328. The Law of Holes
The challenge you face is rarely the actual problem. Sometimes you think you're fixing things, but you're really holding a shovel and digging a hole.
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My client, Gerry, runs a large business unit at a Fortune 1000 company.
Gerry is a very smart guy. He’s also a very nice guy. He is genuinely focused on helping his employees succeed.
In fact, now that I think about it, I don’t know of anybody who doesn’t like Gerry. He’s that type of leader.
Sounds perfect, right?
It’s not.
But you probably figured that out already since the only reason people hire me is to solve major problems for leaders, fast.
So let’s dig a little deeper here
The Person You Talk About The Most
Gerry has this one employee, Andy, that he always talks about. If you know me, you know this is a red flag.
The person you talk about the most is the person you should probably fire the soonest.
Andy is a highly accomplished executive in his own right. He’s got an impressive background (on paper) and was brought on as a senior leader to guide a group of 30 people.
There’s only one problem: when Gerry asks Andy to do something, Andy always comes up with a reason why it can’t be done.
At first, it wasn’t a major issue since Gerry was asking complex questions that weren’t always an easy yes. I get it. But in due course, it became apparent to Gerry that Andy was quick to avoid giving a clear and productive answer, regardless of the question.
Gerry began testing this out with simpler asks, like, “Can you try to communicate more effectively with the sales team?”
Andy would explain why that wasn’t possible.
Over time, Gerry became more and more frustrated with Andy’s lack of accountability in his communication.
So Gerry did what many other leaders do in these situations - he doubled down on pressuring Andy. He did this by intentionally asking more seemingly straightforward questions like “When do you expect to be done with your priority task?”
This still resulted in Andy not giving a clear response.
That’s when Gerry hired me. He brought me on as a leadership coach to help him navigate this challenging relationship. That’s what I do: I solve major problems for leaders, fast.
We didn’t even get fifteen minutes into our first call before I gave Gerry my feedback. It was this:
When you’re in a hole, you always have to remember the first rule of the Law of Holes.
But let’s pause on that thought for now.
First, I want to tell you about William Lyttle.
When You Keep On Digging Holes
William Lyttle was an eccentric, borderline obsessive chap. You’ll realize why in a second.
After his parents passed away in the 1960s, William moved into their house and decided that he needed a wine cellar.
Seems reasonable enough.
Whereas one person might pay a professional to build the wine cellar, Lyttle figured he could do it himself. That’s what shovels are for, right?
So he went down to his basement and began digging.
I told you he was eccentric.
It turns out, William rather enjoyed digging. He enjoyed it so much that, after finishing the wine cellar, he kept digging. And digging. Aaand digging.
He dug a LOT, and he did it for a long, long time.
Over the years, Lyttle ended up digging an extensive network of tunnels that spider-webbed from his basement throughout all parts of his area of London. Some were wide, some narrow, some were shallow, and some deep.
Throughout it all, he managed to keep all his digging a secret. That is, until the town started caving in.
Water and power lines got screwed up.
Buildings began to tilt and shift.
It was when a large sinkhole opened up outside his house that the authorities discovered the extent of William’s digging and the massive amount of damage he had done after 40 years behind a shovel.
He was fined $670k, his shovel was taken away, and he was moved to the top floor of a building where he couldn’t dig anymore for the rest of his life.
And this brings us right back to my coaching client, Gerry, and his non-committal employee, Andy.
The First Rule Of The Law Of Holes
Gerry discovered his challenge with Andy early on in their relationship. From the get-go, he wasn’t getting the type of communication he wanted.
But the challenge you face is rarely the actual problem, it’s often just the symptom. So when you keep pushing further into it, like Gerry did, all you end up doing is digging a deeper hole.
Which brings us to the first rule of the Law of Holes:
When you’re digging yourself into a hole, the first rule is to put down the shovel and stop digging.
Gerry was so focused on fixing a communication issue, he couldn’t recognize that the problem wasn’t about communication - it was about Andy’s ability to fit into the company culture.
When you don’t put down the shovel, you become so focused on digging that you can’t figure out how to get out of the hole.
So, again, the first rule is to put down the shovel.
Put Down The Damn Shovel
Let’s go back to crazy William Lyttle for a hot second. His shovel wasn’t the problem. The real problem was his obsession with digging tunnels.
Similarly, Gerry’s proverbial shovel wasn’t Andy’s communication - it was Gerry’s need to be liked and his avoidance of holding others accountable.
Good leaders sometimes have to disappoint people. In fact, the kindest thing you can do for someone who can’t do the job is to stop pretending they can.
The best thing you can do is to put down the damn shovel.
How To Know When You’ve Dug Yourself Into A Hole
Sometimes it’s hard to recognize when you’re in a metaphorical hole. I get it. But don’t worry, I gotchoo. Here are some symptoms that you’ve been digging a hole:
Continued delays in delivering whatever you’re delivering
Continually going over budget
The same mistakes or errors repeatedly happen
Employee morale drops over a ledge
Any of these resonate with you?
In the same way, Lyttle’s digging was done in secret until the results destroyed the town, your secret digging could cause issues to compound until they suddenly spiral out of control.
So put down the gosh darn shovel.
Here’s how:
Stop trying to fix that thing that can’t be fixed
Have the conversation you’ve been avoiding
Set clear expectations with clear consequences
Recognize that whoever is the Andy in your world may not need different management as much as they need a different job.
What Hole Are You In?
Gerry thought he was being a good leader. After all, he was being patient with Andy (most of the time), and he was giving him multiple opportunities to alter his behavior.
The sad reality is that, by being a “good leader” to Andy, Gerry was being a bad leader to all of his other employees. He was acting just like Lyttle, continuing to dig until the hole was so big, it led to the destruction of morale and effectiveness throughout the company.
So tell me, what hole have you dug for yourself?
P.S. The second rule in the Law of Holes is to get out of the hole.
So once you put down the shovel, contact me. I help you with the second rule - I help leaders solve major problems, fast.
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I’ve seen this so often in teams, where protecting one underperformer quietly signals to the rest that accountability is optional. And once that signal spreads, no feedback culture or values deck will fix the trust erosion that follows. Sometimes, leadership is not about being fair to one person. It’s about being fair to the system.