How Do I Get Someone to Take a Chance on Me?

Candid conversations about the messy middle

We are all doing our best. Let’s start with that. 

We are all doing our best, and the circumstances are complicated and complex, more now perhaps than ever before. 

Endless rounds of interviews. Working your network and your network’s network. Reports of new layoffs, new hiring freezes. Cold emails and cold applications into the abyss. Ghosting as far as the eye can see. It is, by every account, an untenable and inhumane system we operate in when it comes to searching for a new role or making a change in our careers. Whether you’re part of a recent layoff, looking for a new opportunity to grow your career or looking to make a bigger professional change altogether, a commonality we share is a sincere desire to learn how we can stand out in a crowded space; how we can get someone to see us for who we are and what we offer, and if the stars align, maybe, just maybe, get someone to take a chance on us.

To unpack this topic through the authenticity and vulnerability of real lived experiences, we sat down with Matt Kerbel, director of strategic brand planning at Turo, and Adweek Executive Mentees James Gregson and Kate Gagnon to talk about what it’s like to put it all in perspective, put yourself out there and how to not just be distinct, but equally discerning, in your approach. 

It’s a two-way street 

What we already know: You are interviewing a company and a team, just as much as they are interviewing you.

Hot Take: Yes, you’re here to learn how to get someone to take a chance on you, but we need to talk about how to make sure you’re taking the right chance for you. 

Take it from someone who’s been there: 

  • If somebody asks you that question, what do you wanna be in five years, 10 years? What does that look like? Explore how you can reverse engineer it—more importantly, the subject matter, the values, the culture of the role or organization. Become maniacal about culture, and ask really, really hard questions. —Matt Kerbel 
  • Everyone tosses around the analogy of interviewing is like dating or falling in love, right? The difference I think we all get trapped into is like, I just want someone to love me. Please, will someone just love me? Please, will someone just date me? But we all know that doesn’t lead to a very healthy relationship—both personally and professionally. The reality is you don’t want just anybody. —James Gregson

You are the only you

What we already know: The fundamental human need to be accepted is strong, but to be accepted for who you are so you are in the right role, working for the right leader, and part of the right organization is stronger.

Hot Take: It’s easy to get lost in the echo chamber of your mind, and lose perspective of yourself. In the pursuit of getting to know yourself from others’ perspectives, you’ll find not only what you uniquely have to offer, but perhaps even clarity on what you truly want. 

Take it from someone who’s been there

  • From rejection comes reflection, which leads to redirection. It definitely hurts at times, but at the same time, when I reflect and dissect the nuances of interview conversations, I see the times when I was trying to convince myself that it was a good fit. —Matt Kerbel 
  • Some people are good at giving specific feedback, and some people aren’t. The same goes with interview questions, especially about culture. I find that if you ask vague questions, you mostly get vague answers. As a candidate, you’ll get the most useful answers if you ask very specific or targeted questions. When you leave an interview round with vague answers to your questions, it’s easier to fill in the blanks yourself and, like Matt said, convince yourself it’s a fit. —Kate Gagnon 

Don’t let your vision get clouded

What we already know: The system is broken, like really broken. But we’re not going to change that. At least not right away.

Hot Take: Getting caught up in trying to make sense of the system won’t heal you, but it can hold you back. Find a sense of control and ease in staying clear-headed about what you can influence and what you cannot, and look for creative ways to hack the system.

Take it from someone who’s been there: 

  • Success comes from breaking through the noise and the clutter of other applicants. Think about yourself like a brand – how can you best creatively showcase what makes you unique and different in the bounds of whatever channel you’re in? An example would be, I made a deck about myself that was essentially a visual resume. It showcased the scope of what I can offer in visual form and represented the harder-to-describe in a resume nuances. —Matt Kerbel
  • Ask to interview or meet with someone who reports into this role from the team. You’ll get a lot more insight from the ground on what will make someone successful in this position than you might from someone in leadership —James Gregson
  • Ask about the history of the role. Very specifically, why are you hiring for this role? Has this role existed before? What didn’t work out with the last individual who filled it? Questions like these will help further connect the expectations for this position into the larger organization. —Kate Gagon  

We are all doing our best. We said up at the top, and it bears repeating. Write it down on a post-it, and put it somewhere you can see it as a regular reminder. You are capable of the job you’re going after. You have the experience, the skills, and you’ve put the reps in, you can do it. There are so many reasons—some known and some unknown—you may not have landed the job, the promotion or the contract. The old adage “it’s a marathon, not a sprint” couldn’t be truer of this experience. Patience, kindness to yourself, acceptance of controlling what you can and letting go of what you cannot, are all important to keeping a clear head to stay focused on the road ahead.

This article is part of The Gray Area, a new series that embraces the discomfort of the messy middle-career moments we all have through candid conversations among professionals in our Adweek community. Are you squarely in the gray area? Share your experience with us. It may inspire a future topic and bring about even more commonalities and camaraderie.