Tips From The Top: One On One With Adriana Gascoigne

I spoke to Adriana Gascoigne, founder and CEO of Girls in Tech, about her journey and best advice

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Adam: Thanks again for taking the time to share your story and your advice. First things first, though, I am sure readers would love to learn more about you. What is something about you that would surprise people? 

Adriana: As a tech leader, you’d assume I’m all left-brain – analytical and science-focused. But if I had to pick which side is dominant, it’s my creativity and passion for all forms of art that win out. When I was younger, I was set on working professionally in the arts. I had a drafting table and airbrush gun, working on oil paintings and pastels, and later went to art schools. I was fortunate to have parents who cultivated my interests, investing time and effort into this creative outlet. Dabbling in various art forms led me to focus on fashion design, but at the 11th hour, I felt it was better to get a more general education. The decision was clearly the right one and I love working in tech. 

But I remain obsessed with art and design – and they actually serve as the motor that powers my career in tech. It energizes me to not just do what’s been done before, to challenge the norms, and to create my own organization. Girls in Tech wouldn’t exist if not for the artistic passion that spurs my commitment to erasing the gender gap in my industry (and beyond).

Adam: How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth? 

Adriana: My career started at a major consulting firm before I went to working at a dozen startups. As the only woman, I was subjected to so much unsavory conduct. In my first week at the first startup of my career, I received this incredibly graphic and descriptive email from a co-worker that was so wrong, so disrespectful, so explicit…I had to report it to HR and legal. Other than an empty apology and moving me to another part of the room, they did nothing. In fact, moving me isolated me, so it felt like I was the one punished.

The brogrammer culture was so prevalent that I just immediately accepted that as par for the course. But it wore on me. Eventually, I came to realize just how unhealthy these workplaces were for my own mental health, and for everyone else. Countless other women could recite the same stories nearly verbatim, and after a few years, it became clear that something needed to be done.

When I launched Girls in Tech in 2007 with 200 women attending a party in San Francisco, the choice to tackle such a monumental challenge was instantly affirmed. Listening to all the conversations, insights and brainstorming about what could be done – something which hadn’t been done outside of whispers outside the office – it was true proof of concept.

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level? 


  1. True passion for the work. It took a few years before I found that my true passion lay in social entrepreneurship, but I also still loved my career in tech. Merging my interests and work, and channeling it into Girls in Tech is the reason why the organization is thriving after nearly 15 years. You really have to feel that electricity — the drive to get out of bed in the morning and get to work. Your first leadership role may not be in the place that you really love, and that’s ok. But eventually you need to go out and create something that you love, or alternatively, really embrace what you have and own it. 
  1. Listen more, say less. Deep listening isn’t just waiting your turn to speak. A good leader understands the needs of employees as workers and people. Understanding where they come from, what concerns them, where their heads are at, and if they need a day off to reset after a bad day or week.

Listen. Do it exhaustively. And then, spend even more time listening. It’s all about empathetic leadership.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders? 

Adriana: Look for a moral compass in everyone you work with. Only hire people in whom you can spot it. A moral compass cannot be learned. If I see great potential, a great attitude, eagerness to learn and a firm moral compass, I always give the benefit of the doubt. These people can do anything with the right teaching. I never need to say “you don’t get it” or give up on them. Ever. That’s not how I work.

Lead with humility. Even in the C-Suite, you must be obsessed with learning every day and seeking new training. From developing strategy to communication with colleagues to business plans, the best practices are always changing and adapting. Humility helps in adopting new ideas and policies.

Always calculate risk. I worked at 12 different startups and love how lean and mean they were. In tech, we shoot for the moon — quite literally sometimes — but are very calculated in expenditures. Each risk or new idea must have a timeline and budget. If we’re not achieving x, y, or z goal by whatever deadline, we don’t equivocate. We pull the ripcord. Innovation and entrepreneurship require a bold mindset, while always calculating an endgame – even the bad ones. 

Adam: What is your best advice on building, leading and managing teams? 

Adriana: The biggest challenges in any leadership position involve the management of people. The actual work, strategic planning, execution – they’re essential – but take a backseat if you can’t properly create and foster a team. It starts with finding a way to trust each person’s individual intentions. Towards their job, their career, the company, their colleagues, their supervisors. It’s important to assess, both at the point of hire and continuously throughout their employment whether you have the right person in skills, background and culture fit. But I focus most of my attention on their intentions and passion for the cause/mission of the organization. 

You really need trust, which is particularly difficult in this age of misinformation. Finding talent is such an art and science, so you must give in and learn to trust upfront.

Adam: What is the single best piece of advice you have ever received? 

Adriana: No excuses. Ever.

In my second internship, I had an amazing boss at a firm called Moya, Villanueva & Associates. I was working on major brands like Nestle and Disney – a big deal when you’re starting out. When I told my boss I couldn’t get something done on time, she bluntly said “no excuses.” After initially being taken aback, I saw the wisdom in her approach to facing roadblocks by setting aside excuses and immediately offering three potential solutions for moving forward. Even though you might not have caused the problem, you always must be accountable. Don’t blame anyone. Apologize. But have a short-term memory and immediately pivot to solutions. 

No excuses. I take it to heart and my antenna goes up a little when people give me excuses. It reflects far better on a person to be focused on where we go from here instead of how we got to where we are.

Adam: What is one thing everyone should do to pay it forward?

Adriana: Mentorship. Every leader started out at the bottom, only moving our way up to the top with the support of mentors who took time out of their day to help us. Always say yes when someone new to the industry or company reaches out for advice. In a way, it’s paying it back since you got help first, but never forget that today’s intern is tomorrow’s CEO. One day you’ll find them to be leading the company that you’re trying to partner with, or they’re the decision-maker on a contract that you’re vying for. So, from a selfish standpoint, it’s just plain good for business. But more importantly, it’s a beautiful experience to watch a young worker mature into a leader, using the ideals and values that you helped shape. You know they’ll pass it along to the next crop of young workers too. It ensures that you, your organization and your industry are forces for good in the world. 

Adam: Is there anything else you would like to share? 

Adriana: Leadership sets the tone for an organization and change only happens when you have true dedication from the people in the boardroom. There are so many moving parts to diversity and inclusion – changing how companies source talent, continuous education of current employees, unwinding unconscious biases that impact product and service design – but leadership sets the tone. That’s why I launched an ambitious four-year campaign called Half the Board to demand gender parity in every tech boardroom by 2025. And it’s not just limited to tech, it’s a principle that should apply in every industry. The more diverse the board, the more likely the organization will have a great workplace for all. Until we see every board with a good balance of genders, races and religions, and with representation from differently-abled workers as well, we’ll never have workplaces that are truly fit for all workers. I encourage everyone who’s a leader, and everyone who aspires to be a leader one day, to make the pledge that they embrace the immediacy and actively work to make boardrooms representative of the workforce.

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