When Your Team Is Right, and Leadership Is Wrong (And You're Stuck in the Middle)
The Moment You Realize You're Stuck
It's Monday morning. Leadership just announced a strategic initiative: migrate all branch offices to SD-WAN. Timeline: 90 days. Budget: what you already have. Resources: your current team.
You do the math. You have 25 branch offices. Your team has capacity for maybe one site per week if everything goes perfectly (it won't). That's 25 weeks minimum, and that's assuming no outages, no other projects, no operational work.
You bring this to your team. They look at you like you've lost your mind.
"That's not realistic," your senior engineer says. "We'd be cutting corners on testing, skipping documentation, and risking outages at every site. This needs 6 months minimum to do right."
He's right. You know he's right.
But leadership has already announced the timeline to the board. Contracts are signed. Expectations are set.
You're in the middle. Your team expects you to push back on behalf of technical reality. Leadership expects you to make it happen regardless of technical reality.
Welcome to the hardest part of middle management that nobody warns you about.
Six months into this role, I'm learning that being stuck between my team and leadership is a constant state. Not an occasional situation - a fundamental condition of the job.
Let me share what I'm learning about navigating this impossible position.
The Scenarios That Put You in the Middle
Let me get specific about the situations where you're caught between team reality and leadership expectations:
Scenario 1: The Impossible Timeline
What Leadership Says: "This network upgrade needs to be done by the end of Q2 to support the business initiative."
What Your Team Says: "That timeline is impossible. We need at least 6 months to do this safely. Rushing it risks major outages."
What You Know: Your team is right. The timeline is aggressive to the point of recklessness. But the business initiative is real, contracts are signed, and revenue depends on it.
Where You're Stuck:
Push back too hard on leadership: you look like you're not a team player, can't execute, or don't understand business priorities
Accept the timeline: your team loses faith in you, knows they're being set up to fail, and will burn out trying to meet impossible deadlines
Try to split the difference: nobody's happy, and you probably still fail
The Reality: There is no good answer. Only the less-bad options.
Scenario 2: Technical Debt vs. Feature Requests
What Your Team Says: "We need to address technical debt. Our infrastructure is fragile. We're one failure away from a major outage. We need time to fix foundational issues."
What Leadership Says: "Technical debt doesn't drive revenue. We need you focused on projects that support business growth. The infrastructure is working fine."
What You Know: Your team is right about the fragility. Leadership is right that technical debt doesn't appear on revenue reports. Both can't be fully satisfied with the available resources.
Where You're Stuck:
Prioritize technical debt: leadership questions your strategic thinking and business alignment
Prioritize features: your team sees you as ignoring technical reality and setting everyone up for future crisis
Try to do both: you do neither well, technical debt compounds, and features are delivered late
The technical debt tension is something I explored in depth in Technical Debt: What Engineers Wish Managers Understood - this is the engineer’s side of that same conflict.
Scenario 3: Resources Your Team Needs But Won't Get
What Your Team Needs: "We need another engineer. We're at capacity. We need a training budget, and we need better tools. We need contractors for this peak period."
What Leadership Says: "No additional headcount approved. The training budget is frozen. We need to be efficient with existing resources. Make it work."
What You Know: Your team genuinely needs resources. They're not exaggerating or being dramatic. But budget constraints are real, and you're not getting exceptions.
Where You're Stuck:
Fight hard for resources: you spend political capital you don't have, probably lose anyway, and look naive about organizational realities
Accept the constraints: your team thinks you didn't even try, didn't advocate for them, and don't understand their workload
Keep asking: you become "the manager who's always asking for more," and leadership stops listening
Scenario 4: Process Changes Your Team Resists
What Leadership Mandates: "All IT teams will adopt this new project management methodology/tool/process. No exceptions."
What Your Team Says: "This process doesn't fit how network engineering works. It'll slow us down. The tool is clunky. This is change for change's sake."
What You Know: Your team might be right that it's a poor fit. But the mandate is organization-wide and non-negotiable.
Where You're Stuck:
Defend the mandate: your team sees you as a mouthpiece for bad leadership decisions
Side with your team: leadership sees you as resistant to change and not supporting organizational initiatives
Try to implement it halfheartedly: neither side is satisfied
Scenario 5: "Do More With Less"
What Leadership Says: "We need to find efficiencies. Budget is tight, and headcount is frozen but business demands are increasing. We need you to optimize."
