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The Leadership Challenges of Modern-Day Management and How to Overcome Them

Updated: Apr 5




I write about workplace leadership in all its facets—effective interviewing and onboarding, performance management, leadership development, workplace ethics, the first-time manager, women in leadership, remote communication, common leadership challenges, and more.  And while I constantly try to focus on the “how” of things and keep things simple, there remains an underlying tension in any message that says that managers, executives, and business owners must remain excellent individual contributors while also assuming responsibility for the ”care and feeding” of their employees.


It can feel like a double standard when so many managers feel torn between constantly changing deliverables, speedy turnarounds, changing priorities, and so much more, while authors like me proclaim that leadership, communication, and teambuilding are the healthiest areas of focus as you build and scale your own career.  How did we get to this point of management feeling squeezed from above and below?  Why doesn’t “management” feel as impressive or inspiring as it used to in its own right?  And is it fair to ask corporate leaders to step beyond their own individual contributor priorities to shepherd those on their teams to new career heights by serving as mentors and coaches? 


The short answer is yes. While the challenges of current-day management remain ever present and can feel overwhelming at times, it’s important to gain perspective of what got us here in the first place.  With that 30,000-foot view understanding of our present-day challenges, you’ll gain an important perspective on how to move forward in your own career and become known as both an outstanding individual contributor and people leader and talent developer.


A 30-Year Lookback


Management’s current challenges are a direct result of global competition, new technologies, and a shift in the power, structures, and skills necessary or required to excel in today’s workplace. Looking at the following chronologically, we can map out key trends and movements that altered the frontline operational manager’s or senior executive’s roles and responsibilities in the evolving workplace.


·       Process Reengineering (1990s – early 2000s)


The movement to boost operational efficiencies and reduce redundancies led to outsourcing, offshoring, and the management need for leading larger teams with broader areas of responsibility.  As defined by Bain & Company, Business Process Reengineering or BPR is the radical redesign of business processes to achieve dramatic improvements in productivity, cycle times, quality, and employee and customer satisfaction.


BPR includes eliminating low-value work, automating repetitive tasks, rethinking basic organizational and people issues, and equally significantly, determining appropriate roles for third parties or outsourcers, focusing on where they might add value. If you remember the “McKinsey is coming to town” concern in the ‘90s and early 200os that drove fear into the hearts of managers across all spectrums of corporate America, you’re not alone. Downsizing and “rightsizing” often became the end result of such “consulting interventions” at the turn of the millennium.  The result: management positions were often eliminated, or the scope of managerial roles expanded significantly to cover more departments and people. Individual deliverables expanded as well, resulting in structural changes that continue to challenge those in leadership roles today.


·       Digitization (around 2010)


The 2010s were a decade of phenomenal innovation, led largely by the transition to mobile phones and the rise of data, which accelerated the growth of AI, e-commerce, social media, biotechnology, global finance, and so much more. Digitization held the potential to help organizations run more effectively and efficiently by increasing transparency and communication, improving decision-making, increasing productivity, and enhancing collaboration.


In reality, this decade of digital transformation and disruption also resulted in large-scale job displacement, increased competition, data security risks, and over-reliance on technology. Further, frontline operational leaders at all levels began to feel a loss of power, control, and status as they were no longer a critical part of the corporate information loop.


·       Agile Initiatives (mid-to-late 2010s)


Seen most often in management consulting firms and Big 4 accounting firms as well as certain traditional corporate settings, internal marketplaces were established across the entire organization to match skills to work and to rapidly assemble project teams on an as-needed basis. Internal teams could bid on business, form for a specific project or program, and deliver results on a targeted and well-defined basis. On the one hand, agile innovation methods have greatly increased success rates in software development, improved quality, and speed to market.


On the other hand, agile methodology thrives on flexibility, but without a clearly defined scope, it can be difficult to prioritize tasks and deliverables. Agile processes likewise put pressure on workers to produce as much as possible in the shortest amount of time. Likewise, due to rotating supervision of agile project teams, managers have experienced challenges communicating across organizational silos or with lack of accountability. As such, managers experienced the loss of power and authority involved in traditional management relationships.


·       Remote/Hybrid Work (March 2020 – present)


It’s hard to believe that remote and hybrid work really wasn’t on many organizations’ radar screens prior to the outbreak of the Covid-19 pandemic.  To be sure, a demand for greater work-life-family flexibility remained a core priority of Gen Y millennials and Gen Z Zoomers well before the Covid-19 outbreak. However, only a relatively small percentage of companies and workers practiced some form of consistent remote work, and that was often enjoyed only at the higher levels of leadership. The just-in-time technology of videoconferencing (think Zoom and Microsoft Teams) and Slack provided us the tools and resources we needed to keep the wheels on the bus turning—even when we weren’t physically onsite to provide our services.


And while remote and hybrid work may go a long way in providing the work-life-family control and equilibrium that so many generations wanted—including Gen X “Baby Busters” and the Baby Boomers themselves—it caused a sense of “productivity paranoia” among business owners and CEOs who felt that “managing the unseen” could lower productivity, lead to a drop in collaboration, teamwork, and culture, and worsen the isolation, loneliness, and depression of Gen-Z Zoomers (i.e., the 25-and-under crowd as of this writing). As a result, managers were now expected to cultivate empathetic relationships that would allow them to engage and retain the people they supervised, including the DEI (diversity, equity, and inclusion) and employee wellness and wellbeing initiatives that seemed to many to be almost “parent-like” in nature and overly demanding of their time and energy.


