Original Illustration by Stephanie DeAngelis
Whether you’ve just figured out what you want to do with your life at the age of 40 or know exactly what you want to do and have been doing it for a decade, a little career advice—from how to find a job to how to handle an exit interview—couldn’t hurt. Especially if it’s coming from someone who is at the top of her field and has been there, done that, or one who specializes in navigating strategies to get both your top job and top salary. Career Contessa, an online career development platform for women, is now offering just that through its new Hire a Mentor program. But before you spend your hard-earned (or soon-to-be-earned) cash for a one-on-one session ($75 to $179 for 50 minutes), we had three real women* try out the service’s mentors to find out exactly what to expect.
*Names have been changed to protect these women’s working relationships.
Situation: Valerie, 28, is currently working as a senior editor at a digital media company while searching for a staff writing job in television.
Session (with Career Contessa mentor and job search consultant Jaime Petkanics): “I had low expectations. I expected it to be cheesy and to hear things I already knew. But first of all, I really liked Jamie. She was a very nice and engaging person to talk to. She had me tell her about myself, which was easy in terms of what I was trying to do professionally. I felt very in control of the conversation.
“The most surprising thing I learned was when you think about searching for jobs, you think about your résumé and reaching out and applying. But one thing you don’t think about is the exit interview. If you’re talking about finding a new job, you’re also talking about leaving one. Should you be super honest? Or weary and diplomatic? She said while it’s anonymous, the company can put two and two together and figure out who you are. You don’t want to leave things on a bad note, because you need them for references. She was also very helpful in recommending I punch up my LinkedIn with links to what I’ve done. She pointed out that I’m in a position where I can illustrate my work. We also talked about how to approach a cold email to a new company. Specifically, if you sound overly formal in your reach-out, the person is probably not going to read it. She said you should have personality in your cover letter, but for the most part, people don’t read cover letters. They flip through 100 résumés at a time, so it’s more important to make sure your résumé is really great. In terms of general job searching, I get nervous about leaving work to go for an interview. She said you should schedule them toward the beginning or end of the day.”
Assessment: “The name ‘mentor’ is a little misleading. A mentor is someone who stays with you and helps you because it makes them feel good, and not for money. The idea of paying for a mentor is weird, and I don’t know if this is worth that much money—maybe if you were changing careers completely. She sent me a follow-up note, but I think it’s more just a summary of what we talked about. I liked that I could control what we talked about but would’ve preferred if she had a little more guidance. I was expecting more, like Here’s a formal list of things we go through.”
Situation: Angela, 38, has nine years of experience as an independent TV and film producer in New York City. She wants to move her career forward and find a permanent position with a network or major company.
Session (with Career Contessa mentor and career strategy coach Leila Hock): “I know exactly what I’m doing, and I just want to go up the ladder. Right now, I’m in between projects. I told her I produce TV and movies and don’t want to be independent anymore. Once I explained my situation, she got a really good grasp of where I am and my personality. She was realistic. She said don’t just send your résumé; you’ll never find a job that way. It’s about who you know, so make these connections on LinkedIn and set up a date. It makes way more sense. I’ve sent in a hundred thousand résumés cold, and I’ve never gotten a callback. The truth is, especially in film and television, everybody knows someone. So her advice was to sit down, look at other people who have careers that are at places I want to be, message three people a day in my LinkedIn network, and see if they’re willing to talk—which I would never have done before, but now I will—and find out what their jobs are really like.
“She saw my résumé and my LinkedIn, and she was fine with the way they looked. It was more how to translate what was on the page to an interview. She told me about the STAR method (situation, task, action, and result). When you go into an interview or when you write your résumé, you make sure you start with explaining the situation, you tell them the challenge, how you handled it, and what ended up happening. Then she told me to practice three stories about the way I work, using my positive traits, that I could say verbatim, like a pitch. I can pitch a TV show in a second, but I never looked at myself like a movie. She also gave me tasks to work on every day so I could be productive. She told me to look at my personal networks, have coffee with my friends in the industry; she said not to bitch or whine, and slip in a sneak ‘Andrea pitch.’ Basically listen 80%, sneak in 20% about ‘Here’s how I can help you.’ Even if I don’t get a job, maybe I can help them later on.”
Assessment: “She helped me with how to take my independent life and turn it more into a structured situation. While most of her clients are corporate, she still had knowledge about my industry. She’s well-rounded enough to apply certain things that she wouldn’t say to them to someone in my industry. She followed up really quickly and left points we talked about and resume tips in an email. Our 50 minutes went quick, but at the end, I didn’t feel cut off at all. She was solid and constructive. I’d do it again, 100 percent. And I would pay for a check-in to mark progress.”
Situation: Kaitlyn, 40, has worked in the fashion industry as a stylist for well-known brands for the past 15 years, but in the last few years, she hasn’t been able to find steady work. Meanwhile, she’s dabbled in real estate, buying two apartments, sprucing them up, and selling them at a profit. She is now interested in transitioning to work as an interior designer—ideally, without having to go back to school.
Session (with Confetti Kitchen founder and editor Cynthia Samanian): “I was feeling like such a failure and was thinking I need to start getting temp work as a receptionist. Cynthia had checked me out on LinkedIn, and she told me she was blown away by my résumé. She said she couldn’t imagine why I was reaching out for career help. She feels interior design would be a really great transition for me. Some friends had suggested for me to go back to school. She said I didn’t need to, because I already have experience—flipping two houses and taking crapholes and turning them into beautiful apartments. She told me I have the eye, and pointed out that people have gone into bidding wars over my apartments.
“However, I still need to make money, and she said, ‘If you decide to switch careers and you’re going to go ahead full speed, obviously you’re not going to make money right away. Why not go be a retail associate at a design store where you’re going to make money and also glean insight into the business?’ It makes so much sense. Sometimes it’s nice to get an objective point of view. Next, we talked about how I would establish a brand identity and grow it through traditional and social media channels. She suggested I should reach out to people interested in renovating extra rooms to rent out on Airbnb. She said I have a really unique story and a perspective a lot of designers don’t have. What is the worst that could happen? I could go back to looking for styling jobs.”
Assessment: “She was so supportive, encouraging and had really good ideas, and offered me suggestions I had not thought of and had not heard from friends. She was the equivalent of a therapist—doesn’t need to know you personally to give you advice. Within an hour, she’d sent notes. It’s worth the money.”
Would you meet with a career coach? Sound off in the comment section below, and then check out our roundup of books by leading ladies that offer some killer career advice!