Do you have a story like this? Dave wants to leave work early on Thursdays to attend his daughter’s soccer practice. He’s been thinking about this for weeks. Every time he comes home on Thursday night and hears his daughter excitedly explaining all the things he missed at soccer. He feels guilty, and his desire to be at soccer games grows stronger. Finally one Thursday, Dave ambushes his manager, Susie, in the hallway: “I need Thursday afternoons off,” he commands, “or I’m quitting,” he adds silently. He feels a moment of fatherly pride – there, he did it, he made his special work arrangement request. Susie, flustered and instinctively defensive, responds “Dave, we work Monday to Friday around here, you know I can’t have everyone just taking off when they feel the urge.“
Welcome to the World of I-deals
If you’d love to ask your manager/employer for a special work arrangement, what’s the best way to approach it? In organizational science, a special work arrangement is called an “idiosyncratic deal,” or “i-deal,” because it’s made to fit a single person’s unique (idiosyncratic) goals, needs, and preferred work style. Research on idiosyncratic deals provides insights into strategies that succeed and strategies that fail.
Companion Post: Are you a manager facing decisions about special work arrangement requests? Check out our guide to idiosyncratic deals for managers.
In the best case, a good special work arrangement will provide mutual benefit – leaving you feeling more appreciative and more committed to your organization than ever, and adding value to the organization as a result.  
In the worst case, your request for a special work arrangement will be rejected, leaving you stuck with your present situation. Your failed request may even come across as a request for unfair special treatment that management resents. Or your request could get accepted but it could garner you so much resentment from coworkers that your reputation and future opportunities within the company are threatened. 
Luckily, research suggests some great tips for a successful special work arrangement request…
Step 1: Prework
First, people who do a little homework before pitching a request for a special work arrangement are more likely to get their deal accepted .
Your goal: Predict the concerns that your boss, coworkers, and/or customers are going to have about your special request. Think through creative solutions that could alleviate those concerns.
Figure out your fallback plan.
If everything falls apart, and your boss doesn’t support your special work arrangement request, what will you do? Research in organizational science suggests that people who enter negotiations with a fallback plan already in mind are more effective in achieving a solution. Having a fallback makes it easier to be calm and reasonable, rather than defensive and desperate. 
Example: You want to shift your full-time work schedule earlier in the day so you can attend classes in the evening. Your fallback plan might be going to work part-time in another company.
Talk to your coworkers.
Run your special work arrangement request by a couple of coworkers/friends before you pitch it to your manager. Be thoughtful and tentative so this step doesn’t backfire. Focus on several purposes…
- Your coworkers might know about similar deals that have been made with other people in the organization. (Bonus tip: more senior coworkers might be especially helpful here.) .
- You’re getting practice. Just discussing your desired deal with coworkers gives you practice articulating it. You can hear how it sounds out loud and watch their reactions.
- You’re warming up your coworkers to the idea of having this special work arrangement in place. If you successfully negotiate your deal, then your coworkers’ attitudes can make or break its long-term prospects. It’s important for your coworkers to be happy that you have this arrangement.
- You’re acquiring allies. If, by the time you start negotiating your special work arrangement with your boss, you already have tacit support from several coworkers, you’ll have helpful responses ready. You’ll be able to say “I’ve thought about that, and ran it by [list coworkers], and they were supportive.” Your preparation lets your manager relax a little bit if it’s clear that you share a concern about backlash from coworkers and that it may be partly addressed already.
Maybe talk to your clients too
If having a close relationship with a few clients is part of your job, you may want to run your idea past a few of your favorite clients to make sure they’re comfortable with it (e.g., “Do you expect to need me after 3pm? OK if I give you my cell in case you ever do?”). 
Again, be thoughtful and tentative with your early outreach. Your goal is not to make your manager feel cornered by a request that’s been inappropriately “decided” by you and your supporters. Rather, you’re testing your own brilliant plan to make sure it seems acceptable and beneficial (or at least not harmful) to others as well. This is a time to listen and work to clarify, refine, and improve your request so that it might be accepted and broadly supported for as long as you’d like by everyone who may be impacted.
