Things Leaders Do

Your Gen X Boss Decoder Ring: A Field Guide for Millennials and Gen Z

• Colby Morris

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Ever wondered why your Gen X boss seems to speak in code? Why they get weird when you ask "why" or seem obsessed with how many hours you work? This episode flips the script—giving Millennials and Gen Z the backstage pass to understanding what makes their Gen X bosses tick. It's not about excusing poor leadership; it's about cracking the code so you can work together more effectively.


What You'll Learn

  • The real reason Gen X leaders act the way they do (hint: it's not personal)
  • Why common Gen X behaviors that drive you crazy actually make perfect sense to them
  • Specific language and strategies to get better results from your Gen X boss
  • How understanding their "operating system" can turn friction into collaboration


Key Takeaways

"Your Gen X boss isn't trying to make your life difficult. They're just operating from a different instruction manual."

"When you start speaking their language, many Gen X leaders will actually start to evolve."


Who This Episode Is For

  • Millennials and Gen Z feeling frustrated with their Gen X managers
  • Anyone who's ever felt like they need a translator for their boss
  • People who want to build better relationships with senior leadership


Your Action This Week

Pick your Gen X boss's most confusing behavior and try one new approach based on what you learn in this episode.


Connect with Colby


Reflection Question

Which Gen X behavior have you been taking personally that might just be generational programming?



Speaker 1:

People First. Leadership, actionable strategies, real results this is Things Leaders Do with Colby Morris.

Speaker 2:

If you've ever wondered why your Gen X boss seems to speak in code, you're not wrong. We basically do. If you've ever thought, why does my manager expect me to read their mind, or why do they act like asking questions is a character flaw, well, buckle up. You're about to get the backstage pass to understanding your Gen X leader. Hey, leaders, I'm Colby Morris and this is Things Leaders Do, where we tackle real relationships, real leadership challenges with real solutions.

Speaker 2:

Today's episode is different. Instead of talking to Gen X leaders about what they're doing, right or wrong, I'm talking to, like everyone else, the millennials, gen Z, anyone who's ever felt like they need a translator to understand their Gen X boss. Think of this as your field guide to Gen X leaders, not to excuse their behavior, okay, but to help you understand what's driving it, so you can work with them more effectively and maybe even help them become better leaders in the process. Help them become better leaders in the process. So let's get into the Gen X origin story, or basically why we're like this. Before we dive into the decoder ring, you need to understand where Gen X leaders came from, because our leadership style isn't random. It is the direct result of how we grew up and learned to work. We're the latchkey kids who came home to empty houses and we literally had to figure things out on our own. We grew up during the corporate downsizing of the 80s and 90s. We watched our parents get laid off after decades of loyalty. We learned that job security was a myth and that you better be able to stand on your own two feet. We entered the workforce when the internet was still dial up. I mean you had to print out MapQuest directions and then work-life balance. That wasn't a phrase people used. We learned to work by watching leaders who believed in hierarchy, who thought emotions belonged at home and who measured dedication simply by the hours logged rather than really the outcomes that were achieved. So when your Gen X boss does something that seems really bizarre or outdated, remember they're not trying to be difficult. They're operating from a completely different playbook, one that was written when Blockbuster was still a viable business model.

Speaker 2:

Now let's break down the code. Decoder number one why do they want me to pay my dues? This is what it looks like. Your Gen X boss seems reluctant to give you literally any growth opportunities, better projects, promotions until you've been there for what feels like eternity. Right until you've been there for what feels like eternity, right? They use phrases like earn your stripes or put in your time, or when you've been here so long as Sarah has. Well, they might give the high visibility projects to someone who's been there two years instead of you, even though you have better skills for it. Here's what's really happening.

Speaker 2:

Gen X leaders learned that advancement came through endurance, not just performance. We literally had to wait our turn, sometimes for years, before we ever got any kind of meaningful opportunity. We were taught that shortcuts were cheating and that respect had to be earned through grinding it out. Why? Well, here's the backstory. We watched boomers climb the ladder slowly and we did the same. There was an unspoken rule you start at the bottom, you prove yourself through consistency over time and eventually, maybe you get rewarded. It wasn't about talent or potential. It was about persistence and proving you wouldn't quit when the things got tough. So here's how to work with this Don't fight the system, work within it strategically. And here's how to work with this Don't fight the system, work within it strategically. And here's how.

