The paradox of leadership is that to be great leaders, it's best to have to have done the thing we lead people to do. But doing is always a different skill set than leading people.
Yet, although those skills are different, I argue that the best leaders have been in the trenches on what they are trying to lead people to do.
The best of the best manage to satay in the trenches for a long time and still lead.
The trouble is the skills of doing have a half-life that needs refreshing.
If you are a software engineer and you stop coding for a while to manage people, you will get rusty and not be able to code anymore pretty fast. Technology will outpace your skills, and before you know it, everything is outdated. You might know the principles but that's not the point; the challenges your people face will be very different.
We might not love Mark Zuckerberg, but he is effective because he was on the front lines. There is a story of Zuck jumping on an engineering team to build a Snapchat clone; it was called Poke; Zuck laid down some of the code. He was reminding both his people and his competitors of why he is where he is. The same goes for Jeff Bezos. Bill Gates and the Google guys; we're all in the trenches for a long time.
All of those people run massive companies so they can obviously never have done every job in their firm. But whatever skill they had prior to running their massive firms, be it Software Engineering for Zuckerberg, Gates, and Bezos, or Product and Design for Jobs, or sales and marketing. They manage to go back into the trenches with their team and whiteboard things out from time to time. Jobs is famous for having had a super hands on approach with the original iPhone, and Bezos spelled out the famous API mandate as if he was a software architect, not a CEO. All of these people seem to find that delicate balance of having a vision and still going to the trenches when needed.
Pretty much all of the leaders we admire most, the best of the best, George Washington, General George S. Patton, and so on, we're all on the front lines. They were crossing the Delaware River. Never leading from an Ivory tower and always leading from the front.
In the Book War as I knew It, written by General Patton about his WWII experience, he constantly reminds us of his willingness to risk his life in the front lines. Crossing in front of German pillboxes loaded with machine guns, getting targeted by German air. In his own words choosing to cross out in front:
"To reach this, there was a choice of going over a high mountain in the mud on foot, or driving down a road which was under direct enemy observation and fire for about a mile. I selected the road. On the way down, they missed us quite widely, but shelled the Battalion Headquarters while I was there. They must have practiced on the road, because driving back they dropped a salvo of four 150 mm. shells; the first was well beyond us, the second near enough to be uncomfortable, the third threw mud and rocks all over us, and the fourth lit about two feet from my jeep."
Is this all very reckless? Maybe. But maybe also the only way to be a great leader is to do the reckless things your people are forced to do every day. Not that you will ever be as good as them at doing, but you will fully internalize their struggles.
As Drake said: "Make it hard to spot the general, by working like a soldier"
Now to be clear I am not saying that one can't lead without ever having been a doer. Or lead without the capability to get in the trenches and whiteboard something out with the team. But I am saying that the best leaders always get in the trenches.