Transcript- How to Pitch Ideas (So People Actually Hear Them)

How to Pitch Ideas (So People Actually Hear Them)…

by Angela McConnell

(Edited for length and clarity)
Welcome, everybody, to How to Pitch Ideas So People Actually Hear Them.

Very excited to give this talk to you all because I think your ability to share ideas is absolutely crucial to being able to do good work and being able to advance.

For those of you who don't already know who I am, I'm Holly. I'm WIMDI's founder. I'm also an executive coach for Women in Male-Dominated Industries. In a past life, almost 10 years ago now, I was a mining engineer.

I was the person in charge of building mine plans about what those big yellow trucks you see on the Discovery Channel do.

I was a huge nerd about rocks and also a huge nerd about feminism, and both of those things kind of brought me to the place that I am now, where I work with women just like you to help them advance their careers and lead better and quite honestly, get more power in the kind of industries that we all love, which are unfortunately for us, almost entirely men.

I'm grateful to live and work and build WIMDI largely from the land of the Squamish, the Musqueam, Tsleil-Waututh First Nations.

Why Pitching Ideas is a Crucial Career Skill

Pitching ideas is a crucial career skill, especially as you continue to rise up in level in your career, it becomes more and more important that you're not just the person executing the ideas, you're the person coming up with the ideas that people below you will be executing.

Your job is to go out and point the direction that the company will go in and lead it to a place that's actually going to be good for the company.

The 4 Biggest Mistakes You Can Make in a Pitch

I deal with this all the time in my coaching practise, both in the individuals that I work with, but also in my group program, The Game Changing Year, people that I work with are always coming up with new ideas, sharing them out loud, and they tend to make four big mistakes along the way that make it so that their ideas don't get heard and don't get adopted.

And what I want for you is that your ideas do get heard and adopted. So, I'm going to teach you the four ways that people mess it up. And I'm also going to teach you the four things that you need to get right in order to have people actually hear your ideas.

We're going to use an example of a client of mine named Sonia. Sonia wants to implement something called continuous deployment.

Some of you in the room might be in the software industry and might understand what this means automatically and implicitly, but for those of you who don't, you're probably sitting there going, "Well, what the hell is continuous deployment, Holly?"

The short version is continuous deployment refers to the way that software companies release software into the world so that we can all use it. These might be things like updates, they might be new features, they might be bug fixes, or they might be entirely new versions.

Continuous deployment means that they release those things all the time. That's the continuous part of it. They might, every minute of every day, release a brand-new feature, or at least daily.

Every single time somebody finishes writing code for a new feature or a fix, that gets deployed almost immediately and then is able to be used by the users, as opposed to the way that it used to be done was that they would sort of pile a bunch of brand new fixes or new features or improvements together and then release those all as one clump.

If you remember back in the day, you know, Windows 98 for example. We would wait years, and years, and years for Windows 98 to become Windows XP and we would get a pile of DVDs that we'd have to install on our computers.

So that's the extreme version of, not continuous deployment, that's periodic where you get a release every once in a while. These days, you'll get them much more frequently than that. They might be weekly; they might be monthly.

For most companies they're doing continuous deployment because it gets things in the hands of people much sooner and they don't have to wait so long.

There's a couple of key benefits of continuous deployment, of this approach. The first benefit is, like I said, you get to deliver features more frequently. If I'm an end user, I don't have to wait weeks, and weeks, and weeks to get an improvement. I can have it in my hands right now.

Secondly, it helps you reduce the number of bugs or errors that you're shipping in your code. And the reason that that's true is because you're not clumping a bunch of things all together and releasing them all at once. You're putting them out in little bite-sized pieces.

So, it's easier to tell if there's a problem or if there's going to be a problem that comes just from that single thing that you've released as opposed to whether there's going to be a problem from these 15 things that you released.

And finally, it helps you reduce the time it takes to both test and debug those releases. Because there's fewer things in a single packet getting released, it doesn't take as long to test it.

It's much simpler and it's much easier to tell if something goes wrong, what is going wrong because it's not sort of like a tangled pile of necklaces that you have to tear apart before you can even figure out which one is the faulty one.

Sonia, when she goes to pitch this idea, she says what most people say when they go and pitch continuous deployment, which is, "Hey, it's best practise, everybody does it."

And that's true, everybody is doing it. All the big software companies, you know, the FAANGs, Google, Meta, Apple, like every single one of these is doing some version of continuous deployment and it's considered best practise in the software industry.

