Don't Gamble with Your Career

Successful people don’t play by the house rules - Issue #61

I was recently reading about a candidate who had applied to hundreds of companies to secure a handful of interviews and eventually get a few job offers.

This sounds like a real-life variation of one of those ridiculous arcade coin-pusher games that my children always wanted to play.

Your odds of landing a dream job by applying to hundreds of companies are about as good as my children’s odds of winning a giant stuffed unicorn. Hint: they never did.


Gambling with your career

Toss your resume into the pile of thousands of other resumes, and hope it somehow tumbles into the recruiter’s hands. Then, cross your fingers and wish upon a star that the recruiter actually drops your generic resume on the hiring manager’s desk.

It’s a numbers game, right?

Widen the top of the funnel to hundreds — or even thousands — of job applications and, sooner or later, you’ll land a great job.

Really? A great job?

You researched those hundreds of companies and jobs so thoroughly that you would have loved to work at any of them? Bullshit.

However, that’s exactly what that guy did. He created a bot that generated multiple variations of emails, cover letters, and resumes, and applied to thousands of jobs over three months.

Let’s just say the results were less than spectacular. He discovered, as I have, that the best jobs aren’t left to games of chance.

Hiring managers don’t want just any old job applicant out of the pile. They have an entirely different strategy for locating the best talent. I know that I did when I was building my teams.

Random applicants are wasting their time. The most talented and successful job applicants don’t play by the same rules as the masses.


The numbers game strategy looks desperate

That strategy seems desperate because it is. We’ve all come across these candidates. The ones who use the same cover letter, resume, and email application for every company.

Hell, sometimes they literally even forget to change the name of the company or the job description. That resume gets dropped in the recycling box.

It reminds me of the guy I used to see at the high school dances who would start at one end of the line of ladies and ask each one out onto the floor. He was playing a numbers game, hoping that, sooner or later, someone had to say yes.

But, of course, everyone could see what he was doing, so no one felt very special when they were asked. No one said, “yes.”

I guess the modern-day version of this dating strategy is Tinder. A guy in the San Francisco Bay area built software that let him automate swiping right on 203,000 women in the Tinder app. He went on first dates with 150 women. By the end, he was still single, “$6,000 poorer, and profoundly exhausted.”

I know that some people have found success with the Tinder strategy. But, most have not. Some walk away feeling even worse about themselves.

You may still be tempted to use tools, automate the process, and try to game the job-hunting system this way. However, I know that there is a more reliable way to end up with a much better job.


Create an intentional career plan

Why would you take a “spray-and-pray” approach with something as important as your next career move? No wonder the people who adopt that strategy are frustrated and out of work for so long.

I’ve never played this frustrating game when I wanted a new job. I targeted two to three companies at the most. I went in with a laser-like focus, found an inside champion, and always ended up with an offer.

I knew the type of company where I wanted to work next. I knew the role that would take me farther along the career path I had in mind.

I was open to serendipitous opportunities, but I also set the wheels in motion when the time was right. I was deeply prepared for those specific interviews.

Map out where you want your career to go over the next ten years. Then, determine what the next best step would be for you.

Clearly define the type of role you want, the industry you desire, the kind of product or service you want to work on, and the type of company you want to join (e.g., startup vs. larger corporation). Include all of the other details that would make a company and job ideal for you.

Identify the target companies that best fit that profile. Then, start working your network to find your way inside.


Accept that the real gold is hidden

Treasure isn’t left sitting out in the open. All of the gold that could be easily discovered already has been (I live in Gold Country now, so excuse my metaphor). Up to 85% of critical jobs are filled through networking, and many of those jobs weren’t traditionally published.

“The competition for posted jobs is insane. ATSes do a horrendous job of selecting the best candidates, and–perhaps most important–the best jobs are almost never posted.” (source)

The best jobs aren’t dumped into the open market for hundreds or thousands of candidates to fight over. They tend to be locked up in the hidden job market, and it takes a different strategy to access them than the typical job search approach.


Find your way inside

I’ve talked about this before. A velvet rope and bouncers wait outside of the company’s front doors. A long line of candidates is already standing there, with their resumes in hand, desperately trying to win their way past these bouncers.

