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How to Have the 'What's Next?' Talk With Your Boss

Advice from the 'Love Your Job' author on making work better for you

By Kerry Hannon

(This article is adapted from the new book, Love Your Job: The New Rules for Career Happiness by Kerry Hannon).
Sooner or later you’ll have to suck it up and have the “talk” with your boss. It’s unlikely that you will simply be handed a new opportunity without asking. But you can do this.
Here’s how to have that critical conversation you’ve been hearing in your head for so long:

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5 Questions to Ask Yourself Before the Big Meeting
Before having that talk with your boss, consider asking yourself these five questions:
1. Are you sold on what you’re asking for? You can sell it only if you yourself are persuaded. So consider — why you? Why now?
2. What exactly are you asking for? Can you say it in a sentence? Your pitch must be clear, simply stated, and delivered without setting the stage with a lot of preamble and throat‐clearing.
3. What are your boss’s challenges right now? Do your research to get a feel for what your boss faces before you go for the “ask.” This will let you anticipate potential pushback.
4. Can you do your presentation in your sleep? Spend as much time as you need to get it down to a convincing “conversation” that lets you smoothly deliver your well‐thought‐out pitch.
5. How quickly do you realistically want, or need, something to happen? The earlier you can start a conversation about a change you would like to make, the better your chances of getting the result you’re after.

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Your PlanandPrepare Strategy
Now, consider these four steps before you talk to your boss:
Step 1: Figure Out What’s In It For Your Employer
Ask yourself: How can the company benefit from helping you do something different? How can your boss professionally win from it? Is it going to cost your company anything in terms of money, time or personnel changes?
Think strategically and build your case by explaining clearly how your boss and your department can benefit, and do everything you can to make the transition easy for them.

Step 2: Talk to Colleagues Who’ve Made Similar Changes
If you handle conversations with colleagues gracefully, you can find out lots of information. Was their boss supportive? Did the HR department help pilot the change? If you’re asking for a flexible schedule, talk to others who have similar schedules and find out about company policies.
Step 3: Tweak Your Elevator Speech
Practice explaining what’s pushing you to want to take this step. Why are you best suited for this? How will the new duties ramp up your skills and make you a more valuable employee or tap into your existing skills in ways you haven’t been able to showcase?
Step 4. Schedule a Formal Meeting
Don’t wing it. In your formal presentation, pay attention to your posture, make eye contact and smile. Give the boss time to consider your request and to get back to you. He or she may need to get permission from above or just get comfortable with the changes you asked for.

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Carrying Out the “Ask”
Now let’s talk about some specific questions and challenges that might come up in your discussion.
“Improved efficiency” should be at the top of your “why you should let me have a flexible work schedule or telecommute” list.
Walk into the conversation with a proposal that describes what your work schedule would be, the number of hours you would work, how unplanned overtime would be handled, how often you would check in with an office visit and how often you would talk with your boss.
To seal the deal, ask for a trial period of three to six months so both you and your boss can see how the arrangement works out and fine‐tune it if needed.
If you’ve been in your position for a while and have taken on extra responsibilities, ask about a promotion. Or consider a title change or revision to your job description, which may help get you the recognition and respect you’ve wanted.
If you can’t move up, offer to work on something that is not part of your day‐to‐day responsibilities. Explain how your new responsibilities will help the company. Perhaps you’ll be able to bring a fresh perspective, produce creative ideas, or provide experienced leadership to a particular project.
Don’t say: “I’m bored, frustrated and having trouble seeing how I can advance in my current position.”
If you’re interested in continuing your education, ask your boss if she would support your desire to take a workshop or go back to school for a certification or an advanced degree. See if she would be willing to give you some flextime to help you fit your studies into your schedule and whether your employer could pay some of your tuition.
Another way to ramp up your inner game is to seek out a mentor or sponsor. If your employer doesn’t have a formal mentoring arrangement, let your boss know that you’re interested in being connected with someone senior or with more experience. Many coworkers are eager to lend a hand and finding one just might help you love your job more than you do now.
Excerpted with permission of the publisher, Wiley, from Love Your Job: The New Rules for Career Happiness by Kerry Hannon. Copyright (c) 2015 by Kerry Hannon. AARP is a registered trademark. All rights reserved. This book is available at all bookstores and online booksellers.

Photogtaph of Kerry Hannon
Kerry Hannon is the author of Great Pajama Jobs: Your Complete Guide to Working From Home. She has covered personal finance, retirement and careers for The New York Times, Forbes, Money, U.S. News & World Report and USA Today, among others. She is the author of more than a dozen books including Never Too Old to Get Rich: The Entrepreneur's Guide to Starting a Business Mid-Life, Money Confidence: Really Smart Financial Moves for Newly Single Women and What's Next? Finding Your Passion and Your Dream Job in Your Forties, Fifties and Beyond. Her website is Follow her on Twitter @kerryhannon. Read More
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