Referring to the questions as "the three Ws," BAM Communications founder Beck Bamberger says she never wants to wonder, "What are you doing? Why are you doing it? When will it be done?"
As the CEO of a communications firm, Bamberger says her company is constantly holding clients accountable and managing expectations. Communication is key to keeping everyone on the same page.
"Communicate these [questions] constantly to your clients, team and me, and you'll be golden," she said.
Cuban agreed with Bamberger and tweeted that her advice was "spot on."
Rosemary Haefner, chief human resources officer at CareerBuilder, also agrees that communication is key to winning over your boss.
"Clearly communicate the details of your assignments so your boss is more aware of what is on your plate," Haefner tells CNBC Make It. "You cannot assume that your boss understands the hours associated with assignments. Making him or her aware will help create mutually agreeable expectations."
In 2015, millennials like Bamberger became the largest population in the U.S. labor force, leading to more young professionals taking over leadership positions. Kerri Rogan, head of reliability improvement for the transit system company London Underground, says the key to helping colleagues get adjusted to a young manager is to demonstrate that you're there to help.
Young managers, says Rogan, should try not to challenge the technical knowledge of their more experienced colleagues.
"You need to build personal relationships," she says.
Disclosure: CNBC owns the exclusive off-network cable rights to "Shark Tank," which features Mark Cuban as a panelist.
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