Doing business means taking calculated risks.

Regardless of whether you are opening a lemonade stand or you’re a leading executive at a Fortune 500 company, risk is an inevitable part of the game.

Taking bigger risks can generate proportional rewards – and sometimes, such as for the companies you’ll read about below, the risk-taking backfired to queue up some of the biggest bankruptcies in U.S. history.

Going For Broke

Today’s infographic comes to us from TitleMax, and it highlights the 20 biggest bankruptcies in the country’s history.

Companies below are sorted by total assets at the time of bankruptcy.

There are times when companies are forced to push in all of their chips to make a game-changing bet. Sometimes this pans out, and sometimes the plan fails miserably.

In other situations, companies were actually unaware they were “all-in”. Instead, the potentially destructive nature of the risk was not even on the radar, only to be later triggered through a global crisis or unanticipated “Black Swan” events.

The Biggest Bankruptcies in the U.S.

Here are the 20 biggest bankruptcies in U.S. history, and what triggered them:

The data set on the biggest bankruptcies is organized by assets at time of bankruptcy. Therefore, they are not in inflation-adjusted terms, meaning the list skews towards more recent events.

This makes the impact of the 2008 financial crisis particularly easy to spot.

The events and consequences relating to the crisis (loan defaults, illiquidity, and declining asset values) were enough to take down banks like Lehman Brothers and WaMu. The after effects – including a slumping global economy – led to a second wave of bankruptcies for companies such as GM and Chrysler.

In total, nine of the 20 biggest bankruptcies on the list occurred in the 2008-2009 span.

A Dubious Distinction

You may also notice that one company was on the list twice, and this was not an accident.

Pacific Gas & Electric, a California company that is the nation’s largest utility provider, has the dubious distinction of going bankrupt twice in the last 20 years. The first time, in 2001, resulted from a drought that limited hydro electricity generation, forcing the company to import electricity from outside sources at exorbitant prices.

The more recent instance happened earlier this year. Facing tens of billions of dollars in liabilities from raging wildfires in California, the utility filed for Chapter 11 protection yet another time.

Being a leader comes with great responsibility.

Not only are you accountable for the success of your division or organization, but your team is also constantly reliant on you for feedback, coaching, and guiding personal development.

While juggling these priorities, it’s not always easy for a manager to know the exact right thing to say to employees on the team. To further complicate matters, we all have bad management habits that have compounded over time, and they can be difficult to shed.

Building a New Lexicon

Today’s infographic comes to us from Headway Capital, and it highlights 11 things that leaders should never say to their teams.

More importantly, it breaks down the negative implications of each instance, while also providing suggestions on how we can evolve our managerial skills to ensure that we are approaching each situation far more proactively.

Life as a leader is busy, and it has many competing priorities.

However, to grow the type of company culture that pays long-term dividends, it’s worth it to try and better develop the way you give feedback to team members.

Typical Mistakes

Using the list of items in the infographic, we can generally categorize these mistakes in a few distinct categories.

1. Gut Reactions

The quick dismissal of someone’s effort (“That’s not important”) or the temptation to play the busy card (“I don’t have time to talk right now”) can send the message that an employee’s time or thoughts are not valued.

Instead, small adjustments can be made to encourage better outcomes. For example, you could make it clear that while you may be busy in the moment, that a time can be scheduled at a later date to discuss the issue in detail.

2. Business Truisms

Likewise, spouting overused, quasi-motivational business phrases (“Failure is not an option”) or using dictative language (“We’ve already tried that before”) can stifle innovation at a company.

It’s better to instead ask questions, such as “What is our backup plan if this idea doesn’t work?” or “What other options do you see?”, to expand the range of opportunities that can be pursued.

3. Generic Feedback

Finally, although phrases like “Keep doing what you’re doing” or “Nice job today” seem to be positive and engaging, they actually are ineffective from a development perspective.

Employees need specific feedback to grow, so all that has to happen here is to mention a specific task or project along with the feedback. Team members can then internalize precisely what made a project or task a success, and apply it to other areas in the workplace.