How to Lead....When Leadership Won't
Navigating middle management when the existing culture and system is broken. An answer to a reader's letter.
Dear Christine,
I’ve just stepped into a new engineering leadership role—barely a month in—and I’m already seeing a forest full of red flags.
I’m leading a small team tasked with building a new Kotlin version of our company's flagship software. It needs to interface seamlessly with multiple architectures and languages—a real technical feat. But right out of the gate, I’m running into a classic issue: silos.
The company is thousands of people across dozens of teams. There’s a real culture problem…think: context switching, misalignment, duplicated work, delay. I've lived this movie before and I know how it ends.
What’s worse is that I’m the only one who seems alarmed. Everyone else is skipping through the forest, oblivious to the danger.
I have no budget and no mandate to fix this. But I also know that if we don’t address these structural issues now, we’re setting ourselves up for painful failure. Any advice?
—Tired of the Same Engineering Horror Film
Oof, do I feel you.
You're on the hook to deliver, but you’ve seen enough to know that the existing culture will sabotage you. It’s like predicting a car crash - only to live through it anyway.
Unfortunately, culture flows downward. The people who can truly fix “silos” sit at the top - and no leader easily admits that their culture isn’t collaborative.
So reframe your thinking. Your problem isn't "silos"—it's getting your project done within a system of silos. AKA: You're not leaving the forest of red flags, but navigating you and your team through it sanely and safely. It’s tricky, but doable. Here’s how:
1. Pick your Battles
When lots of things suck, it’s hard to let things lie. Especially when the “right” answer feels so damn obvious, it’s not intuitive to sit still.
But fixing problem isn’t just about knowing the answer. It requires many people to change their behavior; which takes political capital and influence.
Many smart leaders trip up here. They flag low test coverage while surfacing CI/CD issues while pushing back on InfoSec bureaucracy. Regardless of whether they're "right," they become perceived as difficult complainers.
Don’t fall into this trap. Instead, strategically select winnable, worthy battles.
Ex: “Silos” would be a huge challenge even for top executives. But fragmented, redundant meetings? You can fix that.
Projects like this are straightforward and deliver outsized impact. As you deliver wins, you accrue political capital for bigger battles later.
2. Unite Your Allies Under a Banner
Once you've picked a winnable fight, gather your allies. Who else sees the problem? Whose help do you need? Who has influence you could borrow? These are the people you want on your side.
Once you’ve identified these key players, bring them over. And critically:
Never presume they see the problem.
If you see red flags where they see a delightful woodland romp, you're doomed. It doesn’t matter that you’re “right”, people don’t move to solve problems they don’t see.
Here’s a doomed-to-fail approach:
Doomed: "I noticed that we have a ton of redundant, inefficient meetings. Can we work out a more streamlined meeting schedule?”
This is a solution, not a banner. People hear it and think: "We’re not inefficient," "…but I need meetings A and B!”, and "Good luck buddy—I tried this last year!"
Banners are narratives that unite people around a problem: why it exists, why it matters, and gives them a part to play in the solution. They work because they make others feel seen.
Banner: "Historically we had meetings A, B, and C for each team. Now that we've grown, meetings B and C overlap on X, Y, and Z. Jane and Lahiru have raised similar concerns. We're underwater, and giving everyone a few hours back each week will help a lot. Can we streamline our schedule?"
This narrative works because it blamelessly acknowledges pain points. It isn’t about “solving a problem”, but the well being of the entire team. By name-checking specific stakeholders, it borrows their influence and validates them.
So as you meet with potential allies, get curious. You’re likely not the first to try fixing this. What historical context created the problem? Why is it still unsolved? What don’t you know yet?
A note: It’s not always about giving someone a part to play! If a stakeholder can’t be brought on-board, the narrative should sideline them. Ex: “This new schedule is just for the engineering team - InfoSec is a very different process that Karen and Chad will continue to drive independently.”
3. Keep the banner up - rain or shine
In all of this, you’re not wielding direct power but influence. No one has to follow you, they’re choosing to - which creates a problem of its own:
How do you make someone do something…
When you can’t actually make them do it?
A common mistake leaders make is assuming they’re done after getting buy-in. They rally the troops, and put down the banner to get to “the real work”.
But narratives, once born, keep evolving: If you're not managing them, they can run rampant…or be picked up and co-opted by others.
“We’ve tried the new meeting schedule for a few weeks now, but it’s made X much harder. This sucks.”
“Jane said she’d do Y, but didn’t. This is so poorly organized.”
“My anxious manager just calls me constantly now - wasting even more time."
The goal here is not to quash objections or hide reality. It’s influence, not magic: you can’t tell people how they feel.
Accept that the narrative will evolve. Your job isn't to control, but to manage.
Here's how:
Document the project’s goals, milestones, owners: in whatever format fits your culture—PowerPoint, Notion, Google Doc. This helps everyone orient themselves and create a sense of continuity.
Set up a pre-scheduled cadence while the project is fresh. Even for simple tasks, schedule retrospectives and follow-ups in advance to maintain momentum.
Check in 1:1 periodically to gauge how people are feeling. These don't need to be hour-long meetings; just small moments of authentic outreach.
Celebrate wins publicly as they accrue. Be generous with credit and gratitude. Remember: they're choosing to help you. Repay that trust.
This is how the narrative might evolve:
Evolved Banner: "We’ve streamlined 3 hours of meetings each week: what a win! A huge shoutout to Lahiru for setting up Y. We’ve heard concerns about C, D, etc. - we’re doing a retro next week so we can review and figure out how to best address them."
Done right, it’s the polar opposite of sweeping things under the rug. Good narratives stay relevant because they continue to reflect how people see the world. Focus your time on listening, creating transparency, and celebrating those who trust you.
What success will feel like (and what it won’t)
Success won't feel like standing in the sun. There will be no great catharsis or triumphant validation. The system itself is broken: you can improve things, but you’re still in a forest of red flags.
But once you stop expecting sunlit accolades, you realize something else:
Dodging through a forest of red flags can be…outrageously satisfying.
Hacking the system, working against the odds, and plotting with allies? It’s a bonafide movie plot!
You're not some coddled baby with a silver spoon of excellent culture. You're a shrewd little imp who can survive the jungle on wits alone.
And the truth is…everyone needs to learn how to be the imp. We can never guarantee our environment. Not everyone can afford to quit bad jobs. Even CEOs need these skills to navigate the things outside of their control - boards, investors, and fickle customers.
Being the imp doesn’t mean you condone bad culture or bad behavior. It’s acknowledging that things will inevitably be shitty…and surviving regardless.
Where coddled babies can only wail helplessly, imps roll up their sleeves. They get shit done, create safe spaces for those around them, and generally leave things better than they found it.
With you, I can tell that the imp is already there: you've seen this movie before but still want to get your team through safely. Your have all the fundamentals: optimism, tenacity, and empathy.
So, fellow imp, good luck.
And have fun.
Christine Miao is the creator of technical accounting–the practice of tracking engineering maintenance, resourcing, and architecture. It turns massive initiatives - like breaking up monoliths, complex refactors, or cleaning up tech debt - into simple, visual reports.
Have a burning engineering question of your own? Drop a message or book a meeting.