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August 5, 2025 17 mins

Ever get frustrated trying to lead someone who sends emails in lowercase with no punctuation... but somehow they're your top performer? If you're a Gen X leader, you're sandwiched between generations with completely different values and expectations. In this episode, Colby breaks down why leading younger generations feels so challenging—and gives you practical strategies to bridge the gap without losing your edge.


What You'll Learn

  • Why your frustration with younger employees isn't really about them (it's about conflicting operating systems)
  • How to use Simon Sinek's "Why First" framework to create genuine buy-in
  • The 5 biggest mistakes Gen X leaders make with Millennials and Gen Z (and what to do instead)
  • What younger generations are really looking for from leadership (hint: it's not ping pong tables)
  • A practical 3-step action plan you can implement this week


Key Takeaways

The Real Issue: The tension between generations isn't about entitlement or work ethic—it's about fundamentally different experiences that shaped different expectations.

Start With Why: Before explaining what needs to be done, explain why it matters. Connect every task to a bigger purpose.

The Four C's: Younger generations want Clarity, Consistency, Coaching, and Care from their leaders.

Your Weekly Action Items:

  1. Audit your leadership mindset—where are you still leading like it's 1999?
  2. Practice the "Why First" framework on one delegation this week
  3. Ask one team member: "What's one thing we could change to make your work more meaningful?"


Episode Quotes

"That frustration you feel when they ask 'why' isn't about their entitlement. It's about your discomfort with a different way of working."

"The question isn't whether you should adapt. The question is: what's it costing you not to?"

"EQ isn't soft—it's the hardest skill to master and the most important one for results."


Resources Mentioned

  • Simon Sinek's Golden Circle (Why-How-What framework)
  • Things Leaders Do One-on-One Series (previous episodes)
  • Visit nxtstepadvisors.com for more leadership tools


Connect with Colby


Reflection Question

What belief about leadership are you holding onto that might be holding your team back?

Things Leaders Do is hosted by Colby Morris, helping leaders create clarity, build cultures people want to be part of, and lead with purpose.


Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
You ever get frustrated trying to lead
someone who sends emails inlowercase, with no punctuation,
but somehow they're your topperformer?
Or maybe you've got that Gen Zemployee who's incredibly sharp
but turns off Slack at 4.59 pmwith zero guilt?
Leading across generationsisn't new, but if you're a Gen X

(00:26):
like me, it's more complex thanever.
See, we're sandwiched betweenboomers who value loyalty and
grit, and younger generationswho expect flexibility, purpose
and emotional intelligence.
Hey, leaders, I'm ColbybyMorris, and this is Things
Leaders Do, where we tackle realleadership challenges with real

(00:50):
solutions.
Today, we're diving into one ofthe biggest challenges that I
think Gen X leaders face how tolead younger generations without
losing your mind or your edge.
Let's just call it like it isLeading millennials and Gen Z
can be frustrating.

(01:12):
You show up early, stay late andstill feel like you need to
prove yourself.
Meanwhile, zayden, your27-year-old team member, wants
to talk about work-life balanceand vulnerability and questions
whether we really need that 8 ammeeting.
Here's what I've learned afterworking with hundreds of Gen X

(01:34):
leaders through this exactchallenge.
The frustration isn't reallyabout them, it's about us.
Think about it.
We were shaped by completelydifferent forces.
Gen X grew up independent,skeptical, self-sufficient.
We were latchkey kids whofigured things out on our own.

(01:54):
We didn't get participationtrophies and we definitely
didn't expect to love our jobs.
Work was work.
You showed up, did your thingand you went home.
That experience made usincredibly gritty and resilient,
but it also made us guarded.

(02:15):
We learned to keep our headsdown, prove ourselves through
output, not to ask too manyquestions.
Millennials and Gen Z they grewup differently.
They were coached, mentored,encouraged to speak up.
They expect collaboration,feedback and flexibility.
They want to know not just whatto do but why it matters.

(02:40):
So that tension you feel, it'sthe collision of two completely
different operating systems.
Here's the hard truth, thatfrustration you feel when they
ask why.
It isn't about theirentitlement, it's actually about
your discomfort with adifferent way of working.
And if you want to lead themeffectively, you've got to get

(03:05):
comfortable with that discomfort.
Here's what I've seen happen.
When Gen X leaders make thisshift, they don't just become
better at leading youngergenerations, they become better
leaders.
Period.
The skills that engagemillennials in Gen Z clarity,
purpose, emotional intelligencethose same skills make everyone

(03:27):
on your team more effective.
The question isn't whether youshould adapt.
The question is what's itcosting you not to.
So let's talk about SimonSinek's golden circle.
You probably know this alreadyStart with why, then move to how
, then what.

(03:47):
But most leaders, especially usGen Xers we flip this thing
backwards.
We lead with what needs to bedone, maybe touch on how, and
rarely explain why.
Here's the shift.
Millennials and Gen Z don't justwant to know their tasks, they
want to understand the missionbehind the work.
They need to see how theireffort connects to something

(04:10):
bigger.
So instead of starting with thetask, start with the purpose.
Give them the why first, thenshow them what they'll do to
achieve it.
So here's an example the wrongway.
I need you to update the clientdatabase and clean up the
contact information.
Can you have this done byFriday?
Yeah, they won't respond tothat.

