The qualifications of someone who will do well managing teams of hundreds with multiple layers of management are not at all obvious and look nothing like your traditional type-A resume.
Big logos, ivy league degrees, business school at the likes of Wharton/Booth/Kellogg/Sloan/Stern/<old dead guy’s name here>, even flashy launches and landing impressive OKRs. All of it “helps” but none of it is what makes you truly prepared.
Maybe you’ve been leading a 20-30 person org for a few years now with a string of successes under your belt. You are poised and professional, can present at an all-hands or executive project review without stumbling, and managing your team feels like it takes only one-quarter of your total brain power. Everything is on auto-pilot. You ask your boss for a bigger opportunity: that new P0 company imperative or a larger org or something like that.
His reply? “You’re not ready.”
What follows will usually be some stilted, sweaty feedback conversation where your manager tries to explain what you need to do to become ready…all while everyone in the room is distractedly thinking “shoot me, shoot me with a gun, right now.” None of it sounds convincing or like something you haven’t already done: the feedback will be polite nothings like be more visible to VPs, have more org-wide impact, build a brand1.
First off, if you follow any of this literally you are doomed to fail. You’ll burn cycles doing some performative “horizontal” initiative2 thinking it checks the box and still get denied. Feedback extracted under duress is just not fully thought out. Moreover, most members of upper management are holding back because they don’t know if you can handle the hard truth, nor do they really know how to express the things you’re missing without landing themselves in front of HR.
This post is the unfiltered answer: the experiences, capabilities and proof points that are the real determinant for who gets propelled into middle- and upper-management.
If you have to ask, you’ve already failed.
I’ve been managing managers (of managers of managers) for the last couple years now. I have some version of this “I want more” conversation every other month. “Yea buddy, get in line” is what I really want to say.
Every single person in my shoes is busy as hell and desperate to delegate away 40-50% of the things on their plate. The implication is that if your boss thought highly of you, they would be actively pushing more scope onto you in advance of asking for it (and often before you personally feel ready). If it doesn’t feel like you’re getting DDoS’d by your manager, then you are not their favorite child.
The naive response in this situation is to ask them: “what can I take off your plate?” But this just puts them on the spot. Here’s what races through my mind…
Oh gosh, um, let me somehow zoom out in the next 5 seconds and think about ALL THE THINGS in my work life. Now I need to filter this down to things I think you can actually do well…
…and that are important enough that it will show real growth.
…and that I have not promised to someone else or have someone better suited in mind.
…and that I think you will actually say “yes” to and put your full effort behind.
All of this while you’re staring at me expectantly. Please don’t do this. If you absolutely have to approach this way, send an e-mail in advance of your next 1:1.
A better approach is to be more observant of your boss, your org, and the company. Take notice of what is occupying everyone’s time, where things are falling through the cracks, and the problems everyone is ignoring. Pick one and then tell your boss: “I’m interested in doing more, I’ve noticed <X> is a recurring challenge, I think it’s valuable to solve now because <Y>, and I plan to approach as follows: …”
This works so well because it puts effectively zero demand on your manager. They can simply nod and say “make it so.” Besides making your executive feel like Jean-Luc Picard (which can only be a good thing), it also demonstrates that you are someone who seeks challenge. What you’re demonstrating is creative dissatisfaction, an all important prerequisite to even be considered for upper leadership. Senior executives are expected to constantly look for ways to improve the company’s products and processes.
Famously, the “seeking challenge” phase was the last step in Kraft’s Leadership Corridor, the development methodology that made a cheese company into one of the premiere factories for producing executive talent that would go on to become CXO’s across the Fortune 500 (case study).
Be like the cheese people, seek challenge.
Experience dealing with everything the job can throw at you.
Part of ascending the ranks is handling more. More people, more orgs, more projects, more problems, more situations you were previously shielded from. You have to deal with these things directly but also increasingly through your management team…all with complete independence.
