4 Steps to a More Ambitious 2020 Plan

Bob Bailey
Higher Order
Published in
3 min readOct 1, 2019

If you’re like most businesses, then it’s planning season. Loads of deep dives, decks and loads of data. Assuming things are going OK, there’s not a ton of imminent pressure to change. There’s an inner voice that’s lulling you into a passive state of confidence, creating a tendency to keep on doing what got you here. “It’s working; bonuses are a lock; let’s not rock the boat.”

You need to give that voice a beatdown right now. The problem with simply making tweaks to this year’s plan and rolling it out next year is that it rests on the assumption that your competitors are thinking and doing the same. They are not.

Comfort. Overconfidence. Complacency. Incremental planning.
ALL are gifts to your competitors and letdowns to your customers.

It’s not too late. Take another look at your plan through this lens:

Get Outsights — Plans are loaded with data points and insights generated by BI teams. They tell an important story about what you did, but they are not telling you what others did, why and what they are potentially doing to disrupt you. Look beyond your specific industry for trends that can help you and hurt you. Picking the right trend is like odds making: You can be an average performer in a growing trend and crush it. Conversely, you can be the best player in a negative trend and stand still — or worse, lose ground. (Strategy Beyond the Hockey Stick, McKinsey, 2018)

“Self-Induced Paranoia” — Sounds great, right? Seriously, try this: Imagine for a minute that your business is tanking — Customers are defecting; you can’t get new ones to replace them; your go-to channels for sales are dried up. Now dig into all the possible “whys” for the decline. You may discover you have a few possible issues that could derail your 2020 plan. The key is to listen to this and reassess your recommendations in light of this new thinking.

“What must be true?” — It’s easy to think about why you shouldn’t push the thinking. So, instead, ask yourself, “What must be true for this to work?” This will help you see the conditions you must create to be successful. And when you are the one creating them, you’re in the driver’s seat and leading. I promise you’ll get farther, faster, using this framework and acting on it.

Fund Your “Next Version” — Thinking of your business as a static thing that must be maintained is a fallacy that will suffocate you. Instead, think of and discuss your business today as the “current version,” knowing that it must change if you are going to fulfill your leadership duties to your people and customers. When planning, you must allocate budget to the next version more heavily than the current, even if it’s slightly ahead of revenue and brings on the slight pit in your stomach. (Strategy Beyond the Hockey Stick, McKinsey, 2018)

It’s never too late. Break out that plan that is nearly approved and run it through these filters. Shoving around your assumptions and decisions can create some new clarity in your planning process. You’ll move your business ahead more ambitiously and provide more opportunity for the ones that matter most — your people.

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Bob Bailey
Higher Order

CEO and reformed drummer, always at your service.