As a leader, you are expected to inspire your team, earn the trust of customers, and paint a vision for the future. All of these responsibilities require amplifying your leadership skills through powerful storytelling.
As a leader, you are expected to inspire your team, earn the trust of customers, and paint a vision for the future. All of these responsibilities require amplifying your leadership skills through powerful storytelling.
Storytelling is one of the most effective tools in a leader’s toolbox, but like any skill, it must be practiced and honed. To master storytelling, you must first identify the storytelling style that works best for you. You also need to know how to assess your audience and how to fine-tune your message so that it resonates. In a world of partisan noise and eroding trust, telling authentic stories is more important than ever, both for your company and for your career.
In this talk, you will receive tips from accomplished storytellers on how to craft and deliver powerful stories that will motivate your team members, endear you to customers, and strengthen your personal brand.
First, some basic Q&A on the topic of leadership through storytelling:
What is leadership storytelling?
As a leader, your job is to lead your team towards a shared vision. Storytelling is at the heart of effective leadership because it touches the hearts and minds of those who follow you. Stories forge meaning from the facts, creating examples that your followers can relate to. Stories are told and retold to cultivate a culture in your organization.
How do you tell an authentic leadership story?
Authentic stories draw from your own life, the experiences you have had and the choices you have made as a leader. Because these stories are personal to you, your authentic emotions can shine through when you tell these stories.
What are the elements of a great leadership story?
A great leadership story starts with a main character, usually you as the leader. In product stories, the main character can be the customer as well. The character experiences some tension takes action and the tension is resolved. The most common tension used for leadership stories is that of hardship that leads to personal growth.
How will storytelling help me influence my team?
Stories give meaning to the facts surrounding your team. It helps your team understand how to interpret the facts and spur action. For example, your team may be faced with declining revenue. Normally this is cause for alarm and should cause alarm if the company is losing business to the competition. But perhaps the overall market is undergoing an adjustment, and competing companies are also experiencing declining revenue that is expected to rebound. By understanding the meaning behind the facts and telling that story for your team, you can put the team’s anxiousness at ease and help them transition to action.
How is storytelling used in leadership?
Storytelling is at the heart of effective leadership because it touches the hearts and minds of those who follow you. Stories forge meaning from the facts. Stories are examples that your followers can relate to. Stories are told and retold to cultivate culture in your organization.
Keith Cowing comes from an engineering background and has spent his career as a product manager building products at companies like LinkedIn, Twitter, and FlatIron Health. He currently serves as CEO at Ruby, a mission-driven organization focused on supporting seniors living at home.
After leaving business school, Keith started a company, Seamless Receipts, where he jumped right in and learned how to sell on the job. Since then, he’s spent a lot of time on storytelling and saw the importance of how that fits into leadership.
Connie Kwan is a Storyteller and Product executive from Silicon Valley with over 17 years of Product Leadership Experience and a background in engineering. She led teams at Atlassian, shipped products at Microsoft, was the VP of Product at OMG Network, and CPO at a Khosla-funded startup. She brings a breadth of domain experiences to product challenges.
Currently, she is a fractional CPO and advisor on Product Strategy. She teaches Storytelling for Leaders to empower leaders to build their influence.
Keith Cowing: What inspired you to create your storytelling class for Leaders?
Connie Kwan: I was trained as an engineer, and at engineering school, they don’t teach you presentation or influence skills. As a product manager, those are the most important skills, so I had to learn them along the way by trial and error.
Three years ago, I met a person named Max who has a CS background but is also a full-time actor. So I was intrigued and took his presentation skills class on a whim. we spoke on the same wavelength and hit it off immediately. We didn’t meet for a while after that, but I kept his contact information. I could feel an idea between us waiting to be actualized.
Due to his background in on-stage storytelling, Max brought a very different perspective to business presentations. On stage, you ask yourself: How do you take a script and turn it into something that captures people? He taught me skills that were extremely useful for stage presence and connection with the audience.
