In an era of rapid globalization, agile organizations will outpace competitors by focusing on developing new managers. People are their only renewable capital, yet many companies have long struggled to prepare millennial leaders and incoming Gen Z talent for frontline roles.
While much has been written about identifying, developing, and retaining supervisory staff, most literature has focused on baby boomer and Generation X managers. As these groups retire, more millennials are entering frontline supervisory positions earlier than their predecessors. By 2025, millennials are projected to comprise 75% of the workforce (Timmes, 2022). Their effectiveness as managers will significantly impact organizations. Their role poses new critical challenges, as they oversee a multigenerational workforce that mixes Gen Z, older Gen X, and Baby Boomers who are still working. Developing this talent and utilizing it to its full potential will significantly impact the future of the business (Tabrizi, 2013).
Investment in leadership programs has soared since the early 2000s, exceeding $14 billion annually (Gurdjian et al., 2014a). Every year, organizations invest untold hours into identifying future leaders, creating leadership succession plans, and training leaders. Despite this, 60% of first-time managers fail within their first 24 months (Adler, 1996; Miller, 2017).
Without a healthy pipeline of high-potential managers to pull from for future senior-level leadership positions, there will be no one ready to replace a senior executive should there be an unexpected exit. How effective these millennials are as people managers will significantly impact their organizations.
Over the years, research has shown that the role of the frontline manager specifically (often also first-time people managers) plays a critical role in achieving an organization’s bottom line and business objectives (Hill, 2004). Companies are among the first to admit that they are falling short in developing leadership and that most programs fail to achieve their desired results.
This gap between investment and result has clear costs. Poor managers decrease productivity, engagement, and retention. Managerial ability accounts for 70% of team engagement; reports from underperforming managers perform 15% worse than those from high performers (Arruda, 2023). These employees are 20% likelier to disengage or leave (Adler, 1996).
Leadership development is crucial for identifying future leaders, creating leadership succession plans, and training leaders. Therefore, this study seeks to examine how organizations can enhance systems for selecting, developing, and retaining first-time millennial managers.
Literature Review
As stated earlier, this study aimed to improve organizational systems for selecting, promoting, and retaining first-time managers in the growing millennial supervisory population.
Consistent with this objective, an existing literature review provides a historical overview of emerging research on millennial and Gen Z staff, followed by an analysis of current organizational systems to identify, develop, and retain first-time managers.
Millennials (born 1981–1996) are the largest generation and, by 2025, are projected to make up 75% of the workforce. However, research on millennial managers is still limited. Existing literature mostly explores non-supervisory millennials’ work needs, values, and behaviors, as well as ways to motivate and retain them. Additionally, generational stereotypes create management challenges for Gen X and baby boomer supervisors, largely due to differences in values and work habits (Gabrielova & Buchko, 2021).
As research continues to evolve, studies are now exploring differences between millennials and Gen Zers, particularly as millennial managers increasingly oversee Gen Z employees. Prior studies found that managing millennials requires nontraditional approaches. Millennials favor collaborative managers, clear career paths, and greater face time with supervisors (Carpenter & de Charon, 2014). Their high expectations for advancement increase managerial demands. He concluded that to be effective, organizations must adapt to millennials’ collaborative preferences and manage their advancement expectations.
Hamori et al. (2015) investigated how to retain high-potential young managers by studying their work behaviors and experiences. They found a gap between what young professionals prioritize—such as mentoring, coaching, formal training, and support from managers—and what their jobs currently provide.
Gabrielova and Buchko (2021) compared generational values among millennials and Gen Z workers. Both prioritized achievement, professional development, frequent feedback, and work-life balance. However, Gen Z demonstrated greater risk aversion and competitiveness, while millennials were more risk-taking and collaborative, concluding that these differences could lead to increased workplace conflict. They highlighted the critical need for high-quality research on millennial managers as they take on their first supervisory roles, and emphasized training and how organizations can provide it.
Identifying Managerial Talent
Scholars agree that high-potential leaders should reflect business strategy. Organizations use competency frameworks to assess readiness, evaluate employees, provide a common language, and offer a clear succession-planning roadmap (Biscoe & Hall, 1999; Cantor, 2005; Crane, 2022; Groves, 2010). Competencies are “underlying characteristics causally related to effective or superior performance” (Biscoe & Hall, 1999, p. 37).
Beyond competencies, scholars increasingly stress mindset as a predictor of leadership potential (Crane, 2022; Hill, 2004). Mindset is “an established set of attitudes held by someone” (Dweck, 2005, p. 56). Groves (2020) found that today’s global landscape needs new leadership competencies and strengths. Thus, growth-minded candidates are most attractive as management prospects (Dweck, 2005).
