Pitching an idea can be scary. Pitching an idea to your boss can be really scary. But it doesn’t have to be. Having worked in marketing and communications for more than 18 years, here are my top tips to help you sell it up the ladder and ensure leadership buy-in when it matters most.
You can’t sell what you don’t believe.
Have you ever tried to convince someone of something that you know in your gut you don’t even believe? Yeah, it sucks. And, chances are, the person you’re trying to convince can feel your uncertainty or lack of conviction.
Feeling truly convicted about a direction requires head, heart and gut alignment. That’s no small ask! You have to do your research, know what you’re talking about and be prepared to answer questions.
Illustrate that this isn’t a spontaneous thing. Show them you have explored many directions and decided this was the right one. You have to be willing to explain why you’re personally motivated and passionate about doing the work. After all, it’s hard to argue with someone willing to put in the effort.
Sometimes, it’s a conversation, not a presentation.
While it’s nerve-wracking to pitch something to a boss—and many understandably approach those moments like they’re on trial in a courtroom—the truth is that most leaders don’t want to be lectured to. They want you to give context, bring them into a conversation and ask their opinion.
Around the office, I like to practice what we call “facilitative leadership.” It’s pretty simple, really: Frame up a conversation, seek input and aggregate it at the moment.
And if your pitch isn’t going the way you planned, be willing to pivot! Listen for cues, watch body language and even ask whether the ideas you’re sharing are hitting the mark or not. It may seem counter-intuitive, but open dialogue and genuine exploration lead to great ideas.
While it’s certainly important to be passionate, never be so tied up in an idea that you’re unwilling to integrate others’ thoughts or feedback. You can be committed to your mission and still have an ear for improvement.
Being open to feedback shows strength and confidence, generating leadership trust in you to execute a big plan.
Selling is storytelling; it has to be personal and authentic.
Some of the best presentations are based on key takeaways. If you can only make your audience remember three things—or even one—what do you want them to walk away with? Start there. End there.
Remember that even the most sensible leaders are also driven by emotions. Connect to them where they are, and present your ideas in the context of problems you know your team faces. It’s not just a sell; it’s a solution.
Finally, when sharing your “story,” remember to keep it tight. Walk folks down the path, and bring it to a close. Leaders want headlines, so get to the point.
Don’t be afraid to educate—even leaders need context.
This is huge: Ground the room with context. Most leaders spend their days running around like crazy trying to get everything accomplished; they often don’t have all the background info before coming into a meeting. Don’t be scared to tell them point-blank.
First, acknowledge the need to define baseline concepts to ensure the room is on the same page about what’s being asked. Explain that data should drive decisions and make space for questions about what the data indicates. Finally, keep it simple: Artifacts and eye charts are great tools if they offer a snapshot of the data but don’t overwhelm your audience. Give them just enough to offer context and offer opportunities to see more if they’re interested.
You’re not talking down to the CEO when you explain your project’s context, the need and the “how.” You’re giving them the information they need to make an informed decision.
Ahead of the conversation, decide if you need your leader to be a decision maker, a consensus builder, an influencer, etc. Know this ahead of time, and tell them what you need. They’ll appreciate this.
Then give them answers to these questions.
• Why are we here?
• What do we hope to achieve?
• What role do I need to play?
Any good leader worth their salt isn’t scared to be educated by one of their teammates.
When it’s finally time to ask, bring it back to values.
Bring everything back to brand values—they’re really hard to debate, especially as a leader whose goal is to drive them forward.
Explain, with confidence, why this internal restructuring supports your team’s value of collaboration. Tell them how hiring an in-house conflict resolution specialist is a critical step in bringing empowerment to every level at the company. Use your on-the-ground experience to help your CEO understand why your team needs those extra resources to accomplish their client satisfaction goals.
Then, be sure to explain what will happen if the team doesn’t do what you’re asking. Sometimes the fear factor around things not improving or worsening can be the most compelling reason for change.
And when it’s time, action-plan with closure.
Confidently say, “Here’s where we’re going. What thoughts do you have?” When budget concerns come up, don’t shy away. Offer a historical context or a ballpark estimate of what it’s going to cost. It’s usually a one-shot kind of thing, and leaders won’t backtrack. Give them an idea of the cost, get them committed and work out the details next.
Show ’em what you know.
Selling it up the ladder isn’t easy. It can be intimidating, and it’s often those nerves that undermine a good pitch. Go in with confidence in yourself and your proposal, open up a meaningful dialogue led by data and driven by company values and show your boss what you know.
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