Sticking Points by Haydn Shaw How to Get 5 Generations Working Together
What's it about?
Sticking Points (2013) explores what happens when up to five generations work side by side. It shows how shared goals at work are often undermined by everyday misunderstandings rooted in different generational experiences, habits, and expectations. The central message is practical and optimistic: these tensions are normal, manageable, and solvable when we learn how to work with differences instead of fighting them.
You've probably been in this meeting. Someone's checking their phone. Someone else looks annoyed. One person wants to talk it through. Another just wants the follow-up email. Everyone leaves irritated.
This kind of friction shows up everywhere at work: it’s present in debates about remote work, feedback styles, meeting length, dress codes, loyalty, and technology. It can feel personal, even when it’s not. But this isn't a case of the devil being in the details. The real driver is something much bigger—and much newer.
For the first time, workplaces include people who grew up before television, people shaped by email, people raised on social media, and people who have never known life without a smartphone. They all want to do good work. They all want respect, clarity, and purpose. They just go about it in different ways.
That gap creates daily frustrations that add up. Younger employees feel dismissed or slowed down while their older counterparts feel ignored or pushed aside. Managers are stuck in the middle, trying to keep everyone productive without picking sides.
The first bit of good news? These problems are predictable. They show up in the same places, time and again. Once you start spotting them, they become easier to manage. That's the second bit of good news.
This lesson digs into generational tension and shows how small shifts in flexibility, understanding, and leadership can ease the friction and get people working together. Most importantly, it offers a way out of the generational blame game and a template for organizations that want to accommodate and nurture everyone who works there.
For most of human history, families and workplaces (which were often one and the same thing) ran on a simple rule: you waited your turn. Authority and assets moved slowly from old to young, usually when someone stepped aside or died. That rhythm made sense in a world of farms, land, and livestock, where change crawled and roles stayed stable for decades.
That world, though, is gone. We now live in societies and work in organizations in which up to five generations rub shoulders. That’s new. So is the friction that comes with it.
Longer lives are the first pressure point. A century ago, careers ended around fifty. Today, people often hit their stride at that age. Leadership seats stay occupied longer, which means younger colleagues are often asked to wait until midlife before gaining real influence. Ambition, in short, now frequently collides with longevity. Many younger people worry that good things don't necessarily come to those who wait.
The second pressure point is speed. Information moves at a pace that compresses generations and new tools and ideas reshape work every few years. It’s not unusual for someone in their twenties to master systems that didn’t exist when their manager was trained. A junior analyst can pull data on a phone that used to be restricted to executive briefings. Access invites challenge from every direction. The diffusion of knowledge undermines old hierarchies where age and authority once coincided.
The third shift is cultural. The youngest four generations were raised as consumers: they were taught to question, compare, and expect choice. Many grew up with parents who prized independent thinking over obedience. That mindset walks straight into the workplace. People want a voice early, feedback often, and work that feels engaging rather than dutiful.
Faced with this reality, organizations tend to stumble into two unhelpful responses. The first is trying to ignore differences. The second is trying to force one generation to behave like another – a surefire way of wasting energy and fuelling resentment. People rarely enjoy being improved against their will.
What actually works is leadership, not correction. That starts with curiosity about how work looks from another age group’s point of view. It continues with conversation, negotiation, and shared problem solving. Change is coming either way. Change is coming either way. As we'll see in this lesson, smart teams decide how much to welcome, learn to translate across age lines, and keep moving together instead of pulling apart.
Once teams accept that different generations bring different habits and expectations, the obvious question becomes how much to adapt. Training is an easy place to start. Some people want a room, a trainer, and a printed workbook. Others want a short video they can replay between meetings. Organizations have argued about this for years as if one option must win. The real requirement is simpler: people must learn the skill well enough to use it. Offer more than one way to learn, check that it works, and stop fighting about the format.
This way of thinking applies far beyond training. Not every rule should bend, but many more can than most leaders assume. The key is knowing which ones matter. A real business necessity protects safety, customers, money, or funding. If ignoring a rule gets someone hurt, drives customers away, or damages revenue, it matters. If ignoring it mainly irritates someone in charge, it probably doesn’t.
Dress codes make this distinction easy to grasp. In a factory, open shoes can cause injuries. In a hospital, they raise hygiene risks. In food service, they can turn customers off instantly. In those settings, footwear rules protect people and profits. Move into a spa or a relaxed client environment, and the same rule can quietly work against you. A spa known for great pedicures gains nothing by banning sandals for staff. In that setting, the rule reflects habit rather than strategy, and habit is an expensive thing to defend.
