Getting to YES: Upping Your Presentation Skills to Get the Greenlight from Your Boss

“You never get a second chance to make a good first impression in your presentation.”

Your Presentation

That old adage holds true for pretty much every interpersonal interaction you can imagine. First date? Yes. First meeting with your significant other’s parents? Yup. First time you present a new idea or proposal at work? Definitely.

In each of these situations, your goal is to successfully persuade someone of something: that you’re someone they might want to get to know better, that you’re an upstanding and kind individual, or that you’re an intelligent, responsible, and organized go-getter.

In the workplace, your ability to deliver a great presentation can have a huge impact on getting to yes for a proposal, your career or really almost anything that have to get done (as most of us rely on input from others to achieve our objectives). To maximize your chances of success, you need to pay careful attention to four critical areas when you present (whether formally or informally): audience, content, delivery, and confidence.



“Each audience is different.”

Your audience is the most important aspect of your presentation. As you begin to craft your proposal, you first need to get a solid understanding of which decision makers (or influencers) will be involved in this process. Never start a pitch until you know who’s in the room; otherwise, you may end up putting together a pitch that totally falls flat (and wastes everyone’s time—including yours).

Your PresentationTo analyze your audience, start by answering these questions:

  • What are their positions relative to yours (e.g., managers, peers, direct reports)?
  • Are they technical or managerial in function or knowledge?
  • What is their level of experience?
  • What do they already know about the subject?
  • What interests them?
  • How will what you are going to say affect them?
  • What is the desired end result? (As a result of your presentation, what should they do, understand, or believe?)

Once you have an understanding of who your audience is and what their interests are, you can build the content and delivery of your presentation to target them.

For example, be sure you’re communicating at the appropriate level for your audience: if you pitch too low, they’ll be bored and stop listening; if you pitch too high, they’ll be confused and stop listening. (And if you’re delivering this presentation in a virtual environment in which people are already inclined to multitask, you’ll need to work extra hard to keep them focused.) Finding the right balance to maintain interest and engagement depends on how well you understand your audience.

To sell your proposal successfully, you must understand your leaders and their goals. Target their priorities, mitigate their pain points, and be sure you convey—in clear and specific terms—how your proposal helps them achieve their own objectives.


Your Presentation Content

Ideas are easy. It’s the execution of ideas that really separates the sheep from the goats.
—Sue Grafton

Your Presentation

Once you’ve analyzed your audience, it’s time to think about how to translate your message into a great presentation that makes your audience think differently or act in a certain way (for example, approve what you’re pitching). In order to most effectively deliver your message, ask yourself the following questions as you craft the content of your presentation:

  • Why is this issue important to the organization?
  • How does it help meet the organization’s mission, vision or goals?
  • Why should the decision makers care about it?
  • How does this fit into or support our values?
  • Why does this issue need to be addressed now?
  • What is your call to action?
  • What data support your recommendation?
  • What questions might your audience ask—and how will you respond to them?

Remember, your content is not just the message you want to convey. It’s really about conveying your message in the context that your decision makers can understand, relate to, and care about.



There are certain things in which mediocrity is not to be endured, such as poetry, music, painting, public speaking.
—Jean de la Bruyère

Most highly effective presentations follow some version of this four-step communication structure:

  1. Lead with a headline that clearly and briefly states the problem and your recommendation. Many of us take too long to make our major points because we’re scared that if we don’t provide lots of context first, our ideas will get rejected or the executive will assume we haven’t considered all the variables. That’s a major mistake! The best way to communicate with senior executives is to lead with the important information and then provide the details.
  2. Share your thought process and your data. This is how you demonstrate your credibility and the quality of your thinking. This is the “why you should trust me and follow my recommendation” part of your presentation.
  3. Ask for input and discuss it. Inevitably your boss or senior leader will want to add value to your proposal (that is part of their job, after all). Answer their questions as clearly as you can, and if there’s one you can’t answer, don’t fake a response, because they’ll see right through it. Instead, reply with “That’s a really good point—I’ll have to think on that some more. Do you have a suggestion for how to address it?” Your role is to use their advice to make your work better.Demonstrating your openness with “I’d love to get your perspective and advice on how to make this even better” also shows respect by asking for advice. The more your senior leaders feel invested in an idea, the more they will support (and sell) it, so don’t underestimate the importance of asking for (and listening to) their feedback.
  4. Present a summary and call to action. This ensures that both you and the senior leader are on the same page and helps propel forward motion for your project.

