Coaching Across Generations: Why One Size Never Fits All

Issue 230, September 18, 2025

Over the past two weeks, we have focused on executive burnout, exploring why, in today’s complex business environment, executives are considering alternatives to management strategies to regain mental equilibrium. Leaders are also innovating ways to manage a workforce to reduce the mental drain of today’s management pressures.

We conclude this three-part series with an exploration of how to coach a multi-generational workforce. As always, the human factor is the key to ensuring change and transformation success. Coaching your workforce (not bossing them to death) is important for their mental health and ongoing career growth for all generations – as well as yours!

Let’s explore multi-generational coaching and how the human factor imprints management dynamics.

Generational Differences in Coaching Receptivity 

The shift toward coaching leadership isn’t just a response to current executive cognitive overload challenges—it’s essential preparation for the workforce of today and tomorrow. We have often written about the five-generation dynamic playing out across organizational structures. Each generation comes with its views, values, opinions and, of course, its receptivity to leadership and management styles and constructs.

Research by the Center for Creative Leadership reveals significant generational variations:

• Gen Z employees often embrace coaching, expecting mentorship and development
• Millennials typically respond well once they understand coaching isn’t an evaluation or judgment
• Gen X may initially resist, preferring clear directives and independence
• Baby boomers often view coaching questions as inefficient or a lack of experience
• Alphas are emerging as entrants to the workforce and our first Gen AI; coaching them will be a novel experience

Coaching and Gen Z 

Younger employees live in a cross-border and borderless world via gaming, social and the internet. Leaders need to be sensitive to these worldviews to make adaptations in their management style and approach, ensuring they are prepared to manage a cohort of globally aware digital natives. These next-gen workers are also aligned with causes and deeply want a purpose. With the aspiration of Gen Z to rise to middle management, they need special coaching strategies.

Generation Z (born 1997-2012) entered the workforce with fundamentally different expectations about leadership and development. Unlike previous generations who often accepted the concept of working hard with the expectation that “paying their dues” will lead to promotion and success, Gen Z expects a faster career track with ongoing mentorship, regular feedback, and clear development paths from day one. As we have often warned, if you don’t give them a seat at your table, they’ll take on anyway.

Coaching Gen Z requires both finesse and patience. They are hard workers but need a clear description of what managers expect with ongoing dialogue and progress reports. Research by Deloitte shows that 83% of Gen Z workers consider learning and development opportunities when choosing employers. They seek out skill acquisition, not just to improve their current work quality, but also to enhance their resumes and offerings to future employers with their career portfolios. They want alignment to purpose, they lack long-term organizational, even brand loyalty, and they want to be coached and mentored. Leaders who master coaching will have a significant advantage in attracting and retaining a Gen-Z talent pool.

Here is a topline Gen-Z Coaching Playbook:

• Frequent touchpoints: Gen Z prefers frequent coaching conversations over annual reviews
• Career development focus: They want leaders who help them envision, understand, and work toward future roles, whether that is in the current or a future organization
• Purpose-driven coaching: They need help connecting daily tasks to larger organizational missions
• Technology integration: They expect coaching to incorporate the use of digital tools and platforms in environments that match their comfort zone.
• Socialization: Gen Z’s deficit of social skills and mental health issues caused by the fallout from the pandemic and obsession with communication on screen, not in person, begs for multiple channels of coaching to strengthen communication, meet their of-the-moment needs and improve physical and digital organizational social skills

Coaching Temporary Workers

In 2022, McKinsey’s research discovered 36% of the workforce were contingent workers, including freelancers, contractors and temporary employees. By 2027, analysts predict that 40% of the workforce will be contingent workers. Depending on the source of data, the Bureau of Labor Statistics in 2024 reported 6.9 million contingent workers in the US, and private source data reported up to 75 million contingent workers comprising the workforce. In any case, it is a trend that is here to stay. As a leader and manager, you may be growing your contingent workforce and finding it challenging to adapt and lead those non-full-time employees.

