Understanding Millennials in the Workplace

Are the challenges and struggles in the workplace of this generation attributable to the millennial demographics alone? How has the hiring process changed over time and affected the way organisations function compared to previous generations? Understanding the generation of millennials can be perceived as a challenge in the workplace for CEOs as more and more youngsters and newbies start at their entry-level jobs.


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I was interviewing a young man for a pricing role last week. He seemed curious about the role. He was certainly not shy in telling me what he wanted:


1. a stimulating role

2. a great team

3. a qualified boss (which he explained meant someone that actually knew what they were doing – not just a CEO title)

4. career opportunities & pathways

5. title and status

6. and an extremely high salary & incentives package.


I thought to myself, with that kind of chutzpah, I want to see what this guy could do, and invited him to Taylor Wells online pricing & commercial manager assessment platform.



He went through the initial online screening promptly and with relative ease. He scored pretty well and showed potential for pricing. But this candidate would need some pricing skills development and management guidance to be successful in this role.


Apart from that, he was overpricing himself in the market somewhat. But overall, he was a good candidate and we continued the conversation.


We met to discuss his assessment results and the role in more detail. He was very keen to learn where and how he could improve his skills. He took the feedback well – great signs.


When we started to discuss the role and business in more detail, however, I noticed a distinct change in his demeanour and energy levels.


He took out the client’s job description again; looked at it for a few seconds and furrowed his brow.


I thought this is unusual behaviour, most people right now would love to be in his position and have the opportunity to work in a leading organisation. Wouldn’t they?


I started to wonder: Why the change in behaviour?


Is he only here to get some free insights into his personal development? Is he really interested in getting a job?



Understanding Gen-X and Millennials in the Workplace


I was taken aback. But I needed to look at his reaction differently. I went back through my notes for any clues he was giving me in our prior conversations that could help me understand this situation better.


There were…


  • Culture

He had friends in the hiring organisation who said the business was slow-moving and management heavy.


  • Annual report

He read their annual reports and was completely aware of a decline in business performance & profitability.


  • Industry

He mentioned how online platforms were ‘smashing’ traditional business models & cheaper overseas competitors are taking large chunks of market share with low ball prices.


  • Team structure

He asked about the team structure. There were multi-layers of management. Then, he asked me whether he would be able to make decisions in the business.


  • Job description

As we talked about the job, he was curious and engaged. But then he switched off when I sent him the client’s job description.


  • Technology

He asked about what technology the business was using. He questioned why they were not automating basic tasks when they could easily be automated.


  • Business model

He asked about changing consumer preferences impacting the business model. A key concern for the industry – and one with no easy answer.


I began to see the danger of attributing ‘hiring challenges’ and workforce engagement issues to generational forces – this young man was making some valid points irrespective of his age and upbringing.


I began to see how even saying millennials are a nightmare to hire helps us feel better.  In other words, ‘generational differences’ is a get-out clause allowing us to avoid answering difficult questions relating to business model disruption and workforce engagement issues such as workload, career development, sufficient financial reward, and meaningful work.


So, as a sales development executive, how do you lead millennials in the workplace? Millennials may appear to put themselves first, compared to other generations. And they often exude a “what’s in it for me?” mentality. But perhaps it’s not as simple or clear cut as that. To help us continue understanding millennials in the workplace, we need to be aware that:


  • Millennials are informed about business issues because they come from an era of modern technology. They have all the information at their fingertips.
  • do not fear asking difficult questions.
  • have aspirations to change the world.


Maybe the problem then is not generational difference, but a clash of values. Simon Sinek described millennials in the workplace as narcissistic, unfocused, lack patience, self-interested, and want to work with a purpose by focusing on making an impact.


What should you know when hiring millennials?


According to a recent workforce study, most CEOs do not really understand the needs of millennials.


That’s a problematic declaration when millennials represent 40% of the total workforce in 2020.


There may be clashes in values for Gen-X and millennials in the workplace, but there are ways of understanding how to lead these millennials in the workplace.


Addressing human capital challenges with flawed thinking and talent management approaches do not work.


Yet, increasing numbers of bosses claim millennials are a nightmare to employ, with 63% reporting that those in their 20s and early 30s require more guidance. Time and time again, reasons have been pointed to generational differences. Displeasing qualities of being lazy, entitled, privileged etc.


Understanding Millennials in the Workplace


Admittedly, the sense of privilege that exudes some millennials during a hiring process or at work can be really off-putting.


