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How To Stay Organized Wearing Multiple Hats In Your Business

Written by Jay Mandel
Jay is an Entrepreneur and the Founder of Your Brand Coach
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As a business owner, you are most likely going to have to handle different tasks simultaneously. You may need to take care of things at the management’s end because your staff is simply not equipped to handle them. You may also be challenged to find ways to stay within budget and fill roles that meet essential objectives.

You may need to answer an emergency call or take care of an urgent financial matter. And more importantly, you need to oversee the work of different departments to track progress and growth while also keeping an eye out for mishaps.

So if you are a business owner who has to wear multiple hats, here are a few recommendations to stay organized and productive.

How Do You Wear Multiple Hats?

In a Forbes article on wearing multiple hats, Tracy Brower talks about tips to succeed in these roles. Let’s take a step forward by analyzing the multi-dimensional aspects of taking up multiple roles as a business owner, including skills, tips, and cautionary advice. [1]

Ask yourself some reflective questions to help you realize things about yourself. The answers to these questions will come from you and lead to significant discoveries about your career. Some questions may be straightforward but essential to the self-awareness exercise.

  • Are you working in multiple roles by choice or circumstance?
  • Which role do you enjoy the most?
  • Does it play by your already existing strengths, or do you learn something new in it daily?
  • Which role do you find the most boring or least engaging?
  • Why did you volunteer for it?
  • What motivates you to do it if it’s not your interest?
  • Are you here because you’re struggling with managing multiple responsibilities?
  • Have you started to get tired?
  • Or is this disaster management?
  • Where do you draw the line?

Master of One vs. Master of None

“A jack of all trades is a master of none but often better than a master of one.”

Is this your first time hearing this complete quote? It is, for many. But it has been used for hundreds of years. It was famously used by Robert Greene in his booklet and even referred to William Shakespeare as the “jack of all trades.”[2]

While there is no direct origin of who first said it, the phrase was used many years ago to refer to “jacks” or people who knew different things in life. Like the “average joe” that we have today, “jack” may have been a common name.

This leads to the question, how does this affect us in our daily lives, more so in business? Multitasking is advantageous as long as you know what you’re doing. And that requires plenty of skill. Hence, being a “jack.”

1. Time Management

The most crucial skill you need to hone as a professional wearing multiple hats is managing your time well. There will be times that even your personal space will be invaded, and unexpected calls and meetings can happen over the weekend.

If you have too many meetings, events, or tasks for the day, try to maintain a schedule and divide your time for each role according to the degree of involvement. Have clear boundaries if you have to or adjust according to the situation.

However you want to work around this, time will be an essential aspect of being a business owner. You can find plenty of time management apps on the internet to help you through the process.


2. Clear Judgment

Is that task not worth your 30 minutes? Drop it, or maybe do it later. You need to be judicial with what’s most important to you and how you spend your time, which can only happen with a good sense of judgment.

Your perception also applies to the team you work with, clients you associate with, and gatherings you join. If it’s not worth your time and energy, then you’re better off doing something else that’s productive.

Of course, there are other things that you can do so that these non-essential tasks can still be done. One perfect way is to find the right person you can delegate this task to. This means looking for productive and effective team members onboard your business.

3. Eye for Detail

Wearing multiple hats also requires you to have critical eyes. The tasks you check off your to-do list can come back to haunt you if they have errors or blanks.

If you’re not detail-oriented, you’ll waste time redoing things repeatedly without making progress. When there are problems or issues, your next step is often looking for the solution. While this is a good way of doing things, it might not be the best.

Look for the details first before jumping to any conclusion. There might be an underlying cause that needs fixing. This is where you find the root cause of things. In this way, solving the problem is just a one-time thing, and not putting band-aids every time it arises.


4. Leadership

If your roles require you to work with a team, then you need leadership skills to navigate the challenges of coordinating with others. People are different, and we all have our own opinions.

As a leader, you’ll need to assess, communicate, delegate, motivate, and harness your team’s strengths to increase productivity. It is one thing to push people to do things and one thing to inspire people to move.

Finding the right balance is key to being a good leader.

5. Efficient Workspace Organization

Wearing many hats also means you need a large space to store them all. So your workspace is the closet where you stack all your files, documents, notes, tools, and other necessary work-related stuff.

Keeping your workspace physically or digitally organized declutters your space and mind, making you efficient and clear-headed. Have separate filing cabinets in your office or separate files on your computer.

Setting and Achieving Goals

Juggling multiple roles can be taxing if you lack management or strategic skills. However, practice, patience, and consistency can help you acquire these skills. Here are a few things you can do to ensure you’re on the right track in wearing multiple hats.[3]

  1. Analyze – First and foremost, you must understand your roles’ requirements and create an agenda accordingly. This schedule must be thorough, detailed, and easy to follow.
  2. Set Measurable Goals – Quantify your entire process and share it with your team. Lay out your strategies in front of the team and measure them against percentages and quantities to track your exact progress. Maintain separate track sheets for each role you occupy and revisit them daily, so you are not confused.
  3. Live By Accountability – Create an accountability structure within your teams so that each member ensures that the other is working actively towards the goal. If you tend to lose sight of the goal quickly, ask somebody to maintain accountability with you.
  4. Share Your Aspirations – Your team can’t help you if you’re fighting multiple battles alone. So share your goals and aspirations with your team and find ways to motivate them so they can help you reach your destination faster. Don’t just set goals but also set expectations.
  5. Trust the Process and Your Team – If you’re in a leadership position, it is easy to get sidetracked by multiple goals set under a limited time frame. Often, working with others can prove challenging if there’s a mismatch between your and your team’s pace. However, perseverance and trust are the two most neglected elements of successful goal-setting, so make sure to push through!