Speaker 2:

First, just have a direct conversation about growth expectations. I want you to ask something like this. I'm really interested in developing this role. Can you help me understand what success looks like here and what the typical timeline is for advancement looks like here and what the typical timeline is for advancement? Second, demonstrate consistency before asking for the opportunity. Okay, show up reliably, deliver quality work and stick around through a few challenging projects. Look, gen X bosses are watching to see if you're going to bail when the things get tough. And third, frame your growth requests in terms of value that you can provide. Say something like I'd love to take on more responsibility in client presentations because I think I can help us close deals faster with my background in their industry. Or, hey, I'm interested in leading the social media strategy because I have ideas that could increase our engagement rates based on what I'm seeing in the market. Remember, they're not trying to hold you back. They're trying to make sure you're ready for what comes next. All right, decoder number two why are they so uncomfortable with feelings? This is what it looks like. Your Gen X boss changes the subject when you bring up work-life balance. They seem awkward during emotional conversations or they respond to personal sharing with uncomfortable silence, followed by immediate task switching you mentioned you're stressed about a deadline or something and they just say, okay, well, let's focus on getting it done and move on. Or you share that you're having a tough time personally, and they respond with something like I'm sorry to hear that, and then immediately pivot to work topics. Here's what's really happening.

Speaker 2:

We were raised with a clear separation between work and personal life. Bringing emotions or personal challenges to the workplace, that was just seen as unprofessional. It was like wearing pajamas to a business meeting. You just didn't do it. Here's the backstory.

Speaker 2:

Gen X learned to compartmentalize like it was a survival skill. Well, let's be honest. It was a survival skill. Work was work, home was home. You didn't bring your problems to the office and you certainly didn't expect your boss to care about your feelings. We were taught that showing vulnerability was a sign of weakness and that emotional intelligence wasn't really intelligence at all. Really Think about it. We grew up watching our parents come home from work and not talk about their day beyond. It was fine. We learned that professional meant keeping a poker face, even when you were stressed, when you were overwhelmed or if you're dealing with personal challenges. Our role models were leaders who prided themselves on never letting anyone see them sweat. We were explicitly taught that bringing personal issues to work was unprofessional, having a bad day, suck it up Family problems, leave those at home Feeling burned out. That's not your boss's problem.

Speaker 2:

We learn to see emotional conversations at work as messy, inappropriate and, frankly, kind of selfish. So here's how to work with this. You can still have these conversations, you just need to approach them a little differently. Instead of leading with emotions, I want you to lead with impact. Instead of saying I'm feeling really stressed and overwhelmed, try something like I want to make sure I'm managing my workload effectively. Can we talk about priorities so I can deliver my best work? See what I did there. Instead of sharing personal struggles, directly, frame them in terms of work effectiveness. I've got some family stuff going on that might affect my schedule over the next few weeks. Here's how I'm planning to manage my responsibilities. You're not being less authentic. You're just learning to speak their language, and once you build trust through consistent performance, many Gen X leaders will actually become more comfortable with those conversations.

Speaker 2:

All right, decoder number three why don't they just tell me what they want? I've heard this one a lot. This is what it looks like when Gen X bosses give you vague instructions like handle the Johnson account or put something together for the board meeting, then they expect you to figure that out on your own. You know what handle means or what kind of something they want. When you come back with questions like what's the timeline or what format, are you thinking, they seem annoyed, like you should already know those things matter? You're thinking they seem annoyed, like you should already know those things? Well, here's what's really happening.

Speaker 2:

We learn through trial and error, usually with little or no guidance. We were expected to just figure it out and we did, or at least eventually we did. So we assume that you can too. It's not that we don't want to help. We genuinely believe that figuring out yourself is better for your development. Is that right? No, but that's where we came from. The backstory.

Speaker 2:

Gen X came up during the era of that whole sink or swim management. Our bosses just threw us in the deep end and expected us to learn by doing. We got minimal training, limited feedback and we were expected to be resourceful problem solvers. Typical onboarding was like hey, here's your desk, there's the coffee machine, you can figure out the rest. We learned to be scrappy, to research things ourselves, to try multiple approaches until something worked. When we couldn't figure something out. We were expected to exhaust our own resources before we ever asked for help.

