How Do I Talk to My Boss About Getting Hired On As A Full Time Staff?

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.


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[Photo: Flickr user WOCinTech Chat]

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?

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[Photo: Flickr user WOCinTech Chat]

Lolly Daskal is one of the most sought-after executive leadership coaches in the world. Her extensive cross-cultural expertise spans 14 countries, six languages and hundreds of companies. As founder and CEO of Lead From Within, her proprietary leadership program is engineered to be a catalyst for leaders who want to enhance performance and make a meaningful difference in their companies, their lives, and the world.

Of Lolly’s many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of The Most Inspiring Woman in the World. Her writing has appeared in HBR,, Fast Company (Ask The Expert), Huffington Post, and Psychology Today, and others. Her newest book, The Leadership Gap: What Gets Between You and Your Greatness has become a national bestseller.

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