What was your biggest leadership challenge of your entire career? How did you overcome it? What happened then?
Understanding that delegating tasks, instead of doing them myself, was of the utmost importance the more people I managed... especially, greenfield work. Literally: do not steal the fun. This also means inherently trusting people, and if you can't do that you shouldn't be working with them. two important notes about that:
1. If you just thought of someone you can't trust instead of thinking about how you can give more trust to people, you just had your ego stand in the way of mutual success. You are a shitty manager, and today is hopefully the first day of you recognizing that and learning to trust.
2. When people don't deliver what you expected, it's because you did a shitty job of communicating it to them. What seems obvious to you after 45 minutes in a meeting with three other people already prepared for the topic will most of the time seem obvious to no one else. If it does, I can almost promise, their vision of it is totally different than yours. Learning to work through the defining the problem (that includes asking "does this problem exist?") and then guiding solutions (we have x days, engineering hours, etc available) to ensure they meet the needs of the business. If no one but you delivers things correctly, you're a shitty manager, and today's hopefully the first day of you recognizing you need to learn to communicate and trust.
Not many people are lucky enough to be told so plainly it's their ego, but it's your ego that causes your team to fail. Maybe it's your boss's ego that's causing you to fail... I was told plainly to my face to not let my ego get in the way of the goal... and yeah it punched me in the gut too, so if you're hurting, or in denial know it's okay. We all have to grow, it's worth it.
> When people don't deliver what you expected, it's because you did a shitty job of communicating it to them.
Sometimes the person sucks beyond repair and needs to be fired.
If you have a competent person who didn't deliver what you expected, then yes, it's probably the fault of the manager's communication. Not so for the lower-end of that competence spectrum.
It might still be the manager's fault for hiring that person in the first place, but that's separate to it being their fault at not communicating properly.
The shitty job here is not firing that type of person quickly enough, and misdirecting the blame towards your communication skills.
EDIT - edited the first sentence for clarity.
Which is... also the responsibility of the manager. Q.E.D.
And who does that person report to? Who made the decision to hire them in the first place?
He wasn't bad as an engineer, but he had this crazy OCD to a point that even keys in YAML file should be ordered alphabetically.
He had his vision how things should be, and how he would implement them.
First, he was not happy that my solutions were done differently than what he would do.
Then, when I learned about that he wasn't happy and tried to do it the way he wanted by asking him question about it he told me that I required hand holding and as a senior should not need that. Yes I'm senior, but not a mind reader.
I would think that someone who majored in psychology would be better at something like that, but I guess the only thing he learned in psychology class was Socratic method, which he constantly overused when talking to others.
He though he was being clever but only made me think (because I couldn't say it to his face): "just fucking tell me what the fuck you want me to do"
Ugh, I'm so glad I don't have to deal anymore with this BS.
Eh, I am guilty of that (for myself, I don't run around other people's code).
I don't know if it's OCD but I clearly remember the moment I decided to order keys (in yaml, json, etc.): after a debugging session where I lost time because I was scanning whole lists with my eyes, looking for a particular key and thought "it'd be easier if it was ordered according to alphabet and not domains of concern".
Wasn't there a debate/online conversation about `girly code` a decade ago ? About tabs, alignment, etc ? Thank you prettier :).
I feel like this is more common among insecure managers than with secure managers. The insecurity shows up in micromanagement. Micromanagement takes many forms, all the way from verbal status updates to toxic code reviews to lack of coherence in project plans or career plans.
Until this recent manager, I never truly understood what micromanagement and insecure management meant. Maybe I was lucky to have good experienced managers in the past. Insecure micromanagement truly crushes my motivation to work.
If you haven't built trust with every person on your team, that doesn't make you a shitty manager. The more people you can work with and trust, the more effective you may be as a manager, but don't let a counterexample serve as proof positive that you suck. Trust is a two way street.
Sometimes people underperform for other reasons that have nothing to do with you. They may have a different perspective, or they may just be having a bad day. Or they may have family or health problems affecting them. Or, they may actually just no longer care or not be good at their job.
For the second -- it is on the manager to know enough about the reasons affecting their report's performance to be able to adapt before the team underperforms. (and it is on the report to surface that information quickly so that the team isn't compromised)
You can still try to find out what causes their behavior (by showing interests into their perspective) and may be able to help them and therefore the team.
- If they have a different perspective, it should be helpful to listen to their perspective.
- If they have a bad day, it will go away.
- If they have family or health problems, you might not want know the details, but simply knowing that a person is going through a difficult time might give you enough information to know how to improve the situation.
Even if you are not the cause of the situation, you might still be able to improve it as a manager.
This is the quality I learnt to look for in a leader (I am not a leader but worked under few good ones).
I also noticed how good leaders never take things personally. They quickly move on and not hold grudge. I am amazed how good leaders are able to do that and in doing so inspire me to do the same.
Is your advice to pretend you trust them? Some kind of "fake it til you make it" approach?
A general rule for me is that you should know within the first 2-4 weeks whether you've made a bad hire. This is a bold statement, but my experience is that this time frame will give you enough time to get a gut check (super vague, but there are too many different patterns for me to articulate here). If your gut says no, that will stick with you, and your gut will likely become a self-fulfilling prophecy anyways.
There are people who don't live up to the mark in terms of quality and that's that, and in those scenarios it would have little to do with trust.
The company I own got hacked and our database was stolen, containing basic user and company data for 100,000s of users as well as some partial card data. From the moment I discovered the breach (browsing logs after an unexplained brief outage), for the next 3-6 months, my life did not belong to me, but to insurers, forensic investigators, regulators, the police, credit card companies, press/media, and thousands of customers who emailed and called about it. Suddenly my life went from two or three people I would regularly interact with a couple times per week, to dozens of people who were involved in the crisis response, cleanup, and 'remediations' who I would speak to multiple times per 16-18 hour day.
Around the same time, I lost some close friends very suddenly - one to cancer, another to old age. And there was the whole pandemic thing. I still haven't been able to grieve properly about that.
You read about data breaches happening almost every week to various companies large and small, and mutter about how careless they were, or worry about whether you were personally affected. But from the inside, it is a totally different story for those involved (if they have even an ounce of genuine remorse and concern, as I did). Behind the scenes, they are an absolute shit-show. The truth is we had been careful and the hack was due to a compromised vendor, not our own code or networking, but I felt massively responsible and like the worst person in the world. I worked the 16-18 hour days in part to assuage my own guilt, but also because I had nobody else that could. The one saving grace was having good cyber crime insurance (which, I note, is now far more expensive than before - I'd pay it many times over, though).
