How to strengthen your pitch to get to yes

Dear Sonya, 

I love that you are passionate about where you work and know that you’re looking to take on something that you can have some ownership over. And it sounds to me like you’re excited by seeing new opportunities that can make the company better. Taking the time to create a pitch for a project or new business will take it from an idea that you’ve casually thrown out in a meeting to a proposal for consideration that warrants a response.

To answer your questions, I spoke with Jennifer Brandel, CEO and cofounder of Hearken, a technology and consulting company that helps companies reach their audiences. Hearken started as a project that Jennifer pitched when she was working at WBEZ, the local public radio station in Chicago. As the project gained momentum, Jennifer saw an opportunity to grow the idea and eventually cocreated Hearken out of that work. Along the way, she did a lot of pitching. She shared a wealth of advice on how to frame your ideas and get heard. She is also the cofounder of Zebras Unite, a founder-led movement that reimagines funding and business structures for companies with social missions.

“Everything I have created is a result of some kind of a pitch, or more likely than not, multiple pitches of the same idea in different formats for different stakeholders,” Brandel told me. “So, I have a lot of experience.” 

Note: This conversation has been edited for clarity.

Work Space: How many times have you pitched Hearken? 

Jenn Brandel: Hundreds. I don’t have an exact amount but hundreds. The first time around I pitched Hearken probably about 70 times, and that doesn’t include all the different funders who might have been in a room for a demo day for a big pitch session. Many more people heard the pitch and did not come up to me afterward and say no. Just none of them came to me saying yes. And then, after Hearken was already successful and we had really cleared a lot of the early hurdles of a company—you know, finding product market fit, creating value, solving a problem—I still heard “no” on my second-round pitches to try to raise more funding. And I think that the second round, after I had established myself, it was 54 nos to one yes. And that yes came from an investor outside the United States.

How did you learn to pitch?

This has all been learning by doing. Trial by fire. I initially had to take drugs to pitch and was prescribed a beta-blocker to help with my heart rate because I got so nervous. I really started sweating and my heart was racing, and I was not able to think clearly. So probably the first 20 times I pitched, I actually had to drug myself to do it. It does not come naturally to me, and neither does public speaking—and pitching is a form of public speaking. Even if you’re in a room with one other person, you are presenting. You are on stage and in the spotlight. So it took a long time to get comfortable, and I still get nervous sometimes. What I try to remember is not to go with the power dynamic of, “I need something that this person can give me.” But more like, “I have something really exciting that I love and have been working on for forever and I’m giving this person an opportunity to join me in making it even better and more useful.” That change of mindset has made a huge difference.

What’s the best way for someone who is working within an organization to get buy-in from higher-ups on a new business opportunity?

I always go to the mission statement of the organization first. Start with the thing that a lot of people spent a lot of time wordsmithing and perfecting. The mission statement is what the organization believes their value is. So, connecting the pitch to the mission is one way to transcend—not always, but it can help—the personalities and blockers, the people saying, “That’s not what we do here.” You can jump above that dissent by saying, “This is what the organization purports to stand for and wants to do, right? This idea is an opportunity to either fix something that isn’t working well to achieve that mission, or to create something new that could really streamline or expedite your ability to meet that mission.” So I think that’s like a bit of an ace up the sleeve: paint a picture for how it connects to the mission.

What advice do you have for people who have good ideas but don’t think that they’re heard?

You might have thought you said something 100 times, but you might need to say it 200 times. There are definitely dynamics at play, especially with people who haven’t been heard—oftentimes women or BIPOC. I hate that this is the case, but you may need to say it more often than others and in more ways in order to have your idea be heard. But just know that most people need to hear something a few times in order to grasp it. If you’ve said something a few times and people haven’t acted on it, to me that’s a sign that maybe the way you frame the problem could be tested out in new ways. 

Once you’ve pitched something, if you get a nonanswer or a no, dig in and ask where your pitch needs to be strengthened. Understand if it’s not the right person, if it’s not the right time, or they don’t have bandwidth to think about it. You could then put this pitch in a different format that makes it easier to take to a boss. Because sometimes someone actually likes the idea but doesn’t have time to translate it into what they need to sell it up the chain. So, I think getting curious about the no, and not taking it personally, is really something that I had to work hard to do. I have had some good rage evenings post-pitching. You know from just being like, “You say you want this, I gave you this! WTF?” But at the end of the day, everyone’s human, and everyone is really stressed out, especially right now. So giving the folks you’re pitching a bit of grace and assuming good intent has never done me wrong. If you keep asking and they keep saying no, and you keep reframing it and they keep saying no, it might be time to move on. You might think the most important thing about pitching is how well you speak and persuade people, but it’s actually how well you listen. Because if you are not starting by understanding what the problems are that they’re trying to solve and if you don’t know where their energy and passion is and where their dissatisfaction is, you can’t effectively pitch.

How can people road test ideas before pitching them to the most important people?

Always start pitching to your friendlies first. Your friendly people could be, honestly, your dog or your cat or whatever animal you have nearby, stuffed or alive. And then also pitch to some friends or some people you trust, so you can get out your nerves and start to put language to the thing that might be very clear in your head, but you haven’t had the practice saying out loud. And if you can find people who are in a similar position but maybe at a different organization that you could pitch to, do that. Those people are likely going to have similar questions to what your boss or whoever you’re pitching to might have but they have no stake in it. They will only help you strengthen your pitch.

