Last night I ran a workshop on How To Pitch Ideas, hosted by the wonderful folks (Llewyn Paine, Emilie Thaler and  Cathie Toshach) at the Seattle IXDA chapter. The topics covered were generated by the attendees themselves at the session and I promised I’d write up notes, which you are reading now.

References:

• My popular essay: How To Pitch An Idea
• Checklist for great presentations
• How to get better feedback
• Getting Feedback on ideas without frustration (idea critiques explained)
• The Confessions of a Public Speaker

The important advice most people don’t want to hear

Pitching ideas is hard. Most of what we think we know about doing it well is inspired by TV shows and movies, where a charismatic, creative person magically convinces rooms full of recalcitrant people to follow their ideas. This rarely happens in real life. Most pitches fail to convince anyone. The reason most pitches fail to convince anyone is the person who is listening to the pitch often already has their own ideas for what they want to do, and even if they don’t, they are listening to dozens of competing pitches for the same resources. By the time you pitch them you’re often already too late. You can do everything right in your pitch and still fail.

It’s a rarely discussed fact in creative circles, but the more powerful you are, the fewer pitches you need to do. Always remember this. If you are the CEO of the organization or the grand emperor of the planet Pitchus in the Andromeda galaxy, people pitch you. They pitch you because you have the power. Any job that demand you pitch all the time reflects the lack of true authority you have over creative decisions. This means persuasion is a central skill in what you do, and the sooner you treat it as a central skill the better (See 5 dangerous ideas).

The best way to persuade people is in informal settings. You often earn this right only by cultivating a reputation for having good ideas, which takes time. And the best people to bother trying to persuade are decision makers (or people one step closer to decision makers than you are). Real influence is having the kind of relationship where you can go talk to powerful people about an idea informally, without the unavoidable theatrics that come in to play in big meetings. In a big meeting people in power can’t speak honestly: they know that 5 or more people are listening, each of whom wants to hear different things. An executive, or client, is less open to ideas in big meetings than they would be in nearly any other setting (such as a private chat in their office or a conversation over coffee).

The goal then is to develop relationships and credibility with the important people in your world so that your formal pitches, in idea review meetings or grand product planning sessions, are not the first time decision makers have been pitched by you. You want big meetings to be closer to formalities, or at least situations where you understand who in the room are already your supporters, and what approach you need to take to try and convince those in the room who are naturally critical or have goals that don’t match yours.

It matters who makes the pitch

We judge people heavily based on their reputation. Someone you trust could give the same pitch as someone you didn’t, and you’d respond to “the pitch” differently. Reputation matters. How much latitude and benefit of doubt you will get when you pitch something depends on what you’ve pitched before, what the outcome was and how much respect they generally have for you work. This means a few things. First, you might have an amazing idea that requires a far better reputation than you have (e.g. on your first day at work it’d be a mistake to pitch reorganizing the entire organization). Second, for any given idea there might be someone other than the person who came up with it who is the best person to pitch it. This might mean asking your boss to make the pitch or a coworker. You might need to decide if you care enough about the idea to let someone else make the pitch on its behalf.

Topics, situations and answers

I started the workshop with an option to use my slidedeck, or to build a list of situations from attendees and spend the time discussing them. They chose the later (I pitched them harder on this option, and I won!). Here’s the list we worked from during the workshop, with my notes on the answers.