I'm still not over the incident, and have regular therapy (and regular nightmares) with many days spent unable to really focus on anything. Burnout is real, PTSD is real, and I don't know if I will ever feel truly safe again - I certainly feel that I need to get myself off the internet as soon as possible, and away from any kind of business leadership role. I just cannot ever face something like that ever again.
Thanks
I understand how you feel now, but (I am sure) very many people out there would rather trust their data to (a future) you given how careful you have been, how much you have cared, and how much you have learned from this.
When you've been dream deprived for any reason -- lack of sleep, medication, drug use, alcohol -- and you resume sleeping more/better, you will have intense, vivid dreams and these often get interpreted as nightmares. This can happen for really prosaic reasons like you quit smoking or you cut back on how much coffee you drink.
If you know about that phenomenon, it can be easier to see them as simply very vivid dreams and treat them kind of like a roller coaster ride. Some people like roller coasters and pay good money for intense experiences of that sort.
The rest will definitely take time and effort to sort. But I'm hoping a little information here will make things slightly more bearable in the short term because if you were working 18 hour days and likely sucking down coffee to help you cope, that phenomenon of very vivid dreams is almost certainly part of what you are going through.
Yes, those dreams may well be focused on recent stressors. But the intensity per se may mostly mean "I'm finally getting more than five hours of sleep a night again." and/or "I've cut down on the coffee habit now that the drama is mostly wrapped up."
I'm working on a way to stop the "compromised vendor" problem. We have no idea what it's like on the inside when this happens. If you ever want to talk about it more I'd love to (sympathetically) have some idea. Not sell you anything, not "interview you" just learn.
You can contact me at dvhw at ABScott.com (not the domain of the company working on this -- really I'm not trying to sell you anything, especially at this terrible time).
I was so stressed I considered suicide despite the damage it would do to my fiancée and family. I didn’t see any way out of the situation and had convinced myself I was going to jail and my career was ruined. There were all sorts of suspicious emails, and truth be told I wasn’t exactly a saint either.
I wound up finding a therapist who specialized in criminals and those going to jail. He listened to my story and gave me very good advice, and said worst case I would go to low-security prison for a few months. He didn’t think (from his professional experience) that I would do any time, and to relax.
We wound up settling with the regulators, I left the company on semi-good terms, and eventually the company got acquired for the biggest exit of my career! And I am very happy I did not kill myself (as are my now-wife and kids).
The silver lining is normal stressful situations don’t rattle me anymore. I have ice in my veins given what I went through. I am now a CTO of a respected company.
At some point in my career (I've been doing software for 22+ years professionally) people started taking me really seriously. I could no longer make certain jokes and I had to be careful about my opinions because they were taken (in many cases) as "the right thing to do".
So I got in all sorts of trouble, because I didn't want the leadership at the time. At some point I finally embraced it and actively started figuring out what kind of leader I should be.
After that point, it has gotten a lot easier. I even started enjoying it.
Leaders lead even when they don't intend to. So if you're one (willing or not), you should take the responsibility do your best to make the team thrive.
I think it as: Company > Team > Self in terms of goals, if I cannot accept that, I'll move on to a different gig.
When I just had peers and made a stupid pun, my friends/coworkers would just groan and tell me not to quit my day job. But when people's annual reviews are in your hands, it's a different story. I think it's perfectly fine to open a meeting by lightening the mood with humor, but I feel compelled to generally reign it in.
Keep the 'bad puns' though, that's more of an expression of humility than anything and it gives them an excuse to groan.
Everyone 'hates/resents their manager' just a tiny bit, and a little opportunity to groan but not get too serious about it is a nice valve.
And yes - the greater the power, the greater every little thing gets parsed and possibly taken out of context, I loathe that because it's the thing that stops us from being candid, and why even in the long-form podcast world, people are not truly forthcoming.
"Lead, follow, or get out of the way." - Thomas Paine
Falling into leadership means that people respected you enough to either follow or at least get out of the way.
I just never have managed to enjoy leadership in the official sense. Natural leadership, e.g. being looked to for advice, generally followed is one thing. Official leadership, e.g. meetings and planning is for the birds in my book.
This happened to me. It led to some problems though. People from other teams would contact me as the tech lead (was a midlevel dev acting as tech lead) and ask me to do stuff in PRD. I'd like to help, but only official tech leads are granted that access...
Can you expand on this? I'd love to hear your thoughts on this. What sort of leader did you become? I don't even know what kind of leaders there are.
I care mostly about the personal growth of my team, I firmly believe that if I help them be the best they can be, the world will be a better place (even if it means losing some of them because they realize they want to do something else, the world will still be a better place).
This means sometimes giving advice, sometimes teaching, and sometimes getting out of the way and let them do their thing (even let them fail, and help them learn from the failure).
The scope goes beyond technical advice, I help them frame problems, think about what they want and what they really care about, it's a mixture of counseling and a typical tech lead.
The trick is doing it without making it forced or weird. It took a lot of exploration of my own emotional state, being able to empathize a lot, and allow myself to be vulnerable. This helps building strong, honest connections that I truly think get the best out of people.
Along comes my first day and surprisingly, it’s mostly radio silence. CTO, my boss, doesn’t respond to my emails, doesn’t answer the phone. I call the CEO and he promises to sort it out.
Fast forward a week or two later, something is obviously up. Long story short, the board fires the CTO, making me the most senior engineer in the company. Yikes, but ok. The contract with some of the consultants are up a week or so later, and they choose not to renew. Weird. The only other FT engineer quits. Uh-oh. I’m now the only engineer. I had to learn a new product and code base. The support backlog was long. I was getting called into sales calls.
If I had lived in a tech hub, I would have quit. But I didn’t, I lived in a remote mountain town and finding this remote job took months.
I ended up lasting about 18 months. It was a learning experience, but horrible on my body, relationships, mental health.
It can be that hard to find remote jobs? (I never tried.)
Can I ask how much work experience (eg years) did you have at the time?
I'm glad you could get away from there eventually. (Hmm you found another remote job?)
I'm a developer at a fairly small company. I never really wanted to be managing people but after some internal drama a bunch of stuff was moved around and I found myself in charge of the team I had been on while we looked for a permanent manager.
One of the devs who now reported to me decided that this was the best time to demand a raise- not just a cost-of-living increase, which are scheduled, but an amount of money that would have made him the highest-paid person on the team by a lot. (He was on the lower end of both seniority and performance.) He was threatening to leave, and after talking to my superiors I basically just said "sorry, you aren't getting that, I don't want you to leave but if you do I will be happy to give you a good reference."