What Your Team Hears: "Work harder. Work longer hours. Sacrifice work-life balance. And somehow be happy about it."
What You Know: No magic efficiency suddenly makes your team 30% more productive. "Optimize" is code for "overwork your existing team."
Where You're Stuck:
Communicate the expectation honestly: team morale tanks, people start looking for other jobs
Shield your team completely: work doesn't get done, and leadership questions your ability to execute
Try to find actual efficiencies: there might be some, but not 30% worth, and you're still asking people to do more
What Doesn't Work (Things I've Tried and Failed)
Let me share my failures first, because I've tried a lot of approaches that made things worse:
Failed Approach 1: Being Transparently Honest With Both Sides
What I Tried:
Told my team exactly what leadership said and why. Told leadership exactly what my team said and why. Figured transparency would help everyone understand the constraints.
What Happened:
My team felt unsupported: "You're just passing down their bad decisions without fighting for us."
Leadership thought I was undermining them: "Why are you telling your team we debated this? Just implement it."
What I Learned:
Full transparency in both directions isn't helpful. It makes you look like a messenger, not a leader. Both sides want you to filter, translate, and advocate - not just pass messages unchanged.
Failed Approach 2: Trying to Please Everyone
What I Tried:
Promised leadership, we'd hit the timeline. Promised my team we wouldn't cut corners and figured I'd somehow make both happen through sheer effort.
What Happened:
We missed the timeline (couldn't hit it without cutting corners). We cut corners (couldn't avoid it, given the timeline). Leadership was disappointed. The team felt betrayed. I looked incompetent to both.
What I Learned:
You cannot please both sides when their positions are fundamentally incompatible—trying to make you look dishonest or delusional.
Failed Approach 3: Complaining About Leadership to My Team
What I Tried:
I vented frustration about leadership decisions to my team. Thought it would build solidarity and show I was "on their side."
What Happened:
Team morale got worse, not better. I permitted them to be cynical and negative. Word got back to leadership (it always does). Lost credibility with leadership. Didn't gain as much with the team as I thought.
What I Learned:
You can acknowledge constraints without undermining leadership. Venting down creates a toxic culture and damages your credibility everywhere.
Failed Approach 4: Fighting Every Battle
What I Tried:
Pushed back on every unrealistic timeline, every resource constraint, every mandate I disagreed with. Figured my job was to fight for my team on everything.
What Happened:
Burned through all my political capital in the first three months. Leadership stopped listening because I was "always negative." When I had a genuinely critical issue to escalate, nobody took me seriously.
What I Learned:
You have limited political capital. Spend it on battles that matter. Fighting everything means winning nothing.
Failed Approach 5: Just Implementing Bad Decisions Without Context
What I Tried:
"Leadership says we're doing this, so we're doing it. That's the decision." Didn't explain reasoning, didn't acknowledge concerns, just mandated compliance.
What Happened:
The team felt like I was just a puppet passing down orders. Lost their trust and respect. They complied minimally and resentfully.
What I Learned:
Even when implementing decisions you disagree with, how you communicate them matters. Context and acknowledgment matter.
Learning what works vs. what fails is part of the management learning curve I explored in 5 Things I Wish I Knew Before Becoming a Manager - you learn this stuff by doing it wrong first.
What's Actually Working (Most of the Time)
After failing in various ways, here's what I'm learning actually helps:
Strategy 1: Translate, Don't Just Transmit
What This Means:
When communicating from leadership to team: translate business context into technical implications.
When communicating from the team to leadership, translate technical concerns into business impact.
Example - Leadership to Team:
Don't say: "Leadership wants this done in 90 days. That's the timeline."
Do say: "Leadership committed to a customer contract that requires this by the end of Q2. I know that's aggressive. Here's what I'm thinking about how we approach it, and I need your input on what's realistic within that constraint."
Example - Team to Leadership:
Don't say: "My team says the timeline is impossible."
Do say: "The timeline carries significant risk. Here's the trade-off: we can hit 90 days with reduced testing and a higher probability of outages, or we can take 120 days with proper testing and minimal risk. Which risk profile aligns with business priorities?"
Why This Works:
You're not just passing messages. You're interpreting and framing them in language each side understands.
Strategy 2: Advocate Up, Implement Down
What This Means:
In private conversations with leadership: fight for your team, push back on unrealistic demands, propose alternatives.
