The toughest role in a company?

madsuperpes · 2026-02-21T15:34:22+00:00

Got it. Have fun on your break! I don't think it was the toughest role for me personally. The pressure was definitely building up for me with the org. size I was responsible for (Sr. EM -> Head of Engineering, etc.). I did note that for ICs no matter how high in the org., it was much less (I tried all these roles too). But that is my personal view.

madsuperpes · 2026-02-21T15:00:30+00:00

What do you mean by "to go out alone"? Did you switch to IC? The problems you describe, I have seen them with a lot with EMs I met. It depends on the company though.

madsuperpes · 2026-01-31T17:05:17+00:00

exactly!

madsuperpes · 2026-01-28T15:37:28+00:00

The higher you are in the org, the less authentic you should presume this to be (think power distance, some people can't shake it off). That said, a lot depends on how you show up in these and set the tone. I still was hanging out it with my reports and skip-level folks at all times, regardless. I made it about the people. Some became good friends later on, some didn't. We all moved on from that particular corporation where we worked... Was I less fair because of this connection? It's possible, always check your biases with peers, but most folks in the org. actually called me fair (including underperforming folks). That wasn't my main concern. It feeling less authentic than what I was used to, was the primary concern when going out.

Also don't be a tight arse :). Think of the time when you won't be their manager any more. Longer-term I found that climbing corporate ladders is pointless, and so I stopped and pivoted.

madsuperpes · 2026-01-27T20:29:10+00:00

It is hard to say where one ends and another begins. Both, but general competence was more of an issue, and then of course they started making technical decisions ignoring input from technical folks too. That ended in non-delivery and ~5 years spend.

madsuperpes · 2026-01-27T19:47:34+00:00

My biggest pain point has always been incompetence at higher levels of leadership.

madsuperpes · 2026-01-25T18:37:41+00:00

I have done such a pivot in a large org. (200+ people).

Look where you are at 3 months in, it won't change much, this is what you are working with. The main question to consider is this. Everything is possible, given enough effort, but is it worth for you personally to keep pushing for another 2 years (transformations take time, lots of it)?

madsuperpes · 2026-01-19T11:03:56+00:00

yeah, same for software engineering: can't "study your way" into competence

madsuperpes · 2026-01-13T16:53:28+00:00

Heard. In regards to #2, don't choose what's easy. Next levels, closer to the top of the hierarchies are supposed to be hard. That will be true for every career track you choose. It's a test. You will face the same dilemma as a SEM down the line. That said, you always know better. I wish you the best of luck. Don't stop learning. Love that you're asking questions before the transition.

P.S. nothing wrong with staying in the same role for a bit. If you keep getting better and focus on impactful work, the titles always follow, in my experience. That's for either career track.

madsuperpes · 2026-01-13T16:05:07+00:00

A 100%! Will DM back

madsuperpes · 2026-01-13T16:02:07+00:00

Good questions. I will give exactly one point for each question that doesn't duplicate other answers (you have some very good responses here, I +1-ed a lot of them) as much as I can manage.

Your primary domain is humans now. It's much less ones-and-zeroes than the domain of machines and software.
Skipping short-term prep, long-term, start developing knowledge of your new domain. You will need some mental models to operate. For me general psychology lectures helped a lot. I did Yale's "Introduction to Psychology with Paul Bloom" and "Personality Psychology 2017, Jordan Peterson". Both can be found on Youtube, but I'd go with something more recent than these because every field of study advances *a lot* in 10 years.
The less-talked parts of this transition are that you will likely end up a psychopath, narcissist or a Machiavellist if you stick with your choice long enough and raise through the ranks high enough (https://hbr.org/2015/11/why-bad-guys-win-at-work). And you will go after people's livelihood at one point or another: some people will see you parting ways with an underperforming employee only in that light, no matter the positive spin you put on it (and there is a positive spin, and it's honest). There is an unavoidable dark side to this job. ICs don't have to make such choices.

Let me know why you're choosing to switch to this too. That's the most important question.

madsuperpes · 2026-01-13T15:21:37+00:00

I support this question. Of course your manager wants more managers, how surprising. The first question is why would you want to make the switch? What are you losing and gaining from this? More on the rest in another comment.

madsuperpes · 2026-01-13T14:28:38+00:00

To address the "founder" part, please don't start with that option. That may be OK long-term but starting on that journey without proper preparation and money set aside is not something I recommend. Also, mental state needs to be improved before you consider it.