Trouble shows up when leaders cling to preferences because they feel familiar. Running things your way feels satisfying, but watching younger employees disengage or leave doesn't. Many organizations are surprised to discover that insisting on comfort over flexibility costs them talent, energy, and momentum. Younger employees notice the mismatch quickly. Some comply without enthusiasm; others walk.
Of course, flexibility doesn’t mean giving everyone whatever they want. It means choosing deliberately. Keep the rules that protect what matters. Question the ones that exist mainly because someone once liked them. Remember, many policies outlive the conditions that created them.
Handled well, this approach unlocks the real advantage of multi-generational teams: each age group brings its own strengths. Younger employees, for example, often bring speed and new tools. Older employees bring judgment and perspective When those strengths combine, weaknesses soften. Research consistently shows that teams made up of different ages cooperate better and get more done. Leadership is about arranging people so the work wins. That only happens when flexibility serves the business rather than personal taste.
Few things cause more friction across generations than how messages are sent, received, and judged. Every age group shares the same need: people want enough information to do their job well and to feel included and respected. But each generation has its own communication style that feels natural. Those preferences are shaped by the tools people grew up with, often long before they entered the workforce.
Older generations built trust through letters, memos, meetings, and phone calls. Information came from experts, and conversation rewarded patience and focus. Many still value eye contact and uninterrupted discussion. The next wave – Gen X – grew up with television, where stories mattered more than credentials and messages came in short bursts. When it arrived in everyday life, email became their workhorse, with phone or video reserved for sensitive conversations.
Then came millennials and Gen Z – two generations raised on the internet, feeds, and constant interaction. They expect conversation, not broadcast. They want to comment, respond, and be part of the exchange. Social tools feel normal, but only when there’s real engagement. Posting without interaction feels pointless. The youngest of these employees grew up mobile first. Images, speed, and clean design feel essential. They text constantly yet often prefer email at work because it feels clear and documented. They know their comfort zones and also recognize where they need practice, especially with in person conversations.
Flexibility matters here, but it has limits. The test stays the same. If communication choices affect customers, safety, or revenue, they’re business decisions. Customer preferences always win. If clients expect a call, you call. If they expect a quick message or a video chat, you adapt. The same logic applies to recruiting and retention. Convenience can be the difference between engagement and opt out.
Good teams flex both ways. Older colleagues experiment with new tools while younger ones slow down, listen, and learn the unwritten history that never shows up in a message thread. Those stories carry context, warnings, and hard-earned insight.
The takeaway here is that every communication style has built-in strengths and blind spots. New tools boost speed and access, but they also distract. Experienced voices often spot risks early, especially around focus and overload. The goal isn’t to pick a winner but to learn each other’s language and choose the right one for the conversation you’re in at that particular moment.
We’ve seen how communication works better when teams learn each other’s language. That same logic applies to knowledge, especially as more experienced employees edge closer to retirement while still shaping daily work. The risk isn’t abstract. Many organizations worry about what happens when long serving staff finally step away, taking decades of insight with them.
This anxiety makes sense. Large numbers of older workers will keep retiring through the next decade, even as many remain active employees or customers. Workplaces will continue to include four or five generations at once. Knowledge transfer can’t wait. It has to start now.
Here's the sticking point: older employees often don't like writing things down, while younger employees want the knowledge but struggle with long face-to-face stories. Both sides feel frustrated unless the tension gets named openly. The best way to split the difference? Start with the shared need. Everyone needs information to do good work. The disagreement lies in how that information should travel. Older generations learned through listening and observation, with knowledge living in people rather than documents. Generation X mixed storytelling with written guides. Millennials and Gen Z grew up searching, watching, and replaying, so video feels natural. Written instructions work best when they’re short and searchable.
Flexibility becomes a business necessity here. The organization must keep its knowledge, but the method can change. Forcing experienced staff to write everything down rarely works. Expecting younger employees to absorb long unstructured stories rarely works either. Age bias makes this harder. Older workers are often underestimated despite strong performance in roles requiring judgment and people skills. When their contribution feels dismissed, valuable insight stays locked away.
The practical solution is to match strengths. If younger employees learn through video and older employees like to explain and demonstrate, record experienced staff walking through real tasks. Keep it informal. Edit later. Transcribe when needed. Even a phone camera is enough to begin.
