The Power of Reverse Mentoring

Just as the pandemic was surfacing, Mary Crail, a robotic process automation (RPA) expert, collaborated with the NEWGen Group to develop a reverse mentoring program for the organization. As a pilot test of the program, Crail reverse-mentored Sarah Alter, NextUp’s President and CEO.  

Now Product Manager at Numerator, Crail found being a reverse mentor an “empowering experience.” Although she initially felt intimidated, she quickly recognized the value that she brought to the table. 

“When I started, I was 26, new to NextUp, newer in my role,” Crail says. “And there’s the CEO, president of this organization, fascinated with me telling her about RPA technology – and just that confidence that that can give you early on in your career, I think is really powerful.” RPA helps automate repetitive tasks in businesses that can bog down employees, especially when there are fewer staff to wade through time-consuming busywork. In a pandemic, where businesses were cutting back on staff or losing them because of parenting needs, Crail’s understanding of RPA was invaluable.  

In addition, Crail’s point-of-view as a millennial offered Alter a window into that generation’s expectations in the workforce, and how they contrast with Gen Z. “Walking through that with Sarah and layering in some of my own personal experience I think made for a really robust conversation…really focusing in on the different things that Gen Z and Millennials want in the workplace, and what companies can do to accommodate those differences and provide a healthy, preferred work environment for Gen Z versus Millennials.” 

When asked about the Reverse Mentoring experience from the other perspective, Sarah Alter said that she “would strongly recommend that all leaders and companies include reverse mentoring in their overarching efforts to build out support for all employees. I truly benefitted from Mary’s unique perspective on the many current dynamics at play in our world, and I leveraged her knowledge of technology – TikTok, for example. I blame her now for my daily addiction.” 

“Joking aside, the most successful of executives and businesses will be committed to seeking better understanding of the shifting generations, their perspectives, and embracing the pivotal roles they play in helping to shape the future!” 

For executives reentering the workforce, Crail has several gems of advice regarding how to get started with the job-seeking process and how to prepare oneself for interviews. Her first suggestion is something she learned from her own mentor. 

“She said, ‘Be picky. Make a list of what you want and what you’re looking for and don’t feel like you have to compromise.’” 

Another important piece of the job search puzzle is identifying one’s network. While people often associate “networking” with standing awkwardly in a conference hall with a nametag and a plastic cup of wine, it can simply be a reckoning of who has your back. Former co-workers, classmates, mentors, professors, friends, or even someone whom you met in a webinar can all be part of your network. 

“For my involvement in NextUp, it’s been really great to build out a network,” Crail says, adding that connecting with other executives can mean “taking yourself out of the bubble that you’re in, in your own company, and hearing what other people are doing or seeing moves that they’re making.” 

Jobseekers who wish to reassess their skills can also turn to NextUp for guidance. Crail participated in a 360 assessment through NextUp’s Rising Stars program, but all NextUp members have access to the ADVanced Insights assessment. Participants privately identify their natural talents, motivations, and lesser developed areas that could be strengthened with further education. 

Crail also recommends investigating which resource groups are supported by employers. She  personally found it reassuring when she saw that executives at her company followed NextUp on LinkedIn. 

“Especially working in the tech space – it’s very male-dominated,” Crail explains. “Women are growing in leadership positions, but I think seeing [that] NextUp was something [an organization’s] employees were engaging in was a comfort, and also bolstered the DEI initiatives that they had listed on their website.” 

Digging deeper into the research, Crail likes to prepare by creating a “crib sheet” in which she compares an organization’s mission and values with her own. Then, she fills out detailed bullet points to explain how her skills and experience match those values. In this way, she sets herself apart as a candidate whose beliefs are aligned with the employer’s and who is already seeking ways in which she can contribute to the existing culture. 

As a reverse mentor, Crail’s takeaway is that having a dream role and company in mind, connecting with likeminded executives, and being discerning about work cultures are all key factors in a successful job hunt. Not only that; it’s a good time to be looking for work right now, with the talent pool so small compared with the numbers of jobs that employers are struggling to fill. 

“I do think that it’s kind of flipped,” says Crail, “and that companies need to be selling themselves to you as much as you’re selling yourself to the company right now.” 


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