When I wrapped up a Chief Product Officer position at a health tech company, I went into a creative phase. So I called up Max and we created a Storyteller system. And we help people understand one of six different storyteller types. By using the Storyteller system, students understand their default stories, and how other people have different default stories. So you end up having this gap where you're telling a story, but your audience needs a different story to resonate. And so when things aren’t connecting we sought out to help people understand how to tell their stories differently.
When I teach leadership through storytelling I want to help people adapt to their audience. I want to teach people how to leverage some of that in everyday storytelling whether it’s pitching to investors or teaching a child. How do you leverage some of those narratives that just really capture humans? It’s such an important skill because we're storytelling machines. That's what we do.
Keith Cowing: One of the things that I thought was interesting, chatting with you is hearing about how you described your engineering brain and then acting which is very different. How do you pull those two worlds together? We'd love to hear a little bit about how you can take storytelling from different aspects of life and bring it into your business life at work.
Connie Kwan: I work with a lot of CEOs. One of the challenges is that we've been taught to separate our personal life from our work. But we are a full person, and so the anecdotes and experiences you have, both professionally and personally, shape you and your story. So when people talk about authentic storytelling, storytelling isn't about creating something fake so that you can get someone to believe you. It's about finding what is true to you and authentic to you. And then bringing that story forward.
That is what will be more compelling when you talk to other people. That’s why in my classes I teach my students how to use those personal anecdotes. Those are the ones that are going to be authentic. And in fact, there’s a scientific aspect to it. If you're able to bring in an authentic experience that ties to what you're working on, then when you tell it, you'll be able to activate mirror neurons in the other person. Those mirror neurons will make them feel like they’ve actually stepped in your shoes and fully understand your experience. And that's what we're trying to tap into here. We want to tell a story that will connect with people and bring them on this journey with you.
Keith Cowing: There are two things within that I'd love to dig into a little bit and one is authenticity. One is bringing yourself out, not trying to play somebody else, but being who you are. And leaning into that. And then another one is thinking about the audience that you're telling a story to.
Connie Kwan: So on the authenticity side, you know, I'll share a story from my own experience doing leadership through storytelling. When I was the founder and CEO for the first time, I was going and making presentations at a lot of conferences, and I was learning how to be a storyteller and how to be a leader and how to project confidence and do all these things. I had this image in my head of what a sort of powerful, successful CEO looked like. And I remember going to a conference. And I noticed that sometimes I'd introduce myself, and people wouldn't hear my name. And I'd have to say it again and say it louder. And I was trying to picture this powerful executive who projected their voice everywhere. And I was like, I'm not playing that role right, I need to do this better and stronger. And I was there with my co-founder Ilya and when we were there, I thought I introduced myself strongly and effectively to this woman after a talk that I gave. And afterward, Ilya came up to me and he's like, Keith, why did you just yell at that woman. And I realized I was just so overcompensating, trying to play this role that I pictured myself needing to be and it wasn’t working. So over time, what I found to work best was not leaning into being somebody else, or playing that role, but bringing myself out. In the end, that was what led to a natural passion and natural authenticity. And then I could own a room and I can have the energy and the eloquent description of an event in a way that was just way more powerful than when I was trying to do something else.
Keith Cowing: And I'd love to hear you talk a little bit about that authenticity and how folks that are in the audience can think about that in their personal lives of any kind of tactics or recommendations that you have for them to think about how to bring their storytelling type out.
Connie Kwan: Yeah, for sure. If you haven't found it yet, go take this quiz to find which storyteller type you are. And then from there, you can either choose between two paths. You can either lean into that type and just really make that you.
For example, some people are most effective at convincing people over coffee. Whereas others, like myself, like to be on stage. I'm a visionary type so that's my natural place. That doesn't mean I can't be convincing in the coffee shop. And it doesn't mean someone who prefers a coffee shop can't be convincing on stage. But it just means that's your default, that's where you're comfortable.
