I’ve been hiring engineers and testers lately. Even though pandemic restrictions are starting to lift, most of us are still working from home. So are the people I’m interviewing. That means I’m interviewing over Zoom.
I care a lot more about a candidate’s qualifications than I do about how they present on Zoom. I hope it’s true of all hiring managers. However, good presentation removes any subtle biases and barriers to your success.
Here are a few tips from the trenches that can help you present well.
Video and audio quality need only be adequate. You don’t need pro equipment. The camera and microphone in your laptop are sufficient. A webcam from a major manufacturer will be fine. A headset might reduce ambient noise; try one and see.
Test the videoconferencing platform before the meeting. A few times, candidates have struggled to get Zoom to work, and we lost the first five or ten minutes of the interview. If you know what videoconferencing platform the interview will use, install it on your computer well in advance and make sure your camera and microphone both work with it. Also make sure you know where the mute button is and how to recognize when you’re muted. Know where the app’s audio settings are, in case they say need you to turn up the volume on your end. If you don’t know what videoconferencing platform will be used, record ten seconds of yourself reading something into your computer’s video app. Play it back to see how it looks and sounds, and adjust settings in your computer accordingly.
If you can, do it in a quiet place. I got to listen to loud sirens in one interview, as fire trucks rumbled by on their way to a call. I am embarrassed to admit that one interviewee got to listen to our microwave oven roar and beep while my son heated up a burrito, as my home office is just off the kitchen. Neither was the end of the world, but it would have been nicer not to have those interruptions.
If you must use your phone, set it steady and level, in portrait orientation. One candidate used her phone, and turned it sideways so I appeared larger on her screen. But Zoom didn’t correct the orientation of her camera, and she appeared sideways on my screen. Another candidate held his phone in his hand the whole time, and it was a jerky experience. Get a stand for your phone.
Face the camera. I know a lot of people place their laptop to the side and their main monitor in front of them. But then they appear in profile on camera, as if they’re speaking to someone outside the frame. If this is you, use the laptop screen for the interview. Or do what I did, buy a USB webcam and set it on top of your monitor.
Position your camera so the top of your head is near the top of the screen, and you are centered horizontally. I spoke to one candidate who I could see only from his nose up, his head at the very bottom left of the Zoom window. I got a great view of his ceiling above. Another candidate appeared to tower over me on screen, as his monitor was somehow above his camera. When you are front and center, it’s far easier for the interviewer to connect with you. You may need to elevate your laptop to achieve this; a stack of books may do the trick.
Consider how much or little of your body you want to show. My camera’s position and field of view reveals my torso from the sternum up. I’m good with that, but perhaps you prefer to show less of yourself. You can move closer to the camera, or buy a camera with a narrower field of view. Alternatively, for some cameras (like my webcam) Zoom lets you turn off HD, which will make you appear closer on the screen and show less of your body.
Make sure the room behind you is tidy. In one screening call, I got a great view of the candidate’s unmade bed and some dirty clothes piled up on the dresser behind it. Tidy up behind you! If that’s not possible for some reason, consider using a Zoom background (but know that some people find them to be distracting). To use a background, you need to download Zoom in advance.
Pay attention to clothes and grooming. One fellow appeared on my screen looking like he just crawled out of bed. You don’t need to dress formally for a Zoom interview, but do make sure your hair is in order, your face is clean, and your shirt is fresh.
It’s the American mythos: if you work hard enough, you can accomplish anything. But I no longer think it’s true.
Mind you, I’m all for hard work. But I think success also requires good resources and good luck. Actually, I think resources and luck are more important than hard work. They make hard work gain solid traction. Without them, a lifetime of hard work usually yields very little.
I see it all the time in the inner-city church I attend: teens struggling to make a viable life as they enter adulthood, adults working hard only to barely tread water. Many of these people are bright and capable and have dreams they’d like to achieve. Few of them make a stable life, despite their best efforts.
In contrast, I’ve done well in my life. I make upper-middle-class money — not so much that I’m free from financial worry, but enough that the wolves are so far from the door that I’ve pretty much forgotten what they look like.
