DON’T Hire A Team Until You’ve Answered These 5 Questions

Jenna Kutcher 

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August 23, 2023


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Feeling overwhelmed in your business? Not getting everything done?  It may be time to make your first hire.

I know how hard it is to ask for help, especially when our business is our baby. “I can do it all” was my mantra for YEARS… that is, until I was knocked to my knees in a devastating loss while trying to grow our family.

It was 2016, and on the same day that a doctor had delivered the worst news of my life, a virtual assistant named Caitlyn hit “send” on her fourth email to me, asking to help me offload some of the weight of running a business solo.

For me, it took the heartbreak of my second loss and acknowledging that I needed some time to be in the fetal position and not responding to emails to allow me to finally admit I needed help… but not without fear. 

I had never hired anyone before. Not only was I afraid to have someone see just how unkempt and frankly embarrassing all my systems were (I had like fourteen spreadsheets labeled the same exact thing), but I was also afraid of being someone’s… boss? 

Being “in charge” of my own business was already a lot of work, but owning the responsibility of actually caring for and providing a paycheck for an employee petrified me. From her emails, I could tell this person was a treasure of a human and would make an incredible virtual assistant.

She came across as confident, tenacious, and somehow so very warm all at once. So, what would happen if I brought her in and royally screwed everything up because I just wasn’t ready?

But when I finally ‘bit the bullet’ and brought Caitlyn on, the only word I can use to describe the feeling was complete and utter relief. I was finally not ‘doing it all’–I had someone to help me, and to brainstorm with.

Since that fateful day in 2016, I’ve given birth to two healthy baby girls and built a team of 12 employees and subcontractors that I care so deeply for.

So whether you’ve been hesitant to ask for help in the past or are already a firm believer in the value of collaboration, this episode aims to expand your perspective and help you determine  if it’s time to make your first or next hire as an entrepreneur. Because although I’m a firm believer in asking for help, I also don’t want you to jump in ‘blind’.

So without further ado, here are the 5 questions you NEED to ask yourself before making your next hire. 

1. Is my workload overwhelming?

Assessing the volume of work you’re currently juggling is essential for maintaining a healthy work-life balance and ensuring you can effectively meet your goals. If you find yourself constantly stretched thin, struggling to meet deadlines, or unable to focus on strategic business growth, it’s a clear indicator that your workload has reached an overwhelming point.

Picture this: you’re working long hours, pulling all-nighters, and still barely scratching the surface of your to-do list. Your energy and focus are spread thin across multiple tasks, leaving you feeling drained and unable to give your best effort to any one thing. It’s like trying to hold up the weight of the world on your own shoulders.

Recognizing the signs of an unmanageable workload is crucial. Not only does it impact your personal well-being, but it can also have adverse effects on the quality of your work and the success of your business. You might find yourself making avoidable mistakes, missing out on important opportunities, or experiencing burnout. These are clear signals that something needs to change.

Plus, bringing someone on board can provide fresh perspectives, new skills, and diverse expertise that you may not possess. It opens up the possibility for collaboration and teamwork, fostering an environment where ideas flow freely, and productivity soars.

Remember, it’s okay to ask for help when you need it. Recognizing when your workload is becoming unmanageable and taking proactive steps to address it is a sign of strength, not weakness. So, be kind to yourself, prioritize your well-being, and empower yourself and your business by sharing the burden with someone who can contribute to your growth and success.

2. Are there tasks I’m not equipped or skilled to handle?

When it comes to running a business, recognizing your strengths and limitations is key to achieving success. It’s important to consider the specific tasks or areas of expertise required for your particular business. After all, no one can be an expert at everything.

Take a moment to reflect on your own skill set. Are there certain tasks that you find challenging or time-consuming? Are there areas where you lack the necessary knowledge or experience to complete tasks efficiently? If the answer is yes, it’s a clear indication that you may need to make your first hire.

Let’s say you’re running a marketing agency, and while you excel at developing creative campaigns and crafting compelling messages, you might struggle with the technical aspects of website design or the intricacies of SEO. Instead of spending hours researching and trying to master these skills yourself, it makes more sense to hire someone with the specific expertise to handle those tasks (because remember… your time is money)!

By bringing in someone who can fill the gaps you’re not skilled at, you not only save yourself time and effort but the job will also be done to a higher standard. When you have someone who knows the ins and outs of a particular task or area, they can deliver better results, provide valuable insights, and stay up-to-date with the latest trends and best practices. This level of expertise can make a significant difference in the quality of your work and the overall success of your business.

Moreover, outsourcing tasks that fall outside your skill set allows you to focus on what you do best. It frees up your time and mental energy, enabling you to concentrate on the core aspects of your business where your expertise truly shines. This, in turn, can lead to increased productivity, better decision-making, and ultimately, business growth.

Remember, recognizing the tasks that are outside your expertise and seeking help is not a sign of weakness. It’s a strategic decision that empowers you to deliver better results, save time, and focus on what truly drives your business forward. So, embrace the opportunity to collaborate with experts and watch your business thrive!

3. Can I afford to hire someone?

I’m a huge advocate for not biting off more than you can chew, and in order to ensure you can afford to hire someone, you may need to work with an accountant or financial advisor to determine if you can hire someone. They’ll help you consider not only the salary but also additional costs like benefits, taxes, and training.

