Ask HN: I'm changing my job after a 15-year tenure. How should I proceed?

What seems to work for me and many people is: soon after you join, start meeting with many people one on one. First with your immediate team, then with people in closely related teams, stakeholders, people doing a similar role, people who are a bit more senior, etc ... It can be a bit awkward initially to schedule these meetings, but almost everyone would be happy to have a chat, tell you about themselves, the company, the projects they're working on. They will often also tell you about other people you should be talking to. Listen well - people will tell you what's important, what they would be interested in collaborating on, what are some gotchas you should watch out for. After a while you'll kinda naturally get a feel for who are "your people", so just continue talking to them and find excuses to do cool stuff together. Most people are biased towards not doing enough of this sort of thing, so unless you know yourself to be some kind of hyper-social connector, assume that you're not doing enough of that and correct by forcing yourself to do more. A good rule of thumb is to meet someone new every day for a few weeks.

What would be the advice that you'd already write to yourself? You might spur a couple of HN'ers to riff on what you will say yourself ;-)

I've only done 6 to 12 months stints, so no advice from me I'm afraid.

IMO, don't "try" to make friends. You'll come off as fake and people will notice.

Instead, be yourself, and if you have to try for something, try not to upset other people.

Ask for asking Mike for help, just do it. He knows you're new and the company has told him to help you get going. You'll stop being the clueless new person after you've learned about the company's stuff.

Let me use an anology. What you think will happen is just hopping from one train to another. What might happen is they'll kick you out of the train on entering one, there is no other train stopping, and you might have to abandon the trains altogether. We are cool folks over here but in professional environment if there is a clueless new person and they can be used somehow, then it unfortunately happens.

I try to get involved and be seen and make connections. If you’re working in the office, that means grabbing lunch with your coworkers, maybe getting drinks after work - socialising basically. Things become much easier when you get over that new person phase, and you are comfortable approaching others and vice versa.

For fully remote it’s a much bigger challenge. I try to get involved in social slack channels and connect with people that way. Also finding ways to talk face to face on Zoom etc goes a long way.

Been there, done that. 10+ different jobs in a span of 15 years (contracting).

Let's start with the basics. Be a nice person, approachable and someone easy to work with. This will remove the barriers and your co-workers will be more willing to contact you first! Honestly, these qualities will get you far.

Get "into" the company's culture. There might be internal pain points (ask questions, people will be more than willing to share their pains. If you listen you will easily make connections). Same goes for the inside jokes.

Finally, from experience I know the first to three months are the most difficult ones. And that's fine! Accept it and don't be harsh on yourself. You sometimes will be doubting yourself, feeling low, but all of that will pass. It always does!

>How do you go from the "new clueless person at work" to "oh hey Mike, I'll need your help this afternoon"?

There's a people aspect to it, a time aspect, and a technical skills aspect.

For people, you need to develop rapport. A lot of struggle at the beginning is getting to know the right people. This is easier in the office where introductions are more fluid and you run into people.

On the time front, you become an expert on the systems a company employes as your tenure increases. You help design systems and understand the tradeoffs in the decisions that are made rather than walking in and saying "This is odd and I've never seen it before. Why is it done this way?", with answer quality varying on how long ago the decision was made. I've worked at multiple companies where people retire to start collecting their pension and come back a few weeks or months later working as full time consultants because they have deep knowledge of why things are setup like they are, the hiccups that will be encountered during a system change, etc.

You seem confident in the technical aspect, but certainly if you put out work product that doesn't perform well or isn't documented well, people aren't going to proactively be coming to you with questions.

Honestly, just ask anyone who they think you should talk to.

"Oh hey Alice, I got this problem with X. Do you know who can help with X?"

"I think Mike knows about X"

...

"Oh hey Mike, someone told me that you have worked with X. Is that correct? I could use some help."

Do this for every problem and you'll get a good sense of who your colleagues are and what they work with

So you may not have a lot of experience with switching jobs yourself -- I don't myself -- but you've probably got a lot of experience being on the other side of things, being on established teams in an established company and having new people join.

How'd that go? What were the failure modes? Who really nailed it?

One specific piece of advice is going to be to remember that your old company was your old company. Some things about the way it worked -- from its coding practices to its tooling and framework choices to its meeting structure -- were right, some were wrong, and most were just arbitrary and didn't matter in the long run. Don't be too keen to try to remake your new company in the image of the old one because that's what's familiar to you. Take some time to understand the new company and what does or doesn't work about it, and also where the existing sentiments lie.

When you do draw on your experience to offer a suggestion that you try X like they did at your old company because the Y the new company does just isn't working, you want the reaction to be that half the team has been saying it for years, but they haven't had anyone with the depth of experience with X to make the change.