Once you know that, you can learn how to find yourself in other environments. You have a comfort zone. And you practice that a lot, because you show up in the coffee shop a lot, and so you get good at that style. But it doesn't mean you're not good on stage, too. So then you practice being on stage and practice the energy, the style, the body language, and the voice.
It’s a little bit like singing in that people have a comfortable range. However, you can stretch your voice to be higher or lower. But mostly, you like to sing in the middle range, right. And so most of us live our life speaking in the middle range, never singing the high and low notes. However, once you practice those high and low notes, they can become a part of your comfortable range.
Now you're comfortable in both. It's all about practice and staying authentic. When you practice a lot, you'll stay authentic, because that is part of you. You just have a lot of options and a lot of capabilities that you're not yet aware of.
Keith Cowing: So we've got several great questions coming in. How do you work with people in your coaching, how to structure their story, thinking about the beginning, the middle of the end, when you're doing storytelling? And then also how to control the length? How long should it be?
Connie Kwan: Every story has a character, an event, some kind of tension that happens, and then some kind of resolution. And you have to introduce each of those things. I think the key is just breaking everything down into that basic story structure. It’ll make what seems like complex storytelling so much easier. And you’ll find, you can do that for just about everything. And once you get really good, you can do that in very little time with very little information.
So speaking of length. Let me give you an example of a great story that is 4 words.
Baby shoes, never worn.
That's the story. The great thing about that is that it’s nuanced, but it gives you every aspect of the story- the character, event, tension, and resolution, without spelling it out. Your brain filled it in. And it was probably more powerful that way. From those four words, you know some parent (character) had a child (event), they were never worn (tension), and you come to the tragic resolution of why that is.
Once you master storytelling, you can have a story and blow it out into long-form, and then just take the essence and turn it into something that you can communicate in 10 seconds. And you don’t have to highlight every detail because your audience’s brain will fill it in. You just need the four storytelling aspects, and you can create a story of your desired length depending on your situation.
Keith Cowing: What questions do you ask yourself when you're trying to prepare for different audiences, for example, if you're presenting to middle management at your company, versus if you're presenting to the C suite, maybe it's the same story, but naturally, you're gonna have to adjust it a little bit for it to resonate at different levels of the org.
Connie Kwan: Your story is complicated. The longer you're in your company, the longer the essay is about the product that you want to write about. So first create this map of all the pieces you can talk about. And then overlay that with what the audience cares about.
So for executive teams, they care about broad strokes. The questions they want to be answered are where are we headed? What are the risks? How do we get there? And what is the benefit of getting there?
So you need to make sure you hit those high points from a data perspective, and then weave that into a story. Make sure everybody in the audience has something going for them as you go into your story so that they remain engaged. So with executive teams, I try to keep it brief and focus on the questions they need to be answered.
If you’re talking to middle management, they care about something else. They care about the processes. They may be thinking about the team overall. How do they motivate the development team? How can they maintain the code quality? In short, they don't want to ship bad stuff. They care about their reputations and they want to make sure that whatever they put out is good.
They're creators, so I step in their shoes, and I understand what they care about. And then when I craft a story, I pull out the pieces that relate to the vision, the process, and the tradeoffs. , And I push those things to the forefront. How do we come together and build this so that it meets the quality you are that you desire?
Every team has different things that speak to them. Once you can identify that, you can create a story around that, and then really resonate with your audience.
Keith Cowing: The best leaders connect with people. And part of that is understanding your audience and adjusting the story. How do you not only tell the story but how do you personally connect with them? So the story resonates, and they trust you?
Connie Kwan: There's the classic way, which is just building a relationship. So getting the coffee, going for walks, right, building that relationship. It will also be the most rewarding because now you have a better understanding of what they care about.
That way when you get into the room, now you can naturally address them and their cares. I think that's the most important.