When she says this, everybody in the engineering side of the business is completely sold. The engineering director thinks it's a great idea, the CTO thinks it's a great idea. They go, "Yeah, this is what everybody's doing. This is what Google's doing, we're in."

But, when Sonia says the same thing to the CEO, she is not interested at all. She says,

Look, Sonia, absolutely not. I don't want to spend any time on this. I've got more important things to worry about than some esoteric best practises software developer nonsense. I'm in deep shit with the board; I'm just trying not to get fired.

We haven't hit our roadmap in years. They think we're complete clowns just wasting time and messing around on stuff like this instead of delivering. We need to focus on building the features we're going to sell next. And hell, we just need to hurry up and develop the features our competitors have already released and they're currently outcompeting us on. Now get the hell out of my office and go do some real work.

So, yikes, this did not go the way that Sonia was hoping it would go. She hoped that she would get this big excited yes, like she got from everybody on her team and instead, she got the CEO screaming at her. Ugh, not ideal. So how did this go so wrong?

Why is it that they loved it so much and she hated it so much? Well, if I'm honest, this was a pitch for engineering and not a pitch for the CEO.

If you look at all of the benefits here of continuous deployment, these are all things that make engineers happy. They're the ones that care about delivering features.

They are the ones that have to deal with the bugs when they accidentally get shipped. They're the ones that have to fix them and they're the ones that have to do all the testing. All of this helps them with what they care about.

But for the CEO, she couldn't care less about this stuff. I mean, it's nice I guess, but it doesn't really affect her in any way. It doesn't really deal with anything that she's actually concerned about or that she thinks about on a day-to-day basis.

Lesson #1: Tailor Your Pitch to the Correct Audience

This brings us to lesson number one, which is that you need to make your pitch tailored. You can't use the same pitch with every single person that you're going to talk to. Even if it was successful over there, it might not be successful over here.

You have to make it match this person and their unique concerns; not just use the same old pitch you've used for everybody else. So, let's take a look at some of the things the CEO said there so we can understand what it is this person is actually looking for.

So one of the things she said is, "Look, we need to focus on building the features we're going to sell next, and we need to develop the features they're already outcompeting us on."

She may as well be saying, "Look, we need to develop faster." She could be screaming that at us. And in fact, she basically was. We need to go faster.

Okay, let's take a look at what we said about continuous deployment and see if we can find an angle where we can make it seem like continuous deployment will help us go faster. That's the thing she cares about, right?

Let's start with number one, delivering features more frequently. This sounds like go faster, right? "More frequently, sounds faster." But I would say it's not really the same thing.

When the CEO says we need to go faster, what she means is, "I want to release this new thing that we're putting out to customers six months sooner, a year sooner, two years sooner."

She doesn't mean, "I don't want to wait until Friday to release it, I want to put it out on Tuesday." Which is sort of more what continuous deployment is going to help with. Because right now, this company is already releasing on a weekly basis.

They could speed that up and technically, make it a little more frequent. But that's not really what she means. And it's not really what the board is upset about. When the board says, "We're not hitting our roadmap, we're not moving things out the door fast enough," they don't mean like a difference of three days. They mean something much bigger.
Let's cross that off the list. I don't think we're going to get what we need there.

What about reducing the number of bugs shipped? She would only care about the bugs if all the customers had a massive revolt about the quality of the software maybe, but this doesn't really affect her day-to-day and it didn't even honestly show up in the whole rant that she gave to poor Sonia a few minutes ago. We'll cross that off the list too.

The last thing is reducing the time it takes to test and debug. Now I think this one actually has some potential for us, because if we reduce the amount of time it takes us to test and debug, that means that the extra time that we're not spending testing and debugging is time we could spend writing new software, getting the software out the door faster, just like the CEO wants.

Let's go for that angle. Sonia now tries and says to the CEO, "Hey, let's do continuous deployment. It'll save time so we can go faster." And the CEO's says, "Yeah, okay, but like how much?"
Honestly, a pretty reasonable question. We probably should have seen that coming.

Lesson #2: Quantify Your Pitch

This brings us to lesson number two, which is we've got to make it quantified, because the CEO or really any leader in a company is always making trade-offs between multiple options, multiple ideas they could be pursuing. It might be this one or it might be another.

What are we going to do with the limited amount of time and resources that we have? She wants to understand how much of an impact this is going to have. And the fastest, easiest shortcut for us to get there is to quantify it in terms of dollars, in terms of hours, in terms of percentages.

Let's try to do that and see if we can answer her question. So here we're talking about this benefit of reducing the time for testing and debugging. Let's do a little bit of math.

