“Be thoughtful,” Samantha Jacobson from The Trade DeskDec 7, 2022
Meet Samantha Jacobson, Chief Strategy Officer at The Trade Desk. Samantha has an impressive resume and years of experience leading teams with grace and empathy. But she didn’t get to the top overnight. As she advanced in her career, she learned some valuable lessons that have helped her grow into the powerful woman she is today.
We asked Samantha to think about the defining moments in her career as well as the wisdom she’s learned along the way. Plug in below to hear her wonderful anecdotes and advice!
Focus on what you can control.
“One small anecdote that comes to mind is about ten years ago, I was working at a smaller-sized tech company. And we had a meeting invite on the calendar with one of our partner organizations. I was preparing [for] what was going to be a really difficult conversation to have with the partner. I typed up a bunch of notes internally and, unintentionally, I appended those notes to the calendar invite, which also included the partner. I immediately reached out to my boss at the time to let her know about my error, and she went into problem-solve mode. We reached out to the CTO as well as the head of IT to figure out if there was any way to unsend it. Unfortunately, there wasn't.
I felt so terrible about what had happened, and her response was, ‘It's okay. Let's see how Thursday goes.’ That's something that I will carry with me forever. Because it was a moment in time where I'd made an honest mistake, and I felt horrible about it. But her reaction was so helpful. She reacted so rationally and focused on what can we do to fix it? Outside of that, it's out of our control.
She gave me so much grace in that moment. That's something that I really try to carry forward with me when I'm interacting with folks in different situations, to really focus on what can I control or what can they control, and how can I make sure that it's a positive teaching moment. Because to me, those are the real learning opportunities when we think about how we can improve going forward.” – Samantha Jacobson
Ask inquisitive questions.
“One other example that came to mind in terms of a really negative experience that I've tried to turn into a more positive area of focus for me going forward, was actually when I was applying for business school. Part of the application process included an interview with either an alum or someone from the admissions committee. As you can imagine, I was really nervous going into the interview. We sat down, and the first question she asked me was, ‘Can you give me an example of a time where you experienced challenge or adversity?’ Then she looked down at my resume and said, ‘But looking at this resume in front of me, you've clearly lived a very charmed life, so this one may be hard for you to answer.’
I was so taken aback in the moment. For her to make this assumption that because she could look at one piece of paper and have a sense of what my life was, was really off-putting. Not only was it really uncomfortable, but it made it really challenging to create a connection with her for the duration of the conversation.
I try to carry that with me as I interact with people both personally and professionally, to recognize that while we may be having a conversation about one topic, I'm fully aware that there may be more going on in their life outside of work, and I may not be aware of what's on their mind at that point in time. Just trying to come to those conversations with grace and leniency, and to ask inquisitive questions rather than assuming that I'm aware of what their perspective is has been something that I've tried to bring forward in all aspects of my life.” – Samantha Jacobson
Be thoughtful in your interactions.
“A lot of times, when I'll listen to different leaders speak about how they were successful in their career, they'll talk a lot about mentorship. A couple of years ago, I had a woman reach out to me. She sent me an email saying, ‘I'd really like for you to be my mentor.’ I said, ‘Absolutely happy to see how I can best support you.’
She set up a half an hour, and I hopped on the phone. She said, ‘Great, I'd like for you to be my mentor, and I'd like to meet once a month for 30 minutes.’ I said, ‘Okay, I'm open to that. What would you like to discuss? Are you looking to talk about your role?’ Her response was, ‘Nope, I've been told I need a mentor, and I like your career trajectory. And so, I want you to be my mentor.’ As you can imagine, it didn't get more productive from that point forward, nor did we have a close relationship because she looked at it as very transactional and something she wanted on a checklist.
The piece that jumped out to me was how important it is to be thoughtful in the interactions I have with people, especially when I'm asking for their time, but to also be aware of what I'm hoping to get out of that situation, or what success looks like for me, so that I can construct the time to reflect that as effectively as possible instead of treating it like a checklist item.“ – Samantha Jacobson
People remember how you make them feel.
“Something I've really learned is that people rarely remember what you say, but they always remember how you made them feel. And that's something that I think is important to keep in mind in all interactions. Recently, for example, I was talking with a team member about how I needed them to do something differently or they had missed a deadline.
Later on, I asked another colleague for feedback on how I had handled the situation or what I could have done to be more effective. He gave me the really helpful advice that rather than framing the conversation as, ‘You need to do X, or Y didn't work,’ I would have been more effective if I had framed it as, ‘I need your help doing the following.’ Because people love to help, and they want to do their best. But I think coming to each conversation, whether it's a constructive conversation or whether it's a really positive one, to make sure that I'm aware of how each participant leaves the conversation feeling as a result of the dialog that we've had.” – Samantha Jacobson
Observe how people interact.
“I've learned the importance of relationships and observing how people interact in terms of what's effective versus not. This comes to mind because frequently earlier on in my career when I would sit in really important meetings, I was so focused on what I wanted to convey, or what my perspective was to what someone had said, that I would sometimes lose track of listening and focus more on that.
What I found is that frequently sitting back and watching the dynamics in the room unfold, usually the person that is most influential is not necessarily the most senior. It has to do with how they present, or what works well for the level of depth in that room. To me, watching the different personalities ebb and flow and to focus on what made someone really effective when they made their point has been really helpful.” – Samantha Jacobson
Check in with yourself.
“I've been in situations where I felt like I was trying my best, but the outcome wasn't what I had hoped for. Something that I find very grounding is to continually check in to figure out how I'm feeling about the situation, but to also make sure that I have outlets outside of my job. For me personally, I kind of bucket them into my husband and how our relationship is, my kids, myself (making sure that I'm giving myself time for walking, or reading, or whatever my version of self-care is), and then my community and volunteering.
I try to take a step back and check in on how I'm doing with each of them. Because a lot of those things in terms of ‘you can have it all, but not at the same time’ haven't really resonated with me because I don't want to think of my life as being sequenced. But I do find that taking a step back to understand how I feel like I'm showing up in each of those areas, and what's working or not working, has helped me create balance. It's also helped me put into perspective, to think about how I am doing on the whole, as opposed to in just one silo, and defining myself by that particular area.” – Samantha Jacobson
Samantha left a lasting impression with us! How about you? Craving even more actionable advice from female leaders? Check out more Pass the Mic content.
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