Working for a family friend is great, except now I need a raise

The backstory: 

I need help negotiating a raise with my boss - who is also a very good family friend. I started working with her right out of college, and the hourly rate she offered me was a good start for someone going into the workforce! But now, over a full year later and saddled with health insurance and car payments, it's clear to me that what I'm being paid isn't a livable wage anymore.

How do I begin the conversation? She's known me basically my whole life, and I feel a little uncomfortable asking her for more because I know the company isn't a huge profit maker. But I also know I have to make some changes concerning my income soon, or else I'll have to find another job. Any advice on how to get the ball rolling?

— Dorie, Los Angeles

Alex's Advice

I understand how this feels like a tough spot. My guess is that when you agreed to take a job from a family friend, you must have had some idea that this day might come. Now you'll have to decide whether to ask for more or look for something else. You mentioned your company isn't "a huge profit maker," but if you are going to make the case for a raise, it shouldn't be based on your company's profits — or your living expenses, for that matter.

There are two questions you should ask yourself.

1. Why me? Can you make a strong case for why you deserve a raise? What evidence can you share to back yourself up? Strong evidence has three components: value you’ve created for your team or company, value you’ve saved for your team or company, and your superpower — your unique strengths that come to you effortlessly and naturally.

2. Why now? Strike while the iron is hot. The iron is hottest when you’ve recently accomplished something great or rescued your team from hot water. Your performance review is another good time to ask, as long as it’s not completely divorced from the budgeting cycle. (If budgets are finalized before review season, waiting until review season may not get you very far.)

Finally, if you catch yourself making excuses to avoid asking for a raise you know deep down that you deserve, ask yourself this: how much am I willing to pay to avoid an awkward conversation?

— Alexandra Dickinson
CEO + founder

Ask Alex is our monthly advice series. CEO + Founder Alexandra Dickinson answers your most burning negotiation questions. Subscribe to our email list for more advice and content. We'd also love to hear from you! Submit your questions to


Alexandra Dickinson

Alexandra Dickinson is the CEO and founder of Ask For It, a boutique consulting company working to close the gender wage gap by effecting change at both the institutional and individual level. We work with companies, schools, organizations and individuals through a combination of trainings, workshops and consulting. Our goal is for women and men to be paid based on their talents and skills, regardless of gender, and for our company to have been an important part of that change.