“Behind every bad idea is an executive who asked for it.”

After holding 53 jobs in my life and my months of research to write “Mean People Suck”, I penned this quote. Besides my love for my family, it’s one of the few things I know to be true in life.

I’ve been there. I have known my boss sucks. I also knew I needed that job, but I wasn’t sure how to go about covertly making my boss change their management style. It’s a problem many of us have faced. It is easy to feel stuck, but with some self-reflection and by asking the right questions, you can help your boss be more compassionate.

Show them the money

How do you explain the importance of empathy to executives who don’t have any? That’s a joke, but there is no question that empathy is in short supply in most organizations.

The answer is simple. Take some advice from the movie Jerry Maguire and show them the money! In many businesses, the bottom line-driven executives aren’t persuaded by the idea of empathy as a means to increase revenue after the first pitch. Naturally, profitability and revenue drive most bosses to encourage certain ideas at work. Or it is their egos that make them think they know better?

Research indicates that creating an empathetic work culture is critical to employee happiness and retention. In fact, 77% of workers would be willing to work more hours in an empathetic environment, while 60% indicate they would take a cut in salary to join such an organization. Ninety-two percent of human resource professionals say a compassionate workplace is a significant factor in employee retention.

Some may scoff and say this sounds like the research only looked at millennials, but it spans multiple generations. It turns out that 80% of millennials would leave their current job if the environment became less empathetic while 66% of Baby Boomers would do the same.

And still, it remains a tough sell to many executives. Too many managers and leaders are skeptical about using empathy as a true business asset because its business contributions might seem abstract. Unfortunately, these managers tend to think of their employees as disposable.

The truth is, change begins with the people surrounding managers who have yet to be sold on the concept. It starts with you and your ability to recognize the right moment when to push back and start selling your boss on empathy.

Mastering the push back

The push back challenges managers to think outside their comfort zones, and simply challenging our bosses’ bad ideas creates a more efficient company culture. It will disrupt the Illusion Point, meaning it’s the first step in getting rid of tasks you know don’t work. By pushing back, we put the onus on our managers to explain why our ideas aren’t being taken more seriously when we know they’re valuable ones. When we approach our push back in a strategic way, our bosses will buy into the success we’ve shown them.

I’m sure it sounds scary but I promise you it’s worth it. Here are the steps:

Step 1: Examine the past.

By this I mean think about the times you have wanted to take an idea to your boss. Did you feel comfortable doing so? Or did you immediately assume your boss would not go for it? When you start recognizing that certain tasks or projects won’t work, also known as the Illusion Point, do you go along with it or do you challenge your boss?

Obviously, you don’t want to put yourself at risk by stepping too far out of line. It is time to ask yourself how you can strategically challenge your manager without coming across as too pushy or unprofessional.

Step 2: Put your journalist hat on.

Journalists know the right questions to ask to get the story they’re after. That’s why I recommend you do the same.

You want to prioritize your ideas at the moment, while also challenging your boss to think critically about why they’re not receptive to your ideas. Once you recognize the Illusion Point—when your manager suggests counterproductive, status quo ideas to accomplish a goal—push back by asking three simple questions to stop a bad idea right in its tracks.

Question #1: Why does this matter?

Asking why an idea or project is important forces your boss to get clear before the implementation starts. It can open the door for more conversation and perhaps a better understanding between you and your boss. From the boss’s standpoint, that helps build a culture of empathy, too. Being in the know keeps employees more satisfied and keeps managers on their toes. When employees ask why an idea matters, it helps bosses be better bosses.

Question #2: What’s the impact?

This question shows that you are aware that a new idea may change the customer experience. It demonstrates that, even if your manager is excited about an idea, it’s still problematic if it doesn’t work for the customer.

Asking about an idea’s impact also makes it clear you know what’s expected of you as you execute that idea. It shows how important it is for you and your boss. If you’re expected to deliver certain results for your customer, you should have a good handle on what those results look like. If there’s a disconnect between what your manager wants and how you think the customer might react, this is the question to get that conversation started.

Question #3:  How will this be measured?

Everyone wants to be good at his or her job, and our managers want us to be good at them, too. But being good at our jobs requires a certain level of clarity. For bosses who don’t usually discuss the meaning or impact behind an idea they’ve proposed, the milestones they want us to accomplish probably aren’t all that clear, either. That means the intended result can be something of a gray area.

To accomplish that bigger goal, we need to solidify the milestones in the middle. Knowing the details of what your manager expects when you’re executing that idea in real time matters. The end goal might be admirable, but what good is executing an idea well without a measuring system to track that success?

Close the sale

By following the steps and asking the right questions, you are starting a dialogue with your manager while also showing you care about your work. Not only will this eliminate projects that won’t work, but by pushing back, you are helping to create an empathetic culture. No one wants to work for a company that sucks.

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