I don’t mean the “normal stuff” like aggressive deadlines, competitive pressure, staffing turnover, or new technologies. I mean the crazy shit: job abandonment, leadership coups, layoffs, acquisitions, deathmarches, feuds between your boss and their peers, etc.
This has two implications:
You must be confident enough to handle these things on auto-pilot without days and days to research, discuss, and prepare. You must be able to walk into the most fucked up situation you’ve ever seen and go “huh, alrighty then” and one-shot it.
You must be able to teach other managers how to handle these things, perhaps for the first time and without taking on too much yourself. You must be able to project the strength, certainty and warmth to put others into a positive and productive state of mind so they can rise to the occasion.
You won’t be able to do this without lots and lots of experience. This isn’t meant to be an ageist thing (you can collect experience fast or slow, this is the reason I could break into the executive ranks in my 20’s). You may be great at generalizing concepts, but these will come at you so fast and so hard there will be no time to invent solutions from first principles.
There is no replacement3 for witnessing first-hand how these situations play out, how they react to certain interventions, and the playbooks world-class leaders and beacon companies have developed. This sort of exposure gives you not just concrete examples to follow, but builds your intuition and sensemaking capacity.
Entering into a situation and figuring out what must have happened for the situation to have turned out this way, as well as which way the situation is headed unless something changes.
Seeing how the things one does connect to other things that happen elsewhere.
Being able to tell when things are subtly out of the ordinary, when things are about to go wrong, or when everything is in place for things to go right.
Knowing techniques to extract feedback from a situation to improve one’s mental models, rearranging or combining steps in procedures to be more efficient.
Being able to come up with alternative processes on the fly based on understanding of the situation.
Keeping track of how well one is doing, and which the areas are in which one needs improvement the most (this is the reason experts don’t always need mentors the way beginners do).
The 142 Horrors of Management
Without further ado, here is a selection of situations and experiences you must have navigated previously to be considered “ready” for upper management (or were proximate enough to pick up the know-how 2nd hand):
Employees that abuse company-, state-, and federally-protected leaves to avoid accountability.
Employees that just straight up disappear without a word aka job abandonment.
Employees that weaponize HR/employee-relations/ombuds complaints against their manager to neuter performance management.
Getting sued by a competitor, customer, or employee.
Inheriting employees that were never given necessary feedback and puffed up by prior managers…now disappointed to not be showered with praise, promotions, and elevated ratings.
Managers that were given too many reports too quickly but aren’t willing to admit they are drowning.
Managers that skip standups, delay or cancel 1:1s, and generally spend all their time “away” from their team.
Managers that are badly calibrated and have fundamentally misled their entire team about the performance bar: failing to deliver feedback, inflating ratings, setting inappropriate growth expectations, and letting poor performers flourish…none the wiser that they are in for a reckoning.
Managers that ignore/violate company policy out of self-interest, creating other secondary issues, all while concealing everything from you4.
Managers that don’t explain the vision or strategy to the team and just say “we’re doing X because the big boss said so” cratering employee engagement.
Managers that foment resentment for company leadership and direction by constantly projecting their disillusionment and personal issues.
Managers that don’t know how to code or even how their own systems work or outright refuse to “be technical.”
Convincing a team of managers to also code and contribute directly even though the people leaderships parts of their job take 60+ hours per week.
Cross-functional partners (PMs, designers, customer support, account executives, whatever) that are doing their jobs badly and it’s affecting your team.
Support functions (SRE, Developer Experience, QA) that are run poorly but also tax all incremental headcount you receive. Negotiating and renegotiating headcount allocation to these functions.
Cross-functional partners with radically different priorities and no interest or incentive to align with you and the engineering teams more broadly.
PMs micromanaging your team and stepping on the toes of your engineering managers. Bonus points if the PM is really bad at engineering management and its actively making the team run poorly.
PMs/TPMs creating excessive processes and ceremonies that slow down your team and create the appearance of work without actual progress or results to show for it.
PMs without any product strategy and unwilling to take any feedback or let engineering fill in the missing strategy.
PMs with a terrible product strategy that engineering leadership politely ignores while doing their own thing.
