Category: Life Lessons

Whether you’re pitching your new business idea to the CEO or pitching buying a new car to your spouse, crafting a winning argument, once you’ve passed the feasibility hurdle, is highly dependent on the tactics and strategies you use to sway the decision-maker. We’ve all been on both sides of the equation—delivering and receiving successful and unsuccessful pitches. I’d be willing to bet that when you’ve been the person on the receiving end of an awful pitch, you know exactly why the pitch failed.

Awful pitches are horrible for many different reasons: sometimes the person is unprepared, sometimes they’re condescending, and sometimes the person believes that all it takes to win the day is including all the relevant information in the pitch and letting the collective weight of the data convince the person to decide in his or her favor.

However, I’d also be willing to bet that when you’re on the delivery end of an awful or unsuccessful pitch, you rarely know the exact reason why the pitch didn’t sway or persuade. And the truth is, we’re rarely given the opportunity to query the decision maker once we’ve pitched and failed to zero in on why exactly they weren’t convinced to decide in our favor. Often this leads people to go down a rabbit hole of wrong explanations, wondering if they weren’t specific enough or left out a critical piece of information when in truth, the answer is far more clear-cut. Setting aside being unprepared or condescending as reasons for a pitch not succeeding, most pitches fail simply because the person making the pitch shares everything they know about the matter at hand rather than everything the decision maker needs to know to make their decision.

It’s no wonder the pitch was an epic failure—it was crafted from the perspective of the pitcher and not from the vantage point of the decision-maker. An exceptionally subtle yet influential distinction that spells the difference between winning over a decision-maker and a failing pitch. Avoiding your next disastrous pitch starts with making some smart and meaningful changes in the process that you use to craft your pitch that make a meaningful difference in how the pitch will be perceived by the person you need to make the decision.

These simple yet powerful tweaks will help pare down your pitch, focus it on the decision maker, and therefore substantially increase your ability to successfully win over any decision maker you face.

Be Sure That You’re Presenting To The Ultimate Decision Maker

It might seem a bit simplistic to say this, but be sure that when you’re pitching someone on an idea that you’ve targeted the presentation to the decision maker with the authority to ultimately make the choice. This is critical, especially when pitching to a group where multiple players may hear the pitch but not have the authority to make the decision or be the person you want to work with on a deal. Failing to target the pitch to your audience, even if it is only to one person in the room, can sometimes alienate the true decision-maker you want to sway. Persuasion, no matter how effectively done, directed to a person who has no authority to make the decision is never going to yield the desired effect.

Know Your Decision Maker

Learn as much as you possibly can in advance about the person making the decision. The most important information to understand concerns their patterns around what motivates them to make decisions and draw conclusions. How are they motivated to do something or not do something? Is it to avoid problems or achieve goals? Are they convinced to take action when they know within themselves that something is right? Or do they use facts and figures to help them decide? And lastly, are they proactive or reactive: do they like to initiate change or wait until a situation is right to act?

The best place to get answers to these questions is directly from this person. Observe how this person has made decisions in the past, note how they present information, listen to their words and notice their body language in certain situations. You could even sit in when someone else is pitching them and watch what happens, what they ask, and what works and what doesn’t. Look for little peculiarities that you might want to take advantage of: think “royalty deal” and Shark Tank’s Mr. Wonderful, Kevin O’Leary.

Know The Question And Know The Recommended Action You Want Them To Take

Have you ever tried making a decision when you didn’t really have a clear idea about what you were really being asked to decide and/or the person doing the asking didn’t know a hill of beans about what they were asking you for? You can’t expect someone to give you a decision when they can’t clearly identify the question they’re being asked to decide or the action they’re being asked to take. Your first and foremost responsibility is to know the question that needs to be answered and to define what action you think would best works to solve/answer it. Without this level of clarity, you can’t ever hope to make a successful pitch. At this stage, you’re really working to figure out your best guesstimate of what would work best and why the decision-maker would want to take the action you’re proposing. Write both your question and answer down, keep clarifying it to make sure that there is no ambiguity and that your recommended action is the only action that will bring about the desired resolution to the question, and perhaps most importantly, that you can state why convincingly.

