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Set Up a Foundation for Success that Works Even in Your Absence

A single gravel path splits into two paths on a wooded hillside with a brown sign on the left.

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As an entrepreneur, it can be difficult to lean into the power of stepping away. What would you do if you had to step away unexpectedly from your business for four months? Perhaps just days after you’d landed your biggest client ever? Could you trust that everything would run smoothly in your absence?

That’s the quandary I faced in July 2019. My company was growing―fast. We had recently signed a client that was 10X larger than our other clients when I got that dreaded phone call: My mother had been diagnosed with stage four cancer, with only months to live.

It was an easy decision for me, in that it wasn’t a decision at all. I would travel to her home state (1,500 miles away) and live there to take care of her during her final months. And I wouldn’t simultaneously run my company during this time; my focus would be fully on my mother.

The only silver lining in this scenario is that when I announced to my team that I was stepping away, I knew they could handle it. 

The Power of Stepping Away is Rooted in Trusting Your Team

How did I know everything would run smoothly? Because my second-in-command and I had recently acquired the tools and professional development to handle it.

Here’s what we did to set both of us up for success. In the previous year, Karen Daniels, my COO, and I forged a deeper level of communication and trust by participating in the Master Key Executive program.

Don’t get me wrong—we had a great relationship prior to the program. Karen and I created and maintained a strong relationship forged from working together for more than a decade. Although I could be vulnerable when sharing business concerns with other entrepreneurs through my EO Forum, there was a level of disconnect between Karen and me in our mutual blind spots.

The Master Key Executive (MKE) program changed that. It provided us with the tools and knowledge to build a bridge across that small gap of disconnect, and now we are stronger and more aligned than I ever imagined possible.

This next-level alignment empowered Karen with the capability to run the company according to the priorities and strategies we discussed in-depth each week for the previous year. She was in my head; she knew exactly what my concerns and priorities were for each facet of the business, and that built next-level confidence and trust.

6 Critical Tools That Empowered Me to Step Away

The tools that MKE provided us that enabled me to confidently step away from my company at such a critical point in its growth are as follows.

1. Up-at-Night Meetings

These were a key step in increasing our understanding and alignment. Karen would ask, “What’s the item that’s worrying you, why is it worrying you so much, and what can I do to help you feel at peace with it?”

We discussed the worries that kept me up at night and why—and I also asked for her list during these meetings. Next, we created a shared Google doc spreadsheet listing each concern and tracking its progress. Just voicing my concerns in this way and knowing she had a handle on solving them eased my worries significantly. 

2. Trust in the Team

I gained confidence that all critical aspects of the business were handled. I used to be impatient, wondering why certain issues weren’t solved at a faster pace. Karen was the recipient of my demands, but didn’t always know their origins. As Karen and I became super-aligned, it helped her understand my concerns and what drove them. That gave her more power to address them and me the power of stepping away.

3. Improved Systems and Processes

Solving my worries over certain aspects of the business resulted in steps that improve our overall workflow. For example, we used to issue annual contract renewals to clients when we were a startup. Now that we have 150 clients, changing to multi-year contracts helps avoid a backlog during renewal season. In addition, our team also solved a cash-flow issue that was bothering me, reducing our collections cycle from 60 days down to 40 days.

4. Documentation

Now that our systems and processes are refined and firmly in place, we’re documenting them in a written playbook. That way, it’s captured for posterity rather than remaining in someone’s head.

5. Focus on the Big Picture

Now that my team has everything handled, I’ve gotten back to what I love about being an entrepreneur: Focusing on big picture strategies, concerns and related next steps. For example, we’ve got a plan to positively impact 1 million lives by our 25th anniversary. I’m focused on the strategy and building relationships to get us there. These big picture concerns are exactly what I should be doing—it’s my highest and best use.

6. Sense of Possibility to Create More Impact

As both a Benefit Corporation and a Certified B Corp, we identify as social entrepreneurs who use the power of business as a force for good. I teach Understanding Social Enterprise at NYU’s Wagner School of Public Service to motivate and support the next generation of social entrepreneurs. The MKE program has given me a renewed sense of purpose with what we can create in our community and in the world.

Renewed Focus On “What, And More Importantly, Why?”

I’ve always known that me getting out of the way allows the great people we hire to do their jobs well. The MKE program helped me regain the clarity that I must remain focused on “What, and more importantly, why?” and let my team focus on the “how and when” of our business.

As an entrepreneur, you have to trust your people. This is key in harnessing the power of stepping away. The more I surrender and let go, the better outcomes are happening. It’s the opposite of Founder’s Syndrome―when you want to micromanage every aspect of the company you created. You just have to let go. 

Here’s proof: After being stuck at a revenue plateau for three years, the year after we participated in MKE, my company’s top-line and bottom-line growth were 20 percent each!

If you’re an entrepreneur who’s considering joining the MKE program, don’t hesitate. Invest in your people. The MKE program is good for you, and good for your team. It will free up your time so you can get back to doing what you love and will help you create more impact in your community.

It’s one of the best professional development programs I’ve ever encountered, and it’s forever changed how I run and scale my business.

Engage with other entrepreneurs who’ve leveraged the power of stepping away to regain their lives and grow their businesses.

Raj Thakkar is founder and CEO of Charter School Business Management, an Entrepreneurs’ Organization (EO) company in New York. The company empowers charter schools with financial knowledge, accounting services and back-office support. The Master Key Executive program is run by Kent Gregoire, an EO Boston member. 

This article was originally published in 2020 at

Allie Frank

Author Allie Frank

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