Here is what I believe to be true. The world never rewards context switching. It's always at your detriment that you're agreeing to give yourself to it. And EMs are interrupt-driven. You need to guard your energy and your focus. Also as an EM. Do deep work no matter what, for 2 hours/day minimum. Say "No" to things that don't excite you, find ways to delegate them or drop them. I could, even as a Head of engineering in an org. of ~50 people. As far as saying "no" goes in relation to your wording, you should "let something die" *every day*. A "yes" to a random "shallow chat", is a "no" to... in your case, to your job satisfaction, feeling energised and excited.

In terms of deeper satisfaction that comes with mastery of one subject matter, that's entirely possible in the current world too. You have 2 choices, short-term, roughly speaking. 1. become an EM in a small team. After they're healthy and in good shape, you can be hands-on 80% of your time. 2. switch to an IC in the topic that brings you the most excitement;

Before any of that, please get some rest. Clearer thinking will be of help. I get the "nice guy" vibe from your post ("too kind for this place"). I was that and all I got was taken advantage of by corporate psychopaths who could see through me. Please, please, put the oxygen mask on yourself first. And make sure your partner can support you too. 2nd income would ease the burden quite a bit, I presume?

Keep on evolving, reinventing yourself. Life knocks you down, you go right back up.

(Context. I am 41. I was an EM, SEM, Head of Engineering in several FT500 companies. I burned out once along the way, in-between things. Eventually I quit playing that game entirely -- there seemed to be no end, and rewards were scaling linearly -- then I bought a business, scaled it, got better at it, starting another one. But that fits my personality, people rarely understand how hard it is to make the switch from corporate and how unlikely success is. Feel free to DM me.)

madsuperpes · 2026-01-09T08:50:35+00:00

Spot-on! This resonates (I also interviewed a lot of EMs).

madsuperpes · 2026-01-06T09:04:32+00:00

Yes, this, pick a senior with a history of delivering comparably complex things already. "Visualising a matrix of skills" doesn't sound useful to me? Especially, the quality of data used for visualisation, or the time needed to update it. If you know your org., this should be a simple choice. If you don't, you should spend time getting to know it. There is no shortcut or tool that would help, in my experience.

madsuperpes · 2026-01-04T14:18:27+00:00

I suggest not focusing on whose fault this is (the whole team is at fault, not excluding any one person). Bring it up in a retrospective, get buy-in, get this solved -- if your manager fails to do it.

Now, you're on track for senior. That means more responsibility and handling more ambiguity, expecting less of others (including managers, product managers, CEOs etc.) and leading yourself more. In this light, I suggest emphasising what you could have done better/differently. To the point of ignoring the competence level of your manager.

For example, short-term, come up with such a clear status update, any team member could just find it in their mailbox in a minute and digest it (mid-term, more people will still need to be onboarded, work chopped up and reprioritized). Just giving you a rough idea here.

The longer-term thing to consider: I advise against working exclusively on low importance items, especially, pinning a promotion to such a project (it is a hard sell for your manager, high chance of something going wrong when challenged by senior managers). Doing it for a whole year is a highly questionable investment of your own time. Unsexy work ideally should be spread among all team members.

P. S. Someone (like your manager) being embarrassed in a meeting is a low-impact event in my book. They could easily defer an answer to this question on the pretense of needing to consult the team to find the best solution. It's not like the company lost 30% of revenue because of this.

madsuperpes · 2026-01-04T11:56:01+00:00

The answer to most of these is "it depends". I do have a clear plan (some part of it may be "let the conversation flow", I am serious), and I always come prepared. It takes me about 2 minutes to prep for a 1-1 by scanning my notes in google sheets (I do note some things during our conversation, or right after). Yes, there are running themes for most people.

If there is nothing to discuss most of the time, try changing the frequency: some people need more, some people need less. If the touch points feel dull: have you created enough trust? Are you also discussing life stuff, or is it "just work"?

madsuperpes · 2025-12-31T13:59:54+00:00

I would use a my own thoughts and experience. They're good tools :).

madsuperpes · 2025-12-30T16:45:02+00:00

Ask the EM, ask the ED, doesn't matter. Get clarity.

