What’s The Most Difficult CEO Skill? Managing Your Own Psychology

Ben Horowitz Posted March 31, 2011

It’s f@#ked up when your mind’s playin’ tricks on ya
—The Geto Boys, Mind Playing Tricks on Me

By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology. Organizational design, process design, metrics, hiring and firing were all relatively straightforward skills to master compared to keeping my mind in check. Over the years, I’ve spoken to hundreds of CEOs all with the same experience. Nonetheless, very few people talk about it and I have never read anything on the topic. It’s like the fight club of management: The first rule of the CEO psychological meltdown is don’t talk about the psychological meltdown.

At risk of violating the sacred rule, I will attempt to describe the condition and prescribe some techniques that helped me. In the end, this is the most personal and important battle that any CEO will face.

If I’m Doing a Good Job, Why Do I Feel So Bad?

Generally, someone doesn’t become CEOs unless she has a high sense of purpose and cares deeply about the work she does. In addition, a CEO must be accomplished enough or smart enough that people will want to work for her. Nobody sets out to be a bad CEO, run a dysfunctional organization, or create a massive bureaucracy that grinds her company to a screeching halt. Yet no CEO ever has a smooth path to a great company. Along the way, many things go wrong and all of them could have and should have been avoided.

The first problem is that everybody learns to be a CEO by being a CEO. No training as a manager, general manager or any other job actually prepares you to run a company. The only thing that prepares you to run a company is running a company. This means that you will face a broad set of things that you don’t know how to do that require skills that you don’t have. Nevertheless, everybody will expect you to know how to do them, because, well, you are the CEO. I remember when I first became CEO, an investor asked me to send him the “cap table.” I had a vague idea of what he meant, but I didn’t actually know what the format was supposed to look like or what should be included or excluded. It was a silly little thing and I had much bigger things to worry about, but everything is hard when you don’t actually know what you are doing and I wasted quite a bit of time sweating over that stupid spreadsheet.

Even if you know what you are doing, things go wrong. Things go wrong, because building a multi-faceted human organization to compete and win in a dynamic, highly competitive market turns out to be really hard. If CEOs were graded on a curve, the mean on the test would be 22 out of a 100. This kind of mean can be psychologically challenging for a straight A student. It is particularly challenging, because nobody tells you that the mean is 22.

If you manage a team of 10 people, it’s quite possible to do so with very few mistakes or bad behaviors. If you manage an organization of 1,000 people it is quite impossible. At a certain size, your company will do things that are so bad that you never imagined that you’d be associated with that kind of incompetence. Seeing people fritter away money, waste each other’s time, and do sloppy work can make you feel bad. If you are the CEO, it may well make you sick.

And to rub salt into the wound and make matters worse, it’s your fault.

Nobody to Blame

You can’t blame Jazz Musicians
or David Stern with his NBA fashion issues
—Nas, Hip Hop is Dead

When people in my company would complain about something or other being broken such as the expense reporting process, I would joke that it was all my fault. The joke was funny, because it wasn’t really a joke. Every problem in the company was indeed my fault. As the founding CEO, every hire and every decision that the company ever made happened under my direction. Unlike a hired gun that comes in and blames all of the problems on the prior regime, there was literally nobody for me to blame.

If someone was promoted for all the wrong reasons, that was my fault. If we missed the quarterly earnings target, that was my fault. If a great engineer quit, that was my fault. If the sales team made unreasonable demands on the product organization, then that was my fault. If the product had too many bugs, that was my fault. It kind of sucked to be me.

Being responsible for everything and getting a 22 on the test starts to weigh on your consciousness.

Too Much Broken Stuff

Given this stress, CEOs often make the one of the following two mistakes:

  1. They take things too personally
  2. They do not take things personally enough

In the first scenario, the CEO takes every issue incredibly seriously and personally and urgently moves to fix it. Given the volume of the issues, this motion usually results in one of two scenarios. If the CEO is outwardly focused, she ends up terrorizing the team to the point where nobody wants to work at the company any more. If the CEO is inwardly focused, she ends up feeling so sick from all of the problems that she can barely make it to work in the morning.

In the second scenario, in order to dampen the pain of the rolling disaster that is the company, the CEO takes a Pollyannaish attitude: it’s not so bad. In this view, none of the problems are actually that bad and they needn’t be dealt with urgently. By rationalizing away the issues, the CEO feels better about herself. The problem is that she doesn’t actually fix any of the problems and the employees eventually become quite frustrated that the Chief Executive keeps ignoring the most basic problems and conflicts. Ultimately, the company turns to crap.

Ideally, the CEO will be urgent yet not insane. She will move aggressively and decisively without feeling emotionally culpable. If she can separate the importance of the issues from how she feels about them, she will avoid demonizing her employees or herself.

