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14 Entrepreneurs Explain How They Transitioned from Working In The Business to Working On It

As an entrepreneur and business owner, it's easy to get caught by tasks that only make operations effective while the growth of the company cripples. It's important for you to focus on the business expansion after the business stabilizes while letting your employees work in the business. Different strategies such as delegation can be used to help you manage the transition with ease.

We asked entrepreneurs and business owners how they transitioned from working in the business to working on it.

#1- Found the perfect pairing

Photo Credit: Bret Bonnet

It took many years to achieve–heck, more than a decade–but once I finally found a competent marketing director, one who shared the same vision and GENUINE passion for our company, I was able to offload most of the activities that ran me vs. me running them. That's when things started to really click. Once you've found this perfect pairing, do everything you can to protect it. It's not easy, but the past 18 months have been the best ever for Quality Logo Products as I now get to focus on big picture stuff instead of people complaining about the allergic reaction they had to the toilet paper in the men's bathroom!

Thanks to Bret Bonnet, Quality Logo!

#2- Delegating functions

Photo Credit: James Nowlin

Transitioning from working in your business to working on it begins with delegation. You need to recognize that your staff has accumulated enough knowledge and experience to be able to handle your company. You can delegate various functions to them so you can focus more on growing your business. Just keep in mind that just because members of your staff have a different way of doing things, it does not necessarily mean they are wrong. There are several paths to get to one destination.

Thanks to James R. Nowlin,  Excel Global Partners!

#3- Overseeing processes and managing contractors

Photo Credit: Anna Morrison

I read the ‘E-Myth Revisited' by Michael Gerber and had to redefine what being an entrepreneur meant in order to make the leap from working IN the business to working ON it. I believe the difference lies in automation of manual work and the integration of multiple systems to leverage technology and less expensive labor than my own. Working on day-to-day implementation can be valuable at the beginning. However, taking a step back to oversee processes and manage contractors has allowed me to get a real understanding of the whole of my business and given me time to plot its growth and development. By redefining my role, I'm able to work smarter and more effectively, in turn making the ground-level work smoother.

Thanks to Anna Morrison, No BS Supps!

#4- Delegating activities and learning to say ‘no'

Photo Credit: Kyle Brost

Two things deserve all the credit for my ability to work ON the business, rather than IN the business. The first is trusting my team by delegating activities, if I could not delegate to my team, I would never be able to work ON the business. A caveat here is that many times I intentionally chose to work IN the business for a team member, knowing that I will need them to take on something soon. If I haven’t given a little by helping them, it becomes more difficult to delegate. Also, it helps if what I delegate is interesting and engaging. The second is an ability and willingness to say “no”. There are always things to be done and if you can’t say “no”, you’ll end up buried in day-to-day work, that quite frankly, doesn’t matter at all. Every leader has found themselves cleaning the office, when they could be dealing with a strategic effort. As the leader, I’ve also found that I need to be able to say “no” for my team as much as for myself, so that they don’t get burdened with unnecessary work. A mix of being able to delegate and say “no”, is what enables me to work ON the business.

See also  20 Entrepreneurs Explain How They Take Their Business To The Next Level

Thanks to Kyle Brost, Spark Policy Institute!

#5- Hiring the right staff and empowering them

Photo Credit: Guilherme Faria

This is actually one of the turning points in a company’s life, where you see if the business owners have what it takes to sustain their business. One of the common mistakes we see is to hire someone for a high level to a company at an early stage, and that might not fit the needs. In early stages, everyone needs to get their hands dirty, so the big challenge is to hire the right skills for each of the needed positions, but also without burning the whole budget in salaries. With time the transition from IN to ON is natural, as the staff needs to be empowered and not micro managed. But this process cannot be all at once, but instead little by little.

Thanks to Guilherme Faria, Penbrothers!

#6- Several things

Photo Credit: Trave Harmon

In growing my business, what I've learned is this focus on what you do best and primarily do that. Find people who do things better than you and hire them. Outsource the mundane. Concentrate and focus on a goal not within the exact process of obtaining that goal. What we find is that every business is unique as well as every method to sell to them is unique and you must adjust per account in order to obtain it.

Thanks to Trave Harmon, Triton Technologies!

#7- Creating a Culture that understands accountability and responsibility

Photo Credit: Terence Sweeney

Learning about accountability and responsibility was what most changed the way I worked in my business. I started by developing my own awareness of accountability and responsibility and this was a great start. The real breakthrough came however when the conversations about accountability and responsibility filtered down to the staff. When that happened, the effectiveness inside the business improved dramatically and I no longer needed to have the same attention on the day-to-day operations.

Thanks to Terence Sweeney, Highly Valued Business!

#8- Automating things and delegating

Photo Credit: Alaia Williams

As a solopreneur, working in my business is unavoidable – but I've minimized that in the weeds time by having the right systems in place – and using them. I started to keep track of what I was doing, how I was doing it, and how long it was taking me. Over time, I began to look for areas of improvement and, since I'm not afraid to delegate and automate, I started working smarter. I automated things that didn't need my personal touch. I hired assistants – sometimes on a project basis, sometimes on an ongoing part time basis – to help me get things done. These things allowed me to spend time doing the things only I can do (or that I love to do) – connecting with people, growing my network, teaching classes and developing processes that would help me further scale my business.