Unfortunately, without clear frameworks, organizations use ineffective selection methods: hierarchy-based promotion, overpromoting productive individuals, or self-identification. Furthermore, research does not address whether such frameworks work for identifying millennial supervisory talent.
Developing Managerial Talent
Nearly 60% of first-time managers receive no pre-promotion training. Most supervisory staff development happens after promotion.
To remedy this, Plakhotnik (2017) proposed training aspiring managers beforehand to increase success. Similarly, Croteau and Wolk (2010) recommended pre-promotion training, including formal management training and coaching.
Hill (2004) found that stretch assignments—challenging roles in new areas or divisions—are most effective for pre-promotion development, helping millennials meet their ambitious career goals and focus on high-stakes roles. These assignments build skills as candidates set agendas and mobilize others. However, evidence for their effectiveness among millennial supervisors before promotion remains limited.
Leadership development best practices include action-learning projects, manager-led courses, multi-rater feedback, and formal training. Nevertheless, Action-learning projects, a widely used tool for leadership development, often fail due to insufficient reflection time, lack of post-program follow-up, and single-event limitations (Groves, 2007).
Hamori et al. (2015) found that millennials don’t value working on inherited problems for career advancement. While millennials’ individualistic tendencies may lead to rejection of authority, they simultaneously value ongoing professional development (Groves, 2007). This asset may be tapped to tailor manager-taught courses in which experienced managers instruct high-potential employees, reinforce the organizational learning culture, and develop both instructors and participants.
Multi-rater feedback, a common leadership development tool (Conger & Toegel, 2002), provides reliable, objective feedback and reduces defensiveness by broadening understanding of social roles across organizational levels. Given millennials’ preference for frequent, consistent feedback, this approach is promising for first-time millennial supervisors (Carpenter & de Charon, 2014; Gabrielova & Buchko, 2021). However, Conger and Toegel (2002) found that multi-source feedback is less effective when used only for appraisals or pay, rather than growth. It could challenge ambitious millennials, who may focus more on positive feedback for advancement than long-term structural development.
Management Training Programs
Organizations invest heavily in management training, a $14 billion industry. Yet, studies show these programs often fail. Common pitfalls include disconnects between theory and practice, focus on skills over mindset, reliance on off-site instruction, and limited evaluation (Groves, 2010; Gurdjian et al., 2014b).
Existing literature doesn’t address millennial-specific training. Millennials often need stronger emotional intelligence and soft skills to manage people, especially in office politics, leadership, and team building. As managers, they supervise Gen Z subordinates, who tend to have lower confidence, a greater fear of failure, more mental health issues, and less experience (Gabrielova & Buchko, 2021). These generational differences may shift the manager’s role. For example, Gen Z often lacks basic skills such as email writing and phone handling, underscoring the need for targeted guidance and training.
Retaining Managerial Talent
Transition Period
During their transition, first-time managers face new scenarios requiring new skills (Spreitzer et al., 1997). Historically, the grace period for new managers has shortened dramatically, from six months in the 1960s to only a few weeks in the 2000s (Plakhotnik, 2017). To address this compressed timeline, scholars advocate for structured transition periods with comprehensive training and gradual assignment of responsibilities (Croteau & Wolk, 2010; Plakhotnik, 2017). However, no formal research has specifically evaluated the effectiveness of the transition period for first-time millennial managers.
Culture of Support
Effective organizations recognize managerial development as a shared responsibility and reject the “sink-or-swim” mentality (Hill, 2004). First-time managers in supportive settings consistently perform better (Croteau & Wolk, 2010). Organizational culture decisively impacts development outcomes. A truly supportive culture treats first-time managers as essential to stability and succession, encourages learning at all levels, and eliminates the “sink-or-swim” approach through coordinated HR and training support before and after promotion.
Millennials’ prioritization of managerial support highlights a gap between their values and organizational practices. Manager-led courses allow more experienced managers to become teachers for newer managers. They provide a platform for managers of different levels to get together and discuss challenges (Gabrielova & Buchko, 2021).
Summary
As the literature reveals, research on systems that select, promote, and retain first-time managers’ organizational support is limited, especially regarding their interaction with the millennial supervisory population. More effort is needed to bridge the gap between theory and development practices to address their needs.
Methodology
Sampling process, measurement system, and data analysis procedures were used to investigate how organizational systems can better select, promote, and retain first-time millennial managers.
