The Art of Stealth Mentoring

Choosing the right person is a subtle craft.

Last week I wrote about mentoring, but there’s plenty more to say, in part because finding the right mentor can be such a challenge. So I’d like to talk a bit about how I found the ideal mentor, using what might be called the stealth approach.

What is a stealth mentor? It’s someone you choose because they represent some aspect of what you aspire to become but whom you doubt would say yes if you asked them outright. This may be because their reputation is daunting or their connections stellar. Or simply because you aren’t sure they’d see you as a good fit.  

All these reasons held me back from trying actively to engage my self-chosen mentor Frances Hesselbein when I met her back in 1988. At the time, Frances was CEO of the Girl Scouts USA and I was a freelance journalist who’d managed to secure an interview with her for a book I was writing, The Female Advantage: Women’s Ways of Leadership. 

I’d first learned about Frances in an article by Peter Drucker, the most famous leadership guru of that era. Peter, who’d been a special advisor to the former CEO and Chair of General Motors, caused a stir when he asserted in Fortune magazine that Frances would be an ideal candidate to lead GM. It was unheard-of in those days to suggest that a woman could assume such a position, much less a woman who led a non-profit that served girls. Peter’s comment made news around the world.

Clearly, Frances moved in exalted circles, but that wasn’t the only thing that held me back from trying to position myself as her potential mentee. We also inhabited different spheres: she led a famous organization, while I spent most of my time in my apartment writing. In addition, her put-together style contrasted with my slightly scruffy Greenwich Village demeanor at that time. I remember once vowing upon leaving her office that I would not return until I’d seen a manicurist. 

But though I lacked what I believed were the right credentials, I knew from the moment we met that Frances had much to teach me. In particular, I admired her ability to balance professionalism with authenticity, to be tough and resilient without seeming arrogant or cold. And I was struck by how she navigated a world that was then entirely dominated by men without trying to adopt a male persona.

Throughout the 1980s, “acting like a man” was widely presumed to be necessary for any woman seeking to be successful in the workplace, and my whole point in writing The Female Advantage was to push back against this almost-unquestioned notion. Frances exemplified how it could be gracefully done. 

She was also, of course, extraordinarily well-connected, whereas I was not. This played a key role in the attraction I felt for her. I knew that finding the right mentor was probably my most effective means of expanding my network of allies. We elevate ourselves– or not– based upon our associations, and I saw value in associating myself with Frances.

Yet because I assumed that asking for her help or guidance directly would not meet with success, I sought simply to remain in her orbit and be useful– not only to her but to people I met at her events. Over time, I became a familiar presence, and many of her friends and allies became my own. At the same time, I continued to watch and learn from how Frances operated in the world. 

Although I remained a part of her circle until her death late last year, I doubt Frances ever knew that I viewed her as my mentor. We were never on intimate or confidential terms, and it took decades before I felt entirely comfortable in her presence. Yet she served as my mentor nonetheless.

This is the real power of the stealth approach: it enables us to be bold about who we choose. We don’t need to fret about securing an agreement or worry that we might feel rejected if turned down. We just have to find an appropriate way to put ourselves in our stealth mentor’s company when the opportunity arises. And to be diligent about learning the lessons we believe we need to learn.

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