How to Be a Terrible Boss
Until I went to college, my only bosses had been the couples I babysat for, and generally, they were pretty pleased with my ability to keep their children alive, tidy up their kitchen while they were out, and help myself to the smorgasbord of snacks not regularly available at my house. We-heh-hellll . . . what do we have here? A row of Oreos and some Goldfish? Cool Ranch Doritos? Don’t mind if I do . . . (clearly not the epitome of nutrition in my teenage years).
When it came time to interview for my first “real” job, and by real, I mean a formal interview, payroll taxes, and a regular work schedule, I was pretty naive to the landscape of personalities with which I would have to contend. Enter Jane. Everything about Jane was intimidating to me. At first, anyway. Her raspy, smoker’s voice was loud and commanding. She entered abruptly into the office where I was waiting for my interview, still shouting orders at someone over her shoulder as the club’s main kitchen doors slowly swung less and less until they closed. She cursed. Often. Her questions were direct, but she smiled and let out her signature cackle in between them, and slowly eased a little bit of the tension I felt while wondering if I could hang in this environment. I did indeed hang. After one summer working for Jane, she promoted me to a manager, and I kept that job every summer until I graduated from college. In those four summers, I actually grew to appreciate working for Jane. And having had a multitude of jobs and even changed careers in the past 25 years (a few times), I now understand why Jane was a good boss.
The experience that solidified this understanding for me wasn’t working for the awesome department chair I had when I was teaching high school chemistry (although that certainly helped). It wasn’t the clinic director who hired me for my first pediatric dental position, even though I had a great working relationship with her and we grew to be good friends. It wasn’t my boss who went on to be the person I now look to as a mentor, a woman who emulates success in business and dentistry, but also happened to show me understanding and compassion during what I can only describe as a complete emotional breakdown. It wasn’t even my own experience as a boss, even though learning to hire and fire, budget, lead, and manage was an invaluable chapter in my career. No, despite having the fortune of having had some really great bosses, leaders, and mentors along the way, the experience that seared what makes a good boss into my brain more than any other was having a bad boss.
I was so frustrated one day after dealing with the all-too-common consequences of this boss’s lack of leadership, that in order to express my anger (without leading to the loss of my job, which at the time would have violated my contract and I frankly could not afford to lose), I wrote out a list of frustrations titled, “Things I Want to Say but Can’t.” I had already tried to have respectful, professional conversations with this boss in the past, but experience had proven those to be fruitless. Spilling my thoughts onto paper at least allowed me to channel that emotion into something outside of me so that I could get it out of my system. What I didn’t realize I was doing by naming all the behaviors that made me want to bang my head against the wall on the regular was creating the prescription for being a great boss. The kind of boss that people are loyal to. The kind of boss that leads by example and that people clamor for the opportunity to work for. The kind of boss that inspires people to be the best versions of themselves. That spontaneous list of grievances has now become the rubric by which I measure all bosses: the ones I work for, the ones I coach, and of course, myself. It also serves as a value-based guide when faced with tough decisions. If a leadership choice violates one of these principles, the answer is clear. Don’t do it.
So, without further ado, “Things I Want to Say but Can’t: What Makes You a Horrible Boss”
You lie.
This one is the foundation of all the others. As soon as your team knows that they cannot rely on your word, you’re done. Your credibility is the capital you must own to have the right to celebrate your teams’ wins and reassure them when you have to weather the storms. You are impotent as a leader without it. Don’t tell variations of the truth. Don’t exaggerate. Don’t convince yourself a lie is harmless because it seems like a detail you find insignificant. Or because you think no one else will ever find out. YOU will know. And if there’s anyone who needs to trust your word most, it’s you. Tell the truth, or don’t tell anything at all.
You are financially irresponsible.
As the principal steward of your business, you are the captain of the fiscal ship. And if you put your business’s financial stability at risk with poor and/or self-serving decisions, then you also jeopardize the livelihood of everyone who works for you. If your team believes you’re willing to risk the business’s and therefore their own financial security to satisfy your own impulses, then I promise you they’ll be surfing Indeed in no time and out the door shortly thereafter.
You take credit for others’ wins.
Never pass up the opportunity to credit someone else when things go right. Always hold yourself accountable when they don’t, because even if you didn’t directly cause the breakdown, you’re still responsible for preventing it from happening again. Taking credit for someone else’s meaningful contributions and/or blaming someone else when things go wrong are death for your leadership. Both go back to the issue of trust, and once that’s lost, it’s very hard to regain.
You’d rather invest in things than people.
Your team is your biggest asset. Period. Set the bar exceptionally high for the types of people you bring on to your team. And then once they’re there, don’t let them think for one second that you don’t know that THEY are the ones that make or break your business. Yes, pay them well. Very well. If that means postponing a purchase that you want but don’t need, so be it. But investing in them means more than their salaries. It means investing in their well-being, their fulfillment, and their time. If they think that you value a display of wealth more than you value their effort and contribution, you will be forced to set the future bar much lower for those whom you employ.
You care more about what other people think than what you think.