Method
A non-experimental, qualitative design (Creswell, 2014) was used to explore millennial supervisors’ unique lived experiences as first-time people managers. Qualitative research allows for detailed sharing of experiences, feelings, reactions, and opinions, enabling examination of multiple perspectives. In a challenging environment mixing Gen Z, Gen X, and Baby Boomers, it is crucial to underline that, consistent with the objective of the research dedicated to this specific segment of the workforce, surveys and responses rely on participant perspectives and may introduce bias.
Sampling
The target population was millennial employees in U.S. organizations who had been internally promoted to people manager roles within the past 5 years to ensure fresh perspectives on their transition experience. Purposive and convenience sampling were employed, with recruitment through former colleagues, social media, LinkedIn, classmates, and academic networks. A snowball sampling approach was used, with declining participants referring new participants and participants recommending others at the conclusion of the interview.
The final sample included 16 millennial individuals serving as people managers at the time of study or within five years prior. All participants were first-time managers promoted internally from individual contributor roles based on performance and organizational qualifications.
Measurement System
Qualitative data were collected through semi-structured Zoom interviews lasting approximately 1 hour.
The questions were divided into two parts. The first part included five multiple-choice questions to confirm participants met inclusion criteria (first-time millennial managers). It also captured information on organizational systems for selection, promotion, training, and transition, as well as the generational demographics of participants’ direct reports.
The second part had open-ended questions that explored participants’ unique experiences. Topics included expectations, challenges, team success, role perception, and self-assessment of managerial effectiveness. These questions, adapted from the literature review, let participants describe their experiences and explain their success or challenges as first-time managers. Interviews were transcribed using Otter.ai. Field notes were recorded. Each participant was assigned a code name, and all identifying information was removed from transcripts and field notes.
Analysis
Data were organized in Excel for analysis, verifying that field notes aligned with transcripts, and removing identifying information. Recurring themes related to the research question were identified, and the most prevalent were documented in a separate Excel sheet with supporting quotes and notes. A narrative passage was written to convey the findings, aiming to understand how to improve organizational systems that select, promote, and retain first-time managers for the growing millennial supervisory population.
Results
Results from 16 semi-structured, virtual interviews are presented. The first half of each interview included survey-style questions to capture generational demographics and assess organizational systems for promotion, training, and transition of first-time managers (Table 1). The second half consisted of open-ended questions that explored participants’ perceptions of their roles and effectiveness (Table 2).
Sample Demographics
Participants were identified as millennials born between 1981 and 1996, within five years of their first people-managing role. All but two were still in that role. This was their first time managing others. For 14 of 16, it was an internal promotion (Table 1). Two participants qualified despite not receiving an official internal promotion due to unique circumstances. Participants came from various business functions and industries, with staffing being the largest group (four).
Promotion and Role Transition
Nearly all participants (15/16) received direct reports immediately upon promotion. Seven began managing direct reports before the formal title change, with one stating they had already overseen people before becoming a manager. Another noted they received direct reports a month before their job switched over. One performed the role for a full year before receiving an official promotion.
Direct Report Generational Composition
Half of the participants’ direct reports were millennials. A new category, “Mixed With No Majority,” was created to accurately capture team generational diversity. Five participants reported teams with two to four generations, with no single generation predominating.
Formal Training and Development
Over half (9/16) received formal managerial training (before, after, or both). Seven had none, though one used self-elected online training and two received informal coaching.
Training type and content varied among those who received formal instruction. Descriptions included new manager cohort programs, required online training, shadowing experienced managers, and leadership development classes (Table 1). One participant received leadership development training before promotion, then online and informal training after. Two participants reported that training was not always relevant to their roles.
Role Expectations
Overall, no consistent themes emerged regarding training type or content.
There were no consistent themes around the expectation of a new manager; only whether it was communicated and how.
Specific expectations varied widely: sales targets (3), added responsibilities (2), transition or flexible periods (2), and job descriptions (2). Expectations were communicated verbally (7) or verbally and formally (3). Four participants received no consistent role expectations.
Team and Personal Success
Most participants (14/16) reported team success during their first 24 months, with their definition of success varying: direct reports’ baseline job performance (all), broader business impact (13), soft skills development (6), specific metrics (9), and direct report development (5).
14 participants reported personal success, with fewer expressing strong confidence. Only 5 described themselves as “very successful,” compared to 9 who rated their teams as “very successful.”
Nine participants noted overlap between their definition of managerial success and team success, and eight compared their performance against business expectations.
Four participants cited positive feedback as a success marker, while five participants’ definitions of success as a manager also included how “happy” their direct reports were.
Only two participants didn’t feel personally successful in their first 24 months as managers. They also said their teams weren’t successful. Their definitions of success depended on their teams’ success in their base jobs.