When implementing decisions: own them with your team, even if you disagree.
The Example:
In the leadership meeting:
"I hear the business need for the 90-day timeline. I want to be transparent about the risks. My team can accelerate to 4 months with overtime and deferred maintenance. Pushing to 3 months means cutting testing and documentation, which increases outage risk significantly. Is that trade-off acceptable?"
With my team afterward:
"Leadership has decided to proceed with the aggressive timeline because of the customer contract. I pushed back and got us an extra month, but we're still tight. Here's how I'm thinking we approach this to minimize risk while hitting the deadline. What am I missing?"
Why This Works:
Team sees you fought for them (you did, privately). Leadership sees you implement their decision (you are, even if you disagree). You're leading, not just messaging.
The Caveat:
If the decision is genuinely unethical or will cause serious harm, you can't just implement it. But most decisions are just suboptimal, not unethical.
Strategy 3: Give Options, Not Just Objections
What This Means:
When you disagree with something, propose alternatives instead of just saying no.
Don't say: "That timeline won't work."
Do say: "That timeline is aggressive. Here are three options:
Hit 90 days by cutting testing - higher risk, faster delivery
Take 120 days with full testing - lower risk, better quality
Hire contractors for 90 days - hit timeline with acceptable risk but increased cost
Which aligns with priorities?"
Why This Works:
You're not just being negative. You're showing you understand constraints and proposing solutions. Leadership can make informed decisions.
Strategy 4: Pick Your Battles
What This Means:
Not every bad decision is worth fighting. Save your political capital for things that really matter.
Questions I Ask Myself:
Is this genuinely high-risk, or just not how I'd do it?
Will this create lasting harm, or just temporary inconvenience?
Is this the hill I want to die on?
Do I have credibility to spend on this issue?
The Example:
Leadership mandates a new project tracking tool I think is overkill. My team will complain.
My assessment: Annoying but not harmful. Not worth political capital to fight.
My approach: Implement it without drama. Save my capital for the budget fight that actually matters.
Why This Works:
When you do push back on something, leadership knows it genuinely matters. You're not the manager who objects to everything.
Strategy 5: Acknowledge Reality Without Creating Helplessness
What This Means:
Be honest with your team about constraints while maintaining agency and optimism.
Don't say: "Leadership is being unreasonable, but there's nothing we can do."
Do say: "Leadership has set an aggressive timeline due to business constraints. I've pushed back and gotten some flexibility, but we're still tight. Here's what we can control: how we approach the work, what we prioritize, and how we manage risk. Let's focus on what's within our control."
Why This Works:
Acknowledges reality without creating a victim mentality. Focuses on agency rather than helplessness.
Strategy 6: Create Small Wins Within Constraints
What This Means:
Even within bad situations, find ways to deliver wins for your team.
The Example:
Timeline is aggressive and won't change. Budget is frozen.
What I Can Do:
Negotiate comp time after the rush period
Shield them from non-essential meetings during crunch time
Get leadership to publicly recognize their effort
Defer other lower-priority work to reduce overall load
Bring in lunch during overtime periods
Why This Works:
Shows you're trying to make bad situations less bad. Demonstrates you care about their well-being even when you can't change the fundamental constraint.
Strategy 7: Be Honest About What You Can't Change
What This Means:
Sometimes the answer is "this is a bad decision, and I can't change it."
The Conversation:
"I agree this timeline is aggressive. I pushed back in multiple meetings and explained the technical risks. Leadership has decided the business need outweighs those risks. I don't agree, but this is the decision. Here's how I think we mitigate the risks as best we can."
Why This Works:
Your team respects honesty. They'd rather know you fought and lost than think you didn't try.
What You DON'T Say:
"I think this is stupid, but we have to do it anyway."
That undermines leadership without actually helping your team.
The Conversations Nobody Teaches You
Let me get specific about difficult conversations you'll have:
Conversation 1: "Why Didn't You Fight Harder?"
Your Team Member Says:
"Did you even push back on this? Did you tell them this timeline is impossible?"
What They're Really Asking:
"Are you on our side or theirs?"
What NOT to Say:
"I did push back, but they didn't listen." (Makes you sound ineffective)
"This is the decision, and we need to execute." (Makes you sound like a corporate drone)
What Works:
"I did push back. I explained the technical risks and proposed a longer timeline. Leadership decided the business need was urgent enough to accept higher risk. I don't fully agree, but I understand their reasoning. Now my job is helping us manage that risk as best we can."
