Hiring Managers Reveal: ‘The Biggest Mistake *I* Ever Made’


We’ve all had a forehead-slapping career moment—or two.

You blanked on an important meeting. You got caught badmouthing the boss, thanks to an unfortunate “reply all” situation. You were, shall we say, over served at the office party.

Unfortunately, we can’t turn your blunder into just a bad dream, or give you the power to travel back in time and do things differently. (Sorry!)

But what we can do is help you gain enough perspective to transform your stumbling block into a stepping stone.

Because, as trite as the saying “Everyone makes mistakes” may sound, it’s true: Even executives at the top of the food chain have made cringe worthy errors.

To prove it, we convinced five hiring managers to spill the juicy details of their worst career flubs—as well as how they recovered, and ultimately grew from the experience.

So next time you screw up big, take solace in their stories.

Mistake #1: Trying to Be a Superstar—at the Expense of Others

“In the late 1990s, I joined a management consulting firm as an ambitious new associate. I loved the work. Every day was a challenge, and the opportunities for advancement seemed endless.

However, I made the big mistake of putting my own agenda ahead of the team’s.

From the beginning, I figured that if I worked harder than everyone else, and came up with the most innovative solutions to strategic business problems, I would be consistently rewarded—but I couldn’t have been more wrong.

In my fourth year I was eligible for an early promotion, and I thought I would be a shoo-in. But the day before the official announcement, a partner pulled me aside to inform me that he didn’t endorse me for the position.

He told me, ‘I will fight tooth and nail to get you to work on every single one of my projects, but we can’t promote you to management until you can play the game.’ Then he sat me down and explained what I needed to do to be successful.

It was pretty simple: Stand out for what you do—not for how you act—make others around you look good, and never make a superior look bad to a client.

Our conversation opened my eyes to how I’d been behaving. Up until then, if I felt like I was right about something—and someone else was wrong—I said so, no matter where we were. Even though I never intended to put my coworkers down, the net result was that I often made them look incompetent.

So I readily took the partner’s advice—making sure to listen and collaborate with my team members, instead of putting my ideas into action alone. Sure enough, these changes made all the difference, and I scored the promotion just six months later.

It’s been 13 years since this happened, but I still think about it today—and make a conscious effort to be the best team player and manager I can be.”

—Josh Lindenmouth, 39, CIO for an H.R. services company, Baltimore, Md.

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Mistake #2: Being the Office Gossip

“I’ve made a lot of mistakes during my career, but my fatal flaw was always my blabbermouth. I’ve never been able to keep a good business secret.

When I was just starting out in entry-level positions, this translated to some of my coworkers not telling me things. But as I moved up the corporate ladder, the consequences were more severe.

I remember one time, in particular, about a year ago, when this bad habit of mine really came back to bite me. The general manager at my current company, a digital marketing agency, told me a juicy tidbit: A senior manager was leaving but hadn’t formally turned in his notice.

I just couldn’t keep this to myself; I had to tell my closest colleagues!

After a few days of spreading the word, I decided to share this piece of gossip with … the general manager himself! I had completely forgotten that he was the original source of the news.

I said to him, ‘Did you hear that so-and-so is leaving? That won’t be good!’ He replied, ‘Yes, I’m the one who told you … not to tell anyone.’

Needless to say, this did not go over well. Although I didn’t get fired, it was awkward. The manager lost a lot of faith in me, and it created some distance between us.

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This wasn’t the first time I had made this type of mistake, so what really hurt me was this pervasive feeling around the office that I couldn’t be trusted. That’s a hard perception to turn.

In the end, I learned a lot from the experience. I decided I didn’t want to be known as the office gossip anymore, and started to prioritize keeping people’s confidence—no matter what.

What I eventually realized is that when people trust you with their secrets—and you keep them—they begin to trust you in other ways. Fortunately, my new-and-improved outlook ultimately brought me more responsibility in the form of a recent promotion to senior manager.

This has also impacted how I view job applicants in interviews. I believe in fresh starts, knowing that people can make mistakes and bounce back from them—so I’m more accepting of candidates with a less-than-perfect job history. Hopefully, they can grow from their errors—as I have tried to do.”

