Asking for a raise or promotion at work doesn't have to be an awkward or painful experience -- a lot of it comes down to simply knowing how to put your best foot forward and asking in the right way, at the right time.
The Jamaica native, who currently lives in New York City, is a negotiations supervisor for a debt settlement company. The next level up is negotiations manager. She said she already manages a team of eight people at the moment, but believes she can lead a team of 120.
"I have had a managerial role before," Elesia told Corcoran and Herjavec in a mock interview. "It wasn't as many as 120, in all honesty."
Show that you have the experience to thrive
The "Shark Tank" stars recommended Elesia package her skills to really flex that she has experience as a manager when asking for that promotion.
"You could package that like, 'I’m well-acquainted with managing people. Every time I've been put in charge of a group of people, I've exceeded expectations,'" Corcoran said.
Herjavec added that: "Anything you can do to illustrate your background in those areas is really power."
Do not devalue yourself
When asked by Corcoran, "Where would you rank yourself, among the top, or in the middle somewhere?" Elisia responded with "among the top."
For Herjavec, telling your boss that you are "among the top" is not good enough.
"You've done a really great job," he said. "But your value proposition is basic ... You're telling me you're not the very top but you're near the top."
Start with tangible evidence for why you should be promoted
As Corcoran and Herjavec continued mock-interviewing Elesia, it wasn't until later on in the conversation that they say they uncovered the most important things to mention when asking for a raise.
"If the other person generates more fees, why wouldn't it just give the promotion to them?" Herjavec asked her.
Elesia responded quickly, "Because we've settled more debts than the other team."
Herjavec recommended that she start with this, saying, "That was good, and it was tangible."
Mentioning that her team has settled the most debts out of any other team should be mentioned first when asking for a raise, according to Corcoran.
"That should be your byline walking in," Corcoran said.
In addition to your experience and how you present yourself, a lot of the game is asking for a raise at the right time, according to Corcoran and Herjavec.
Here, the two break down what to know about when is the best and worst times to ask your manager for a raise.
The best time to ask for a raise
The ideal time to ask for a raise is "when the atmosphere is happy," Corcoran said.
"Most people go and ask for a raise when it's review time. I don't think that's the right time. I give the biggest raises when sales were great," she added. "We just had a big party, we spent a lot of money, we're all happy."
Herjavec added, "The person you're asking is a human being so you've got to get them in a good mood."
"Do it in a time of day that works for the other person. I like doing it in a more social setting if I can get that in the cafeteria," Herjavec added, suggesting asking your supervisor, "Can we go for a coffee?”
Wherever you choose to do it, Herjavec recommends making sure the other person feels comfortable when you start asking them for a raise.
"If I'm uncomfortable someone's asking me for a raise, then they're probably not going to get one," he said. "It should seem natural to me."
"I almost want to feel guilty that I didn't give you a raise because you're so valuable," he added. "The best people who get a raise from me are the ones, when they sit down and they start telling me what they're doing for us, and my first reaction is, 'I can't believe I haven't given them a raise.'
The worst time to ask for a raise
"Don't do it on a Friday afternoon. Because what am I thinking on a Friday afternoon? I want to go home," Herjavec said.
Herjavec also recommended not asking for a raise "before lunch."
Corcoran agreed that Friday is not the way to go, saying, "That's when I fired everybody, Friday."
Make a one-on-one meeting with your boss
If you want to set up a one-on-one meeting with your boss to ask for a raise, Herjavec recommends asking more than a day in advance.
"One thing that drove me crazy, and it happens much more than you'd expect," he said, "People would just meet me on a Thursday and say, 'You have some time tomorrow, I wanna talk with you?'"
"And then they come and hit me for a raise," he said. "I hate that, it's like no respect."
"I like, 'When you have time, could I put a date in my book?'" he said. "Then I feel like, well, I'm very important, and they're giving me enough lead time. And what do I do in that lead time? I start checking them out and seeing if they deserve a raise, because I know it's coming. And they’re more apt to get the raise."