Why This Works:
Shows you advocated and acknowledged the tension. Focuses on moving forward.
Conversation 2: "You Don't Understand What We're Dealing With"
Your Team Member Says:
"Leadership doesn't get it and clearly you don't either if you're agreeing with them."
What They're Really Saying:
"You've become one of them. You're not a technical person anymore."
What NOT to Say:
"I do understand, but I have to think about the business." (Confirms their fear that you're "management" now)
"You need to understand the business constraints." (Sounds condescending)
What Works:
"You're right that I'm not in the weeds daily anymore. That's why I need you to help me understand the full picture. Walk me through specifically what concerns you about this approach. What am I not seeing?"
Then actually listen. Their concerns might change your approach or give you ammunition to push back further.
Why This Works:
Acknowledges the gap. Invites their expertise. Shows you value their input.
Conversation 3: "If You Won't Fight for Us, Why Are You Here?"
Your Team Member Says:
"What's the point of having a manager if you're just going to pass down whatever leadership wants?"
What They're Really Asking:
"Are you going to protect us or sacrifice us?"
What NOT to Say:
"I am fighting for you." (If it doesn't feel like it to them, saying it doesn't help)
"That's not fair, I'm doing my best." (Defensive and unproductive)
What Works:
"I hear your frustration. From your perspective, it feels like I'm not fighting for the team. Let me be specific about what I have pushed back on and what's changed as a result: [specific examples]. There are some battles I've won and some I've lost. I can't change every decision, but I am advocating for the team. If it's not landing that way, I need to know what you need from me."
Why This Works:
Specific examples of advocacy. Acknowledges their perception. Opens dialogue about what support looks like.
These difficult conversations are part of managing through burnout and stress, something I explored in Both Sides of the Desk: Burnout - being in the middle is exhausting for everyone.
Conversation 4: Leadership Questioning Your Commitment
Your Boss Says:
"You seem resistant to this initiative. Are you on board or not?"
What They're Really Asking:
"Are you a team player or a problem?"
What NOT to Say:
"I'm on board." (If you've been vocally skeptical, this sounds fake)
"I think this is a bad idea." (Confirms their concern about your commitment)
What Works:
"I want to be transparent: I have concerns about [specific issue]. I've shared those concerns and proposed alternatives. Now that the decision is made, I'm committed to implementing it as successfully as possible. If my questioning came across as resistance rather than risk assessment, that wasn't my intent."
Why This Works:
Acknowledges your concerns. Commits to implementation. Reframes pushback as due diligence, not obstruction.
When to Fall on Your Sword (And When Not To)
The Question:
Are there situations where you should refuse to implement something? Where should you escalate beyond your boss? Where should you be willing to lose your job over?
The Answer:
Yes. But they're rarer than you think.
When to Take a Stand
Genuinely unethical or illegal requests:
Violating regulations you're subject to
Falsifying reports or data
Implementing something that knowingly endangers people
Decisions that will cause catastrophic harm:
"Decommission our backup systems to save money."
"Skip all security testing to hit timelin.e"
"Don't tell anyone about the data breach we discovere.d"
These are rare. Most bad decisions are just... bad decisions. Suboptimal. Risky. Frustrating. But not worth falling on your sword over.
When to Implement Despite Disagreement
Most situations fall here:
Aggressive timelines you think are risky but not impossible
Resource constraints that make work harder but not impossible
Priorities you disagree with but aren't catastrophic
Processes you think are suboptimal but not harmful
The Reality:
If you're willing to resign over every decision you disagree with, you'll be unemployed. Part of middle management is implementing decisions you think are suboptimal.
The Key:
Advocate clearly for what you believe is right. If overruled, implement professionally. Document your concerns and the decision. Then make it work as well as you can.
Taking Care of Yourself in the Middle
Let's be honest:
Being stuck in the middle is exhausting. Emotionally draining and sometimes soul-crushing.
You're managing:
Your team's frustration and stress
Leadership's expectations and pressure
Your own frustration when you can't fix things
The gap between what should happen and what will happen
The Toll This Takes
What I'm Experiencing:
Stress from disappointing people in both directions
Guilt when I have to implement decisions I disagree with
Frustration when I can't protect my team from organizational dysfunction
Exhaustion from constant negotiation and translation
Isolation because I can't fully vent up or down
The Temptation:
Check out emotionally. Stop caring. Just pass messages and implement orders without thinking about it.