(04:33):
Here's a better way.
We're losing potential dealsbecause our sales team can't
find accurate client informationquickly.
It's costing us credibility andrevenue.
So what I'd like you to do isupdate our client database and
clean the contact information soour team can respond faster and
more professionally.
Can you have this ready byFriday so we can test it before

(04:55):
next week's big prospect calls?
It's the same task, completelydifferent buy-in level.
Here's a real example from myown team.
I had a marketing coordinatorwho kept missing deadlines on
his social media posts.
My first instinct was tomicromanage or get frustrated.
Instead, I sat down andexplained the why I said.

(05:20):
Here's what I realized I nevertold you.
When we post consistently, westay top of mind with potential
clients who are looking for help.
Every post is a touch pointthat can lead to a conversation
that changes someone's business.
What you're creating isn't justcontent, it's connection.

(05:41):
Now here's how we're going tomake sure you have what you need
to hit those deadlinesconsistently.
The result he started treatingthose posts like they mattered,
because now he understood theydid Start with.
Why, then, show them the what?
It's not about being trendy,it's about being effective.

(06:07):
All right, let me walk youthrough the five biggest
mistakes I see Gen X leadersmake with younger generations
and, more importantly, what todo instead.
Mistake number one expectingpeople to pay their dues the way
you did.
Look, we earned our stripesthrough years of grunt work,
late nights, proving ourselvesover and over and over.

(06:29):
So when a 26-year-old askedabout growth opportunities six
months into the job, ourknee-jerk reaction is you
haven't earned that yet.
But here's the thing they don'tneed to earn opportunity the
same way we did.
The economy is different, jobmobility is different,
expectations are different.

(06:50):
A better approach Shift to adevelopment mindset.
Instead of asking have theyearned it, ask how am I helping
them grow into it?
Ask how am I helping them growinto it.
Give them stretch assignments.
Let them shadow you in meetings.
Create pathways for growth,even if they're not the

(07:14):
traditional ones you wentthrough.
Mistake number two avoidingfeedback because it feels
awkward.
We grew up in a no news is goodnews culture.
If you weren't getting yelledat, you were probably doing fine
.
But for younger generations,silence isn't neutral, it's
anxiety inducing.
A better approach Give regular,clear, constructive feedback.

(07:38):
I'm talking weekly, notannually.
Millennials crave it.
Gen Z expects it.
And here's the secret when yougive good feedback regularly,
the difficult conversationsbecome easier because you've
built that foundation of trust.
And then mistake number threeassuming loyalty should be

(08:01):
automatic.
Assuming loyalty should beautomatic.
We stayed at companies foryears, even when we were
miserable, because that's justwhat you did.
But younger generations watchedtheir parents get laid off.
After decades of loyalty.
They've learned that companiesaren't loyal to them.

(08:22):
So why should they be loyal tocompanies?
A better approach Earn loyaltyby investing in people, provide
purpose, development and genuinesupport.
They'll stay for leaders whocare about their growth, not for
company logos or paychecksalone.
Mistake number four leading fromauthority instead of influence.

(08:43):
Our leadership models wereusually hierarchical.
The boss said jump.
You asked how high.
But younger generations?
They were raised to questionauthority, to think critically
and expect to have a voice.
A better approach, invitecollaboration and model humility

(09:04):
.
Ask for their input.
Admit when you don't knowsomething.
You'll earn respect by beingreal, not by demanding it
because of your title.
And mistake number five thinkingemotional intelligence is soft.
Emotional intelligence is soft.

(09:28):
This might be the biggest one.
We were taught to check ouremotions at the door right.
Keep social work and personalseparate.
Never let them see you sweat.
But here's what I've learnedafter years of leadership
coaching EQ isn't soft.
It's the hardest skill tomaster and the most important
one for results.
People perform best when theyfeel psychologically safe, seen

(09:51):
and supported.
A better approach Getcomfortable with emotions yours
and theirs.
And hear me, and hear me.
Check in on how people aredoing, not just what they're

(10:11):
doing.
Create space for vulnerability.
The leaders who mastered thisdon't just get better
performance, they get innovation, they get creativity and
loyalty.
All right, now let me tell youwhat they're really looking for,
and it's not free coffee.
Here's a conversation thatcompletely changed how I think
about this whole generationalthing.

(10:32):
I was working with a techcompany where the Gen X
leadership team was frustratedbecause their younger employees
kept asking for more feedbackand better communication.
Their younger employees keptasking for more feedback and
better communication.
These executives were rollingtheir eyes, thinking we already
have quarterly reviews.
What more do they want?
So I sat down with one of theirmillennial team leads and asked

(11:00):
her straight up what do youactually need from your manager?
Her answer surprised me.
She said look, I don't want aping pong table or unlimited PTO
.
I want a manager who checks inwith me regularly and actually
listens when I talk.
I want to know if I'm on theright track before my quarterly
review and I want to understandhow my work connects to
something bigger than justhitting this month's numbers.

