CEO Leadership

How To Work With A Risk-Averse CEO

We all work with people who are risk-averse. Reframing their perspective, and doing three things that support your cause will help move them to the right decision.

Joe Woodruff


August 31, 2023

Photo credit:
Ludvig Hedenborg

Robert Fulghum writes:

I’m told that during an international competition many years ago, a man named Frank Marshall made what is often called the most beautiful move ever made on a chessboard. In a crucial game in which he was evenly matched with a Russian master player, Marshall found his queen under serious attack. There were several avenues of escape, and since the queen is the most important offensive player, spectators assumed Marshall would observe convention and move his queen to safety.

Deep in thought, Marshall used all the time available to him to consider the board conditions. He picked up his queen—paused—and placed it down on the most illogical square of all—a square from which the queen could be captured by any one of three hostile pieces.

Marshall had sacrificed his queen—an unthinkable move, to be made only in the most desperate of circumstances. The spectators and Marshall’s opponent were dismayed.

Then the Russian, and the crowd, realized that Marshall had actually made a brilliant move. It was clear that no matter how the queen was taken, his opponent would soon be in a losing position. Seeing the inevitable defeat, the Russian conceded the game.

When spectators recovered from the shock of Marshall’s daring, they showered the chessboard with money. Marshall had achieved victory in a rare and daring fashion—he had won by sacrificing the queen.

To me it’s not important that he won. Not even important that he actually made the queen-sacrifice move. He had looked outside the traditional and orthodox patterns of play and had been willing to consider an imaginative risk on the basis of his judgment alone.  No matter how the game ended, Marshall was the ultimate winner.

Imaginative Risk or Informed Risk

I have been working with CIOs whose CEO is risk-averse. 

If we consider risk in terms of potential loss, then in technology, the greater risk is in doing nothing, staying in place, treading in delay, waiting in the waiting.

The risk averse are blinded to the reality of opportunity debt. But it does little good to point fingers. We need to move a CEO to the right decision. 

We need to reverse the averse.

How do you get buy-in when your proposition is viewed as risky?

I love the phrase Fulghum used above, “imaginative risk.” It’s easily misunderstood though. A person could conceive of it as a leap of faith. We are never asking the CEO to take such a leap.

What Marshall did was the exact opposite: he was able to see many steps ahead so that his decision originated in his mind (imagined) but was certainly informed. He placed his Queen where he needed to. It wasn’t a risk no matter how much people want to frame it that way.

And there is the key: How do you frame a decision so that no one can rightly label it as risky?

The Axiom

The greater the understanding of the need, the less aversion to risk.

The ultimate acknowledgement of need is “We cannot afford to not do it.” What once was seen as risky is now seen as strategic.

A chess player saves the Queen. You can’t afford to lose her. Unless you cannot afford to not lose her. It’s too risky to not do what was once seen as too risky to do.

Gotta write that one again: You want to move your CEO to the place where they realize - “It’s too risky to not do what I once saw as too risky to do.”

The key in this line of thinking is The Need. When we want to move a person to do something that they are at first hesitant to do, we must exacerbate the need for doing it. 

It’s why argumentation doesn’t work. In a recent mastermind group of CIOs, we were talking about remote work and CEOs who were opposed to it. One member said, “I can give him the articles that promote remote work, but he just counters with articles against it.”

Need is the square you must establish for your CEO to make the move.

  • What is the business case for your proposal?
  • What is your competition doing already about what you propose?
  • What are the market advantages your competition will achieve?
  • What is the effect on your customers if you don’t do what you propose?

We can’t rely on the CEO seeing the need for what you propose. You need to spell it out, and better, you need them to speak it.

We establish the need through research, alliance and through questions. 


What is the revenue impact?

How will the customer/client deliverables be improved?

What are hidden cost-savings (such as employee engagement and retention)?

What changes with your position in the market?


Who else sees and supports the need?

Does the CFO confirm the revenue impact short and long-term?

Is Marketing raising the same questions?


If (X - a threat) is reality, what are your concerns?

If (X) goes unresolved, how will that work against us? Now? 3-5 years from now?

If (Y - something that matters to the CEO) could happen, what benefits would we see to the business?

If I can show you how (Z - your proposal), will eliminate (Xs) and enable (Ys), would you help me find advantages and disadvantages to my thinking?

You know what it is like to work with someone who shies away from risk. More often than not, risk is in the perception, and real-need clears away the fog.

Certainly, risk is real. We are not after risking the business. We are after the right perspective, where what was once risky is realized to be very needed. 

"What you have to do and the way you have to do it is incredibly simple. Whether you are willing to do it is another matter." Peter Drucker

You are in the business of increasing willingness.

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