Evolving Leadership Style

Leadership is one of those subjects that ebbs and flows in cycle with the startup and venture capital buzz. It was quite fashionable to discuss a few years ago, today, not so much. It is, however, a very important issue to understand. I want to discuss three different specific elements of evolving leadership.

 1. The first element is that leadership, you as a leader, the leadership style the organization needs, WILL evolve. You cannot run a 500 person company with the same leadership technique as a 10-person startup.

 2. The changes will be manifested in your leadership style which requires you to assess and give considerable thought to ‘what is your leadership style?’

 3. One of the most important elements of leadership style is your authentic leadership voice. This will also evolve.

It seems so obvious when one looks at it from afar, but you will be experiencing this when you are ass deep in alligators. You may not have the natural inclination to step back and assess the changes that are happening or are needed around you.

An example

When I was a combat engineer platoon leader — fresh from four years of military school at Virginia Military Institute, Engineer Officer Basic Course, Airborne School, Ranger School — I was entrusted with a platoon of 50 men under the management of a salty platoon sergeant. I was nominally the leader. The platoon sergeant’s job was to turn me into the leader. He did a bang up job.

When we would train on “platoon in the attack,” I could see all of my individual soldiers. I could direct things with my own actions, voice, hand signals. I could yell at the machine guns. As we got to know each other, we became quite expert at “fire and maneuver” and we were proficient as a platoon in the attack. On our good days, we were very good.

Not quite two years later, I was anointed as a company commander. I had four platoons and tons of stuff — heavy construction equipment, a couple of CEVs (combat engineer vehicles, big blades and winches on an M60 tank chassis with a 120mm bunker busting gun) and more crew-served weapons (a few times including our own mortars).

We would practice “company in the attack” which was a ballet of four platoons individually conducting “platoon in the attack.”

Suddenly, I had 200 men, four platoon leaders — all of my platoon leaders and the company executive officer are beyond my eyesight, were only reachable by radio, and I had to trust them to do their part without my direct supervision.

The difference in such a situation is obvious, real, and stark. It is much more complex to capture a hill when your attacking elements are not within your eyesight and the fate of every platoon is in the hands of another very junior officer.

But, we learned how to do it. My leadership style was forced to evolve. We became very good at it.

One of the companies I commanded blossomed up to 800 soldiers because I was located at a post-Vietnam War out-processing post and everybody in the right MOS (military occupational specialty) was assigned to me to house, clothe, feed, and discipline until they were processed out. [I spent a lot of time shoving paperwork through the system to get combat vets a “drop” and an immediate discharge.]

In this instance, you can see how my leadership style was forced to change and evolve. I had also been trained to do just that.


At the core of evolving leadership style and authentic leadership voice is the issue of delegation. If there is one skill that a CEO/founder has to develop it is the ability to effectively delegate.

If you cannot delegate, you become the critical limitation — the choke point — to your being able to scale. It is a hard nut to swallow, but that is the truth.

In the instance above, I was very comfortable as a platoon leader and a company executive officer because, in part, I had direct control.

As soon as I got the company, I was forced to delegate. Now, instead of working with a platoon sergeant, I was working with platoon leaders, the company executive officer, and the training, motor pool, supply, mess hall, armory, and First Sergeant(s). [I used to make — delegate to — the XO handle the training, motor pool, supply, mess hall, and armory.]

Your span of control — the number of people you supervise and who report directly to you — changes dramatically. Plus, you have a barracks, a training facility, a motor pool,a mess hall, and tons of construction equipment and weapons to deal with.

Delegation, another example

I was the CEO/co-founder of a decent sized real estate company that owned CBD office buildings, suburban office buildings, office showrooms, shopping centers, warehouses, apartments, and mixed use land. Actually, it was a very nice sized company.

One night, I am watching the Ten O’Clock News and I see one of my downtown office buildings (The Littlefield Building, Austin By God Texas) is on fire. Nothing looks as crappy as a night time fire in a downtown building.

I get a call from the chap who is responsible for that building.

“Did you see the news? The Littlefield Building is on fire.”

“I did.” I didn’t say anything else. I could hear him wanting me to give him some direction.

“Who’s responsible for the Littlefield Building?” I asked.

“Me,” he said.

“OK, brief me in the morning. I’m going to bed.”

The gentleman was a very competent man. I had put him in charge of that portfolio. When I did, I told him, “You are responsible for everything that happens or fails to happen with these buildings. Do you understand me?”

“Yes,” he said.

That night, he realized one of the most important lessons of leadership: You don’t GET power; you TAKE power.

He took charge. Everything went perfect. He blossomed and flourished.

Now, did I want to drive down and seize control of things? Of course.

Did I? No.

With great trepidation, I remembered I had given him this job. I delegated the responsibility and while I wanted to go downtown, I did not.

Everything turned out just fine and that man became the COO of the company one day when I was deathly ill. That says something about leadership, delegation, and developing talent.


One strives to attain an effective, genuine, and authentic leadership voice. People think this is a lot of baloney, but it is very important.

This is one of those things that is dependent upon the audience. In the military when you give orders, you adhere to a structure called The Five Paragraph Field Order. You learn how to issue orders in the basic course and in Ranger School. This consistent format is important to both the issuer and the recipient. You issue a lot of damn orders. You revise them often.

You learn a technique called “brief back” wherein you test the clarity of your order by asking, “Please brief back to me what you understand the order is.” I have never, ever, ever had anyone get it right on the first time. [This is my failing, not theirs.] Consider what might have happened if I had not asked for the brief back.

Bottom line it, Big Red Car

OK, dear CEO/founder, take a second and evaluate your leadership style, voice, your ability to delegate and comfort with delegation, and how you need to evolve based on the current and future status of your company.

Is everybody within eyesight?

Are some of them remote workers?

How many workers do you have?

What are the functional disciplines?

How effective is your delegation?

How comfortable are you with delegation?

Do you brief back?

Here are some blog posts that may assist you. Take your time and read them as you have time.

Adapting Leadership Style

Leadership and Leadership Training

Leadership Changes — CEO Shoptalk

Leadership Style — CEO Shop Talk

CEO Leadership — Taking Power

If you use the SEARCH function on the website and type in “leadership,” there are several other blog posts that may be useful, but this is a good start.

OK, there you have it, dear reader. But what the Hell do I really know anyway? I’m just a Big Red Car. Be good. Evolve.car