C-suite career advice: Tara O'Sullivan, Skillsoft

What tips would the c-suite give to the next generation?

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Name: Tara O’Sullivan

Company: Skillsoft

Job Title: Chief Creative Officer

Location: Dublin, Republic of Ireland


What was the most valuable piece of career advice that you received?

Hire people who are smarter than you. It consistently brings up the level of the team and makes sure that you are learning all the time.


What was the worst piece of business advice that you received?

You need to change your personality to fit in. I remember back in college a friend of mine and I were talking about getting ahead in business, and I talked about wanting to manage teams, etc. He (shock) advised me (with an arm around the shoulder) that in order to make it through the business world I would need to be more retiring and not speak up as much. He called me too challenging! He felt my opinions would make people (presumably men) feel uncomfortable. The awful thing is that for about 10 minutes I did consider it. But only for 10 minutes ☺


What advice would you give to someone starting their career in the tech industry?

Get a sponsor – not a mentor. Mentors are great, but women in technology especially are being mentored to death. We need a sponsor. A sponsor is someone who puts you in the way of opportunity when you are not in the room – they have power and influence and can positively impact your career. True sponsors are rare, and if you find one, you need to nurture that relationship. Another piece you need to understand in tech is how fast it moves – you need to find a way to keep yourself abreast of the constant changes in competition, the market, the technology. That’s a challenge in itself.


What tips would you give to someone aiming for a c-level position?

I guess I never aimed for a C-level position I just aimed for the next one up from me. I always had a three-year, five-year and ten-year plan – honestly I did, but the real focus was getting really, really good at the job I was doing now, and figuring out how to do the next job up. I believe you need to work incredibly hard; there are no short cuts. You need to know the business inside and out, and make sure your team is supported and recognized when they do great work.


Are you particularly proud of any career advice that you’ve given or the career route/development of anyone you’ve mentored?

Never stop learning. I remember a friend of mine, who I used to work with years ago, called me one day and asked me how I kept learning. Marketing was my major and I love it – I read a lot of books, watch videos about it and read articles. She asked me how I keep up on the new things happening in industry and career focus. I explained that I have Google searches saved for various things, and when I take on something new I go into a major deep dive to make sure I get an understanding about how everything works. Also – I try to get people to take presentation skills courses – I think it’s very important in this day and age that people can communicate effectively to groups. And lots of people cannot. I think knowing enough about the subject isn’t enough – you have to tell a story that inspires the audience. I’ve been reading some great books this month about corporate storytelling – that’s my latest deep dive!