It’s a Lonely Job

And this loneliness won’t leave me alone
—Otis Redding, (Sittin’ On) The Dock of the Bay

In your darkest moments as CEO, discussing fundamental questions about the viability of your company with your employees can have obvious negative consequences. On the other hand, talking to your board and outside advisors can be fruitless. The knowledge gap between you and them is so vast that you cannot actually bring them fully up to speed in a manner that’s useful in making the decision. You are all alone.

At Loudcloud, when the dot com bubble burst and subsequently sent most of our customers into bankruptcy, it crippled our business and devastated our balance sheet. Or rather, that was one interpretation. Another interpretation, and necessarily the official story for the company, was that we still had plenty of money in the bank and were signing up traditional enterprise customers at an impressive rate. Which interpretation was closer to the truth? In the absence of someone to talk to, that’s a question that I asked myself about 3,000 times. As an aside, asking oneself anything 3,000 times turns out to be a bad idea. In this case, I had two specific difficult questions:

1. What if the official interpretation was wrong?  What if I was misleading everyone from investors to employees? In that case, I should be removed from my position immediately.

2. What if the official interpretation was right? What if I was grinding my brain into sawdust for no reason at all? What if I was taking the company off track by questioning my own direction? In that case, I should be removed from my position immediately.

As is usually the case, there was no way to know which interpretation was right until much later. It turned out that neither was actually right. The new customers didn’t save us, but we figured out another way to survive and ultimately succeed. The key to getting to the right outcome was to keep from getting married to either the positive or the dark narrative.

My friend Jason Rosenthal took over as CEO of Ning about a year ago. As soon as he became CEO, he faced a cash crisis and had to choose amongst three difficult choices: 1. Radically reduce the size of the company or 2. Sell the company or 3. Raise money in a highly dilutive way.

Think about those choices:

1. Lay off a large set of talented employees whom he worked very hard to recruit and, as a result, likely severely damage the morale of the remaining people.

2. Sell out all of the employees who he had been working side-by-side with for the past several years (Jason was promoted into the position), by selling the company without giving them a chance to perform or fulfill their mission.

3. Drastically reduce the ownership position of the employees and make their hard work economically meaningless.

Choices like these separate the women from the girls. Tip to aspiring entrepreneurs: if you don’t like choosing between horrible and cataclysmic, don’t become CEO. Jason sought advice from some of the best minds in the industry, but ultimately he was completely alone in the final decision. Nobody had the answer and whatever the answer, Jason was the one who had to live with the consequences. So far his decision to reduce staff by letting go of primarily the most recent hires has paid off. Revenue at Ning is soaring and team morale is high. If it had gone worse (or ultimately goes bad), it will be all Jason’s fault and it will be up to Jason to find a new answer. Whenever I see Jason, I like to say: “welcome to the show.”

At times like the above, it’s important to understand that nearly every company goes through life-threatening moments. My partner Scott Weiss relayed that it’s so common that there is an acronym for it: WFIO which stands for We’re F#%ked, It’s Over (it’s pronounced whiff-ee-yo). As he describes it, every company goes through at least two and up to five of these episodes (although, I’m pretty sure that I went through at least a dozen at Opsware). In all cases, WFIOs feel much worse than they are—especially for the CEO.

Techniques to Calm Your Nerves

The problem with psychology is that everybody’s is slightly different. With that as a caveat, over the years I developed a few techniques for dealing with myself. Hopefully, you find them useful too.

Make some friends—Although it’s nearly impossible to get high quality advice on the tough decisions that you make, it is extremely useful from a psychological perspective to talk to people who have been through similarly challenging decisions. My friend Bill Campbell was a huge help to me as CEO, but interestingly it wasn’t his great success running Intuit that I found most useful; it was his disastrous experience running Go. Through that experience and his most traumatic days at Intuit (like laying off 1/3 of the company), Bill learned a tremendous amount about how to think about excruciatingly difficult decisions from a psychological perspective.

Get it out of your head and onto paper—When I had to explain to Bill and the rest of my board that, as a public company, I thought that it would be best if we sold all of our customers and all of our revenue and changed business, it was messing with my mind. In order to finalize that decision, I wrote down a detailed explanation of my logic. The process of writing that document separated me from my own psychology and enabled me to make the decision swiftly.

Focus on the road not the wall—When they train racecar drivers, one of the first lessons is when you are going around a curve at 200 MPH, do not focus on the wall; focus on the road. If you focus on the wall, you will drive right into it. If you focus on the road, you will follow the road. Running a company is like that. There are always a thousand things that can go wrong and sink the ship. If you focus too much on them, you will drive yourself nuts and likely capsize your company. Focus on where you are going rather than on what you hope to avoid.