That didn't go over great and he emailed the whole C-suite trashing me and telling them essentially what a mistake it was that I got tapped to lead the team over him. The CEO just forwarded the email to me and said "deal with this." We'd had a pretty good relationship before, (or at least I thought we did) but all attempts to sit down with him and figure out how we could work together ended with him just making it clear that he was not going to play ball.
He stopped showing up to work for awhile and sent his notice not too long after, and eventually we hired a real manager (which was always the plan) and I went back to writing code. Even though I don't know what I could have done differently I still feel bad and think about it a lot.
If anything, you should have fired him intentionally yourself when he went over your head. He isn't looking to work with you or the team, he's actively seeking to undermine you; at that point his presence is a negative, not a positive.
Is escalating an issue a fireable offense?
If it helps, consider that this person might have tried exactly the same ploy with whoever was in your shoes. I'm sure they had some issues going on in their life, and issues with the existing management that you inherited unknowingly.
Management stress is real. Part of it comes with maintaining confidentiality, whereas a disgruntled employee will rant and get things off their chest.
I won't say it's 100% about the role and not the person, since that's dumb - interpersonal relationships are real and significant. Equally, it's not 100% about the individual. FWIW, and taking your description at face value, I think your response was appropriate and theirs was not.
People are weird - all of us.
We get into our own head-space, and we interpret the world differently than others, sometimes objectivity falls by the wayside.
Sometimes someone is truly working is rear off advancing the mission, but but that nobody really noticed, or if they did, that it didn't matter because 'hard work' isn't necessarily the only management requirement. They get upset because they didn't get the promotion.
Lashing out at 'management' is the easiest, most common thing for any worker to do, often there's a basis for concern, but just as often people don't recognize how inherently chaotic it is the higher one treads.
The moment you're in a leadership position, you will constantly be challenged by at least one 'hard case' of some kind or another.
Once simple rule to help differentiate: if they are making a fuss about the product, or something that will help the company/team, then there's probably good faith there. If the fuss is always about themselves or their career, that's not good.
I had no budget, no control over any of the issues, no authority outside my team, no time... nothing. It was made clear to me that there would be no support in any way. I was young(er) and tried my best but it was a shitshow. I have never felt more exposed and thrown under the bus.
A couple of similar situations were enough to grind down my resolve and I became as disillusioned as everyone else. When the inevitable redundancy was offered I took it and left without hesitation.
Still bemused by how absolutely amateurish and vindictive the situation became.
So I didn't "overcome" it, clearly, but it helped me realise a few things. Firstly, that nobody has any idea what's going on in anyone else's head. God knows what my then-boss thought of me, but it clearly wasn't much, and it clearly didn't match how I thought I was perceived.
Secondly, once things are toxic it's almost impossible to turn things around. A couple of other people at the same place acted very poorly too, around the same time. Looking back, maybe I should have just quit. But it wasn't easy to see the wood for the trees.
Third, stick up for yourself and for others. Don't be an arsehole. Everyone's dealing with their own demons and people in authority should constantly try to remind themselves of this. Support each other and grow together. Fortunately most people aren't arseholes, even if some occasionally act like they are.
I haven't always got those elements right, but at least I'm aware of them.
So I guess what I overcame to a small degree was my own professional shortsightedness! :)
No experience with that whatsoever, and no support structure to lean on as we were basically one of first gen IT startups in my country. No established processes and we had to invent them as we go. I had read zero books on technical leadership and didn’t know anyone who I could talk to. Didn’t know which books I even had to read as there wasn’t anyone to talk to. HN was my only solace.
I was working like crazy and putting out fires, but instead of helping my colleagues I leaned too much into doing the technical challenges myself.
And it all came crashing down when I went on a long overdue summer vacation. On the first day I start receiving emails in the form of “um we seem to be having a problem, not sure how to deal with it”. It kept escalating day by day, and at one point the CEO just told me “sorry mate but we need you back” and I had to cut my vacation by half and get back to work.
On the bus ride home I kept thinking “never again” and when I got back took a _much_ more serious effort to make sure I wasn’t the single point of failure and actually be a CTO.
Read some books, took some steps back, mentored people, and most importantly actively took less challenging things so others could shine too.
And it worked, I mean I wasn’t that great a leader I’m sure, but there wasn’t a problem that my team couldn’t handle without me afterwards.
Ended up quitting a couple of years later as I was burned out and not happy with the direction of the company overall, but the team is still there more than five years later and growing.
What I learned was that you have to take new responsibility seriously and try to teach yourself for it, not expect things to just “work out”.
I‘ve had/have a similar experience. No seniors here to learn from but got it up to top performance with reading (joelonsoftware was a great inspiration back then), investing lots of time (but rarely overtime) and being ambitious.
I believe you also learned that you shouldn‘t be the single point of failure. I‘m still actively working on that. Though it‘s hard to relay to others if they just can‘t get it done or don‘t share your ambitions, vision or views of quality and customer focus. But there‘s always hope.
“If you want to build a ship, don’t drum up your men to collect wood and give orders and distribute the work,” he said. “Instead, teach them to yearn for the vast and endless sea.”
Heard that recently in Julia Galef’s TED talk which I think was awesome.
But I also struggle with that last one myself too. At least now I know inspiration is more about emotions than rational arguments.
It only afterwards turned out to be a challenge. I didn't have an alternative job offer at the time of quitting, and shortly after my last day at work the pandemic started.
What happened after that? If I can ask
Not only was he dead weight, he destroyed the team's morale and hurt their relationships with other teams. The team looked to me to solve the issue and couldn't understand why he wasn't being fired, and I couldn't tell them "I'm not allowed to fire him".
I spent months working with him on improvement plans, coaching, and mediating with no improvement, and in the end managed to shake him off in a RIF.
I stayed long enough to repair the team's morale and strengthen the hiring process, and then quit as I had completely lost faith in the company.
Also, I'm not sure if you tried this, but I've heard in cases where you can't fire someone, you recommend them for internal transfer and give the other manager good reviews of them. It's a bit scummy but it's the most positive outcome for the team.
I don't want to ignore the question, but it's a sensitive topic and I'm not sure bringing it up would add to the conversation.
> Also, I'm not sure if you tried this, but I've heard in cases where you can't fire someone, you recommend them for internal transfer and give the other manager good reviews of them.
Yes, I actually had a peer recommended this as well. In the end, I decided against it as I felt it was unethical. I didn't want to get rid of a problem by becoming one myself.
You can try and create a bubble of goodness in your own team, but you still exist in a sea of shit. Eventually that sea will drown you.
You can selectively “seed” your personal problems with EAP to establish documentation of stuff and use that to make termination difficult or delay. Some people will go so far as to make claims of alcoholism and parlay that. Gumming up the works is effective, as one HR screwup and the employee is good to go. Sometimes you can get promoted for being an asshole.
