016. [Q&A] Startup-Building and Navigating a Tech Career

I recently was a featured guest for Elpha Office Hours – Elpha is a community for women in tech to talk candidly and lift each other up. The Office Hours are in a “AMA” (Ask Me Anything) format – which, combined with the ability for members to ask questions anonymously makes possible for some juicy content!

I was actually one of the early hosts of Elpha Office Hours back in January 2020 – and the timing felt right for a redux. Below is my intro for the December 2023 edition, along with some selected questions + answers (lightly edited for clarity). Enjoy!?

Hi Elphas!

I’m Jennifer Kim, the founder and CEO of Workflow , where we’re fixing the way tech companies hire and scale. You may know me from Twitter or my newsletter, Safe For Work, where I share stories about the human side of working in startups.

Even though this is an AMA, I’d really love to hear about your experience!

Startups can be incredible, career-defining opportunities, but the reality is that most of the time… startups are brutal workplaces. And often, this can be traced to a poor foundation in People.

Unfortunately, most startups aren’t strategic at all about People/HR practices, it’s common to simply copy-paste Big Tech Co playbooks. But this doesn’t make sense! Startups are a unique environment with a different talent, goals, pressures, so you gotta get creative. For example… many founders’ neuroses and worst qualities can be inadvertently replicated in a company culture and processes as it scales – unless there’s a strong People function to guide and counteract that.

I’m a former Head of People who got tired of seeing the same problems over and over again, and the loss of potential of great startups who don’t get to meet their full potential due to People problems. I founded Workflow to partner with the next generation of unicorns and help them learn from other companies' past mistakes.

Raise your hand if you’ve ever been disappointed by an experience at a past startup, especially related to management, culture, diversity, etc. Share your story in the comments and let’s talk about it and see if we can figure out how it could’ve gone a better way ??

Q: "Should I stay or should I go?"

Anonymous: I’ve worked in startups for years and years (their entire career). Do you think a shift to a large org would be a positive change for me? I'm wondering if it'll be too much of a culture shock after years (decade+) of being an early-stage employee on a small team. At the same time, I love the idea of having more support, more mentors, and more learning opportunities.

If you do think it's worth pursuing, how would you recommend a startup junkie position herself to be attractive to a larger org? Especially if my current title history isn't as clean cut as employees who have been climbing a corporate ladder for the last 10 years?

A: Hi Anon! Great question.

Can I be honest about what I'm hearing? Sounds like you know what you want to do: you’re ready for more support, mentors, a different learning environment, etc. But maybe, what’s (very understanbly) getting in the way is concern about the potential culture shock, due to the fear of the unknown. I get it! Smart, ambitious people take their career seriously and it can be really intimidating to make big career jumps.

So here’s the short answer to your Q, on whether I think this would be a positive change for you. Well, I don’t get to say that, you do :) And based on what I’m hearing, you’re ready for it – then you absolutely should explore that path.

But my longer answer is an invitation to go deeper and reflect on why you’re ready for this change. I don't know you, so I can only make some guesses based on the hundreds of conversations with folks in similar positions, navigating a tech career. One factor could be… maybe you’re tired. That’s a real thing, especially if you’ve been in one early-stage startup after another. Some of these may have even been poorly run, which can be an exhausting experience. Don't get me wrong, I love early-stage startups. It's fun, fulfilling, and even career-defining. AND it can be totally unsustainable when you don’t have the right support structure, stability, etc, So, being bit burnt out could be part of the unspoken dynamic here.

Here’s another possibility – you know, the culture of startups involves a ton of bravado: We’re so hardcore! Hypergrowth! Mission driven! To the moon!!! All of that can be a hell of a ride.

But here's the undeniable reality: Companies can grow exponentially, but humans cannot. There is nothing wrong with this fact, it’s simply a biological limit. It is theoretically possible for me, a lifelong couch potato, to become an Ironman athlete – but it would take a lot of time and training. Startups are like that, except they’re expected to grow unreasonably in a VERY short amount of time. The environment is designed to be a pressure cooker, and there’s nothing wrong with needing a change after a decade (!).

