Crucial Questions The CEO of TaskRabbit Asks Herself In Order To Make Decisions

Ania Smith is the CEO of TaskRabbit, an online and mobile marketplace that matches freelance labor with local demand. She became CEO back in August of 2020, prior to that she held roles such as Director, Head of Courier Operations at Uber, Head of Operations, Host Services for Airbnb, and Director of Strategic Partnerships & Merchandising Strategy at Walmart--just to name a few.

One of the things that Ania says has helped her get to where she is now is her broad experiences living and working in four different continents. She has been able to work across many countries, cities, companies, and roles and that diverse background has taught her a lot. She has been able to meet new people, experience different cultures, and pick up new skills over the years.

Another way her unique background has helped is with figuring out what she wants to do in life. Ania says, “A lot of times, they'll say, you know, follow your passion. But that's really hard because oftentimes, we don't know what our passion is. So I'd like to think more about finding my passion. And really, the only way to do that, for those of us who are not lucky enough to know from when we're three what we want to be, is to try out many new things and see what really energizes you and motivates you and helps you think about the impact that you're having. And that has really helped me.”

The path to success doesn’t always have to be linear
As Ania shares, the path to her current role as CEO was not linear, it was very much a zig-zag. A lot of times we get stuck thinking that our next step has to be up the ladder to the next logical role--but oftentimes important steps in our career are side steps. As Ania shares, it is important to stay open to new opportunities to keep learning and growing and don’t limit yourself on where you have to go next.

There were definitely times in Ania’s career where she didn’t get the promotion she wanted right away, but there was always another opportunity waiting that allowed her to meet new people and learn new skills that she could take with her to the next role.

Ania shared an analogy her friend uses when thinking about the course of a career. She says, “A good friend of mine once used the analogy of a Google map. So she talks about how, you know, sometimes we're just like speeding down the highway towards our career and we know exactly what we're doing. Other times, we're on a slow country road. Other times we take the wrong turn. Other times, we actually are stuck in a traffic jam and really feel stuck in our careers. Other times, we may even have an accident and really have to pedal back. And I think that that's a sort of a great analogy to think about my career.”

Ania’s gap year
A couple of years after leaving Airbnb, Ania, her husband, and their kids took a gap year to go and live in Argentina. For a whole year, Ania and her husband stopped working and really took that time to be together as a family, explore a new culture, and talk about the future. She says it was an amazing experience to really step back from everything and to get away from the day-to-day race to really think about what she wanted her next step to be in her career.

When talking about the experience she says, “ I absolutely feel that if you can at all swing it, it is life-changing, it's transformative. And it really shows you that sometimes you kind of feel like oh my god, if I'm not at work, like the whole world is going to fall apart. And it's just unfortunately not true, for most of us. We're all capable of doing something else. We all change jobs very often. And this is this changing a job to something else before you change it into a new job. And to be able to take a breather and really reevaluate where you are and what you want to do and who you want to be when you grow up-- I ask that question to myself all the time, still today--and to have that space to think that through. It's amazing.”

While some people would be worried about leaving their career for a full year and getting left behind, Ania wasn’t too concerned. She knew she had been working for 20+ years and while she may be a little behind when getting back, she felt that she would still be relevant and would be able to catch up quickly.

And sure enough, one week after returning to the U.S. she had a role at Uber.

How Ania sets the vision for TaskRabbit
When she first started as CEO of TaskRabbit Ania made it a point to meet with every single employee inside of the company--she went on a listening tour, as she puts it. Instead of walking into a new company and laying out her vision for things, she knew it was important to find out what employees felt the current vision was as well as how things were going, what things were working, and what wasn’t.

Since then she has worked very hard with her leadership team to take everyone’s input in order to come up with a plan for where they want to be in 3-4 years and to define what the vision of the company is.

“And it's a pretty clear path for, not how we're gonna get there, but essentially what we will be in three to four years. And I think it's been inspiring for me as a leader, but also from my team and their teams to understand what we're trying to get to. And it helps, therefore, for us to help our strategy or sort of shorter term strategies forward, because we know where we're trying to get to, we just need to break it down and work backwards. It helps that process every year, as long as we have this sort of Northstar of what we're trying to get to.”

What does putting people first mean to Ania
One thing that Ania is very passionate about is putting people first. But what does that actually mean to her?

One of the key things for her is talking to people and truly listening to their feedback. She understands that it is crucial to learn what’s important to people, what do they value--and it’s different for everyone.

Over the course of the pandemic one thing Ania has discovered is important to her people is workplace flexibility and giving people options for where and when to work. And she’s really taken that feedback to heart. She and her team are offering flexibility now and they are also figuring out how to best address this need in the future.

“Feedback is a gift. So if anyone is willing to provide feedback, having the strength to accept the feedback--you may not agree with it--but having the strength to accept it, to think it through, to see how that may or may not help you, is really a big skill.”

How Ania makes tough choices
When she was younger Ania admits that when she had to make a decision she could not have enough data, she wanted to know everything before deciding. But over the years her approach has changed.

The truth is data can be used and manipulated in any way we want it to be. So relying solely on data is not the best option. Now Ania focuses more on her experience and gut feeling when making a decision, and if she makes a mistake she quickly fixes it and moves on.

“Over time, I realized that data has played lesser and lesser role in almost every decision that I make. And so much of it really just comes from, I don't know, that inner feeling that I guess people call it wisdom or experience or something where I feel like it's okay to go in direction A and I may be wrong, and often I am wrong. But it's better to make the decision quicker and to learn if I'm wrong than to continue to ask for more data and more analysis, and just kind of get stuck, and be unable to make a decision.”

You have to give yourself the freedom to make decisions, and you have to accept that you’re going to be wrong, but that’s okay. This is the way you learn and grow as a leader.