C-Suite Agenda

Rig the Game with Four Simple Questions

Dan Nicholson

Most of us in business started because we want to win the game, even if we don’t deem ourselves competitive. Every day, month or year can be viewed as a win or loss. Those who have endured the struggles of running a business know it often feels like gambling: exciting but unpredictable. 

Years ago, I started analyzing how others kept winning. I investigated the icons, studied thousands of client cases, met with masterminds, and scrutinized my own business successes (and failures). Why were some businesses successful while others failed? 

The secret? It depends. 

It’s vague and it’s frustrating, but it depends. It depends on you. It depends on what you want—out of business, and out of life.      

For many, success equals more. More growth, more profit, more people—you get the idea.  

I counsel clients to stop focusing on “more” and start getting clear on what they want. 

This can seem lofty. But with the right mindset, concepts, and tools, you can rig and win your own game.  

In my book “Rigging the Game,” I outline tools to help people determine what they want and tools to help them get closer to whatever that is without doing “more.” 

Some of these tools can be used as “frames”—different glasses you wear when making decisions and playing your game. These are forcing functions that snap you out of cognitive distortions like all-or-nothing thinking (more!).

There are four frames. Using them intentionally can get you in the mindset that helps you win your game. They are specifically intended to put you in the best position to get closer to what you want. 

Each frame has a simple question to help you put the frame on quickly. 

The Parenting Frame: How can you prevent something bad from happening?

First is the Parenting Frame. Here we ask, “if this were my child, how would I prevent something bad from happening?” 

One way to think about the Parenting Frame is through the all too familiar screen time topic. Let’s say you have kids, and they’ve been unusually quiet for a while. As any parent knows, this is usually a sign of trouble. You check on them to find they’ve navigated to a mature website on their iPad. Yep, trouble. 

Now you have a choice. Do you get mad at your kids? Blame the content provider? Your kids’ friends?  

Under the Parenting Frame, we ask ourselves if we have the systems in place to keep bad things from happening before we place blame on factors outside of our control. We ask what the worst thing that can happen is and whether we would be ok if that worst case became reality.  

It boils down to: How can we prevent bad scenarios from happening? How can we eliminate downside risks?

Part of this frame involves preventative versus detective controls. A preventative control is exactly what it sounds like—a control preventing bad things from happening. 

In the context of the mature website example, if we want the upside of having independent children who don’t need round-the-clock supervision, we must mitigate the downside risk by setting up parental controls on the devices they can access. This would be an example of preventive controls. 

In terms of your business decisions, implementing preventive controls means turning a risky (or just bad) bet into a good one by setting up systems to ensure the worst-case scenario that might result from the decision you made isn’t all that bad.

The other approach under the Parenting Frame is detective controls. Sticking with the kids’ iPad example, say I get an email from Netflix listing recent content my kids watched. It looks like Die Hard is their favorite Christmas movie. But I really wish they hadn’t watched it, because they’re still little and not ready for that kind of content. Detective controls come into play when we find out something bad has happened after the fact. That’s not favorable. We want a preventive control over the detective control—in business and in life. 

The Commissioner Frame: Would you be willing to play by the rules of your game in perpetuity?

The second frame is the Commissioner Frame. The Commissioner Frame looks at our business as if it’s a

team we own (in a league we also own) and asks: “Does this align with what I want in business? Would I be willing to play by these rules in perpetuity?”

Some rules are of course necessary. In our businesses, we are the commissioner who gets to determine what those rules are. How do we set parameters that keep the game alive while also keeping it enjoyable?

We tend to forget to look at business as a game (and a game it is). We need rules and we need principles, which are two different structures. Rules are boundaries you don’t cross. Principles are more akin to guidelines. Put another way, if rules are a stop sign, principles are the lane markers you stay between as you drive. 

It can be easy to overcorrect one way or another, to establish too many rules for yourself, your business and find yourself feeling drained. Or you lay off the rules and suffer losses of productivity, morale, or relationships.

Even the NFL deals with this type of balancing act. Maybe you’ll remember when it banned player celebrations for things like touchdowns. Well, that’s not much fun, so the league threw out that rule out to preserve some of the inherent joy in the sport. It’s all about balance. 

It can seem counterintuitive but having rules of the game allows you to compete and operate in ways that you enjoy.

The Investor Frame: Given what you know now, would you choose to opt into this particular situation?”

At its most simplistic, the Investor Frame forces you to ask: “If I had the money required to take this action, would I?”

For example: “The business is worth one million dollars. If I had a million dollars on hand right now, would I buy it?”

This frame still applies if you’ve already made a decision. For example, in terms of stocks and bonds, just because you own those things does not mean you must continue to own them. In fact, the best investors have stop losses in place to help them move away quickly from a bad decision. Once they do, they find a better place to put those funds to use.

For businesses you’re actively involved in day-to-day, I recommend applying the Investor Frame at least quarterly. Apply it more frequently when evaluating a friction point in your business: Would I hire this employee again based on what is currently happening? Would I invest in this marketing campaign again based on the current ROI?

For businesses that you’re not involved in day-to-day, or for other passive investments, the Investor Frame is the default frame through which I view all aspects.

The Professional Skeptic Frame: Why? Can You prove it? 

One of the more common approaches to business is the tendency to question everything. People who constantly ask “Why?” are naturals in using the Professional Skeptic Frame.

“We had a spike in sales last month…why? Was it because I did that podcast interview around that time? A seasonal thing? Do we have more leads around this time of year? Why?”

Professional skepticism is a state of mind where we suspend judgment, expectations and question the information until we have sufficient evidence to determine the proper outcome. It’s like being a three-year-old and continually asking your parents, “But why?” We are in pursuit of complete understanding.

People well-versed in this frame make it their mission to tunnel past the surface into a deeper understanding of the underlying mechanics of the thing in question. You interrogate yourself, the data, ideas, or assumptions with questions to equip yourself to make the best decision. 

To be clear, professional skepticism is not about being negative. It’s not about being annoying. It’s not about being inherently negative or discouraging.

The outcome we’re in search of is truth, but more importantly, we’re trying to free ourselves of biases that impact how we make decisions. 

And those decisions should help us get closer to what we ultimately want—to win our unique game.


Written by Dan Nicholson.
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Dan Nicholson
Dan Nicholson is the author of Rigging the Game: How to Achieve Financial Certainty, Navigate Risk and Make Money on Your Own Terms, deemed a best-seller by USA Today and The Wall Street Journal, among others. In addition to founding the award-winning accounting firm Nth Degree CPAs, Dan has created and run multiple small businesses, including Certified Certainty Advisor, a professional certification he runs through CertaintyU. CertaintyU is a program that teaches business owners methods for increasing financial certainty, minimizing risk, and engineering cash flow. Dan also developed the Certainty App, a financial tool built for entrepreneurs based on the ideologies he teaches. Dan also hosts the Rigging the Game podcast, a resource for entrepreneurs who want unconventional tips to win at business, and is a Consulting Producer for PBS’ Opportunity Knocks.


Dan Nicholson is an opinion columnist for the CEOWORLD magazine. Connect with him through LinkedIn. For more information, visit the author’s website.