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How To Talk To Your Boss About Your Career Goals

You’ve got big dreams. Your boss can help you get there. Here’s how to have that conversation.

How To Talk To Your Boss About Your Career Goals
[Photo: Jacob Ammentorp Lund/iStock]

When you’re making big plans for your career, it helps to have a mentor as well as a champion. Having access to someone with company experience, insight, and information can also help you get ahead.

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Sometimes, you need just one person to deliver those benefits—your boss.

“Sharing your goals with your boss may seem like a risky proposition, but with thought, it can provide you with greater opportunity and a stronger relationship with your manager. This can also add employee retention value to the company, as employees usually stay longer with a company that shows it is willing to invest in its workforce’s development,” says Elaine Varelas, managing partner at Keystone Partners, a Boston-based career management firm.

But if you have a boss who’s open to helping you, how do you talk about your goals without making them feel threatened or like you’re preparing to leave? It’s a mixture of timing, framing, and communication skills.

Setting Yourself Up for Success

If you’re going to have a sit-down with your supervisor to enlist them as an advocate to help you achieve your goals, you want to give yourself the best chance at having a successful encounter, says Raleigh, North Carolina-based therapist and motivational speaker Tasha Holland-Kornegay, PhD. Find a time that works for your boss—no immediate deadline or other pressure—and when you’ll be able to get the length of meeting you need to discuss your goals. Holland-Kornegay also says it’s a good idea to give your boss a heads-up about what you’ll be discussing so they can think about how to help you. Recently, one of her employees reached out to her for a conversation about her own career growth.

The employee had been keeping pace with the increasingly busy practice, but Holland-Kornegay didn’t realize the additional demands that were being placed on this employee. After the conversation, Holland-Kornegay adjusted her pay, and they had a frank discussion about moving her career forward. “[From an employee’s perspective], I think you just have to be tactful and honest. And also be prepared. Go in there, say what you mean and mean what you say. And also let the employer know, I’m coming in here for support. I’m eliciting your guidance. I’m not trying to take anything away,” she says.

Saying The Right Things

Framing the conversation properly is another essential element to success, says Yardley, Pennsylvania leadership expert Liz Bywater, PhD, author of Slow Down to Speed Up: Lead, Succeed, Thrive in a 24/7 World. Spend some time thinking about how your boss may be able to help you achieve your goals, and prepare to show that you’re ready for stretch assignments, training, or other activities that can help you get to the next level. Bywater recommends starting the conversation in a positive way, quantifying that you’ve spent some time learning your job and about the company. Then, ask to explore ideas for career progression.

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Before he became president and owner of Sanford Rose Associates–Santee (South Carolina), John Malloy was president of a component manufacturing company with about 400 employees. He recalls one employee who took ownership of his career development, approaching Malloy about how he could get better at his job and get promoted. “He’d probably been with us only 90 days. And he came in and said, ‘I want to make sure I’m doing all the right stuff. What are the things that I need to be doing to please you and help the company?'” he recalls.

Malloy wrote down six key points, and the employee asked when they could review them again. A week before the appointment a few months later, the employee called to remind Malloy of their meeting. The employee arrived at the meeting prepared with what he had accomplished and contributed, and was ready for his next set of tasks and development opportunities. Malloy says that if an employee takes such an active role in their own career development, it’s hard for leaders to not pay attention and provide more opportunities that will ultimately bring value to the company.

“If they don’t want to hear what your goals and aspirations are, you’re working for the wrong person,” he says.

Avoiding Minefields

It’s important to understand organizational and leadership goals to have these conversations, Holland-Kornegay says. Know your boss’s personality and try to understand what might appear to be threatening, especially if your organization doesn’t have a clear emphasis on career paths.

Because conversations about aspirations, career, and money can sometimes be stressful or emotional, she recommends rehearsing what you want to say and possibly keeping some notes nearby to keep you on point. Managing your emotions is important, especially if you’re asking for help to advance your career and take on bigger roles.

Perhaps you really want your boss’s job or to learn what you can and then start your own business. Be careful, cautions Malloy. Some leaders will enthusiastically encourage such frankness, but others may find it threatening. Listen to how your supervisor talks about other people who have advanced or gone on to other opportunities to get a sense of how well this type of honesty will be received. Also, if your company is struggling, being assertive about advancement may be challenging, especially if the firm is cutting head count.

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“Any good boss will say, ‘I want somebody that can take over for me so I can advance.’ In larger companies, this is pretty easy. In smaller companies, it’s a little bit different, but even many smaller companies are growing,” he says.

Once managers understand the skills you’d like to develop, as well as your long-term career goals, and the areas of the business that hold the most interest to you, they can look for assignments, projects, coaching, and other opportunities to help you grow your skill set.

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About the author

Gwen Moran writes about business, money and assorted other topics for leading publications and websites. She was named a Small Business Influencer Awards Top 100 Champion in 2015, 2014, and 2012 and is the co-author of The Complete Idiot's Guide to Business Plans (Alpha, 2010), and several other books

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