215-260-4881 gail@gailcummings.com

Executive and Career Coaching

Coaching helps people advance and pivot in their careers.

Gail works with individuals at all stages of career development, including those at the most senior levels. Her approach involves listening, supporting, challenging and asking helpful questions to guide her clients in a process that advances their careers.

Coaching Steps

  • Establishing and defining goals and priorities
  • Designing and implementing a realistic action plan
  • Identifying challenges
  • Developing strategies to move you forward 
  • Holding you accountable and on track
  • Owning and acknowledging your success along the way

Areas of Expertise

  • Advancing in your Current Career
  • Pivoting to a New Career
  • Negotiating Salary and Compensation Packages for Yourself
  • Developing Strategies for Productivity and Efficacy
  • Managing Anxiety and Stress on the Path to Success
  • Interviewing Prep and Writing & Editing Resumes
  • Guiding & Editing Annual Compensation and Self-Evaluation Memos
  • Developing Leadership Skills
  • Building up Confidence and Owning your Value

Being comfortable in your own skin is where grit and resilience begins. The strength of the relationship you have with yourself determines how you move in the world. And how you project to the rest of the world, will impact the strength of your collegial and business relationships. Relationships are a critical component of professional success – not to mention satisfaction and happiness.

“I have had the great fortune to work with Gail as my coach for the last several years. As a young Executive Director of a national trade association, Gail helped me navigate challenges when I was lacking experience and a peer network to draw upon. Her professional background combined with her extensive experience in coaching a multitude of clients allowed me to leverage a pseudo-peer network to help guide and validate my own decision-making. Importantly, Gail’s therapy background allowed me to share the emotional aspect of the work and navigate what was often the most challenging piece. Gail’s support was instrumental in managing my own well-being while continuing to deliver value to my organization. Ultimately, in working with Gail I was able to articulate my own need for change and develop an outline for what I wanted next and when the right opportunity arose, she helped me negotiate successfully for myself. Gail continues to be an instrumental part of my professional and personal success.”

Kendra A.

“Gail has been an invaluable support to me through two big job transitions, one a move from big law to in house practice and the other a geographic move half-way across the country. Prior to my transition out of big law, Gail helped me navigate firm politics and stresses and conceptualize and prepare for the next steps in my career progression. Since then, she has helped me position my skills and experiences to make me competitive for roles, strengthen my resume, prepare for interviews, and successfully negotiate two significant compensation increases. Career navigation can be daunting, overwhelming, and anxiety-inducing. I think it can be particularly challenging for women, especially any negotiation. I truly cannot imagine having navigated the past three years as smoothly, sanely, or confidently without Gail’s support. To me, her deep expertise and experience as a professional, a coach, and a therapist, have been the perfect combination. I have recommended Gail to every person who has come to me for career advice or insight. She truly is my not-at-all a secret to owning my career.”

Nicole F.

Attorney, Chicago, IL


215-260-4881 - gail@gailcummings.com