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Thinking About a Big Career Change? Ask Yourself These Questions. Kristi Knaack Riordan, COO of coding educator Flatiron School, shares what it takes to thrive in times of upheaval.

By Nina Zipkin

entrepreneur daily
Courtesy of Kristi Knaack Riordan

In this series, Open Every Door, Entrepreneur staff writer Nina Zipkin shares her conversations with leaders about understanding what you have to offer, navigating the obstacles that will block your path, identifying opportunity and creating it for yourself and for others.

It can be difficult to make a big change. But while circumstances can sometimes be out of your control, what you can have is mastery over the skills and the confidence you bring to the table. Kristi Knaack Riordan says that both of these things can be taught.

Knaack Riordan is the COO of the Flatiron School, a company dedicated to teaching people to code to help them launch new careers as software engineers, while also developing a community of peers to help them succeed.

"One of the things that is really special about Flatiron School is our mission statement: helping people transform their lives through education," Knaack Riordan tells Entrepreneur. "That's a pretty powerful thing."

Related: Want to Achieve Big Goals? The First Step Is to Get Comfortable With Failure.

In the world of STEM, that opportunity can be tough to come by, especially for women pursuing these careers. According to data assembled by LinkedIn in 2013, representation of women in software engineering roles on average struggles to hit 30 percent.

But this is a gap that the team at Flatiron School is cognizant of and working to bridge. The school has seen 1,200 graduates, with classes that have ranged from 35 percent to 60 percent women. Not only that, but 48 percent of the school's employees are women, and 55 percent of department heads are female.

Read on for more insights from Knaack Riordan about the difference between transparency and trust, how to own your leadership style and how to go after opportunities with passion and conviction.

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What are your responsibilities as COO of Flatiron School?

I spend an enormous amount of time thinking about communicating our strategy and making sure that people understand it and feel connected to it. I move information across the organization and I close a lot of gaps. I also get to spend a lot of solving problems.

From a more specific basis, I oversee education. For us, that is the operation of the business in many ways. I have our head online instruction and our head of in-person instruction reporting to me and I have marketing people and finance reporting to me. So that gives me a broad part of the organization that I get to work with and thinking about how I can help make all of those individuals and their teams successful.

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What is a misconception that you think people have about education and opportunity?

The job that our instructors do is not just about conveying technical concepts and helping build technical fluency. It is [also about] about motivation and confidence building. When you set out to learn something really hard, you need to not only [understand the] technical elements of that topic, but you need to be able to not get frustrated and discouraged. We talk about perseverance, because if you keep at something long enough, regardless of what your preexisting aptitude was, you will eventually learn it.

There are a lot of parallels between instruction and great management. Great managers help people develop and thrive by also building their confidence. There's a concept that we talk about education of your initial learning zone, your stretch learning zone and then your panic zone. What we do -- and this is also what a good manager should do for people -- is we don't want people to be in that safe zone. We want to push them to their stretch zone, because that's where you learn.

Related: The Surest Way to Build Your Confidence Is by Not Fearing Change

How have you grown and changed as a leader in this role?

Coming here [from my previous roles], the approach to doing business was so fresh and different. There was an integration of technology in virtually everything that we do here that I didn't have in my last organization, even down to recruiting.

A word that is thrown around a lot is transparency. I have actually tried to strike that word in exchange for trust. Because I think that what people really mean when they say transparency is they want to have a trusted relationship, which means they have an opportunity to ask the questions they want to ask. They believe the answers they're getting back are truthful and are candid, and that there's actually a desire to develop the organization together in a collaborative fashion. We seek to develop a lot of trust in the organization in everything that we do.

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When was a time in your career when you made a mistake? What did you learn from it and how did you move forward from it?

When you're going through something that you know is going to change a lot of things, -- it's easy to go off, develop a plan and then come out and say, ta-da, this is a great plan. You shouldn't be worried about it because we thought about it a lot. Without a doubt, I have done that in my career.

A phrase that I talk about a lot is we have to bring people along with our thinking. You can't expect someone to go from 0 to 60 with you in a one-hour presentation, when it's taken you 90 days to do that. When you're in a growing organization, things are changing all the time. We've tried to find ways to create time for [constant] conversation, to talk to people about what are some of the biggest problems that we're wrestling with right now.

Treating people like adults and realizing that as leaders of the organization, words carry a lot of weight and have a lot of power. We try to be thoughtful about not seeing things in isolation and giving the broader context about what it is and bringing people along with our thinking in real time, rather than waiting for these moments in time where we feel like we have all the answers. People care. That's why they are here. They want to be a part of that process. And when you give them an opportunity to raise their hand to express their opinion, you get more perspective along the way and make better decisions.

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When was a time in your career when you had to advocate for yourself? How did you approach it?

My [leadership] style tends to be one where I ask a lot of questions and I do a lot of listening. I don't to tend to make snap decisions. [In the past I worried that I came] across as someone who didn't have conviction.

Now we're starting to get into gender stereotypes, where women are not assertive, are not decisive, aren't aggressive enough. I don't remember why it had come up, but somebody had said something [to that effect to me]. I went to one of our founders and I asked him, "Do you think that I walk away from issues too soon? Am I a pushover?"

He happens to be a very reflective person as well. He said, "I think that what you do is advocate for matters to a certain point, and then you walk away from it. But when you really care about it you come back to it. You always come back to it." [After that conversation I realized] this is who I am. This is the way I operate. When I have conviction on something I will advocate [for it] but I'll do it in my way.

Related: Why You Have the Wrong Idea About Who Is a Great Mentor

What is your best advice for someone who is about to make a career shift?

I think everyone needs to create focus on what really matters to them. What are you willing to do? What are you willing to sacrifice? And what do you want? What are the three things that matter to you?

I think you really have to sit down and say, "What do I want and what am I willing to sacrifice? What am I willing to put out as my effort and what am I willing to give up?" There's always trade-offs. I have three children. When I had babies, I was taking positions where I never worked at night and never worked on the weekends. I went home and I was with my kids every single night. Those are real trade-offs that we have to make. And it's not like you make them for the rest of your career. Think about the next two to three years, not the next 15.

Be honest with yourself about what is most important to you. And whittle it down to a short list so that you can then evaluate opportunities and go after them with incredible amounts of passion, because you've really [have] the discipline in your own thinking about what's most important to you. And when you find a work opportunity that really aligns with that, your passion for it and your desire to be in that role is really going to come through. And that's where you're going to thrive.

Related video: Entrepreneur Elevator Pitch Ep. 2: 'Has Anybody Not Seen That Product?'

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

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