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Are You Guilty of Giving Out This Terrible Leadership Advice? Here's How to Help Others Think Big and Why its Key to Success Thinking bigger sounds easy, but many people struggle with it. Here's why it matters and how to do it.

By Darian Shimy Edited by Micah Zimmerman

Key Takeaways

  • Understand who you work with to empathize with their needs and be maximally efficient when providing resources.
  • Conversely, people who feel unsupported are more likely to interpret a request to set bigger goals as unrealistic.

Opinions expressed by Entrepreneur contributors are their own.

"You need to think bigger" has been said so many times by so many different business leaders that it's become a cliche. But what we tend to forget about cliches is that they are often profound when you look beyond the easy, surface-level interpretation — and this one is no different.

Thinking bigger isn't just useful; it's fundamental for keeping your team competitive and successful. In this article, I share a story about how encouraging my team to think bigger when I worked at Square helped us achieve growth that would have otherwise been impossible.

Setting achievable goals doesn't mean selling yourself short

If you're a business leader, it's almost certain that at some point in your life, you've heard someone stress the importance of achievable goals. Who knows — you may even have given this advice to someone you're mentoring.

In reality, this is the worst advice to give someone as it causes people to assume they're capable of less than they really are. As a leader and mentor, it is your number one job to help people realize they're capable of achieving more — not allow them to set the bar too low for themselves.

Related: Be a Coach, Not a Referee — How to be a Good Mentor and Manager from a Coaching Perspective

Thinking bigger often requires a little encouragement

Most people can do more than they believe. Unfortunately, many of us also tend to get in our way when we're pursuing something important — and the more important it is, the less capable we sometimes assume we are of achieving it.

That's why a little outside encouragement can go a long way. Here's an example:

I remember an annual planning meeting where the Product team brought in a set of metrics and predicted they would grow by 50% that year.

Next, they outlined the projects that would drive the growth — there was nothing wrong with them, but they were safe and obvious.

When they finished, and it came time for me to provide feedback, I had only one question. "What would you need to do to grow by 500% instead?"

Understandably, the team was a bit taken aback. They replied that to achieve 500% growth in the next year, they would have to throw out their current road map and do something entirely different.

"Why don't you go and do that, then?" I replied. I didn't mean this harshly — their original plan was perfectly acceptable by most reasonable standards. But I believed they could achieve more than they realized, and as it turned out, I was right.

Related: 10 Tips to Motivate Employees Without Resorting to Money

It pays to set (slightly) unrealistic goals

Was it realistic to ask the team to shoot for 500% growth in a year? Almost certainly not. But that also wasn't the point. The point was to encourage them to think bigger than 50%, which was playing it too safe.

I didn't expect the team to achieve 500% growth, but even if they grew by 100%, it would still be twice as good a result as what they would have achieved by sticking to the original plan.

As it turned out, we were able to achieve significantly better than 50% growth that year. Crucially, the benefits of encouraging my team to set more ambitious goals went beyond the immediate results. Not only did they achieve better numbers that year, but they also realized that they were capable of more than they had previously believed. It changed their perceptions of what to expect from themselves, empowering them to set bigger goals going forward and work towards them more confidently.

Related: How Leaders Can Inspire Their Teams to Think Bigger

Make thinking bigger easier by following through with support

Encouraging your mentees to think bigger helps them achieve better results and makes them more valuable in the long run by showing them how much more they're capable of doing. But it's only the first step — you also have to be willing and able to provide support for them as they make progress towards the new goals you've encouraged them to set.

When people feel adequately motivated and empowered, they're much more likely to surprise themselves and surpass their own expectations. Research shows that it can also make them more creative and helpful.

Related: 5 Ways to Empower Your Employees

Conversely, people who feel unsupported are more likely to interpret a request to set bigger goals as unrealistic. If you're not careful, this can even breed resentment and create a situation where you'll likely experience pushback.

In my experience, the best way to ensure that your encouragement has the intended effect is to build positive and genuine working relationships with your employees. I firmly believe that knowing your team is the key to providing them with the support and freedom they need.

Darian Shimy

Entrepreneur Leadership Network® Contributor

Founder and CEO of FutureFund

Darian Shimy is the founder and CEO of FutureFund Technology, a fundraising and selling platform for K-12 school groups. He has 25+ years in web-based technologies and managing engineering teams.

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