Balancing Working IN the Business Versus ON the Business

I think a lot about the phrase “working on the business versus in the business”.  Have you heard about this concept? It comes from a popular leadership book, The E-Myth Revisited.

Working ON the business means focusing on the big-picture strategic stuff. Working IN the business means…well, it means working in the business. Spending time in the day-to-day running of the company.

In my first, real SaaS company, I was often coached to work on the business rather than in the business. Coached by mentors, peers, and even by judgment-filled statements in articles, like “When you get bogged down in simple details that your employees could be working on, you are not being an effective leader.” (This link actually goes to a good article, so click on over there when you are done here).

I really, really dislike the advice to work ON the business instead of IN the business. The successful founders I work with echo the same sentiments. I think it’s confusing and easily misinterpreted.

After some trial and error, I learned that for me to be effective, I need to do both. It’s all very theoretical to say that working on the business is the only thing leaders should be doing. But in my experience, 10% of the time on the business is far better than 100% of the time on the business. Otherwise, you run the risk of not actually having a business to work in—just a set of theories and strategies that don’t see the light of the day and worse, that don’t produce revenue.

Working on the business disconnected me from the day-to-day realities of the company, whereas working only in the business kept me very down in the weeds. There have to be both types of work.

IN the business I can spot and solve real-world issues proactively, often before they ever even get to true “problem” status. But it is hard to think strategically and be forward-thinking because when you are so tied to the current operational realities of running the company. So you have to find times to separate and step back to look at the business, think, and plan.

Once, our company was going through a big evolution, and, as a leadership team, we were all working on the business. Our focus was set on shifting to new market positioning and product features that would take us into the next ten years of our industry. It needed to happen. Everyone in the company could see that future state and was excited and onboard. We were all in.

But not enough thought was given to how this would work in the business.

The result? Not catastrophic by any means, but lots of pain and friction that could have been avoided with better operational planning to intersect our future state with our current state. How the new messaging went out to the market, influencing prospects & customers, which then trickled down to sales, and customer success was tricky stuff. There were too many gaps. Too many unanswered questions. And we were only a 40-person company at the time! We were the epitome of agile, it was even a core company value, but we still botched aspects of the transformation because we didn’t have our minds in the business.

While the business was fine and grew like gangbusters once we worked out the kinks, I am pretty sure we left revenue on the table in the interim had we only evolved into it and executed an operational plan grounded IN the current business. In retrospect, a slow evolution, versus an about-face pivot, may have helped the sales and customer teams feel much more fluent and confident in their conversations, which would have built more confidence in our audiences, faster. Operations would have been more prepared for the complexity of new features and new pricing too. A more tactical roll-out plan, that can only come from working in the business, would have increased everyone’s comfort level, knowledge, and preparation.

I see this all the time—usually at a much bigger scale—in large organizations. Leadership sets a vision, a course, a goal, a direction. How that makes its way to the ‘feet on the street’ is so easily messed up absent lots of planning and preparation in the business. Again, certainly, the results are often not disastrous, but they are friction-filled for the market, for customers, for prospects, and for employees. All of which can be avoided with a balance of working on the business and in the business.

So, if you are a company leader berating yourself for not working on the business enough, just do a sanity check. Are you spending 10% of your time on the business? That’s plenty. You do have a business to run after all.

And if you are a leader spending all of your time working on the business, you may really be out of touch with what’s actually happening day to day, thinking too much about strategy and not enough about execution. And I really believe that execution beats strategy. Go to the meetings your teams are having. Monitor the busiest slack channels. Talk to your staff, not just the managers who directly report to you. Talk to customers. Listen to sales calls. Get your head back into your company. You will still be able to lead from the front if you do. Only better.

One framework that helps me when I am struggling to find the balance between IN and ONE the business is “Wheels On, Pedal Down”. It’s never failed me.