career coach,legal professionals

John Costango

Prior to coaching, I developed my quantitative, risk management, operational, and leadership skills in many areas. For the last 20 years, I was an executive at international banks and broker dealers in positions including structuring and trading; credit crisis workout and litigation; global legal and regulatory program design and execution; and as Chief of Staff / COO for the global legal team at JPMorgan. Previous work included stints as an actuary, a risk analyst for financial guaranty insurance, and high school math teacher. My experience provides deep understanding of complex organizations as well as ways to take career risks and execute career transitions effectively.

More about John Costango

John Costango is a certified coach specializing in executive leadership and career transition. Prior to coaching, he was an executive on Wall St. in positions including structuring and trading; legal and regulatory program execution; and as Chief of Staff for the legal team at JPMorgan.

Through a close working relationship with legal professionals throughout his time in banking, John saw first-hand the challenges attorneys face as the legal profession transforms rapidly.  Technological advances, globalization of legal talent, legal and regulatory change, and legal business models operating at scale require attorneys and other legal professionals to reinvent themselves and apply their skills in new, daunting, and yet exciting ways.

Value Propositions

A successful attorney who is contemplating a career shift faces some particular challenges that are ripe for a coaching partnership. The self-selection that goes into embarking on a legal career and segregation of duties between lawyer and client often reinforce limiting beliefs about abilities.  Unaddressed, these beliefs undersell the attorney’s abilities and foreclose career change options.  And many attorneys have trouble separating their individual identity from their working identity:  “if I’m not a lawyer, who am I?” 

As a coach with a long career working closely with attorneys, I appreciate what makes the re-imagination of a legal career so difficult for many.  The very skills that an attorney refined and perfected in their role as a lawyer must be set aside for this career exercise.  Attorneys are often masters of the art of seeing how things can go wrong, identifying and protecting against downside, or finding logical flaws in a plan or argument.  Yet these same skills have only so much value when applied to personal and career decisions.  A coach will partner with a client to take on alternative behaviors more appropriate for this work such as creativity, curiosity, experimentation, and visualization of broad range of outcomes.


All coaching engagements start with a chemistry call, a get-to-know-you introduction of the coach and potential client.  In this call we discuss questions you might have about coaching, why coaching feels important to you now, and what you hope to achieve from coaching. I can also answer questions you might have about me, my coaching style and leadership philosophy. If the chemistry feels right to both of us and you want to proceed, we will agree on terms of a coaching engagement. 

A typical engagement lasts approximately 6 months and includes up to 12 hour-long sessions where the coach and the client engage in behaviors-based developmental coaching.  In this work, the coach partners with the client to determine a developmental goal that feels important to the client. The client and the coach then partner to identify behaviors the client can engage in that will move them toward their goal.  These behaviors form the basis for a developmental plan that will unfold over the course of the coaching engagement.  In between sessions the client puts the behaviors into action, collects data, and reflects on the results. 

Sessions occur over video conference with engagement and support between sessions provided by the coach as needed.

Method of Delivery for Services

  • Online
  • In Person