As far as timing goes, step 1 should be very brief (10 percent of your presentation)—as the kickoff for your proposal, its function is to grab attention and set the stage for what comes next. Steps 2 and 3 are the “meat” of your proposal and therefore should take up the bulk of your time (65 percent of the presentation). As the wrap-up, step 4 is a summary and call to action and should take up the remaining 25 percent of your time.

Your Presentation Delivery Variation #1: The Elevator Pitch

You won’t always be able to deliver a scheduled, extensive, detailed presentation. Sometimes your only chance to sell your idea to a decision maker is during a brief (often unscheduled) interaction: the “elevator pitch.” Getting to yes can be challenging in such a short period of time, so I typically use an elevator pitch to hook my listener’s attention so that they want to schedule a follow-up meeting to get into the details.

Whether your “elevator” is literal (you actually share an elevator ride with your boss) or metaphorical (you and your boss are walking out of the office to the parking lot at the same time, for example, or you run into them in the coffee room), following these best practices will help you deliver a killer presentation in those circumstances:

  • Be concise. Your pitch should take no longer than 60 seconds.
  • Be clear. Avoid fancy words and use language that everyone understands, otherwise your listener will get lost—and you’ll squander your opportunity to hook them.
  • Be powerful. Grab their attention with words that are powerful and strong.
  • Be visual. Make your message memorable by using words that create a visual image in your listener’s mind.
  • Tell a story. A short narrative about someone with a problem provides an engaging lead-in to your proposed solution.
  • Target your audience. If you have target audiences that are vastly different, you might want to have a unique pitch for each of them. Be sure to explain why your audience should care.
  • Focus on the goal. A terrific elevator pitch is designed with a specific outcome in mind. What is your desired outcome?

Your Presentation Delivery Variation #2: Virtual Meetings

Even though many workers are starting to return to their offices, virtual meetings are likely to be a mainstay of the corporate world for the foreseeable future. These kinds of meetings have their own best practices to consider when you are presenting an important proposal to your boss.

  • Every presentation coach will tell you that direct eye contact is vital for reinforcing your point. In a video conference, this means looking into the video camera—not at your colleagues’ smiling faces. Redirecting your gaze in a video meeting may feel awkward at first, but it’s a skill well worth developing.
  • When delivering a presentation, it’s always advisable to use a louder-than-usual voice because in addition to being more audible, strong voices convey authority, credibility, and confidence. In a virtual meeting, remember to speak not only as loudly as if you’re in a real conference room but also as clearly as you can (which may include slowing down a bit), because it can be extra difficult to hold someone’s attention and communicate with them when you aren’t in the same room with them.
  • Don’t appear far away. Proximity plays a big part in how your audience perceives you as a communicator: the farther away or more obscured you appear, the less engaging you will be. In a video conference, your head and the top of your shoulders should dominate the screen.
  • Be mindful of your background. A cluttered room will make you seem disorganized and pull attention from you and your message.
  • Don’t become your own distraction. Keep your microphone muted except when you speak, so it doesn’t pick up unwanted background noises. (This is especially critical if you’re at home, where pets or other family members might unintentionally end up participating in your meeting.) Taking occasional sips from a beverage while on screen is fine, but turn off your camera while eating.



Believe in yourself! Have faith in your abilities! Without a humble but reasonable confidence in your own powers you cannot be successful or happy.
—Norman Vincent Peale

If you want your boss to sign off on your proposal, you need to present it with confidence. After all, if your boss doesn’t think you believe the project will succeed, why would they want to support it? The best way to increase your confidence is to be prepared:

  • Rehearse your presentation until you have the delivery down cold.
  • Anticipate (and be prepared to address) any questions or objections that come up.
  • Practice breathing and relaxation exercises to help you calm and focus your mind.
  • Visualize the presentation going well.

When it’s time to make your pitch, use eye contact to connect with the audience. Never apologize or make excuses, and let your careful preparation give you the foundation you need to proceed confidently.


Final Thoughts

Having a good idea is one thing. Getting to yes to act on that good idea is something else entirely. As long as there are senior leaders above you who are calling the shots, you’ll need to understand how to sell your proposal effectively. With solid preparation and good communication skills, though, you can get the “yes” you need to advance your project and help achieve success for your organization, your boss, your team, and yourself.

Do you have any tips for other strategies that are particularly effective when presenting proposals to decision makers? Share them here in the comments!

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