If you're a dog lover like me, you know the drill. You take the dog for a walk, only to realize half way through that it's really the dog who is walking you around the neighborhood. 

Running a business is not much different. Every entrepreneur has faced the same fundamental challenge, starting a business to pursue a dream of doing what you love only to wake up one day realizing it's the business running you. It sneaks up, but ultimately happens to us all.

Getting back to working "on" the business rather than just "in" the business requires a commitment to addressing some fundamental issues. Here are four ways to do exactly that:

Design for accountability. 

Don't just reshuffle the deck chairs of your existing leadership team, rethink how you design your organization in the first place. For many, organizing their leadership team starts with people on staff and functions they play and often involves fitting square pegs of capabilities into round holes of job descriptions.

Instead, wipe the slate clean for a moment and design the right organization and accountabilities to optimize the business. Only when that is in place should you fit the right people in the right seats. Doing this will ensure you don't just have people you like supporting you, but people you can trust are the right ones to take you where you want to go.

Build a simple scorecard.

With the right people in place, the old Russian proverb "trust but verify" becomes more achievable. Having a few key performance indicators (KPIs) in place, with clear ownership and targets, enables you to step back and empower your team to deliver success, with a level of transparency that ensures you can see bumps and challenges in time to impact them.

The key word in all of this is "few." The right data is critical, while too much data is crippling. I use what I call the desert island test--if you were on a desert island, what five to 15 metrics would you need to know to have a real pulse on your business?


The best way to keep great people is by stepping back and enabling them to accomplish great things. As an entrepreneur, this is one of the most difficult things to do, but it is the inability to do this that has us so mired in the weeds in the first place.

I have always worked to surround myself with people who are better at what they do than I am, but for this strategy to work, you need to guide them, not do their jobs or expect them to execute the way you would.


In all likelihood, many of the challenges that exist in your business were the result of day-to-day "creeping incrementalism" that combined a series of good ideas over time and turned them into a dysfunction salad. Solving this will require everyone in your company to feel empowered to raise issues they see in their daily lives.

Quite literally every team member I have ever had a one-on-one with sees things that would make their jobs better, but you often need to draw it out of them. This is a fundamental cultural issue, and results in the people who live with this salad every day taking the attitude "It's just the way we do it." 

Start celebrating as a company when someone raises an issue. Make it clear that everyone matters. Listen more than talk, and dig where your people tell you to. They know where the treasure trove of increased productivity is buried. Make sure to keep an issues list to ensure you don't lose sight of important ones that can't be solved right away. 

These four steps will enable you to get back to working on the business instead of in it and enable you to focus more of your attention on what you love doing most. Now, get back out there and show that dog who's boss!

Published on: Aug 14, 2019
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