Engineering leaders letting a PM’s “pet project” get staffed knowing full well it’s a terrible idea and not worth the team(s) that will be sacrificed to make it happen.
Large market-, location-, and macroenomic-driven decreases to compensation. We’re talking 10-40% decreases in total compensation.
Withholding yearly bonuses due to individual or even company-level performance misses.
Delivering and backing performance results you do not agree with.
Shielding an employee from adverse action that is wholly unjustified and an overreaction to a minor mistake that caused no harm5.
Trying to retain a critical employee who walks into your office with a counteroffer for >=100% of their current total compensation.
Critical vendors and infrastructure providers going out of business.
Critical open source dependencies going closed source, changing licenses, or losing all maintainers.
A sev0 security vulnerability is discovered that is being actively exploited.
A security researcher is threatening to publicly disclose a sev0 vulnerability faster than you can possibly fix the issue.
You have permanently lost or destroyed customer data with no choice but to beg for forgiveness (and/or spend $millions on data recovery services that don’t work half the time).
A major whale ($xxx millions in annual revenue, important logo or reference for customer acquisitions) is threatening to churn. You build what they want and they churn anyways…all under your watch.
An employee is using their elevated production access to steal/exfiltrate customer information or just to find funny stories to gossip about and earn street cred.
An employee is using their elevated production access to stalk their ex-girlfriend (yes this really happened).
Finding out one of your employees is a spy for nation-state actors and was effectively raised in a lab to infiltrate your organization.
Dealing with audits by government and public-private partnerships where failure can result in going out of business or losing hundreds-of-SWE-years to closing perceived noncompliance.
Interpreting compliance standards and government regulations. Determining how they impact your business, and organizing an effective response.
Rolling out a necessary breaking change to your product or API that affects hundreds or even thousands of customers and partners. Landing this without destroying your entire business.
A forced migration mandate that comes at the exact wrong time when your team has no resources or the “new thing” doesn’t meet any of your needs. The owners of the platform aren’t willing to compromise or meet your needs.
An internal platform you depend on decides it’s deprecated and their VP tries to dump it on your lap and make it your problem because “you’re the biggest user, so you maintain it!”
You inherit a team of lifers (people who have been at the company for 10+ years) and must somehow break and change all of their accumulated bad habits.
You inherit a team with serious issues (operations, reliability, code health, velocity, etc) and must design and land a turnaround effort in a fixed amount of time with no formal support from leadership and partners actively escalating every mistake.
You inherit a team with a terrible reputation with partners and stakeholders. The bad reputation immediately poisons the entire org against you and all of your ideas.
You have a very good idea but, because it’s vaguely similar to someone else’s previous boondoggle, you can’t convince anyone to give it a try.
Employees dealing with personal crises including divorce, death of a partner, miscarriages, or medical disasters.
Employees that are having back-to-back children and go on a string of paternity/maternity leaves lasting 3+ years.
Employees experiencing psychotic breaks. I have had multiple employees have their first schizophrenic episode at work (the typical onset age is mid-to-late 20’s after all).
Employees that show up to work drunk…and then openly admit that fact in the 9 AM standup while slurring their words.
Employees that become violent or irreconcilable after receiving bad news…having to covertly page security while trying to talk them off a ledge.
Employees that have brought weapons into the workplace (large knives, guns) and make vague allusions to having/using them in tense conversations.
Employees sexually harassing each other. Employees from different reporting lines harassing each other. Harassment cases being brought forward 2-3 years after the fact and HR being utterly unwilling to acknowledge or take action.
Manager-report sexual relationships…even fully consensual, loving relationships that turn into marriages. Moving employees around to fix/prevent conflicts of interest.
Employees dating each other, breaking up, and then not being able to work together or remain civil. Bonus points for a full-blown employee love triangle.
Employee accidentally screen shares pornography, at best permanently destroying the vibe of the team and at worst leading to a sexual harassment claim.
Employee that pays personal bills on the corporate credit card. Employee that submits an expense report from a strip club.
