The Conflict Series, Episode 3: Managing Up — How to Disagree with Your Boss Without Killing Your Career

Managing Up — How to Disagree with Your Boss Without Killing Your Career

Disagreeing with your boss doesn’t have to be career suicide. In fact, it might be your most powerful leadership move—if you do it the right way.

In the final episode of The Conflict Series, Colby Morris tackles one of the toughest challenges for leaders in the middle: how to manage up. Whether you’re a middle manager, a team lead, or a high-performing individual contributor, you’ve likely faced the tension of wanting to speak up without stepping out of line.

This episode gives you the mindset, language, and strategy to disagree with leadership without damaging trust or credibility. Learn how to bring respectful pushback, contribute solutions instead of complaints, and connect feedback to shared goals—all while strengthening your influence from the middle of the org chart.

In this episode, you’ll learn:

• Why most leaders get managing up completely wrong
• How to challenge direction without sounding combative
• A 3-part framework to speak up clearly, calmly, and credibly
• Real-world examples of how to bring feedback up the chain
• A leadership challenge to help you practice the right way this week

Whether you’re looking to build credibility with your boss, influence strategy from the middle, or coach your team on how to lead up well—this is the episode that brings it all together.

If this episode gave you new insight or language to lead from the middle, share it with your team or send it to another leader you respect.
Want to bring this conversation into your organization? Colby is available for speaking engagements, executive trainings, and leadership retreats focused on communication, culture, and courageous leadership.
Connect on LinkedIn or reach out through the link below.

NXT Step Advisors

• Colby's LinkedIn Profile
• Things Leaders Do Instagram

Episode Transcript

Speaker 1 (00:01):
What do you do when your boss is headed in the wrong
direction?
What do you do when thedecision from above doesn't
match the reality on the ground?
Do you stay quiet and just hopeit gets better?
Do you push back and risk beinglabeled difficult?
In today's episode, the finalpart of the conflict series,

(00:26):
we're talking about one of themost misunderstood and really
the most underdevelopedleadership skill out there
managing up, because saying hardthings downward is hard enough,
but when you're trying to sayhard things upward, that takes
real clarity, real courage andyeah, real wisdom.

(00:50):
And today I'm going to show youhow to do it.
Hey, leaders, welcome back tothe TLD podcast.
I'm Colby Morris and I'm hereto help you lead better, faster,
hopefully giving you real-worldtools you can use.
Today, all my episodes aredesigned to fit into your

(01:11):
commute and packed with enoughsubstance to shift how you lead
the moment you walk in the door.
So let's start the reality ofleading from the middle.
Well, many of you listening outthere know exactly what I'm
talking about because you'vemessaged me on LinkedIn to tell

(01:33):
me about it.
Middle managers are in what Icall the tension point.
You're expected to lead yourteam well, but also to carry out
decisions that are coming fromabove, even if you don't agree
with them.
And when you challenge upward,the stakes feel higher.

(01:55):
Right, what if they think I'mout of line?
Or what if they retaliate?
Or what if I ruin therelationship?
But here's the truth.
Great leaders want feedbackOkay, great leaders need it and

(02:15):
if you learn how to manage upand you do it well, you build
trust, you build credibility andinfluence.
You build trust, you buildcredibility and influence.
So I want to give you threeprinciples for managing up and

(02:39):
how to do that with courage andrespect.
First, I want you to clarifyyour intent before you challenge
direction.
See, before you go in withcriticism or opposition, you're
going to have to check yourself.
Are you just frustrated ormaybe you're actually trying to

(03:00):
improve the outcome?
See, leading up starts withchecking your motive.
Your tone should reflect adesire to contribute, not to
call out or just randomlychallenge.
Try something like I want tomake sure we're as effective as
possible here.
Or I may be missing something,but from my perspective, here's

(03:24):
what I'm seeing.
I want you to remember this.
Tone matters more than youthink.
You can say the same words twodifferent ways and get two
radically different reactions,and you know what I'm talking
about.
All right.
Two, I want you to lead withdata, not emotion.

(03:45):
See, disagreeing up the chainis a lot easier when you're
holding evidence instead ofemotion.
Did you hear that Disagreeingup the chain is a lot easier
when you're holding evidenceinstead of emotion?
You don't need to prove yourboss wrong.
You need to show them what'sreal.

(04:09):
You need to bring metrics, youneed to bring examples,
observations from the team, therisks that you're identifying,
and then start out this way hey,here's what we've seen since we
implemented whatever.
Or here's the feedback I'mgetting from the team.

(04:29):
I wanted to raise this so wecan get ahead of any fallout.
Here's what you need to know.
It's not disagreement that getspeople in trouble, it's
delivery without credibilitythat makes all the difference in

(04:50):
the world, all right.
Three, I want you to frame yourfeedback in terms of shared
goals.
The fastest way to get shutdown make it sound like a power
struggle.
Okay, the fastest way to beheard, you have to connect your
point to what they care about.