A gig worker comes to an organization with a different set of expectations and needs. This cohort requires coaching approaches that connect with their situations, and leaders managing hybrid teams of permanent and temporary workers need to coach accordingly.

There are specific coaching challenges with gig workers who have made commitments to your organization but can have their attention in more than one place at a time.

• Compressed onboarding: Traditional coaching relationships have the luxury of time to develop trust and understanding; part-time workers are on a more compressed schedule and often are focused specifically on a set of tasks or deliverables.
• Divided loyalties: Gig workers may prioritize multiple clients over deep organizational commitment; their ability to juggle affinities may be interpreted as a lack of commitment opposed to simply identifying with the role that they are in.
• Knowledge transfer: How do you coach for organizational knowledge when workers have limited tenure? How do you decide what information is critical to share for the work to be successful? Is knowledge needed to build the skills of the gig worker?

Here are ways to adapt coaching strategies to bring temporary workers up to speed and engender loyalty and commitment, ensuring the work is high quality and meets its objectives.

• Intensive early coaching: Front-load relationship building and expectation setting, recognizing that from the start, there is likely a contract that structures the relationship and the resulting work.
• Project-based development: Focus coaching on specific deliverable improvements rather than long-term career development. Ensure timely and appropriate feedback on work progress and work products.
• Peer coaching networks: Connect gig workers with permanent team members for ongoing support to help learn the lay of the land, communication preferences, and how work is accomplished within the organization.
• Documentation: Create coaching resources that can be quickly accessed and applied, ensuring they are noted in either the contract or statement of work and referenced in interactions.

Coaching in an Increasingly AI-Infused Workplace

As artificial intelligence handles more routine tasks and decisions, human expertise will evolve to focus on AI output validation, edge case identification, and complex decisions requiring contextual understanding, all skills that require sophisticated coaching.  This higher-level shift will also require a different level of communication and coaching for the human workforce.

In an AI-human workplace, leaders will help serve as a bridge between automation and the unique skills and capabilities of team members. Coaches, first and foremost, must understand the AI tools at hand and how to deploy them most effectively. Where are these tools most successful, where can they be trusted, where are they accurate, and where must human oversight and an output framework be established? The dynamic changes underway across today and tomorrow’s organizational construct will require both well-versed knowledge and understanding of when to rely on automated recommendations vs. human judgment. Workers, regardless of their generational identity or employment status, will need coaching and guidance.

Evolving how the workforce is managed and coached must embrace developing the uniquely human skills of emotional intelligence, creative problem-solving, and ethical reasoning. Coaching in this automated-hybrid environment should be centered on maintaining the human connection, preserving and strengthening interpersonal skills in increasingly digital workplaces.

When Your Team Resists Coaching Leadership

The transition from boss to coach rarely happens smoothly. Both leaders and team members may resist this fundamental shift, often for very human deeply rooted psychological and practical reasons. Understanding and addressing this resistance is crucial for a successful shift.

The “Just tell me what to do” phenomenon really exists. You might find that many of your team or department members want to be directed. Many employees have been conditioned to expect direct instruction, particularly in work environments of command-and-control structures. When leaders suddenly start asking questions instead of providing answers, team members may interpret this as a lack of leadership clarity, unwillingness to make decisions, and testing or evaluation rather than support. Employees may feel anxiety when they are asked to increase their participation from a manager they view as an expert. Their anxiety about being tested or set up can be coached away by establishing a safe environment where failure is tolerated when it is used as a learning experience.

One of our team members recently shared a real-life example of an entire team that seemed to know how to solve a problem they were facing but didn’t want to take action. They didn’t feel empowered to move the ball forward, nor did they feel they had permission to innovate or even change the process.

It’s interesting to reflect on and ponder what happened. Is it a lack of confidence? Insecurity? The result of a command-and-control leadership/management structure? Or could it be that the team wanted and needed a different working environment than what they traditionally experienced? If their leadership and management adapted their approach to coaching, the team would grow, learn and improve their confidence and skills. This is an example of a major lost opportunity.

