5 Questions Before Pitching Your Boss

Jared Bloom
 min read
5 Questions Before Pitching Your Boss5 Questions Before Pitching Your Boss
Table of Contents
You’ve developed the plan. You’ve scheduled the meeting. So now what?

Before you build your first slide, ask yourself these five questions to give yourself the best chance at convincing your boss and turning her into an advocate for your bright, shiny idea:

1. "How much time will I have?"

There’s a big difference between a 1-hour meeting and a 15-minute chat. Make sure you know exactly how much time your boss is likely to give you so that you can prepare your presentation accordingly.

If you have ample time to present your idea, you might want to provide context before diving into your big idea. For example, there might be relevant trends or research you want to share that make your idea more compelling. But if you only have a few minutes to pitch and discuss your proposal, the last thing you want to do is get cut off before you get to explain your idea. In these cases, consider building just a few slides to summarize the idea and then opening up the conversation to questions.

2. “How does my boss prefer to communicate?”

If you’ve been in enough meetings with your boss, you probably have a good sense of how she likes to evaluate ideas. She might be the type to sit back and listen before sharing her opinion, or maybe she immediately starts peppering you with questions.

As with any presentation, your pitch should be tailored to your audience’s preferred style. If your boss is the type to quietly consider a presentation, then your goal should be to anticipate her questions and answer them proactively. On the other hand, if she’s quick to interrupt, then think of your presentation less as a narrative and more as an appendix. Your goal should always be to control the conversation, but always be ready to flip to slides that answer her questions and then transition back to your pitch.

3. “What is her biggest objection likely to be?”

You may be the one who is going to execute on your idea, but chances are it’s your boss who’s going to have to answer for the consequences. Try to put yourself in her shoes to identify the #1 reason why she might not want to see your proposal go forward.

She might have questions about the ROI of your idea, the amount of time and effort it might take away from other efforts, or the public fallout if it fails. Whatever the case, don’t avoid these issues and hope they don’t come up. Instead, address the biggest objections head on—early in your presentation—to make sure that lingering doubt doesn’t persist all the way through your pitch.

4. “What specifically am I asking for?”

This sounds obvious, but it’s something that presenters often forget. We get so caught up in selling our idea that we forget to be clear about what we want our audience to do about it. After all, a good idea is only worthwhile if it leads to action.

When presenting to your boss, you’re probably asking for one of three things: budget, time, or permission. If it’s one of the first two, make sure to be specific about how much time or money you need to execute on your idea. And if it’s permission, give her direction on how to grant that permission. (For example, does she need to send an email to the Director of HR or attend another meeting? If so, offer to draft the email for her or add the meeting to her calendar.)

5. “Will she need to share my slides with others?”

There are some cases where you can get approval for an idea during the meeting. But other times the meeting is just the beginning of a process. If getting approval isn’t as easy as a yes or no from your boss, chances are she’ll need to present your idea—and your slides—to other key members of your organization. And this can have a significant impact on the types of slides you create.

If your presentation is for your boss’s eyes only, then you might want to build more visual slides that engage your boss’s emotions. This allows her to focus on you and your idea, not the words on your slides, but it also means that it requires a presenter. However, if she needs to run your idea up the flagpole, then you’ll want your slides (or a version of your slides) to stand on their own. This may mean using more descriptive headlines—e.g. verb-driven sentences rather than one or two-word headers—and additional text to support your visuals.

A great pitch to your boss does more than just get your idea approved. It also signals that you are someone with clear vision and an ability to communicate that vision with passion and purpose. So it’s important to treat every presentation



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Jared Bloom

Jared Bloom