What has brought my good fortune? Hard work has certainly been important. But I’ve also had resources that my inner-city church friends simply lack, and those resources and my willingness to work have let me capitalize on the luck that has come my way.
My story illustrates my point very well. So I’m going to tell it three times: first through the lens of hard work, then through the lens of resources and luck, and finally through the lens of some of the difficulties I’ve faced, some of which were severe. As you read it, think of your story. How hard have you worked? What setbacks have you experienced? How have your resources and luck enabled — or lack thereof limited — success?
My story through the lens of hard work
Here’s the version of my life story, from the perspective of the success I’ve found in my life. Told this way, it looks like hard work really pays off.
I applied myself in school and got good grades. I also learned how to program computers. These things got me into a top engineering school where I worked harder than ever before or since. I got a degree in mathematics and computer science. I moved into a career in software development, where I’ve worked hard for more than a quarter century now and have risen through the ranks. Today, I’m a director in a software company. I have an upper-middle-class job and I’m doing well.
My story through the lens of resources and luck
I have worked hard. But when you look at my life through a wider lens, you can see how many resources I had available to me, and how good luck at key moments led to important opportunities.
I was born in 1967 to working-class parents who had high-school educations. We didn’t have much for a long time, but my parents were frugal and we never went without. Manufacturing jobs were reasonably plentiful then and Dad worked steadily. He was smart and capable, and in the 1980s was promoted to management.
My parents deliberately created a quiet, stable environment for my younger brother and me. We were well cared for and loved. Education was everything to them. Homework came first. They praised and rewarded our scholastic achievements. They always spoke of college as something we would do as if it were the natural next step after high school.
I was intelligent. I taught myself to read by age 3. And then I turned out to be well-suited for school — I was naturally well behaved and liked the rules and structure. I did the work and got excellent grades. In high school, I was accepted into all the advanced-placement classes, and I liked the challenge.
As I entered high school, the then-new home computers were just becoming affordable. I’d shown aptitude so Dad, flush with a new management-level salary, bought me one. I taught myself to write code on it. I spent hours mastering programming and really loved it.
I started writing programs to illustrate the concepts I was learning in my advanced-placement geometry class, and the teacher learned of it and had me demonstrate them to the class. He was impressed. “Jim, you could do this for a living.” That was a revelation: I had no idea people made careers out of programming computers. “You’ve got talent,” he continued. “You should study at Rose-Hulman. You have what it takes to make it there.”
I’d never heard of Rose-Hulman. It turns out it’s one of the nation’s top engineering schools, and it’s here in Indiana. I thought surely I couldn’t get in, but I applied anyway. To my astonishment, I was accepted.
Rose is expensive, and was out of my family’s reach. But the Lilly Foundation, the philanthropic arm of Indiana pharmaceutical giant Eli Lilly and Company, was at that time helping bright first-generation college students go to private colleges. Their grant paid for a large portion of my college expenses. I also got a federal grant and a couple smaller scholarships. One federal program let me borrow some money, and another paid me to work part-time on campus. A state program helped me find summer work to earn more money. My parents were left with about 1/3 of the bill, bringing Rose just into reach. They lived on next to nothing while they paid for it.
Rose was enormously challenging — I never worked harder before or since. But I made it through, with a degree in mathematics and a concentration in computer science.
At graduation, the country was in a recession. Like many of my classmates, I had trouble landing a job. I wanted to be a programmer, but those jobs were scarce. But I had taken a technical-writing course as an English elective, and the professor connected me with a local software company that wanted to hire a technical writer. The company was founded by a Rose grad who liked to hire other Rose grads. I got the job.
I wrote and edited technical materials for a dozen years at several companies. At one company, my boss saw something in me and promoted me to manager. And then it turns out I had an aptitude for leading people, and liked it. After completing a successful and important project, he gave me a new opportunity to lead software testing, and mentored me as I learned the ropes.