Right now, Sonia estimates that we spend about 9 1/2 hours per week, each developer, doing testing and debugging of code they've already written. She thinks if they do continuous deployment, conservatively, they could estimate a 10% reduction in the amount of time they're spending on that testing and debugging. Overall, just under an hour every week for every single developer on the team.

An hour a week for 36 developers, which is how many they have on the team, works out to be about 34 hours saved if we do this continuous deployment project. Cool. Is that a lot though? Is 34 hours good, bad? What does that mean?

Let's quantify this in terms of a percentage. We've got 36 developers. Let's assume they work about 30 hours a week that are truly productive. Meaning they're writing code, you know, they have time that they're in meetings or time that they're just goofing around a little bit on Facebook or something like that. Let's say they're spending about 30 hours actually writing code.

That means that they're spending about 1,000 hours a week as a collective doing productive feature development work. So, we've got 34 hours saved. Out of those 10,000 hours, it works out to be 3.2%. All right, let's tell the CEO.

We'll say, "Hey, we should do continuous deployment. It'll save time so we can go faster." She says, "Yeah, but how much?" We say, "3.2%." And she says, "Stop wasting my time with this. Get out of my office."

Because 3.2% is just not that impressive, right? I want it to be. I want this thing to work for Sonia, but at the end of the day, 3.2% is just not that exciting. Rats. Back to the drawing board again for us because we haven't quite found the way to sell it yet to this woman.

Let's come back to point number one, make it tailored. We talked earlier about how everything the CEO was saying kind of boiled down to we need to develop faster. But I don't actually think this is really it for the CEO. She wants to go faster, but she doesn't care about speed in and of itself.

She wants to go fast so she can build more features. That's what she talked about. She's said, "We need to go faster so that we can release more features, you know, and compete with our competitors".

Okay, what if we think about it in terms of building features? Sonia's got a great idea for that. She says, "Well look, we're saving 34.2 hours and every single developer on the team is productive for roughly 30 hours a week."

Another way that we could say this is, "Let's do continuous deployment, it'll free up one developer to code all your pet projects, all those features you want us to be releasing that you want to get to market faster, you'll have one developer dedicated just to that. How nice".

Suddenly, the CEO says, "Ooh, okay, that's interesting. I could have my own minion? Yes, yes please." So, we've finally done it. We finally found something that gets the CEO to stop screaming at us. Hooray, hooray for us.

I think we can actually do a little bit better than this. I know the CEO's excited, but I think we could do better.

How to Tailor & Quantify a Pitch (With a Case Study!)

And friends, what we're really doing here in step one where we're trying to tailor our pitch to our audience, we're actually playing a game of darts and where we're trying to hit a bullseye and we're throwing darts at the board and seeing where they'll stick.

If I'm honest, that first pitch about, you know, it being standard practise, this didn't even hit the board at all. The dart went flying in a completely different direction and hit the poor engineering director in the shoulder, impaling him. Now he has to go to the hospital. Whoops. Bad throw. Not ideal.

When we came in with our 3.2%, we got it on the board. It's something the CEO cares about, going faster, but it just wasn't that appealing. And it wasn't really close enough to something she cared about. It didn't really land close enough for it to be worth any points to us.

But with this one developer thing, we're finally getting closer to the centre, finally getting closer to the thing that she really wants in a way that feels significant. Now we're on the board in a good position, but I think we can still get to the centre.

Let's see if we can do that. Looking back at what she was talking about earlier, you know we talked about how she wants to develop faster, but that's just so she can build more features.

I think something similar is going on with this features thing. She wants to build features, but she doesn't care about the features. She truly doesn't care like if such and such feature exists for the customers.

Really what she wants at the end of the day, is to build those features so she can sell them. She wants to make money. That's what this is all about.

When she's busy screaming about we're not hitting our roadmap, we're not developing fast enough, what she's saying is, "I need to make more money so I can tell board I'm making money. I don't care how we get there, I just want it to be fast. I want there to be features so we can sell them and we can make money."

Let's translate this pitch that we've got here about continuous deployment into some money since that's what the CEO is actually interested in.

I mentioned earlier that Sonia is a developer at a car share company. We're going to talk about how this connects with some money. Locally, here in Vancouver, there's a car share company called EVO. And EVO's a pretty big deal.

There's 940,000 members, which is actually larger than the population of the City of Vancouver where I live. It includes the suburbs as well, which is part of why that's true.

It's estimated that one in three households has access to or uses EVO, which is amazing. It's shocking the amount of penetration that EVO has.

