Are millennial bosses really cool?

In a career spanning five years, Bengaluru’s Ananya Bisht has worked with two bosses who were millennials, belonging to Generation Y (born between 1981 and 1996). Dealing with them wasn’t the best part of her work life, for the managers were rigid and inflexible, quite the opposite of the popular notion that millennial bosses are “chill” and prefer not to pass down any negativity to their workers.

“Their job dictates their life—which is what they also expect from their team members,” says Bisht, 32, who works as a sales professional in a tech start-up. “Many millennial managers exhibit toxicity through their actions, either they will make you stay back at work until late or they will inundate you with work and set unrealistic deadlines.”

Millennials are leading companies today across industries. This is in line with a prediction global consulting firm Deloitte made a decade ago: 75% of the global workforce by 2025 will be dominated by this generation.

While most offices have a multi-generational workforce, it is the millennials who are increasingly stepping into managerial roles. A 2020 survey of over 1,000 people in the US by workflow automation software company Zapier concluded that at least three in five millennial employees manage direct reports.

With their entry into the big office cabin, they have also introduced a different style of leadership: a “cool” boss who’s flexible, purpose-driven, and transparent in communication.

Millennial leaders are “rooted in an unbounded ambition for positive impact and propel organizations forward in a fast-evolving world,” argues Keshav Reddy, a millennial and founder of Hyderabad-based Equal, a digital platform for Indians to share IDs with one click.

The desire to push ahead and meet targets, however, has pushed many Gen Y bosses or managers towards overworking, so much so that they can put unrealistic pressure on themselves and their subordinates to complete tasks on time—a work ethic they have perhaps learnt from their Gen X parents. Small wonder then there are often reports stating that millennials are dealing with burnout, tiredness, and work-related stress.

“Unless millennial bosses are willing to unlearn old assumptions and styles, they will alienate younger millennials and Gen Zs (who generally prefer working at their own pace, are more independent and stricter about work-life balance),” says Leena Chatterjee, organisational behaviour professor at BITS School of Management, Mumbai. “Micromanaging and being rigid can lead to high rates of attrition and disengagement.”

Being too cool, where bosses seem laidback, can go the wrong way as well, if a fine balance isn’t maintained, says Delphin Varghese, 42, co-founder and chief business officer at Gurugram-headquartered digital marketing agency AdCounty Media, who has worked with Gen Y managers.

“One needs to understand the difference between being relatable and creating an environment that may be potentially damaging. A forced attempt to be laidback or cool may come across as superficial and can erode trust and authenticity,” says Varghese. “It can seem like a fake attempt to connect rather than genuine leadership.”

According to Anant G., 28, some “cool” millennial bosses only pretend to care about work-life balance or the well-being of their employees. “While my millennial boss may appear interested in flexible working hours or pretend to understand my caregiving responsibilities, he’s hardly taken any action in the past two years since I discussed my challenges with taking care of my ailing mother,” says Anant, who works as a content manager at an advertising firm in Mumbai. “My boss gives me some extra time to complete assignments… but I have been termed inefficient time and again.”

It’s about balance

What makes for a cool boss? It is all about setting a positive example for team members by fostering creativity and open expression to bring about inspiration, says Varghese. “There will be ups and downs, but staying consistent through all of it is what truly defines a cool boss or a great leader. A persistent positive approach is what magnifies employee motivation and drives the growth of an organisation,” he reiterates.

Agrees Aman Jain, 33, co-founder and chief executive of Delhi-based Doodhvale, an app that offers milk delivery. He believes the most effective millennial leaders prioritise authenticity, vulnerability and trust-building. “It’s crucial to recognise that leaders set the tone for workplace behaviour, since any toxic practices they engage in can permeate the organisational culture,” says Jain. “Millennial leaders need to be mindful of their influence.”

Every generation faces the challenge of managing a team of younger individuals who believe in a different set of work ethics. It can also be non-intuitive to work with them if their way of communication, learning, and having fun is foreign to one’s upbringing, says Karthik Sridharan, 32, co-founder and chief executive of Bengaluru-headquartered Flexiple, a platform that helps build tech products. “This can lead managers to try and fit in. Instead, they may end up behaving in a manner that’s unnatural to them even if they have a positive intention. It will only make them appear awkward, funny, or plain uncomfortable,” he says.

While there may be certain negative tropes attached by the younger generation to millennial managers, Aparna Jain believes Gen Y bosses strive to foster professionalism in the workplace, aligning with the task-oriented leadership style they have. She is the head of the department of business studies at SK Somaiya College, Mumbai.

“They prioritise creating a professional work culture over maintaining personal attachments, encouraging employees to focus on their performance,” she says.

Equal’s Reddy admits that millennials have a contemporary style of leadership that also has hints of the traditional way of leading the company. He, too, follows a modern style of leadership with some management rules borrowed from old-school companies like his family business GVK Industries. For instance, there is rigorous tracking and the unsaid commitment to complete the tasks at hand. However, when approached with a balanced perspective, it helps create a more dynamic and efficient workplace, Reddy believes.

In such scenarios, a change in organisational culture can bring up resistance. According to a Deloitte report, to attract Gen Z, employers must be ready to adopt a speed of evolution that matches the external environment.

What a company needs

It all begins with setting clear career goals that are not just challenging but also aligned with the overarching purpose of the company, says Reddy. What’s more, transparency in target setting, accompanied by diligent tracking of progress is essential to maintain accountability and ensure everyone is on the same page. “Fostering a culture of fun and camaraderie outside of work helps build bonds of friendship and trust within the team,” adds Reddy.

Irrespective of which generation one belongs to, it is important for every boss to actively listen to the concerns of their employees while making a decision, according to Varghese. “Acknowledging the hard work put in by employees is important to boost their morale and create a collaborative team culture.”

The role of any leader is not to be perfect but as genuine as possible, says Sridharan. “Trying otherwise can lead to relationships being severed.”

Geetika Sachdev is a Delhi-based journalist.