A burgeoning software industry has formed in central Indiana, and I’ve ridden the wave, moving every few years from company to company to take on greater responsibilities and new challenges. Along the way, several people have mentored me or taught me a skill I lacked. It’s enabled me to deliver well everywhere I’ve worked.
It’s been enough to impress corporate CEOs and Vice Presidents all over town enough that I can call them up and meet them for coffee. Several years ago I reached out to them all in search of a new challenge. With their help, within eight weeks I was in a new role at a company with a bright future.
My story through the lens of life challenges
You might now think that I’ve lived a charmed life. But I have had some deep difficulties and stunning setbacks.
These things have, point blank, held me back from greater success.
Yet they didn’t crush me. They could have; I’m not made of rock and titanium. I see people at my church struggle with many of the same challenges and it devastates their lives, leading to bankruptcy and homelessness, or severe chronic mental and physical illness. Sometimes they never recover.
The major difference, and the reason I’ve come through all of that okay, is because I’ve had good resources: family and friends who offered support, and money (and good insurance) to get help when I needed it.
Key themes in my story
Several key themes are woven through my story.
Timing. That I was born in 1967 is very important. I was about the right age for all of these things:
When I was a teenager, home computers became affordable to a family that had just emerged into the middle class.
When I entered engineering school, the Lilly Foundation was actively helping people in my situation pay for it.
When I entered the workforce, software companies were just starting to exist in quantity, creating demand for talent even during the recession we were in then.
When I began to mature in my field, the dot-com boom was forming and software companies were desperate for talent. It gave me the opportunity to move into leadership, which springboarded my career and, eventually, my income. That bubble burst, but another, more sustainable boom followed, and has created endless opportunity.
If I had been born a few years before or after 1967, I would have been the wrong age to fully enjoy most of these advantages.
Family. The family in which I grew up wasn’t perfect, but my parents loved me and raised me well overall. They didn’t have much money, but they were hyperfocused on making sure I got a very good education. They have been a source of support and encouragement throughout my life, especially during the most difficult days.
Natural abilities. I’m intelligent and intensely curious. My brain is wired just right to understand and enjoy technology.
Working/middle-class life skills. I know how to get to work on time and how to please my boss. I have good life-organization skills: there’s always enough food in the house, I pay my bills on time and have good credit, I keep my car and house well maintained (and do as much of the work myself as I can).
Good people. Just look at all the people who have helped me: The geometry teacher. The English professor. The boss who promoted me to management and taught me the ropes in software testing. The other mentors and colleagues I’ve alluded to who have elevated my abilities and helped me find new opportunities. Friends who supported me through difficult times and connected me with professionals who could help me.
Money. Just look at all the places money came from. My parents’ labor and sacrifice. A philanthropic organization. Federal and Indiana governments. And now, a healthy salary thanks to being a reasonably talented person in a booming field. Funds have been available to pay for college, for lawyers through my expensive divorce, and for healthcare professionals.
These incredible resources have provided a solid foundation on which I’ve been able to build a pretty good life — and recover from setbacks and difficulties.
My story through the lens of great wealth
Let me try to tell my story through one more lens, as best as I can: from the viewpoint of someone who was born into far greater privilege than me.
One of my college roommates was from a very wealthy family. To give you an idea of just how wealthy, he grew up in his own wing of his family’s mansion. Given my working-class roots, we were an odd pair of friends. I had no real concept of his reality, and he had little concept of mine, but we had Rose-Hulman and computer programming in common and it made our friendship work.
He could see that I had no clue about what success looked like in his world. Sometimes he gingerly offered me advice from his perspective. More than once, he coached me hard to save money and build capital. “When you get your first job, save up $10,000 as fast as you can,” he said. He detailed some ways I should invest it. “And then save another $10,000. And keep investing. It won’t take that long, really, for your money to grow to $50,000 or $100,000 or beyond — and then you’ll have money you can really work with.”
I couldn’t get my head wrapped around it. I came from a mindset of working to pay the bills — and if you had any left over, it went into a fully liquid emergency fund. And $10,000 was an unimaginable sum to me then. Even if I could save it, why would I tie it up in investments? What if something went wrong and I needed it?
