Leadership Coaching and Training

Although Kate was hired as an external trainer, it felt like the moment that she started with us she was clearly prepared and able to understand our workplace environment. She was able to dig in right away with us and jump into the difficult challenges our group faced. She is a natural facilitator, able to quickly engage the group and create an open space for discussion. Kate was able to relate to many of the challenges we were struggling with and often added in her own examples (of which were applicable and entertaining). I found her training to be thought provoking and I left with clear tangible takeaways.

Manager , Costar, Washington DC

Kate was highly engaging, told great stories that brought the content to life (and kept us interested), and really knew her research. I went into the training rather skeptical, because most training classes I have been to are very dry; and I don’t take much from sessions that are essentially daylong lectures. This training was different right from the start because Kate asked each of us what we wanted to get out of the training. This created a conversation right away, and she was able to adapt the content to meet our organization’s needs in the moment. This was the most helpful professional training I’ve had in my career.

Manager , Deloitte

I would strongly recommend Kate O’Sullivan for your training and coaching needs. The Annie E. Casey Foundation has been a client of Kate’s for the past two years, and I am extremely satisfied with her presentation and training skills, as well as her one-on-one coaching. Last year, Kate led a workshop on career coaching for a group of 15 staff members, and has provided follow up coaching for individual staff. Kate’s workshop presentation was particularly effective and engaging because she provided concrete examples and case studies. In her coaching, Kate is able to connect and build trust with her clients quickly – she is a strong listener, asks good questions, and is insightful in her advice. Kate’s coaching clients rave about her effective guidance and support. One of Kate’s coaching recipients was originally going to split his allotted coaching sessions between two coaches, but after two sessions with Kate decided to stick with her saying “she’s just too damn helpful!” I would recommend Kate without hesitation.

Program Manager, Annie E. Casey Foundation

I love the way that Kate listens to what I’m saying and then plays it back to me to get at the core of an issue. She has really helped me approach several management challenges with more confidence and with a thoughtful strategy. I always think about our conversation about expectations + accountability = results. She pushes me, but also has a great warm demeanor. She is very intentional about setting goals for coaching. I like Kate’s focus on what you’re already doing well and trying to nourish those skills, rather than changing who you are.


Manager in News and Media

Career Coaching

I was getting interview requests here and there, but they weren’t for the types of jobs I was targeting. After Kate revised my resume and helped me with my personal branding, I immediately started getting positive feedback from recruiters and got my foot in the door for the roles I really wanted.

Client in the Marketing Industry

The interview practice and cover letter reviews were the most helpful to me. Cover letters are, I’m convinced, a form of torture that probably incentivizes people to stay in bad jobs longer than they should. Kate demystified this process and made it easier. Additionally, her observations and feedback helped me build better self-awareness and answer interview questions more cleanly. In general, Kate is a very affable person and she is great at establishing a conversational and nonjudgmental tone. This made it more comfortable for me to practice things like answering interview questions and doing my elevator pitch multiple times.

Program Manager, Education Non-Profit

A recruiter and hiring manager (separately) told me multiple times during the interview process that they normally wouldn’t have brought someone with my background in to interview, but they loved my resume so much they decided to talk to me. I got the job.

Client in the I.T. Industry