How to Get Your Boss to Say Yes

As an employee, chances are you’re going to want something from your boss eventually, and you’re going to have to ask for permission or approval. You may need new tools and materials like a new computer or desk, you want to attend a conference, work from home or have the option to telecommute, you need approval for a new program proposal, etc.

Innovating in the workplace isn’t always easy. Even if you have amazing ideas for new ways to do things, your boss may be reticent to change things and you may get “No” because things have always been done this way, we need to be realistic, maybe in the future, and so on.

But it’s not always about what you’re asking for, rather how you ask for it. The concept of “managing up” to your boss is problematic (no manager likes to be managed). Instead, think about other ways to influence your boss.

Here are some tips to lay the groundwork for getting a “Yes” out of your boss:

1. Timing is everything

If there’s a major merger going on, dismal second quarter financial results or a company-wide cost cutting initiative underway – now is probably not the best time to lodge your special request that will take additional funding. (However, if you have an idea that will save more money – like giving you Fridays off – this could be a great time to bring it up.) Make sure you take into consideration the whole picture when you’re thinking about bringing up your idea. Timing could be the difference between getting a No or getting a Yes.

2. Do your homework 

Do research on your pitch. If you have metrics, case studies, and examples of competitors, reviews, or success stories it will be a much more compelling proposal and much easier to get a Yes.

3. Channel “Shark Tank” to get to Yes 

If you’ve ever watched ABC’s show Shark Tank – where entrepreneurs pitch their ideas to investors – you can learn from the pitches that get a YES from the investors.  Be clear, concise, and well-organized and researched in your proposal, idea, or request. If you haven’t done your homework and your idea is full of holes, you are making it easy for your idea to be rejected.

4. Start with the conclusion/state what you want/your recommendation

Don’t keep your boss guessing where you’re going with this, or he’ll be distracted through your whole pitch about why he should agree to it. State your objective upfront, so the rest of the time he can be listening to the reasons he should say Yes to it.

5. View the idea from the corner office perspective

Most bosses need to do two things in their job: increase profits and grow the company. So if you can build your pitch around a way to save or make more money and/or growing the organization, a Yes is going to be more likely. Additionally, keep in mind that most bosses have a boss that they need to look good to. If you can make them look good to their boss in the process, build that into your strategy as well and (subtly) include that as a subtext of your pitch.

In Part 2, we’ll cover the next steps to effectively drive your pitch home and get your boss to say YES!