A Final Word of Advice—Don’t Punk Out and Don’t Quit

As CEO, there will be many times when you feel like quitting. I have seen CEOs try to cope with the stress by drinking heavily, checking out, and even quitting. In each case, the CEO has a marvelous rationalization why it was OK for him to punk out or quit, but none them will ever be great CEOs. Great CEOs face the pain. They deal with the sleepless nights, the cold sweat, and what my friend the great Alfred Chuang (legendary founder and CEO of BEA Systems) calls “the torture.” Whenever I meet a successful CEO, I ask them how they did it. Mediocre CEOs point to their brilliant strategic moves or their intuitive business sense or a variety of other self-congratulatory explanations. The great CEOs tend to be remarkably consistent in their answers. They all say: “I didn’t quit.”

diego-corrales-jose-luis-castillo1

Recommended For You
Fintech

new Why the World Still Runs on SAP

Eric Zhou and Seema Amble
Growth

Good news: AI Will Eat Application Software

Alex Immerman and Santiago Rodriguez
General

Forward-deployed Job Titles

Tom Hollands
General

Why Nerds Are More Clippable

Alex Danco

Expert News by a16z

We have built a network of experts who are deeply rooted in technology and how it’s shaping our future. Subscribe to our newsletters to receive their perspectives.

Views expressed in “posts” (including podcasts, videos, and social media) are those of the individual a16z personnel quoted therein and are not the views of a16z Capital Management, L.L.C. (“a16z”) or its respective affiliates. a16z Capital Management is an investment adviser registered with the Securities and Exchange Commission. Registration as an investment adviser does not imply any special skill or training. The posts are not directed to any investors or potential investors, and do not constitute an offer to sell — or a solicitation of an offer to buy — any securities, and may not be used or relied upon in evaluating the merits of any investment.

The contents in here — and available on any associated distribution platforms and any public a16z online social media accounts, platforms, and sites (collectively, “content distribution outlets”) — should not be construed as or relied upon in any manner as investment, legal, tax, or other advice. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment. Any projections, estimates, forecasts, targets, prospects and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Any charts provided here or on a16z content distribution outlets are for informational purposes only, and should not be relied upon when making any investment decision. Certain information contained in here has been obtained from third-party sources, including from portfolio companies of funds managed by a16z. While taken from sources believed to be reliable, a16z has not independently verified such information and makes no representations about the enduring accuracy of the information or its appropriateness for a given situation. In addition, posts may include third-party advertisements; a16z has not reviewed such advertisements and does not endorse any advertising content contained therein. All content speaks only as of the date indicated.

Under no circumstances should any posts or other information provided on this website — or on associated content distribution outlets — be construed as an offer soliciting the purchase or sale of any security or interest in any pooled investment vehicle sponsored, discussed, or mentioned by a16z personnel. Nor should it be construed as an offer to provide investment advisory services; an offer to invest in an a16z-managed pooled investment vehicle will be made separately and only by means of the confidential offering documents of the specific pooled investment vehicles — which should be read in their entirety, and only to those who, among other requirements, meet certain qualifications under federal securities laws. Such investors, defined as accredited investors and qualified purchasers, are generally deemed capable of evaluating the merits and risks of prospective investments and financial matters.

There can be no assurances that a16z’s investment objectives will be achieved or investment strategies will be successful. Any investment in a vehicle managed by a16z involves a high degree of risk including the risk that the entire amount invested is lost. Any investments or portfolio companies mentioned, referred to, or described are not representative of all investments in vehicles managed by a16z and there can be no assurance that the investments will be profitable or that other investments made in the future will have similar characteristics or results. A list of investments made by funds managed by a16z is available here: https://a16z.com/investments/. Past results of a16z’s investments, pooled investment vehicles, or investment strategies are not necessarily indicative of future results. Excluded from this list are investments (and certain publicly traded cryptocurrencies/ digital assets) for which the issuer has not provided permission for a16z to disclose publicly. As for its investments in any cryptocurrency or token project, a16z is acting in its own financial interest, not necessarily in the interests of other token holders. a16z has no special role in any of these projects or power over their management. a16z does not undertake to continue to have any involvement in these projects other than as an investor and token holder, and other token holders should not expect that it will or rely on it to have any particular involvement.

With respect to funds managed by a16z that are registered in Japan, a16z will provide to any member of the Japanese public a copy of such documents as are required to be made publicly available pursuant to Article 63 of the Financial Instruments and Exchange Act of Japan. Please contact compliance@a16z.com to request such documents.

For other site terms of use, please go here. Additional important information about a16z, including our Form ADV Part 2A Brochure, is available at the SEC’s website: http://www.adviserinfo.sec.gov.