates psychological safety. Avoid generic phrases like “You seem stressed.” Get specific.
As I coach my clients, this can sound like:
- “I’ve noticed in the last few meetings that you’ve been quieter than usual. I’m concerned about what might be getting in the way for you.”
- “The deadline for this project was missed. I know this isn’t your usual standard of work, and I want to understand what’s happening.”
- “This re-organization is a lot for everyone to absorb. I want to check in on how this is landing for you.”
Step 2. Get in the Hole (Resist Fixing)
This is the hardest part for “doers.” You cannot, as Brené Brown says, stand at the top of the pit eating a sandwich while yelling down, “It’s tough down there, huh?”
Getting in the hole means sitting with them in the discomfort without offering solutions. Your only job in this step is to listen and validate.
- “Thank you for sharing that with me.”
- “That makes perfect sense.”
- “I’ve felt that way, too. I get it.”
You are not agreeing to excuse poor performance; you are agreeing to understand the context behind it. You are demonstrating that you see them as a human, not just a resource.
Step 3. Build a Ladder (Empower with Choice)
This final step is the “accountability” in empathetic accountability. You’ve validated their reality (Step 1) and confirmed you’re in it with them (Step 2). Now, you co-create the path forward.
This isn’t about rescuing. It’s about empowerment.
One of the most powerful examples of this came from a manager I coached. Her direct report was shaken after a colleague spoke to her unprofessionally. Instead of “fixing” it herself, the manager validated the harm and then offered three clear paths forward: “speak to the person directly, escalate through the manager, or ask for her own involvement”.
As my client reflected, “I wanted to give her the empowerment to decide how she wanted to approach it”.
This is the pinnacle of empathetic accountability. The leader held space for the emotion (empathy) but empowered her direct report to own the next step (accountability). She didn’t rescue; she built a ladder.
You Don’t Need a Hero, You Need a System
Leading teams out of the pit isn’t about a single heroic moment. It’s about having a sustainable, repeatable system that all your managers can use.
When your managers are stuck in “doer” mode, it’s not a people problem—it’s a systems problem. They haven’t been equipped with the skills to shift from rescuing to leading.
I partner with organizations to build that system. We move beyond one-off workshops to install a shared vocabulary and practical skills for holding healthy boundaries, giving growth-oriented feedback, and leading teams through the messy middle of change.
If you’re ready to equip your leaders with the tools to build a culture of high performance and deep trust, let’s start a no-risk conversation.