Speaker 2:

Asking too many questions was seen as needy or actually seen as lazy, like you weren't trying hard enough to solve problems on your own. So when we see you asking lots of questions, our first thought is have you tried figuring this out first? We're not trying to be difficult. We genuinely believe that the struggle of figuring out yourself is what makes you better at your job. So here's how to work with this. Show your work before asking for help, instead of saying I don't know how to do this. Try something like hey, I've researched this and that approaches and I'm thinking this may actually be the best path forward. Does that align with what you're looking for or should I consider other options? Instead of asking open-ended questions like what do you want me to focus on? Try, based on our last conversations, I think these are the priorities and I should start with this one. Or would you like me to adjust this order? And I should start with this one? Or would you like me to adjust this order? This shows you're not being lazy or helpless. You're being strategic and you're confirming your thinking. Most Gen X bosses will respect this approach and they'll actually give you more guidance once they see you're actually doing the work. All right.

Speaker 2:

Decoder number four why is feedback so awkward and rare? This is what it looks like. You only hear from your Gen X boss when something's wrong. Positive feedback is rare and when it does happen it's usually brief and uncomfortable, like they're reading from a script. Performance conversations feel like a dental procedure. You finish a big project successfully and get maybe a good job in passing, but when you make a small mistake you get a detailed email about what went wrong. Here's what's really happening.

Speaker 2:

We grew up in a no news is good news culture. If you weren't getting yelled at, you were probably doing fine. We learned that feedback was mostly about correction, not development or encouragement. Here's the backstory. Gen X learned to work with minimal feedback Environments where praise was rare and criticism was the primary form of let's call it guidance. Our bosses operated on the assumption that if you were still employed, you were probably doing okay. Positive feedback was so uncommon that when it did happen, it usually felt fake or forced, at least like someone told them they had to say something nice.

Speaker 2:

We learned not to expect recognition for doing our job well. That was just expected. You got noticed when you screwed up, not when you succeeded. So we developed thick skin and learned to find our own motivation internally rather than seeking external validation, to find our own motivation internally rather than seeking external validation. Unfortunately, this also means we never learned how to give the kind of regular, meaningful feedback that actually helps people grow.

Speaker 2:

So how do you work with this? You're going to have to train them to give you feedback. Yes, seriously. Start by asking for specific feedback regularly. Hey, I just finished the Johnson project. What went well and what can I improve next time? Make it easy for them by asking targeted questions. I'm working on my presentation skills. How do you think I handled that client meeting today? When they do give you positive feedback, acknowledge it. Thanks. That's really helpful to know that I'm on track and then be patient. They are learning a new skill, we're learning a new skill and it's going to feel awkward for us at first, but most Gen Xers once they see how much it helps your performance, we'll get better at it.

Speaker 2:

All right, decoder number five why are they obsessed with hours worked? Yeah, I saw you roll your eyes. This is what it looks like. Your Gen X boss seems to equate time spent in the office with dedication, spent in the office with dedication. They notice when you leave at 5 pm and make comments like must be nice to keep banker's hours, or leaving early again. They seem suspicious of flexible work arrangements and might say things like I need to see that people are working, or question whether remote work is really productive at all. Here's what's really happening. We learned that commitment was measured by sacrifice. The harder you worked and the more you sacrificed, the more dedicated you were. It's not really about the hours. It's about what the hours represent to us. See, the back story is Gen X built their careers during an era when FaceTime mattered more than outcomes, when staying late was a visible sign of commitment and when work-life balance was something you figured out on your own time. If at all.

Speaker 2:

We proved our worth by being the first one in and the last one out. We sacrificed weekends and family time when projects demanded it. We learned that dedication wasn't just about what you produced. It was about how much you were willing to sacrifice to produce it. As messed up as that sounds, the leaders we admired were the ones who worked the longest hours, who were always available, who never seemed to take real vacations. We internalized the message that, if it works, it was important to you and it would consume most of your time and energy.