If your business philosophy is to project an image of success, you’ll inevitably get in the way of your own potential, and true success will elude you. If you create a value-based culture and support an A+ team, success is a byproduct . This means not caving to external pressures that don’t align with your core values. Your values are your curb, your guide, and your mirror. They show you the way, even when the way isn’t what everyone else is doing. Especially when it’s not what everyone else is doing.
You don’t manage your time or the time of your team well.
Do you consistently miss deadlines? Are you overscheduled and overcommitted? Regularly distracted? How often are you running late? Is your day efficient? Or is it chaotic? How often do you have to reschedule an appointment? In short, ARE YOU RELIABLE? No one likes to have their time wasted. Not you, not your employees, and not your clients/patients. Sure, everyone runs into the occasional unforeseeable circumstance, but when this behavior is chronic, you are deliberately choosing to tell others around you that their time is less important than yours, and quite frankly, that’s arrogant. Honor your commitments. Be present. Don’t multitask during conversation. Don’t glance at your watch or your phone. Give the person across from you your genuine, undivided attention.
You don’t follow through.
Not to beat the dead honesty horse, but this one is critical for recruiting and keeping A+ employees. If you tell a staff member that you’ll follow up with them regarding a raise request, follow up. If you explain to an underperforming employee that the next infraction will lead to termination and they don’t change course, let them go. If you say you’ll come up with a solution a week from now, provide the solution a week from now. If and when you fail to follow through, acknowledge it immediately, and commit to reconciling your word with action. Everyone fails to follow through sometimes. And most people are generous with the benefit of the doubt when it happens. But if you consistently show people who you are, don’t blame them when they believe you.
You don’t understand good delegation.
No great leader can be a micromanager. And at the same time no great leader can be aloof. So how does one successfully lead while letting go of the reins? See #4. You invest in the highest quality people. Ahhh, but that’s not enough. You invest in the highest quality people, and then you trust and empower them to do their jobs. You listen to them. You put your faith in them. And then you see what happens when they are permitted to be creative, think critically, and solve problems. What does this mean for you? It means you are free to be the thought leader, the visionary, and the buck-stopper when necessary. There is nothing more frustrating than a boss who tasks an employee with an enormous amount of work, doesn’t take the time to properly review or consider the work, and then does what he or she wants anyway. Busywork is a waste of time, whether it’s 4th hour sophomore English or a 9-5 job. Respect your employees’ time and talents. Trust them to be great. Be the one that gives them wings, not clips them.
You tolerate mistreatment from others.
For most of my life, I thought that an attitude of service was mutually exclusive with prioritization of self care. I’m not sure exactly how that belief fully developed (I have some theories), but I was older than I would have like to have been when I realized that it was a falsehood I could no longer afford to hang on to. One of my favorite quotes from Jordan Peterson is, “Treat yourself like someone you are responsible for helping.” What does this mean exactly? Well, for starters it means being kind to yourself. It means being acutely aware of and deliberate about the way you talk to yourself. If you wouldn’t talk to a close friend in a disgusted tone, then don’t talk to yourself in a disgusted tone. If you wouldn’t bail on a commitment to your younger sibling, then don’t bail on a commitment you made to yourself. And if you wouldn’t let your best friend off the hook when they needed to hear some loving truth, then don’t let yourself off the hook either. You can’t expect to command the respect of your employees, clients, and colleagues if they don’t witness you showing respect to yourself. Taking care of yourself and treating yourself with kindness and respect affords you the privilege of being in service to others, and there is absolutely no shame in that. In fact, as a leader, you are compelled to do it.
You resist change, even when the data supports that the status quo isn’t working.
Nothing changes if nothing changes. It’s innate to our human condition to resist change. Our brains are hardwired to seek out the familiar, even when the familiar isn’t what’s good for us. That makes consciously choosing change extremely difficult. Because when you choose change, you also choose uncertainty, and no one’s subconscious signs up for that. However, if the current state of affairs isn’t up to par, and you have an A+ team around you to support you, then choosing uncertainty is the only path forward if growth and success are the ultimate goals. Not choosing to change is also a choice. At best, it’s a choice to remain mediocre. At worst, it it’s a choice to undermine yourself and everyone who relies on you. Recruit a great team around you. Do your homework. Hold tight to your core values. And when you find your toes on the edge of the cliff of change, jump. Trust that your parachute will open and your people will be there at the bottom to celebrate with you.
Having formulated this list of non-negotiables over the past 25 years, it’s why despite Jane’s abrasive personality and intimidating demeanor, I respected her. That respect was the product of knowing that she said what she meant and she meant what she said. Trust is what made her a good boss, even for an entry-level job that was a stepping stone in a much longer career path. Every great boss I’ve had along the way understood this. It didn’t mean they didn’t make mistakes, and it certainly didn’t mean every decision they made was a great one. But every single one of them went on to be wildly successful because they anchored their leadership on trust, consistency, and prioritizing people over things. The irony in achieving success in leadership is that the better you get at it, the more you have to let go. Not of your dreams, ambitions, values, or drive. But of the need to put yourself at the center of the operation. It’s realizing again and again that by stepping out of the center, you have the ability to make the playing field bigger, better, and more impactful by permitting the team you’ve built to shine. At its core, leadership is about authenticity in relationships. It’s not telling people who you are. It’s showing them. Over and over and over again.