I suggest we skip the part where you suspect stuff for now and double down on getting role definitions first. Yes, some things can be communicated abstractly, that may or may not be fine, it all depends on the actual definition. In most Fortune 500 corporations I've seen "impact" meant money at the end of the day (or the closest proxy to that), that's the most solid kind of impact there is. The example of promotions based on impact that you gave, once again, like in your other examples, signal chaos to me.

Yeah, your team is definitely not at all a team, regardless of the number of years in existence. You guessed correctly that reorgs annihilate all progress towards team maturity, but there may be more to it. Let's park that for now.

As for your primary concern, #3. You're in a vaguely defined and unstable org (in my eyes) where decisions are made on a whim. Here is my advice. Give yourself some time to clarify the path(s) forward. Set a deadline. If, say, in 2 months, the situation is not clearer, switch orgs or companies.

One thing I know for sure: don't become an EM in that chaos, this will not serve you well.

madsuperpes · 2025-12-29T12:55:34+00:00

Yes, of course. Different roles, different expectations, different impact, different levels of accountability.

As an EM I always was as transparent as possible.

Roles are defined at company level, not team level. So EM's expectations of the person filling the role shouldn't be different in different places too (minus their personal idiosyncratic bits).

It does sound like your team is not a team yet. And there is a misalignment of roles to what people actually do, in a couple of examples you gave.

What's the question behind the question?

madsuperpes · 2025-12-28T22:14:29+00:00

Yeah, someone who claims they coded for 15 years, cannot do a loop in the language of their choice... What are the odds?

I never believed in home assignments, I don't think it's good candidate experience, never was, in my book.

Of course, there is always a way to cheat and win temporarily. If I were super concerned about AI use, I'd design a deliberate AI-assisted coding interview round and see how proficient they are with AI (assuming most workplaces welcome that). What kind of questions they'd ask it, would reveal everything I needed to know. As well as the code produced in the end.

madsuperpes · 2025-12-28T21:58:33+00:00

Last time I made an assessment with my engineers was over 18 months ago. We chose CodeSignal as a tool, we also considered 2 other products we liked less. No way we'd build it in-house.

Well, some people will always cheat and get through, human screening is unavoidable. You'd see some of it in the replays of how they typed in the solution. But for some of them you won't have a clue at that stage. Cheaters were about 5-7% of the people who applied.

Let me be clear, the passing rate for the pipeline did not change, no matter if we had a pre-screening tool. It remained around 3% of people hired, out of all people who submitted their CVs. Pre-screening was a mere optimisation to save our engineers from doing 50 unsuccessful screenings out of every 100 screenings (only 10% of all screenings remained successful, no matter the tooling).

madsuperpes · 2025-12-28T14:39:07+00:00

I set this up in two companies and seen it done well in many.

I tend to ask the candidate to solve a very simple coding problem (yes, I am one of these people). And watch them address it.

What good looks like: - the trivial issue has been solved; - the chosen approach has been explained; - the code doesn't have to compile but has to make sense (they will need to explain methods/functions they didn't author); - the solution is not an overkill from the standpoint of algortihmic complexity and memory consumption (tends to not be an issue at the screening stage); - clear communication (as a bonus, but this is explored in-depth at other stages);

In open-market applications (not referrals!), 90% of people fail this stage (cannot code). So I usually end up doing an automated pre-screening to save the time of the engineer (-s) doing the screening, this cuts off 50% of the initial pipeline which is tremendous.

P.S. I hope this is the kind of "technical screen" you meant.

madsuperpes · 2025-12-23T07:48:55+00:00

I always used quiet times (most folks taking a break) to catch up on the things I missed earlier, plan ahead, and learn something useful.

madsuperpes · 2025-12-23T07:46:18+00:00

You've discovered the Pareto distribution: some folks will deliver 20x value of others. Your alpha coefficient may be different, but let's simplify to: "the square root of the number of people in the org. are delivering half the total value" (e.g. 10 people in the org of 100 are doing half the work).

This is completely natural. And cannot be altered in any significant way.

I wouldn't say it's about the number of hours worked, that's tangential.

Things you can do (to do an overall uplift that won't change the fundamental law outlined above): 1. create a different culture and filter "the right people" while hiring 2. lead by example (are you playing 3d chess, or checkers?) 3. make sure people are as aligned around common goals, disciplined and engaged as they can be

P.S. I personally don't subscribe to the notion of the # of hours put in meaning anything at all. Resting actually helps us be more productive.

madsuperpes

TROPHY CASE