He also talked to me about the importance of building relationships in my career, especially with VPs and CEOs. But to me, people with such lofty titles might as well have been 25 feet tall. Who was I to them? Why would they want to even talk to me? What did I have to offer them anyway? I’d rather let my hard work and eventual accomplishments speak for themselves.
That friend and I slowly drifted apart after college, I think in some part because he was living in his upper-class reality and I was living life according to my working/middle-class rules. From my perspective, I’ve done something remarkable: moved up one socioeconomic class. I am living successfully! But I think my friend was frustrated to see me squander my resources and not build a good network.
With my success of about the last 15 years and the world to which it has introduced me, my mind has slowly, finally come to see where my wealthy friend was coming from. You see some of it towards the end of my resources-and-luck story: how I do have VP/CEO contacts now, and I maintain those relationships. But even then, I did it the working/middle-class way: by proving myself through my work first.
– – –
So consider your story. What time in the world were you born into and how did that play into your success? Were you born into poverty, the working or middle class, or wealth? What life skills did your upbringing give you or not give you? Was your family emotionally healthy and a source of strength in your life? Did you have any major setbacks in your life? If so, were you able to recover from them? Why or why not? Do you have good friends, good colleagues, good professional contacts? Where has money come from in your life and how has it helped you get ahead?
Because no matter how hard you’ve worked, without those advantages you would be nowhere near as successful as you have been.
Even as I approached the building, all was strange. The front was still boarded up after last summer’s Black Lives Matter protests, the only such building on the block. My key card let me in the front door. It was irrational, I’m sure, but I thought it might not still work after not having used it in ten months. The lights were off in the lobby, as they were on my floor as the elevator doors opened.
My desk was as messy as I’d left it. I didn’t know when I took the week off in early March that I’d never use it again. The company ordered us all to work from home starting the Monday I was to return.
Fast forward to December. I received a fantastic offer from another company, one I would have been foolish to ignore. I took it. On my last day, I drove to my soon-to-be-former office to clean out my desk.
I’ve left jobs before, a dozen times. I have it down. I take stuff home little by little during my last two weeks so my desk is clear on my last day. After lunch I walk around and say personal goodbyes to everyone I can find who I ever worked with, wrapping up with my boss. Not only will I miss the people, who I genuinely enjoy, but also I want to leave a good final impression. The market I work in is small enough that I’m likely to work with some of them again. When I’ve said my final goodbye, I slip out the door.
This was all different. There had been a Zoom happy hour in my honor, which was a nice gesture. I said goodbyes in my normal meetings all during my final week. Anyone I didn’t see, I Slacked. But it all felt so disconnected.
Stepping off the elevator, the floor was silent but for the whoosh and hum of the HVAC. The last time I was on this floor it buzzed with such activity that I needed noise-canceling headphones to be able to focus. I sorted through my things, leaving a healthy portion of it in the wastebasket. I left my laptop and my key card on my desk, picked up my box, rode the elevator down, and walked out for the last time.
Monday morning I started at the new job. My commute didn’t change a bit: I came downstairs, sat at my desk, and started Zoom. But the faces I saw on the screen were all new.
The new company did a terrific job of onboarding, easily the best experience of my career. They committed to everyone’s first full week being nothing but group meetings with various people in the company telling us the company’s history and mission, how we make money, how administrative things work, and what our product looks like and how it works. We got to meet all of the executives.
Yet I kept wishing to see my old team in those little boxes. I really missed them! I always miss the good people I worked with when I leave a job, but never this acutely. But then, I didn’t get to say a proper goodbye.
I hired a software developer right out of college. He had a lot to learn, but he learned it steadily. Yet he admitted to me privately that he wasn’t sure he belonged. He thought that the other developers spoke so confidently and delivered so competently. He compared himself to them and, in his mind, came up wanting.
What he didn’t know was that I was leading developers for the first time. I’d been in management roles in the industry for a very long time, but always of testing and communications teams.
Worse, I hadn’t written a meaningful line of code in about a decade. Even then, most of that code was test automation. That’s not the same as writing product code.
