Three Lessons Learned from the Worst Bosses I've Ever Had

Let’s face it, we’ve all had shitty bosses. If you’ve had one, I’m sure you can visualize him/her with ease and recall why they were terrible. If you haven’t had one, I’m sure you will at some point in your professional career.

For the sake of this blog entry, I’d like to focus on those of us who’ve had a shitty boss. It’s easy to trash the worst boss you’ve ever had. Whether they treated you like a 2-year-old, micro-managed you to death, stole credit for your work, didn’t trust you or down right harassed you, the list can go on and on. The last thing you want to do is remember that person. Yet, I think it’s important to do just that – remember them. Specifically, remember what they did wrong.

Too often I think people reflect on the best bosses they have had and the qualities they held. There is nothing wrong with this, but I find tremendous value in learning just as much from the worst bosses you’ve had as the best bosses you’ve had. With that said, here are three lessons I learned from the worst bosses I’ve ever had…

Lesson 1: Understand the Team Morale

I had one boss who simply could not understand team morale. Specifically, the team I was on was under a lot of stress, both professionally as well as personally, had a lot of pent up frustrations on work-related matters and was seeking clarity on a number of issues within the company.

Rather than address those issues, try to ease concerns and attempt to alleviate those frustrations, this boss decided to focus on their own work. As team morale took a nose dive, I couldn’t believe my boss was that naïve to not see what was going on. It was as if, their priorities were greater than the teams and that didn’t sit well with me.

I realize not everyone is able to empathize or pick up on visual cues from team members, but I believe if you’re in a supervisory role, it is your job to do so – or at least try. Thus, from this experience, I firmly believe in taking the time to understand your team dynamics and morale. Not only from a skill-set standpoint but also from an empathy standpoint.

How can you do that? Have 1-on-1 conversations with each team member, have weekly team meetings, have informal conversations not pertaining to work. Show your team members that you care about them and their concerns. Admit your weaknesses and ask for help. Send reaffirming emails. Go to happy hours. Reiterate the notion of work/life balance consistently. I realize some of these will work for you and some may not, but the important message is that you try. Be there for your team because at the end of the day, you need them more than they need you.

Lesson 2: Micro-thinking leads to micro-managing = Bad Managing

One boss I had simply could not get out of micro-thinking. Whether it was pertaining to client work or from a company standpoint, they could not seem to think about the bigger picture. They were so focused on minuscule matters and their own agenda, that it led to micro-managing and overall bad management.

It hurt our efforts with the client because rather than being pro-active and looking at the bigger picture of the client’s goals, we focused way too long on tactical details and matters that weren’t important.

Additionally, the micro-thinking led to micro-management which built a lack of trust within the team. As an example, the mentality became, you didn’t have to worry about doing your very best work because you knew the boss would just change it to what they wanted. Rather than the boss helping the team understand the direction they wanted, they just did the work. This led to resentment and lack of effort.

So, how can you fix that? If you’re the boss, be sure to lay out clear objectives and goals with any task that is assigned. Ensure the team clearly understands the bigger picture and let them go to work. You hired your team for a reason – they are talented and smart, so let them do the work. If changes need to be made, make sure you explain your thought process, so they can learn from their mistakes and do better on the next task. Yes, there will be times when a deadline is tight but at the end of the day, the more you help your employees become better at their craft, the more likely they are to help you in the long run.

Lesson 3: Don’t Be an Asshole

This one should be obvious but apparently, it needs to be restated. I had one boss who fired two employees on separate occasions on a Monday. A MONDAY! That means instead of letting these employees know on Friday and give them the weekend to process their next steps, they made them make the commute into work, believe they were starting a new week fresh and THEN, decide to flip their world upside down. I couldn’t believe it.

In another example, I had a boss that thought they were hot shit about everything. It was their world and we were just part of it. If there was a picture next to the definition of arrogance, this boss’s face would have been there. Were they talented? Yes. However, they refused to engage in healthy debate, often belittled employees and were just, well, an asshole. I’m sure they are still an asshole today.

So, what did I learn? In management roles, I’ve tried to remember to be grateful, patient and communicate effectively. Assholes aren’t grateful. Assholes surely aren’t patient and they often suck at communicating. I think a lot of that stems from insecurities the asshole bosses have. Put them in a position of power and there is no telling how much they will abuse that power. Thus, if you are the boss, try to be understanding. Try to uplift instead of tear down. Try to listen vs. always be the one to talk. Try to delegate vs dictate. Most of all, try to be positive vs. an asshole.

In closing, you can learn a lot from the worst bosses you’ve had in the past. I know I have. Rather than talk trash about them, identify what you can learn from what they did poorly. It will make you a better boss down the road.

How Chrissy Teigen Almost Cost Me My Job - And What I Learned From It

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One celebrity. One tweet. One mistake. Three lessons learned. This blog entry is dedicated to every Social Media Community Manager out there trying to do their job to the best of their ability. Mistakes happen, and I lived to tell the story…

Backstory:
It was February 2014 and I was the Community Manager for the brand White Castle on Twitter. White Castle is a well-known, established brand, that has a loyal fan following. Their competitors included McDonalds, Taco Bell, etc.

