First Employee - Solopreneur to Entrepreneur

February 22, 2024 •

Entrepreneurship is a difficult path with unique challenges to overcome. Let’s dive into the nitty gritty of it using my experience in this journey;


I have learned a lot in my twelve years of hiring and firing employees. It is hard going from zero to one, and it’s the same for hiring.

Hiring is a challenging task that requires a lot of time, patience, and discernment. I get so much done while simultaneously working less.

We have eight fully contracted employees and three freelancers working for us. Metrics show we accomplished twelve times more than previously when I handled everything.

Everyone we’ve hired focuses their time and energy on their expertise, and more work gets done. I’ve learned the intricacies of hiring from experience, and I hope you can learn them without making the mistakes I made.

Manage your Expectations

I set clear, and realistic targets to ensure new hires understand their roles and responsibilities. This fosters a positive and productive working relationship.

I openly communicate with them and discuss performance goals, project timelines, and company culture. Regular check-ins and performance evaluations allow for continuous feedback that enables needed adjustments.

This creates an environment where your employees feel empowered, motivated, and equipped to succeed.

You’ll Outwork Your Employees

This is the case when building your start-up. No one will love and cherish it more than you. You’ll work long hours, doing more than anyone else to guarantee success.

Hiring the right personnel helps you build your start-up faster, but you can't expect them to work as much as you. Some employees only work for the paychecks. The right people will give you consistency and quality work that propels your start-up to new heights.

No one gains as much as you do when your start-up succeeds. Doing more than your employees will happen numerously.

This lessens the load on your shoulders, having you work less while achieving more.

Be Patient with Losses but Set a Limit

I establish limits that prevent losses from escalating beyond a manageable point. I communicate these limits transparently to my employees to foster accountability and responsible decision-making. The balance between patience and setting boundaries supports the development of a resilient workforce that can adapt, learn, and evolve while safeguarding your organization's stability and goals.

Failing is part of learning. It is expected during your entrepreneurship. This may be yours or your employee’s. Remember, failure is part of learning.

I mitigate risks by hiring employees on a trial basis to gauge their skill level. I hire people for four weeks, which gives me enough time to assess how well they work unsupervised, how well they work with others, and the quality of work they produce.

I have them complete specified objectives to sufficiently evaluate their skills and see if they can fulfill their responsibilities. This saves time and money, mitigating losses in the process.

Learn to Collaborate

Collaboration between you and your employees is crucial to get things done. Your employees will view you differently as their "boss." Therefore, guard your speech and carefully pick your words when communicating with them. Avoid stepping on their toes or doing something that makes them uncomfortable.

I can’t joke about firing an employee. I might be pulling their leg with such a joke, but from their point of view, it is viewed as a potential threat to their livelihood. I am in a position of power as their boss.

Your employees feel obligated to be responsive to your friendliness. Keep these friendly interactions cordial without crossing over to flirting. This aspect is crucial in male-female dynamics. Be mindful of how you are with your employees, maintaining cordial but respectful interactions to foster trust in your organization.

This accelerates the growth of your employees and the maturation of your organization.

Be The Pawn to Become the King

My worst experiences with new hires have involved hiring them without understanding how to do the job I hired them for. I could not measure the quality of the work they did. Therefore, I try to do the thing that I am hiring for before hiring. This gives an easier time evaluating your employees’ output and structuring their work. This helps you create realistic goals for your employees and teaches you what to look for in employees who do not work as well as required.

Who to Hire

Choosing who to hire depends on what your company needs. You can hire a writer, a front-end developer, a back-end developer, a tester, or a Google ads expert.

Hiring for the specific role has been the easiest for me. I try to follow these criteria;

Hurt: These roles do not hurt physically. They can be roles that are annoying for you. Minimize this by hiring someone qualified to handle this role, freeing you to handle other tasks.

Time-Consuming: These consume your time. Hire qualified personnel to handle these roles. This frees you to handle other tasks that maximize your time and resources.

Easy to Hire/Train: These roles can be filled by employees trained for short periods or employees lacking extensive skills. There are minimal risks involved with hiring for these roles, and they yield free time for you to handle other pressing tasks.

The more the hire fits these criteria, the better. I avoid hiring someone to solve all my problems as this is usually a recipe for disaster.

Inspirations for Hiring Employees

Example 1

Hiring a full-stack developer is difficult and expensive. The difficulty finding one is matched by how expensive acquiring their services is. It’s better to evaluate your needs than make the hire that fits.

You could hire a front-end developer or a back-end developer. CSS/HTML may be the most time-consuming for you, but it is also one of the lowest-skilled positions to hire for. Hiring someone to handle CSS/HTML, thus saving you time and money.