Five major themes and one sub-theme emerged from participants’ discussions of their biggest challenges as new managers in their first 24 months.
Theme 1: Managing Individual Differences.
Managing different personalities, learning styles, work ethics, and generations was a major challenge for six participants. One participant mentioned struggling to understand work ethics, as not everyone has the same output or product. Another participant described balancing underperforming employees without overburdening high performers. One participant consciously adjusted their communication style between a Gen Z direct report and an upper millennial direct report to account for generational differences in learning.
Theme 2: Managing Behavioral Challenges.
Six participants mentioned behavioral challenges from their supervisees. This theme focused on conflicts, disputes, and employee relations issues affecting performance. Challenges included direct reports failing to take direction, a lack of emotional maturity, disrespectful communication, and poor attitudes. One participant was frustrated with the inexperienced employees’ pushback and efforts to develop them. Another described managing emotional immaturity, including internal fights and tears, and challenging supervisees’ behaviors hindering promotion.
Generational demographics play a significant role in behavioral challenges among supervisees, as noted by all participants.
Varying value systems, work ethics, communication styles, and professionalism across generations contribute to these issues. Two participants criticized Gen Z, expressing confusion about their value system.
A team manager spanning all four generations faced the challenge of preventing Baby Boomer negativity from influencing younger employees.
Two participants who hadn’t previously mentioned generational challenges confirmed that younger employees, especially Gen Z and recent graduates, require more guidance on professional conduct. They reported increased violations of the dress code, tardiness, and informal written communication.
Navigating generational demographics within a team presents an additional challenge for new millennial supervisors already struggling with behavioral issues.
Theme 3: Remote Management.
Six participants identified remote or hybrid management as a significant challenge, further complicating the steep learning curve. One participant noted that remote work eliminated informal ambient awareness, as co-location allowed for overhearing conversations and understanding the team’s dynamics. Another described the difficulty of onboarding remote employees, as learning occurs in-person, and remote work hinders quick adaptation and brand establishment. A third noted that transitioning to remote management requires a fundamentally different approach. Participants collectively described remote management as affecting team communication, accessibility, and accountability.
Theme 4: Access to Mentorship and Managerial Support.
Mentoring challenges emerged during discussions. Six participants had direct managers for advice, finding it helpful. Three noted that their managers were unhelpful; two of them were unsuccessful as managers and had teams struggling within 24 months. Both said greater support would’ve improved their outcomes. One shared, “Not having a direct supervisor to support me was the biggest challenge.” The other described losing access to a supportive manager mid-role: “I never felt supported after my former manager left…When I moved [to the new manager], the person I was reporting to wouldn’t respond.”
The unsuccessful participant who found success despite an unhelpful manager sought external guidance. Participants with strong managerial support described it as instrumental, with one noting, “I had three people to go to for any support I needed…Sometimes I’d ask the same question to all three and get three great perspectives.”
Theme 5: Insufficient Formal Training.
Eight participants believed formal training could have made them more successful in the role. Interestingly, over half (n = 9) received formal training before or after their promotion, though some questioned its real-world relevance. One participant said the “in-office training doesn’t reflect what’s out there in the field.” Half (n = 8) thought more training on administrative tasks like payroll, documentation, and performance reviews would be most useful. One participant said they lacked training in payroll and performance reviews, despite being given guidance. They also felt expectations were unmet, but no one explained how to do them. Participants consistently described a steep learning curve regarding these foundational but expected responsibilities.
Summary
Three key findings emerged from this study on generational demographics and first-time millennial managers. First, most millennial managers oversaw either other millennials or mixed-generational teams with two to four generations. Second, managing such diversity posed challenges, including differences in values, work ethic, communication styles, and professionalism. Third, remote management introduced additional complexity, influencing employee onboarding, team communication, and accountability.
In light of these findings, the study aimed to improve organizational systems for selecting, promoting, and retaining first-time millennial managers. While literature supported the view that generational differences pose challenges, research on this issue remains limited.
The study identified three distinct ways managing differs for first-time millennial managers: overseeing multigenerational teams, navigating generation-specific behavioral issues, and managing remotely. While these factors don’t necessarily impede success, they present added challenges in the current workforce.
Discussion and Interpretation
First-time millennial managers typically oversee predominantly millennial or mixed-generation teams. Having four generations present has only existed since 2019, when the first Gen Zers entered the workforce.
Study participants identified distinct generational differences in value systems, work ethic, communication styles, and professionalism. Some actively researched these differences, while others expressed frustration managing cohorts with different values and norms. Recognizing and respecting these differences can strengthen team dynamics, but unaddressed differences risk frustration, dysfunction, conflict, and attrition.