  • Should we be calling them out for being so connected to their values?
  • Are we simply feeling bad and reacting irrationally to their requests to be treated humanely?
  • Are we disappointed in ourselves for not living by our own values and standards?



Over the years, people have become desensitised to their surroundings. Likewise, we have moved from a mechanistic industrial revolution to an egalitarian platform revolution. We are expected to know how to feel and behave appropriately with this change, considering that there is relatively little help or guidance available.


We have long conditioned ourselves to keep our work and life separate and are now re-learning how to integrate our work and lives.


Unlearning the habits of old is not easy. This is true just as much as committing to a goal is vital and needs willpower.


Seeing someone display a courage of conviction can be confronting because it can cause dissonance. This means that our value systems and views on the world have collided with someone else view of the world – an unsettling learning experience.


I fit into the older generation category (i.e., pre-1982) and I know how much it goes against the grain to say ‘no’ to opportunities. Experiencing the late 1980’s and early 1990 recession stays in the mind of the older generation because we have lived through some of the worst jobs shortages since the Great depression in 1929.


Like all trauma, economic trauma stays with us albeit deep in our subconscious and manifests in various ways. Moreover, older generations tend to say “yes” when asked by the boss to take on extra projects, roles, and responsibility with little to no pay increase.


Millennials, on the other hand, tend to be much more vocal when a role does not meet their expectations or when they are given additional work. So, the fact that they put their personal values ahead of organisational goals isn’t surprising at all.


How to hire millennials into the business is a CEO’s priority. These days, the majority of CEOs looking to hire more people are either implementing “disruptive technology,” gearing the business for growth or defending a sinking ship.


From the latest trends, CEOs are either taking over smaller companies or hiring people with the right skills to align with the future of work and business.



Yet, there is a confluence of agendas occurring between young professionals and large, traditional businesses. To help CEOs and sales development executives in the process of understanding millennials, they need to know that:


  • Outdated recruitment and talent management processes are holding businesses back from finding the best people for the job.
  • Identifying underlying values, commitments and motivations are incredibly difficult, yet imperative to successful hiring.
  • Bringing the right collection of people together regardless of their age and/or generational differences will drive innovation and diversity of thinking.


Millennial employees and those who belong to Gen Y generally prefer remote and flexible working hours than a rigid Monday to Friday schedule. They do not look forward to working during holidays or weekends if the situation calls for meeting tight deadlines. They are forward-thinking, place more importance on education than experience, and are more likely to change jobs than Gen X-ers. When it comes to fostering work relationships, they lean towards a fun, innovative, and energetic work environment.


Gen X employees, on the other hand, independently perform well on tasks and roles that require minimal supervision. They do not favour frequent job changes, but they work to build stability and prepare for their retirement. Years of experience is mostly preceded by education from prestigious universities.


What’s the best way to achieve balance in the workplace environment? Sales development executives and the rest of the team should look beyond perceived differences in the workplace. That is to say, find creative ways to strengthen each other’s weaknesses and foster a culture of open communication and understanding. It has to be done in a manner that emphasises the skill sets that contribute to the company. Rather than magnify reasons that annoy or irritate you and other coworkers, create a healthy work environment competition instead. Lastly, provide coaching and innovative brainstorming opportunities for skill gaps to achieve common goals of the organisation.


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How to Lead in Understanding Millennials in the Workplace


It is likely that team management issues will be an ongoing challenge for individuals and businesses alike. As a senior sales executive, fixing these issues is part of the role and responsibilities.


This includes: team underperformance, bad hires, high staff turnover, missed opportunities, turf wars, stress, absenteeism and profit loss.


If you want to attract and retain the best talent for your pricing team, you need to face reality and start thinking radically different about the future of the work environment and how you hire talented people into the organisation.


Don’t address the issue by redesigning more interesting jobs or offering flexible hours. People want to be a part of something bigger no matter what generation they come from. A greater purpose in life coupled with Genuine leadership, role models that they can trust and believe in, and businesses that make a difference.


Every time a new generation enters the workplace, CEOs may think that it’s going to be a puzzle to manage and lead these newcomers. But in truth, we may come from different generations, grew up in environment and situations that may be unlike others, yet we seek very similar and universal purposes. We want to feel connected with others, know that our companies, bosses, and co-workers care about us, and make an impact fulfilling what we enjoy doing. We are a lot like other people. And frankly, most of us expect to be treated like people too! After all, there are more things that bind our common goals and aspirations. It’s in our DNA.


As a CEO, is your business set up to hire and retain millennials?


See our blog on overcoming stress in the revenue management community and why CEOs need to focus on the customer value proposition.

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