Knowledge transfer doesn’t need to be complicated. Capture what people know in formats that suit them. Do it early and often. The payoff is continuity, confidence, and teams that keep learning instead of starting over.
Knowledge flows best when teams respect how different generations learn and share what they know. That same awareness matters in meetings where generational habits collide in real time. Few routines expose differences faster than putting a group in a room and asking them to talk.
Meetings stir strong feelings because each generation holds a different idea of what good participation looks like. Some leaders enjoy meetings and see them as the heart of teamwork; others see them as an obstacle between them and real work. Older team members may read typing or texting as disengagement. Younger ones may see it as multitasking while listening closely. Both sides believe they are being reasonable.
Banning devices rarely fixes the problem: it just shifts frustration from screens to eye rolls. The real issue usually sits underneath. Each generation suspects the others are the reason meetings drag on. Long verbal updates feel respectful to some. To others, they feel like information that could have been shared in writing.
Simple changes help. Replace round robin status reports with short written updates sent ahead of time. Use meeting time for decisions, debate, and problem solving. Set clear goals at the start, then relax if the conversation moves in loops rather than straight lines. Younger thinkers often connect ideas in non-linear ways. That isn’t disorder – it’s another way of making sense.
The most important ingredient isn’t perfect structure, but safety. Meetings work best when people feel free to ask questions, admit confusion, and speak without fear. Teams do better when everyone has room to contribute and leaders notice who has gone quiet and invite them back in.
Flexibility cuts both ways. Younger employees can limit multitasking when it distracts others. Older employees can question routines that exist only because they always have. Shorter meetings, clearer agendas, and more prep done online usually please everyone.
Remember, generational tension rarely comes from bad intent. It comes from shared needs met in different ways. Five generations at work doesn’t have to be a problem. When differences are understood and welcomed, it can be a resource.
In this lesson to Sticking Points by Haydn Shaw, you’ve learned that five generations now work side by side, creating predictable friction in everyday work. People share the same needs for respect, clarity, and purpose, but meet those needs differently. Problems surface around rules, communication, meetings, and knowledge sharing, all when preferences harden into norms. Teams can make progress by naming differences, flexing where possible, and protecting real business needs. Leaders get better results by encouraging dialogue, sharing strengths across ages, and designing work that helps everyone contribute.
Sticking Points (2013) explores what happens when up to five generations work side by side. It shows how shared goals at work are often undermined by everyday misunderstandings rooted in different generational experiences, habits, and expectations. The central message is practical and optimistic: these tensions are normal, manageable, and solvable when we learn how to work with differences instead of fighting them.
You've probably been in this meeting. Someone's checking their phone. Someone else looks annoyed. One person wants to talk it through. Another just wants the follow-up email. Everyone leaves irritated.
This kind of friction shows up everywhere at work: it’s present in debates about remote work, feedback styles, meeting length, dress codes, loyalty, and technology. It can feel personal, even when it’s not. But this isn't a case of the devil being in the details. The real driver is something much bigger—and much newer.
For the first time, workplaces include people who grew up before television, people shaped by email, people raised on social media, and people who have never known life without a smartphone. They all want to do good work. They all want respect, clarity, and purpose. They just go about it in different ways.
That gap creates daily frustrations that add up. Younger employees feel dismissed or slowed down while their older counterparts feel ignored or pushed aside. Managers are stuck in the middle, trying to keep everyone productive without picking sides.
The first bit of good news? These problems are predictable. They show up in the same places, time and again. Once you start spotting them, they become easier to manage. That's the second bit of good news.
This lesson digs into generational tension and shows how small shifts in flexibility, understanding, and leadership can ease the friction and get people working together. Most importantly, it offers a way out of the generational blame game and a template for organizations that want to accommodate and nurture everyone who works there.
For most of human history, families and workplaces (which were often one and the same thing) ran on a simple rule: you waited your turn. Authority and assets moved slowly from old to young, usually when someone stepped aside or died. That rhythm made sense in a world of farms, land, and livestock, where change crawled and roles stayed stable for decades.
That world, though, is gone. We now live in societies and work in organizations in which up to five generations rub shoulders. That’s new. So is the friction that comes with it.
Longer lives are the first pressure point. A century ago, careers ended around fifty. Today, people often hit their stride at that age. Leadership seats stay occupied longer, which means younger colleagues are often asked to wait until midlife before gaining real influence. Ambition, in short, now frequently collides with longevity. Many younger people worry that good things don't necessarily come to those who wait.
