The Most Overlooked Career Hack

Headhunters wish more investment professionals knew about career coaching. 

“I’m always interested in top-notch talent, but being a career guide for someone who’s not looking to move? That’s not what we do,” says one elite recruiter. 

Another finds that coached candidates outperform in interviews, especially if they left their last job on delicate terms. Otherwise, professionals too often show up still reeling or healing. 

“Even if through no fault of their own, there’s often a lot of anger, fear, or insecurity that comes out unconsciously through conversation,” says the recruiter, who has placed legions of asset management executives. “And I tell people, ‘You’re not ready right now. You need to talk to a coach and constructively move beyond whatever happened. Know how to talk about it.’” 

Feedback from a third party tends to help everyone in their personal presentation, coaches and recruiters say. Laurie Thompson of Willow Hill Advisors is both, running searches and coaching individuals in the asset management distribution arena. “You would think that client-facing professionals would be very thoughtful around how they position themselves, but they’re not,” Thompson says. “With me, people are getting all the things that recruiters would love to tell you if they had the time and reason to.” 

The investment industry warmly patronizes consultants for almost every area of expertise (legal, prospecting, clawing power out of aged hedge fund founders’ wrinkled clutches, etc.). Ask around, and one might be surprised at how many successful individuals have worked with coaches. Many major organizations bring in outsiders to help with talent development. 

But coaches freely admit to encountering confusion around what they do and who it’s for.

Transitions are core to the work: helping clients figure out where they want to go, what they’re good at, how to reach their goals, and guiding them as they do it. 

Former recruiter Sloan Klein works exclusively with investment industry types, many of whom bring her on at the outset of their job searches. “My process starts with a self-assessment to identify a client’s core competencies and skills, and then overlay them with market opportunities,” she says. Klein helps in crafting narratives; positioning pitches, resumes, and LinkedIn profiles; interview prep; networking; and provides ad hoc support for interviews as they come up. 

“There’s a lot of behind-the-scenes collaboration around emotions and how to behave at different junctures in the search process — when to respond or not respond, for example,” Klein explains. “At the end, I help them negotiate the most competitive comp package and optimal structure to the role.” She reviews employment contracts before signing.

Klein and other coaches generally act as on-call experts in a candidate’s corner. “What I’ve always enjoyed is helping people make career decisions,” she says. “Job transitions can be stressful: Your career is one of the most important elements of your life.”

Kate O’Sullivan, for example, began coaching colleagues at Bridgewater Associates, before departing to practice full time in 2012. A Bridgewater ex-coworker named Mike Schmitt hired her and was surprised by the value her coaching offered. “He was like, ‘Why don’t more people know about this?,’” she recalls.

Schmitt and O’Sullivan ended up as business partners, co-founding P.S. Your Career last year. “People often think coaching is some kind of punitive thing or that they need a recruiter,” O’Sullivan says. “But recruiters don’t work for you.” 

Individuals — many from the investment world — pay between $150 and $600 per session for coaching via P.S. Your Career, which matches clients algorithmically to its roster of a dozen or so coaches. 

But the firm is an exception in selling one-off sessions. The leading coaches in asset management tend to work with clients for several months at a time and price their packages accordingly. 

On the luxury side of the spectrum is Matt Spielman of Inflection Point Partners, whose clientele spans hedge fund and private equity professionals, big pharma employees, and media executives. Some corporations pay $25,000 to $35,000 per employee for six months of Spielman’s services, while individuals shell out about $15,500 for four to six months. He doesn’t do anything by the hour. 

“I’m not the top-top end, but I’m probably at the higher end. I’m a few notches below the celebrity coaches,” answers Spielman — a graduate of Columbia University’s vaunted coaching program, known for its rigor in a “squishy industry” — when asked about his price bracket. “I have some really well-known clients, and so confidentiality is number one.” 

Among his individual clients, “typically they’re looking to transition out of a company, or don’t have a job, or want to rethink their career and life more broadly,” he says.

Spielman, like many of his peers, meets with clients weekly or every other week, often remotely even pre-pandemic. In between, he’s available over text, email, and phone. “Sometimes the magic happens in between the sessions.”

But sometimes the magic doesn’t happen at all. 

Of six top coaches in asset management, four say they’ve fired clients. 

“I just did last week — it was terrible,” laments Manny Correia, who previously spent 25 years at Harvard’s endowment (before that office fell into dysfunction). “That was the second one I’ve done. As a coach, it’s really hard. You lose sleep.”

Correia and his peers tend to pull the ripcord when they realize they can’t help the client for whatever reason — but most often it’s a lack of will. “If the person won’t try,” Correia says, “I’m not sure I can help them move forward.”   

That experience is universal among leading coaches, including those who haven’t actually broken up with clients. “What can’t be changed? Self-awareness,” says Lou Chrostowski of Sloan Group. “Some people just don’t want to take a hard look at themselves. If a person is not receptive to feedback, you’re going to be pounding your head against the wall.”