7 Signs You May be a Bad Boss

7 Signs You May be a Bad Boss

Leadership Tips to Get Your Team Back On Track

Nobody likes to think of themselves as a bad boss. But in my travels through the leadership keynote speaker world, I’ve met so many current and aspiring leaders. And whether they’re newly minted managers or seasoned C-suite types, regardless of their leadership tenure, it’s quite common for people to have a few blind spots around their own leadership styles.

Case in point: when I became the CEO of my family’s $120M car dealership business at the tender age of 28, I made some colossal leadership blunders. During a time of transition, my team was counting on me to be a combination mentor, coach and creator of a compelling vision for the future of the company. In reality, though, I needed someone to provide ME with all of the above! And, until I found the mentorship I was seeking, I was indeed a very bad boss.

Today, more than two decades later, I have the benefit of hindsight—but also the wisdom of failing, and learning…and trying again. Without this experience, I doubt I would be at the helm of a successful leadership keynote speaker business. So, with this in mind, I’ve spent some time pondering the biggest leadership pitfalls of my past. If you see yourself in any of these, it might be time for tune-up!

1. You’re a Micromanager

Regardless of the industry, micromanagement is consistently one of the biggest complaints from employees. One study found that nearly 60% of employees claim to have worked under an overbearing boss—more than 1/2 said this harmed their productivity, and nearly 70% said it affected their morale. While these statistics apply to employees on every rung of the corporate ladder, they are even more likely to be destructive to relationships with your A-players.

When I was first (quite unexpectedly) thrust into the CEO role, I understandably felt I had something to prove. We were in the midst of conducting a financial turnaround on a loss-making enterprise, and I wanted to control every aspect of the company. This covered areas that were part of my education and skill set (like inventory, cash management and sales) as well as things that most certainly were not (like HR and administration).

Despite my relative inexperience, I felt certain that none of my talented subject-matter experts could perform their jobs to MY high standards—so I struggled with giving them autonomy. I would ask employees to check in with me before sending an email, giving a presentation or holding a meeting with a key customer or one of our manufacturing partners.

Of course, my heart was in the right place. My goal, albeit a misguided one, was to prevent employees from making mistakes that might lead to us losing more money. Not only was this strategy impossible and exhausting—it was potentially more harmful than letting my employees “fail forward.” As Steve Jobs famously said, “It doesn’t make sense to hire smart people and then tell them what to do. We hire smart people so they can tell US what to do.”

My Advice: Set clear parameters, and then let your team get on with it! If you’ve done your due diligence with regard to hiring, things are going to work out fine. They may go about their jobs differently from the way you might, but this will often result in finding a better way. They’ll have the opportunity to make mistakes; chances are, they’ll learn from them, too. This is a critical part of both personal and professional development—both theirs and YOURS.

2. You’re a Negative Ned (or Nellie)

Think about the last 1:1 you had with an employee. What percentage of that conversation was about their mistakes—and what percentage was spent celebrating their victories? In a performance review I had with my longtime assistant, Jean, I was shocked to learn that I ranked among her most demanding…and least complimentary…bosses.

Why? Because even though I was extremely happy with her performance—she ultimately worked with me for 22 years—I always pointed out her mistakes, even if they were minor. I rarely, if ever, gave her positive feedback. I’m sure it wasn’t easy for Jean to deliver this feedback, but her bravery that day was critical to my professional development. I took her observations to heart, and began to make a concerted effort to balance recognition of a job well done with suggestions for improvement.

My Advice: There’s a reason the Carnegie tidbit “be lavish in your praise” has endured all these years! When you chat with your employees, make sure you spend ample time talking about what’s going well. This is not to say you can’t, and shouldn’t, deliver constructive criticism—just be judicious with negative feedback, and work to reinforce the good.

3. You’re an Ivory Tower Leader

We’ve all had them – that boss who remains camped out in the corner office, door closed, unimpeachably Doing Important Things. After all, what good is a C-suite title if the minions are allowed to stop by for a chat or [GASP] give feedback—isn’t that just questioning one’s management authority? This is a mindset I’m still surprised to see on the leadership keynote speaker circuit, and I can’t discourage it enough. It’s outmoded and unhelpful…and indicative of a serious leadership growth opportunity for you too.

It’s so important to remember that leadership is the ultimate exercise in lifelong learning. Even after my revelation with Jean, and the subsequent leadership style adjustments I made, there was still plenty of room for improvement! When we finally introduced 360-degree assessments into our performance review protocols, I was surprised to learn that many of my direct reports still found me demanding, but largely unavailable—I was always in a meeting.

Employee 1:1s and performance reviews should never be a monologue, with you dispensing mysterious wisdom like Obi-Wan Kenobi. If we’re to continue with the Star Wars simile here, consider instead emulating Yoda and Young Luke—a constantly evolving, collaborative mentorship meant to maximize the unique powers of each individual. Succeed, you will.

My Advice: Be curious. Make these important conversations a dialogue, even if it feels uncomfortable at first. You should welcome the opportunity to receive feedback about you as a boss, and the organization as a whole. Do what you can to remove barriers. Take time to ask questions, and pay attention to the communication styles your team members prefer when giving you feedback; some may find phone or email less intimidating than a face-to-face conversation. And finally, make sure employee feedback is part of YOUR performance review! Even if the company is your own, your performance must be evaluated. In the end, cultivating these important conversations will be just as instructive to you, as you evolve as a leader.