Why That's Dangerous:
You become the ineffective middle manager everyone complains about. And you lose what made you good at this in the first place.
What Actually Helps
1. Find Peer Support
Other managers dealing with the same tensions. They get it. You can vent safely.
Not your team. Not your boss. Peers.
2. Accept What You Can't Control
You cannot fix organizational dysfunction from a middle management position. Some decisions will be bad. Some situations will be unfair.
Your job is making the best of bad situations, not fixing the organization.
3. Celebrate Small Wins
You got an extra month on the timeline. You secured a small budget increase. You prevented a terrible decision.
These matter even if they're not perfect outcomes.
4. Remember Your Purpose
You took this role to make a difference for your team and the organization. Some days you can. Some days you can't. But the purpose matters even when it's hard.
5. Know Your Limits
If every day feels like betraying your team or your values, that's a signal. Maybe it's a bad manager. Maybe it's a dysfunctional organization. Maybe it's a mismatch.
Staying in a situation that's destroying you isn't noble.
Managing your own stress while supporting your team is something I explored in Both Sides of the Desk: Burnout (Manager's Perspective) - you can't sustain this role if you don't take care of yourself.
What I'm Still Learning
Six months in, I don't have this figured out. Here's what I'm still struggling with:
How much transparency is right?
Too much and I undermine leadership. Too little and I lose team trust. I'm still calibrating.
When to keep fighting vs. when to accept defeat?
I don't always know when I've done enough advocacy and should move to implementation.
How to maintain team morale through constant constraint?
We're always doing more with less, hitting aggressive timelines, and deferring technical debt. How do I keep people engaged and motivated long-term?
How to avoid becoming cynical?
When you see enough bad decisions, it's easy to become the jaded manager who expects nothing good from leadership. I don't want to be that person.
How to balance honesty with professionalism?
I want to be real with my team about challenges. But there's a line between honesty and undermining leadership. I'm still finding it.
The Bottom Line: The Middle Is Where Leadership Actually Happens
Here's what I'm learning about being stuck in the middle:
It's not a bug, it's a feature. Middle management exists precisely because there's tension between frontline reality and organizational strategy. If there were no tension, you wouldn't need managers.
Your job is translation and navigation. You translate business needs into technical work. You translate technical constraints into business impact. You navigate between competing demands.
You can't please everyone. Some decisions will disappoint your team. Some will disappoint leadership. That's inherent to the role.
Advocacy matters even when you lose. Your team needs to know you fought for them, even if you didn't win. Your credibility comes from effort, not just outcomes.
How you implement bad decisions defines you. Every manager faces decisions they disagree with. What separates good managers from bad is how they handle implementation.
The middle is lonely. You can't fully vent up or down. You need peer support from people in similar positions.
You're building credibility slowly. Each situation is a test. Win enough tests, and eventually you have standing to influence bigger decisions.
Perfect is impossible. You're trying to balance incompatible demands with incomplete information and limited power. Sometimes "less bad" is the best you can do.
Your team is watching how you handle this. Not whether you win every battle, but whether you fight for them, communicate honestly, and maintain integrity.
This is the job. If you wanted to just implement orders, you could have stayed an individual contributor. If you wanted full autonomy, you'd need to be the CEO. Middle management is navigating between the two.
The Framework I'm Using
When stuck between team and leadership:
1. Assess the situation
Is this genuinely harmful or just suboptimal?
Is this worth political capital to fight?
What's within my control and what's not?
2. Advocate up privately
Push back with specific concerns and alternatives
Translate technical constraints into business impact
Propose options, not just objections
3. Implement down professionally
Own the decision even if you disagree
Provide context without undermining leadership
Focus on what's within the team's control
4. Find small wins within constraints
Ways to make bad situations less bad
Demonstrate care for team wellbeing
Build trust through small actions
5. Document and learn
Track what you advocated for and the results
Learn what arguments work with leadership
Understand what your team needs from you
6. Take care of yourself
Find peer support
Accept what you can't control
Know your limits
Related Posts
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How do you handle being stuck between your team and leadership? What's worked for you? What's made it worse? Share your experiences in the comments or connect with me on LinkedIn - we all need support navigating this.