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Common Mistakes Executives Make -- Even Though We Know Better

Updated on July 18, 2016

Google CEO Larry Page

97% of Google employees approve of Larry Page as CEO.
97% of Google employees approve of Larry Page as CEO. | Source

The title sounds a bit salacious, but I am not referencing affairs with a co-worker, sexual harassment, discrimination or embezzlement. Most executives avoid these obvious career-killers, though a fraction believe these rules do not apply to them. My focus is on the errors in judgement we executives make honestly believing we are improving the team and the organization, but in fact the decisions are undermining the organization and jeopardizing our roles as a leaders.

Preferring Liked Versus Respected

I have heard it and said it a million times. "I would rather be respected than liked." I meant it too, but it is the rare person who genuinely can say being liked is not at least as important. In fact, being liked is human nature. We all want to be accepted and acceptance begins with likability.

By definition tough decisions produce winners and losers. It’s our job to make those tough calls with the limited information we have and to soften the blow to the side that didn’t get their way. Too often, especially in a small setting with a few staff members under our direction, we hedge on those tough decisions in an effort to keep everyone happy. The other approach is we make the tough decision, then offer some unreasonable level of compensation to the "loser" that both costs the company and sets a bad precedent.

My experience is go for respected, and you may end up with liked. However, if you go for liked you will probably never achieve respected or liked. No matter how many times you bring doughnuts, order-in lunch, look the other way when a staff member shows up late or leaves early, or how much you banter about a favorite team or hobby, you are still the boss. That makes you the authority figure, for which today's culture lacks appreciation. You still have to make decisions some will not like. Do not forget as boss, you have pay, perks and privileges as a part of your package that others don't have. That creates a natural tension.

Respected, of course, doesn't mean you have to be totalitarian. Demonstrate you work hard too. Show you are knowledgeable about the jobs of your subordinates, particularly the struggles. Employ constructive criticism, but don't forget to say "good job" as much as you criticize. Be kind. Kindness is not weakness. Be as fair to every employee as your internal circumstances allow. Use facts and data to back up tough decisions. When decisions affect someone's job or quality of life, they really don't care about your "gut" or intuition.

Be kind. Kindness is not weakness. Be as fair to every employee as your internal circumstances allow.

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Co-workers as Confidants

Whether a mid-level supervisor or CEO, tremendous pressure comes with being the boss. We all need to vent now and again. We need someone with whom we can share impending major decisions that will affect the company and employees. Sometimes we need a sympathetic ear when we've screwed up. My advice? Tell a mentor or friend outside the company, confide in your spouse or tell your "Shrink."

The Chicago Tribune's Interpersonal Edge writer agrees:

"You have to decide if your connection with each co-worker is a friendship or work relationship. If you chose friendship, sooner or later your work will suffer. If you chose work relationship, sooner or later your friendship will suffer."

More than once, I have made this mistake. Erring in this way is also tied to wanting to be liked. Usually, there are one or two of your staff who are hard working, seemingly loyal and enthusiastic about their jobs. They become your "go to" staffers when you need something done right. Or you build rapport with a co-worker who is your org chart equal and assume it's ok to blow off some steam with this person now and then.

You will have to excuse the cynicism, but though these "confidants" may share their own frustrations with you and offer advice, most ultimately care about their own advancement. This statement is not to instill paranoia that all your employees are out to get you. The reality is if you and your boss are having issues and a co-worker or staff member knows something you did or said that could make you look bad and move them up the ladder, you're "toast."

It's worth mentioning that the more you talk to this person and feel like your confidence is being kept, the more likely you are to use text or email in your correspondence. Obviously, that only makes the situation worse.

As a boss, I have always wanted to have an "open door" and for employees to believe they can come with their problems. I think that is a healthy dynamic in the workplace as long as you keep their confidence, while choosing not to reciprocate by sharing your own issues.

Socializing with Staff

Like with most things, there is an important line not cross. Birthday celebrations at the office? Have a piece of cake. Sign the card. Go back to work. If George is having a retirement party at the pub down the street, go early, have a beer, say a word or two and go home. During the holidays, having a dinner party at your home for your staff and their spouses is a lovely thing to do, but manage the alcohol in-take and have a hard ending time.

What is not appropriate in my experience are one-on-one lunches with subordinates, male or female. If having one-on-one time with staff members is part of how you evaluate your team, then fine as long as everyone gets that same treatment. Cocktails after work with one or two is a bad idea. So is attending a party hosted on the weekend by an employee or socializing as couples.

The employment law firm of Landegger, Baron, Lavenant, Ingber says socializing supervisors can lead to :

  • "Lack of respect;
  • Decreased production;
  • Employees who are "friendly" with supervisors may be more prone to skate by and not dedicate their full resources to their productivity, attitude and attendance;
  • Favoritism;
  • Creates Liability;
  • Discrimination - gender, age, national origin as the supervisor may tend to socialize with employees with similar demographics."