Step 2: Pitch Your Special Work Arrangement Request
With your prework done, your fallback plan defined, and your coworkers consulted, you’re ready to approach your manager. Here’s the approach research supports…
- Don’t blindside your boss. Dave’s hallway ambush with Susie is an approach that gets in the way of success. Sit down with your manager – if you would typically schedule time to talk, do so for this request as well. Ask for consideration of your request rather than an immediate response. Offer to refine your proposal together or in response to your manager’s feedback.
- Communicate your WHY. Open with your purpose and values. If you don’t explain why you want this special work arrangement, you’re forcing your manager to fill-in the blanks with assumptions. Those assumptions may not be accurate or flattering, and can put your manager in the wrong mindset. You want to go part-time because you want to continue your education/professional development, not because you’re unhappy with the company or uncommitted to your work.
- Your goal isn’t to win. It’s to discover a creative solution that satisfies as many of your shared and mutual interests as possible.
- Use a cooperative approach. You care about preserving your relationship with your boss and the company over the long term, not just getting this special work arrangement. Ultimately, regardless of the response, your request and discussion could really improve your work relationships. And even if this special work arrangement request is denied, perhaps you’ll craft and request a different one in the future. Have a cordial conversation that makes that possible.
- Keep your fallback plan to yourself. Don’t use it as a threat (e.g., “I need Thursdays off, and if you have a problem with that I’m quitting.”) Your fallback plan is an option you have, not a manipulative tactic to strong-arm your manager, and if you mention it, you’ll put your manager on the defensive. Draw strength from your fallback, but only bring it up if negotiations are falling apart, and mention it as “something else I’ve considered.” Then be ready to hear “no” to your special work arrangement request and to move to your fallback plan.
If your manager voices concerns about your proposed special work arrangement, chances are that s/he doesn’t blindly hate the whole thing. It’s likely that specific parts of the deal raise specific concerns. Your mission is to ask diagnostic questions to find out which aspects of the deal bother your manager and why. Then be open to modifying your request.
Step 3: Maintain the Deal
Congrats, you successfully negotiated your special work arrangement! So you’re done, right? Just start living your new and improved life? Not so fast. People who successfully negotiate special work arrangements are at risk of being resented by coworkers and managers, and even being passed over for promotions .
Your mission, now that the deal is accepted, is to forever strive to prevent your deal from negatively impacting your managers and coworkers . The other people you work with shouldn’t have to put in more effort in their own lives because you deserved this special work arrangement. Research backs a generous attitude here, to make your special work arrangement a pleasant and sustainable thing for everybody.
Here are some tips…
- Talk to your coworkers about the arrangement. If you don’t give them a way to interpret it, they’ll make their own interpretations when they hear about your deal second-hand. Circle back and thank anyone you consulted in advance. And don’t skip anyone you haven’t shared with yet.
- Make it easy for coworkers to be un-jealous. Evenly frame the deal in terms of flexibility and sacrifice. “They’re letting me take Thursday afternoons off!” is much easier to resent than “I’ll be able to go to most of my daughter’s soccer games, which is awesome, but the evening make-up work is going to be rough. Don’t worry – I’m working it out so that this won’t be a burden on our team.” Also, choose your language carefully to avoid misunderstanding. Saying “I’m getting Thursday afternoons off,” sounds like extra paid time off. Saying “I’m out of the office Thursday afternoons and checking messages before closing time” shows greater respect for the work time you are adjusting.
- Keep everybody reminded of your WHY. When people ask “Why isn’t Dave in the office on Thursdays again?” you don’t want the answer to be “I dunno. I wish I didn’t have to be here on Thursdays. Dave is a lucky slacker.” You want the answer to be “Because he arranged to attend his daughter’s soccer games this season – actually he already sent me the draft report last night. Dave is such a great colleague and dad.” or “Because she took a 20% pay cut to pursue her MBA on Fridays. Jane is so driven.”
Need some inspiration to take initiative to design your life?
What strategies have you seen or used to accomplish special work arrangements to reach your goals?
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