Before you go out and find a VA or graphic designer or someone else, be sure to assess your cash flow and projections to ensure that hiring someone won’t strain your finances.

I know hiring someone to share the burden may seem like an extra expense or a daunting task in itself. But think about it as an investment in your own sanity and the growth of your business.

By bringing in additional help, you can redistribute tasks, delegate responsibilities, and free up your time and mental energy to focus on the bigger picture. It allows you to prioritize strategic business growth and creative problem-solving instead of constantly firefighting.

Also, keep in mind that hiring someone with specific expertise doesn’t necessarily mean hiring a full-time employee. Depending on the nature of the task, you might explore options like freelancers, consultants, or agencies that specialize in the area you need support in. This gives you the flexibility to tap into the required expertise on an as-needed basis, without the long-term commitment or overhead costs associated with a full-time hire.

When seeking help, be clear about the skills and knowledge you’re looking for. Take the time to evaluate candidates or service providers, reviewing their experience, portfolio, and client testimonials. It’s important to find the right fit for your business and establish a working relationship built on trust and effective communication.

4. Are there repetitive or low-value tasks that could be delegated?

As a business owner, it’s crucial to identify tasks that are important but don’t necessarily require your direct involvement. These tasks can range from administrative work like scheduling appointments and organizing documents to data entry, customer support, or even social media management!

While these tasks are essential for the smooth operation of your business, they may not be the best use of your time and expertise.

Think about it: as a business owner, your time is a valuable resource. You have unique skills, knowledge, and strategic vision that drive the growth and success of your venture. Spending excessive time on tasks that could be delegated or outsourced can prevent you from focusing on higher-value activities that truly move the needle.

Let’s take customer support as an example. While it’s vital to provide excellent customer service, spending hours every day addressing customer inquiries or troubleshooting issues may not be the best use of your time, especially if your expertise lies in product development or business strategy. 

By hiring a dedicated customer support representative, you can ensure that your customers receive prompt and professional assistance while freeing yourself up to concentrate on tasks that directly impact business growth.

Similarly, sometimes social media, administrative work, and scheduling appointments are important but time-consuming tasks that can easily be handled by someone else. Hiring an administrative assistant or virtual assistant can help you streamline your day-to-day operations, manage your calendar, and handle routine administrative tasks, allowing you to focus on critical decision-making and strategic planning.

By delegating these important but time-consuming tasks to competent individuals, you not only free up your own time but also benefit from the expertise and efficiency of those who specialize in these areas. They can bring fresh ideas, stay up-to-date with the latest trends and best practices, and ultimately contribute to the overall success of your business.

Remember, by delegating tasks that don’t require your direct involvement, you’re empowering yourself to focus on high-value activities that leverage your unique skills and drive your business forward. So, embrace the opportunity to build a capable team and watch as your productivity and business growth soar.

5. Am I missing out on growth opportunities?

Evaluating your current workload is not just about managing the tasks at hand; it’s also about assessing the impact on your business’s growth potential. When you find yourself turning down potential clients or projects due to a lack of capacity, it’s a clear indication that your workload is hindering your ability to seize new opportunities and expand your business.

Imagine this scenario: you’re a graphic designer running your own studio. You have a steady stream of clients and projects, but as your reputation grows, more opportunities come knocking at your door. However, due to your limited capacity, you’re forced to decline these potentially lucrative projects. It’s frustrating to see the potential for business growth slipping through your fingers.

This is where hiring someone to help becomes essential. Bringing on additional team members enables you to take advantage of these growth opportunities and capitalize on the demand for your services. By expanding your workforce, you increase your capacity to take on more clients, tackle larger projects, and enter new markets.

Plus, hiring someone to share the workload allows you to provide better service to your existing clients. With more hands on deck, you can ensure timely project delivery, maintain high-quality standards, and nurture stronger client relationships. Satisfied clients often translate into repeat business, referrals, and an enhanced reputation, all of which contribute to the long-term success of your business.

Do keep in mind, though, that it’s crucial to strike a balance. Hiring someone solely to address your current workload without considering the potential for growth might not be the best approach. Instead, focus on finding someone who can handle the immediate demands while also supporting your expansion plans.

Look for individuals who possess skills and experience that align with your growth objectives, as they can contribute to both your current workload and future endeavors.

By strategically hiring to meet both immediate and future needs, you can position your business for sustained growth. It’s an investment in your own capacity and potential. With a stronger team in place, you can confidently pursue new opportunities, take on more ambitious projects, and explore untapped markets.

So, take the time to evaluate your workload, assess the potential opportunities you’re turning down, and envision the future growth of your business. Hiring someone to help you capitalize on those opportunities not only alleviates your immediate workload but also sets the stage for a more prosperous and expansive future. Embrace the possibilities, and let your business reach new heights!

Building a team is a significant decision, but it is SO empowering when you finally make your first hire. Working with women all over the country to serve business owners like you has been one of my greatest joys as an entrepreneur.

I hope this episode helped you identify whether or not it’s time to make your first hire! 

Thank you to our Goal Digger Sponsors

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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