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How to Discover What Matters & Simplify Success

“I want to be a princess who drives a race car and is a YouTube influencer,” my goddaughter sparkled. The sequins on her Cinderella costume reflected the turquoise blue in her eyes. She twirled, creating a kaleidoscope of color on the sun-drenched hardwood floor. “And I know my dream will come true,” she emphasized, “because you told me I can be aaaaaanything I want to be when I grow up.”

After delivering thousands of speeches in my career, how had this petite Princess rendered me speechless?

I paused long enough for her to finish her pirouette. Her tapped toe pointed toward me inquisitively.

“That sounds ambitious,” I postured. “Well, what if you could only choose one career? Then what would you be?” She stared at me like I had snatched an ice cream cone from her mid-lick on a hot summer’s day.

“Why. Would. I. Do. Thaaaaaaaaaaaaaaat?” she screamed. Her pursed lips began to pucker.

And suddenly I saw myself through her eyes for just a moment. I donned a Powerpoint rather than pearls. And a budget rather than a Barbie. But the similarities were striking.

Once Upon A Time

Our new fiscal year was about to begin. I gathered the team in a Town Hall to unveil our revised list of priorities. My energy and enthusiasm was met with stares and silence. Until one baffled employee slowly raised his hand. He inhaled slowly before he spoke.

“This list looks really ambitious,” he observed. “What if we could only do one of these things well? Which one would you choose?”

Where had I heard those words of wisdom before…

Scanning back to the slide of priorities, I paused. And saw the tiny type through his eyes. There were 16 bullet points on the list with as much coherence as my goddaughter’s future career.

If everything is important, then nothing is important.

There are certain initiatives that are important to you right now. Initiatives at work that matter to you, to your organization, and to your customers. When you have more initiatives than the resources to invest in, consider playing the $100 game. A simple strategy to discover what matters most. And to create alignment that results in actions.

The premise of the game is:

If you only had $100 to spend on the initiatives you’ve just considered, how would you allocate it?

To set up the game, you will need a list of items to be prioritized, set up in a matrix with space reserved for the amount spent and reasoning why.

To begin the game, explain the challenge to the group: they have a collective $100 to spend on the list of items. The dollars represent importance of items, and they must decide as a group how to allocate the dollars across the list.

Give the group sufficient time to assign their values, and ask that they also write a brief explanation for the amount. It is possible that groups may bring up the literal cost or effort of items on the list; this may confuse the primary issue of importance and it may be best addressed as a separate discussion, or as its own $100 Test.

When the matrix is complete, ask the group to explain their decisions and reasoning. The matrix can then be used as a guidepost for future decision making on a project; specifically, what items are important and of higher priority than the others.

Of course, $100 isn’t enough to create transformational change around a business process.

You can’t hire a graphic artist or train your engineering department for $100. But it’s a start. Just imagine how you would divide your resources, and your world, if you only had $100 to allocate.

Because, if you can imagine that you have $100 to distribute, you’re going to get creative around what really matters most.

So where would you put your money? Would you drop all $100 on a new software program? Spend $13 on an offsite meeting, and $32 on the warehouse in Burlington? Allocate $20 to hire a new product manager...or two? Divide and conquer by allocating your resources toward what matters most.

Remember to silence your inner critic, as you look towards success. It’s perfectly natural to have some priorities that are out of alignment—there’s no fault in the discovery of what’s only human. There’s a reason why you’re playing the game! It’s always useful and valuable to look at how we allocate and prioritize, because priority leads to commitment. And commitment leads to results. Commit to ignoring any criticism inside the exercise. Start from neutral to accelerate. Make it ok to discover new ways of allocating your $100 and reward yourself for every discovery.

How did you spend your $100? And was it worth it? Make sure you get what you paid for: new insights, and new discoveries!

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