Brenda Sebastian wants a school garden. The fifth-grade teacher at Soaring Eagles Elementary School in Colorado Springs first mentioned it in passing to her principal, Kelli O’Neil. O’Neil didn’t say no, but she didn’t say yes, either.

Sebastian’s next move was to involve her students in convincing the principal. “When they saw Kelli in the hall, they told her why they wanted the garden and how it would help them in school,” says Sebastian. They also wrote persuasive essays about it.

To address O’Neil’s concerns that the garden would be vandalized, Sebastian proposed applying for grants for a greenhouse. The class did research, interviewing gardening experts via Skype. Sebastian also got estimates on water and electricity costs from the district. Eventually, the students’ enthusiasm brought O’Neil around.

The key, says Sebastian, was not to push too hard, but also not to give up. “Rather than asking Kelli to fund something that she isn’t passionate about, I sought out other ways to pay for the garden and problem-solved ways to address her concerns along the way.”

The Importance of the Ask

“You get what you have in life by asking,” says John Hawkins, a business consultant in Portland, Oregon, and author of Building a Strategic Plan for Your Life and Business. “A lot of people think the answer will immediately be no. The challenge is how to set yourself up for a yes.”

Often teachers don’t think through how to ask for what they want, or they’re too busy to even try. That attitude can result in missed opportunities. And grumbling in the faculty lounge, rather than raising the issue with your boss, won’t get you results.

Instead, get to know your principal and strategize. Find the right time and place. Principals often say they like teachers who are prepared and have anticipated their concerns when they pitch an idea. Others don’t mind brainstorming for a solution. Also, teachers should keep in mind how their proposal fits into the vision of the school, suggests Hawkins. If the bottom line is test scores or enrollment, be prepared to explain how your idea helps. Be smart about your approach and you just may find that your principal is eager to embrace it. Your only regret may be not having asked earlier.

Timing Is Everything

Figure out when your principal will be most receptive. “Most teachers have the tendency to come at the end of the day, when I may be exhausted,” says Trevor Greene, principal of Toppenish High School in Washington state and the 2013 National High School Principal of the Year. “At the beginning of the day I can let the idea germinate and think about [it] during the day.”

Principal Barbara Varanelli of the Arch School, an alternative high school in Greenwich, Connecticut, prefers teacher requests at the beginning or the end of the school year. “When you get to February, you are running out of money,” she says. “Teachers need to be proactive, do their homework, and plan ahead.”

The worst place to corner Sue Szachowicz with a request is in the middle of a noisy cafeteria at lunchtime. Her preference: Send an e-mail and set up a time to talk. Szachowicz, principal of Brockton High School in Massachusetts, is open to new ideas, such as when a teacher recently asked to set up a Big Brothers Big Sisters partnership with a nearby elementary school. She had lots of questions about liability and who would walk with the kids from one school to the other. Teachers need to anticipate such questions, says Szachowicz. “Think like me. What would I worry about?”

Unsure of when to approach your boss? Get to know the secretary—otherwise known as the gatekeeper—and ask for advice, says Hawkins.

Find the Right Avenue

Laurie Barron, principal of Smokey Road Middle School in Newnan, Georgia, and the 2013 National Middle Level Principal of the Year, likes to walk the halls and be approached by teachers informally. “I put myself out there for them. The teachers’ time is more important than mine. It’s more structured,” she says. “I am a colleague whom they can bounce ideas off of.”

Barron also wants teachers to feel comfortable expressing their opinions and engaging in challenging discourse. Early this year, teachers approached Barron with an alternative way to handle bus duty. At Smokey Road, teachers were assigned occasional weeklong rotations of 15 minutes of bus duty after school. They didn’t want to be unavailable to students for such a long stretch, so instead they suggested being scheduled for regular shifts of one day a week.

“The teachers were very thorough. They came with a revised plan, instead of being wishy-washy,” says Jillian Andrew, an eighth-grade math teacher. Barron agreed to the new plan; it was adopted the second week of school. “Laurie is family-oriented, and that’s how she runs our school. It’s easy to ask her for things,” adds Andrew.

Jill Flanders entertains ideas from her staff at recess and lunchtime at Plains Elementary School in Southampton, Massachusetts. “Putting time into building a welcoming culture is important,” says Flanders. “When you establish that, and you find out there aren’t any silly proposals, you get a lot further.”

The younger, tech-savvy teachers at Toppenish High have learned that Principal Greene responds more quickly to a text than to an e-mail or phone call. “If they have an issue that is high need, there is something about texting that makes the person not go on and on,” says Greene. “It’s a shorter message and often easier to solve.” Though he welcomes teacher input, Greene does encourage filtering: “If everything is an emergency, nothing is an emergency.”

Be Prepared

When teachers come with an idea to Mark Terry, principal of Eubanks Intermediate School in Southlake, Texas, and president of the National Association of Elementary School Principals, his advice is simple: “Be prepared to share how it will benefit the kids.” He also likes teachers to think through the consequences of
the proposal beyond their classroom.

Kim Pelt, a sixth-grade language arts teacher at Eubanks, either sends an e-mail or drops by Terry’s office when she has an idea. She says that with Terry, there never seems to be a bad time. Once, she suggested letting students use their cell phones to respond to questions in class. She came prepared for his concerns about potential misuse and how to accommodate kids who didn’t have a phone. Terry signed off on it, and Pelt says her students are so excited to use their phones in class that there hasn’t been a single incident of one being used inappropriately in two years.

When Jillian Andrew put together a request for technology and materials for her remedial math class, she had all her paperwork in order. She submitted the forms to the Title 1 coordinator and to Principal Barron, who approved them almost immediately. “It was teacher Christmas,” with new ELMO document cameras and manipulatives, says Andrew.

Believe in Yourself

Nichola Blink, an opera singer turned music teacher, wanted to grow her part-time position at Toppenish High into a full-time gig. Her approach was “Build it first, ask second.” She told the principal (at that time, not Greene) that if given the chance, she’d show results. Blink started with 12 students in the choir. She had 85 by the end of the first year and 200 by the end of the second.

As the program grew, Blink asked for additional equipment and support, using a three-tiered approach. She placed essentials, such as tuning the piano, in the top tier. Second-tier items would make the program as successful as others in the area, and the third tier would make it world class. “I compared my requests to other schools in the area, so they’d know I wasn’t pie in the sky,” says Blink, who has worked full-time at the school for seven years. Finally, she explained how her requests would make her students more successful and competitive. “I said, ‘Here is my dream, my vision.’ I was very forthright.” It worked.