Edit: the company lasted maybe 2 years and barely fed us at all
This election cycle was tough.
We tried to grow in 2019 with more staff than we'd ever had.
We've always had a leadership problem of trying to transfer skills from the top down to help lift up employees that don't already 'have it' - especially (braggart time) me and my partners skills as I think our uniqueness as a firm is tied to my work in particular (which my parter is very good at picking up) especially tech & a certain unique vertical of advertising.
It's hard to find employees with multi-skillsets and experience to run things themselves using our tools. especially in politics not a lot of people come in from the outside, and there is low tech skill from the inside.
With larger staff we tried to do more training, tried to build stronger team mindset.
That I think that's our biggest weakness and leadership challenge. Still is.
An example from this cycle of it not going well:
A big problem is mistakes. Our work is hard, long hours, stressful clients making last minute decisions.
One staff member in particular made a large amount of mistakes - and big ones. More importantly didn't seem to learn from them. Lost us important clients and reputation.
So come end of cycle we usually have to downsize payroll.
Choosing who is tough. This year had to decide do we prioritize team cohesion and moral at the cost of mistakes (and our reputation is a big potential issue)? Or do we try to go with more skilled employees who are also more likely to leave, especially without the larger team bonding. Or i guess third option do we take a larger risk than usual in having larger cash loss during down period.
We went with higher skill. Well I think it just bit us, losing a key employee to another agency - the same agency the mistake employee landed at. It's not a coincidence. though to be fair in our business we usually lose people after 2/3 years anyways so maybe just stings more than a disaster of decisions.
Hiring is also a leadership challenge for everyone it seems. It's almost random given the few we hire which all look promising which ones end up excelling.
We need to improve learning skills to be more bottom up if we want to grow. But another leadership challenge: I'm also not sure it's our best path forward. we might be more profitable and successful staying smaller and being top heavy.
I've worked with those "mistake employees" and if they landed somewhere else that's probably the last place I would want to go.
Though to be fair everybody can make mistakes, and you would have to access if it was lack of skill, lack of attention, "impedance mismatch", or maybe it was the general climate that was making this employee less effective.
And I agree the climate or culture of our company is something we're working on and some people just don't work well in that environment. It's like a coin flip though on hires, the ones that you think are awesome sometimes don't do well and sometimes the ones that you think are green end up being amazing!
Plus it's just politics in general. It's really fast paced, high volume, crazy campaigns. the last months are like log higher work/money raised.
Either way congrats on starting your own agency! I was an early employee at an agency (not focused on politics but likely similar to yours in other ways) and when I started out there were fewer than 5 employees including two founders. It was very top-led in the beginning, but as we grew to 20 people or so that became unsustainable.
At that point it became about building a system instead of trying to get everyone up to the same skill level. At a basic level we decided that we were really working with clients to set expectations and then meeting (and hopefully sometimes exceeding) those expectations. We too had issues with last minute changes, until we changed our contract and statement of work language to specify the framework for making decisions (usually budget/spend/creative related etc) and how those decisions/changes would be implemented. Same thing with mistakes: part of the expectation from both sides was built in time for QA to catch mistakes before they happened. The more you can set up the framework for success early on in the sales/pitch/onboarding the better. And clients will probably like you more for setting up reasonable guardrails in the beginning.
The framework also allowed for some influence/involvement from the top, which was helpful in filling those inevitable skill gaps. We used some version of the framework until we got to about 45 employees, and then it had to change significantly again to fix some of the bottlenecks that were coming from the top down. It also opened up more time for people at the top to work on business development and sales.
I left out a lot of details but overall it took a “systems thinking” mindset to fix issues once we got to a level where the top-down approach was no longer feasible. The system was set up from top down, but once implemented it could basically run itself with a few tweaks throughout the years. Maybe you can focus on setting up those systems instead of trying to level up every employee to be a mirror of you and your partner.
Hiring/firing when there is a strong system in place also seemed easier: look for people who can grasp/appreciate the system and their place in it, give them agency and opportunity to grow within the system, and evaluate them based on the system and the expectations it sets. We almost never lost talent to other agencies and we rarely had to fire anyone. Maybe we were just lucky, or maybe the system did its job!
My two cents on growth/profitability for an agency: The existence of other agencies, however inferior they may be, means there is a limit to how much of a premium your agency can charge. At some point someone with control over the budget is going to balk at your price and go with the competitor who is also saying they can do everything you can do. Which means at some point you will need to grow your client (and employee) roster or be satisfied with stagnating profits.
YES. That's the exact same struggle we have! making that transition from partner lead, partners doing the work, to having a more distributed 'assembly line' delegation of work to more employees.
that's good advice on client expectations. It's a struggle politics is crazy - very hard to explain just how crazy until you've worked there which is a problem unto itself. democrats really lack technical skill (at the level HN knows) because even most startups don't seem as chaotic and they pay way better. candidates themselves at the Congressional level can be the worst in causing this crazyness.
another good frame that you mentioned is thinking more in an engineering mindset of systems design might help me thank you! micro-services haha.
UGH yes pricing is the worst. That lower margin, higher volume growth is what we're trying, but I'm not sure it might be better to stay small with higher profit margin. We made slightly less profit this cycle despite having over 2x the retainers. I'm money driven so always want more so it's a big decision for us. We're going to try again this cycle - it's not like I'm struggling here, I still am doing well!
Sounds like your experience is similar on pricing. there are so many people who want to do good, come in and start a digital agency and charge no joke $2k or $3k a month for a LOT of work. And candidates and campaigns are super super cheap but in a really dumb way. Especially Democrats. Republicans will pay a flat % of what you raise, in that case the free market really does work - though sometimes too much bad incentive lots of gross (fraudulent) tactics; read the recent Trump/RNC pieces on their fundraising pages.
An example differentiator that is hard to sell or explain is we use an ESP that I don't think any other political shop use because the political features / tooling doesn't exist. I built that on top to make it fit political needs - and some other cool things like real time data for wayyy quicker reporting. I see the value, clients usually don't but most still trust us.
That switch alone usually gives a 4+% open rate bump which usually equals more than the difference in cost.
We tend to fit best & win more work with clients where there is an existing human relationship of good work or from the parent committees where our work and reputation is good, rather than just cold pitching on price to someone we don't know - much harder to win an account cold.
One good sign that we're doing some things right I actually just saw a report comparing digital firms congressional ad revenue and was surprised to see much bigger companies didn't actually have much higher Congressional ad revenue than us. But those big guys have bigger non-profit clients.
