Setting Stretch Goals That Will Challenge Your Team

John Rossman

If you don’t set goals, you’ll never reach them. Or like they say in golf, if you aim for nothing, you’ll hit it every time — Yogi Berra, What Time is It

Setting goals is crucial to driving growth, innovation, and success in the current competitive business climate. Not just any goals, but stretch goals. They push boundaries, challenge assumptions, and inspire. As business leaders, we need to set stretch goals that will genuinely challenge our teams and bring out the best in them.

Ray Dalio, the founder of Bridgewater Associates, once said, “If you’re not failing, you’re not pushing your limits, and if you’re not pushing your limits, you’re not maximizing your potential.” This encapsulates the essence of setting stretch goals. They’re about striving for something that initially seems unachievable, pushing the limits, and unlocking untapped potential.

However, setting stretch goals is a delicate art. It requires a deep understanding of your team’s abilities, a clear vision of what you want to achieve, and a strategic approach to goal-setting. 

Here’s a guide to help you set stretch goals that will challenge your team and lead them to unprecedented growth.

Know Your Team’s Capacities

The first step in setting stretch goals is understanding your team’s capabilities and potential. This is crucial because stretch goals are designed to push your team beyond what they believe they can achieve.

Tony Robbins, the world-renowned life and business strategist, has often said, “The only limit to your impact is your imagination and commitment.” 

Understanding your team’s strengths, weaknesses, and potential will help you set goals that stretch their imagination and commitment to new levels without overwhelming them. 

Set Goals that are Ambitious Yet Achievable

One common pitfall when setting stretch goals is creating lofty objectives that need to be more attainable, leading to frustration and demotivation within the team. Stretch goals should be ambitious, but they should also be realistically achievable.

John Rossman, a former Amazon executive, and author, provided valuable insight into this balance, stating, “We need to set big, hairy, audacious goals, but we also need to be realists. We need to understand what’s achievable and what’s not, and strike the right balance.”

Align Stretch Goals with Your Vision

For stretch goals to be practical, they must align with your overall vision and strategy. They should be part of a broader plan and contribute to your company’s long-term objectives. 

As Sheryl Sandberg, COO of Facebook, once said, “True leadership stems from individuality that is honestly and sometimes imperfectly expressed… Leaders should strive for authenticity over perfection.” Stretch goals should reflect your team’s authentic vision and aspirations.

Provide Necessary Resources and Support

Merely setting stretch goals is not enough. You must also equip your team with the necessary resources and support to help them achieve these targets. This may include training, mentorship, tools, and a supportive work environment. 

Teamwork is essential. Not settling for the easy answer or consensus, but willingness to push to get to a better answer takes trust and teamwork. Steve Jobs once said “My model for business is The Beatles. They were four guys who kept each other’s kind of negative tendencies in check. They balanced each other and the total was greater than the sum of its parts. That’s how I see business: great things in business are never done by one person. They’re done by a team of people.”

Embrace Progress and Learn from Failures

Lastly, remember that stretch goals are about growth and learning. Celebrate every step taken towards achieving these goals, no matter how small. And when failures occur, as they inevitably will, treat them as opportunities for learning and growth.

In Amazon’s 2015 Shareholder Letter, Bezos gives a masterclass about innovation, and that it is earned through failure: “One area where I think we are especially distinctive is failure. I believe we are the best place in the world to fail (we have plenty of practice!), and failure and invention are inseparable twins. To invent you have to experiment, and if you know in advance that it’s going to work, it’s not an experiment. Most large organizations embrace the idea of invention, but are not willing to suffer the string of failed experiments necessary to get there. Outsized returns often come from betting against conventional wisdom, and conventional wisdom is usually right.”

In conclusion, setting stretch goals is a powerful strategy for challenging your team and driving growth. It’s about pushing boundaries, unleashing potential, and striving for the extraordinary. As leaders, our responsibility is to set these challenging targets and giving our teams the tools they need to thrive. We are responsible for setting goals and nurturing a culture of learning and development.

Remember that developing and meeting stretch goals isn’t solely about the endgame. They’re about the journey—the learning, growth, innovation, and transformation that comes from striving for something beyond our comfort zone. As you embark on this journey, bear in mind the words of Tony Robbins, “Setting goals is the first step in turning the invisible into the visible.”

Your team may surprise you and even surprise themselves. That’s the power of stretch goals—they reveal what we are genuinely capable of. So set those stretch goals and unlock the extraordinary potential within your team.

John Rossman is the author of The Amazon Way: Amazon’s 14 Leadership Principles and is a leading leadership speaker on goal setting and high-performance teams. If you’d like to discuss your goals, let’s connect


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