When you are pitching internally, how did you get your start with the project that ultimately became your business?

So, when I was initially pitching my idea within a newsroom, I didn’t actually go to the person who was in charge of the newsroom, I went to their boss. And it was a little bit of luck because they were just out of town and I had a deadline to meet for this pitch competition, so I needed someone to review it. But what I learned is that actually, that was the right move. The person at the very top has more license to take risks and be bold because they got into that position because they’ve been entrusted to have a vision and move something going forward. If I had pitched my boss—the person who I might have thought to pitch initially—that may not have worked because her job was to keep the system from breaking. And so, just by virtue of her position she has to be more conservative. So I ended up going to the person whose job it is to be bold and forward-thinking first—which, depending on your organization could get you in a little bit of trouble, so you need to be thoughtful about what that would mean—but there might be ways for you to float that idea to that person who is in charge of the vision in a way that’s not an official pitch. Maybe it’s a “Hey, do you want to go out for coffee?” Maybe you’ve heard them say that they’re looking for something, and you have an idea that might be useful. And you can even straight-up say, “I don’t want to send a 10-page proposal until we’ve had an opportunity to talk and I know it’ll be worth your time.” And then the boss can make the decision if they need to go and vet it with others below them, or they can sign off. So what I would recommend is to consider whose job in your organization it is to create vision and strategy and whose job it is to not rock the boat. Think about if your idea were to be successful, whose job it would make easier?

When is the best moment to pitch something that could rock the boat?

Change doesn’t happen unless there is sufficient dissatisfaction with the status quo. If you think about your own life, how difficult is it for you to make a change? Usually it’s forced upon us because what is currently happening just won’t work anymore. The best opportunity to make change is when you have heard—and other people have verified—that what’s currently happening isn’t working well enough. If you don’t hear the signal that people are dissatisfied, it’ll be a lot harder to get them to change because what they’re doing is working, and change is hard work—and we’re all exhausted. 

But one way to think about it is: Innovation is one of the major ways to attract talent. Companies can sometimes fail because they don’t attract talent. So when you’re pitching you can also focus on longer-term wins instead of the particular project you’re working on. Think about the positive benefits of what you’re creating down the line beyond the project, and consider putting that in your pitch too. If you feel like there’s any argument to be made there, make it. This can help if those you’re pitching to are fine with the status quo and have the bandwidth to think about something more aspirational that can leave a longer legacy. 

How do you get people to see your vision if they’re not dissatisfied—but you are?

One thing you can do is start to voice your own dissatisfaction with the status quo or your own idea for how what you’re doing now could be better. Create awareness of dissatisfaction in people with how it’s done now. Note: You can’t just say, “This thing sucks. We need to do something different.” People, at the end of the day, are going to throw up their hands and say, ‘Well then, what’s your idea?’” So when you’re bringing up the dissatisfaction, you need to come prepared with some kind of vision for how things can be different. How fleshed out that vision needs to be kind of depends on how formally you’re pitching. The more formally you’re making a pitch, the more you have to think through what objections people might have, and have answers to those objections before you pitch.

What’s your recipe for handling rejections?

In terms of rejection overall, I would say—I don’t know if I should use a sports metaphor, but like—no one hits a home run every time at bat. You know, it is impossible. So rejection and getting practice and pitching in, and having a no, I believe it just increases your chances of getting a yes at some point in time. So try not to get discouraged. 

What you’re doing is you’re exercising a muscle that is going to come in handy when you get that yes because then that’s where the real work starts. You are going to need to keep pitching your vision and the project to get more people on board to collaborate—to make something bigger than what you can do alone. So building that pitch muscle is imperative. More and more I’ve stopped taking rejections personally. In part because I’ve now been in the position as a boss where people bring me ideas, and I can’t say yes to everything, so I understand that it doesn’t necessarily mean the quality of the idea isn’t great or the person isn’t brilliant or it’s not something that should be done at some point in time. So to me, a no is not a rejection. It’s a signal that the conditions are not yet right for this thing to exist or move forward. I used to assume if there was a no, that was the end of the conversation. I didn’t realize no could mean, “Not right now,” or “No, I’m not the right person,” or “No, this doesn’t solve my immediate problem, and come back to me if you can figure out a way to make it solve my problem.” I just thought it was a complete sentence. In some contexts, “no” should be a complete sentence, but not in this case. 

So you’ve been told no but you don’t feel like that’s the end of it. What do you do next?

The no becomes your opportunity to ask questions and get a better understanding of what the no means. And try not to be annoying about it. It’s so easy to take it personally, and then if you come to the person who said no with some heat, they’re probably going to be more shut down than open to sharing what their thoughts are about why the answer was no. To whatever degree, tell them you would appreciate as much insight as you can about what their thought process was behind the no so that you can learn. You can ask them, “Is it not right now? Is it that you don’t think it’ll ever fly here? Is it too much money?” Even if that pitch never gets off the ground, you’ve learned why that was and be better equipped to make that pitch again, and even stronger, when conditions change.