The second pressure point is speed. Information moves at a pace that compresses generations and new tools and ideas reshape work every few years. It’s not unusual for someone in their twenties to master systems that didn’t exist when their manager was trained. A junior analyst can pull data on a phone that used to be restricted to executive briefings. Access invites challenge from every direction. The diffusion of knowledge undermines old hierarchies where age and authority once coincided.
The third shift is cultural. The youngest four generations were raised as consumers: they were taught to question, compare, and expect choice. Many grew up with parents who prized independent thinking over obedience. That mindset walks straight into the workplace. People want a voice early, feedback often, and work that feels engaging rather than dutiful.
Faced with this reality, organizations tend to stumble into two unhelpful responses. The first is trying to ignore differences. The second is trying to force one generation to behave like another – a surefire way of wasting energy and fuelling resentment. People rarely enjoy being improved against their will.
What actually works is leadership, not correction. That starts with curiosity about how work looks from another age group’s point of view. It continues with conversation, negotiation, and shared problem solving. Change is coming either way. Change is coming either way. As we'll see in this lesson, smart teams decide how much to welcome, learn to translate across age lines, and keep moving together instead of pulling apart.
Once teams accept that different generations bring different habits and expectations, the obvious question becomes how much to adapt. Training is an easy place to start. Some people want a room, a trainer, and a printed workbook. Others want a short video they can replay between meetings. Organizations have argued about this for years as if one option must win. The real requirement is simpler: people must learn the skill well enough to use it. Offer more than one way to learn, check that it works, and stop fighting about the format.
This way of thinking applies far beyond training. Not every rule should bend, but many more can than most leaders assume. The key is knowing which ones matter. A real business necessity protects safety, customers, money, or funding. If ignoring a rule gets someone hurt, drives customers away, or damages revenue, it matters. If ignoring it mainly irritates someone in charge, it probably doesn’t.
Dress codes make this distinction easy to grasp. In a factory, open shoes can cause injuries. In a hospital, they raise hygiene risks. In food service, they can turn customers off instantly. In those settings, footwear rules protect people and profits. Move into a spa or a relaxed client environment, and the same rule can quietly work against you. A spa known for great pedicures gains nothing by banning sandals for staff. In that setting, the rule reflects habit rather than strategy, and habit is an expensive thing to defend.
Trouble shows up when leaders cling to preferences because they feel familiar. Running things your way feels satisfying, but watching younger employees disengage or leave doesn't. Many organizations are surprised to discover that insisting on comfort over flexibility costs them talent, energy, and momentum. Younger employees notice the mismatch quickly. Some comply without enthusiasm; others walk.
Of course, flexibility doesn’t mean giving everyone whatever they want. It means choosing deliberately. Keep the rules that protect what matters. Question the ones that exist mainly because someone once liked them. Remember, many policies outlive the conditions that created them.
Handled well, this approach unlocks the real advantage of multi-generational teams: each age group brings its own strengths. Younger employees, for example, often bring speed and new tools. Older employees bring judgment and perspective When those strengths combine, weaknesses soften. Research consistently shows that teams made up of different ages cooperate better and get more done. Leadership is about arranging people so the work wins. That only happens when flexibility serves the business rather than personal taste.
Few things cause more friction across generations than how messages are sent, received, and judged. Every age group shares the same need: people want enough information to do their job well and to feel included and respected. But each generation has its own communication style that feels natural. Those preferences are shaped by the tools people grew up with, often long before they entered the workforce.
Older generations built trust through letters, memos, meetings, and phone calls. Information came from experts, and conversation rewarded patience and focus. Many still value eye contact and uninterrupted discussion. The next wave – Gen X – grew up with television, where stories mattered more than credentials and messages came in short bursts. When it arrived in everyday life, email became their workhorse, with phone or video reserved for sensitive conversations.
Then came millennials and Gen Z – two generations raised on the internet, feeds, and constant interaction. They expect conversation, not broadcast. They want to comment, respond, and be part of the exchange. Social tools feel normal, but only when there’s real engagement. Posting without interaction feels pointless. The youngest of these employees grew up mobile first. Images, speed, and clean design feel essential. They text constantly yet often prefer email at work because it feels clear and documented. They know their comfort zones and also recognize where they need practice, especially with in person conversations.
Flexibility matters here, but it has limits. The test stays the same. If communication choices affect customers, safety, or revenue, they’re business decisions. Customer preferences always win. If clients expect a call, you call. If they expect a quick message or a video chat, you adapt. The same logic applies to recruiting and retention. Convenience can be the difference between engagement and opt out.