Employees that steal intellectual property as part of exiting the company.
Employees who WFH and are married to employees of competitors who also WFH.
Talking to the press, representing the company in a paper of record, speaking at a conference, or talking directly to high-profile customers who are both technical and non-technical.
Dealing with the leak of a top-secret feature months before launch due to something stupid like a string or enum constant compiled into a binary.
Back-to-back major/huge production incidents that get covered on the front page of a major publication (NYT, The Verge, Bloomberg, etc). Orchestrating and leading a major turnaround effort to solve such issues even when there is no executive appetite for funding such a large initiative.
Convincing someone to take a new role on a different team, or a role they are not excited about, because it’s what’s best for the company.
Joining a new org and immediately having your job changed to something else you would not have accepted otherwise.
Reorganizing a team to comply with org design mandates (depth, span, location, etc) you do not personally agree with.
Inheriting a large org (100+) and being immediately forced to conduct a reorg with zero context or personal on-the-ground knowledge of the new team. Landing said reorg in less than 30 days without disrupting any in-progress projects.
One of your peer leaders quiet quits and you’re forced to dotted-line manage their entire org so that your own project/goals don’t implode.
One of your peer leaders is so bad, all of their directs are coming to you for mentoring and coaching…doubling your effective number of direct reports.
A peer reneges on a commitment that dooms one of your projects because a new SWE or PM leader came in and flipped the whole roadmap upside down.
A peer tries to convince your manager you should report to them instead. A peer tries to convince your manager to steal one of your teams and give it to them.
A peer renames one of their teams in a way that creates an implicit land grab, overlapping with part of your scope and creating uncomfortable conversations about reporting structures and project ownership.
You become the boss of one of your peers who is upset they were passed over for the same role and does not respect you.
You elevate a member of your team, enraging their peers who believe they should have been picked instead.
You delegate a high-impact project to a trusted report. Your other reports become jealous and upset, believing they were entitled to that project.
You own legacy systems that no one understands. There is a major incident in said system and the whole response team is just guessing-and-praying their way through the incident.
Your boss or a peer commits the org to a massive initiative without consulting you, while also supplying a cost estimate and delivery timeline that is wildly out of alignment with reality.
In response to a resource crunch, your boss says you’ll just have to reprioritize your roadmap to make it work. They refuse to help soften the message with their cross-functional peers leading to an outright war between product and eng.
A critical employee has their promotion shot down by committee and you have to find a way to retain and keep them engaged.
Said employee gives up and effectively goes cold fish, falling from HiPo rising star to PIP in a matter of weeks.
A peer tries to promote a “toxic 10x’er” that will inevitably destroy the company, it’s culture, and team morale. Everyone is on board with the promo and you’re the only person in the room advocating against them.
Running a product discovery process, design sprint, or POC spike, leading cross-functional peers to define an entirely new direction or initiative without formal support or sponsorship from the org.
Fixing a broken product/technical strategy when you don’t have formal authority over the strategy. Bonus points if your boss thinks capital-S “Strategy” is a waste of time.
You launch a feature and the user feedback is poor, the data shows conflicting results, and the press lampoon your product. You must successfully pivot and recover in a matter of weeks or your boss will pull the plug cementing defeat.
An executive forces you to launch a low-quality, unfinished feature and whitewashes the narrative for their own gain. You are left cleaning up the mess and will get no rewards for that because “the project is done!” so all of that is invisible work.
Your boss or a peer lies to you, convincing you that “the CEO said we must do X” or “we have an important VP-level review coming up” causing you to burn personal credibility to get things done faster.
Your boss is fighting with a peer leader and using your team or project as the battleground…delaying decisions, pushing back delivery dates, removing staffing, and generally doing anything other than worrying about the actual customer.
Your company enacts a hiring freeze and zeroes the travel/fun budget causing massive employee anxiety. As people quit, you don’t get any backfills.
You must layoff >=10% of your workforce, and also pick the victims on your own with less than 1 week to turn in your homework.
