Success Isn't Linear — 5 Tips to Overcome Obstacles and Find Your Winning Strategy

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Starting and maintaining a successful business is rarely a perfect upward trajectory. As a business leader, you will face many situations that test the core of your vision, your stamina and your motivation on the journey to success. When these challenging events occur, it’s often helpful to think about the experience as parallel to playing a strategy game. Here are five rules for winning when you face tough times in business.

1. Be resourceful

In any business endeavor, you can reach a point of overconfidence, only to unexpectedly sink into disappointment. Games may be about winning and losing, but winning is about strategy.

One method of meeting adversity could be called “flipping the game.” Rather than seeing a setback as “something that happened to me,” I get resourceful. People move on; business partners leave. Being resourceful means planning for inevitability. I am always looking for new talent. I don’t usually hire in a crisis; I hire people who can handle a crisis. This way of thinking is different from so many leaders who find themselves managing disaster after disaster. Think of strategy as a way of managing the wins — and the losses.

2. Be proactive

I’ve implemented procedures to address some of the worst-case scenarios. You have to ask uncomfortable questions, such as, “What would happen if an employee committed identity theft and stole money from the company?” or “What if a remote worker quit and kept company equipment?” I also use training manuals with helpful links and create resources to help employees with the onboarding process and the everyday information they need — to keep their frustration at a minimum. Avoiding repetitive requests and ensuring your staff has what they need is a big part of planning for the inevitable.

Another tool I use is making good use of downtime. I schedule my entire day so that I can be up early when I’m at my peak and everyone is still asleep. I read emails, do research and check my to-do list. You can flip the day — and the game — so that you are in control of events.

3. Look for what is not visible

The game of chess may seem simple. On the surface, there is no hidden information. All the pieces are on the board. However, you are not merely looking at the pieces on the field of play. Instead, you are looking at all the potential moves — those that will put you in jeopardy and actions that can defeat the competition.

It’s tempting to react to everything from market trends to economic forecasts. Many leaders abandon their plans when things don’t go according to expectations. But with chess, you move with intention based on a specific strategy. Staying on offense is key.

While developing a game plan may feel too structured to you, it’s a vital first step in living your life and running a business. Your plan becomes your philosophy. It’s how you respond to crises and who you are, in good times and in bad, that counts. Your consistency creates your brand, even more than a great marketing campaign.

4. Learn to let go

I’ve learned to relax during the tough times and observe, listen and wait. Patience is key during a crisis. Much like the long deliberations of chess players, I take the time to process information without reacting too quickly.

There will be times when employees betray you. You may realize that your trust in someone important has been misplaced. It’s vital to step back and develop a plan going forward in the situation rather than overreacting and adding to everyone’s stress level.

It’s easy to allow pressures, and even individual people, to rush you, manipulate you or pressure you to make decisions. When I film a TV show, I often feel like everyone is trying to direct me, but I have learned to keep focused and slow things down so I can hit my marks.

5. Let others make you better

Some of my best mentors challenged me in the best ways. I now seek out people who “ruffle my feathers” and refuse to tell me what I want to hear. Surrounding yourself with people who indulge you is dangerous. I’ve learned the hard way that not every idea I have is great. Sometimes, I only have a seed of an idea, and it takes my network of business associates, partners and employees to help me develop it into something worth pursuing.

In the game of poker, you rely on every other player to supply something you need. You learn to “read the room” or “read the table” to determine who has the corner market on what you need to know. Someone’s “hand” may look better than yours, but the truth is that they were only using the resources they had. It’s also possible they were bluffing to cause you to back down. The difference is patience, the gift of observation and learning when to say “no” to opportunity as well as when to say “yes.”

In business, I’ve learned it’s not the cards you’re dealt that matter most, but what you do with them. Discarding is how you play the game. Knowing when to quit a program that isn’t producing results is a good example. On the other hand, folding too quickly can be devastating to a company. Being patient enough to allow your company to get through the growing pains can take you from a place of instability to a firm foundation for exponential growth.

Winning in business is knowing how to use the right strategy to play the game well. Sometimes, all you can do is stay in the game. Everyone around you is angling for an advantage. The stakes are high, but if you slow down and find the right strategy ahead of time, you will uncover the moves that take you to the top.

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