So that's a key goal for us to get more advertising. which in itself is hard; TV firms fight to keep their 'primary general consultant' monopoly even if they have no digital experience. It's gross we sometimes have to do commission splits have to give a % to tv firms just to do the digital buying (they don't do anything we do the work.. they say it's because they made the TV spot, but after charging the campaign $40k in production you'd think the campaign owns it...) sucks. but tv guys are the top historically that's who steers the ship right or wrong.
Plus Democrats barely spends on digital. It's ridiculous like PG, Coke whoever gets it and follows eyeballs and $ quickly. Dems are SO far behind despite seeing campaigns that spend more on digital ads tend to win more!
And again thanks for your input and just sharing your story, it helps I think just to connect and know we're not alone.
(a) saw things in terms of them being persecuted, and took critique of their work or approach deeply personally
(b) tended to see things as us vs them, and not a two-way street, where both sides bore responsibility. And that sometimes crappy things happen with no malace.
(c) resented other's success at the company, and thought that the 'successful' person was only successful because management supported them unfairly in a way my colleague was not supported. My colleague perceived themselves as a secret failure for not doing what the other person was doing. They also thought others telling them they were successful was not genuine.
(d) lacked a kind of self awareness, and tended to take over meetings with their grievances and upsetness. They couldn't see that other team members needed to discuss their own issues, or with the issues they brought up, that other people also had valid emotions and points of view on them they needed to hear and appreciate.
The time we worked on it as a leadership team went beyond having difficult conversations. I've had difficult conversations, where you talk about someone leaving a job, or someone's difficult behavior. You give it in a loving, compassionate way. Some people can get defensive, maybe upset, but will hear the feedback and take some time to digest it. Even when they're upset, they take some part in the responsibility for the feedback they hear.
This person, assumed off the bat, you were going to attack them. They couldn't see the compassion you were trying to bring. They froze up and got defensive. They tended to carry their own narrative of how they were the victim, and didn't take responsibility for their side of whatever they were having a problem with.
I give credit to our leadership team that we kept at it. We didn't accept this person's sometimes abusive behavior. We tried, and frankly, by letting others know it was not OK, and that we kept our focus on it, it helped the rest of the team understand that "yes we get there's a problem here".
We wanted to help the person. We gave them lots of opportunities for improvement and to do the kind of work they said they wanted to do. We gave them coaching and their own time to develop their own interests into new business directions.
After trying and trying, probably helped a bit through some coaching, this person realized the company wasn't a good fit for them, and they left on their own accord. This was a good outcome. Though I wish there was some way to have accelerated it and/or let the person go so they weren't as destructive to the team.
1. Openness to experience (inventive/curious vs. consistent/cautious)
2. Conscientiousness (efficient/organized vs. extravagant/careless)
3. Extraversion (outgoing/energetic vs. solitary/reserved)
4. Agreeableness (friendly/compassionate vs. critical/rational)
5. Neuroticism (sensitive/nervous vs. resilient/confident)
Excessive neuroticism (aka emotional instability) can be very hard to deal with, at a personal level and at a professional level. But note that excessive confidence can be just as harmful to an organization as being emotionally unstable, and sometimes just as hard to deal with.
Then, psychological safety in an organization is also important. Honesty and disagreement should be seen as acceptable as long as they happen in a context of respect and in a constructive manner.
You have to ocassionally give developers some time and autonomy to do stuff they consider important. They want to do what they perceive is right, and while not every time you can let them do it, sometimes you have to listen to them, trust them and let them do it. It will not be a waste of time, believe me.
If you don't, you are at risk of them getting burned out. You do not want burned out developers, it's a waste of time for everyone.
I am not in the business of fixing gaping personality issues. And any work related coaching was impossible due to his victim mentality and inability to accept feedback.
Some people asked if your engineer was technically gifted. For me the answer is it doesn't matter. The toxic attitude always undermines any technical contributions they makes. Even a talented asshole just ends up taking on more and more critical projects, which widens their sphere of negative influence.
When I started as a lead I devoted a lot of time and energy to someone who was underperforming and difficult to work with (and whose self-perception didn't match reality) when I should have devoted myself more to engineers who were doing well and receptive to feedback.
In my country you really can't fire anyone without a major HR process that saps everyone's energy and morale.
In your case it sounds like everyone would have better off if this person had been fired early on in proceedings.
Once I made someone redundant, which can be a back door mechanism for firing in some circumstances. He just wasn't cutting it. I felt ghastly afterwards.
I ran into him months later and he told me he had no hard feelings, and the shock of it had made him reappraise his career path and he had made his way into a job which was much better suited to his skills. He was far happier.
Maybe other teams are better at dealing with him.
It was very subtle and masterful, you would see people trying to tell him of their problems, and an hour later leave believing they got their way, only to have agreed on the exact opposite, and being happy about it.
I was too young then to fully appreciate and learn from it. It was probably something like what people were saying about Steve Jobs’ “distortion field”.
He would sit and listen quietly, try to figure out what you were passionate about. He would himself get excited about _that_ too, and then slowly move the direction to seeing the world from his point of view.
After a while I got to know the guy pretty well, and I am sure he was not a sociopath and there was no malice in it. He was genuinely interested in people’s opinions and wanted to help them, he just had a grand vision and managed to find purpose for people in it. He was something like the embodiment of what the book “How to win friends and influence people” was about.
What I believe now is that there is a way to talk to almost anyone about their issues and help them overcome them. Every time I have trouble resolving issues like that I would try to go back and think “what would this person do”. Usually helps.
I can understand management being hesitant to fire someone technically competent, but this kind of disfunction can tank the productivity of an entire team of otherwise technically competent people, as OP alluded to at the end of their comment.
Since it looks like you were trying to avoid this, I figured I would let you know so you can excise it if you wish
Edit: my colleagues did not actually get really motivated until we deployed our first client on the new system which did make the whole thing very stressful for me because it was too much of an uphill battle. Once deployed, it was so much more performant and so much more stable that we all saw we would be spending far less time fixing bugs or trying to squeeze out performance: that changed everything.
I made similar suggestions to my boss about a system once. They basically told me it would never happen and to stop thinking about stuff like that so I could focus on the day to day stuff. Well, 2 years later and they outsourced that entire group to a company who will end up rewriting the system...
It was a different time: the product was a combi of perl, php, c++. And then the business world, at least here, went over to java backends.
If you continue to lead, at some point, its going to feel like all the walls are crashing down around you and your team.
Your path forward will most likely not be perfect, but it is a path, and the team will look to you. Be open to ideas and feedback, but I'm talking about when nobody on the team knows what to do because it feels everything has failed.
Pick a direction, start running, and scream "this way!"
It's your job to say "Get to the choppa!" if that is what the situation calls for. Nobody else is going to do it.