Example 2

A marketing strategist might be out of your expenditure range, and it may be hard to gauge their skill level. Instead, you can hire someone to do Google Ads or Facebook Ads to handle your marketing needs.

This hire will have marketing skills and ad expertise to handle the needed marketing, saving you time and money.

Example 3

It costs a lot to hire an SEO strategist. You can hire a blog writer instead who will perform the same role and give you what your company needs. You will have to figure out a little about SEO and how to drive traffic, but it is a lot easier than hiring someone hoping they can do it all.

Blog writers usually have sufficient SEO knowledge and create content, making them an ideal option for this role.

Example 4

Social media is time-consuming. Hiring a VA to handle social media engagement and giving them some advice is usually easy. You can hire a knowledgeable person and educate them to perform this role.

Where can you find candidates?

There are many places where you can find potential candidates. Some good examples are;

  • Upwork
  • Fiverr
  • Social media (Twitter/ X worked wonders for us)
  • Local forums
  • Reddit Forums

You can find employees who can work remotely, but remember to factor in time zones. If possible, prioritize hiring employees who are within your time zone.

I went into detail about hiring QA in another article. You can read more on this here. [Hiring QA]

Hiring Process

The goal is to hire someone who can step in and immediately solve problems. Finding this person can be challenging, but here are some ideas to help you.

Simple interviews

Interviews offer a way to learn more about your potential hire. Interviews give insights that cannot be seen on CVs.

Make the interview format simple. Ensure the potential hires understand you and vice versa. Do not put a lot of weight on how well the interview goes. Many of our best interviews produced terrible employees for us, and we had to fire them.

We’ve had two mediocre interviews that gave us two of our great employees. Take time to read your potential hires and make sure they are trustworthy. Give them tasks within their job description as an extra assessment tool to gauge their skill level.


Some of my best hires have been referrals from friends. I still maintain caution when hiring referrals. Have an exit strategy readily available in case things do not work.

Create clear objectives for them, letting them know what is expected. This saves you a lot of time and resources that would otherwise be wasted on redoing tasks or correcting errors and subpar work.

Trial Hiring

I am a big proponent of what I call trial hiring. I hire people for a trial period and assess their output.

I work with some on Saturdays for 5-10 hours for one month to gauge their skills. I do this for all potential hires that are contracted to another company. This way, I can assess whether they’d be a perfect fit for my company.

This method has worked best for me.

Working Together

Working together allows me to gauge their skills and intangibles. Examples of intangibles are work ethic, drive, motivation, problem-solving, etc.

These are things that can only be assessed by working close to someone.

Countless books have been written about this, and we are making juicy blogs about it, which is reason enough to subscribe to our newsletter in the right sidebar.

Set Standards

Set high standards for yourself, your employees, and potential hires. These standards ensure your company maintains the highest quality in all work and tasks.

We have set high standards for ourselves. We have made the following document to help you do the same. How We Do Software

An example of our high standards involves proper time management. We value our time, and people who aren’t punctual aren’t kept around. We are very vocal about it, obliterating any possibility of a misunderstanding.

Many people are deaf to hints and require explicit facts on how they aren’t performing as expected. Be direct with them, letting them know what they did well and what they did not.

Micro-Manage in the beginning

I micro-manage my hires, especially in their first days at the company. I communicate this to them before they start working for me. I do this to help easily onboard them and give them more responsibility in the future.

The more responsibility I give them, the less micro-managing they will need, hence the more work we get done. I complete this process in three months, showing them everything they need to know.

This process is crucial in integrating your employees into your company and how it works.

For example, I recently hired a writer whom I am giving a lot of feedback and writing detailed dispositions for than I usually would do. The idea is to slowly relinquish my responsibility by giving him the responsibility of creating content ideas and dispositions for me to approve or disapprove. He can then create texts for the dispositions I approve.

I should be spending less time on this in three months.

Chose Talent and Ambition

I recently hired a Quality Assurance (tester), and he did very well. He mentioned that he knows how to use Photoshop, and we had a task related to Photoshop. He completed this task, performing beyond our expectations.

He recently started using Figma to create designs for our new revolutionary project management tool. He is responsible for our video editing as well.

People will surprise you, especially if you listen to what they like to do. We have an asset working for our company. Talent will only take you so far but will move mountains when paired with ambition.


Collaboration is the next logical step. You’ll work in tandem with your employees to achieve common goals. Proper communication and collaboration are necessary to make things work. We have a project management tool that facilitates this. It will be useful to you at the start when you have to make sense of time spent. Goleko has a time app that allows for time tracking. It also generates time logs that you can use to create invoices or pay billable hours. You can also give video recordings as feedback for the tasks and projects. These are some of the many features you will have with Goleko. They’ll improve your productivity and enhance the efficiency of your work and employees.