Advances in technology directly contributed to the rise of the freelance/independent contracting work. With few clicks, employers can today access a pool of skills globally. A mix of direct employees and contractors has become indispensable for starting, small, medium and large sized companies. On the other hand, independent contractors who by the way represent 34 percent of the workforce in the U.S. according to a survey conducted by Edelman Berland, enjoy the flexibility and wide reach that come with freelancing.

What’s the damage? Finding and hiring A Players is just the beginning. Training and supervision, alignment of interest, and accountability in freelancing, especially in startups, demand a few extra layers of attention and management. Here is how to hire and retain A Player freelancers?

Alignment Of Expertise

A little over 120 is the number of freelancers I interviewed and around 40 is the number of freelancers I hired over the past three years. Whether it is to build a stronger startup foundation, grow, or expand, I found that the best freelancers look for the experience and knowledge as much as the financial and flexibility benefits. Unless they are looking for a quick one time assignment, one of the discouraging factors for freelancers’ agreement to pursue the venture or commit long term is employer’s unrealism and/or lack of experience and expertise. An employer with the same level of expertise or higher is more likely to attract and retain freelancers with the same or lower level of expertise. Good freelancers are picky. Opportunities are everywhere and for this reason, it is not just about the money anymore.

I found that interest, commitment and respect increase when you show and prove the value you bring to the startup and to their career. Therefore, do not approach a top-rated freelancer with just a billion-dollar idea and a vision but also with how the opportunity will be of value to them. Yes, top rated freelancers take random jobs as well but do not expect a long-term commitment unless you provide them with an opportunity they are proud of adding to their resume and discussing with their friends and colleagues.

To hire and RETAIN A Players, be someone they look up to. 

Alignment Of Interest

Employers know their interests, what about contractors’? money is a universal motivator but certainly not the only one behind freelancers’ interest in your venture. There is only one way to know: ask. Chances are freelancers have different goals even if many of them are consistent with yours. I like to spend quality time listening to their objectives. It is common that the freelancer is perfectly fit for the job but their goals are completely different from the company’s that hiring will only mean the beginning of the end. One of my team member’s goals is to lead a growing startup IT division. Healthy growth is what almost every startup aims for and this member’s objective only means that he is going to go above and beyond to help the venture reach a growing point.

To hire and RETAIN A Players, founders must care about their goals and objectives as much as they do about the success and future of the startup.

Keep Them Busy

Freelancers, especially good ones, will not wait long before taking another job. Keeping them busy with constant work flow is one of the most important and yet challenging responsibilities of employers. Know your short-term goals and the resources and activities needed for the selected period, say a quarter. Do not hire unless you have enough work to keep them busy for a period longer than a month (unless, again, it is a one-time assignment). Divide work accordingly and keep in mind that it is better to start low in hours and increase progressively than the opposite. You can always keep them busy with paid training.

To hire and RETAIN A Players for the long-run, make sure you are prepared to keep them busy with constant work flow.

Freedom with deadlines

One of the perks of freelance work is the flexibility and freedom that comes with it. Most freelancers don’t work under direct supervision and no matter what software employers use to track work, it can be useless in a second if contractors decide to quit which they can do at any time. Trust is of utmost importance and I like to build trust by setting deadlines and leaving work time open for freelancers to enjoy the flexibility. An update, Q&A and frequent discussions are very important but when deliverables are dated, expectations are clear and compensation is fixed, you don’t have to worry about the number of hours or the time of the day they work.

To hire and RETAIN A Players, enforce accountability by setting deadlines not by tracking each fifteen minutes worked.


Assigning detailed and clear tasks is not sufficient. Making sure each member knows your strong belief in their skills and trusting that they will act responsibly and in their effectiveness is critical. Empowerment is so important that it can save you hundreds of hours in supervision and management. Foster open communication, set an example, encourage safe failure, clearly define roles and expectations.

A Players look for a chance to show their value. Fill them with energy by showing trust and belief while enforcing accountability in the action of each member including founders and managers. 


Good Job is sometimes a stronger appreciation gesture than money. Additionally, awarding uncommon and unexpected prizes such as the purchase of a new device, plane ticket, health insurance, and others beyond an increase in hourly rate can have a major impact on the motivation and retention of freelancers. The type of rewards will depend on their needs and for this reason and many others, learning the details about their personal and professional career will increase transparency not only in the work place but also in their recommendation of new talent and clients. They will become your ambassadors on the web.

The only common appreciation gesture is saying Thank You or Good Job. Everything else comes down to human needs. Listen and appreciate by what makes them feel appreciated whether it is a promotion, increase in hourly rate, vacation, insurance, etc.


The rise of the freelance economy transformed the way we work and do business. Research shows that 53 million freelance Americans contribute $715 billion each year to the economy. Because of the flexibility, access, and limited payroll that comes with freelancing, it is considered one of the most valuable employment forms for startups.

With many freelancers in the market, employers are faced with hiring and then retention challenges. A Players are freelancers who fit in the startup culture, share its vision, and go above and beyond to achieve goals and exceed expectations. To hire and retain A Players,

  • Be someone they look up to.
  • Care about their goals and objectives as much as you do about the success and future of the startup.
  • Be prepared to keep them busy with constant work flow.
  • Enforce accountability by setting deadlines not by tracking each fifteen minutes worked.
  • Fill them with energy by showing trust and belief while enforcing accountability in the action of each member including founders and managers.
  • Listen to their motivations and appreciate their work accordingly.

Freelancers, what would you add to the post? Employers, how else would you hire and retain A Player freelancers.

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