Within a 11 year span of working in same but large company, once you’ve mastered the resource management, the hardest leadership skill is kudos ... toward your upper management, ... knowing when to let yourself down and have your boss get the kudos instead.
- IMHO, the ADHD workers are the easiest to managed (trick is gaslighting their focus into a hard problem that highly interest them for them to tackle). My Kudos are often brushed off but still required to be dispensed tactfully.
- Laziest workers are definitely the hardest to narrate a path for task completions. Kudos are rarely a good tool for shaping of the lazier’s task path and too easily overused toward increasingly diminishing ROI.
- But upper leadership kudos requires letting go of your own greed, avarice, possessiveness, ... in many words to shorten, the real power in leading.
Harder still is making the your middle boss of many middle bosses look the bestest of the best. Even to a point of moving his name in front of your invention patents.
That was a strong sign that this rat treadmill isn’t for me and that I truly have the entrepreneurial skill to strike out into a smaller company and startups.
I excelled there as well but the happiness factor was way better.
I think advices can be without providing proper context can not only be counter-productive, it can also create toxic cultures. I've been part of a company where the CTO was a very self-help guru type "positive" person. There were compliments, positivity, motivation etc. everywhere. There was no bar for excellence. Everything was excellent to begin with. Everyone was congratulating themselves not only for doing the miniscule things, but also for bringing in a good team spirit. The whole culture ended up being a participation trophy culture.
All the good employees left the company, and the medicore ones were still doing the same thing last team I heard. This toxic positivity has become very popular in pop cultures. Unfortunately it's all appearances, underneath the positivity is the thriving mediocrity.
Always be looking to take your ego out of the situation. You are there to facilitate the success of the team it’s individual members.
The "core developers" become a bottleneck to all changes, even if they offer the best feedback available. The team eventually leans on them as a crutch to catch all problems, progress grinds to a halt as everyone is waiting for their code to be reviewed by X, the core developers don't get any real work done, and the rest of the team never levels up because they don't learn lessons that sometimes are only learned the hard way in production.
Good leaders know how to "let go", delegate, and recognize when they're becoming part of the problem.
I was in charge of elevating some code when I first started. I screwed it up and had to spend 6 hours redeploying while the team waited. It did not feel good telling everyone about the situation. It turned out ok in the end.
I was the ASC for a team (actually 6 teams across 2 departments). The application had a serious vulnerability that required multiple people to address. I brought up the issue with my boss - not prioritized. Talked to my department head next. They told me they weren't going to address the issue because they have a backup system. So I added if they ever tested the system or had documentation on how to restore from it - nope. So I did all I could do. All the tech leads were shocked when I talked to them about it. No way was I going to own the security for that POS system, so I posted to a different area of the company.
I worked as a tech lead (unofficially as I'm only a midlevel dev - seeing any issues with this company so far?). Oddly enough, I don't remember any serious issues even though this was the most authority I was given (took really, the others have me their trust/approval/etc to lead them). I had a great team and we were able to overcome a few challenges and provide business value while performing some major technical upgrades.
What is "elevating code"? (I'm trying to work out of autocorrect has screwed up the word "deploying".)
What is an ASC?
ASC is Application Security Champion. Essentially the role requires some internal security training then you are responsible for following the processes to identify and remediate vulnerabilities.
Best/Worst job ever.
After that everything is a walk in the park.
I will say after working in web development, software engineers are a unique breed and are difficult to integrate into a team. I believe this an issue because of the demand for developers and the amount of knowledge they control.
Luckily, I don't work in the web development world anymore.
Things were slowly improving as we collected metrics to improve poor code quality and shoddy releases that were killing us all. (This predates SRE/devops by a decade.) The AD teams had no choice but to add some quality control but still things weren't perfect.
At the end of our third year of this five year project the project manager who worked with me on one portion of what we did was promoted to executive director but I was not.
Within a few days of learning I was passed over for promotion I also accidentally discovered my grandfather had died of cancer. I didn't even know he was sick! No one in the family told me. I just found out about the funeral when someone asked me if I planned to attend.
While at the funeral I made plans to have dinner with my younger sister and to go to Las Vegas with my grandmother. Soon after my sister was dead, killed in the line of duty as a police officer. A month later my grandmother was dead from open heart surgery.
The whole time this was happening people were coming up to me at work asking how did that guy get promoted instead of you? How, indeed. The challenge for me was staying motivated and putting on a happy face for employees and not quitting. Frankly if I'd been able to I would have.
The part that makes me laugh now is at the time we still did exceeds, meets, needs improvement stack ranking. My boss told me if he had made me exceeds I would have gotten the promotion but he couldn't because of politics: the guy who sponsored the fellow who did get promoted managed to get my ranking knocked down so I wasn't competing with his fellow for ED. To top it off my mentor dropped me: he said if I was no longer an exceeds it was a waste of his time.
Despite falling into a black pit of depression I powered through the motions of being a people manager but frankly I couldn't take any part of managing careers of others any more when I knew the system was so broken and I had wasted years away from family and friends. My solution was to go back to being a hands on technical person: I transfered to our internal IT group and started over. I'm back to leading teams and getting kudos from the top of the house but still if I'm honest I feel like I failed my biggest challenge by choosing to just move on. On the other hand I'm certainly far happier and no longer ignoring family and friends to work 80-100 hour weeks. On balance that's probably for the best.
You're working at a toxic place and putting your own self worth up to them for measurement - this is not healthy.
People out of school until age 35 sometimes have a hard time truly separating their work from their professional identities, something we could all work on.
So sorry for your losses, I wish you well.
I used to lead a global team of 80+ devs at a senior management level. I inherited my team which was an absolute train wreck with a poor track record of poor performance who delivered nothing causing much angst to the business. Over 3 years, rebuilt the entire team, let go of these who brought toxicity/incompetence, set strategy, tightened comms and developed leaders with clear lines of responsibility and accountability. Shipped one product after another. Put the team on the map internally and externally. Accolades from every part of the organization. Made my leaders look like world-beaters. I was known to be an authority on my subject area and the rising star. My reports looked up to me, I inspired my team buy being an empathetic leader and I was hailed as a change-agent. Frankly, I outdid myself and it was one of those times, we sometimes have in our careers where we fire on all cylinders without a single misstep.