• The decision maker already has an idea. This means you are in a dog and pony show – the pitch meeting is theater. They’ve already had whatever brainstorming discussions they’ve wanted to have with the people they respect. You need to figure out how to get involved earlier in the process so you are pitching at a time when ideas are being considered. If the decision maker has an idea already, whose was it? When did that person talk to the decision maker? How can you time things earlier for the next project or next idea? Of course you can also try to pitch them on why your idea is even better than they one they already have.
• What are counter-tactics for meetings where people delay and filibusters new ideas? In any meeting ask the question: who is in charge here? Any meeting that is poorly run, or more precisely, is run in a way where most new ideas are shot down is not an accident. The person in charge is running it that way for a reason (one potential reason is they are incompetent, but for the hopes of a fair pitching landscape the negative effect is similar). Ask yourself: what is the reason? What do they have to gain from having a meeting that’s so hostile, or so incompetent? This situation is similar to the first: it’s likely the frustrating experience of the discussion is really about the fact that someone in power already has a plan. The meeting is just for show to make everyone feel like an honest discussion is happening.
• How do I get better at pitching? Pitching is a skill. It’s a kind of performance. The only way to get better at any skill is to practice. When you find a new idea grab a coworker or friend and pitch them on the idea. Don’t pick your warm and fuzzy friends – pick people who are smart and critical. Let them ask you question and pick your idea, and your pitch apart. Then do it again, and again, learning each time. The more important a particular idea/pitch is to you, the more practice you should have with it before you do the pitch to the person in power. Develop relationships with coworkers where you practice pitches on each other – not to stroke your ego but to get thoughtful feedback you need to hear to improve your pitch before you actually do it.
• Does who I’m pitching to matter? What good is a great pitch to the wrong person? Or more precisely, how can you know if your pitch is any good if it’s not crafted for the person you want to influence? Understanding who you are pitching might be more important than the pitch itself. If you had a great idea, would you pitch it to Justin Bieber the same way you’d pitch it to the Pope? You should study who is going to be in the room when you give a pitch: what are each of their goals? their preferences? what was the last idea they supported? what was the last idea they rejected? What are their goals for this quarter or year? Who do you know that successfully pitched them and what advice do they have? All of those things give you valuable data about how to tell your story differently, or possibly even to pick a different idea to pitch them on.
• Is there a secret system for perfect pitches? There is no secret system for anything. I recommend thinking about 5 / 30 / 300. You should be able to explain your idea in 5 second, 30 second and 300 second versions. Distill it down and down until it’s a single sentence. If you do this well it will be interesting enough that the person you pitch will instinctively ask a question, leading to your 30 second version of the pitch. And if you do that well, they’ll ask for more, and you’ll be ready to give them  the 4 or 5 minute version.
• If I get access to the key decision maker, how should I pitch them? Concision is the most important thing. Most creative people who have developed a good idea assume they have to explain the process for how they found the idea in the pitch. This is a big mistake. How you invented something has no impact on whether the thing you invented solves a problem for someone or not. Put your pride aside and focus on what the idea can do and who it can do it for. When you’re famous you can explain how you did it, don’t worry until then.
• In my team meetings my ideas get ignored but are proven right later. If this happens often I’d think about who in the room, if I convinced of I was wrongfully ignored, would do anything different in the next meeting to help me. I’d try to document my experience: perhaps by taking meeting notes that just happen to include my suggestion. Then when my ignored suggestion is shown later to have been right, I’d take that documentation and go talk, in private, to the person in the room who could have changed things. I’d tell them the story: “I pitched this idea last month and it was ignored, and look now. what could I do differently next time I have a good idea to get more support for it?” And see what they say. Odds are high they themselves will listen to you differently from now on.
• How do you pitch people you don’t know? Pitching is similar to dating. The best advice is to listen first. Ask questions that help you figure out who you are  talking to. What are your goals this year? What frustrations do you have? What problems are you trying to solve? In letting them talk first you give yourself the benefit of matching, in your mind, the ideas you have to the situation they are in.
• My ideas always get shot down without a fair debate. Help? Most organizations use phrases called idea killers that unfairly kill ideas. They include “We don’t have time” or “We tried that already” or even “We don’t do that here.” These sound smart but they are substance free. Rheotically they have no substance. You should familiarize yourself with the common idea killers in your world and practice responses that keep the conversation going. Expect to hear them and have a response you’ve already crafted. Healthy creative organizations have leaders who kill idea killers for you.
• Can you use emotion to your advantage? We are emotional creatures and pay great attention to how invested people seem to be in whatever they are telling us. Most people hide their emotions around even their own ideas. This is a mistake. All things equal you will be more convincing if you seem passionate and engaged as you talk about your idea. Showing that you’ve done your homework (preferably by your ability to answer questions rather than burying people in details) is another way to convey how committed you are to the idea you’re talking about. Stories have emotional power that data does not – a pitch involving a single well told story of a real person with a real problem can have more impact than thousands of dollars worth of demographic research reports.
• How to use data. Data is only useful if it fits the goals of the people you are pitching to. Facts can help tell a story, but only in the fact has two qualities: 1) it hits directly on a situation the people you are pitching care about 2) your idea presents a solution to that problem. Data is a double-edged sword though. You can easily fall into the trap of arguing with someone about whether your data, or their data, is better, an argument that is very hard to win. Ideally data and research were a natural part of your process for how you developed your idea in the first place, in which case it will be natural for you to refer to it as part of your story. Searching for supporting data only to help sell something in a pitch is guaranteed to suffer from confirmation bias – something a wise audience will spot and question, hurting your credibility, so be careful.
• How to find the right story to tell? A story has three parts: a character, a narrative and a conclusion. Every person and every culture prefers different characters, narratives and conclusions. There is no single story that connects with everyone. I would study the goals of the organization or project to look for characters and narratives to use. Pitching a hospital? the main character is likely a patient, or a doctor, or a technician. The narrative might be: bills are hard to figure out. The conclusion is perhaps, if we follow the idea I’m proposing we can improve the readability of bills by significantly (or if you want have data to support it, XX%).
• How to get people to fight your battles for you. People are most likely to fight your battle for you if they don’t think it’s just your battle. If they see (perhaps because you tell them) that by supporting you they get what they want, it’s natural for them to get involved. Any decent boss naturally shares your interests as they want you to succeed and will help you for that reason alone. Sadly not all bosses are decent, and even the decent ones aren’t necessarily politically savvy. You may need to walk them through why supporting your pitch is in their interest and make specific requests for what you want them to do to (“Can you mention this at the next manager’s meeting?” or “since you like this idea, can you support me when I pitch it to the team?”)

Have other pitch related questions? Leave a comment.