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Legal Talent & Inclusion

Growing Trend in Law Firm Talent Development: Hiring Full-Time Coaches & How It Helps Retain Diverse Lawyers

· 6 minute read

· 6 minute read

We speak to Diane Costigan, director of Coaching & Well-being at Winston & Strawn, about hiring full-time coaches at firms to better retain diverse lawyers

Full-time coaches are a growing trend at law firms, and Diane Costigan, Director of Coaching and Well-being at Winston & Strawn, estimates that around 30 law firms today have invested in full-time coaches as part of their talent development strategy.

Indeed, one of the greatest benefits of coaching is that the methodology is scalable and can be deployed to meet various needs of many individuals.

Coaching, historically, has been viewed as a signal for a performance issue and therefore, was not an essential component of a talent development strategy in Corporate America. Fortunately, that myth is fading quickly within the private sector and within the legal industry. In fact, Costigan says she spends about 5% of her time working with lawyers who “need immediate attention.”

Costigan says she spends the majority of her time working with partners on business development and with associates on career planning. Depending on the individual, coaching takes many different forms, she explains. For example:

      • She works with junior partners who want to take their business development efforts to the next level and aspiring partner candidates who seek help for creating a strategy plan to earn the promotion.
      • She works with practice leaders and supervisors on effective ways to manage teams, with the leaders’ goal of helping their attorneys hone business development skills or to free up their own time as leader to dedicate more time to business development.
      • Finally, she runs a few group coaching programs, one of which is dedicated to partners that are part of a under-represented racial or ethnic group, to help them build their books of business.

Role of Coaching for Lawyers of Color

A full-time coach within a law firm offers a level of individualized support and a space of non-judgment for attorneys who identify as a racial or ethnic minority. “One of the common challenges across this group when working on business development is that operating in a mostly homogenous environment is more taxing energetically, both from the mental and physical standpoints,” observes Costigan. The energy invested in dealing with the pressure to be perfect, for example, and the behaviors it leads to — the double- and triple-checking of assignments or being overly cautious in deciding when to speak up — erodes endurance and exacerbates the mental strain in an already stressful, hypercompetitive environment.

These diverse attorneys often describe this situation as a “double-edged sword of having to be perfect and not being able to make mistakes,” Costigan says, adding that the reasons behind this “energy tax” for lawyers of color can vary.

Diane Costigan, Director of Coaching and Well-being at Winston & Strawn

For example, lawyers of color who are striving to become partners and who may have grown up in a culture that operates with norms of respect and being deferential to elders and authority, may find themselves having to act outside of their cultural norm in a professional context and then in another way within their community — sometimes referred to as code-switching. This code-switching takes a toll on the individual.

This could result in a situation where an associate of color — who may also be the youngest or most junior person in the room — may see himself being respectful and deferential to other speakers in his own culture’s context; but in a big law firm environment, waiting or not speaking up at all could be career-diminishing.

Coaching Helps to Manage a Diverse Team

Costigan also notes that coaching produces positive results in helping a partner in managing a group of people from different backgrounds. In her one-on-one coaching sessions, she works with the partner to look at each individual team member to ascertain if the partner is guiding each person differently based on what each person brings to the table.

If, for example, a partner is reluctant to give constructive feedback to a woman, Costigan asks open-ended questions to help the partner understand what his role was in the woman not meeting expectations:

      1. What expectations were communicated about the work product at the beginning of the assignment?
      2. What about the deliverable did not meet expectations?
      3. Describe the gap between the expectations and the state of the deliverable when it was submitted.
      4. What do you think, if you were going to put yourself in that person’s shoes, might explain the difference?
      5. What do you expect to change about this situation if you do not communicate your expectation or your feedback?

The process of asking these questions empowers the partner to realize that he has to give the feedback, even if there is some discomfort about the act of giving feedback. When this occurs, Costigan works with the partner to rehearse the act of delivering feedback to help him explore what language feels best and most authentic.

Open-Ended Questions Hone Empathy & Perspective

The method of asking open-ended questions also helps increase the understanding of what another person is experiencing or going through. As Costigan used open-ended questions to resolve interpersonal conflicts between two individuals across generations, she says it was very common to hear, “Oh, I have never thought of that in this way.”

The process has also been successful in building more effective work relationships. In a situation between a more senior white male partner who is supervising work assigned to a second-year African American, LGBTQ female associate, for example, Costigan, as the coach, will literally reverse roles with the senior partner. Using the two chairs in her office, Costigan will have the senior partner sit in the chair across from her to give him the perspective of literally sitting in the shoes of the African American associate. Costigan then proceeds to ask a series of open-ended questions, starting with, “What do you know about that may be going on with her?” The most common answer from the senior partner is usually, “Well, I really don’t know.”

In response, Costigan will ask, “Well, how could you know?” and the partner then arrives at his own answer of the next needed action, “Well, I could spend more time understanding what it might be like to be this person… .”

In order to expand the benefits of these sessions across the firm, Costigan is partnering with Winston & Strawn’s chief talent officer and director of learning and development to create a leadership curriculum to broaden the use of coaching skills and the use of open-ended questions firmwide.

Costigan says she knows it will not be easy for seasoned lawyers to learn, simply because coaching is a completely different method from the typical way lawyers operate — answering questions rather than asking them. In the long run, however, Costigan recognizes the overall potential positive impact. “Using a coaching approach often takes things off of your to-do list because it’s always meant to empower the associate or whoever you’re coaching,” she explains. “It will free up our leaders to allow them to engage more in the actual relationship.”

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