Come time for promotion, I had a rude awakening when my boss got promoted thanks to my back-breaking work but I got passed over and to add to the insult my newly promoted boss decided to fill the vacancy by bringing in a transplant from another part of the company to add an new layer. The new guy was well known to be the biggest ass-kisser in the organization so a total smooth operator to his credit despite being clueless in the domain. My challenge was to continue leading my team with a straight face despite taking this gut punch every day when faced to my new reality. It was a depressing time when I was also dealing with a personal loss in my family. I had naively assumed my work did the talking and my personality, relationships and overall competence/qualifications would continue my ascent. Its hard articulating this but the amount of time my own achievements were reinforced by outcomes and my prior leadership made me feel I could do no wrong until this point.
My big mistake was that my ego fed a sense of entitlement that made the change harder to deal with. My reports were now well entrenched and confident as I had always wanted them to be with large teams. I sensed a feeling of disappointment from my own teams over my lack of elevation and the impact it would have on their careers. Over a period of time, I went from being the shining star to someone about whom everyone wondered as to what’s wrong. I felt vulnerable in taking decisions that I once took confidently and my confidence took a beating. I mentally beat myself up as well for not playing my political cards well as well as sometimes questioning my own abilities. Added to the daily ignominy of reporting to someone obviously not qualified, was every decision/outreaches/opportunities/credit that were usually mine in the past due to my domain expertise now being passed over to my new boss who would emphasize the same with a lack of class and competence. I also got a sense that the new guy resented my abilities and would now start having direct lines of communication with my reports sometimes even not giving me visibility. He just wanted to get rid of me since my presence probably constantly reminded him of his lack of involvement in this teams prior success. People who would consult me for critical decisions would tend to leave me out as I was not deemed that important considering I was no longer the main decision maker. There were so many incidents that I unfortunately still recall that happened over a 1 year period that I stayed on after this development.
For me though, that was a lesson in humility and my own vulnerabilities. My swagger is gone and I don’t things for granted as I once did. Thanks to my own qualifications and experience, I had several external opportunities the beckoned that I could execute on and did do so. However, that feeling of being totally ripped off, a sense of anguish at losing something I built, sadness at dealing with a team that you built and loved that turned on you still remains and part of me is still bitter. I still love leading teams and getting the best out of people but the politics is toxic and can seriously damage your physical and mental well-being. I know why some of the best leaders I know remain relegated to lower levels of their organizations and I respect them even more knowing the balancing act they deal with. I don’t get too attached to teams, products, jobs anymore and am prepare to lose it overnight and rebuild. I continue leading large teams but I could still get a job as an individual contributor and be happy with it if it ever came to that.
Now I realize I don't want that job for any amount of money.
- dev with low self-esteem causing social issues: problem ongoing, helping though: speaking about it, more focused tasks he can take ownership over and finish without that much communication and trouble.
- dev generally not nice to people (and not that compenent): people started avoiding him and he quit... Should not have come through the probation period, but I wasn't in change of that (see next point).
(it's also not that easy firing someone in germany btw)
- ownership of product and progress, but no say in direction (which changed every 2nd week) and not officially team lead: I quit.
i cofounded a venture-backed startup with my brother. a few years in, i had to fire him.
too many details to unpack here, but, gratefully he's found footing and is happy building something else. i'm still running the venture although we are running out of time / money.
(i'm not sharing that last point for sympathy; i understood the risks and i'm prepared to face the end, just like the beginning.)
overcoming it? honestly, i just pressed on; what else can you really do? i got therapy, counseling, to work through the difficult patches and i invested in myself a bit more so i could find peace with it all. i realized that i had a pretty serious co-dependency issue and now i'm clear-headed in a way i've never been.
so, the result has been net-positive.
Quit the job
Found a job that allowed me to have the resources and flexibility to truly lead (not simply have the title)
I called each of the team individually, and broke the news. I will never will get out of my head the inconsolable moans of his junior engineer he had been mentoring.
There was a fair amount of pressure from “leadership” not to divulge any details, but fuck that. They needed to know he was an recovering alcoholic and on-and-off-again manic depressive, and that there was nothing they could have said or done that would have made a difference in the final outcome.
Transparency that builds trust has never failed me, whether why a coworker committed suicide or why our backlog priorities changed overnight, or why we chose to use GraphQL over REST.
Listen deeply to your people, so you can understand them deeply, so you can empower them fully,
I failed with my friend because I wanted to believe the lies that addicts tell so well. If you are listening closely enough to your people’s words and actions, and you put aside wishful thinking and blind optimism, as well as lazy skepticism, then you’ll know what they need. Then your job is simple: get them what they need. But I missed his warning signs because I was more focused on the success of the startup than on the success of his life. Never again.
Management is an important role in many organizations. But in a small startup people need to manage themselves. What they need are leaders who listen carefully, communicate clearly, and create a culture of transparency and trust by exemplifying both.
People talk about transparency in the same way people talk about a just-war: that the rules only apply up until the point your principles may cost you victory. But what’s the point of transparency — of pro-active honesty — if “well, in this situation discretion is more advisable” is actually the principle most valued?
Human beings matter the most. If the choice is between your company failing and the well-being of your people, a decent person and a good leader chooses their people every time.
This doesn’t mean you can’t fire people. If they aren’t performing, then they are in the wrong place, and deserve to be somewhere else where they can develop. Firing a person means we made a mistake in hiring, and it’s incumbent upon us to see what we can do to rectify that mistake,
I could go on, but you probably get my point. A company is nothing without people. So take care of them, even and especially when it hurts.
Managing a team shouldn’t be a political drama.
As a new team lead, coming up with a roadmap, and not being able to subdivide a project into independant parts that can be worked on in parallel by different team members.
Actually this year has never been easier for appraisals, all successes have been despite the great covid challenges, all failures and delays are due to the terrible covid disruptions.
I joined the company as a dev and quickly got promotes to a PO/Teamlead position. To be honest, it was everything I could have wished for, and I felt very lucky - fantastic colleagues, exciting product, cool tech, modern ways if working, and the team I would lead had some fantastic individuals and a positive attitude.
I was assigned to a newly formed team in charge of a new revenue opportunity. The project was the CEO’s little baby, so I was a bit nervous of how his involvement would be, but so far there were no red flags. I had heard some comments from colleagues about him - he seemed to come up in conversations a lot - but nothing major, I thought.
This was my first management role and I felt completely overwhelmed. I got a large amount of responsibility on top of still doing my previous dev work. Managing felt a lot like what I imagine being a preschool teacher is like. Coming in with grand ideas of wanting to help the team be the best it can, having high ambitions... and then drowning in the sheer practicalities. Misunderstandings, people with different wills, tantrums, power struggles... I wanted to be an empathic and supportive team lead, but my manager colleagues who were much more direct and strict seemed to be moving along and through conflicts faster (not true, I learned later). I was proud of always putting the welfare of my team first. Later a member would tell me he decided to decline a move to another team for that reason, so at least I did something right.