It's this highly responsive, minute-by-minute rental and it kind of replaces car ownership for a lot of folks in the city, or augments car ownership for lots of people in the city.

It's only got one problem and that is what Reddit calls the EVO dead zone.

This means that sometimes you open up the app and you know you're there on the little blue dot and you realise there's not an EVO within anywhere close to you that you could walk for 40 minutes and you still wouldn't find one of these EVOs, which is tough because you only have 30 minutes to get to your EVO before they give away your rental.

So sometimes you'll find yourself where there's just no EVOs near you at all. What you end up doing is you sit there and you refresh your phone, and you refresh your phone, and you refresh your phone until finally one appears, and you go, "Oh, thank God."

You click on it to try to book it, and boom it disappears, because everybody in your neighbourhood is trying to do the exact same thing as you.

Everybody's scrambling for that single car that just showed up. If you're anything like me, then you just throw your phone in frustration and vow never to use EVO again. Not ideal.

For a long time now, the CEO has had an idea about how to solve this. And you can see she's really excited about it because she's got dollar signs in her eyes.

She said, "Okay, let's introduce something called EVO Concierge membership." EVO Concierge membership means that inside of the app you can set up a radius and a timeframe where you say, "Okay, there's no cars near me right now, but EVO, I want you to go and check automatically without my input, within, you know, this amount of walking distance for the next half an hour, check and check and check. And if a car arrives in that zone, book it automatically and let me know you've done it."

It takes all of that manual checking out and it just does it for you. You jump to the front of the line; your neighbours can't steal your car. Pretty good. Yum, yum, yum. If they would implement this, EVO would now have two tiers of service.

They'd have EVO Classic, the one that we all have now, where we don't pay any monthly subscription fee, just the normal car rental fees. We book our cars manually; we fall victim to the dead zone sometimes and life kind of sucks.

Or, we can have EVO Concierge for a mere $10 a month where robots book your cars, we live in the future and everything is amazing. Sounds pretty good. I know which one I would be buying. It's very exciting, right?

The CEO has wanted to do this for a really long time because there's money on the line. And friends, it's a lot of money on the line. EVO has 940,000 members. If we assume 5% of them decide to go with Concierge, that's 47,000 concierge clients.

And if they're paying $10 a month or $120 a year, that works out to $5.6 million just for EVO Concierge, in new revenue, that they don't even make right now. Pretty amazing, right? So that $5.6 million is right in the middle of that bullseye.

Imagine if we could tell the CEO that if we do this, she'll get 5.6 million bucks. I think that's going to be pretty exciting. Let's hear Sonia pitch it.

Sonia says, "Hey, I think we should do continuous deployment. Tom asked me to look at it a few months ago. It'll help reduce the number of dependencies in the new commits and improve our regression testing and accelerate engineering feedback loops.

Plus, it'll free up one dev to build EVO Concierge. And when I did the calculations, I assumed 5% of our customers might sign up. Although who knows? It could be less than that if not as many customers sign up for it as we think.

But if it all works out, then I think we can make $5.6 million in new revenue from this continuous deployment project."

Meanwhile, the CEO has fallen asleep. This pitch did not work, did not land. Ugh. Sorry, Sonia, another L to take home.

Lesson #3: Make Your Pitch Concise

The challenge here is that Sonia made a great pitch but she didn't make it concise. It was hard to tell what she was actually talking about because there's just so much detail coming out of her mouth.

The tragedy is when you read through all of this, you can hardly find the miracle $5.6 million that we've managed to create out of this project. It's hidden. I've had to actually highlight it here to make it visible.

The CEO, by the time we get to this $5.6 million has long been asleep. Not paying attention, discounted us, moved on.

A couple of tips for you all to help make your pitch more concise. Number one, no background or story. I don't want to hear how you got here, I don't want to hear about the process it took, none of that. Just tell me the results.

Also, don't include any technical details. You want to have some of these in your back pocket in case you get asked about them but one of the challenges most of us technical people have is, we fall so in love with the technical details and they're so important to us, that we think they're important to everybody else.

This CEO is not one of those people. Truly, this is a CEO who wonders when you know AI is going to allow them to replace all the employees. She is not technically competent.

And finally, don't include any information that raises questions. You want your pitch to sound all amazing, all the time, not all amazing with a side of risk and maybe we shouldn't do it. We don't want to create any kind of doubt in the mind of the person that we're pitching to.

Anything that could raise a question mark, we're going to cut right out of our pitch. Okay, so let's see what needs to change from what Sonia just did.