Keep Your Eyes Open

The ability to wear multiple hats is a fun and fulfilling role. It makes you part of most things in a business and also allows you to see things that others don’t. But, there are things that you have to look out for. Here’s what you shouldn’t do when wearing multiple hats.

1. Don’t Expect to Know Everything

Let’s face it, it’s not humanly possible to know everything. You’re not a computer, so why act like one? Being clueless happens to the best of us and often in the worst time.

Don’t panic if you can’t find the solution to a problem or if your colleague suddenly asks an unanswerable question. You will find a solution soon enough if you take the time to solve it.

2. Don’t Be in Charge of Everything

Now, don’t be a control freak. You might be tempted to dip your hand in all jars to check the temperature, just don’t overdo it. Having the ability to wear multiple hats doesn’t mean you have to do everything. There’s a reason why you have the managers and the rank and files in your team.

Your team needs a leader, not a goalkeeper. Let your team grow with your guidance, and let them decide on things that they can decide on. Soon, you won’t even have to check up that much since they are already better prepared for the task.

3. Don’t Seek Perfection

Nothing is ever completely perfect because cracks are where flowers bloom. So don’t let your experience become the ultimate standard of perfection, and allow your members to fall, get up, and grow on their own.

Just as you learn how to handle things inside your business, so do your men. Quality is one of the most important things in a business, but it doesn’t have to be perfect. Unless there is no growth, that is the time you have to seek other solutions.


4. Don’t Reject Feedback

If you are taking up multiple roles, you interact with several people in different capacities. So make sure to take feedback from each member to know how well you’re performing at each front.

One of the things that leaders often neglect is hearing criticism, even constructive ones. You’re not a know-it-all-jack-of-all-trades. You’re always bound to make mistakes as you’re just human.

Growth comes from learning from mistakes, whether from others’ experiences or your own mistakes. Take as much feedback as you can.

5. Don’t Say Yes to Everything

If you ever feel the urge to volunteer for everything, just run outside and return when you’re exhausted because that’s how you’ll feel if you keep saying yes.

Give equal time and attention to building a high-performing team so it can occupy your roles with time. Empower your people so they can replace you in tasks that don’t need executive involvement.


Then, you can utilize the saved time to do something more productive.

6. Don’t Wear Hats Simultaneously

You can’t be a creative and finance person simultaneously because each job has its unique needs and performance levels. Assuming multiple roles simultaneously will clutter your mind, confuse your judgment, and drop your productivity to the lowest.

7. Don’t Compromise Your Life

Wearing many hats is time-intensive, and there will come moments when you have to choose between taking that business call and going out to dinner with your family.

Choose what will make you happiest, because you can always earn back lost money. But you can’t retrieve lost time.

8. Don’t Compromise Your Health

It is tempting to do everything you like, but remember that the most excellent satisfaction comes from balance and well-being experienced in a healthy body and calm mind. If you’re a wearer of multiple hats, take time off at regular intervals to rejuvenate.

If it ever gets too much, don’t hesitate to take off a few hats. You can do your best only when you are at your best!


Wearing multiple hats means more involvement and more time to understand your own business. You are more aware of the business, and it becomes easier to solve things inside or outside.

Like a watchmaker, you have full control over the gears of your watch. It becomes easier for people to come to you, and they will. But you have to understand that there are downsides to this if left unchecked. As a business owner, your label is that of an executive, managerial, and employee. Knowing the right balance between different hats can help you alleviate these risks.


If you’ve chosen to lead different roles in the company, I hope this guide can help you do justice to your responsibilities.


Don't have time for the full article? Read this.

How To Stay Organized Wearing Multiple Hats In Your Business

Time Management: Having multiple hats means lesser personal time, overlapping tasks, and more task involvement. To be an effective leader, you have to manage your time wisely.

Eye for Detail: Wearing multiple hats requires you to have a good eye for detail, and one thing you’ll surely develop. To prevent issues from coming back, simple solutions won’t just do it. You have to look for the main problem.

Leadership: Being an effective leader means inspiring others and not simply forcing your people to do their job. Be accountable for your team and trust them to keep you accountable as well.

Efficient Workspace Organization: Since you have multiple hats, it’s important to have separation so you don’t lose track.

Keep Your Eyes Open: There are things that you have to look out for when wearing multiple hats. You have to accept that you don’t know everything and don’t have to be in charge of everything. Be open to mistakes, and accept criticism in your workplace. Don’t say yes to everything, and don’t wear hats simultaneously. And most of all, don’t neglect your personal life and health.

Featured photo credit: Clay Banks via unsplash.com


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