Generational shifts in leadership are coming, with Gen X taking over from Boomers and Millennials rising quickly. With each group having its quirks and strengths, the future of work and corporate culture will be unlike anything we have seen before.
There is nothing like the slow drip of time when you are waiting for something to happen – just ask any child when they become aware their birthday is coming up. The same thing happens in the corporate world, except it’s even slower and you don’t get a party at the end. It’s also doubly painful knowing that the future is unkind to those who rush it.
Instead of dreaming of being a member of the Pinky and the Brain cabal, let’s imagine a future, 10 years from now, and explore what leadership could look like. Believe it or not, tomorrow’s leaders are already here today – they are next door to you or sitting in your office right now.
To do this, we’ll explore generational attributes, but with executive power. Because this topic is pretty wide, I asked Perplexity.AI to take a pass at the corporate strengths and weaknesses of each generation.
| Generation | Key Strengths | Key Weaknesses |
|---|---|---|
| Boomers 2025: (61-79) 2035: (71-89) | Loyalty, work ethic, team orientation, long-term view | Resistance to change, workaholic, hierarchical mindset |
| Gen X 2025: (45-60) 2035: (55-70) | Adaptability, tech competence, independence, experience | Under-recognition, disengagement, communication gaps |
| Millennials 2025: (29-44) 2035: (39-54) | Digital fluency, passion, adaptability, concise communication | Short attention span, authenticity over conformity, critical thinking gaps |
Please note that the following uses broad characterizations of generational groups for ideation purposes.
In 10 years, the Baby Boomer generation will be out of the workforce. While it’s tempting to discuss how their generational attributes contributed to workplace culture, let’s just focus on the fact that it’s the Boomer generation that will pick their Generation X successors. Based on human behavior, it’s likely that they will choose people that are like them in strengths and unlike them in how they have overcome weaknesses.
Generation X Leaders
The first tranche of leaders will be long-term employees who have a healthy appreciation for authority and hierarchies.
Leadership Style
Different from the team orientation mindset of Boomers, Gen X leaders will not seek as much consensus when making decisions. Since they are adaptable, they are more likely to pivot from bad ideas when necessary, unlike the rigid approach held by Boomers. This also means they are more willing to take calculated risks.
Gen X leaders will have progressed up the hierarchy by demonstrating high competence in their area. As such, they will seek to build highly competent teams around them. There will still be a strong emphasis on promoting talent based on experience and merit as Gen X leaders will seek those that mirror their independent thinking and hard-work ethic.
Culture
Gen X leaders will be model examples of culture champions. Having experienced under-recognition, micromanagement or a lack of appreciation, they can now create a thriving company culture where everyone feels engaged. In addition, their resourcefulness will drive engagement in parts of the company that have been previously considered challenging.
Their openness to use technology, especially AI, will create better connections with their employees as they will use digital (audio or video) channels more frequently to communicate transparently.
Gen X leaders will also likely have Millennial direct reports. While there may be gaps in communication styles across generations, Gen X will adjust as the younger segment of Gen X rises to leadership.
Business Operations
Generation X leaders will retain a dedication to work, but less so than the previous generation. As such, hybrid and/or remote work flexibilities will remain, if not expand, during the tenure of Gen X leaders. As independence and resourcefulness is highly valued, there can also be a desire to reduce the number of business processes and delegate more authority down the corporate hierarchy.
The days of status meetings, dashboards and report building will be at an end as the independent nature of Gen X leaders will prefer to self-serve the information they need. This will greatly increase with the pervasive use of AI and instant notifications to inform leaders of pressing issues.
Millennial Leaders
In some cases, there may be Millennial executives, but for the most part, this generation will be the first line of direct reports to Gen X executives. As they progress up the hierarchy, however, there will be some noticeable differences between Millennials and their predecessors.
Leadership Style
Unlike Gen X, Millennial leaders likely ascended using a lattice model versus a ladder. The desire to multi-task and explore new areas have made job mobility a key part of their success. This has also made them a jack of all trades, master of none. While this previously could have been a negative, the broad expertise supplemented by Artificial Intelligence will mitigate most concerns.
With shorter attention spans, Millennial leaders will need a team to help realize their vision. Shorter attention spans also mean a reduced focus on long-term, or detailed planning. To compensate, leaders will rely, or over rely, on AI or a Chief of Staff, to assist them with critical thinking or strategy development.
Culture
Culture is very important for Millennial leaders as they prefer passion and authenticity over authority. This energy will permeate into their organizations with broad adoption and potential pushback as the growing majority Gen Z employees seek to establish boundaries between work and their personal lives.
With the full embrace of digital messaging technologies, Millennial leaders will be accustomed to instantaneous notifications and communication. Familiar text messaging habits will be integrated into a corporate setting, making communications concise, direct, informal and frequent.
Business Processes
With a broad use of technology and desire for purposeful work, Millennial leaders will be the most receptive to fully remote work locations, minimizing the use of corporate offices. In addition to flex locations, flex work hours are possible to enable multi-tasking at work and in employees’ personal lives. Adopting the work-life model seen in European companies will be a possibility, although it will not be seriously considered until Gen Z leaders come into power.
The emphasis on multi-tasking in professional and personal settings will demand individual empowerment, therefore decision-making will be pushed out to where the information lies. This, in turn, will flatten the traditional corporate hierarchy.
At this point, there will be broad acceptance of the CAUSE model and the author will receive a Nobel Prize in the form of a million dollar gift card to Starbucks, allowing him the purchase of one tall café mocha.
All kidding aside, the point of this exercise was to think about what this means to you today. Should you run out the clock with current leaders before bringing up bold ideas? How could these potential leadership mindsets change what you do? What does the mean for the future of work?
Sometimes it’s easier to focus technology, rather than on the leaders that will be using it. Either way, the future is here, so now’s the time to start brushing up on Hans and Franz or other cultural references, because knowing is half the battle…
Twistymind 
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