The No.1 paranoia that all billionaires share —and how you can profit from it

ILLUSTRATION BY RUTH MACAPAGAL

A business is about making the right decisions. Making the right decisions depends upon you seeing the facts.

Unfortunately, that is rarely the case with most business leaders or owners. They are surrounded by blind spots and walls they cannot see through. It is not their fault. It is built into the position of being at the top. You will naturally have a lot of “yes” men and women around you, people who do not want to openly question your authority and who do not want to upset you by telling you how things are.

If you are a business owner, most of the people surrounding you will be more worried about keeping their job than about making you happier or richer or more well-informed. Most of your people do not want to be the messenger who gets “shot” when he or she delivers the bad news.

Your job is to see reality

It happens to me and my team time and time again that once we sit down with key people at different levels and ranks within the organization and with the members of the board and have private talks in confidence with each one of them, the actual reality is far different from what the person at the top, the CEO or owner, think it is. But it is not their fault. People are simply not telling the truth or prefer a version of “selective reality” where important facts are left out.

This is why most of our clients want us to start with the fact-finding phase: a deep investigation to find the real root causes of the major challenges and to give them an accurate picture of reality, because they know they cannot build a skyscraper on a weak foundation. And that foundation needs to be firmly grounded in reality.

We have had several cases with our clients in Asia just over the last 12 months where people would put on their “it’s all good” faces in front of the owners, but in reality, there was major turmoil in the organization. In two cases, the majority of the top management was even deeply concerned about the owner’s capability to run the business day to day. Some had their exit plans already in place and were waiting for the right time to abandon ship.

But who would openly raise that with the owner? Of course, no one would.

In another case, a business owner in Asia had completely pivoted his business a couple of years ago and was now in his “kid in the candy shop” phase I talked about in my column last week. This phenomenon happens with owners who are very passionate about starting new things but need others to think things through for them and make a clear business case analysis for each opportunity versus the owners jumping at any possible opportunity that looks like a great fit (like a kid in a candy store).

You don’t see things clearly

In one case, the head of finance was so deeply concerned about the owner’s spending frenzy and desire to constantly invest in new businesses that she feared for the entire family business conglomerate to collapse soon. Would she ever tell him face-to-face? Of course not. Would she tell him that—from a financial point of view —the party would soon be over and the music would stop? Of course not; she was much too scared she could lose her position.

What about the owner? He lived in complete ignorance because nobody told him the facts. He only saw their smiling faces. My team and I could quickly see that on this trajectory, the business would start to tank in about 19 months.

In our decades of experience advising and consulting Fortune 500 companies, and many famous family business conglomerates around the world, including in Asia, we have seen that these cases are by no means an exception. They are the norm.

In fact, in the overwhelming majority of cases, the root causes of the major challenges are rarely what the people at the top of the owners think they are.

Develop a healthy sense of paranoia

If you are the owner or at the top of an organization, it would better serve you to turn your entire view upside down and assume that people are not telling you the truth, that you do not have all the facts, that you only see a tiny part of reality clearly, and that you do not have all information to make the right decisions.

The best business leaders and business owners adopt this mindset and develop a healthy sense of paranoia. That is why they are so successful.

Steve Jobs did.

Ray Dalio, the American billionaire investor and hedge fund manager, and co-chief investment officer of the world’s largest hedge fund, Bridgewater Associates, says, “If you worry, you don’t need to worry.”

Your goal is not to be liked or to be right

Stephen Schwarzman, the American billionaire businessman, philanthropist, and chair and CEO of The Blackstone Group, has adopted a special approach for any new project or investment idea someone comes up with: they try to shoot it down. They have a meeting in which everyone plays devil’s advocate to come up with all the potential flaws, shortcomings, and risks that the project or idea could have. Only after that do they assess if they are to engage or not.

This is the wise approach. Yet in most boardrooms, the opposite is done. In most businesses, only one or two key people control the board. Not on paper, but in reality,

And everyone else goes along with them or does not want to object. On the surface, they engage in discussions. But on a deeper level, no one wants to question or openly defy the key person’s authority. However, here lies the misunderstanding: it is not about defying authority, it is about getting as accurate a picture of reality as possible to make the right decisions.

That should be your goal as CEO or owner.

To do this, you have to encourage people to disagree and present you with alternate versions of reality to complete the picture that you have.

Think of it this way: if you are trying to cross the jungle with a map that lacks a third of its content, would you be able to still make a safe way through it? Only with luck. If you do not know all the dangers along the way, would you still come out alive on the other side? Maybe. But hope is not a strategy.

As a business owner or leader, you have to go against the natural human grain to be liked. Your goal is not to be liked or to be right—it is to get to the truth. Because if you see the truth clearly, you can make the best decisions.

Encourage open conversations and radical honesty

This is why great business leaders like Richard Branson listen more than they talk—because they don’t learn anything new from talking.

This is why great business leaders are humble—because they know they don’t know everything.

This is why great business leaders encourage open conversations and build a culture of constructive disagreements —because they don’t gain anything from a “yes” man.

This is why the best-run and most successful family businesses have owners who care less about being respected than about their business surviving the next generation—because they know they have to always be on their toes and never be comfortable. INQ

Tom Oliver, a “global management guru” (Bloomberg), is the chair of The Tom Oliver Group, the trusted advisor and counselor to many of the world’s most influential family businesses, medium-sized enterprises, market leaders and global conglomerates. For more information and inquiries: www.TomOliverGroup.com or email

[email protected].