She starts out by saying, "I think we should do continuous deployment." Great, I love it. That's easy. We can keep that part. It just tells us what we're talking about. No big deal.

Then she says, "Tom asked me to look at it a few months ago," meh, cut. I don't care what Tom said. Doesn't matter. This is just background information, which we said we're going to cut.

Then she goes, "It'll help reduce the number of dependencies, new commits, improve progression testing, accelerate engineering feedback loops." These are all highly technical details.

Some of you who work in the tech industry might understand what most of this means. If any of you don't work in the tech industry, do you even understand this? Probably not.

This is all the information that we're going to cut because it's not going to resonate with the CEO and it also hides the part about $5.6 million. We want to make sure that we get to that part sooner. So cut all of that.

And she says, "Plus it'll free up one dev to build EVO Concierge." Okay, that I don't mind this. The CEO likes this concept. She's getting the feature she wants. There's something in it for her; we can keep this part.

Then she goes on to say, "Well when I did the calculations, I assume 5% of our customers would sign up." We're going to cut that. That's background information that tells us how we got there. She doesn't need to know what the assumptions are.

You might want to have this information in your back pocket. She might ask you questions about this, but it doesn't need to be in that initial pitch, in that initial kind of open her eyes, get her excited, moment.

Then she goes on to say, "Okay, although who knows? It could be less than that if not as many customers sign up for it as we think." And Sonia, I love you, but what is this doing in here?

Why would we say to the CEO, "Oh, it could be 5% but I could be completely wrong and maybe we'll make no money on this." No, we're not going to insert this now, we're going to cut this out of the list.

And then we go, "Okay, well if it all works out, then we can make $5.6 million in new revenue from this continuous deployment project." And there's parts of this that I like. I would say we're going to cut out the first little bit and the last little bit, but the part about $5.6 million is gold, and we're holding onto that.

All right, Sonia, we've redlined a lot of this pitch. But we've got I think a slimmed down, more nimble version that we can now deliver to the CEO. Let's clean it up and see what it looks like.

The new version goes, "I think we should do continuous deployment. You'll free up one developer to build EVO Concierge so we can make $5.6 million a year more.

Cool, great. I can see what the benefit is to me. 5.6 million bucks in EVO Concierge. It's right there, snappy. Love it. Much better.

Okay, so let's try it again with the CEO now that we've done our little editing behind the scenes. So you go into her office, she's not excited to see you. Why would she be? This hasn't gone well so far, but she's willing to give it another shot.

Okay, so now Sonia goes, "Okay, so I was hoping, maybe, you'd consider prioritising a continuous deployment project? Um, it might free up like one...one-ish developer so we could build EVO concierge this year and well, you know, that could be worth $5.6 million per year in revenue, you know, but only if you think it's actually worth some of our time to try it."

This went terribly. The CEO gave up on us and started answering her emails and forgot that we were here. Because we delivered this so poorly, Sonia. We could have done this better.

Lesson #4: Make Your Pitch Powerful

The challenge that we ran into here, even though we've got a great pitch, is that we didn't make that pitch powerfully. We undercut all the amazing-ness with how we did the delivery.

I'm going to give you three practical steps that you can follow to help improve delivery. First is the amount of softening words that Sonia used here. I've highlighted them here on the slide just so you can see there's a whole bunch of words that tend to make her pitch softer, smaller, less bold.

Things like "hoping," "maybe," "consider," "might." These all introduce a little less certainty, a little more doubt. She's got, of course a lot of ums, likes, uh, wells, question marks, a little bit of up-speak in there too.

All those things, again, help soften the message and undercut the power of it. And at the end, we're even starting in with, "Oh, but only if you think we should actually do it." We don't need any of that. That softens this up to mush.

We're going to cut all of those little linguistics things that soften up our language. Then we're going to pay attention to body language. Sonia here, I don't know if you all noticed, she had a festival of faces going on while she was making this pitch and none of them looked particularly excited.

She looks nervous, terrified, maybe a bit like a scammer in some of these. None of this says this is a face of somebody that I should trust and also who trusts what she's saying. When you show up with a face like this, you telegraph that there's a reason to be concerned or to not trust what's coming out of your mouth.

What we really want for Sonia, is for her to show up with open and expansive and excited body language that means in her face, but it also means in her physical rest of her body as well, which you can't see in this little avatar.

We don't want to be doing things like fidgeting. We don't want to have our shoulders hunched forward. We don't want to be crunched up trying to take us up as little space.