Do you really want to queue up and play that game?

You want your inside champion to come out, lead you past the velvet rope, and take you inside the company through the side door.

If it sounds like it’s probably a lot of work to find and connect with that inside champion, you would be correct. That’s why you can’t scale this strategy to apply to hundreds of companies simultaneously.

However, the good news is that you’ve already decided to intentionally set your sights on a small number of companies and roles that will best advance your career, correct? Working and growing your network to connect with a manageable number of inside champions is an easier task.

If you’ve already been demonstrating your expertise to the world, the champion may come to find you.

This happens when you do a lot of writing, podcasts, interviews, public speaking at conferences, sit on panels, teach workshops, etc. People get to know you, see how you think, recognize your talent and expertise, and decide that they want you on their team.

If you’ve been hiding inside the four walls of your last company, then you have a bit more work to do. You’ll need to strengthen your network, refresh your connections, and strategically let people know that you are in play.

However, do not broadcast publicly on social media that you are looking for a job. Again, that seems desperate. Engage with your network, find out who is connected to people inside your short-list of dream companies, and get a warm introduction.


Receive help every step of the way

Your inside champion now has a vested interest in you succeeding. They don’t want to bend the rules to bring you in warm, only to watch you bomb out during the interview process. If you fail, and now they look bad too.

Unlike the folks who got lucky and just happened to secure an interview with their random coin-pusher strategy, you have someone who will champion you through the entire process.

You know that getting that initial interview is only the tip of the iceberg. It takes a lot more to make it all the way through the entire process to end up with an excellent offer in hand.

I’ve witnessed the power of the champion from both sides of the table. I’ve had people bring me into companies, and it was clear that the interview was a formality.

I’ve literally had an interviewing decision maker say, “Well, <the champion> speaks highly of you. If he says we should bring you on board, that’s good enough for me.

I’ve also been on the hiring side of the table and had a candidate’s champion constantly shepherding that person through the process. He or she would make sure that we never dropped the ball, reminded me of how great the candidate was, and kept asking if we had made the offer yet.

Doesn’t that sound like something you would want as a job candidate?


Focus your time, energy, and power

You can gamble with the resume shotgun approach, scatter your energy in a hundred different directions, and watch most of your efforts fizzle and fade.

Or, you can put your power behind a few opportunities that really matter, win over internal champions, and knock it out of the park. 

Your choice.

But, know that the best companies don’t hire the best talent from faceless job applications. It may seem faster and easier. You may also think that maximizing the flow of your job application funnel would stack the odds in your favor.

But, that’s not how it works.

You’ll struggle even to get noticed and, believe me; someone else is already working their network to get connected on the inside to put their resume right into the hiring manager’s hands.

Be strategic with a short-list of great opportunities that will accelerate your career more quickly than just some random job out of a hundred. Find your inside champions and get that warm intro. 

Prepare well for your interview and get multiple offers to boost your negotiation confidence. That’s how you make smart moves that will change the trajectory of your career.

If you’d like some help preparing for your next job interview, let me know. You can also join my free Slack team, where many of us have deep experience interviewing, recruiting, and hiring.


Do the following Career Tips interest you?

Become a premium subscriber, and you can read these tips (and more) this week!

🍻Don’t forget to check out my upcoming meet-up in Palo Alto, California, on Dec 13th. I would love to see you there!


What I’ve been writing

  • In How to Build a Powerful Professional Network, I explained why the old ways of networking and power plays are fading from relevance. It will no longer be about who you know, the favors you owe, or your title. It will be about the value you can bring to the table. It will be about the kind of person you are.

  • In This Is How You Buy Back Your Freedom, I described my exploration of minimalism and why I tapped out of the Silicon Valley culture of materialism. Taking control of my lifestyle gave me the freedom to explore new options for my career. If you’re not happy with your job and you can’t make changes in your life because you’ve backed yourself into a financial corner, it’s time to take a hard look at the choices you’re making.

  • In You Won’t Live Your Best Life Without This Foundation, I explained how first-principles thinking could help you uncover the fundamentals of who you are and what you want for your life. Don’t try to replicate a “recipe for life” from some famous person. Construct your life around the five essential building blocks I talked about, and the rest will fall into place.