How Do I Talk To My Boss About Getting Hired On As Full-Time Staff?

Here are the steps to take in order to build a compelling case to make the transition from freelancer to salaried employee.

How Do I Talk To My Boss About Getting Hired On As Full-Time Staff?
[Photo: Flickr user WOCinTech Chat]

There are over 54 million people freelancing in the U.S. , and that number likely includes a lot of people who are working freelance full-time for just one company. But if you want to become a salaried employee with benefits, making your case to the boss can be intimidating.


This week, leadership coach Lolly Daskal helps a reader figure out how to have that difficult conversation.


I was brought on as a full-time freelancer about eight months ago. I’m good at my job and want to stay with the company, but I really want a salary and benefits. The security would feel nice, but one major concern is that I’m turning 26 and will soon lose my health insurance coverage under my parents’ plan.

My company employs lots of full-time freelancers at any given time (I’d estimate that share is about a third of our staff), many of them for anywhere between a few weeks to more than a year. When I was hired, there was never an explicit understanding that I could eventually be brought on as a salaried staff member, so I’d need to plead a really compelling case to get my employer to make an exception.

It will be another four months or so until my performance review. At this point I don’t feel like I have much leverage, aside from a solid track record of good work. Any tips on how to discuss this with my boss sooner rather than later?

To achieve the transition you want, you need to build a compelling case. Here are the steps in that process:

Do your homework. The fact that you are already working there is great, because it gives you access to inside information. How many full-timers are on staff? Is there a precedent for creating a new position, or will you need to wait for someone to leave? Does hiring for full-time positions tend to come from within the freelance pool, or outside? Who makes decisions about staffing and hiring? You may not hear what you want to hear, but at least you’ll know where you stand.

Assess your value proposition. Know your strengths and assess your value proposition to the company; think of reasons why they should hire you. Take note of the ways your strengths and talent make a difference in the company, and how you could magnify those benefits from a full-time position. Know what differentiates you from the rest, and how can you make a purposeful difference.


Always have a positive attitude. People always remember those who have a positive attitude and how good they feel around that person. You don’t have to be perky, but make a point never to complain, and to be positive in your interactions with everyone in the company.

Make yourself indispensable. Work extremely hard and do a great job every single time. Become the person that others know they can rely on. Set a goal of being not just the best freelancer of those around you, but the best who has ever worked there. Make yourself so indispensable that others will look for a way to keep you around. Be memorable. Become the person who shows up early, who helps others when they need it, who offers to take on more, and does it all without complaining. Be a great listener and a great helper.

Become a team member. Make connections and build relationships to become regarded not as an outsider but as part of the team. Go out to lunch with people, or stop by their desks for a moment to stay engaged and connected. Show that you’re a good fit for the company’s culture.

Make your case. If you know for sure that this is the job you want and you’ve worked through all the above steps, make your case. With luck, they’ll hire you right away—but even if not, you’ll be well situated for the next opening. Good luck!

If you have a dilemma you’d like our experts to answer, send your questions to or tweet a question using #AskFC.


About the author

Lolly Daskal is a Leadership Development and CEO coach and consultant and founder of Lead From Within. Follow @LollyDaskal.