Upasna Gautam on speaking to help others

As part of our #WTDSpeakerStories, we spoke with Upasna Gautam about how she speaks (and writes) to help others solve problems. She discussed her desire to fight for more diverse representation in the speaking and tech communities, as well as her first experiences as a speaker and her process for developing talks.

In our Women Talk Design Speaker Stories series, we’re interviewing Women Talk Design speakers about their journeys and experiences. We talk to speakers who are just getting started, speakers who have had their fair share of speaking mishaps, speakers writing books, and speakers curating events. At the end, we offer an opportunity for folks from the WTD community to ask their own questions and connect with each other. Visit our events page for more information about the series and RSVP for our next event.

On the left, a headshot of a woman with dark hair wearing a black leather jacket and jeans is seated looking into the camera with her hands folded on her knees. On the right, "Women Talk Design Speaker Stories featuring Upasna Gautam" written in black on a beige background.

Upasna Gautam has been public and keynote speaking for the last decade, and is a regular speaker at conferences like SXSW, INBOUND, Grace Hopper Celebration, the Digital Summit series, and TEDx.

In Upasna’s role as Product Manager on the Digital News Platforms & Services team at CNN, she works with CNN’s engineers, designers, editors, and journalists to develop and optimize the content management technology that delivers breaking news to the world. Upasna has been working in the tech industry for the last 15 years, where she has been an integral part of delivering technical, data-informed solutions for brands such as Ford Motor Company, PCMag, Mashable, Mars Corporation, and Kimberly-Clark.

Outside of her day job at CNN, Upasna is an avid public speaker, writer, tech career coach, meditation teacher, Community Lead with Google’s Women Techmakers, and a Product Management mentor with the News Product Alliance. In 2022, Upasna was awarded a Top Product Coach honor by Reforge, Products by Women, and Scale Higher.

Upasna’s publishes a monthly LinkedIn Newsletter about mindful productivity and leadership called “Working from Aum.” You can subscribe to it here.

On how she started speaking

Upasna started by telling us how she started in public speaking. While she began with some unpleasant experiences, she eventually found her way back to it.

“It didn’t really start from a positive experience. It stemmed from some crappy experiences that turned into really good experiences.

When I first started working in tech, I had some managers and bosses at the time who told me that public speaking is a great way to build your professional brand and solidify those skills in the workplace. So, I was very interested in figuring out how to go down that path.

The problem was when I expressed my interest in learning more–how do I pitch, could you review this proposal for me, or could you recommend me for this conference I’m interested in–I got shut down by those same people over and over and over again.

[I was] shut down, ignored, sometimes gaslit about things in the process. It wasn’t until a few years later, when I had new bosses and mentors, that [they] actually became my sponsors and advocated for me.

The really crappy part about all of this [is that] the initial experiences in the beginning of my career–where I was ghosted and ignored or gaslit–those experiences happen to be with leaders who are women. The ones who gave me the opportunities later on, were actually men.

I didn’t realize this until much later in my career what had happened there. When I did, I made a vow to myself to never be that woman in my career, especially as I became a leader.”

When talking about the beginning of her speaking career, Upasna highlights the support of others as a key part. 

“Going back to those experiences when I expressed my interest, having a sponsor was really the critical part.

Not just a mentor that can show you the ropes, but really having someone as a sponsor who can say your name and recommend you and tell you, ‘This is the way in and I’ll recommend you for this.’ Or, ‘I’m gonna connect you with this person who is the conference organizer.’ That’s what they did for me.

It started with very, very small meetups. My very first speaking engagement was a little tech meetup that I was invited to speak at because my boss recommended me to the organizer as a way to get my feet wet. It was a group of 50 people. I was terrified and excited, and that one event, that one speaking engagement bolstered everything else after that. After that, [opportunities] came trickling in one by one by one, because it’s kind of a domino effect.

If you get to know the people and you do a good job, they recommend you to others. And also at that point I had a great network at work that was recommending me for different events.”

On her first speaking experience

Upasna described the first talk she gave to a small meetup and how that experience showed her what she enjoyed about speaking.

“The topic I spoke on was search architecture because I was working on building (or re-architecting) the way search and data is architected digitally. So very, very, very dry, very black and white, very technical. The Meetup group was that audience so it was a good fit.

There were a lot more people than I expected–I thought it was going to be 20 and it ended up being like 50. And, it was in a classroom type setting.

I was a nervous wreck. I don’t really remember the actual presentation–it kind of went by in blur and I blacked out a little bit during it. But, at the end, I started to feel a lot better when people started asking questions. 

That’s usually my favorite part of my presentation–the end, when people ask questions. The types of questions people were asking validated to me that I didn’t mess up, I knew what I was talking about, and they wanted to know more.

And, to me that is the sign of a job well-done.”

