Strategic Bets: How to Set Your Team Up to Win

Post by Michael Regan on Aug 15, 2017

If you’re setting ambitious goals for the future, the gap between where you are and where you want to be can seem huge.

But looking five, ten or twenty years ahead doesn’t have to be overwhelming. That’s where strategic bets come in.

Strategic bets are the concrete goals and plans a leader uses to spark innovation, develop culture and get the results they want. These are the strategies that will drive you and your team closer to your long-term vision.

Here are six tips to see your strategic bets through with your team.

1. Involve Your Team

Before you fully commit to any Strategic Bet, be sure to take the time to analyze, brainstorm and discuss it with your leadership team.

In his book, “Death by Meeting,” Patrick Lencioni reminds us that strategy meetings are a critical event that all teams should have on their calendars. He suggests blocking out two to four hours each month to meet and review the critical issues that affect long-term success; this would be an ideal time to go over your current strategic bets.

Too often, we think we have a great idea and we rush to implement it without really vetting, researching or thinking it through. In the process, we miss the opportunity that drove the idea in the first place.

Embrace the planning process to develop smarter, more efficient bets.

2. Appoint a Leader for Each Bet

Each bet your team makes should be assigned a captain who is committed to taking the bet toward victory, with the full support of the leadership team.

Even when teammates engage in a healthy debate process prior to choosing their bets, the entire team should be prepared to get behind the bets that are ultimately chosen. As the bets move forward, everyone should support the captains and hold them accountable to seeing them through.

3. Set Milestones

All bets require a solid plan, so get your key milestones on paper as soon as you’ve chosen a bet.

Begin with the end in mind; define a win as specifically and measurably as you can. Schedule time for updates during your monthly strategy meetings and clarify the key metrics you’ll expect the captain to review with the leadership team each month.

4. Invest in Your Bets

Winning may require money, time, people, outside resources and research, so be committed to an appropriate level of investment as you launch your bets.

Much like a home remodel, you may not know the full costs until you start the “demo” phase and find out what’s really behind the walls. Be sure to include margin in all your estimates to avoid the sticker shock that may come as you start to see the impact of your strategic bets in motion.

5. Track Progress Monthly

Winston Churchill once said, “However beautiful the strategy is, you should occasionally look at the results.”

No one wants information overload, but too often strategic bets move too fast or fail because teams made assumptions about their progress rather than examining the data along the way.

Avoid poor results by encouraging curiosity and tracking everything your team learns around the desired result of each bet.

6. Fail Fast

The concept of “failing fast” is very commonplace in the technology world, though it isn’t as familiar in other industries. The principal is simple: embrace failing fast as one of your potential outcomes and use a few key performance indicators to let your captain and the leadership team know when a strategic bet is not heading toward victory.

Once those performance indicators show up “in the red,” have a predetermined plan to let the bet die. The faster you let go of a bad bet, the faster your team will learn from it as they explore creative alternatives or ideas for brand new bets.


Want to schedule time with a coach?

Contact Us!


Michael Regan

Michael Regan

With a combined total of 25 years of leadership experience in the manufacturing, technology and mortgage industries, Michael has a proven track record of delivering results, increasing profitability and leading high-performing teams.

Find Your Business Coach and Transform the Way You Lead