Leading People Out of the Pit
Welcome to another Toolkit Tuesday! Every week, our goal is to give you a practical leadership tool to put in your toolkit.
So There I Was…
... learning how to hover in flight school, and I wanted to quit. My instructor pilot, a grizzled Vietnam vet with thousands of hours flying the Huey, could hold a perfect hover just by staring at the controls. Or at least that’s how it seemed.
Meanwhile, my first few hours looked more like a mechanical bull ride. The helicopter lurched up, down, left, right, forward and backward while spinning like a top in both directions. I was trying not to panic. I couldn’t hold a steady hover, and I definitely couldn’t see a way forward. That’s when I started to fall in the Pit of Despair.
After our third instruction flight, my instructor could see it on my face. He took the controls, stabilized the aircraft in a perfect 3-foot hover, then gently set it down. He looked over at me and said, “Take a few deep breaths. Shake your arms out. Grab a drink from your canteen. Have a smoke if you want. Just relax.”
Then in the calmest, most reassuring voice, he said, “Matt, you’re doing great. In fact, you’re right where you should be.”
He gave me a few more tips and showed me what to watch for. And by the very next flight, I was hovering in place. Not perfect, but steady. And I was back on track.
The Challenge
At some point in the development process, your people will feel stuck, overwhelmed or like they just don’t have what it takes. This is the Pit of Despair. If you ignore it or get frustrated with them, they may check out, disengage or start going through the motions just to survive.
The cost is high. You lose potential, momentum and often the person altogether.
The Tool: Pit of Despair
As we covered last week in the Developing Others tool, people go through four key stages of learning. Somewhere between realizing how hard the skill really is and trying to apply it on their own, many fall into the Pit of Despair.
This is where doubt, fear and frustration take over. They feel like they are failing. They may think they are letting you down. And they wonder if they should even be in the role at all.
The leader’s job is not to push them harder. It is to become the ladder out of the pit by offering three essential things:
Time – Both formal time to build the skill and informal time to build trust.
Vision – Short-term clarity on what to do next, plus long-term vision for how they fit and why they matter.
Encouragement – Specific, sincere and timely words that build belief and remind them they are not alone
If you provide these three things with consistency and care, your people will not just climb out. They will come out stronger, more confident and more connected to you as a leader.
Why This Matters Now
Everyone ends up in the pit at some point. What determines the future is what happens next. A careless or frustrated leader leaves people stuck. A wise leader builds a ladder.
If you want to build strong teams that don’t fall apart under pressure, you need to recognize when people are in the pit and know how to lead them out of it.
The Result
When leaders show up with time, vision and encouragement, they do more than rescue people from failure. They build trust, resilience and performance that lasts. The people you help out of the pit often become your most loyal and high-performing teammates.
Because they remember that when they were at their worst, you believed in their best.
Take Action
Think of someone on your team who may be stuck in the Pit of Despair. This week, give them one meaningful dose of Time, one Short-Term and Long-Term Vision conversation, and one Encouraging word.
Want to build leaders who know how to coach others through the pit? Let’s talk about equipping your team with tools like this.
Closing the Loop
I never forgot that moment in the helicopter. Not because I got better at hovering, but because someone believed in me when I didn’t believe in myself. That lesson has stayed with me through every leadership challenge since. And now I try to do the same for the people I lead.
Lead hard!