See also  Essential Skills for Entrepreneurs [ANSWERS]

Thanks to Alaia Williams, One Organized Business!

#9- Delegating responsibilities

As I progress through my business goals, I have positioned myself to work on the business model and structuring the business to expand. I have now delegated responsibilities such as website updates, email responses and other day-to-day operational tasks to third party freelance professionals. I can, now, concentrate on expanding my business to include selecting a marketing team to expand the business globally, corporate structuring to include satellite offices both nationally and  internationally and hiring a recruitment team to bring in the best talent possible.

Thanks to Geneva Pugh, Tennis Education!

#10- Working IN the business all day and ON it at night

Photo Credit: Misty Young

In 2004, I quit my VP/Partnership at a well known marketing firm and bought a struggling restaurant in the mountains near Lake Tahoe, California. While darling and dripping with potential, the place was a hot mess – red notices were posted on the doors, vendors called continuously to get paid on invoices well overdue, no schedule was posted on the wall, the place didn't take inventory or even have a purchasing system. Heck, the incoming phone line was a payphone in the hallway where a hole from the kitchen allowed even cooks to answer. Contrast that with today, there are now 15 restaurants on the books, five of which we own privately, three are franchises and seven more are in various stages of development. The award winning, highly profitable company is completely debt free and serves families in multiple states. How did we do it? Work all day IN, (serving guests, pouring coffee, doing the drawer and mopping the floor) and most the night ON for three years developing systems, processes, protocols, people. It was very tough to do both for three years, but then, I was able to elevate to working exclusively ON the business – created a multi-media training program; focused on duplicatable systems across five key areas (leadership, operations, financials, products/services and marketing); demanded accountability from ourselves and others (this is a family business, mom/dad; daughters and one son in law); held family/partner/business meetings with agendas; started a growth/scale and succession plan and executed relentlessly. It's paid off. Today, we live on the oceanfront and drive a top of the line Tesla, take vacations and teach others how to do what we've done. Life is good, growth will continue to be even better as we further define and refine our systems and stay focused on people.

Thanks to Misty Young, Squeeze In Franchising!

#11- My team's experience over time

Photo Credit: Mike Catania

Even as CTO, a position I've held for almost a decade, I spent the majority of my time working IN business: working as/with a developer for technical performance, reverse-engineering algorithms, and managing employees. A couple of years, it was apparent my team could do all of those things without me and, for the first time, I was free to work on the business, doing things like speaking engagements and media requests. The publicity has been an unexpected boon to the company, and it's allowed a level of personal fulfillment that I didn't realize existed.

See also  30 Entrepreneurs Explain How They Take Their Business to the Next Level

Thanks to Mike Catania, PromotionCode!

#12- Focus on a top-level view of the business

Photo Credit: LaKesha Womack

Many business owners, especially during the start-up phase, struggle with  transitioning from working the day to day operations of the business to working on being strategic and finding ways to grow their business. This is often a result of feeling that no one can do the thing that the business does better than the one who started it. This is a dangerous conception because it builds the business model around the skill set and availability of the owner. In order to make the transition and to start focusing on having a top-level view of the business and its practices, it is necessary to begin setting aside one hour per day to work in the background of the business. During this time, employees should be empowered to carry on the business. This gives them a chance to operate without the owner being involved and seeing the strengths and weaknesses of the business model.

Thanks to LaKesha Womack, Womack Consulting Group!

#13- Maintaining trust and loyalty

Photo Credit: Beth Anne Ball

I hired my best friend lol! I know, not exactly the most innovative tactic but here's the thing- IT WORKED. In one month since hiring her to do the grunt work the company has EXPLODED. Plus, there was little training needed since she knew about the industry and what I did, AND she was already curious about it. She handles the writing and project management and is TOTALLY OK taking lower pay to help the business grow (as I am) because there's a lifelong history of trust between us. We've been on crazy adventures together since about 2 years old- so there was ZERO worry on both her end and mine. Our motto is if I'm writing or managing work, I'm not selling or networking- and not putting processes in place for our ever growing team. You can try all the software, hire the experienced, or find some freelance workers- but nothing trumps 34 years of trust and loyalty. Sometimes, modern and innovative isn't always the best.

Thanks to Beth Anne Ball, The White Rabbit!

#14- Ability to hire the right people and train them

Photo Credit: Neil Mclaren

For an entrepreneur that plans to be something larger than a ‘small business', duplicating themselves should always be a primary goal. Our success in transitioning was due to our ability to hire the right people for the right positions, and train them to replace our physical role in the business. By duplicating our roles throughout the business, we were able to become much more efficient and able to spend our efforts working on the business; which allowed us to progress much quicker. As our organization grew, we put overseeing managers in place and granted them greater responsibility. Now our organization runs like a well-oiled machine, and we can spend our time working on the business, while the team we hired to replace us works in the business.

Thanks to Neil Mclaren,!

How were you able to transfer from working IN the business to working ON it? Tell us in the comments below.

Mercy - CBNation Team

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts, ( and videos ( CBNation is proudly powered by Blue16 Media.

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