Transitioning from a one-man army to a business owner of a company is no easy feat.

The benefits of scaling your business are endless: generating more sales and profits, reaching new customers and markets, reducing external risks (such as competition, market or technology changes) and more.

However, you’ll also face challenges when you expand your business. Here are some common challenges and solutions on how to resolve them.

[Entrepreneurship Tips] From Solopreneur To CEO - 3 Challenges & Solutions

Disclosure: Some of the links below are affiliate links. I will earn a small commission, at no extra cost to you, if you purchase through these links. Your support encourages me to continue blogging and help with the costs of hosting this site. Thank you!

Challenge #1: Growing Your Talent Pool

One of the top challenges that all companies face is talent acquisition.

You’ll need to grow your talent pool, both quantitatively and qualitatively, to scale your business.

But with thousands of companies in the industry, what makes your business special such that people want to join you?

In addition, recruitment is a two-way street. Both sides have to sell themselves. There must be something special about your business that will attract candidates. On the other hand, the ideal candidate will have to meet the job requirements and is a good fit for the company. He or she needs to be someone who can smoothly integrate into the company culture and the team.

Your human resources (HR) department will play a key role in this. They’re essentially the first people that your candidates meet, aka the face of your company. It helps if they’re a people person. Besides assuring your candidates and making them feel comfortable, a friendly recruiter also portrays your company in a warm light.

Photo by fauxels on Pexels

Solution: Highlight The USP Of Working At Your Company

Unique Selling Proposition (USP) is what differentiates your brand from your competitors.

Emphasize a unique perk of working at your company (along with the many other perks).

Here are some awesome perks that will keep employees happy:

  • Attractive Remuneration
  • Interesting or Meaningful Job
  • Well-Stocked Pantry
  • Chill-Out Lounge
  • Entertainment Corner
  • Nap Area
  • Free Breakfast/Lunch
  • Work From Home or Flexible Schedule
  • Team-Building Activities
  • Fitness Classes
  • Employee Discounts & Rewards
  • Employee Appreciation Gifts or Programs
  • Healthcare Insurance
  • Professional Development Courses

Do consider creating an employees benefits survey to find out which benefits are truly important to your employees. This will ensure that you don’t invest money into superfluous benefits that your employees don’t really need. You can also identify low hanging fruits that can easily boost your employee engagement with little to no cost.

Photo by Proxyclick Visitor Management System on Pexels

Solution: Showcase Your Company Culture To Attract The Right Talent

To recruit top talent who are constantly in high demand, you have to go beyond posting on job boards. Instead, you’ll have to take proactive steps to attract this talent. And this begins by showcasing your company culture.

Potential employees, especially the younger generation, are recognizing the value of a positive company culture. Some of them will prefer companies with positive working environment to positions with higher pay.

Photo by fauxels on Pexels

Posting behind-the-scenes content on your company’s social media channels is one great way to showcase your company culture.

These snapshots create transparency so prospective job applicants (and your clients) can see exactly how your company operates as well as the nuts and bolts of working for and with you.

In addition to images and videos that show how close-knit your team is, consider using a unique brand hashtag like #[companyname]life.

  • Team meetings
  • Company outings
  • Birthday meals
  • Attending events
  • Getting fit together
  • Enjoying team lunches
  • Volunteering together

Highlighting employees’ accomplishments is a great way to show your appreciation.

When the company praises its employees and celebrates their achievements, it shows that the company supports its talent in and out of the office. This calls attention to the supportive company culture that encourages employees to grow both professionally and personally.

No achievement is too big or small to sing praises. Your employee could have published a book, made an impact at a non-profit organization or exceeded expectations and delighted a customer.

Photo by fauxels on Pexels

Challenge #2: Moving From DIY (Do-It-Yourself) To DIT (Do-It-Together)

Most entrepreneurs are doing it all for their business, everything from production to marketing. Take me for example. I’m an indie author who does the writing, editing, formatting, publishing and marketing.

Likewise, an entrepreneur like you could be doing everything yourself. But as your business grows, there will be many customers and orders. You might struggle to meet this additional demand if you’re alone.

Hence, you’ll need to delegate tasks to other people to scale your business.

As the leader of your business, it is essential that you move away from execution and production and focus primarily on strategy so your business can thrive.