Anticipating team resistance with strategies helps smooth the way for a coaching leadership shift:

1. Explain the transition explicitly: “I’m shifting my approach to help you develop problem-solving skills. This means I’ll ask more questions to help you think through solutions.”
2. Start with willing participants: Identify team members who are naturally curious or ambitious. Success with early adopters creates positive momentum.
3. Provide safety nets: “Let’s work through this together. If you get stuck, we’ll problem-solve as a team.”
4. Address the efficiency concern: “This might take a few extra minutes now, but it will save us both hours in the future when you can handle similar situations independently.”

When You Resist Coaching 

The perfectionist’s dilemma describes how high-achieving executives often resist coaching because they fear others’ mistakes will reflect poorly on their leadership. This perfectionism creates a paradox: the very drive that made them successful as individual contributors can sabotage their effectiveness as leaders. Many executives secretly fear that coaching will expose their own knowledge gaps. If they can’t provide immediate answers, what value do they add? This fear often stems from misunderstanding the leader’s role in complex organizations.

Building coaching confidence can be systematically trained through a four-step process:

1. Start with your strengths: Begin coaching in areas where you feel most confident and knowledgeable
2. Embrace “I don’t know:” Model intellectual humility. “That’s a great question. How might we find out together?” In this simple shift, you are empowering your reports to open up and help determine the solution.
3. Focus on process, not content: Your value lies in helping others think through problems, not in having all the answers
4. Track small wins: Document instances where coaching prevented future problems or developed team capabilities, ensure small wins are reiterated in team and individual interactions to ensure the environment of permission continues.

You Don’t Have to Know Everything

There is another fundamental insight to ease the process of shifting from boss to coach that may make the transition less stressful.  You don’t have to be an expert in everything. If you think of pro football, the head coach is the decision maker, controls his staff and is overall in charge of the team. He sees the big picture and calls the game. But he also knows his limitations and depends on five to six trusted assistant coaches who are all knowledge specialists, teachers and trainers. They are experts in defense and offense and, by position. This structure addresses the complexity of a team and strengthens its competitive edge. This may be a little unrealistic for a workplace, but the concept is that leaders have trusted deputies (assistant coaches) who fill any gaps they may have.

The Progress Report by Digital Entrepreneur supports this assistant coach strategy by suggesting: Stop trying to be good at everything. The report includes a process to help systematically “identify your edge, then fire yourself from the stuff that’s not working for you.” We have amplified the five-step journey to help alleviate the stress of trying to be perfect:

1. Audit what you do: List out the 8–10 things you do most often in your business. For each task, give it two scores on a 1–5 scale: Energy: Does this give you energy or drain it? Impact: Does this directly move your business forward? Multiply those numbers and call this your Edge Score. The tasks with the highest scores are your superpowers. The lowest-scoring tasks should be systematically weeded out of your time.
2. Write your edge statement Fill in this sentence: “The most valuable thing I do is ___. When I spend time on ___, the business moves because ___.” If you don’t know this off by heart, let your Edge Scores tell you which tasks are most valuable to you and to the business.
3. Protect your edge: Open your calendar and block one hour next week for your highest-scoring activity.
4. Fire yourself: Pick the task with the lowest Edge Score. Eliminate it by delegating, automating, or dropping it entirely. If the task is important and you have a team, delegate it. Most repetitive tasks can be automated with tools you already have. Get rid of low-scoring tasks that don’t drive outcomes. Even if you have the time for them right now, they’re unnecessary energy sinks.
5. Measure what matters: Track these three things for the next two weeks: edge hours this week; low-value tasks removed, and concrete outcomes from focusing on your edge. The goal is to drive your business forward and let you enjoy your job.

