Making the decision to seek a flexible work schedule may be easy when the time and situation are right for you and your family. Figuring out how to ask your boss for the flexibility you desire can be a completely different story. However, if you prepare well and approach the situation thoughtfully, you can succeed.

Here are a few steps you may want to follow as you prepare for and follow through on that challenging conversation.

  • Ask yourself some questions. Why do you want a flexible schedule? What are your goals? What kind of flexible work option do you want or need?
  • Talk to your family. Make sure your plans mesh with what will be best for them.
  • Choose the flex work option that will work for you. Do you want to work from home every day? Shift hours to avoid traffic? Telecommute once or twice a week? Make your choice and use it as the basis for the rest of the process.
  • Evaluate your job. Which of your tasks can or cannot be completed at your home office? How long does each of those tasks take? Be specific and detailed.
  • Catalog your workspace. If you’re hoping to work from home, your boss will want to know what kind of equipment and technology you’ll be able to use. Again, be specific.
  • Check with human resources. Your HR department can tell you whether your company has formal flex work policies. If it does, tailor your message accordingly.
  • Talk to co-workers. Look for a colleague who has a flexible work arrangement. Talk to her about how she approached her conversation with management and what worked — or, just as important, what didn’t work.
  • Create a proposal. Detail what kind of flexible schedule you want, how you’ll stay connected to colleagues, how you’ll complete your daily tasks and larger projects, and how your plan will help the company.
  • Plan for a trial run. In addition to your proposal, create a plan for a four- to six-week trial period, outlining specifics about what you’ll do and how you will measure success.
  • Set up a meeting with your boss. Be smart about this. Choose a time that will fit his schedule and allow for a detailed discussion of your proposal.
  • Rehearse with a friend. Run through your proposal with someone you trust. Ask her to pepper you with tough questions. Hone your responses.
  • Take a deep breath and make your pitch. Remember that your boss will want to know how your proposal will help her and the company. Stay calm and focused throughout the conversation, even though this may be an emotional issue for you.
  • Share the details. Outline the specifics of how you will complete your tasks, communicate with her and your co-workers and maintain, or even improve, your productivity.
  • Propose your temporary trial. Lay out your plan for this initial effort, emphasizing how and when you will follow up with your boss.
  • Show your gratitude. If your boss agrees to your plan, be sure to offer your sincere thanks. Even if the conversation isn’t successful, exit her office with grace and gratitude. You may want to revisit the issue another time, and you don’t want to leave on a sour note.

By taking these steps, you should greatly magnify your chances of getting successfully to, and through, a conversation with your boss about work flexibility. For more details, check out our webinar on Requesting Telecommuting, Part-Time, and Flexible Arrangements from Your Employer.

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