Managing a diverse generational workforce also leads to behavioral issues. What one cohort deemed acceptable behavior varied significantly by their generational demographic. While managers address behavioral issues, this study suggests an upward trend in generation-specific tensions, reduced emotional maturity among younger cohorts, and less formal communication from Gen Z. Notably, when confronted with aggressive behavior from baby boomers, younger employees or mentors were typically sought rather than direct confrontation. This suggests that first-time managers lack training in effective negative behavior management.
Unresolved conflict consumes time and attention, potentially compromising other supervisory responsibilities and contributing to disengagement and team dysfunction. Better preparation and training before assuming management roles could mitigate these challenges.
Recommendations for Practice
Organizations can address emerging challenges by leveraging existing processes: diversity and inclusion initiatives, management training, mentorship programs, and remote management best practices.
First, organizations must avoid stereotyping different generations. Instead, use generational demographics, such as personality assessments, to better understand behaviors and improve communication and professional skills. Personality assessments have been used by professionals as a tool to better understand their own behaviors and the behavior of those around them and to improve their communication and professional skills.
Integrating generational awareness into broader D&I programs supports new, first-time managers. Organizations with such cultures foster a growth mindset and provide a broader social safety net for millennials in this role.
Organizations can also address the multi-generational challenge by including training on generational demographics in new manager training. This approach establishes a common organizational language around generational dynamics.
Organizations should provide targeted training on difficult conversations, conflict resolution, HR policy documentation, and escalation procedures to address behavioral issues identified by five participants. Scenario-based training with role-playing exercises can develop real-time management skills. Since half of the participants believed more training would enhance their success, organizations should intentionally address topics such as payroll, documentation, and performance reviews, where current training is often brief or ineffective.
Post-COVID, remote and hybrid work is common. New managers need to learn to manage remotely effectively. Organizations must help them build these capabilities.
Successful new managers often have mentors or someone they can seek advice from. Organizations with cultures that support first-time managers achieve better outcomes. Formal mentorship programs can provide reliable guidance and support (Plakhotnik, 2017).
While study participants reported success despite unique generational challenges and limited preparation, further investigation is warranted.
Implications for Future Research
A larger study focused on millennial managers’ selection and management of different generations could provide valuable information. Research is also needed on organizational resources addressing this challenge and their positive impact. The study suggests no real change is necessary, as most managers reported success using different criteria.
Additionally, successful managers are linked to mentorship. Previous research exists on this subject (Bergelson, 2014), but future studies could explore this relationship in more detail, particularly for first-time millennial managers overseeing baby boomers, Gen Xers, and Gen Zers.
Limitations
This study has several limitations. First, the sample was built from my personal and professional networks, with most participants known to me. While efforts were made to control information sharing, one participant may have learned about the study’s focus through a co-worker who had already participated. Second, non-standardized follow-up questions introduced interpretive bias, despite efforts to minimize researcher influence. Third, the study focused exclusively on millennial managers, so it didn’t examine whether the challenges they noted could be compared with those of other first-time managers across different demographics, which could provide a more comprehensive picture of the dynamics of the workforce. Fourth, it didn’t comprehensively document participants’ onboarding processes, potentially missing organizational resources that weren’t captured by the structured questions. Finally, all but two participants reported success as first-time managers, despite industry failure rates exceeding 50% (Miller, 2017). The sampling process may have oversampled successful managers, making it difficult to determine which challenges hindered success. There was no data on how organizations could better retain millennial managers.
Conclusion
First-time millennial managers face unique, time-intensive challenges: managing multigenerational teams with understudied dynamics, addressing generation-specific behavioral issues, and adapting to remote work environments. These challenges are significant because frontline managers drive team engagement and organizational outcomes. Behavioral issues can compromise other critical responsibilities and impede role success. Despite these obstacles, most study participants succeeded in their roles, though they experienced considerable frustration navigating these compounded demands.
This study aimed to improve organizational systems for selecting, promoting, and retaining first-time managers as the millennial supervisory population grows. The survey results suggest an upward trend in generation-specific tensions, reduced emotional maturity among younger cohorts, and less formal communication from Gen Z. Recognizing and respecting these differences can strengthen team dynamics. Formal mentorship programs can provide reliable guidance and support. While generational shifts pose challenges, participant success was not hindered, and their attention to teamwork demonstrated a unique opportunity that organizations could benefit from. Furthermore, remote management—a common post-COVID challenge—presents an additional difficulty, though it is not insurmountable.
Therefore, it would be prudent for organizations aiming to stay agile and remain competitive in today’s business world to increase developmental practices that match employee needs when training new managers for success.