Yet here I was, leading developers. The CTO who hired me wanted my skill in managing people, leading projects, and refining process. But I had so much to learn about modern software development. It was embarrassing to need the developers to explain the basics to me.
I told this young developer this story and admitted that I felt like an impostor, too. But I’d experienced impostor syndrome before. I knew that with effort and time I’d learn what I needed to learn and the feeling would abate. More importantly, even with all I needed to learn, I knew I had something valuable to offer right now. He did too, I told him.
We all figure it out as we go. In time, we build experience that lets us get it right more often.
What I wish I’d told him, what I’ve learned since then, is that there are three kinds of impostors. There are the impostors who don’t know they’re impostors. They’re so self-possessed that they overestimate themselves. There are the impostors who know it but do everything they can to hide it. They live in fear and anxiety that they will be found out. And then there are the impostors who know it, admit it to themselves, and sometimes even admit it to others. They’re the ones who can grow the fastest.
This young developer was the best kind: he admitted it. It let me tell him my own story, which helped put his mind at ease. Then it let us talk frankly about the areas where he felt like he didn’t know what he was doing, so I could pair him with other engineers who could level him up faster.
“You are unusually direct,” Elsa said to me. She was one of the first people I hired in my first management role, in the late 1990s. She said this to me on a few occasions as we worked on a large project together. I took it as a compliment then, but with hindsight I see that Elsa found my forthrightness to be challenging.
I say half-jokingly that I was this direct because I have hillbilly and blue-collar roots. My dad grew up in the hills of West Virginia. His family moved to Indiana to find factory and construction work. Dad worked in a farm-equipment factory while I grew up. In the culture I came from, anything less than saying it straight — no matter how much the words hurt — is seen as being untrustworthy.
I was proud of my direct manner. I believed that my forthrightness was good and valuable. It came from a place of wanting good outcomes for the company, customers, and my co-workers. I wasn’t trying to be a jerk, but that’s how I was sometimes perceived.
I’d been a manager for about 10 years when the fellow I worked for at the time said it to me: “Jim. You’ve got to stop leaving dead bodies behind when you talk. Learn some tact.” He told me he’d like to see me move up in the organization, but not while this behavior stood in my way.
That got my attention. I had been pitching fastballs at peoples’ foreheads. That boss coached me in throwing drifts that others can catch. I’ve practiced it ever since, and have built reasonable skill. It has unlocked all sorts of opportunity for me. It has helped me build influence and trust.
It took a long time for more nuanced communication to not feel wrong. It turns out I’m not among my hillbilly family, and I’m not working a blue-collar job. I’m working with midwestern professionals, and the rules are different.
I revert to my natural form when I’m anxious, over-stressed, or very tired. Those are not my finest moments.
But there are times when speaking directly is valuable. Emergencies are one such time. A couple companies ago I ran QA. Production went down while all of the ops managers were at a conference. I was ranking manager, so I dove in and, using my natural directness, led the team to quickly find root cause and get Production back up again. One engineer praised me: “You came outta nowhere and crisply and efficiently drove the train back onto the track. I’ve never seen this side of you!”
Another time is when I think I see something critical that nobody else does, and nuanced communication is not getting the ball across the plate. A flat statement can grab attention and change the conversation. It can also blow up in my face, so it’s a calculated risk. I’m hoping it works because it seems so out of character. “Whoa, Jim is really strident about this one. He’s usually so collegial. Maybe we should listen a little more closely.”
Finally, sometimes you have to say a flat “no” to a challenging request. I try very hard to find a way to say yes while highlighting the tradeoffs I or my team will have to make. “Could you deliver this feature two weeks earlier?” “Yes, if I pause work on this other feature.” Or, “Yes, if we trim scope and accept greater quality risk.” Or, “Yes, if we can flow some of the work through this other team.” But if scope, quality, and team are fixed and don’t support the timeline, I’m left to say no, and I do so plainly.
I will always wish I could be direct all the time. It’s how I’m made. But I care more about being effective than leaning into my basic nature.