I'm not saying you all have to man-spread in the boardroom or something like that. But you want to be sitting there, shoulders back, eyes open, face excited, sitting relatively still and ready to go tell somebody about your amazing cool idea, not cowering in fear that they'll notice your terrible bad idea.

Finally, I want you to think about tone of voice. A bunch of the things that happened here with Sonia's pitch as performed by me are she showed up quiet, uncertain, nervous, and apologetic. And that saps all the power from this pitch.

Here's how we can fix that. Instead of trailing off, talking really quiet towards the end because she's not really not sure, we want to make sure that she stays at a normal volume throughout her entire pitch.

You don't want to be yelling, but you want to make sure that you're talking like a normal human being and not talking quieter and quieter and quieter because you want to sink into the background because it's not going well. So normal volume.

Then you want to show up with as much certainty in your voice as you can. You have a massive amount of power to control how somebody perceives your message based on how you show up. Somebody can show up with an amazing idea that they sound unsure about and you'll think, "I think this is a trick. I think this might be a scam because it sounds good, but they sound nervous, and I don't understand why and so I don't trust the situation."

So you want to show up as certain as you can and rather than nervous, as confident as you can. Now friends, this is a tale as old as time. You show up to a talk for women and somebody's says, "Ladies, have you tried being more confident?" Ick, I hate it. I know.

What I want you to be able to do with this tone of voice stuff is practise over and over and over again. The more you practise this, the easier it will be for you to come across as confident.

Sometimes, you will have to try to put it on. The truth is, before I came to this talk tonight, I did not feel any of these things. I didn't feel certain. I didn't feel confident. I had to put this on as a persona when I showed up here.

When I practised this talk two days ago, I put on that persona and it sounded terrible. Practise really does help you get to a place where the certainty and the confidence you want to project can shine through. So put it on like a suit and then practise living in it and it'll eventually come.

Finally, the last thing that Sonia did, that was really a challenge for her was that she showed up apologetic. There's nothing for her to apologise for this, this thing is great. She's not asking for permission. You are not asking for permission.

I get that that's literally what's happening. You're going, "Can I do this project?", Asking the CEO for her blessing. But actually, what you're doing is you are delivering the CEO a $5.6 million gift. You have to act like that.

Yes, you're asking for her approval to get this gift, I guess, but this is fundamentally a great thing that you come to her with. You have an amazing business opportunity.

Show up that way. Not like you're looking for permission. Show up like you've got something amazing for her to do. It'll change everything about how you show up.

Let’s Hear the Pitch Again With Tips Implemented

All right, so let's hear Sonia do it one last time trying to work these last few things in.

So, she goes to the CEO and she says, "Hey, let's do continuous deployment. It'll free up one developer, we can build EVO concierge and then we can make $5.6 million a year more."

And the CEO finally goes, "Hell yes, I'd love to do it." Hooray. Amazing. So exciting.

This is the same idea that had the CEO screaming at her, ordering her out of her office, checking her email, falling asleep. It's the exact same thing, but just framed differently, quantified, made more concise, and delivered with confidence. It's amazing what those four little things will do.

Your Amazing Pitch Checklist

Friends let's go over all the individual tips that you need to make sure you get this right. Number one, we're going to make it tailored. So that means that you've got to first figure out what the person you're pitching cares about.

It might be different than what the people you've pitched previously have cared about. And you want to make sure that the thing that you are talking about solves the problem that they care about.

Then talk about your project and whatever those terms are. Whatever terms that person cares about, that's the one you're going to talk about. And then you want to put it at the centre of the dartboard.

You might find as you look at what this person cares about, that they care about a lot of stuff. There might be six or seven things that would work that you could sort of talk about your project in that way.

We went through that tonight in the presentation. We could talk about speed, we could talk about features, we could talk about $5.6 million. You want to pick the thing that you think will resonate most, that they'll care about most and put it at the centre of the dartboard.

Then you want to quantify it, go do the math to figure out what this is going to be worth. Your math doesn't have to be perfect here. It can be order of magnitude.

You'll notice some of the assumptions that we made, you know, is continuous deployment going to improve things by exactly 10%? Could it be 15, might it be eight? Sure.

Either way it's going to be relatively close to 3.2%, it's probably not going to improve things by 80%, right? So, we get a sense of whether or not this is kind of going to work.

Given that this ended up at 3.2%, you know, we might improve that by 50% and then wow, a 6% improvement, it's still not going to get the CEO that excited. So do the math, make your best estimates, but know that they don't have to be perfect. You're looking for order of magnitude math here, at least initially.

Demo – An IRL Pitch (with Feedback!)

