Some people think that it’s a privilege to get to pick your boss.
Others think that it’s a pretentious and even a snobby attitude. Some claim it’s the cope of a powerless plebe – “I’m choosing my boss as much as they are choosing me.”
And even others, who approach getting jobs with deep desperation, can’t even imagine how any professional can get to chose their boss or teammates.
They are all wrong.
The truth of the matter is very simple for the high-value professional:
Employment for a high-value professional is like matchmaking. It takes two parties to voluntarily agree on the terms of the employment contract.
And for that contract to be viable, and also fruitful in the long term, it MUST be win-win.
Win-Win Employment Relationships
At a fundamental level, your employer must get more revenue out of the agreement than they put in. But that’s just the starting point…
The employer must also find it easy to work with you. We don’t want your employer losing any hair because they have to manage a resentful, uncooperative or a “maliciously compliant” employee. (Happens far more often than you think)
Similarly, you must get paid more by the employer than what you could get from any other comparable business where you could get a job. But again, that’s just the starting point. You must also get to hone your skills, expand your network and reputation, and also, receive some form of official professional development – usually the kind that costs them serious money.
This is why, when you are contemplating whether or not to get a particular job or work with a specific boss, you need to ask the question:
What else are they giving me besides the money?
Here are some key points to help you evaluate what a boss brings to the table:
- Official experience to go on your resume
- New or expanded job skills
- Professional mentorship (personality development)
Mind you, I’m not mentioning network expansion here for a specific reason: While different employers do provide different levels of network reach, in our experience, your network grows based primarily on your personal initiative. Unlike the other items listed above, which can ONLY develop through your interactions with a boss or an employer.
Let’s unpack each and give you the tools to evaluate your current, or perhaps your next, boss on each of these three dimensions…
1. Official experience to go on your resume
This has to do with what your boss asks you to do.
Your boss will have a disproportionate say on what specific projects and problems you work on. This, in turn, will give you the “official” professional experience which you can put on your resume. Which, in turn, will help your career development by qualifying you for future, better, higher value and higher paying opportunities.
For instance, let’s say you work in the marketing department of a construction firm as the marketing coordinator.
Your boss could stick you on scheduling ad buys and reaching out to various local newspapers which he already has a relationship with. This could be ALL you do for the entire time you work with him. And it would give you legitimate, official, resume acceptable marketing coordination experience.
Or he could have you actually search for new channels, evaluate their costs vs benefits, reach out to the ones you pick, set up meetings and negotiate terms. This would, beyond your coordination, also give you media buy experience, maybe even business development experience.
I don’t need to tell you how the latter is a lot more valuable than the former…
The point here is that, when you’re interviewing your next boss, you need to get a sense of their level of risk tolerance as well as their ability to delegate.
If they are sufficiently risk tolerant, and able to delegate, they will let you try new things and help you develop. If, however, they are risk averse and prefer to keep you on a tight leash, you’re going to be pigeonholed, and keep doing the same thing over and over again.
Mark my words: Whether or not your boss lets you develop is 100% dependent on the boss, and has zero relation with the business. I’ve had my bosses give me projects completely against company policy. I’ve done the same for more employees I can count. Conversely, I’ve seen bosses for supposedly “creative” departments micromanage their workers, down to picking the specific words they use when they send out emails.
You can imagine, which type of boss is more career expansive to work with…
In fact, this is perhaps the most important quality you need to test in a boss: Ultimately, the difference between a job and a career is in whether or not you gain new experience that makes you employable at a higher pay-grade. A boss that won’t let you get that experience is a big, hard NO.
2. New or expanded job skills
While official experience is about what you do for work that you can put on your resume, job skills are about how you do that work.
In the above example, where you simply do marketing coordination, you are effectively working as a glorified assistant. You develop the non-skills of showing up on time, following instructions, sending emails and writing stuff on paper.
That’s not a place where you want to be…
In the second scenario, however, you are developing a number of high-value skills like critical thinking, communication, and negotiation. Moreover, your job not only gives you future demonstrations of high-value skill, but also demonstrations of importance – you don’t just do what you’re told by coordinating things already decided on, but you also get to influence and make decisions as part of your job.
In other words, when you evaluate your boss, you not only need to “suss” them out to see if they will let you do more than what’s on your job description, but that they will also enable you to flex new muscles in a way that develops new skills.
You need to know that they see you not as a worker, but as a learner. And, of course, you need to ask them the right questions to determine whether this is the case or not… Make no mistake: just as employees bs in their interviews, employers will say all sorts of things that they don’t really mean if they want to hire you. (See Launch Your Career for the complete set of questions you must ask employer to get a high-value job where you can grow)
3. Professional mentorship (personality development)
While the first dimension was about letting you gain new and valuable job experience, and the second was letting you develop new high-value skills, in some sense, these are secondary to the most important quality you should seek in a boss:
The “Professional Personality“.
You see… Human beings are like sponges, and we absorb qualities from those we surround ourselves with and interact with on a day to day basis. And when it comes to your interactions with your boss, it becomes even more pronounced because there is a hierarchical relationship that literally changes how your brain processes your relationship.
You want a boss who has personality traits that is worthy of looking up to. You want them to have their act together. Furthermore, you want them to be an ally in you developing your professional personality.
Let me elaborate…
A few years ago I had a boss with whom I had developed a friendly relationship. And we often talked about self-development in the context of my work and how I could become a better executive.
In this dialogue, he wouldn’t just tell me “go read this book”, or “go develop that skill”, or “go attend this lecture”. In other words he didn’t just encourage my skill or experience development.
While he did do all those things listed above on occasion, he primarily went a step deeper and gave me insight into my blindspots and how I could improve myself.
For instance he would often call me on how opinionated I was, or how much of a perfectionist I was, or how I expected too much from employees.
He also gave me invaluable insights into what new professional personality aspects I could develop. Like guiding me in developing a higher tolerance for risk, or becoming focused on the discovery process of finding new profit and growth, rather than just efficient execution of plans.
In the arc of your entire career, if you have half a brain and a solid level of ambition, you will inevitably develop experiences and skills. Both of which are commodities, which are, while necessary, not the differentiating factor for getting to the top of a high-value career.
What truly differentiates you, sets you apart above your competitors, and enables you to make a real difference in business is those dimensions of your personality that make you a better professional.
And while you can develop some of that through books and self-reflection, it is much more efficient, and arguably more effective to have personality mentors (mentors that help develop your personality and you absorb qualities from).
Ultimately, you want a boss that has the capacity to mentor you. And if that’s not the case… Because, let’s get real, not every boss you work with will be a worthwhile professional, sometimes you just have to tolerate them as a stepping stone…
If you aren’t at a level where you have bosses that can mentor you, you NEED to move up and get to that next level, where you can surround yourself with such exceptional professionals.
There are incredible, ethical, high-value, high-performing, intelligent, educated, pleasant and even charismatic professionals in the corporate world. And if you’re not working with them, you need to get to a place where you DO get to work with them.
Of course, the fastest way to do this is to upgrade your career skills…
So… Whether you’re working on getting your first job, or have been in your industry for a while and are ready to admit to yourself that you deserve a change, and a better boss, my advice is going to be the same:
Use our framework to get high-value jobs, and do not stop getting promoted until you reach the highest and best use of your time.
The world will thank you for it. Your future self will thank you for it too.
Every second of your life counts. Make the most of them.