Sometimes growth means not just infinitely climbing upwards. Growth should include periods of moving laterally, or even staying put just for a second. I really believe that – When I think of all the times I've been either burnt out or just needed to take a different pace to my career, the periods of maintenance mode were invaluable. Of course, when I was actually in it, I was constantly kicking myself for not working hard enough or not meeting some imagined expectations (I don’t recommend this part). But when I look back now, those periods ended up being the springboard to the next great thing that I ended up doing. So maybe switching to a bigger org environment could be that for you.

That was a long answer! I’m making some assumptions about your situation, but I hope the perspectives were helpful. As for the second part of your question… you know, for the hiring company the usual concern is the other way around ?? i.e. A Hiring Manager at a startup asking, “But will this Big Company Candidate be able to adjust to our environment?” but not vice versa. I get why this might be intimidating, but it may be less of an issue than you might think. So maybe it’s less about what skills you do/don’t possess or your adaptability, and more about positioning yourself and employing some good ol’ job search strategies to land in the best place possible for you. Here's an article that I wrote recently that might be helpful, plus I definitely recommend you get some help around the “unclear job history” piece, because resume coaches exist for this exact reason! Feel free to DM me for some referrals.

Overall, the opportunity here is to pause and reflect on the bigger questions about why you're ready to move on which will serve you and your career well. Get curious about your hesitations, fears, and narratives, but to me, it sounds like you know what you want and that's the most important part. I wish you the best of luck!

Q. Organization-building opportunity at a 80-person company

CEO: Thank you for taking the time to offer your expertise! I'm currently running a 80+ fully remote, distributed, series B company and we're struggling to find ways to level up our remote employee experience. For example, like you said, big co playbooks often don't translate and I personally hate performance reviews but what is a great substitute that scales? Also, when we have our annual IRL retreat it's electrifying and 'fills our cup' as an org for a while but inevitably, we lose that magic throughout the year as we go back to our remote set ups. Is there anything you're seeing out there to help build real connections in a remote culture and what are your thoughts on remote perf. review alternatives? TYIA!

A: Thanks for the question! The short answer is we should talk more because I think there's so much we could get into, and it sounds like you’re at the right stage for laying down some important People foundations. When it comes to People work, some of the systems/processes are fairly standard across companies, but quite a bit – and the most interesting and high-potential opportunities – will be specific to your company. So it’s not just cookie-cutter, but a chance to reflect and build upon the strengths/opportunities of your team and context. So my DMs are open for a follow up conversation – but first, I’ll actually answer the question for real :)

First, I want to note that it's fantastic that your IRL retreats are so effective. I’m a nerd for retreat design and facilitation, so it’s music to my ears! Could you look at doing it twice a year? If not exactly the same, and it doesn’t even have to be in-person/same format.

What I’d do next is to take a closer look at what exactly makes these retreats so electrifying and cup-filling. This would entail some research to figure out the relevant key data (quantitative and qualitative) as well as insights – for example, was it about the level of social connection? Or was it more about the opportunity for each person to build their connection to the mission? Professional development/team-building? Or maybe y’all just hung out at a luxury resort and that was enough ?? Point is, what makes for a very special experience will vary by who the group is, so once you can identify the insights, you can then brainstorm ways to amplify that everywhere in remote environments.

The next point to consider as a company navigating effective remote work is the level of People Team resourcing. We’re still in relatively new territory for so many companies being remote – it really used to be a niche thing – and there’s a lot still being figured out, collectively. For example, I’m of the belief that remote work is People & Culture work on hard mode. And I say that as a remote work advocate! The reality is, remote environments require MORE investments in the social and communications infrastructure, and these don’t just grow on trees – they need smart teams tending to them, and that’s usually the job of the management and People teams in collaboration. The problem is, our industry has LONG under-invested in People/Ops teams, leading them to be thinly stretched – and remote work only increases that gap.

