How to Ask Your Boss to Pay for Continuing Education

UPDATED: March 25, 2024
PUBLISHED: March 25, 2024
Woman in blue sweater studying at computer

It’s no secret that businesses that support continuing education for their employees experience higher levels of stability. From workshops to conferences, skill-enhancing opportunities help employees rise in the workplace, stoking a culture of growth linked to higher retention rates.

Although the mutual benefits of professional development are widely recognized, how to ask your boss to pay for continuing education can be tricky.

How to ask your boss to pay for continuing education

Shannon Gill Dayhoff, executive coach and founder of GVG, a leadership advisory practice, says to start by doing your homework. “What is offered by your organization, and what are the terms? How do you plan to use the assistance?” are some questions you should be able to answer.

Learn all you can about company policies and requirements and seek advice from those who have already tapped company resources for continuing education, she says. Having done your research beforehand will prepare you for questions raised in conversation.

Dayhoff, who spent more than 20 years leading successful teams inside startups and Fortune 500 companies prior to launching GVG, underscores the importance of timing. First, make sure you’ve been in your role long enough to prove your value—a minimum of six-nine months is appropriate, according to Dayhoff.

It’s logical to raise the topic of ongoing education in development conversations, whether it’s part of a performance review or a meeting on the books to discuss your career path. She points out that another natural time is during budget planning when funds can be earmarked. But don’t regard this as a one-and-done discussion; instead, seek to open the door to collaborative, ongoing conversations.

Be sensitive to your boss’s workload

Be savvy and read the situation. Put yourself in your boss’s shoes to gauge their mindset using your emotional intelligence, Dayhoff advises. Ask yourself, “Are they up to their eyeballs in hot projects or problems?” If they’re distracted and stressed, she suggests shelving the topic to raise later.

“The key is to make this as easy as possible for your leader to say ‘yes,’” she explains. One way to create that “easy button” for them is to recognize concerns they may have and potentially raise them to show you’re considering things from their perspective. Assure them, for example, that because a program is flexible, it won’t interfere with your workload.

Be savvy, avoiding even a hint of entitlement or you’ll make your boss defensive, Dayhoff adds. Instead, adopt a tone of honesty, transparency and humility, remembering this is foremost an influence conversation.

“Think about the WIIFM (what’s in it for me) for the leader,” she suggests. Connect the dots for them, explaining how your professional growth will benefit the company.

Ultimately, be encouraged. “Leaders want team members who take responsibility and control for their own career,” Dayhoff says.

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