Photo by JESHOOTS on Pixabay

Solution: Learning To Let Go & Delegate To Your Trusted Team

To move from DIY to DIT, you’ll need to learn to let go and delegate tasks to your trusted team.

The key here is to trust your teammates and give them freedom. They’re also working towards the same goal as you. But with their expertise and creativity, they can bring new ideas and perspectives to the table. Together, you and your team can create an even better future for the company.

With your trusted teammates completing the tasks, you’ll have more time to think about strategic issues. This includes your company’s direction and future as well as the long-term vision. By setting a meaningful direction and building a strategic plan, you’ll lead your organization to growth and success.

Do consider delegating tasks that you don’t like doing or tasks that you aren’t good at. For example, I hire professional book cover designers since I don’t have any expertise in this area.

On the contrary, you might not want to delegate tasks that you enjoy or consider important. Writing is the core of my indie author business so this is definitely a task that I will never delegate to anyone else.

In addition to people, you can also rely on tools, software and technology. Email automation workflows will save you time and help you deliver a personalized experience to your customers. Most email marketing software like MailerLite or MailPoet will have this feature. You could also create a high-converting landing page (similar to a 24/7 salesman who converts visitors to leads) with tools like Elegant Themes Divi and OptinMonster.

Check out the 6 steps to mastering delegation.

Photo by fauxels on Pexels

Challenge #3: Lack Of Internal Alignment

In a one-person business, there will not be any arguments since you’re the only person who decides everything.

However, as more people join your company, there will be more opinions and perspectives which will lead to disagreements.

This isn’t a bad thing since disagreements are inevitable. In fact, they’re a normal and healthy element in all relationships. When managed well, they can lead to better work outcomes, opportunities to learn and grow, improved relationships and more.

Without the right processes and practices in place, you run the risk of misalignment. And nothing can be worse than a misaligned company.

In a misaligned company, everyone is divided. This is the exact opposite of what a company should be… united as one.

A company should be aligned in everything, from mission, values, culture, processes to technology. Everyone should strive towards the same goal and speak the same language.

The reality is that, more often than not, most companies are sadly misaligned.

Photo by Joël Super on Pexels

Solution: Set The Tone With A Positive Employee Onboarding Experience

Whether it’s an onboarding document, checklist or workflow, you need to have one for each department as well as the entire company.

The company-wide onboarding process should be unified so your new hires are aligned with your company’s culture and values.

Here are some onboarding ideas to get you started

  • Chat with the supervisor: elaborate on the company’s mission, values & culture
  • Mentor or Buddy: bring new hires around the office & introduce them to the team
  • Welcome Gifts/Swag or Onboarding Kit: make new employees feel at home (it doesn’t have to be luxurious; the key is to be thoughtful)

Check out the benefits of welcome kits for new hires as well as tips on creating effective welcome kits~

Photo by Tirachard Kumtanom on Pexels

Solution: Cultivate Company Culture & Bond Over Shared Values With Team-Building Activities

In my day job as a marketer, my company has a monthly Certification Day where everyone just drops everything they’re doing and focuses on learning. It’s a day where we take courses and achieve certifications (plus, free food!). All of us will learn similar marketing concepts so we speak the same language and are aligned across the various departments. This also reinforces the culture of continuous learning.

Similarly, you can conduct team-building activities to align your employees.

But first, you need to think about the purpose of the activity. What’s the culture or value that you want to reinforce? Be as specific as possible. From there, you can then narrow down the activities that would achieve your goal.

  • Escape Room: enhance critical thinking, require teams to strategically work together to crack the code
  • Two Truths and A Lie: allow team members to know each other better, help introverts mingle with others
  • Blindfold Challenge: build trust & collaboration among employees, enhance verbal communication

Photo by Helena Lopes on Pexels

Now It’s Your Turn

What challenges have you encountered in your journey from solopreneur to CEO? Do you have any tips or solutions to share with fellow entrepreneurs?

Check out online business classes and marketing and sales classes for more business growth tips. Or watch streaming broadcasts of free online classes at CreativeLive!


Copyright © 2017-2024
Nicole C. W. All Rights Reserved.

Want to receive updates?

Join My Newsletter Now


Be the first to know about hot new releases, tips from my blog and more.

Pin It on Pinterest

Share This