4. You Lack Insight and/or Vision

I want to start with some quick definitions, because even though both words are related to seeing—insight and vision are very different with regard to your business. By insight, I mean looking inward at the company: where you’re at with people, performance and the bottom line. Vision, by contrast, looks outward: where is the company headed, and how will you get there? Both are essential to success, so lacking in one or the other can be a serious pitfall.

Insight: In the family business that I suddenly found myself leading, the only people who historically saw the financial results were my father, his CFO and the family shareholders at the annual owners’ meeting. That’s a very small, exclusive group. When I took the helm, neither myself nor the employees had any idea of the dire financial straits we were in, how much money we were losing, or how quickly. This led to a dangerous lack of urgency for change.

Vision: Since 2010, the word “purpose” has appeared in the titles of more than 400 new business leadership books. As we navigate the global transition to Millennial workforce domination—not to mention the meteoric rise of the even more purpose-driven Gen Z—having a clearly defined company vision will be essential in nearly every industry. If your company’s vision statement is something like “maximizing stakeholder value,” listen up.

Even if you’ve stepped into a leadership role at a family business like I did, you should still have a vision. Think about it this way: if you were applying for your own CEO job, how would you get it? Where would you want to take the company over the next five years…or 10? What route would you take, and what tools would you use? And perhaps most important of all…why? Until you can confidently answer all of these questions for yourself, you’ll have a very difficult time getting your employees to understand or care about their jobs on any real level.

My Advice: Start by setting some basic team goals for the month, the quarter or the year. Ask your team to commit to milestones along the way, and be open to feedback. I used to do a combination of weekly managers’ meetings, monthly team briefings and semi-annual all-staff team meetings to communicate our vision and why it was important. I also spent time with each new employee discussing how their specific role might impact our vision—this is probably the piece that’s most critical to employee motivation.

Finally, when I was walking around one of our six locations I would casually ask an employee who I was in conversation with, “From your perspective, how do you think we are doing with regards to moving towards our vision?” It was amazing what I learned by just asking this simple question—both about the business and the individual.

5. You’re an Inconsistent Boss

You’d be surprised how large an impact a few little inconsistencies can have. Whether you’re discussing something administrative like the company’s work-from-home policy or a big-picture issue like career trajectory, your employees are listening—and looking for your guidance. They expect you to have a stance and stand by it. So, regardless of the issue, when you contradict yourself, it causes confusion and erodes confidence in you as a leader.

The same is true when you don’t hold all of your employees to the same standard. At one point, the person who was best man at my wedding was working for me as a sales manager. While the temptation might have been to avoid conflict with a close personal friend, in reality I knew I had to hold him to an even higher standard to offset this perception.

My Advice: Put everything in writing, from company policies and procedures to employees’ personal and professional goals. This will not only serve as a compass to guide your business journey—it will also give everyone something to refer back to along the way.

6. You Expect 24-Hour Availability

As a business leader or owner, it’s normal (within reason, of course) for one’s work life to spill over into one’s personal life. Even for those of us with healthy boundaries, there will always be the odd late night or weekend workday. You might also expect this from your A-players, and that certainly wouldn’t be abnormal or unreasonable. But if you’re expecting the same level of availability from every player on your team, you just might be a bad boss.

I have a friend whose son is in his mid 20s. He worked for a digital marketing agency, and his boss was messaging or calling him at all hours of the day and night—he felt like he was required to be “on” 24 hours a day. Eventually he left that gig for an agency that was able to respect his personal time. And he’s not alone! According to a 2019 report, 50% of Millennials and 75% of Gen Z employees reported having left a job they felt was detrimental to their mental health. Burnout is real, folks…and the incoming workforce will not stand for it.

My Advice: My assistant for my real estate business lives in the UK—a seven-hour time difference from where I’m at in the U.S. If I leave her a VM, send a WhatsApp message or barrage her with emails at 2:00 pm MST, that’s 9:00pm for her. That’s family time — recharging time.

We’ve set clear ground rules around time zones and communication, and she knows that I’m not expecting a reply until her next business day is well underway. Even though I might send a communiqué during my business day, when the issue is on my mind, we’ve agreed that getting a reply is never more important than her personal time. The same should hold true, regardless of time zone or role in the company—and that rule should go all the way to the top.

7. You’re Always the Hero

Have you ever worked for a boss who wanted to take all of the credit when the team won a new client, or had a big win? Yet when things were going badly, they were the first to look for a scapegoat rather than take responsibility?

Early in my career, just after I left university, I worked for someone who was exactly like this. He also had a compulsive need to win at everything, no matter how trivial, which became very annoying and demoralizing to his team. I wasn’t sure if this was because he had a massive ego or because he was insecure. Either way, it meant he turned over a lot of people.

My Advice: Give sincere praise and recognition to the individuals who work for you, and the team as a whole—and make sure they get public pats on the back when things are going well. A real leader takes responsibility when things don’t go as planned; this unfailingly inspires loyalty and stokes motivation. And a real leader derives gratification not from fanfare, but from long-term performance improvement…and the satisfaction of seeing their team shine.

Want to grow your team so you can also grow your business? Ask about CEO & Leadership Team coaching.

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