The 3 Provocative Questions That Led to a $170 Million Exit

Written by on April 18, 2017

When virtual phone system provider Grasshopper came to CEO Coaching International in 2010, things were going pretty good. The company was profitable, growing, and had already established itself as the top professional communications platform for entrepreneurs.

But seeing changes to their business space on the horizon, Grasshopper wanted to improve on “pretty good.” Five years later, they did: revenue doubled, profits increased 10X, and in 2015 the company sold for $170 million.

So how do you get your company from “pretty good” to BIG?

First, imagine that you are starting a brand new company that is going to compete with your current company.

Then, ask yourself the same 3 Provocative Questions Grasshopper asked itself. These questions can help you completely reinvent your company, and ensure you stay one step ahead of any competitor or new technology that could threaten your business.

1. What am I doing now that I would stop doing in my new company?

Companies get complacent for lots of reasons. Old habits and practices can be hard to break, even bad ones. Employees who have been with the company forever can be hard to let go, even if they are chronic underperformers. Or maybe what’s standing between your company and big growth is right there, in front of your face, and you’re just too close to see the problem. Asking these questions will help you identify some rusty cogs that you can pop out to turn your “new” business into a fine-tuned machine.

2. What am I not doing now that I would start doing in my new company?

Top CEOs and entrepreneurs are always on top of their business spaces, learning about the next big trends and asking questions that lead to transformative answers. If you lagged behind on the last big tech breakthrough, look for the next wave to catch. Or, better yet, create the next big thing that will have your competitors chasing you. In the 1920s, the average lifespan of an S&P 500 company was 67 years. Today? 15. If you don’t adapt your business to embrace what’s coming next, or disrupt your industry, then your business will die, sooner rather than later.

3. How would I compete to try to put my old company out of business?

Whether you’re trying to reinvent your company to improve it, or to save it from a potentially distressed situation, you have to have a clear understanding of your vulnerabilities. Could a competitor undercut your prices? Do you have strong relationships with your top customers, or could a company swoop in and steal a big account you haven’t treated with a personal touch? What about your vision for the company? If you’re aiming for small things, you’re going to stay small. A CEO who’s thinking bigger might swallow your business whole. Take a page out of your competition’s playbook and use it as your own blueprint for new, better, bigger things.

After the CEO Coaching team went through these questions with Grasshopper, we looked up at the whiteboard and saw the outline of a pretty cool company. The consensus was, “We want that company instead.”

If you ask these questions about your business, I think you’ll want the new company you envision too. And once you know what kind of company you want, you’ll be that much closer to putting actionable steps in place that will reinvigorate your business and get you on your way to bigger, better things.


About Mark Moses

Mark Moses is the Founding Partner of CEO Coaching International and the Amazon Bestselling author of Make Big Happen. His firm coaches over 140 of the world’s top high-growth entrepreneurs and CEO’s on how to dramatically grow their revenues and profits, implement the most effective strategies, becoming better leaders, grow their people, build accountability systems, and elevate their own performance. Mark has won Ernst & Young’s Entrepreneur of the Year award and the Blue Chip Enterprise award for overcoming adversity. His last company ranked #1 Fastest-Growing Company in Los Angeles as well as #10 on the Inc. 500 of fastest growing private companies in the U.S. He has completed 12 full distance Ironman Triathlons including the Hawaii Ironman World Championship 5 times.


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