(05:11):
Try something like I know we'reboth trying to increase
adoption of this process.
Here's something I think mightget in the way.
Or, hey, since we're bothfocused on team retention, I
wanted to flag something that Ithink could impact morale.
See, in this instance, you'renot just pushing back, you're

(05:34):
partnering for a better result.
Okay, you're being a partnerwith that leader and tying in
what they want with what youwant.
Years ago I had a boss Verydriven, very sharp, very
respected in the entireorganization but they rolled out

(05:56):
a top-down initiative that justwasn't working on the ground
level.
Okay, I saw the morale just die.
Okay, productivity stopped.
You can say it slipped, itstopped.
I knew I had to say something.
Now I didn't barge in, I didn'tblast them with complaints, I

(06:20):
just sat down with them.
I said hey, I know the goalhere is speed, but I want to
show you how it's playing out inreal time with the team.
I brought metrics, I broughtexamples and I came with
solutions, not just problems.
And you know what they knowwhat he said.

(06:41):
He said thanks for not justunloading on me.
This helps, man.
That moment taught me somethingI have never forgotten the best
leaders don't need you to agree,they need you to be honest.
Here's what leaders get wrongwhen they're managing up.

(07:04):
It's not just about whether youget feedback, it's about how
you do it.
Okay, here are three commonways that leaders just miss the
mark when they're managing up.
And what to do instead?
Okay, first, they vent insteadof communicate.

(07:25):
Hey, I'll admit it feels goodto blow off steam, but when you
take that unfiltered emotiondirectly to your boss, it
doesn't land as helpful, itlands as hostile.
What feels like speaking yourtruth can come across as

(07:46):
immaturity if you haven't filledyour thoughts with clarity and
purpose.
So what's the fix?
Go vent to a mentor.
Okay, you vent to a mentor, butyou communicate with your
leader.
Use your support system.
Okay, that's how you processyour feelings and then you can

(08:10):
go into the conversation withyour leader, calm, prepared.
You can focus on the issue andnot the frustration.
Two, they assume their bossdoesn't want feedback.
So many mid-level leadersbelieve the person above them

(08:33):
just doesn't care or, worse,already knows and doesn't want
to hear it again.
But most of the time they don'tknow what you know.
They're operating from atotally different view, with
different pressures, and theymay not realize how things are
actually playing out, especiallyon the front line.

(08:54):
When you assume your bossdoesn't want feedback, you rob
them of the chance to get betterand you rob yourself of the
chance to lead.
You have to start withawareness, start with belief
that they might be open if youapproach the right way.

(09:16):
And then three, they wait untilthey're angry.
This is the biggest trap.
You know what I'm talking about.
You hold it in, you justify,you keep pushing it down until
one day it comes out sidewaysand instead of that helpful

(09:37):
insight, it becomes aconfrontation.
By the time you speak up.
It's not feedback, it's afrustration dump, and that is
what hurts your credibility.
You can't wait for the blow upmoment.
If something feels off, addressit early, when it's a coaching

(09:57):
moment, not a crisis.
All right, here's yourleadership challenge for this
week.
I want you to take action.
First, I want you to identifyone decision or one direction
from leadership that you've beenhesitant to speak up about
Bigger ball, I want you to nameit and name it clearly up.

(10:23):
About Big or small, I want youto name it and name it clearly.
Two or second, I want you towrite down your observations.
Okay, filter out thefrustration, focus on facts,
focus on the outcomes, thepatterns, potential risks.
And then, three, reframe yourapproach.
And then three, reframe yourapproach.
What does your leader careabout?
Do you know?
How does that tie into theirpriorities?

(10:45):
Shape your message to alignwith shared goals.
And then, finally, I want youto schedule the conversation or
rehearse it.
Yes rehearse it.
Practice the words.
Rehearse it.
Yes, rehearse it.
Practice the words.
Practice the language.

(11:06):
Okay, keep your tone calm.
Lead with clarity, not withcriticism.
The more you practice it, themore you'll be in control when
you finally get to have thatconversation.
Look, leadership isn't justmanaging down.
It's managing across and it'smanaging up too.
If you want to lead well in themiddle, you need courage, you

(11:29):
need clarity and you need theability to deliver truth without
torching the trust.
Okay, managing up is part ofbeing a people first leader,
because it means advocating foryour team and contributing to
the success of the people aboveyou.
If your organization needs helpbuilding a culture where

(11:51):
feedback can flow in everydirection, I'd love to help.
You can connect with me onLinkedIn or look in the show
notes.
I'll put the link in there forhow you can get a hold of me.
I'd love to help out, and ifthis episode helped you, I'd
love for you to share it withanother leader who's navigating

(12:12):
these same challenges.
So go out there, lead up, leadwell, be a good leader, be
courageous in what you're doing.
And you know why?
Because those are the thingsthat leaders do.

Speaker 2 (12:32):
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.