—Matt Antonino, 40, head of product for a digital marketing company, Melbourne, Australia

Mistake #3: Playing Favorites

“My catering business has been highly successful from its inception—principally because of my amazing employees. However, this past summer, I nearly ruined the workplace dynamics.

I had a special connection with one of my employees because we’d migrated from the same part of Africa. We’d laugh at the same jokes, and shared similar family stories.

Unfortunately, this made other staffers resentful and promoted the (untrue) perception that I valued her contributions more than theirs. As a result, I began to notice some big problems among my employees.

For example, one staffer started to develop a spiteful and almost vindictive attitude toward others, and manipulated them by telling them false stories. This, in turn, led to poor service and increased client complaints. It really troubled me because she was ordinarily quite productive.

When I asked the employee what was going on, she told me that, due to what she perceived as my preference for someone else, she felt threatened and undervalued.

So I decided to call a staff meeting to set the record straight—and instituted new policies for expressing workplace concerns. I’ve also made it a point to try to connect and build a relationship with each team member.

In the end, I learned that good staff is difficult to find. If a company treats employees unfairly, it’s like driving around with one flat tire on your car. Sooner or later, your business will be severely damaged—or could even fall apart.”

—Patience Ose, 38, catering business owner, Toronto, Canada

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Mistake #4: Ignoring Interview Red Flags

“The biggest professional mistake I’ve made is hiring based on straight likability—in other words, wanting to give a nice person a shot at a job, regardless of whether they’re the right fit.

Don’t get me wrong—likeability is a key component, especially in sales, because you want to hire relatable people who can connect with clients. But it’s also extremely important to consider how well the company and role align with a candidate’s interests, overall capability and personal goals.

I learned this lesson in 2013 when my team hired an intern who we thought would bring a unique perspective to the department—even though he wasn’t a perfect match. While he was really intelligent, he was also a bit airy and rough around the edges, professionally speaking.

Well, we really should have paid attention to those red flags. This intern fell asleep during meetings, ignored the dress code, arrived late, and surfed the web whenever he lost interest in a particular task.

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As a result, I (along with several others) wasted a lot of time and energy on this person over the course of three months—only to realize we never should have hired him in the first place.

Two coworkers, in particular, invested many hours trying to foster his development, when they could have been making sales calls to grow our business. We also had to mend some workflow inefficiencies he created.

Fortunately, this was just a bad hire for a temporary position—not a permanent employee—so the consequences weren’t as serious as they could have been.

But I learned a valuable lesson nonetheless: While diversity of thought is a nice thing to have, it’s more important to suss out several key things while hiring—including whether a candidate is willing to seek help when needed, work on sharpening their strengths, and develop a passion for the role.

By making sure to ask the right questions, and heed any warning signs, I’ve definitely sharpened my own strengths when it comes to hiring.”

—Jennifer Reynolds*, 26, account manager, Dallas

Mistake #5: Forgetting to Toot Your Own Horn

“As a senior manager at my previous job, I hired over three dozen people and led a 15-person team. My leadership style was to focus primarily on the growth and well-being of my staffers.

And that was a smart strategy—to a point. On the one hand, it builds huge loyalty and productivity. But I overdid it to my own detriment.

Beyond my regular job duties, I obsessed about adding value to my team members. I took them out to monthly lunches, and scheduled regular check-ins to discuss how I was performing as their manager. I blindly believed that taking care of my employees would result in growth for me.

Instead, the fact that I failed to spend a significant amount of time networking with peers, influencers and clients outside of my own department hurt me. I was overlooked for key projects that could have increased my visibility with executives, and passed over for promotions I thought I had in the bag—twice.

When I finally spoke up and asked someone on the interview panel why I hadn’t scored the promotion, he told me the truth: My lack of political savvy and ability to market myself was holding me back.

Because of this gross oversight, I never grew to my full potential at that company, but it did spark an important lightbulb moment: If I want to grow faster, I have to appeal—and showcase my talents—to my boss, his boss, my peers and my boss’s peers.

Today, about a year later, I seek out strategic opportunities to reach out to people in my field, find ways to help them, and buy them an occasional coffee or lunch. Along with that, I also make sure to send my contacts periodic updates on my own accomplishments—as well as those of my company.”

—Balki Kodarapu, 40, career site C.E.O., Portland, Ore.

*Name has been changed.

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