How (not) to present an idea

About 5 years ago I was so stressed at work that a blood vessel popped in my eye. I was getting great results at work — the kind of up-and-to-the-right charts that usually only exist in stonks memes — but I couldn’t keep going like this. I needed more headcount for my team. I needed to convince my boss to hire more people or I was going to walk around bleeding from the eyes. 

So I put together a deck, the slides that ultimately made my career. I presented on the success we’d had so far, the various demands on our time, the exact method we would use to execute our work and keep building on that success, how long it takes a typical team member to put out 1 unit of work within the framework I was describing, and some of the more ambitious projects we weren’t working on because of time constraints. 

The last slide of the deck was a request for headcount. But I never got to that slide, because 5 slides from the end my boss stopped me and said “it sounds like what we should do is add more headcount.” Within six weeks I had hired and onboarded three more team members. 

If you have presented an idea at work and been brushed off — which you have, because everyone has — you probably wondered “why won’t people listen to me.” 

Depending on how frustrated you were, you may have thought other, less-charitable things, like:

• “This is bullshit”

• “Nobody respects me”

• “Why does [other person] always seem to get what they want” 

I can’t promise you will get what you want after reading this, but I can tell you that the way many people go about pitching ideas is at the source of their rejection. 

I’ve been in a position where I get pitched to for most of my career, and I have a pretty good track record of executing on my own pitches. So why are some pitches accepted and some ignored? 

For a pitch to be successful, you need to paint a picture of a world in which your idea is the obvious idea

A metaphor I’ve used with my teams before is that we are all standing back to back in an art gallery. Each of us is looking at a beautiful painting, painted by one the old masters or one of the new ones, and we look at that painting as though it’s the only painting in the world, the first and best and only way that anyone has ever used color. 

But of course there are other paintings — we just can’t see them. One of the challenges of business and management and just generally communicating with people is that we are standing back to back in an art gallery trying to describe our painting to someone who can never turn around and see it for themselves. Even worse, you aren’t trying to describe only what the painting looks like (e.g. “this painting of a barn and barnyard near sundown”), but how it makes you feel. How the brushstrokes and colors work beautifully together, but would be even more beautiful if just here, in this corner, you added a splash of red. 

That’s what you are asking for when you pitch an idea — to add a splash of red to a painting that the other person can’t see. How are they supposed to give you a yes or no, unless you can illustrate a vision of the painting you can see and they cannot?    

When you go to communicate that vision, you’ll quickly find it’s not so easy. A painting, just like the model of your work you carry in your own head, isn’t something expressed linearly through language — it’s experienced all at once in a single instant. You can’t just describe the part of the painting you want to add red to. You have to describe how your changes affect the entire system of the business, and it’s not always so easy to do this. 

Great pitches help your boss see the world the same way you see the world, and hopefully independently reach the conclusion that your idea is the right idea. There’s no exact formula for doing this, but these five questions cover most of the ground you need to cover.

1. What is the potential impact on the business? The biggest thing missing from most ideas. What is the material impact of your idea — not “customer delight” or “brand” or something else amorphous. What will be different about the business after your idea succeeds? (If it is something amorphous, you have to find a way to make it more morphous). 

2. What’s the lift required (time, budget, political capital) to make the idea happen? Lots of pitches underestimate time/budget or don’t include the logistical challenges of executing (e.g. “we should make a marketplace!” is the sort of idea easier said than done). But there are multiple types of resources in organizations, and political capital/general goodwill is one of them — if you’re asking your boss to request big resources from another team when your boss also wants to ask for big resources from that team for something else, one ask is going to take priority.  

3. What context do you have that the person you’re presenting to does not have? Why didn’t the person you’re presenting to have this idea already? You are probably closer to the work than they are, and that means you see things they can’t see. There’s a reason you think this is the obvious thing to do and they do not (yet). You have to paint a picture that makes it as obvious to them as it is to you.

4. What kind of prioritization is the person you’re presenting to facing right now? An executive has a hundred emails, pitches, concerns, priorities, etc. Your pitch needs to stand out from the pile they’re already working on, or else it just gets added to the pile. Understanding the biggest challenges a person is facing can help you tailor your presentation of the idea to solve those challenges.

5. Who can finally make the call and say “yes, let’s do this?” If it’s your boss, that’s great! But a lot of the time it’s not your boss — at least not completely — and you need to tailor your pitch to be passed up the chain. If you can convince your boss your idea is worthwhile, they’ll advocate for it, but you need to give them the tools to do that (just like you’re tailoring your pitch to your boss, they need to tailor a pitch to their peers/manager). 

You want to create a scenario where you are pitching to someone who can see your picture and imagine yours. Everyone all of the time is asking “how does this affect me,” and you want the answer to that question to be immediately apparent, and something you don’t have to explain.  

You can avoid most idea-presenting mistakes by asking “how easy is it for my manager to say yes to this”

Communication with others takes place when they understand what you're trying to get across to them. If they don't understand, then you are not communicating regardless of words, pictures, or anything else. People only understand things in terms of their experience, which means that you must get within their experience. – Saul Alinsky, Rules for Radicals

If you present an unstructured idea, you’re going to get an unstructured answer. I have at many points in my career been on the receiving end of ideas in Slack DMs (or, earlier on, in Google Chats), and usually these ideas are presented in the form of “it would be cool to do [thing].” 

Earlier in my career I would get a pitch like this and it wouldn’t register as a pitch at all. Then a couple of months later I would talk to my report and find out they were frustrated because they didn’t feel like their ideas were being listened to. I have since become a better manager in many ways and I’m more likely to recognize this when it happens, but still — I don’t think this counts as presenting an idea. 

Here is the simplest way to avoid most of the mistakes people make when presenting their ideas: ask yourself “how easy is it for my manager to say yes to this?” 

If a manager reads or listens to your pitch, do they have enough information to say “yes” (or “I’m on board, let me take it to my boss”) right away? Here are some of the common ways people miss:

• “I think it would be cool to do [thing].” I might agree with you, but this isn’t in the form of a proposal I can say yes to. What’s the impact? How long will it take? What makes this higher priority over other work?

• Presenting a list of things to do without resourcing or priorities. In any healthy business, you will be able to generate an infinite list of “things to do.” The hard question is not “what things are possible to do” but “which ones should we choose.” 

• Asking for a ton of resources for untested work. The more you ask for, the more you have to prove out the project. If you need a ton of resources, it will cost both those resources and political capital to get a project approved — so you need to raise confidence with some kind of experiment or rigorous third-party data/research that makes it clear why you’re right.

• (Most common) Not considering or presenting size of impact. I’ve heard pitches about how we should spend $10k+ on a webinar that would only get ~500 visitors (and in fact, I’ve watched it happen). Right now I’m in a business with 100k+ users and an intentionally small team — the ideas we consider need to be able to meaningfully drive 1,000+ users at a time. In my career, the biggest mistake I see in presenting ideas is in the presentation of ideas that are simply too small to have an impact of the size the business needs to grow. 

When you present an idea, it needs to be detailed enough that the person you’re talking to can approve it (or move it up the chain) right away. The exact format of that presentation — slides, document, Slack message, live meeting — will vary based on the idea. You might put together a bunch of materials and find that it was overkill (your boss would have approved the idea in a DM). You might have the idea shot down.

It’s still worth doing the work on the pitch. You can use the materials to share an approved idea with people on your team/other teams, or with contractors. You can reference a failed pitch 6-12 months down the line and pull out elements that were good for a different idea — this actually happens quite often. Even the most thought-out pitch will not always get approved, but this level of detail will always be useful.