The Compound Effect: Winning Through Others

When you develop problem-solvers instead of problem-bringers, you’re not just improving team performance—you’re reclaiming your mental bandwidth for strategic thinking, innovation, and the high-level work that truly requires your expertise. Like the best sports coaches, effective business leaders understand that their success is measured not by their individual performance, but by how well they develop their team’s collective capabilities. Everything becomes a teachable moment. The results become a series of wins that inspire the team with motivation and increased engagement. As organizations become more complex and interconnected, the leaders who thrive will be those who can multiply their impact through others. The alternative—trying to maintain control over an ever-expanding scope of responsibilities—is simply unsustainable. Ultimately, instilling trust through coaching isn’t just good leadership—it’s fundamental to developing your team members and decreasing your own day-to-day mental burdens.

What’s your coaching experience been? Contact us anytime!

Miss the Other Issues in this Series?

From Boss to Coach: A Strategy for Executive Burnout

Issue 229, September 11, 2025

As we kick off the Fall 2025 sports season, it’s an opportune moment to examine a fundamental shift that can help lighten leaders’ burnout: pivoting from boss to coach. Successful athletic coaches don’t play every position themselves – instead, they develop each player’s individual skills to strengthen the team overall. Similarly, leaders can’t know everything, but they can empower others to contribute their expertise to collective success.

The Mental Overload of Modern Leadership: Why Today’s Executives Are Burning Out Differently

Issue 228, September 4, 2025

Productivity solutions are creating productivity problems. Consultants preach “work-life balance,” and executives install meditation apps and block calendar time for “strategic thinking.” Relaxation tactics aside, many successful leaders are quietly admitting something ominous: They’ve never worked longer hours, and they’ve never felt more cognitively exhausted.

How to Manage a Five-Generation Workforce (2021)

We are at an interesting inflection point: Five different generations make up today’s workforce: Gen Z, millennials, Gen X, boomers and the Silent Generation. And the Alphas are not far behind. Add to the age differences, the new rules of diversity and inclusion, changes in life stage definitions, individual and group values, and the impact of evolving societal events. For starters, 2020 Pew Research reveals 59% of Gen Zers say forms or online profiles should include additional gender options, compared with 50% of millennials, 40% of Gen Xers, 37% of boomers and 32% in the Silent Generation.

Connect with Us

What stories are shaping your organization’s biggest decisions right now? We’d love to hear your insights. Share your experiences with us on our Substack or join the conversation on our LinkedIn. For more insights on navigating transformation in today’s complex business environment, explore our archive of “Ideas and Innovations” newsletters or pick up a copy of The Truth About Transformation.

The Truth About Transformation: Why Most Change Initiatives Fail (And How Yours Can Succeed)

Why do 70% of organizational transformations fail?

The brutal truth: It’s not about strategy, technology, or resources. Organizations fail because they fundamentally misunderstand what drives change—the human factor.

While leaders obsess over digital tools, process improvements, and operational efficiency, they’re missing the most critical element: the psychological, behavioral, and cultural dynamics that actually determine whether transformation takes hold or crashes and burns.

The 2040 Framework reveals what really works:

• Why your workforce unconsciously sabotages change (and how to prevent it)
• The hidden biases that derail even the best-laid transformation plans
• How to build psychological safety that accelerates rather than impedes progress
• The difference between performative change and transformative change that sticks

This isn’t theory—it’s a battle-tested playbook. We’ve compiled real-world insights from organizations of all sizes, revealing the elements that comprise genuine change. Through provocative case studies, you’ll see exactly how transformations derail—and more importantly, how to ensure yours doesn’t.

What makes this different: While most change management books focus on process and tools, The Truth About Transformation tackles the messy, complex, utterly human reality of organizational change. You’ll discover why honoring, respecting, and acknowledging the human factor isn’t just nice—it’s the difference between transformation and expensive reorganization.

Perfect for: CEOs, change leaders, consultants, and anyone tired of watching transformation initiatives fizzle out despite massive investment.

Now available in paperback—because real transformation requires real understanding.

Order your copy today and discover why the human factor is your transformation’s secret weapon (or its biggest threat).

Ready to stop failing at change? Your organization’s future depends on getting this right.