I've heard this suggestion that you should schedule a few 1 on 1s with a variety of people and ask them to walk you through what they do, what they work with and how everything looks from their perspective

Hey, I really recommend the book 'The first 90 day's. Its immensely helpful for just this.

I was in a similar position to you a couple of weeks ago - switched job after the better part of a decade. The main things I've found that have built trust are: 1. hanging out casually with teammates in the office 2. taking notes and/or screenshots in every conversation and then reviewing them to stay on top of everything

From the other side, I've onboarded a lot of engineers in the past and the best ones have been "yes, and?" people. So you'd explain a process to them, they'd say yes and try to figure out what comes next. e.g. if someone explains that changes are released via a pipeline, the best on-boarders I've seen would say "yes, and what stages are in the pipeline and how do they progress?". Where possible I'd recommend the pro-active questioning approach.

I just did this, but not to the same extreme. My suggestion: Do the thing that worked the first time, and that thing is:

Be You.

I've been at my current job for three months. It's a small startup. I went from "where is the loo" to onboarding new employees in that time. Why? Because I'm an expert in my field. The landscape changes, but your expertise are going to carry you through. I'm having to re-learn a number of things I haven't had to think about in almost 20 years, but it's all there. Give yourself time to ramp up. And, one more thing:

Ask questions. Ask until you understand. DON'T BE AFRAID TO SOUND DUMB.

I tell new coworkers and managers this: I'm going to ask questions that may sound dumb- not because I'm dumb, but because I need to be able to relate information at its banging-rocks-together level. If they don't appreciate that, then I'm in the wrong place.

I’m curious how your experience was finding and landing the new job?

I’m in a similar position, at a big company for over 10 years after working in startups. I was technical when I got there but over time as I got more immersed in the business my tech skills have eroded. I’m now in a unique position as an executive that doesn’t translate super well to a lot of the opportunities at companies I might be interested in. I’m feeling a little stuck and I’m not even getting to interviews on anything I’ve posted for so far.

Curious if others have had this experience and how did you navigate it?

When I've seen "old hands" change jobs, the thing I often see them struggle with is the psychology of no longer being the domain expert. People underestimate how much deep knowledge they possess that is specific to their company. The longer the tenure, the more this is true. And most/all of it will be useless at a new place.

This is not a bad thing. And it is a good thing to branch out and see a broader perspective. But it's hard to prepare one's self going from being the person that knows everything about everything to being the person that knows nothing about anything.

Main thing is don’t expect too much. You will not experience that same feeling of comfortable camaraderie again for a long time.

Make an effort to listen to people. Keep your ego in check - avoid saying “Well at my old company we did …” - just listen to what people are doing here and now.

I would also say try to maximise informal 1-on-1 time with other people, ask them about their work, their opinions, etc. If you are in a larger group don’t opine, just listen. If you have questions, don’t interrupt the group - use it as an opportunity to go ask the relevant person after and build a 1-1 relationship.

Try to keep a smile on your face. Avoid dark humour or joke-complaining.

Edit: Say yes to everything, at least once, for the first year. Any time anyone invites you to a drink or a talk or a meeting, just say yes.

There is a lot of good advice here, so I will just add: be a pleasant person to work with! It will take you far (and is generally the right thing to do anyways :) )

Love this question. I recently changed jobs to a fully remote role and I was lucky enough to receive a detailed list of suggestions of people to meet, resources to access, etc from my hiring manager.

If you are starting a remote gig, doing camera-on video 1 on 1s with all the people you I would encounter (and often one level above) was extremely helpful for me as it gave me a chance to introduce myself and set the context for those who were not involved in the interview process.

I would always finish by asking for advice on what it takes to be successful at X company, people loved that question and shared tips that shed light on internal culture rather than the typical platitudes. Good luck!

Humility. You have a great skillset, I'm sure. But approach every thing at first like a junior dev on his first job, with respect and an open mind, trying to learn the current state of affairs. The pain points and places where you can add value will present themselves to you if you take a beginner's mindset, and you'll see where to strike. And that'll really be appreciated.

First, congratulations! It can be hard to step out of a comfort zone.

Second, realize that you will be the clueless newbie for a few months. Not in terms of tech or experience, but in terms of all those amorphous "I know how to get things done" tasks. You are going to have to sit with that and, while it won't be comfortable, it'll get better over time.

I've done this a couple of times in my career, though my longest tenure was ~8 years. My advice for "newbie oldsters" (just made that up right now) is fourfold:

* realize the value of new eyes to the company. You can see things that others don't because they are inured to their current situation. You only get to be a new employee once at each company. Enjoy that advantage, uncomfortable as it may be.

* take notes on those things that are interesting to you. Publicly document them (if they aren't) or improve the docs (if they are). Writing down something will give you experience in the domain and give you a chance to talk to folks when you ask them to review it.

