1. I got rejected from my dream job. I write strong cover letters showing why I’m THE right person for the job and have strong references and inside information from friends at the company. I’m right for this job. What else can I do?

Coffee talk with the supervisor and boss; Dream job

Start with a very detailed post-mortem. This is a medical term that refers to examining a dead body to determine the cause of death. Do the same for your situation. Are you really the right person for the job? Did your references check out? Ask your insider friends about your qualifications. Use them to find out who else is in the running and why they beat you?

Now you’ve done as much due diligence as possible, get cracking. Determine what is correctable. Determine what is not. Some will be readily fixable. Some will not. Like Affinity Bias. It’s our unconscious tendency to get along with others who are like us. We prefer co-workers who are not different from us. It takes work to bridge differences when diversity is present. Perhaps this is what is harming you?

You’ll need to evaluate whether the job is really what you want? Are you willing to make the compromises necessary to get it? Yes? Send an email. Make a phone call. Do whatever it takes to get back in front of the hiring manager. I have friends who even stalk the manager if necessary. Offer to take them to coffee or tea and show them what a fun and social person you are. All of this is in the service of the hiring manager seeing you as one of them.

As you do your due diligence prepare to course correct. Oftentimes, I’ve found that learning more and more about a job is like peeling an onion. You are qualified. You are awesome. But you still got rejected!!! Why? Maybe the company isn’t as great as you thought or the people aren’t exactly your people. Maybe there are other subjective factors out of your control. Add up enough of these and your interest in the opportunity wanes. But don’t stop. Do the work. Even though the more you peel, the more tears, at least you know more about the dream job you are fighting for.

2. The project I’ve been working on just got torn apart. I need to hit the reset button. What’s frustrating is that I followed my supervisor’s instructions and guidance to a “T,” but others above him shot it down. It’s obvious my supervisor isn’t on the same page with his bosses. How should I handle this. Should I seek counsel above my bosses head?

Dream job

Verify through multiple sources that your supervisor is not on the same page with their boss. Confirm that this is the reason. If this rings true, I would definitely raise your visibility with your supervisor’s boss. Otherwise, you will get blindsided. Again.

As we all progress in our careers, it’s really important to understand our direct supervisor’s motivations. And their boss’s as well. Everyone answers to someone else and knowing what motivates our supervisor is critical to your career progression and longevity. If you don’t know why your supervisor is making you do certain tasks you are flying blind. Make sure you have insight into your supervisor’s boss. Ideally the entire chain of command all the way up to the CEO.

There are many ways to do this. For instance, make sure you are present whenever your supervisor is interacting with their boss. You do this by offering real value add. Not just spectate. Offer to take detailed notes so nothing falls through the cracks. If your project is complex and will require Q&A, let your supervisor know that you would like to attend. You will ensure that the material is presented well. That the project is accepted without any issue. Usually bosses don’t wade through all the minutiae of their subordinates’ work. They prefer to ask probing questions. If you give enough good answers, they’ll presume the whole project was done well. Make sure your supervisor knows that you are there to support them. To make the project (and them) look good in front of their boss.

If your supervisor resists putting you in front of their boss, then try casual opportunities. Ask your supervisor’s boss to coffee or tea or (even better) boba! Try to make sure you get to know them better. Ask about the future of the company. Make clear you are happy in this dream job but want more responsibility and exposure. If done diplomatically, your company will reward you for taking the initiative.

3. It’s time for me to seek a new career as I’ve lost the passion I used to have for my current profession. I’m in my 40’s. When I pursue other opportunities, I’m often overlooked because I would have to take a salary cut. How do I convince people to give me a shot. I have the smarts and know how. I just don’t have the experience.

Dream job

Take solace that many people reach points in their career where they lose passion for their profession. They no longer have the same desire and energy they had for the job when they were younger. I’ve found that it does typically come in one’s 40s. You’ve achieved much but don’t see further progression or decide the toll on your personal life isn’t worth it. That’s what led me to retire from the intense world of Wall Street in my early 40s.

Once you’ve decided to make the leap and pursue your dream job, be sure to focus on what makes you unique. As I’ve said in the past, Be Unus. This comes from the Latin word for being the One, the Only One. Each of us is unique. Reflect on the skills that make you special and you can bring to a job or opportunity.

If you are in your 40s, you are unlikely to be able to differentiate on new technologies or skills that younger professionals might offer to an employer. However, you did work almost two decades in some industry. You’ll likely have demonstrated some level of management experience that younger candidates do not. Or you have industry contacts that others will find hard to replicate. Or if you are vying for sales facing roles, you might better fit the generational characteristics of your prospective employer’s customer base?

If you are vying for a dream job in a new industry, lean on your functional expertise. To spur your imagination, here are some examples.

If you were a…

  • Banker: Convince them your skills of financial acumen and detail orientation are easily applicable to their sector.
  • Lawyer: Everyone needs people who are good at negotiation and interpreting nuance.
  • Journalist: Impress them with your writing and communication skills.

Just don’t sell yourself short.

On the compensation, I have some sobering news. Oftentimes, you might not be a slam dunk hire. Unless you are hired for a role that you’ve mastered for 20 years, they are taking a risk hiring you. They mitigate some of this risk by paying you less. If you are making a shift into a new industry or role, be prepared to take a salary hit. The bright side is that at least you’re in the game. You’ve found your dream job. Make them see how incredible you are. Work your way up the ladder and then get paid!

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About the Author

Dave is a seasoned executive and entrepreneur who founded several companies in entertainment, investments, and technology, and worked on Wall Street for almost 25 years.

He started his career by joining a fledgling investment bank, Jefferies, when it had less than 200 employees.  Today, Jefferies is a multi-billion dollar diversified public company (NYSE:JEF).  He rose from the entry level position of Analyst to Group Head of Internet and Digital Media and was one of the youngest Managing Directors in firm history.  As one of the only managing directors of color in the firm, he successfully broke through the Bamboo Ceiling. He not only worked hard but also played the corporate game. 

Hundreds of bankers have worked for Dave during his career. He has mentored many of them who have gone on to some of the best business schools and companies in America.  He is eager to share his knowledge with Asian Americans and other disadvantaged groups seeking to maximize their potential and achieve their career goals.

If you want some great career tips and insights check out Dave’s book, The Way of the Wall Street Warrior, at TheWallStreetWarrior.com.

You can follow Dave at Facebook@Liucrative,Twitter@Liucrative, Instagram@LiucrativeEndeavors, LinkedIn@DaveLiu, or TikTok@Liucrative.

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