CEO Shoptalk: Leadership

Leadership at the startup and small company levels is typically something the founder/CEO is doing for the first time in her existence. She is also likely taking the trash out, but this is the nature of small business.

[Pro tip: Relish the chaos and novelty of this experience. Bask in the chaos and learning. Write your Founder Story. Keep a journal. Get regular foot massages. Learn. These will one day be the “good old days” for which you long.]

You should run a company in the manner you would aspire it to be. If you have a company with five employees, run it like you have twenty-five. If you have a hundred employees, run it like it has five hundred.

I do not mean to spend like you are bigger; think and plan like you are bigger.

OK, Big Red Car, what does that mean?

In practical terms that means to focus on the building blocks of the business that a founder/CEO controls or directs:








Do the work and commit this to writing, have it critiqued by somebody who has done it a few times, and then brief it to your employees. This organizational work is the structure upon which the company will grow.

They will think you are a little nuts, but when you reach that first aspirational level, they will realize you were participating, not playing, and think you a bloody genius.

Is this for real, Big Red Car?

Yes, dear reader, it is.

Marking personal experience: I was a 26-year old combat engineer company commander (paratrooper, quite full of piss and vinegar in equal parts), the best job in the Army just short of being a feudal Chinese war lord.

My battalion commander was located a few states away and I never met him for more than a year, never spoke to him, can’t even recall his name today. I was on my own and I liked that.

My TOE (Table of Organization & Equipment) called for slightly less than two hundred combat engineers and gobs and gobs of gear — dozers, loaders, graders, dump trucks, jeeps, chainsaws, explosives, plus a full complement of weapons and ammo to fight like infantry — which is plenty.

In the rarefied period at the end of the Vietnam War, soldiers (draftees) were being discharged from that post at which I resided in waves and masses.

These waves and masses had to be assigned to a unit for training, shelter, chow, discipline, and administration.

Guess where they assigned them? My unit because I was the only combat unit on the post. The rest were all basic training. I got them, the soldiers, 3-6 months before their discharge date and processed their discharge.

Overnight, we ballooned from 186 men to more than 600 and I had to figure out how to manage this horde of young men anxiously and recklessly awaiting discharge. The paperwork load was gargantuan. The discipline was punishing (haha, sorry).

What did I do: I organized additional platoons (companies are made of platoons, platoons are made of squads) until I had 12 fifty-man platoons. This was the equivalent of a battalion normally led by a lieutenant colonel and a complete senior staff. I had five officers including me and a crackerjack first sergeant, but they did give me plenty of sergeants.

By having the basic building blocks of the organization already in place, I was able to absorb the staggering growth.

Then what happened, Big Red Car?

What happened then? They sent me more soldiers until I once had 800 soldiers. The number ebbed and flowed as I worked to discharge them early and get them “drops” on their enlistments.

What else happened? I learned how to lead under pressure (not my first experience with that as I was a soldier after all and had served overseas in similar units), how to scale an organization, and how to both lead and manage a horde.

It was a major league pain in the ass to run a mess hall intended for two hundred and feed many more hungry mouths. We adopted the shift method for every meal and I found a couple of cooks from New Orleans in the ranks who turned out excellent chow at scale.

The single most important element of leadership is one’s personal example, so I took physical training with the soldiers every morning and used to  lead PT once a week.

I personally handled payday and paid every soldier (the Army paid in cash in those days with just the beginning of direct deposit) which gave me an opportunity to ask, “Do you have any problems?”

On payday in the Army, everybody wears their dress uniform, has inspection at dawn, speaks perfect English, can do math in their head, and is anxious to get downtown and convert their meager pay into inebriation.

I think I averaged about 5% of my unit sleeping it off in the stockade on every payday.

As soon as every man was paid, they had leave for the rest of the day and I never went to bed until every man’s pay was sorted out correctly. Sometimes this took until midnight and I had gotten up at three in the morning to go count out the money.

Perhaps my only truly novel ideas was I ran the snot out of that unit and had a huge vegetable garden to augment the mess hall chow. When I turned over that unit, I had a surplus in my mess hall account at the commissary.

On a few occasions when I thought discipline had gotten lax, we ran more than 10 miles in the early AM after 45 minutes of calisthenics. Everybody ran including the platoon sergeants and first sergeant — lots of bitching, but they ran. We always ran at least 5 miles and, generally, the barracks — normally overcrowded and loud — was quiet by 8:00 PM as I also worked them hard all day. They were hardworking combat engineers after all.

Management v leadership

In these type of discussions, it is always necessary to differentiate leadership and management.

Leadership defines the vision and the ultimate objective of the enterprise whilst management makes sure the journey is efficient and everybody gets chow and their blisters treated.

In the early days of the CEO founder shtick, you are both, but as you grow, you delegate management.

Bottom line it, Big Red Car — tee time

OK, dear reader. Here is the takeaway:

 1. Be a leader. It is a hard job and requires a lot of thoughtful planning, but success — both personal and organizational — is based on the quality of leadership.

I see gigantic deficiencies in leadership because the average entrepreneur has zero leadership training. They are generally self taught.

 2. Plan to lead the company or enterprise you see over the horizon. Plan for the future.

 3. The difference between good and great is leadership.

 4. Leadership is a trait you can learn like swimming. After you learn the basics, it’s practice, practice, practice. Don’t start out with the butterfly, but you’ll eventually get there. You will see almost immediate results.

 5. Damn it, do the work. Commit to writing Vision, Mission, Strategy, Tactics, Objectives, Values, and Culture. Do the damn work. It will be tremendously invigorating and it will be a monumental tension reliever.

 6. Leadership is the ultimate monkey see — monkey do. Hang out with a better class of monkeys and watch.

Now, dear reader, go out there and bite the ass off a grizzly bear. You got this.

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car, but I was once a feudal Chinese warlord combat engineer company commander and I was honored to serve my country.