On the topics she’s speaking on

Upasna also went over the topics she’s speaking about now and how different they are from the talks she used to give.

“It’s so interesting how much it’s changed.

I started talking mostly about technical topics related to the problems I was solving at work. [They were] very rooted in the technical architecture of things I was delivering and discipline related.

Now, I talk a lot about leadership, public speaking, and communication because I realized that the hard skills and technical skills are much easier to pick up and learn. The essential skills (I stopped calling them soft skills) are much more difficult to pick up. You can’t just read a book and learn how to be a great public speaker. You can’t pick up a book and learn how to be a great communicator or a great leader.

I talk more about that now, especially because I never saw women like me–of different colors, shapes, and sizes–talk about these things when I was growing up. When I was in the tech circuit 10 years ago, it was much worse than it is now. There was just a tiny fraction of women speaking in those circuits.

This lack of representation is still there and this is why I keep pushing to have those conversations and be in those places, to give those talks.

Also, I have found that there are these two groups or two camps of presenter types and content that’s delivered at conferences. There’s one group that is very much the inspirational, motivational speaker. I am not that. I prefer to focus on tactical guidance–when you walk away from investing an hour of your time with me, you have very tactical, actionable next steps that you can take. And usually the byproduct of that is that people are inspired but that’s never my primary goal. 

I realized that that was also sorely lacking in the content that was being delivered in presentations. It’s a lot of flowers and butterflies, which is nice to hear sometimes, but [when] people spend a lot of money to go to conferences or invest their time and energy, I wanted to make sure that I’m always delivering tactical, actionable guidance.”

When it comes to deciding on a topic and researching it, Upasna said she focuses on where she can provide value and solve a problem. Her main advice: follow your passion and don’t overcomplicate it.

“If there’s a lot of ambiguity and subjectiveness around leadership, communication skills, and public speaking, my goal is always to try to create and share frameworks or ways of thinking so that when you walk away you have a clear next step, no matter where you are on your path.

Sometimes in pursuing a path like public speaking, so much is over-complicated. Just talk about the stuff you’re passionate about. That is the most important part. If you are doing it because you think people want to hear about it, and not because you’re actually interested in it, it’s not gonna work. I’ve been there, done that.”

Upasna also talked about the importance of bringing yourself into your talks. She suggests that you use your curiosity (or frustration) to guide you to a topic. And, to be vulnerable.

“I’ll never forget my first big conference. I had one of my peers and friends in the audience. He was there to cheer me on and give me feedback afterwards, and I was just happy to have a familiar face in this very big room. After my presentation, I asked him what he thought. And he said, “It was great. You know your stuff, there’s no doubt about it. But where were you?” And I never forgot that. He said, “I know you outside of this capacity, and you were not there. I didn’t actually see Upasna there. I saw a smart girl talking about some stuff but the personality I know that makes you who you are was not there. And that could have made it a 100 times better.”

When it comes to those topics that you choose or want to talk about, just go with what makes you excited or what makes you curious. Where are the places your mind goes when you’re like, “Why is this the way it is? Why does this problem exist? How come no one has thought about solving this problem this way?” Let your emotions guide you. When do you get really pissed off? When do you get really frustrated at work? 

Another one that always works is when you’re able to be vulnerable and share a mistake you made and how you navigated that experience or how you overcame a roadblock. It could be a literal, technical roadblock, or dealing with a difficult coworker. Use your experiences to drive what you want to talk about.”

On how she develops talks

Upasna shared the formula she uses to develop her talks, focusing on three key parts.

“A lot [has changed] over the last few years. But there’s one thing that has not changed at all. 

If you follow me on social media or you’ve been to any of my workshops on public speaking, I have shared this formula that I used over and over and over again. It works every single time, no matter where I’m speaking. I always start with this 3 part formula which is creating a title, a summary/abstract, and my actionable key takeaways. 

It’s like my outline for my entire talk but I also used to use that to pitch to different conferences. Those three elements of that proposal template are the three most common requirements that every single conference organizer wants or that you’ll see in a call for proposals or speakers. After being rejected and accepted so much in my first 5 or 6 years of public speaking, I realize that these three elements are always there.

You have your title–your title is your title. [The] summary or abstract like the value proposition of your talk. A lot of conference organizers use that piece to put in their agenda and that’s what the attendees see so I’m always writing that with the attendees in mind. 

Then there are key takeaways. This is a big, important piece that I think a lot of aspiring public speakers sometimes miss–what are the tactical takeaways that the attendee is going to walk away with? It’s literally a bulleted list of, “The attendee will walk away with 1, 2, 3 after my session.” It’s very, very specific–specificity is really key in all of this. It’s much better to pitch something or talk about something that you deep dive into rather than touch generically on several different subjects.”