My job was to respond to any and all (@) mentions for White Castle, search for “White Castle” conversations for surprise and delight opportunities and engage with fans when appropriate. Additionally, utilize social listening tools to identify key influencers that I could potentially engage with as the brand.

At the time, White Castle’s tone of voice on Twitter was lighthearted and playful. Witty with a heavy sprinkle of sarcasm was the goal. Thus, engaging with fans was a lot of fun – especially when you get a celebrity interaction.

The Initial Tweet:

On this particular day, I had made it a personal goal to interact with a well-known celebrity. I’m sure every Community Manager has had the same goal at some point. Yet, the likelihood of a celebrity mentioning a brand back then was still relatively by chance. Lucky for me, Chrissy Teigen happened to be tweeting about food that day and I saw an opportunity. So, I went for it. Here was the initial tweet….

The Mistake Tweet:

SHE HAD TWEETED BACK! I was thrilled. Ecstatic! This was going to be a big win for the month and for our team. "I had to keep the conversation going" I screamed internally! In the spur of the moment, I replied back with what I thought was a good response and hit SEND. Here was the tweet…

I didn’t even think twice. I was so excited that Chrissy had responded that I didn’t realize what I had done. Then, it happened.

The Aftermath:

Taco Bell. Fuckin' Taco Bell with the grammar burn. Once Taco Bell called White Castle (aka me) out, the Retweets and Likes (favorites at the time) on their tweet went nuts. I don’t want to use the word viral because it wasn’t to that level but from my vantage point, it felt like that.

As the engagement skyrocketed with people making fun of the error I had made, I told my boss what was going on. He immediately checked the conversations that were occurring and noticed the high level of traction this was receiving. Keep in mind, Taco Bell had a very large following on Twitter at the time, so this wasn’t going to go away quietly.

To his credit, my boss didn’t panic but I could sense his anxiety level rising. We immediately brainstormed ways to try and spin this error in our favor but we struggled for a solution. Ten minutes had passed, and the conversation was only getting louder. We decided to bring in another team member to try and come up with a solution. Another ten minutes had passed, the conversation online still going.

At this point, some of you may be wondering, “Why were you so worried?” To start, this was my first real mistake with White Castle and with the level of influencers involved (i.e. Chrissy and Taco Bell), my mistake was amplified greatly. Second, if mistakes created enough noise, major advertising publications would pick it up and showcase the mistakes in articles such as “Twitter Brand Fails of the Week” etc. No one wanted to be part of that! Lastly, our internal White Castle social team had made a few large-scale mistakes in the past and I was brought on the team to help ensure those didn’t happen again. Would this mistake be the tipping point to costing us the account? Would this cost me my job?!?! Thus, we didn’t want to bring it up to the client.

After approximately 30 minutes, we came up with a plan to respond on Twitter and hopefully quiet the chatter. Here was the response…

Was it the best response? No. But, it was the best idea we could come up with at the time.

As the day went on, the conversations around the mistake continued and we realized the client needed to be notified. So, my boss and I crafted an email outlining what had happened and crossed our fingers that the client would understand. Thankfully for us, the client responded that it was an honest mistake and that they were happy with the initial effort to jump into a conversation with Chrissy. A deep sigh of relief ensued.

The Lessons Learned:

Thankfully, we didn’t lose the account and I didn’t lose my job because of my mistake. However, with any mistake, there are lessons to be learned. So, what did I learn?

Lesson 1: The Value of Social Listening

Had I not been in tune with the conversations occurring on Twitter and checking Chrissy Teigen's account, I may have missed this opportunity. I was able to see an opportunity to jump into a conversation and capitalize on Chrissy's tweet. With that said...

Lesson 2: Double check your work

People who work in social media, particularly Community Managers, work in a very fast paced environment. If you manage a large scale brand and are constantly engaging in conversations online, be sure to check your work before hitting "SEND." Especially when you are engaging with a key influencer. 

Lesson 3: Own your mistakes

There was a moment after I had made my mistake that I thought, maybe it will just go away. Maybe I wouldn't have to tell my boss. Well, thank God I did. Not only did the mistake intensify throughout the day but I also needed him and others to help come up with a solution as well as navigate the conversation with the client. In hindsight, I was happy I owned up to my mistake because had I not, it may have cost me my job.

Conclusion:

It has been over 4 years since this incident but not a day goes by that I don't remember that tweet. I use this example in interviews. I use it when I'm training new Community Managers. I use it as a reminder to move quickly but hit SEND slowly. Most of all, I use it as a reminder of the joy I have in working in social media. I can say I had an interaction with Chrissy Teigen, who is now in my opinion, Queen of Twitter. So Chrissy, if you read this, thank you for this memory. 

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