Good teams flex both ways. Older colleagues experiment with new tools while younger ones slow down, listen, and learn the unwritten history that never shows up in a message thread. Those stories carry context, warnings, and hard-earned insight.
The takeaway here is that every communication style has built-in strengths and blind spots. New tools boost speed and access, but they also distract. Experienced voices often spot risks early, especially around focus and overload. The goal isn’t to pick a winner but to learn each other’s language and choose the right one for the conversation you’re in at that particular moment.
We’ve seen how communication works better when teams learn each other’s language. That same logic applies to knowledge, especially as more experienced employees edge closer to retirement while still shaping daily work. The risk isn’t abstract. Many organizations worry about what happens when long serving staff finally step away, taking decades of insight with them.
This anxiety makes sense. Large numbers of older workers will keep retiring through the next decade, even as many remain active employees or customers. Workplaces will continue to include four or five generations at once. Knowledge transfer can’t wait. It has to start now.
Here's the sticking point: older employees often don't like writing things down, while younger employees want the knowledge but struggle with long face-to-face stories. Both sides feel frustrated unless the tension gets named openly. The best way to split the difference? Start with the shared need. Everyone needs information to do good work. The disagreement lies in how that information should travel. Older generations learned through listening and observation, with knowledge living in people rather than documents. Generation X mixed storytelling with written guides. Millennials and Gen Z grew up searching, watching, and replaying, so video feels natural. Written instructions work best when they’re short and searchable.
Flexibility becomes a business necessity here. The organization must keep its knowledge, but the method can change. Forcing experienced staff to write everything down rarely works. Expecting younger employees to absorb long unstructured stories rarely works either. Age bias makes this harder. Older workers are often underestimated despite strong performance in roles requiring judgment and people skills. When their contribution feels dismissed, valuable insight stays locked away.
The practical solution is to match strengths. If younger employees learn through video and older employees like to explain and demonstrate, record experienced staff walking through real tasks. Keep it informal. Edit later. Transcribe when needed. Even a phone camera is enough to begin.
Knowledge transfer doesn’t need to be complicated. Capture what people know in formats that suit them. Do it early and often. The payoff is continuity, confidence, and teams that keep learning instead of starting over.
Knowledge flows best when teams respect how different generations learn and share what they know. That same awareness matters in meetings where generational habits collide in real time. Few routines expose differences faster than putting a group in a room and asking them to talk.
Meetings stir strong feelings because each generation holds a different idea of what good participation looks like. Some leaders enjoy meetings and see them as the heart of teamwork; others see them as an obstacle between them and real work. Older team members may read typing or texting as disengagement. Younger ones may see it as multitasking while listening closely. Both sides believe they are being reasonable.
Banning devices rarely fixes the problem: it just shifts frustration from screens to eye rolls. The real issue usually sits underneath. Each generation suspects the others are the reason meetings drag on. Long verbal updates feel respectful to some. To others, they feel like information that could have been shared in writing.
Simple changes help. Replace round robin status reports with short written updates sent ahead of time. Use meeting time for decisions, debate, and problem solving. Set clear goals at the start, then relax if the conversation moves in loops rather than straight lines. Younger thinkers often connect ideas in non-linear ways. That isn’t disorder – it’s another way of making sense.
The most important ingredient isn’t perfect structure, but safety. Meetings work best when people feel free to ask questions, admit confusion, and speak without fear. Teams do better when everyone has room to contribute and leaders notice who has gone quiet and invite them back in.
Flexibility cuts both ways. Younger employees can limit multitasking when it distracts others. Older employees can question routines that exist only because they always have. Shorter meetings, clearer agendas, and more prep done online usually please everyone.
Remember, generational tension rarely comes from bad intent. It comes from shared needs met in different ways. Five generations at work doesn’t have to be a problem. When differences are understood and welcomed, it can be a resource.
In this lesson to Sticking Points by Haydn Shaw, you’ve learned that five generations now work side by side, creating predictable friction in everyday work. People share the same needs for respect, clarity, and purpose, but meet those needs differently. Problems surface around rules, communication, meetings, and knowledge sharing, all when preferences harden into norms. Teams can make progress by naming differences, flexing where possible, and protecting real business needs. Leaders get better results by encouraging dialogue, sharing strengths across ages, and designing work that helps everyone contribute.
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