Carefully Lay Out And Select Your Best Points: Concentrate on Your Ideas

Your very next step is to begin laying out the facts, information, and arguments that are central to your pitch and form the basis for your core action/recommendation. Laying out and structuring the information and arguments in a logical manner will help you spot gaps in your knowledge of the facts, understand where challenges to your recommendation might come from, and help you counter potential objections with real counterpoints. Pay careful attention as you go through this process to keep the information tight and concise, making sure only to include only the most compelling and salient points in your outline so that your ideas are concentrated and therefore have the most influence and impact on the decision maker. Select your best and strongest reasons why this action should take place—preferably no more than 3 or 4—and develop them fully. This is not to say that each of the 3 or 4 cannot have a few smaller points within them. However, loading up a pitch with everything but the kitchen sink and taking a scattershot approach is ineffective. It gives the impression that you don’t come from a position of strength and that you don’t have strong points that can stand on your own. Your criteria for including a point should be:

• That it is essential to the core of your pitch
• It is scrupulously accurate
• It is presented from the vantage point of the decision maker

If it doesn’t fit these criteria, it isn’t going to help and will most likely become a straw man that can sidetrack your pitch.

Create A Story

Now that you’ve worked long and hard on your outline and you believe that you’ve created a compelling pitch for the recommended action you want the decision-maker to take, you’re ready to translate your outline into the story that will take the person(s) step by step through your pitch to its conclusion. Make sure that the story proceeds methodically through the information, starting with a statement of the question you want to be answered or solved so that the decision-maker knows from the start the very decision they are being asked to make. Once the decision maker knows what they’ll be deciding, they’ll be more attuned to the evidence needed to support the decision you want them to make as you spotlight the most important merits for your core action or recommendation being adopted.

This step guarantees that they’ll be better able to tie the facts back to the core action or recommendation and understand how the facts either support or disprove the course of action being sought. Make sure that part of your appeal is to the person’s common sense and not only the facts and evidence. Sometimes decision-makers will make decisions on what their gut sense tells them and then look for facts to support it, so it is wise to appeal to both in your story. Avoid hyperbole and phrases that contain absolute negatives like “There will never be another…” or “No one has ever seen…” since these can result in a loss of credibility in your presentation, as negatives are always difficult to prove. Always make sure to begin the story with your strongest points because as they say: first impressions are enduring.

Make sure that the story starts out in a positive vein, and if you have to address or refute something you do it in the middle and not at the beginning or end. Close powerfully and explicitly tell the decision maker what it is you need them to do. Your closing should move the decider to action with a recap of the principal reasons they should take action and why your recommendation is the only response.

Give Your Story A Test Drive

Practice makes perfect, and sharing your story with others before the actual pitch can help you hone your pitch and give you the needed practice so that you’re comfortable with giving the pitch seamlessly. Choose a group of people to practice your pitch with and ask to track your story against your outline and to give you feedback on areas that you might have missed or might be overkill. Then incorporate their suggestions and refine the pitch until you think you have it in its final form. Choose one person whose decision-making style mirrors that of the person you’re pitching and pitch for them as if you were doing it for the intended decision-maker. Debrief them on what worked and what didn’t and if they’d have made the decision in your favor. Hone your presentation again until you’ve got it where you think it needs to be. You might even want to video this session so that you can watch not only your presentation but also their reactions to what you were saying at certain points in the pitch.

Decide What Final Form The Presentation Will Take

At this point, you already know a lot about the person you’re pitching, and you’ve spent a great deal of time honing your pitch to match their style. You’re at the point where all that’s left to do is help them understand what you need them to do, and the key to doing that effectively is selecting the right format the final presentation will take. Deciding what the final form is may not always be under your control, and that could go either way. It might be that the decision maker has preset the format to be what he/she prefers, and so understanding the best way to utilize the features of that format to showcase your pitch means making sure that you know and understand how best to showcase your information in a variety of ways. If you get to select the final form, be sure to choose one that you know makes it easiest for the decision-maker to best understand and be presented with the information. Knowing in advance if they prefer reports, executive summaries, slides, or even an email with key decisions and data points, followed by a face-to-face meeting or an in-person pitch, will go a long way to helping you showcase your idea in the most favorable light. No matter the presentation method—or if you’ve chosen it or not—as long as you’ve structured and crafted the pitch with the strategies above and ensured that you’ve placed what they are being asked to decide on early in the presentation, the presentation is pared down to include only the most salient points, your closing moves them to action, and you’ve told them everything that they need to know to make a decision, then you’ll be better positioned to be successful.

Remember that no matter what, you have to know your stuff, stand your ground, and do so as equals. When you step before the audience next time you pitch, have this clearly in your mind and know that you are there to help the decision maker understand what the circumstances demand of them, what they need to know to make the decision, and in doing this effectively, you’ll show them that you knew what you needed to know about the matter at hand too.

Let me know how your next pitch goes in the comments below.