You must outsource an existing function staffed by FTEs. You are personally responsible for identifying, selecting, and managing the outsourcing agency.
You must rebuild an existing team in a cheaper location (India, Brazil, Poland), including somehow bootstrapping a hiring pipeline in those locations with limited support.
You must close an entire office and either relocate employees or force them to WFH. You must not only deal with the mechanics of the staffing changes, but also all the procedural aspects of evacuating a building.
Your directs are not growing fast enough so you hire in a more senior leader so you don’t drown. You must somehow convince your existing staff that layering is not the end of the world nor does it cut off their avenues for career growth.
Your boss quits, is laid off, or fired unexpectedly, forcing you to rebuild credibility with an entirely new cast of stakeholders. Bonus points if it leads to you getting reorged under a peer that you and your boss previously hated and with whom you were in open conflict.
A manager on your team quits or goes on extended medical leave, forcing you to manage 20-30 direct reports. Bonus points if it overlaps with annual performance reviews, promotions, and compensation planning.
Your boss quiet quits and just starts passing everything off to you unfiltered. You are now on the hook for way too much and half of it makes no sense.
Purchasing COTS, including negotiating a contract with the vendor, running a proper bake off, dealing with dog shit account reps and sales engineers, and getting the budget approved when no one in your org has bought something externally in 10+ years.
Buying or renting physical datacenter space. Figuring out the mechanics of actually paying for this in your labyrinthian purchasing organization.
Prepurchasing cloud capacity and trying to forecast compute demand for a feature you haven’t launched and have no historical data to anchor your estimates. Getting it wrong would be a disaster (underbuy == can’t launch; overbuy == go bankrupt).
Determining a production incident is actually caused by a Cloud issue, and escalating an incident to AWS/GCP (who are famously super accessible and not prone to just ignore you / blame the user / route you down endless phone trees).
Building personal connections with high-ranking engineers in AWS/GCP so you can call in favors when the above inevitably happens again.
Going full Karen on a vendor when they breach SLA or otherwise screw up your business and extracting an ounce of flesh (discounts, favorable renewal terms, SLA penalty kickbacks, etc).
Creating an industry alliance, taking control of, or otherwise influencing a standards group to ensure it supports your business objectives.
Leading a total rewrite and migration of a mission critical system.
Taking over a struggling rewrite/migration project that is multiple-years late and actually finishing the thing.
Inheriting a project that costs 50+ SWEs and has been running for 3+ years that you fundamentally disagree with and somehow navigating the sunk cost fallacy when sunk cost is measured in the hundreds of millions of dollars.
A new policy is implemented, causing a multi-year initiative to get blocked during launch readiness review and threatening a multi-quarter delay.
The annual employee satisfaction survey reveals deep dissatisfaction and unrest that you were otherwise not seeing in day-to-day interactions.
A product launches just to immediately discover a P0 bug or security vulnerability. The launch had so much PR and fanfare attached to it, it’s impossible to rollback.
You discover a major bug or data issue that has been hiding for years that calls into question hundreds of decisions and assumptions.
Determining when to utilize contractors. Selecting suppliers and managing contingent workforces. Firing contractors that do not meet your expectations.
Having a recruiter lie to you and misrepresent a candidate’s credentials in order to get their friends hired.
Hiring someone only to have a completely different person show up on day one because they paid someone to take the interview for them. HR will not let you fire them, meanwhile they fall short of expectations and require constant management.
Negotiating with a peer to take ownership of a legacy system.
Negotiating with a sister team to let you contribute a feature/fix to code they own.
Getting an item prioritized on a peer’s roadmap when they are under strict orders to say “no” to everything.
You get a new manager with a totally different approach to management that you know will not work (you tried it before), but who gives you a strict deadline to refactor your team and ceremonies anyways.
A report gets into a fight with a peer. The relationship decays to the point that neither party is willing to negotiate or compromise.
You flag to a peer manager some rude, hostile behavior towards your team. The manager suggests that your team deserves it because they are incompetent.