All right, friends, now it's demo time. I said to you earlier that we would do a demo.

Holly - Hi Louisa, how are you?

Louisa - I'm doing well, thanks Holly.

H- All right, so friends, I'll sort of explain what we're going to do here. Louisa has watched this presentation. I didn't give Louisa this presentation before this, it's all brand new. So we're going to have her live, in real-time for us, practise doing this with a pitch that she's had to do at work.

Louisa and I have talked before, and I've asked her on purpose to make some mistakes in this moment because what I'm going to do as Louisa shares with us and what we're all going to do in the room is we're going to critique her little pitch that she gives to us.

We're going to share what we think she did well and we're going to share what we think she can improve. But Louisa, who by the way, is amazing at this, is going to make some mistakes on purpose.

I want to make an agreement with everybody in the room that we all think Louisa is amazing and any mistake she makes, she put that in on purpose just for us. Sound good? Great.

Okay, so Louisa, you've got an idea to pitch. Tell us your pitch. And friends, take notes and then I'll ask you to share in the chat the things that you see. Okay.

L - And feel free to rip me apart. I have no ego.

H - How can you have ego when you're dressed as a cow, Louisa?

L - Exactly.

H - By the way, Louisa is dressed as a cow to obscure her identity. That's why. All right, Louisa, share your pitch with us.

L - Okay, so um, right now, our small docs team, we have only two people and we're ah, really slowed down by a clunky authoring tool.

Um, ah, I think we should migrate to a more efficient authoring tool and adopt a docs-as-code methodology, which could reduce our publishing time by at least 20%.

Um, I think it could really improve team morale and satisfaction and even save us, ah $25,000 a year in tooling fees because we're switching to an open source, ah tool.

Um, this shift would also help us, ah, collaborate easier with, ah, engineers and scale our documentation more effectively without requiring additional headcount. Um, I know it's a really big change and it will require some upfront investment, but I think it will allow us to scale documentation alongside the company's growth.

H - Great. Okay, Louisa, thank you. Let's talk about some of the things that we loved that Louisa did. What do we love, friends, that we saw Louisa do there? Share in the chat. I'd love to hear.

Yeah, Danielle says it was quantified. I agree. Good quantification, Louisa. We got some real numbers in there. That's good.

Kelly says you talked about the benefits. Yeah, agree. The benefits of the thing are very clear. I think that's excellent. Anybody else have something to share? I think those are the big ones for me. I really love that.

And I also can see Louisa, that you did a really good job, very confident cow face says Tanya. Very confident cow face. How could we forget?

But I also can tell what Allison's talking about right now that there's the soft benefits included. Satisfaction, morale.

You showed, Louisa, with this pitch, a really good understanding of all the different levers you could potentially pull to make this a yes. Which I think is great that you're sort of thinking through all of those.

Rebecca says knowledgeable about the broader picture. Exactly. Great. Okay, now what did we see here that we think Louisa could maybe improve on in her pitch the next time she does it?

Tracy says, um, ah, so, yeah. Okay, KLim says, too much background, not relevant to the CEO, little bit soft language. Rebecca said there was a lot of technical information.

Okay, Tanya said it could be more concise, agree. Danielle pointed out something really interesting here. Don't backpedal with, "I know it's a big change." So great catch.

I think Louisa put that in there specifically as bait for us because I was thinking, "Ooh, I love it." But one thing that I want you all to think about when you're practising pitching yourself, is if you ever hear yourself saying "but" in a pitch, that's a clue that you've gone in the wrong direction.

What Louisa did there is she goes, "I know it's a big change but." And then she started talking, as soon as you start hearing yourself do that, "Oh, okay." So yeah, agree. There was a little bit of that.

And I think Louisa, one of the things that I love most about the pitch, it's actually one of the things I hate most about the pitch. I mentioned earlier that you've got this good idea of the breadth of ways that you could convince them, but you were, I would say selling past the close, right?

You were piling on more and more benefits on top of what you had already said that was great, to be, "Oh, and it also does this and it also does this." It's a bit like watching an infomercial that's like, "It slices! It dices! It sorts your mail!" Right?

You don't need to keep going, you can just stop when you kind of hit them with the 20% and the 25K a year. I thought that part was really good. And I'd like that part to actually come even sooner.

You started with a little bit of background information. Part of that might have been for us as well, but I think you could tighten that part up where you say, "We're a small team, two people, we've been slowed down by the tool. We want to migrate to something that's more efficient."