But instead of focusing on learning to become a good manager, problems with the CEO started right off the bat. I went on a short vacation, during which he had summoned my team, upset and wondered what the hell is going on, ordered them to do the exact opposite of what I had tasked them to, then grabbed me on my first day back to berate me and tell me I should listen to him because he knows better than me.
His behaviour came in waves. If things appeared to be going well, he was your best friend and generally hands-off. The moment he smelled what he perceived to be trouble, problems began. Eventually I ended up permanently on his bad side due to a long series of drama.
This is the point I learned the company had hired a leadership coach who spent 99% of his time helping managers deal with the CEO and his antics. Up until this point I had thought I was getting on his bad side due to my behaviour or results. Now I was slowly starting to realize that everyone who reported to him had a similar experience.
I started to have a feeling of constant dread. He was unpredictable and could react suddenly to anything in any manner, often with ferocity. There were groups of people spending significant time trying to control his outbursts. He would usually be apologetic after, and claim to have learned a lesson, but the next day it would be back to the same old.
Things started to take a toll on my personal life. I was drained, agitated and exhausted from work, and brought those emotions home. I had to see a therapist. We also had our first child around this time. Then I started getting weekend calls. The worst was a sunday morning call from him starting with ”I just had a great idea”. The great idea was to throw my last two weeks of planning in the trash, smash my team together with another team, have both team leads lead the team together (which naturally lead to an instant power struggle) and add some unrealistic expectations to the mix. Funnily, I was still telling myself that perhaps this was normal.
Then we had a salary discussion. When I joined I had been promised a percentage raise after the first year, otherwise I would have taken another offer at the time. He told me that despite getting good feedback, I am actually performing bad (I asked him to back it up with statistics which I knew existed - he answered that I should just trust him because he knows better) and could not give me the raise. I didn’t really care about the money, but at this point I felt that, if I can’t even trust him on his word, it’s impossible for me to work for him. He lied as usual when challenged and claimed he had never promised the raise, except this time I had written proof on the promise and asked him to honor it.
He reacted about as well as could be expected. Anger and tantrums. Incoumd tell he wanted to fire me on the spot. Since that’s not possible here, he demoted me and sent a multi-paragraph rant email to multiple parties explaining how we had both agreed that if i’m not the best employee in the company in two months that I would cease to be employeed. After I replied that we had not agreed to that, I was offerer a moderately-generous exit package. I took it without hesitation.
An hour after taking the offer, a colleage stopped me in the corridor and asked ”What happened, did you get some good news? You seem a lot calmer than usual.” I realized it was true - all my anxiety was gone. I felt relief.
Don’t let yourself get treated badly chasing a career. I’m back in a dev position elsewhere and couldn’t be happier.
This led to quite a few rushed learning experiences for myself, since I hadn't had the same years of mentorship that you'd usually expect.
* Learning how to balance mentoring team members and how to be hands off. It's easy to get into the position where you're spoon feeding the team or haven't built their confidence up. You become the bottle neck and overworked. On the flip side, if you are too hands off, then the important implementation details slip through and you miss out on things you should know, but are not getting bubbled up. It's a hard balance that I still struggle with, and I don't know if any resources truly cover it.
* How to manage under performing employees is a struggle. For example I've had a very senior team member who was struggling with personal issues and it was causing their output at work to be riddled with issues. However we had nobody to cover his areas of expertise and he refused to take time off. Trying to balance this while managing the rest of the team was a real nightmare, which involved pushing them on to lower risk tasks and absorbing more of the load myself till they could work through their issues.
* Setting culture is a difficult one too. Team culture is often top down and leaders need to be aware that everything they do trickles down. However often the negative aspects amplify greatly over positive ones. While I would never compare myself to someone like Linus Torvalds, you can see this in how people try and emulate his negative characteristics (heated project comments) without understanding context or seeing his positive moments. Similarly I was known to be very critical in code reviews, though I went to lengths to soften my feedback and was never harsh. However over time I noticed several junior devs were emulating the criticality of my reviews without picking up on the softening and positive aspects of my reviews. This led to several scenarios where they'd bully other devs in code review and attribute it to my review culture. Anyway again this is something I find difficult to deal with. People naturally amplify negativity and the only way I've found so far is to be vigilant and counter their adopted behaviour early. Whether that's intervening in code reviews, or providing regular work culture refreshers, it is something that's required to maintain a healthy culture.
* On to specific examples of issues I had to struggle with. A lot of the devs on my team were not great at body hygiene. Some didn't bathe regularly. I was literally being asked not to send people to meetings . The only solution was to ask HR to send a strongly worded notice to the whole company to remind them about hygiene and taking some folks aside to gently suggest some mitigations for their hygiene. It was rank.
Have to pick your spots.
Exerting soft/passive power has been the major long-term challenge, I think. Learning how to exert action at a distance requires a lot of finesse, a lot of listening, and more scanning than printing, so to speak. I'll be the first to admit that I lacked some of that when I began; still do now, really. You have to think about things as an analyst, an evangelist and an investor, rather than a do-er. There's a lot of education, persuasion, and sermonizing involved, even if it's primarily in recruiting others to work your ideas or to join your team to work on theirs. Leadership is about people; people can be messy and fickle, so leadership challenges involve things that can be messy and fickle.
Finally, patience has been the most subtly challenging part of all of the above. When you're more alone and need to exert soft power to be effective, you need patience in spades, and you very likely may lack it. I certainly do. The impatience that was such a virtue to me as an IC has bitten me as a leader. I've had to learn the hard way that patience regarding challenges isn't a nice to have -- it's a necessity, and without it, I'll fail.
That said, I think I have enjoyed a lot of tailwinds that have made much of my early leadership challenges a non-issue. I'm pretty self-aware and am more motivated by winning than being right, so I've not had too many challenges with stupid unforced errors on my end. I like talking to people and enjoy fixing their problems to make them happy, so management and leadership has large component of real fulfillment to it that I don't have to fake just because it takes my career forward. I've spent a lot of time in necessarily cross-functional technical roles at startups in my early career, so it's never been hard for me to empathize with leaders in other divisions and be an asset in effectively translating technology into their business goals.
But even with all of those tailwinds, leadership is /hard/. Beyond the day to day challenge of increased responsibility, decreased agency, and thinner safety nets, it's just plain mentally tricky in so many ways I could conceive of but not fully appreciate until I began my own journey. The highs are high, but the lows are really, really low, painful and traumatic even. I never questioned whether I should be doing what I was doing as an IC. But as a leader, that questioning became a lot more prominent. And it had very little to do with how well I was objectively doing according to the CEO (which was "very well"). I think it is just the nature of the beast.
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