You’re Not Ready
The Hidden Resume of Senior Leaders
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.
