A Business Owner’s Guide to Wearing Multiple Hats


FACT: running a business can be hectic and overwhelming. As the business owner, you often have to take on the roles of CEO, salesperson, receptionist, and more at any given time. It’s no wonder then, that 62% of business owners work longer hours and 42% report feeling overwhelmed.

But here’s the good news: there are a number of steps you can take to reduce overwhelm and better manage the multiple “hats” that you’re wearing. 

That’s exactly what we’ll cover in this article. You’ll learn how to:

  • gain clarity into the different “hats” or roles required to make your business work;
  • delegate responsibilities effectively so you can focus on doing more of the things you love;
  • leverage technology to streamline your business processes and save time.

Let’s get started!

1. Start with a vision

First, take a high level view of your company and your objectives. Why did you start your business? What do you want to achieve? Having a clear and compelling vision gives you a sense of purpose. It helps you unlock the drive and grit you need to consistently show up and do good work—something that’s crucial to running a successful business. 

Industry data supports this. A survey by TD Bank found that more than two-thirds (76%) of small business owners reported that envisioning their business goals helped them get to where they are today.”

On a more practical level, a vision also solidifies your objectives, which then helps you figure out the steps you need to take to achieve them. That same study by TD Bank found that 63% of small business owners believe that visualizing their goals helps them map out and create their business plans.

Once you have a clear vision in mind, you can work backwards to determine the necessary “hats” or roles you must take on to meet your objectives.

For example, if you envision having a modern toy shop that serves customers all over the country, then you can start identifying the components required to make it a reality. That could mean:

  • Finding suppliers from whom to source unique products
  • Setting up ecommerce site so you can serve customers no matter where they’re shopping
  • Merchandising the shop to showcase products in the best possible way
  • Creating a strong social media presence that encourages people to engage with your brand

All this to say that having a solid vision is a key component of entrepreneurial success. It gives you clarity and empowers you to take the steps you need to create a thriving business. 

2. Iron out the “why,” “what,” “when” and “where” for each of your responsibilities

Once you know the various tasks you need to take on, identify the responsibilities of each role and what success looks like when you’re wearing a certain “hat”. Map out when and where you need to take on various roles and block out days and times for each. 

For example: 

  • Weekday evenings are for reconciliation and bookkeeping
  • Monday mornings are for strategic planning
  • Friday afternoons are for staff meetings and development

For best results, batch similar roles and do them at scheduled periods. That way, you know what you need to be doing at any given time and you’re less likely to get pulled in other directions. 

Batching tasks is a method that’s proven to increase brain focus and productivity. As Dr. Sahar Yousef, Cognitive Neuroscientist, UC Berkeley points out, “The human brain works best when it focuses on one thing at a time. We have a certain amount of cognitive capacity and a certain amount of attention.”

Let’s say you’re looking to create social media content so you can publish Instagram posts twice a day. Rather than taking time off each day to create content, consider blocking out half a day (or a whole day depending on your needs) dedicated to creating social media content, then scheduling them in advance. 

In doing so, you can get a week’s worth of work done and won’t have to spend too much time each day thinking about what to post. This saves you time throughout the week, which helps you put more focus on other tasks. 

3. Delegate if possible

You may need to wear multiple hats, but you don’t have to wear all of them. Identify roles and responsibilities that you can delegate, so you can focus on the things that only you can do. 

Let’s say you’re running a restaurant and you’re the face of your company. You’re at your best when you’re talking to your customers and interacting with the community. 

With this in mind, you may choose to focus more of your efforts on customer and community-facing roles that put you on the restaurant floor rather than in the kitchen and backoffice. 

In order to make that happen, you decide to hire more chefs, dishwashers, and bussers to keep the behind-the-scenes of your restaurant running, while you focus on keeping diners happy. 

That being said, before delegating tasks, ensure that your procedures are well documented and repeatable. For every task that you assign to a team member, see to it that detailed steps are outlined in a database or document that employees can access whenever necessary. This makes it easier to hand off processes to your team.

Another key step to make delegation a success is to ensure your team has the support they need to do their jobs well. The last thing you want is to have everyone running to you when there’s a problem that needs to be solved. 

An effective way to ensure your team members are supported is to choose vendors and technology partners that have strong customer service offerings. 

Case in point: The burger chain Five Guys struggled with an inefficient POS system and inadequate support from its tech provider. 

“Customer service with Oracle MICROS was a big issue for us. We spent countless hours on the phone. The whole system would be down and we couldn’t reboot, so when we faced major issues, we had a tremendous loss of sales,” recalls Aubert Prévost, president at Koeppel Companie.

So, Five Guys decided to switch to Lightspeed to modernize its operations and access a dedicated team member who can look after the company’s account. This proved to be incredibly beneficial, and has helped team members across multiple locations to work more efficiently and serve diners better.

With Lightspeed’s reliable system and 24/7 support, Aubert said they’ve been able to handle issues as they arise instead of opening support tickets and losing crucial transaction time. 

