Rethinking Executives

Let’s begin with definitions and disambiguations. Big “E” Executives refer to strategic advisors to the business. Those able add insights that would be disadvantageous for the group to lose. Few people in each org make it to this level of trusted advisor and not all are execs. This is a much smaller (bottlenecked) subset of individuals than the little “e” executives.

Perhaps surprisingly, nothing empirical supports the idea Executives are the key to successful organizations. Consider the number of Executives at failed companies. Frontline managers are typically the largest percentage of management in a company and cultivate most of the workforce. Despite the lack of a correlation between success and Executives, we continue to design and focus organizations around Executives rather than teams. The reverse seems much more logical and scalable. We could fit executives for teams in a much more direct fashion, as we often do with managers and directors, but I suppose the idea of losing them is simply too risky for some.

Many of you may think that experience is the key attribute of Executives that makes them extra valuable. This sounds plausible until you realize experience is a family resemblance term that can mean hundreds of different things and the risk to the company for a failed executive is 100x greater than a typical frontline employee. Ask yourself: Have they executed the “X program” in your culture with your team? What did they lead previously? What evidence is there that their past performance is repeatable in your environment? No doubt these people may have experience — but clearly, subject matter expertise is not enough.

“Executive Presence” aka Less Friction

Quick on the feet, experienced, cool as a cucumber — these are some of the things we attribute to Executives. This is our collective perception of Executives.

We hire a lot of executives on the basis of something we call “executive presence”. As a person who has undergone executive coaching, I can tell you that it’s all largely about not telling coworkers to go kick rocks in a certain way. They still advise you on how to get your feelings out, just in a way that doesn’t shine bright like a diamond on your 360-report. It all feels, a bit fake. I love my coach but I still catch myself wondering if the people with 1/3rd of the company (or some such) should really think more about organizational design and the natural conflicts it can cause. Not many Executives can give you a cogent overview of org design or org psych. The reason “presence” is such a factor? There’s not much else to go on.

Executive presence also acts as somewhat of a moat. People’s aversion to engaging Executives in “serious” debate or playing “the game of giving and asking for reasons” with them for too long has a lot to do with risk. In fact, there is very often blind obedience to many Executive directives. There is less interpersonal friction for Executives due largely to this lesser-known concept called authority bias. Authority bias is the same bias that will have strangers electrocuting you by the way.

Less friction easily translates to more poise. Putting this in reductio form: If you cruise at a certain altitude, you are on your way to being the epitome of a composed, albeit ineffectual, Executive.

This is not to say Executives are the same or that none of them engage in hard decisions involving friction — still, there is an Executive authority that provides Executives a natural lubricant to many situations that you don’t have at lower levels. There are painful types of friction that come with accountability but a lack of authority. You see this a lot at the Director and VP levels.

Execs Are Just Like You

Despite our common view of an Executive there seems to be little evidence of “unflappability”.

From Alex Wilhelm:

A big shoutout to Breslow (Bolt) for speaking his mind. And two cheers for Jack Dorsey, who is busy shitposting his Bitcoin maximalism in the face of a16z and its various acolytes (of course, Andreessen Horowitz is a Stripe investor, per Crunchbase data). These dustups are good, good fun, and useful in that they are doing their bit to bring combat back to tech. Not polite bullshit, but the real scrap. The material fight. The fuck you. The disruptive change.

This is the other side of the executive coin that we so often see applauded. This truth-teller. Half monk and half hitman seems to be the killer combination. The truth-teller role is seldom done with integrity and purpose. Taking this further, we hear about chairs being thrown.

Do We Need Execs?

I’m with John Paul Kotter here; not nearly as much as you might think.

Managers (often Executives) can be powerful forces, but an over-reliance on traditional management to get things done can slow things down dramatically. For example, Executives are an extremely busy and small group that cannot reasonably manage rapid changes given complex interdependencies, even with good data. Strategic change, considered the coolest change around, driven by traditional managerial processes tends to be both slow and ineffective. Traditional management was designed to produce reliable, repeatable performance — not change. Lastly, most successful change efforts capture hearts, not heads. Inspiring is not a typical facet of most traditionally run change efforts.