You have a team full of Ukrainians when the Russia/Ukrain conflict breaks out. You have a team full of Jewish people/Palestinians when the Israeli–Palestinian conflict heats up. Nothing in manager training prepares you for an employee answering “how’s it going?” with “my hometown blew up.”
You have a team of Indians who are covertly implementing caste discrimination in the US.
You build a platform that would be useful across the company and must convince your peers to adopt said platform.
Someone else builds a platform they think would be useful, but it’s not and would be a waste of time to adopt. They attempt to use an org-wide mandate to force the issue.
You make a promise or commitment to a peer assuming you can make it happen…only to have your boss overrule you or suggest the exact opposite.
Your peers have technical beliefs that are antithetical to everything you know about building good software. Convincing them of anything is an uphill battle.
Someone claims credit for something you or your team did. Attempting to call that out just makes you the problem.
Your report has a completely skewed view of reality and assumes the worst in everyone and everything. Bonus points if this was the result of an unchecked rumor circulating through the org.
Your report is underperforming but fundamentally disagrees with your feedback.
You have a very senior report (senior staff/principal/whatever) that has needed to be fired for years but has been smart enough to out-maneuver the last 5 managers who tried. It’s your turn.
You have a manager that needs to be fired but, because their team is relatively competent and carrying them, it’s difficult to produce sufficient evidence to convince HR.
Your employee has saved up 3+ years of vacation and takes it all at once, disappearing for an entire quarter.
Your HRBPs only quote policy at you and don’t actually collaborate to solve problems.
Acquiring companies including running technical due diligence. Running due diligence when the company is clearly trying to cover up problems so you don’t buy a lemon.
Getting acquired including answering due diligence questions. Having your CEO pressure you into concealing problems so you don’t blow up a deal.
Planning and leading post-acquisition integration projects.
Running a successful offsite that isn’t just an excuse to expense a bunch of fancy dinners and liquor.
Bonding a new senior leadership team and creating psychological safety amongst the most competitive subpopulation in the entire corporate world (middle managers).
Upskilling and developing the capabilities of a large team; scaling beyond individual 1-1 coaching.
Hiring and importing external talent to inject necessary cultural attributes, technical know-how, and leadership traits into the team.
Building your own hiring pipeline when centralized recruiting and sourcing let you down.
Running your own bootleg interviewing process when the centralized interview process is too lax and passing bad candidates.
Detecting and filtering out internal transfer applicants who are evading performance management.
Detecting when a peer manager is trying to pawn off a terrible employee onto your team and actively concealing performance problems.
Company- or org-wide pivot into a new area, product line, or strategy requiring a complete overhaul of team priorities and responsibilities.
A venomous snake gets into the office and somehow it’s your problem because…manager?
Dear reader, I have dealt with every single one of these in the last ~5 years (that’s >30 per year…and a lot of these happen on a recurring basis). I literally made this list by just mentally recounting all my screwed up experiences. This is not theoretical. You must be both intellectually capable, resourceful, connected, and emotionally prepared.
Oh, by the way, thanks to ✨GenAI✨, do all the above while also pushing 5-10 PRs a week because something-something-managers-are-technical. Lord have mercy on us all.
So, returning back to the original premise. When you ask for greater scope and a larger role, what I’m really judging is whether you can deal with all these things without my help. I’m using previous situations you’ve handled to benchmark how you show up when the going gets rough and how well you’ll ad-lib your way through the inevitable novel curveball.
There’s a lot of vibes and assumptions built into that snap judgment, and trying to compress that down into actionable feedback is borderline impossible.
Passing the “can you hang?” test
Even if you’ve done all of the above, there’s still one more hurdle to clear. This is the fuzziest and most damning criterion of them all:
Can you hang? Do I actually want to talk you? Does talking to you lower or raise my cortisol? Do your fellow senior leaders want to talk to you? Or do we all just tolerate you in exchange for some amount of finished work product?
