Talented managers and successful executives are often faced with the dilemma of being inundated with mentoring requests at the cost of sacrificing time for daily responsibilities.


Sally Helgesen, an author, speaker, and leadership development consultant, argues that organisations often try to address the mentor gap by instituting formal programmes.


“While these can be helpful, effective mentoring thrives on chemistry, which is hard to mandate and does not necessarily respond to assignment. It can work but it can also feel generic, awkward, and dutiful. There has to be another way,” she wrote.


Helgesen raised the example of Paul Smurl who, after working as an attorney and management consultant, held a range of positions managing online products, strategies, and subscriptions for the New York Times for nearly 12 years. But in 2015, Smurl surprised colleagues by leaving to take a position as president and COO of Some Spider, an Internet publisher founded by e-commerce star Vinit Bharara. Some Spider owns the popular parenting site Scary Mommy and has restarted the topical satirical site Cafe.


After making this gutsy move, Smurl knew that breakthrough success would require new skills, fresh insights, and an expanded way of viewing the world. The Some Spider demographic skews fairly young, which meant that Smurl, nearing 50 and married with children, needed to sharpen his understanding of the next generation’s media habits.


The challenge he faces when it comes to new messaging technologies such as Snapchat and Yik Yak isn’t technical — it’s strategic.


So, like anyone looking to up his or her game, Smurl needed a mentor. He ended up turning to Kareem Rahma, a former colleague from the Times who had worked in audience development. Kareem is now CEO of Nameless.tv, a social media startup that offers original video content along with chat functionality. A 2008 graduate of the University of Minnesota, he is also decades younger than Smurl.


Based on his experience, Smurl advocates engaging younger mentors. Prestige shouldn’t be the marker that determines a mentor’s potential value, he says; rather, people should consider “what can help.” Of course, having a mix of mentors is ideal. In addition to offering lessons in management and in life, older mentors tend to have long-standing relationships that can be helpful. But given the extraordinary four-generation range of people in organisations today, from 20-something millennials to 70-year-old matures, and the fact that digital natives possess a bred-in-the-bones feel for how technology is driving change, there can be real value in thinking outside the age-frame box.


How can you make December–May mentorship relationships work? Smurl has three suggestions for those intrigued by this route.


1. Be self-aware.

2. Don’t take a transactional approach.

3. Recognise that mentoring should be a two-way street.


Though mentoring connotes sharing your wisdom or insights with someone else, if you never perceive a benefit to yourself, you will eventually lose motivation. In Smurl’s view, formal mentoring often founders because the incentive is all one-way. The desire simply to be magnanimous can make mentoring gratifying, but it’s likely to pall when things get really busy. At its best, mentoring is mutually beneficial, no matter what the mentor and mentee’s respective ages.

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