What ultimately develops is the appearance of favoritism, rumors or accusations. Remember about co-workers as confidants? A few drinks, lunches or social outings and sooner or later you will let your guard down and say something the employee or their spouse should not know.

Employees and staff are not your friends and frankly neither are co-workers. That is not to sound cold and uncaring. There are plenty of friendships and long-lasting romantic relationships that have blossomed in the workplace. As boss, it is the right thing to do to know about your employees' families, things they may be struggling with in their lives and to help if you can within reason. As human beings, we can show kindness and compassion without the expectation of that kindness leading to a "friendship" that is disruptive to the office or our careers.

Use facts and data to back up tough decisions. When decisions affect someone's job or quality of life, they really don't care about your "gut" or intuition.

Wimp Out on Performance Evaluations

Other than having to fire or lay off a good person, giving someone a bad performance evaluation is a rotten thing bosses have to do. I admit to wimping out and giving a score of 3 (average) to someone who is really a 2 (below average,) because Joe is a "heckuva" nice guy and never takes a lunch. I have also been purposely vague about mistakes and corrective actions that need to be taken.

Nobody wins if you wimp out. First, Joe continues to believe he is doing at least an adequate job, while you continue to be frustrated by his work. Second, Joe is confused because he doesn't understand your frustration when you just told him he was doing a good job, Third, if bonuses or pay increase are tied to evaluation, eventually word will get out about who got how much? Joe's co-workers know he is not top notch and will resent that he got a bonus for sub-par work. It is not fair to Joe to think he's doing well, not fair to his co-workers and not fair to you.

"It's never easy to tell an employee what he or she needs to do to improve, but giving constructive criticism about your workers' performance is an important part of the review process. Be as clear and direct as possible about any shortcomings and mistakes, but also take the time to provide solutions to those problems," says Nicole Fallon Taylor with

Balance those failures by highlighting successes. Be clear about the step-by-step corrective action that needs to be taken. Schedule periodic check-ins to give feedback about whether or not progress is being made. Don't reward mediocre work. If your company culture is "everyone gets something," then make sure the mediocres get less.

Fail to Keep Records

Historically, this has been one of my worst failings. Why? It seems paranoid, it's time-consuming and I want to be liked, so I don't want employees to be intimidated. Unfortunately, in our litigious society and with many in the workforce that feel like they are owed something, it is in your best interest to keep meticulous records.

When it comes to contracts, performance evaluations, employment applications and supporting documentation, I have always maintained those files. What I have not always done is maintain a clear record of employee reprimands or sufficiently documented important conversations.

If you are meeting with an employee about an new initiative, changes around the office or new procedures, to the extent possible have another person in the room. Avoid one-on-one closed-door meetings, especially with the opposite sex. If the conversation requires a higher-level of privacy, consider using a recorder with both parties being aware that the device is recording. If that's too awkward or not your style, take detailed notes and periodically pause to read back what was said and ask the other party if you got it right. Following the meeting, type the notes and forward to the person asking them to respond in writing (via email works) that they agree that the notes fairly represent the conversation. Make sure those notes are backed-up and retrievable if needed. This doesn't have to feel "cloak and dagger" if you frame it in the context that the conversation is important and for the sake of the employee and the company, you want the employee's help in getting the details right.

Expect Loyalty

Unfortunately, too many executives and leaders put too much value on loyalty, especially if they are loyal themselves. Don't believe that because you remembered birthdays, visited sick members of your team, gave excellent performance evaluations or recommended team members for promotions that you can count on their loyalty. The moment you expect it is the moment you will be deeply disappointed.

From their perspective, who cares you remembered their birthday as long as their spouse or BFF did? No one asked you to visit when they were sick, and you probably felt obligated. They did the work to earn the performance evaluation and deserved the promotion. They don't owe you anything.

Truthfully, there are many loyal employees in offices around the world. Let them be the surprise, not the expectation.

Jeff Haden at distinguishes between loyal and remarkably loyal employees in this way:

"Remarkably loyal employees flip the employer-employee relationship: They know you want to help them reach their professional and personal goals and that you want what's best for them--and they also want what's best for you, both at work and in your personal life."


Some who read this will think, "What an idiot. Who makes these dumb mistakes?" Others will see the advice as "old school" -- the way companies were operated in the 60s and 70s -- and out of touch with the Millennial generation. As workplaces become more casual, more open and strive for less formality, it may improve co-worker dynamics relative to collaboration and innovation, but there is also more opportunity for conflict between bosses and employees. Regardless of the company culture, executives can avoid these seemingly harmless mistakes and strive for the highest level of professionalism.

Socializing with Co-Workers

Do you socialize with employees or co-workers outside of official office functions?

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