Kenneth Oswin Lean Organisational & Leadership Coach

Reverse Mentorship: Breathing Life into Corporate Hierarchy

3 min read

Reverse mentorship

It’s not every day we promote unlearning over learning. And yet, we have to do it every day.

Seats at the table

Think about the traditionalists, the GenX, and the millennials. The older folks fulfil a core functional expertise. They were the first to operate via emails but still held on to their hierarchical modes of operation. Thanks to digital transformation, the younger leaders have the technical skills to fulfil dynamic business needs with agility and flexibility. 

For instance, all sorts of work can be done more efficiently with AI and ML. From saving lives to individualized medicine, online learning to automated services across different industries. AI and ML are the next big thing for market research, communities, startups. The older leaders may have an idea about these innovation opportunities but it will be the millennials who primarily drive them into the market.

I believe both are required. For boardroom conversations to be relevant in today’s world, there has to be a healthy relationship between human minds and inter-generational intelligence. And reverse mentoring is one of the solutions. And unlearning is vital to making the most of reverse mentoring. Here’s a peek into one such dynamic.


Casey is the Chief Storyteller at the CEO’s office. She spends her time in boardrooms observing and researching what it takes to connect with, inspire, and motivate human behavior. But she knows little about how to run the business. That’s not her job. That is for her mentors to do. 

She’ll brush past the office hallway, and important things do not miss her eye. Catch her in her pajamas on a weekend and she’ll overshadow any gamer at a gizmodo. She does this thing where she doesn’t correct people’s faults but nods understandingly. Her agility to learn and empathy to listen are among her greatest strengths. 

She’s young, talented, and in vogue with the times. Work formals are so 2019. There’s always something new. Fashion sense, Twitter banter, and work ethic.


McGrady is in his late 40s or early 50s. A big-picture thinker, he’s exceptional at what he does. With the need for tech-savvy leadership, he finds himself relying on his younger colleagues for a simpler and faster way to operate. They do not discount his experience. An experience measured in meaningful failures and purpose-driven successes.

He knows better than anybody that there are no cookie-cutter solutions to problems in a dynamic market. Business acumen, protocol, and mature decision-making skills have come to him with time.

The new kids on the block, the gig-economy and reverse mentoring, promise massive reservoirs of talent, fresh perspectives, and innovation. He’ll invite millennial colleagues into the boardroom and to lunch on a Sunday. 

His mentors were the traditionalists. He learned negotiation and trade secrets from his seniors. But the ability to learn and unlearn resiliently, he learned from young leaders like Casey.

Can someone pass the agenda, please?

In fact, big tech orgs have synergistic, agile, reverse mentoring programs. The agenda is three things.

  • Staying abreast of technology
  • Developing more empathetic perspectives 
  • Reducing unconscious biases that block true progress

In today’s global village of the social era, technology connects these dots of cross-generational intelligence. For example, a young smart Executive Assistant like Casey can make sure the CEO’s ideas are translated into better solutions. Which if left alone for McGrady to do, he wouldn’t do it. He is culturally not equipped to be flashy, and win over a social media audience. But Casey, as a storyteller, does it in record time. 

Reverse mentorship allows McGrady to grow in the area of his discomfort. Just as Casey spends her hours at office intently learning, unlearning, and upskilling herself, McGrady gets reverse-mentored in technology and a mod way of doing things. The whole organization works like this. The scales are tipped upside down and they have the brightest teaching the oldest.


It is interesting that reverse mentoring may require more effort from the mentor than the mentee. One reason being, the mentor may not be having kids but the mentee is used to such a dynamic because of parents.

Mentees cannot be expected to rise up to the occasion and interact with their seniors. It is for the mentors to put themselves in the mentee’s shoes and listen more than speak.

Non-negotiables that tend to hinder healthy reverse mentoring:

  • Ego

By ego, I mean that of the older people. I had a mentor who told me, ‘When I was in uniform, you weren’t even in any form.’ If that ego comes into the picture, both won’t benefit. And the effort goes to waste.

  • Unconscious bias

It is very likely for mentors to assume that what worked for them before is science. If they hold onto outdated mechanisms even an absence of ego cannot help. The only way to get past this bias is the willingness and ability to unlearn.

  • The platform and style of communication

If you’re going to make these conversations very formal, mentees will find it hard to relate. Conversely, if it is too informal and urban dictionary-like, the mentors may not understand. The trick is to have an equally professional and friendly platform and style that mutually benefits the two. 

A Forbes study reports that inclusivity is crucial to innovation. And reverse mentorship programs can huddle in a diverse workforce, connect professionals of different ages, exceptionalities, ethnicities, and gender.

In the gig-economy, the hierarchy is flipped anyway. Companies across the world are mobilizing non-traditional teams. It is talent over geography and age. This helps organizations gain a competitive advantage in a tech-heavy landscape. While fostering inclusivity and diversity in boardroom conversations.


Kenneth Oswin Lean Organisational & Leadership Coach

Get the latest market research insights