Once she’s develops a talk, Upasna practices it. She walked through her process for practicing and how it looks different than when she first started speaking.

“As far as practicing goes, it’s very different depending on the type of conference and the type of event.

At the beginning. It was a lot of practicing with peers [and] doing trial runs. I learned really quickly that that stressed me out, and that didn’t help me deliver my best presentations. So I started to record myself and I started to just do [my talks] alone and speak out loud. That actually helped me the best.

You really have to figure out what works for you.

I know when I’m ready for feedback and when I’m not. I was asking for feedback too soon and I wasn’t ready to receive it because I needed to just get [the ideas] out and articulate what I wanted to present and refine it myself until it got to a point where I was ready to have a peer review of some sort.

When I’m practicing, I scan through my slides to make sure I have a firm understanding of the sequence. I actually try not to over-rehearse because I don’t want to sound robotic. Within that same vein, I try to keep my slides very sparse with words–bullet points, some key takeaways, more imagery. 

The way they look has transformed dramatically. That just happens with experience, and as you build confidence and comfort.”

On how she uses social media

When we asked about Upasna’s social media presence, she shared the motivation behind the way she’s using those platforms and how they’ve supported her speaking.

“After not hearing [that I have a large following] for a while, I’ve had several people say this to me in the last couple of months. It’s kind of funny because I have no strategy. I think of stuff on the fly and then I go and share it because I’m inspired in the moment or maybe I had a conversation with someone.

I just throw everything out there and see what sticks in the hopes that it will help someone.

I will say that I’m glad that stuff like this is resonating more on social media. When I joined Instagram when I was 22, I never would have imagined that I would be sharing content like this. I was sharing pictures of my drink at the bar at that time–please don’t go scroll back on my Instagram.

I only started to take it really seriously–as far as sharing more stuff around professional development–during the pandemic. One, out of boredom. Two, out of like a way to pay it forward and give back in a really low effort, high impact way. 

I’m always about efficiency. It’s a really easy way to just get out there and share things that you love or that you’re passionate about.

I look at all these mistakes I’ve made and things I’ve learned in my twenties and early thirties. These are things I wish that I had known at that time. That’s really where all of it comes from

I always feel really grateful and indebted to a lot of those mentors and sponsors that I had at any point in my journey. They would always tell me, “You will pay it forward when the time comes too.”

I go into it all like I mentioned–how can I help other people solve problems? That is really what a great public speaker does–you help the attendee solve a problem that they are facing in their life. I’m a product manager so I try to come into every presentation with that mindset. I’m here to help. How can I help you navigate a roadblock, or solve a problem? Is there an obstacle that we’re all facing, or that I’ve faced before?

The opportunities that have come from the type of content that I’ve shared are [from] people reaching out directly. 

It’s also caused a major shift for the better in the way that I approach speaking opportunities or take them and assess them as well. Before, I was reaching out. The tables have definitely turned where I actually don’t pitch anymore and I have gotten an influx of requests because of that type of content being shared.”

On her advice for new speakers

Upasna shared some of her key advice for new speakers: nail your proposals. 

“To be a public speaker, you need to get accepted to speak at conferences. That’s the goal. In order to do that, you have to have really compelling and strong proposals that you’re pitching.

And so this goes back to what I always preach like a broken record: have that three-part proposal nailed down. That is the first thing that the organizers are going to see and what they’re going to base their decision off of. 

You don’t need to try to be clever and creative. You need to be specific and clear. When I read the title, I should know exactly what it is that you’re delivering. 

For example, my public speaking workshop. I used to call it How to Break into the Public Speaking Circuit as a Woman in Tech. This past year, when I redid it and delivered it again, I changed it to How to Pitch Winning Speaking Proposals. 

You want to be able to get your point across really quickly and clearly in that title. That’s part one.

Part 2 is the summary, which is 3 to 5 sentences. This is also known as an abstract. This is your talk’s value proposition. Why are you the person to give this talk? Why is it an important topic to deliver? What value are you delivering to the audience?

Then, the part that most people miss–the key takeaways, which are the tactical learning objectives. Think of them as action items that the audience will walk away with after they listen to your talk.

Those three parts, you have to start there.”

She also talked about the advice she’s received over the years.

“The best advice I have received I have distilled down to this: A lot of times, people think that they need to reach a certain level of expertise or a certain point in their career to be a public speaker–you need to have a specific title and be a leader to be a public speaker.

You don’t have to wait until you reach the top to be a leader. You can be a leader doing anything you’re doing right now. You don’t need to be a Barack Obama level orator to be a great public speaker.

Anyone can do it. You just have to be passionate about helping other people solve problems.”

For more on how she evaluates speaking opportunities, her thoughts on balancing her career with speaking and creating content, and her experience with TEDx, check out the full video below.

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