How to Hire Your Own Boss in Your First (or Second) Sales Position

by High Alpha
Yeah…I’m gonna need you to come in on Saturday.

Imagine a world where you could choose your own boss. You’d choose the person that will mold you into the next successful sales prodigy and get your career ready to skyrocket. The boss that could put you on your path to being the next Zig Ziglar — or at very least, a top performer at your organization.

One of my favorite questions from young sales professionals looking to land their first sales job is, “what is the best advice can you give me?”

My response: “You need to go hire your boss.”

What that means is you must search for the best leader you can find for you. It’s important to remember that when you walk into an interview, you are choosing them just as much as they are choosing you. Making an educated career choice — bolstered by trusting your gut — can lead you toward the leader who will set you on a successful career path.

Your first boss is your career blueprint

Every career has its ups and downs, but the first professional leader in your respective career will have a lasting impact on you. They provide the blueprint for how you think and act professionally for decades to come. The way you interact with prospects and clients, the wisdom and adages you internalize and integrate into your daily work life, and the essential knowledge you pass on to the sales professionals you are lucky enough to mentor — your first manager will have a heavy hand in all of those aspects of your professional life.

All of the years of school and odd jobs have gotten you to a point to where your boss can use all of the skills you acquired in a real-world setting. A good boss will be able to mold those skills into something useful; a great boss will mold you into someone exceptional.

Interview for at least five sales positions

This is the tactical follow up to “hiring your boss.” Exploring as many options as possible will help you determine whether you are making the right choice with the company you choose.

Take time to proactively reach out to peers who recently made the jump into sales. Ask your other trusted mentors and friends for introductions to different sales leaders willing to help you explore your interest in sales. Invest in talking to people who have years more experience than you.

Remember, however, that how you think and act is different than those offering advice. You need to think independently to make the right decisions for yourself. Your first job is not about the biggest base salary, nap pod or open snack bar. There will be plenty of time for that later in your career, and you cannot let shiny objects cloud your judgement. If you make the wrong decision on your boss, none of those things will matter. Also, when you play your cards right, all of the perks come to you in time.

Decide whether you could work with your potential peers

Your potential peers are a direct reflection of your potential boss. If they appear to be mediocre workers, chances are you will end up a rising star on a mediocre team. Or worse: you could end up becoming a mediocre salesperson and hating your job. If being okay at a job that offers you
amazing benefits for ten or twelve years is your goal, go for it. But eventually, someone will “fix the glitch” and get rid of underperforming sales team members.

It is inspiring to work around people who make you better — peers who, along with your boss, pick you up, push you to grow and build a solid foundation of skills. You are going to spend a lot of time with the rest of the team, and you need to at least know they will make you better. You do not have to like each other — just know they are willing to put in the work everyday like you are.

As you hire your potential boss, you are also hiring your team that surrounds you. Ask questions about where team members want to be in their careers, or what it is really like working for your potential boss. If your gut says something is wrong, listen to it and investigate more.

When looking for a sales position, finding a boss that can show you the ropes and teach you valuable skills not just in sales, but in life, is critical. You are who you surround yourself with, and many of the choices you make are directly affected by your surroundings. If you want to be a high achiever, you cannot surround yourself with others who do not have your standards — your boss included.