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Work/Life: What in the world is my boss thinking?

On this episode of Work/Life, host Greg Nibler is joined by Ciara Pressler, author and founder of Pregame, to discuss one of the big topics many workers find themselves struggling with: Figuring out what your boss is thinking. Is there a way to hone in on how and what your boss thinks? Are there clues? How can an employee anticipate and understand what their boss is going to say or do?

In some cases, employees find themselves becoming the boss, and struggling with now managing a team of people doing the tasks they used to do, which requires an entirely different set of skills. Managing a team and being just part of a team require different hard and soft skills, and it can be eye-opening to employees who have only been on one side of that coin. Of course, communication is a big part of this, and there are ways to improve both interpersonal and business communication.

But if an employee is in the position of trying to deal with a boss they’re having a difficult time understanding, Pressler says there are some important things you can do to manage your situation. “First, know that your boss is human,” she says. “It may not seem like it all the time, but your boss has feelings and a life outside work,” and that can often take time and mental energy. To break through that, remember that an employee only has a small view of the very big picture of what a business is.

“So while it was up to me [as an employee] to advocate for what I needed in my department,” Pressler says, her boss needed to view the company as a whole. “There are a lot of things you just don’t know about.”

Nibler notes, “employees are one piece of a big puzzle,” and recognizing your position within the company as a whole can help attune you to where your boss’s thought process is.

Pressler has other tips for breaking through to your boss: “Don’t bring a problem without a possible solution, and why they need to get on board with your thinking.” Offer solutions that fit both your role, as well as the company as a whole. Understanding the context of problem-solving, as well as the different people and departments those solutions may affect can go a long way. “To the degree you can,” Pressler says, “figure in the other things happening at the company.”

Pressler also says that “Your boss really does want you to succeed.” It would be silly to think that (in most cases), your boss is there to make you fail, because then that would mean the boss is also failing. Remember: you’re all in this together. “What changed for me with hiring was that I got really clear on my company values, which is what figures the culture,” she said. When people have shared vision, it puts everyone on the same page.

Finally, Pressler reminds us to see how it all fits together. “You are on a team, and your boss is the coach. He makes final calls, but he’s there to support you.” Try to solve your own problems, be strategic, and respect your boss’s time. “It boils down to respect; you’re dealing with another actual person,” Nibler notes. When you’re able to see your boss as a person who is looking at a bigger picture, you’ll be able to anticipate the wants and needs of both your boss, as well as your company.

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