(11:21):
That's when it clicked for me.
This isn't about entitlement orneediness.
It's about a fundamental shiftin how people want to be led.
Think about it, gen X leaders weoften grew up in environments
where you separated work frompersonal life.
You clocked in.
You did your job you clockedout.

(11:42):
But for millennials and Gen Zthat separation doesn't really
exist and, honestly, in today'sworld it can't.
They bring their whole selvesto work because modern life
requires it.
They're dealing with studentloans, caring for aging parents,
navigating a housing market.
That's completely differentfrom what we experienced.

(12:02):
Work isn't just a paycheck.
It's part of their identity andtheir path to building the life
they want.
So what they're looking for fromleaders is actually pretty
straightforward.
One clarity what's expected ofme?
Not just the task but thestandard, not just the deadline

(12:23):
but the priority?
Two consistency Will you followthrough on what you say?
If you promise feedback, willyou give it?
If you commit to supportingtheir growth, will you actually
do it?
Three coaching Will you help meget better?
This doesn't mean hand-holding.
It means investing in theirdevelopment, giving them stretch

(12:47):
opportunities and helping themconnect the dots between where
they are and where they want togo.
And then four, care Do I matterto you as a person or am I just
a resource?

Speaker 2 (13:00):
This is a big one.

Speaker 1 (13:02):
They want to know that you see them as a human
being, not just a function.
This is where your one-on-onesbecome absolutely critical.
By the way, if you haven'tlistened to my one-on-one series
yet, pause this episode and godo that, because your regular
check-ins are where these fourneeds get met.

(13:22):
That's where trust gets built.
That's where the bridge betweengenerations happens.
Don't assume disengagement.
Don't assume entitlement.
Start a conversation, askquestions, get curious about
what makes them tick.
Here's what I discovered whenyou meet these four needs

(13:42):
clarity, consistency, coachingand care you don't just get
better performance from youngergenerations, you create the kind
of leadership environment thatbrings out the best in everyone.
Now your action plan for thisweek.
Let's make this practical.
Here are three things you cando this week to start bridging

(14:03):
the generational gap on yourteam.
First, audit your leadershipmindset.
I want you to get honest aboutwhere you're still leading like
it's 1999.
Ask yourself am I expectingpeople to prove themselves the
same way I had to?
Am I giving feedback regularly?
Am I still operating on the nonews is good news model?

(14:25):
When someone asks, why, do Iget defensive or do I see it as
an opportunity to create buy-in?
Write down your answers.
Be brutally honest, becauseawareness is the first step in
this change.
Second, practice the why, firstframework.
This week, pick one significanttask you need to delegate Before

(14:48):
you explain what needs to bedone.
Start with why it matters.
Here's a simple template,here's why this is important.
And then insert the biggerpurpose.
Here's what I need you to do toachieve that.
Insert the specific tasks andhere's when I need it.
Insert the deadline.
Try it once, see howdifferently the conversation

(15:11):
goes.
See how much more engaged theyare when they understand the
mission behind the work.
More engaged they are when theyunderstand the mission behind
the work.
And third, have one genuineconversation.
Pick one person on your team,preferably someone from a
younger generation, and ask themthis question what's one thing
we could change to make yourwork more meaningful or

(15:31):
effective?
And then listen, really listen.
Don't defend, don't explain whythings are the way they are.
Just listen and take notes.
Let me tell you what happenedwhen I did this with my own team
.
One person said I'd love to knowif I'm doing a good job.
I don't really hear much unlesssomething's wrong.
Another said I wish Iunderstood how my work connects

(15:53):
to some bigger goal.
Sometimes I feel like I'm justchecking boxes.
Those two comments completelychanged how we structure our
team meetings.
In one-on-ones Now we startevery meeting with what's going
well before we dive intoproblems.
We spend time in our quarterlyplanning sessions connecting
individual roles to companyobjectives, and that result

(16:17):
Morale improved, retentionimproved and, honestly, I became
a better leader because Istopped assuming people or that
I knew what people needed andstarted asking you don't need to
fix everything this week, youjust need to start the
conversation.
So here's my question for youwhat belief about leadership are

(16:40):
you holding on to?
That might be holding your teamback.
If this resonated, share itwith another Gen X leader who's
wrestling with how to lead theseyounger generations.
Well, and if you want moretools for people-first
leadership, if you need coachingor a keynote speaker, visit my
website nextstepadvisorscom.
There's no E in that.

(17:01):
Next, it's just NXT.
I want to thank you forlistening to Things Leaders Do
Keep building bridges betweengenerations, leading with
clarity and rethinkingleadership norms.
And you know why?
Because those are the thingsthat leaders do.

Speaker 2 (17:26):
Thank you for listening to Things Leaders Do.
If you're looking for more tipson how to be a better leader,
be sure to subscribe to thepodcast and listen to next
week's episode.
Until next time, keep workingon being a better leader by
doing the things that leaders do.
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