How To Get Your Boss To Say Yes

You’re passionate about the work you do and the company you work for. Whether you’re an entrepreneur or an intrapreneur, you’re all about making your organization a more innovative and creative place. That means you’re looking to instill a mindset and implement solutions that enable you to be more creative in your problem-solving. But to do that, you have to get your boss and the rest of your team on board.

What about the one-off little wins? What about the projects you want to dig into and the classes you want to take? With competing priorities, ever-changing deliverables, and yesterday due dates, it can be a real challenge to communicate the value of those items to your boss and get their buy-in so you can move forward.

So what’s the best way to get your boss on board? We’ve got 4 strategies for getting to the “yes:”

1. Show, Don’t Tell

Your boss gets a ton of requests and hears a lot of pitches. How can they decide what projects and ideas are worthwhile? What makes a pitch convincing? One strategy is to present the facts in a concrete and creative way to help your boss come to the same conclusions you have. In other words, skip the speech!

Instead of presenting a report or a list of facts and figures, focus on constructing a compelling narrative. Use your storytelling skills to create an experience of the problems or ideas you’re trying to address—that’s way more convincing than bullet points in a slide show. You can bring in videos, customer surveys, prototypes, or mockups to build an experience and make it easy for your boss to see things from the point of view of the user.

At our recent Designing Culture panel, Geoffrey Schwartz from Frog Design gave the example of an employee at a client organization that sat in and filmed the user interviews. He then went to his boss and instead of just telling her the problem that surfaced from the interviews, he played her the tapes. She was able to see the problem for herself. So when it came time to stating the problem, she was already completely bought in. That’s a great way to bring the problem to life. So don’t just tell your boss what you’re trying to do—show it!


2. Make It Measurable—Back It up With Data

You may have heard that diamonds are a girl’s best friend, but diamonds got nothing on data. Anytime you can bring hard numbers and proof with your proposals, you’re more likely to get buy-in.

Do your homework ahead of time and come to your boss armed with the data that you’ve gathered on the problem and your proposed solution. Show how the project fits into the budget and how much time you expect it to take. Offer case studies that show how your proposal has worked in other organizations. Pull up consumer reports and survey data to back up your assertions. Bring the numbers that show how your idea fits into the bottom and top lines (and, ideally, improves it).

And remember, your data should be just like the rest of your idea—shown, not told. Present it in a way that is clear and easy to absorb at a glance.


3. Present the Problem with a Solution

Not only is it more impactful to show an idea rather than just tell someone about it, you should also aim to frame the problem in context with a solution. You’ve put a lot of work into identifying and understanding the problem your solution addresses, but your boss may not have as much insight. Even after you get them bought into the problem, the solution you envision may not be self-evident to them.

It’s a lot easier to get your boss on board with a complete, coherent plan rather than with a problem or solution in isolation. This is also a great way to show your initiative and commitment to solving the problem, which instills a sense of confidence in the work you’ve done and in the solution you’re presenting.

And remember, just like with your problem, you’re going to want to show your solution. For example, IDEO used cardboard to simulate ideas for new human-centered layouts for Planned Parenthood’s clinic space. You could also sketch a quick mockup of proposed changes to your app’s UI or to the design of your product. That way, you’re showing how your solution addresses the problem in a concrete and tangible way.


4. Put It in Context—Map It Back to Your Organization’s Vision

As an organization, you’re all pushing toward a common vision. That vision has two parts: the vision itself and the how you’re planning on achieving it. You can use that vision both to shape your proposal and to get your boss bought in.

In your presentation, clearly map both the problem and solution along the path toward your organization’s vision. Show how the problem is one that your organization is committed to solving and how the solution fits into the org’s long-term strategy. By offering actual strategies for achieving (or at least working toward) that vision, you’re showing your boss that you care about the vision and that your proposal is in line with it.

Say your organization’s vision is to become the largest provider of widgets and you’ve come up with an optimized UI that you believe will drive more conversions—pull up the data and set the context of how those changes will help your organization boost its widget market share. Or, say your organization’s vision is all about providing affordable childcare options for working moms and you want to start offering an after school program. Bring interviews with moms and kids to show that the need for after school care exists and how your proposal is designed to fit that need.


Getting to the Yes

To get your boss to say ‘yes’—whether you want to change to your business model, tweak your software, or or take a design thinking class – the key is to effectively (and efficiently) demonstrate the value of your proposal. That takes more than a slide show or a memo—you need to make an impact which requires empathy around what’s important to them. To get your boss bought in, you need to build a compelling narrative around the problem you found and the solution you’re proposing. By showing your ideas, bringing the data to back it up, presenting the problem and the solution together and framing your idea into your org’s vision, you’re sharing a story with your boss, not just a list of facts and figures. That makes it super easy for your boss to say yes—and probably to applaud your initiative! You believe in your proposal and these tactics can help you get your boss to believe in them, too.



The Design Gym
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