Speaker 2:

All right, so here's how to work with this. All right, so here's how to work with this. Focus on results, but acknowledge the effort behind them. Communicate your productivity, not just your schedule. No-transcript, simple. Be visible about your contributions. I know you noticed I left early yesterday for my doctor's appointment. I made sure to finish the client proposal first and I sent it to the team before I left. When you do work flexible hours, show the results. Hey, I did some work from home last night on the presentation and incorporated the feedback that you gave me. You're teaching them that productivity isn't about hours, it's about outcomes, but you need to make those outcomes visible. All right, our last decoder.

Speaker 2:

Why do they get weird when I ask why? This is what it looks like. When you ask why you're doing a task or a project, gen X bosses seem irritated, defensive, or they give you that dreaded because I said so response. They might say things like just focus on getting it done or you don't need to understand the whole strategy, just handle your piece. Sometimes they act like your questions are slowing everyone down or questioning their judgment. Here's what's really happening. We learn not to question authority. When our bosses gave us tasks, we just did them, no questions asked. So when you ask why, our first instinct is often to think you're questioning our judgment or just being difficult Doesn't mean it's right. That's just kind of the mindset.

Speaker 2:

The backstory is this Gen X learned in hierarchical environments where questioning or questioning up was seen as really insubordination or, at best, inefficiency. We were taught that good employees did what they were told, figured out the why on their own time and didn't slow down the process with questions. The chain of command was clear Leaders made decisions, workers executed them. Workers executed them. We learned that asking why could be interpreted as challenging authority or being difficult or not trusting leadership judgment. Our bosses expected us to just take assignments on faith and prove our competence through execution, not through understanding strategy. We were told that understanding the big picture was above our pay grade and that our job was to focus on our piece of the puzzle.

Speaker 2:

So how do you work with this? Well, frame your questions as seeking clarity, not really challenging authority. Instead of why are we doing this? Try, I want to make sure I understand the bigger picture so I can do this effectively. Can you help me understand how this connects to our main goals? Instead of this doesn't make sense. Try, I want to make sure I'm approaching this the right way. What's the most important outcome you're looking for? Or, instead of, why is this a priority? Try, can you help me understand the context so I know what to focus on? You're not changing what you're asking. You're changing how you're asking it, and that's what makes a difference. All right, your action plans for this week. Here's how to put this decoder ring to work. First, pick your Gen X boss's biggest quirk. Is it the pay your dues mentality?

Speaker 2:

the feedback, avoidance, the obsession with hours. Pick the one that frustrates you most and commit to trying a new approach this week. And second, have one strategic conversation. Use the language and framing I just gave you to just address one ongoing friction point. Remember, you're not trying to change them, you're trying to work more effectively together. And then, third, just document what works. When you try these new approaches, pay attention to what gets better.

Speaker 2:

Okay, gen X bosses are pretty consistent. Once you figure out their patterns. Look, I'm not asking you to excuse poor leadership or accept outdated management styles. If you've been listening to this podcast at all, you know that's not who I am. What I'm asking you to do is just try to understand where your Gen X boss is coming from so you can work together more effectively. The best part when you start speaking their language and working within their framework, many Gen X leaders will actually start to evolve. They'll see that you're competent, thoughtful, committed. They'll often become more flexible and supportive.

Speaker 2:

In response, your Gen X boss isn't trying to make your life difficult. Well, most of us are not trying to make your life difficult. They're just operating from a different instruction manual, one that was written when dollop internet was cutting edge technology. But now you've got the decoder ring, use it wisely. Here's my question for you which of these Gen X behaviors have you been taking personally that you realize now might just be generational programming? Hey, if this helped you understand your Gen X boss a little better, share it with someone else who's trying to crack this code.

Speaker 2:

And if you want more tools for navigating workplace relationships across generations, if you're looking for someone to help coach you or a keynote speaker, head over to nextstepadvisorscom that's N-X-T, no E nextstepadvisorscom. That's N-X-T, no E nextstepadvisorscom, and I'd love to help you out. Also, connect with me on LinkedIn. That link is in the show notes, as always. Thank you so much for listening to Things Leaders Do. I'm Colby Morris, helping you just try to build these bridges across the generations. Helping you just try to build these bridges across the generations. So go out there, lead better, understand, change your communication, try to be a better leader every day. And you know why?

Speaker 1:

Because those are the things that leaders do. Thank you for listening to Things Leaders Do. No-transcript.