Knowing When to Move On

TCDI’s Caragh Landry explains how taking risks has defined her career. 

CCBJ: Can you talk about your path to leadership, and any difficult decisions that stand out?

Caragh Landry: My path to leadership has really focused on two areas: my willingness to learn new things and my enthusiasm for taking risks. For example, right after college I moved to San Francisco and stumbled into litigation support by answering an ad for an administrative position at a very small company. However, I came out of that interview with a job supervising an entire team. I had no idea what the team members did, so I had to learn their job functions, and it was imperative that I learn quickly. In order to properly support the team, I also had to learn the responsibilities of the delivery teams adjacent to my team – those working in other phases of the e-discovery process. That’s how I was able to move into my next role: I learned what the teams were responsible for in the next phase of the e-discovery process and was able to join that team. At that point in my career, I found myself moving from a QC team into various project management, client services and product management roles. I also gained experience in various technical roles. Through the diversity of experience I gained, I quickly became a subject matter expert in the industry, which ultimately led to a path into leadership roles. Continuing my education and taking risks along the way really helped me advance my career.

There were many difficult decisions I had to make along the way. I had to know when to transition into a new role, when to be okay with not mastering everything, as well as when to leave a company and start over fresh. Those were all really tough decisions for me. Each time a new opportunity presented itself, I had to stop and think if that was the right one for me or not. I think that’s probably been the most difficult of the decisions, knowing when to take the next step and when not to. When had I learned enough to move on?

Have there been people or experiences that helped guide you?

Absolutely. I’ve learned many things from both good and bad leaders. I watched everyone I worked with to understand how they managed their own teams and performed in leadership roles. I tried to look at the good and the bad and create my own type of leadership.

My career choices have been influenced by the work I can accomplish in the new role, and by the people leading the company or department. So, aside from the work itself, I’ve looked specifically for opportunities to work at organizations where there are visionaries in leadership roles. I want to hear passion and excitement from leadership. When the leadership team is excited about the things the company is doing, that excitement trickles down to all the employees as well as to the clients.

The biggest impact on my career was when I took the leap to a true startup. Five of us launched a company, and we all had to wear multiple hats. We had to find footing in places where we had none, and we had a lot to learn in a very short time frame. At the time, I was only 30, and it was a lot to take on. Thankfully we all worked really well together, and it wound up being a very successful company, still in business today. That was a pivotal moment that got me to where I am today – taking that leap and learning from the responsibility of having a company on my shoulders.

What are some key challenges you’ve faced along the way?

The greatest challenges for me have been my shyness and lack of confidence. They were issues for me for years. After taking on all of those various roles and learning the different pieces of the e-discovery process, I became an expert and therefore often found myself the center of attention when those things were being discussed. Growing up, I was never comfortable being the center of attention, so I struggled early on to get past my shyness. I had to learn to speak up in both small and large groups.

When I started to advance in my career, my confidence also became an issue. I was usually the youngest person in the room counseling people much more senior. I’m not an attorney, and I was usually in a room full of attorneys. I was a woman, usually in a room full of men. These three things often overwhelmed me, and I struggled to overcome my insecurities.

What really helped me overcome the shyness and confidence issues was time and experience. Over time, I became more practiced at being an expert in the room. I gained confidence and just relaxed into my role. A turning point was when I started to think of myself as a teacher, which was an original career aspiration. Thinking of myself as a teacher, rather than an expert, really helped me reset my own expectations, which then helped me overcome those issues.

You’ve brought this wealth of experience and knowledge to TCDI. What’s your perspective on your role and leadership style there?

I think of myself as a thought leader. I see my role as bringing people to the table to have conversations about current and future trends, and to work as a group to decide on the next step. It’s probably the project manager in me, but I think my major responsibility is to get people to that table to develop really good ideas.

As for my leadership style, I’d say “collaborative.” I feel that I can contribute ideas and champion strategy. I know that I have some good ideas, but I also value the ideas of those around me. I like roundtables where everyone is talking and giving their perspective, and I truly believe that’s how a successful company moves forward and becomes a leader in their industry. So I see my role and my leadership style as really facilitating those conversations and making sure everyone is contributing.

Is there one piece of advice you’d give to other women looking to advance their careers in legal services?

I’d say, be proactive in terms of career development. That’s definitely what worked for me. From being willing to relocate to a new city, to seeking out a mentor to learn a new skill, to asking for the role that you want outside of your current comfort zone. You have to ask for those things – you can’t expect them to come to you. Sitting around and hoping to be recognized and rewarded for your hard work – that’s not the path to success. So it’s really important to be proactive and know that you can actually influence the advancement of your own career.