If you don't already have a relationship, then do some digging. Say it's an investor who you want to pitch. You can get that perspective by looking at their website and understanding what they care about. You want to speak to what they care about. And then you can use the storytelling techniques effectively by creating that tension before you give them that resolution.
Keith Cowing: It sounds like a big part of what you're describing is empathy. And it comes in very different forms. But I've seen that people frequently during their career, maybe start from an inside out perspective of here's what I have to say, I'm going to project it onto the world. And if you're giving a presentation, the first question is, okay, what should I say? What should my slides be? And then over time, I think a lot of the best leaders flip that more of an outside-in approach of thinking first about what the customer is feeling? And then saying, what do people want to hear?
Connie Kwan: And you're putting up a great point, which is, we're given two ears and one mouth for a reason. Listen twice as much as you speak. And that's true. We say leadership through storytelling, but 80% of the work is listening ahead of time. So that when you do open your mouth 20% of the time, something valuable comes out.
Keith Cowing: How do you work with people on that front? Especially as we're doing a lot of things over Zoom- how do you think about listening?
Connie Kwan: Listening can be tricky. It takes more energy to listen than to speak. Because you're listening for the verbal content, the word choice, and sentences, the meaning. Sometimes there are double entendres like, what is said is not what is meant. And then there's the whole context that will bring it together. But with zoom, you’re kind of left with a lot fewer clues.
If you're in a coffee shop together, you can read their body language and their facials a lot better. With zoom, it’s a lot harder to get a read on them. And that is even worse when communicating through email or Slack. And the problem is 70% of our communication is the unspoken part. How we say things, not what we say. So we're losing 70% of that communication, which is tough. You got to make that up somehow. And the answer is simple. You fill in the context yourself by asking clarifying questions. And don’t be afraid to do that because assuming their meaning will probably lead you astray.
And one listening technique that I recommend when I work with people is for example, in user interview sessions, I often recommend having two people go in. Have both people take notes and share them afterward. And not only do you have double the people recording the information, more often than not, you’ll also find that you heard different things. It shows how our perception shapes our listening, and comparing those notes afterward will bring you closer to the most accurate version of the meeting.
Keith Cowing: We're in a moment where trust and credibility are really hard to come by and are maybe more important than ever. And so how do you think about building trust and credibility?
Connie Kwan: Trust is the foundation of your storytelling. So one thing is committing to authentic storytelling as we were talking about before. Another aspect is the first impression. A lot of that trust gets committed when you first meet somebody. That's why they say first impressions are really hard to overcome.
So as much as the content of what you say matters, the way you approach that person in the beginning, matters even more. It's all about being mindful of how you approach somebody, whether in person or Zoom. I think a lot of people overthink what they say, but I think it’s important to remember when you meet somebody, to pay attention to the person themselves. That day one trust is all about initial judgment. Are you treating them like a person? Or a business prospect.
And then obviously, over time, whatever you promise, make sure you deliver to build long-term trust. And of course, you know, over time you build a relationship with that person through this type of trust.
Do you want to unlock the power of storytelling in life and leadership? Take this quiz to find out which of the 6 Storyteller Types you are. And if you’re ready to invest in yourself, sign up for the Storytelling class for Leaders.
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It didn’t used to worry like this.
I remember that in my 20s I was much more carefree.
“Culture eats strategy for breakfast.” – Peter Drucker
In 1997, Steve Jobs rejoined Apple when the company was 90 days away from bankruptcy and spent a whopping $90M on the “Think Different” campaign that displays no products whatsoever.
An outsider might call this an insane move.
But the late visionary knew that humans thrive on stories. These stories create a robust company culture, which serves as the fertile ground where a strategy truly bears fruit.
Accordingly, as much as the campaign was aimed to revive Apple’s brand, it was about making the folks at Apple see themselves as the protagonists set out to save something worth saving.
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