how to get your boss to say yes to things

If you, like many people, get filled with anxiety when contemplating asking your boss for something you really want (a raise, the ability to telecommute, a better vending machine, etc.), here’s a formula for maximizing your chances of hearing “yes.”

1. Get the timing right. If your company’s just got terrible financial news, or you were warned about your slow production last week, or your boss just separated from her husband, now is not the time to make a special request.

2. Make sure you deserve it. Do you have a track record of accomplishments and increased value to justify your request? It’s pretty easy for a manager to say no to a request from an employee who isn’t wowing anyone; it’s much harder to turn down a request from an employee who she’d be devastated to lose.

3. Build a business case for it. Ask yourself why your employer should find your proposal attractive. For instance, if you’re proposing working from home one day a week, maybe you’ll get more done because you’ll be working during the time you’d otherwise be commuting and will end up putting in more hours than if you were working in the office.

4. Preemptively point out the downsides and offer solutions. Pointing out the downsides yourself — rather than waiting for your manager to do it — can be powerful, because it vastly increases your credibility. Suddenly, you’re not trying to “sell” your boss on something, but instead are collaborating to figure out how to achieve something. Plus, if you don’t foresee the downsides and offer solutions to them, you’re leaving your manager to resolve those downsides — which makes your request much less likely to be granted.

5. Know your own power. If you’re a fantastic employee, you probably have more power than you think you do. If you’re great, your manager doesn’t want to lose you and is probably willing to go out of her way to try to accommodate you, if she can.

6. Realize the answer might be “no” for reasons that have nothing to do with you. Sometimes your request is reasonable and your boss would like to say yes but can’t, because she’s stymied by bureaucracy above her, or has to deal with five more urgent issues first, or knows that if she’ll face a revolt from others if she grants your request. Be sensitive to the realities of your workplace and take a broader view than just how things look from your own desk.

7. If the answer is no, find out what it would take to change that. For instance, if you’re turned down for a raise, ask what you’d need to accomplish in order to earn one.

{ 6 comments… read them below }

  1. Anonymous*

    This is well-timed for me. I’m trying to figure out how to pitch a short leave-of-absence to my supervisors. My unofficial manager and co-workers are supportive, but I have to build the business case to people who don’t know me/my situation well in order to get it approved.

    1. Anonymous*

      Consider asking your unofficial supervisor why she is supportive beside just knowing you and your situation well. Is there any support she is able to offer to you (and/or your supervisors) in terms of alternate working arrangements to help make your leave smoother? That information could help you make your case better.

  2. Anonymous*

    In working retail, my boss is quite lenient in giving us the time off we want, but my colleagues have taken that inch and took the Transcontinental Railroad! Therefore, when I ask for time off, I get the “oh I hope Ishkabibble can make it in on that day.” In making lemonade out of lemons like that, they don’t do it to me when I ask for my earned vacation week, but they do it when I just need a day here and there. I don’t know if the others get the same song and dance.

    It does not matter the timing, my power, etc. The only way I can absolutely get a specific day off with an immediate yes answer is when I tell them it is something I have absolutely have to do and have no power in changing the time and date.

  3. Anonymous*

    I really need to take #5 “know your own power” to heart, but I know #6 and #7 are getting in the way of a promotion for me. I asked my boss what I would need to do to be considered for a promotion, and he replied that he had no idea what the criteria would be for promoting someone or even HOW to promote someone (i.e. the process to go through). So I completely understand that sometimes a “no” has nothing to do with you or your performance.

  4. Anonymous*

    Good tips! In my last management job, I was definitely more flexible with special requests from someone who was a high-performer, committed to the team, and attempted to understand the impact of their request on our group. When someone was doing poor work and cared more about getting their days off than our team accomplishing its goals, it made saying no a lot easier.

  5. Steve G*

    My comments only pertain to requests for time off with shorter notice, emergency leave, or work-from-home/flextime:

    My employers does not babysit employees day to day because it tends to hire very qualified people and probably presumes people at a certain skill level are mature enough to have some self-discipline. The result is that the higher performers tend not to be able to benefit from the 3 benefits mentioned above – we have tighter relationships with business partners and tend to attract higher level/more responsibilities than lower performers. But from an HR perspective we are all on the same level, adults capable of managing our own priorities to benefit the company. Doesn’t really happen in the real world.

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