Look, I know this sounds horrible. Please don’t cancel me, this isn’t my invention but rather just how the world works and I’m trying to give an honest blueprint for breaking through the glass ceiling.
Getting promoted into senior leadership means I have to spend A LOT of time with you. Your peers have to spend A LOT of time with you. The job is mostly upwards and sideways: aligning with peers and leadership on where we need to go and anticipating problems that would stop us. If I have to filter myself, or code switch, or do a lot of breathless exasperated preaching to get you to do anything, or generally put on a performance in front of you, that’s exhausting. Why would I opt-in to that fate?
Moreover, for my job to be possible, my closest confidants need to largely be on the same wavelength as me about what the job is, how to approach it, and what excellence looks like. I don’t have time to teach or convince you. That doesn’t mean being a “yes man” but we better hold a lot of shared beliefs, principals, and context so we can approach disagreements from a common lexicon.
A corollary to this: can you talk to my boss without embarrassing me? Everything you say or do reflects on me…especially if I’m the one who promotes you into senior leadership. On multiple occasions I have been Slacked by my boss with a screenshot of some coked-up nonsense a report has sent them along with “?????”
Last, but certainly not least, is remaining cool under pressure. You must have extreme emotional regulation and reserve your outbursts for private moments and safe spaces. You lose all credibility with key stakeholders and peers when you appear tilted. Your team will become anxious and distracted. I will start filtering and censoring what I share with you to avoid multiplicative hysteria which will be the beginning of the end.
Being in senior leadership means getting a steady drip feed of nightmare-inducing news delivered to your inbox. To thrive, you must value conflict as inevitable in relationships, comfortably hold conflicting/opposing ideas in your head, and flex your approach/beliefs/identity depending on the situation. Fewer than 1% of the population has the emotional regulation to do this according to some adult development theories.
When will you be ready?
You are dissatisfied by the status quo and actively seek challenges to do what’s right for the company. You can identify these opportunities and pursue them without anyone spoon-feeding you.
You have accumulated a repertoire of experiences handling the dark side of management. You can juggle tens of these things simultaneously and even delegate/coach your managers through handling most of them.
You show up as a true peer to other senior leaders and your boss…someone they seek out as a source of calm, support, and camaraderie…someone with whom they look forward to scheming and have confidence can turn talk into action.
Everything I’m describing here is judged in the eye of the beholder which is why there is some truth to the importance of visibility, reputation, and brand. That said, getting fixated on appearance management and self-promotion misses the real issue: the gap in experience and demonstrated ductility in the face of disorder.
No single project or moment will flip the switch from “not ready” to “ready.” Take stock of the sorts of experiences you’re missing, and then seek out the discomfort of confronting such situations head on. Switch teams and switch companies if you have to; do not wait for your manager to deliver these opportunities on a silver platter.
The professional brand conversation sounds so ridiculously fake and insincere, try not to rage quit when it happens to you. It’s a polite way to say “you’re a milquetoast beige blah and no one important has really noticed your existence or understands what you’re really good at.” Buck up buttercup and get more aggressive.
Please for the love of god stop spinning up "<engineering|production|operational|whatever> excellence" programs: they burn your time, TPM time, and engineering focus in exchange for paper thin results...all dressed to the nines in unctuous slide decks that make me die inside. Running horizontal programs is a real skill and half-assing it is just convincing me you're SUPER DUPER not ready.
Few write publicly about how they navigate these category-5 shitstorms, and when they do it's the cleaned up PG-13 version. This is part of the reason I started the blog and write so candidly.
I once had a manager let two different people on their team move to and work from a different state because it would let them land a flashy project faster than backfilling. We had strict in-office RTO requirements and location-based comp which meant they were overpaid and we were not paying taxes in the right state. We even had multiple employees commuting 2+ hours to remain compliant with these rules who become radically upset at discovering this.
Someone once used the CEO's numerical user ID in a test case as a cute easter egg...resulting in the security team filing a formal grievance that led to their end-of-year rating being dropped due to "policy." This cost them about $50k in incentive comp they would have otherwise received.