This post expands on a comment I left on another post on this subject, on Johanna Rothman’s blog, here.
Lots of people in our industry have accomplished much, made a lot of money, and even achieved status or fame. It seems like lots, anyway. It’s probably a small but highly visible percentage. Whichever it is, it’s easy to wonder in this industry of plenty why that can’t be us.
When I remove the incredibly successful from the picture, it’s easy to see that I’ve done well for myself. I’m a middle manager of software engineers making a product you’ve probably heard of, in an engaged and positive workplace. We all make an upper-middle-class living.
Yet I sometimes wonder why I’ve made it only this far, why I’ve not gone farther. And I wonder whether I’ll be able to sustain my career as it enters its waning years.
You see, today marks 30 years that I’ve worked in the software industry. It boggles my mind that I’m only two-thirds of the way through my career — I still have 15 years to go before I’m of normal retirement age.
Fortunately this is all I’ve ever wanted to do, ever since I taught myself to write code in the early 1980s. I went to engineering school to get the credential I needed, but graduated during a recession when jobs were scarce. In a nationwide search I couldn’t find coding job. I managed to land job in the software industry writing manuals and online help, and I was grateful to get it.
I liked the work and became quite good at it, so I kept at it for eight years. Then I transitioned to QA, where I led functional testing, test-automation, and performance-testing teams. I did that for 17 years. And now I’ve transitioned back to my roots in a way by leading engineering teams.
I’ve lived through crazy growth and sudden downturns in the industry. Several times I’ve needed to find a job when one ended unexpectedly; several times I’ve been poached away to a better opportunity. I’ve worked with good people who have taken good care of me, and with charlatans and egomaniacs who stabbed me in the back.
Sometimes I’ve had the tiger by its tail, and sometimes the tiger’s had me in its mouth.
Dozens of people have reported to me since I shifted into management. It’s a small tech community where I live; I bump into many of them a lot. Some of them are still individual contributors, some of them have become managers and leaders, and a few of them have gone on to even greater careers than I’ve had, reaching VP levels or reaping tidy sums when their startups exited.
But I’ll bet every last one of them has had good luck and setbacks all along the way, just as I have. We all sometimes have to figure out how to move forward from here in our careers. We all have to figure out how to stay relevant and vital, especially as we age.
I’ve been in management for 20 years, during which time I focused on being the best leader I could be. It has served me well.
I couldn’t both become a strong leader and keep my technical skills current. I struggle a little bit to swim as fast as my peer engineering leaders, most of whom have written code recently. I can see it’s time to rebuild my technical skills. I don’t expect, and I won’t try, to become the equivalent of a senior engineer. But to have a solid understanding of the technologies involved in my company’s product, to better evaluate the code of someone on my team and maybe even to be able to fix a bug, to be able to write a SQL query more complicated than SELECT * FROM table_name; — it’s time. I’m a little daunted, but in I go nevertheless.
I’ve learned a lot in 30 years. In many ways, I’ve become wise. But I’m still trying to figure things out as my life and career unfold. I can see that this never ends.
When you leave a job, you leave behind the relationships and reputation you’ve built, and the mastery you’ve gained over the work. It’s hard to leave them behind, and it takes a lot of time to build them back in your new gig. Even when you’re positive it’s time to go, it’s hard to lose all of that. It might make you hedge your bets and stay.
It’s said that people don’t change until the pain of staying the same is greater than the pain of changing. I think it’s similar when you contemplate changing jobs: the difficulty of staying or the benefit of the new job needs to be greater than the challenge of rebuilding relationships and expertise.
Bad reasons to stay
You might also resist leaving because you feel you’d let your coworkers or customers down. But if you stay for that reason, you are taking on too much responsibility for the company’s functioning. It’s the company’s responsibility to make sure it can function if anybody exits. I’ve seen people at all levels move on, from associate engineer to CTO and even CEO. Every time, the company found a way forward.
Moreover, nobody expects you to work there forever. The day you were hired, your boss knew he would one day accept your resignation — unless he were to resign first. If you’re good at what you do, your boss will be wise to work to delay that day as long as possible. But it will eventually happen.