“I’m very grateful to have our Lightspeed agent,” says Aubert. “He’s assigned to us—which is something we would never get with MICROS. When I send him an email, he responds right away.”

“The Lightspeed team including the customer service specialist and developers have helped us build our business to what it is now with ease,” he adds.

4. Use tools to facilitate workflows and automate tasks

Do yourself and your team a favor and leverage digital platforms (like Lightspeed) that can help you manage your operations. That way, you can spend less time wearing your “admin hat” and devote more energy to high-level responsibilities, such as strategy, team development and business growth. 

The right solution will depend on your needs. A good way to determine which tools to adopt is to identify pain points and areas of inefficiency in your business. 

Let’s say you’re constantly running into stock control issues and discrepancies. Having a robust inventory solution can help you better manage your stock. 

Take for instance, Exclucity, a shoe retailer with 7 locations across Canada. As a footwear retailer, Exclucity needed to have multiple sizes and styles stocked at any given time. The team always had a lot of back and forth between the sales floor and the stockroom. To keep things running smoothly, company founder Trend Hall used Lightspeed to manage his inventory and business operations. 

This enabled Trent and his team to have an overview of all Exclucity locations, empowering them to transfer and organize stock in real time. Lightspeed eliminates the stress of having to manually track and manage inventory across multiple locations, thus freeing up time and resources for Trent to focus on high-level tasks in the business. 

“Lightspeed is actually like your most important employee because it’s managing your entire business for you. Now I know I can focus on what Exclucity is going to look like in 5 to 10 years,” says Trent. 

He continues, “I don’t have to worry so much about the day-to-day and it’s great because it’s a system. Twenty-four hours a day, 7 days a week [Lightspeed is] watching over your business for you. It makes me feel comfortable.”

Exclucity perfectly demonstrates how the right tools can help you run a growing business without getting overwhelmed. Like Trend, aim to find a robust platform that can take tedious tasks off your plate, so you can focus more on other areas of the business. 

Also, remember that adopting digital tools is only the first step. Apps work best when they’re connected to solutions, so find ways to integrate your systems to further streamline your workflows. 

For instance, integrating your POS with your payment processor reduces double-entry and manual reconciliations to save you and your staff time. 

Consider the case of Blazers & Bottoms, an apparel retailer in Columbus, OH. Storeowners Alysia Jackson and Janette Horton chose to launch their store with Lightspeed’s all-in-one commerce platform which included a robust point-of-sale and payments solution. 

This meant that their POS system and payments terminal are tightly integrated, which paved the way for a smooth customer experience.

 “Everything is so self explanatory. You just tap and it comes up immediately. Or you just put your card in, remove it, and the system processes it very quickly,” says Janette. “It’s part of the whole customer service experience. You want them to be comfortable with everything; not just the shopping, but with the whole checkout experience as well,” she adds.

Beyond the checkout process, Lightspeed Payments also helped them streamline back office tasks, as well as access useful reports and analytics. Alysia loves that she can see the right metrics immediately, and that she doesn’t have to manually calculate or find data on pricing, margins, and profitability. 

“The reports are available at a glance. Plus, you can add columns and personalize them to what you want to see.”

Janette and Alysia are the two main people in charge, and there are only so many “hats” they can wear. That’s why having a tightly-connected platform is so beneficial. Connecting their various solutions eliminates cumbersome admin work, which ultimately frees up more time.

5. Measure your efforts and results

Everything that we’ve discussed so far—i.e., figuring out what hat to wear, delegating responsibilities—are tasks that aren’t set in stone. The business landscape is always changing, and you will need to adapt. 

That’s why it’s essential to keep an eye on your business data and reports. Regularly measure your performance in different areas, including sales, customer engagement, stock control. 

Lightspeed’s advanced reporting capabilities put crucial data and insights at your fingertips. You can customize your reports so whether you want to get a high-level view of your business or want to drill down on a specific metric, you can do so with just a few clicks.

You should then use those insights to inform your business decisions. For instance, if sales are stagnant, then you may need to wear your sales or marketing hat more often—or hire someone who can take on those responsibilities.

If everything is tracking well, perhaps it’s time to put on your visionary hat and strategize what’s next for your business.

Whatever the case, you can’t make smart business decisions without the right data, so ensure that you have a system that allows you to monitor your performance and extract actionable insights. 

Final words

Running a business can be tough and entrepreneurs often have multiple balls up in the air. That’s why it’s important to have the right people and solutions that can help you wear multiple hats effectively — and with style. Get in touch with Lightspeed and discover how our tools can help you streamline your business and make your life easier.

About Francesca Nicasio

Francesca Nicasio is Vend’s Retail Expert and Content Strategist. She writes about trends, tips, and other cool things that enable retailers to increase sales, serve customers better, and be more awesome overall. She’s also the author of Retail Survival of the Fittest, a free eBook to help retailers future-proof their stores. Connect with her on LinkedIn, Twitter, or Google+.


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