Any competent person of character, or group with these attributes, can and should:

• Establish a sense of urgency
• Form a powerful guiding coalition
• Create a vision
• Communicate a vision
• Empower others to act on a vision
• Plan for and create short-term wins
• Consolidate improvements and produce more change
• Institutionalize successful new approaches

Can these be enhanced by Executives? Yes. Are executives necessary for this? Nope.

Below the Executive Level

It’s hard to think of many things that are exclusive to the upper echelons of the Executive team that aren’t present in the lower layers.

“The most effective among us have the same number of hours as everyone else, yet they deploy them better, often much better than people with far greater raw talent.” — Jim Collins

Let’s look at the role of a VP of Engineering (credit to LinearB)

As VP of Engineering, we spend most of our time translating between two groups of people in two parallel universes. We’re citizens of both, while not fully belonging to either. We have direct conflicts with peers in Product, Marketing, Data, Strategy, you name it. All without the authority or power of urgency a cofounder.

I was not really one of the developers. I was once, but not anymore. I constantly had to remind the team of the realities of developing software inside a business with goals that are a lot more around revenue, customers and deadlines. Some of them got it. But to many I was now just another executive. If they had assigned me an avatar, he would probably have been wearing a suit, even though I always wear t-shirts.

Missing: Authority

Penalty: Risks your initiatives

The summary conclusion from Executives: Better your people skills

Should You Become an Executive?

It depends on where you think the world is going.

86.9 million Americans will likely be working remotely by 2028. It’s a sign of the times — we’re no longer chained to our desks in offices. Statistics on working from home commonly point out that freelancers are primarily remote workers. The war for talent is increasing and as a result, the talent pool is expanding.

There will be a change in what an Executive (and executive) really is/does. Increasingly we will shift away from directing what’s to be done, setting deadlines for teams that have yet to adequately scope out their work, premature solutioning, and churning out features. This operational style will be replaced by one whose primary goal is to deliver context, deliver challenging problems to supporting teams, and tune their teams for maximum performance.

Times are changing and the new era should have more of a focus on teams than Executives. I believe this is very much in line with the idea of servant leadership.

Cognitive Executive Therapy (CET)

For those of you that still see the Executive position as the mental suit you’ve always wanted to wear, here’s some advice:

Innate mindsets, settings, and dispositions are why we adopt mental models. Without mental models, we are simply at the mercy of our default reactions. Think system 1 and system 2 here:

• System 1 operates automatically and quickly, with little or no effort and no sense of voluntary control
• System 2 allocates attention to the effortful mental activities that demand it, including complex computations. The operations of System 2 are often associated with the subjective experience of agency, choice, and concentration

Charlie Munger argues that consciously developing and applying a latticework of mental models will empower you to see each problem through a variety of lenses and possible options. It’s the difference between solving problems with a single hammer, versus solving them with a dynamic and expansive cognitive toolkit. Mental models are an industry.

My advice. Choose what you give a damn about carefully:

• Whether you realize it or not, you are always choosing what to give a darn about. The key is to gradually prune the things you care about so that you only give a darn only the most important things
• Make sure you have plenty of lessons in the brain bank to share with the company
• Work throughout the organization
• Take calculated risks on people. I’ve built my best relationships by taking risks on people
• Obviate yourself

If you choose to take this path, I hope you are uniquely able to further your organization and its teams.

Closing Out

A lot of Executives have no interest in being the principal educators and ethical leaders companies and employees can benefit from. They become almost entirely ineffective outside of sharing information occasionally and trumpeting the need for growth (an ever-present need in every company).

Rethinking the role of executives in the workplace almost feels like a banal insight to share with Medium, but I hope you find this article thought-provoking and I hope it helps to humanize those that depend on others for their success.

Note: I consider myself an eternal intern