The 90-day countdown
Changing jobs is a big decision. Give yourself time to be sure it’s the right choice — whether you’re fed up and ready to ragequit, or hedging because you want to keep the good things you’ve built up.
I use a 90-day countdown a colleague shared with me long ago:
When you think it’s probably time to leave, set a 90-day counter in your head. Decrement the counter each day until one of two things happens: conditions improve or you see a good path forward, in which case you stop the countdown; or the counter goes to zero, in which case you update your resume, reach out to your network, and get out.
90 days — one calendar quarter — gives you enough time to avoid acting out of pure emotion so you can think it through clearly, and gives difficult circumstances a chance to change.
Thanks to this song for giving me a great post title.
I leave jobs. It’s what I do; in my career’s 29 years I’ve worked for ten companies. My longest tenure has been just over five years and my shortest was 14 months.
(To my boss, and to my team, who are almost certainly reading this: no, I’m not thinking of quitting!)
Usually I’ve moved on to gain new experience or a higher position. A few times I’ve quit because the situation had become untenable — once for a relentlessly crushing workload; another time because of a micromanaging and mean-spirited boss. Twice I’ve been laid off when a company fell on hard times.
During my father’s era, loyalty to an employer was lauded. But today, and especially in our industry, spending too much time at one employer can make your skills look stale. That makes it harder for you to land a next gig.
But when is the right time to go? It’s often hard to know, but it’s hardest in the first job you take after college. It’s easy to form an attachment to the employer and your experience there, and stay too long. I did that myself.
It is easier the second time you quit, and the third. Soon you get a good sense of when it’s time to go. Here’s what I’ve learned.
Sometimes a company pushes you out:
You struggle to get behind major changes. Companies regularly adjust course, sometimes dramatically. When it happens, can you get behind the new direction? If you don’t think the new strategies will work, or if you find some of them to rest in a moral gray area, make your concerns known. But if things don’t change, you should probably find a different company where you can be all in.
You are constantly frustrated with the way you have to work. If you’re comfortable in a high-process environment, low-process environments will feel too chaotic for you. If you enjoy high autonomy and low structure, you’ll feel strangled in a company with rigid hierarchy and lots of rules to follow. Or if you are highly competitive, an environment that values close collaboration and shared success will drive you nuts. Try to adapt to the environment, to grow through your limitations, and to influence change where you think things can be made better. But if you constantly have to be someone you’re not, find a company where you can be you.
The company seriously struggles financially. Every company goes through tough times, so don’t be quick to bail. But you should see your company making strong steps to bring good results back. Some companies aren’t transparent about their finances or strategies, so keep your eyes open. Look for new initiatives that gain traction. Watch your sales team — their growing happiness or deepening despair is a bellwether. But no matter what, persistently poor financial results will result in layoffs, or worse.
You don’t get along with the boss. Try hard to work things out first. Get some feedback from trusted colleagues about how you might be contributing to the difficulties, and fix those things. But sometimes you and your boss will just never be a good fit. And once in a while you will simply work for a truly awful boss. In both cases it’s time to go.
You see or sense moral rot in the company. I once worked for a company where the CEO was unable to not sexually harass his assistants. Finally one sued him; he got his entire executive team to lie about it in court and he got away with it. I worked for another company where the sales team would go to the annual user conference and spend their off hours, it was strongly rumored, drinking too much and sleeping with each other and with customers. It can be hard to separate hearsay from fact, and don’t spread rumors. But watch closely for signs of bad behavior, because moral rot will do your company in. It absolutely undermined the first company, and just the rumors in the second company seriously damaged the culture.
Sometimes your needs pull you out:
You aren’t growing in skills, pay, or title. Your career should progress. What that looks like depends on what motivates you. I like to get better and better at what I do, and if that’s not happening I get bored and leave. You might just want to make more and more money or rise to the top of the corporate ladder. Your growth might stall for a while in any job, but if it stalls for too long first ask trusted colleagues and managers what you might be doing to block your own growth, and fix those things. If that well is dry, perhaps you’ve gone as far as you can go and to grow you’ll need a new opportunity.