The New Landscape of Leadership


Yes, these movements have all had both positive and negative effects on the business landscape. There’s really nothing that can be done to undo or rewrite the recent history that leads us to today’s workplace realities. It’s likewise no coincidence that CEOs polled in the 2023 Deloitte Global CEO Outlook value collaboration, accountability, agility, emotional intelligence, and innovation highest among the leadership traits they need most to compete effectively in today’s challenging business climate.


Like most things in life, however, it comes down to having a healthy perspective and a willingness to adapt your mindset to what’s needed most in today’s business environment. No, you’re not being asked to be someone’s “parent” at work. And no—it’s not because the younger generations don’t want to work hard, appear entitled, or otherwise want the corner office by the time they’re thirty. (Be careful with that one. . . My father made similar complaints about my generation, and I’m a Baby Boomer!) 


In fact, these changing demands regarding “soft skills,” emotional intelligence, trust and respect in the workplace, and helping people do their best work every day with peace of mind should have been in place for the past hundred years.  They weren’t.  We’ve taken so much for granted. The Baby Boom, for example, began in 1946 at the end of World War II and ended eighteen years later in 1964 with the introduction of the birth control pill. 77 million babies were born over that 18-year period equating to 10,000 babies a day.  Now THAT’S a sizeable labor pool that fed the American economic boom as it emerged from the war and transitioned to a peace-time economy. Yet it lead us to assume that talent would always be available, regardless of how people were treated.


But something occurred in 2011 that got nary a line of commentary in the major newspapers or trades. . . The first Baby Boomers turned 65.  And for the next 18 years—from 2011 through 2029—ten thousand elders continue to move into retirement every day in our nation (and many other industrialized nations that experienced similar population booms at the end of the Second World War). To make matters worse, Gen X was roughly only half its size, and many Baby Boomers became part of the “Gray Resignation,” either retiring early or starting their own businesses rather than remaining in corporate America. That's where we find ourselves today.


Business owners and CEOs learned for the first time in March 2020 that their most important assets—their employees—went home every night and weren’t necessarily going to return the next day.  The labor scarcity that ensued and that still remains in place today to a significant degree demonstrates that relationship building, trust, respect, and motivation are required to keep employees coming back to the office, shop floor, or work site. Equally significant, to get “discretionary effort” out of those workers, interpersonal relationships with their immediate supervisors must be developed and nurtured. The two most important considerations in employee engagement remain (1) the relationship with the boss and (2) the learning curve.  Hence, the need for real-time feedback and structured professional development meetings in quarterly (rather than annual) performance reviews.


Is this too much to ask of any frontline manager or senior executive?  Possibly, depending on how you look at it. But a healthier perspective and mindset will tell you that these are the needs of today’s workers. Every generation faces unique pressures and challenges. This is ours.  And it’s not a bad thing. . . We’re not at war. We were able to tame a global pandemic and limit worldwide deaths to three million according to the World Health Organization—as opposed to 21 million from the “Spanish flu” a century earlier. And many of the social movements that feel like they’re rocking our world nowadays, like Me Too and Time's Up (gender), Black Lives Matter (race), Him Too (supporting male victims of sexual assault), He for She (gender equality), and Orange the World (ending violence against women and girls) are attempting to shed light on egregious societal practices that have been swept under the proverbial rug for far too long .


Embracing a True Leadership Mindset


Now is an excellent time to embrace Leadership 201—an opportunity to demonstrate selfless leadership, grow new talent, and become someone’s favorite boss. Understand that this is the demand of our day in the managerial workplace. We have an opportunity now to reinvent ourselves and our organizations, to create our own ecosystems for our teams and departments—regardless of the drama going on outside or above us. Give to others what you want for yourself: respect, trust, goodwill, and the benefit of the doubt.  Know that happy cows produce more milk, and create the right and certain circumstances for those under your leadership to motivate themselves and thrive.


It’s not above your pay grade to become an outstanding leader, someone who has your people’s backs and who encourages them to combine their personal and career interests with the work they do every day. Simply make the space for them to find their own traction at your company and in the business world as a whole.  When in doubt, err on the side of compassion. Laugh a bit more and come from a spirit of enlightenment where you literally lighten things up. Give people back to themselves. Despite the crisis and disruption we face every day, both in and outside the office, help your people do their best work every day with peace of mind. Make sure they know you have their backs. And know that the universe is nothing but a giant copying machine: it knows that you can’t give away anything that you don’t already have. Therefore, give generously. As the saying goes, what emanates from you returns to you. Make of your life a gift, whether that’s in a business or personal setting.


Now you have a better understanding of what’s taken us to the brink of exhaustion. Now you have a chronological perspective of the many changes you’ve had to endure that makes management and leadership seem like a ball and chain around your neck at times. But you likewise now see the wisdom of the bigger picture. You can appreciate that holding onto outdated notions of management no longer serves you well. And you have the tools necessary to master today’s greatest challenges in terms of people leadership and effective communication. Remember that life isn’t for getting, it’s for giving. What you want for yourself, give to another. Pay it forward. Then let the business world return those favors to you by allowing your leadership role to touch others’ lives and build their careers. There’s no greater gift that the workplace offers.


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