2 Reasons CEOs Fail

2 Reasons CEOs Fail


Depending on my assessment of a CEOs business and leadership, I ask them one of two questions in my coaching:

"What is stopping you from going faster?"

or

"Why do you need to go so fast?"

Yes, my job is confusing at times, but these questions are framed out of two necessities which, if you fail to do as a CEO, your company won't be successful.

One of my favorite quotes, which I've stolen from a Stanford Research Paper on strategic leadership, is:

"Let chaos reign, then rein in chaos."

I love it because it represents the razor's edge entrepreneurs' walk between chaos and order. The inability to balance on that edge leads to two reasons entrepreneurs fail:

1. You don't let chaos reign.

Safe founders don't win. As a business owner, every day is different. Yesterday's solved problems incubated today's new ones. People quit. Cash comes and goes. You need to pitch an investor today, instill confidence in a team that you can make payroll tomorrow, and sell a customer on how you will change their life over the next year. The chaos is inescapable. Deeper than that, it's necessary. A safe CEO inspires no one, wins nothing, and gets nowhere.

The chaos is vital to discovery, disruption, courage, and customer acquisition. It's that energy that causes employees of stable companies to say no to health benefits and cozy 401k contributions and grab a wing and hang on to the plane you're building. We've all met the chaotic founder and fallen in love with the dream. Adam Neumann, the founder of WeWork, is a great example of a creator of chaos.

When it's just you, the chaos doesn't hurt anyone but you, but what happens when we begin to hire? We've all worked with the CEO, who creates nothing but chaos and suffered under the wrath of constant uncertainty. The one you need to chase down for approval on a piece of creative they're micromanaging, but who can't give you ten minutes of focused attention to make a decision. Chaos, albeit necessary, possesses the power to destroy a company.

2. You can't rein chaos in.

The exact behavior that got your company to live could be the reason your company dies.

Once you begin hiring a team, working with external partners, and increasing distribution channels, your chaos creates collateral damage. The people relying on you for guidance and process creation are swept into your tornado, set up to fail with fingers pointed at their inability to make sense of your vague expectations.

Here are four ways to rein in the chaos:

  1. Get as far ahead with planning as possible.

The chaos is much less disruptive when applied to product releases or marketing campaigns 6 months ahead. It gives your team room to breathe, and doesn't slow you down in your day-to-day when they need approval .

2. Stop giving vague feedback

"It needs to be better."

"It's not good enough."

"It's not where it needs to be."

"I don't love it."

These are pieces of feedback I've heard many CEOs give (myself included), and they are chaotic words. They confuse and frustrate people who want to do a good job for you, and now, instead of executing, they need to track you down to know what you mean. Give direct, clear feedback in short bursts of focused attention so they can get to work implementing the changes you want, and you can return to your chaos.  

3. Stop trying to do it all

Doing more is not being a visionary. It's a distraction. Based on your vision and the plan you've created with your team, agree on desired outcomes and channel your chaos toward those specific outcomes. My co-founder, who was more the chaos in our partnership, used to ask me to help him channel his chaos by clearly pointing him in a direction and letting him use his chaos for good. That works. It doesn't when the chaos is aimless or unwilling to be tamed.

4. Get a team you trust

You'll never harness the chaos if you don't trust the team asking you to slow down. Hire people who you want to change and adhere to processes for because you trust they know what's best for you and the company.


The balance between these two disciplines is an art to master. After reading this today, ask yourself, which side do I lean toward, and what can I do to create balance?

With purpose,

KC Holiday

PS: Here's a clip from my social media about this concept.