You need a job that won’t challenge you. This might sound strange. But if your personal life ever goes seriously sideways you might need to put career aspirations on hold for a while. In my mid 30s my first marriage ended in an awful mess. I ended up working in IT for a large insurance company, where the pace was slower and the work itself wasn’t that hard. I came home at night with the energy to focus on getting my life back together. Eventually my life restabilized and I wanted to grow in my career again, so I left.
You want to work for a company whose culture or product aligns with your values. Where I work now we build a product that aims to make the work life better for employees everywhere. We attract people who want to be a part of that mission. If you see another company with a mission that resonates with you, by all means, find a job there!
You want to work with more modern technologies. You might follow one tech stack through your career, or you might become a polymath and ride the cutting edge. If the latter appeals to you, get out when your company’s technologies become widely adopted, and find the next new thing.
You want to work for a company that is succeeding wildly. It might matter to you to be a part of the next big success story. If you sense another company is a rocket on the launch pad, and that excites you, what are you waiting for — get in over there!
In my next post, I’ll give some tips about how long to wait before you launch a job search, and how to manage your feelings about leaving.
Thanks to this song for giving me a great post title.
In a recent blog post, Johanna Rothman wrote about paying it forward in our careers and in life. (Read it here.) Through paying it forward, she says, we offer people lucky breaks. When others pay it forward, sometimes we get the lucky breaks.
I add this: sometimes when you pay it forward, it goes full circle and creates lucky breaks for you. Here’s a story of a time that happened for me.
In my first management role, more than 20 years ago, I got to build a small team from the ground up. I wrote that story here — that team and the work we did remain one of the brightest memories of my career.
I wanted to build the kind of team I’d want to work in — one of transparency and autonomy, where we could do very good work yet go home to our families at a good hour each night.
I hired Mary Ellen first. She lacked the technical skills I was looking for, but was otherwise qualified — and whip smart and deeply resourceful. So I took a gamble and hired her.
She was a home run hire. She picked up every needed technical skill quickly. Her work was nuanced and of impeccable quality. She even helped define team processes that let us run more efficiently and effectively. We couldn’t have done it without her.
The team was quite sad after a few years when I was promoted to a different role and was no longer their manager. It was a great compliment when they told me that our time together had been the best at-work experience of their careers.
That company didn’t make it through the dot-com bust and we all went our separate ways. I wasn’t very good at keeping up with my network then and lost touch with Mary Ellen. Seven years later, I got an email from her. “There’s a leadership role open where I work now, and it looks perfect for you. If you’re interested, I’ll put in a good word with the VP, because I’d love to work with you again.”
I was ready for a change so I interviewed, and I got the job. It was a fabulous role for me and I was very successful in it. The company itself was successful enough that the founders took an exit. I was a late enough hire that my cashed-in stock options didn’t change my life. But the founders and all the VPs ended up being movers and shakers in the startup scene in my area. Those contacts have helped me immeasurably as I’ve continued my career, offering coaching, introductions, and even job offers.
The moral of the story is to treat well the people who work for you! Treat everybody well. You never know when it will come full circle.
Yet I’ve noticed that I’ve continued in my career that I work increasingly with people much younger than me. Today I lead a team of software engineers mostly in their 20s. I know of only one fellow on the team who’s older than 30. It was much the same in my previous job, and in the job before that.
I’ve long assumed that engineers my age all still worked in .NET shops. .NET was new, hip, and cool when I was in my early 30s. Where I live (central Indiana), companies adopted it readily and so most then-young engineers built their careers on it. I worked for several .NET shops in a row. Some of those companies still exist, and their products are still built on .NET.
So I searched LinkedIn for names of people I worked with years ago. Some of them are still writing code. A few of them are in some level of management. But the rest aren’t on LinkedIn or have left the industry.
I don’t know why. Do you? Especially if you’re older than 35: where have all the older engineers gone?