* resist the temptation to prescribe in these notes or in conversations, especially early on. The team is excited to have you but if you come in and say "at OLDCO we did it this way, which is far superior" you will be wasting that excitement. The exception to this is if you see an existential threat to the company due to its practices (no backups, critical SPOFs). An open mind and asking "why" with an eye toward learning will serve you better.

* attend any social events that the new company has; as many as you can. Those non-work work events can be a pain in the butt in terms of taking time away from your personal life, but you can meet people outside of your team or even inside your team. And those informal ties can prove extremely helpful when you have a work problem in the future. ("Oh, we need to get design to sign off on that? I'll ask Joe who should be looking at it; we chatted at the Friday morning coffee a few weeks ago.")

Finally, some of this will come with time, but it usually takes 6 months to a year to have the internal credibility and confidence and knowledge to really make things happen. Take the small wins while you can and keep going.

I have just resigned after 16 years at my current place, so I can understand your feelings.

However, 3 years ago I made a mobility move within the company to a different division. To non-experts the new role looked similar form the outside, but almost everything was different: the people, (most of) the systems, even the culture, how the work was organized and appreciated, and so on. I experienced some sort of a culture shock. One of the problems I had to address in the new role was attrition and I kept telling people to give some time to their jobs to get a better understanding of what it was about and what opportunities it offered, and fought the same battle inside with myself to walk the walk not just talk the talk.

What I kept reminding myself about was that I should not compare the new role to the old one over and over again (except when there was some specific need). Instead, I just believed that my experience would help me help others. I was still the most senior guy in the team and after understanding where the biggest needs were, I started thinking about how I can address them, and came up with ideas which I went on to implement. They were much appreciated.

Another thing that worked well for me was to put all the warnings and indirect information I had received before my move on the back seat and give everyone a chance to start with a clean slate. I was very disciplined about that and as a result I could fix some historically very tense relationships between locations. I think if you approach people in an open-minded fashion, most of them will be happy to cooperate (except those whose interest dictates the opposite).

Also, don't be afraid to ask questions even about dumb things. I found that a lot of people with some experience are happy to share their knowledge and explain things to you. Listening to them will create mutual respect. And you will also understand who knows what and who you can count on.

Just be patient with yourself and you will find that you have the skills to be good at the new place.

EDIT: fixed some grammar problems

I did this after 9 years. My M.O. in a new job is to find a pain point and fix it quickly. Specifically, find a pain point that either directly impacts productivity, customers, sales, ect. If you're "allowed" to fix the pain point, it's a good sign. If you have resistance, run quickly. It means that management doesn't know how to handle your expertise.

Why?

You're a lead, you should be able to see problems a mile away. Your new company should trust your expertise to anticipate and fix problems.

Examples:

I joined a company with a Mac product that would peg the CPU for days. It was impacting sales. Took me and another developer ~6 weeks to refactor some bad design decisions in a critical area. Pegging the CPU for days dropped to 1-2 minutes. (If I wasn't allowed to fix it I was going to leave.)

I joined another company that was using a beyond end-of-life web programming language. The lead developer resisted my efforts to transition to modern Javascript, and resisted my efforts to transition to modern hosted source control. It ended poorly, although there was a lot of relief when the leadership announced that they were switching to Github. (I should have asked them to lay me off so I could collect unemployment.)

I joined a company where a small team had a project spread over 3 git repos, with tons of little dlls. Simple refactors that Visual Studio could automate would take all day. I merged everything into a single repo, and merged many small dlls into larger dlls. Build time was much shorter, and refactoring was possible. (If I wasn't able to fix the problem, I was going to leave.)

I've just done the same (thought not 15 years in), and here are some of the things I've been thinking through that may be help you.

This is an opportunity to change the things you didn't like about yourself in your previous role, and reinforce the things you did. I never took vacations. I had a reputation for always being available on Slack, no matter the day, or the first person on an incident call. Those things are still important to me, but work/life balance is, too, and with no reputation, I can be whoever I want to be. I want to be quick to respond, but only when a system tells me I need to, not because I'm trolling Slack on the couch at 8pm.

Ask a lot of questions. You know enough to be hired, but nothing about the new place, so ask! Give your new peers opportunities to be experts, and eventually they will do the same to you.

Try not to live in the past. This is a place I could use work myself. Rely on the things you've learned, but realize the situation is different, and if you compare now to then, you'll be disappointed. Remember, it took 15 years to get to "then." There is a possibility that it was more than just time, but it will take time to figure that out.

Assuming best intentions, you got to the place you are by being yourself. So, do it again. Rely on your instincts. Look at the world as a recent grad starting their new job, and do it again. You think you forgot how to do it, but maybe you never really knew "how" before, you just did it. If you did it once, you can probably do it again.

If you are used to being the guy everybody goes to it is a big change since nobody will depend on you if you are new. But that is fine, it takes som time to get recognised in a new work environment. If you are skilled it will change in 2-3 months.