I want to see that get a little bit tighter and just say, for example, "I've got a proposal that'll help our team of two, do more, faster. We'll be able to," I can't remember what the 20, what was the 20% about Louisa?

L - Reduce publishing time. Basically make us more efficient and be able to move faster.

H - Yeah, exactly. So you could say, "It'll help our small team do more, faster. We'll be able to reduce publishing time by 20% and save $25,000." I actually think you could stop your pitch there. They've got the info they need, right?

Then if they say, "Oh that sounds good," and then you can say, "Oh and also, I think it'll help us, you know, work with the engineers faster. I think it'll, you know, improve our ability to scale." Cool?

L - Yeah.

H - Louisa, you've been very brave. How was it to pitch in front of this room of people actually?

L - I mean, lots of friendly faces, it's totally fine.

H - Did you deliver the pitch as you expected to, or did you find as you went through that you started doing some of the things that we had just talked about?

L - I definitely started doing some of the things that we talked about and one of the things that you've said to me in the past, Holly, that always sticks with me, when I'm having these kinds of conversations is don't make arguments for the other side or don't negotiate for the other side.

I could hear myself doing that while I was giving this pitch. Like, "I know it's a lot of upfront investment." Some of the best advice you've given me is to just say the thing and then stop talking.

H - And then stop talking. It's really hard to do though, right?

L - Yes.

H - In the moment, you just want to keep justifying it. Yeah, and if you guys want to have a sport, go back and watch the recording later and then watch how often I've done that in this presentation alone. Even though I'm sitting here talking about doing it, I end up doing it from time to time.

We talked about taking out softening language and that's a way of softening the message, is by arguing for the other side. And I think if you do feel the need to soften it, which sometimes, it can be helpful to have like a spoonful of sugar to help the medicine go down, that's totally okay.

But I would recommend kind of disclaiming that upfront almost. And saying, "I've got a really good idea that's going to cost some money, but it's going to be worth it." Then share the pitch.

You kind of use it as an accusation audit at the beginning, which is the thing that, Chris Voss talks about where you sort of upfront name the thing that they might find objectionable and then that allows them to prepare themselves for something bad.

Usually, whatever they prepare themselves for is actually worse than what you come in with. It can help you come through that pitch better while still softening it at the beginning.

Whereas when you include it at the end, like Louisa did, or partway through the pitch, it sounds like you're backtracking on it, as opposed to sort of confidently identifying an issue up front.

It sounds like, "Oh, this is a bit vulnerable." If you all need to throw in some softeners, that's how I'd do it.

Summary: How to Pitch Checklist

All right, so your amazing pitch checklist that we talked about tonight is making it tailored, making sure that you're pitching it to the thing the person cares about and getting in the centre of the dartboard.

Doing the math like Louisa just did, like an absolute champ, so that the value is clear. Love that. Then making it as concise as possible. Nice and short.

We got Louisa's pitch from pretty long. I wrote my notes on two post-it notes down to maybe a single sentence or maybe two at most. Teeny tiny.

You should never be talking for more than four sentences in sort of that initial pitch phase, to make it nice and short. And then make sure that you are keeping it powerful with your language, your body language, and your tone of voice.

Get Help with Your Pitching Skills!

All right friends, if you want help with this, you can get coaching directly from me on any idea you want to pitch at work.

Book 30 minutes of my calendar at wimdi.com/book-a-time for free and we can chat about whatever pitches you have coming up, or whatever long-term project you have about making yourself be heard more at work in general, even if it's not one specific pitch.

And if you want to get really good at this across the board, another great avenue for you to do that is The Game Changing Year. A lot of what we talked about today is actually what we cover in The Game Changing Year.

We do pitching and we do it very similar to how we did it tonight. We have people like Louisa stand up, come up with an idea throughout the year, and then they stand up and pitch in front of the room and it’s critiqued just like you saw us do tonight with Louisa and all the other pieces that we teach in The Game Changing Year help you do this better.

We talk about uncovering business needs, which is just secret code for what the hell does the CEO want. We talk about understanding your value, which is just the way that you figure out how what you bring to the table matches with what the CEO wants.

We teach you how to do business cases, which is the math part of the whole thing. We give you frameworks for pitching beyond just what we talked about tonight, that'll help you do this really well, really concisely.

And then we also teach you how to negotiate, so that when the CEO says yes, you go, "Great, I'd like a new title with that and I'd like a team for that and I'd like, you know, to have an additional raise."

All of this is stuff you can learn in The Game Changing Year. If you're interested, you can find out more at thegamechangingyear.com or book some time in my calendar. All right, friends, thanks so much for coming.