That’s a long way of saying… I would invite you to consider your current People team and the plans for it in the future. How might they set up for success, where they're not just boggled down in infinite administrative tasks and compliance, but actually able to think and build strategically about employee experience. Unfortunately this is still pretty rare outside for Workflow clients, for whom my team and I provide the additional People resourcing and the infrastructure/frameworks, which allows these companies to build a People, Talent, and Culture function that’s actually strategic, not just an afterthought.

OK, this answer’s already long enough so I’ll have to save the info on performance reviews for later! Overall, I’d say it sounds like you’re at a perfect time to really prioritize People work - you’re at the size where the team can be fairly tight-knit and be the foundation for a strong culture. The opportunity then is to build on it, to set your team up for scale to hopefully much more!

Q. Performance & RTO ponderings from a former roommate!

Hey Jen! Former roommate here from Hayes Valley/Lever days - nice to see you on here! There are so many things I could ask about now that I'm in tech (though they could really apply to any point in my career):

1. I find that our performance review process and calibration meetings are often "success theater". No one wants to look like they're not achieving. Furthermore, I find we're not willing to be candid about real blockers to our work and how we can solve them together when it comes to talking with execs and xfn partners, though these conversations do happen 1:1 or at a team level without much resolution. What are your tips for building a real culture of feedback, reflection, iteration, and acknowledgement?

2. Our return to office strategy was first decided to be flexible depending on the exec, which means that some teams are "required" to come in 2 days a week (mostly EPD) while others are not (especially customer facing teams where the rationale is that the bulk of their work happens with external parties). I suspect this is changing soon for us, which I'll be interested to see. I personally prefer not to go to an office more than 2x week, which balances my focused working time with the office time where I'm largely either socializing, distractedly working in an open office plan, or frenetically running from room to room because I still have back-to-back virtual meetings. What are your thoughts on RTO, and who's doing it well?

A: Hi Emily!! What a nice surprise. I remember our old roomie mentioning at the kitchen table about how well you’d do once you could break into tech – and look, killing it! Congrats! Plus you’re now part of commiserating about tech company culture and management practices, lolll.

Okay, on performance. I’ve also long been talking about how performance reviews are… well, performative. They don’t do what they say they do. Ostensibly, it's a process for rewarding high performers, providing employees feedback, etc. But in reality, I think it ends up being designed + executed from a very defensive place. Tech companies hire hundreds, thousands of really ambitious people, all of whom want to be promoted every six months. So it's a system designed to make the minimal number of those possible, while keeping the rest of the workforce satisfied enough to not leave. But anyway, you don’t need me philosophizing all day :P

So let’s acknowledge the baseline, that performance isn’t done well at most companies. There are some who manage it well enough, but that quality is hard to maintain in hypergrowth. So I want to validate how frustrating this is – when performance processes are really important and can be really impactful. But…… and maybe this is harsh, but I think it’s also important to acknowledge the limit of what individual employees can change, especially when it comes to org-wide HR practices.

Don't get me wrong. I do absolutely think employees should be giving the executive teams management critical feedback. Exactly what you just said here about how it's hard to be candid and that the process is blocking work! AND, it’s not owned by you, you don’t have control over it. Your job is to deliver the feedback, but if the executives/People team either don’t or can’t respond to it well, that’s not your responsibility.

I think success in a hypergrowth environment sometimes means having a realistic view on what is actually in your sphere of influence/control, and what you can let go. If you're a manager, you can do a lot to build a real culture of feedback and integrate your values IN YOUR TEAM - then hopefully, that influence can spread. But, sometimes the best you can do is surface that feedback.

Maybe this is too harsh. But I’ve seen too many people get burnt out from overfunctioning around ineffective executive and People teams. Whether it’s because they don’t get it or they do but they simply don’t care, that doesn’t mean employees should pick up the slack and responsibility. It’s a delicate line to manage when you’re someone who does really care and are inclined to take on a lot of responsibility at work.

Your second question about RTO – this is also related! There are a couple of things in your paragraph that make me raise an eyebrow. Inconsistent “requirements” is a yellow flag to me – it could mean the HR and management teams were not courageous enough to actually draw a line in the sand and own their decisions, even if unpopular. Wishy-washiness in org policy making causes MORE confusion and disruption to productivity, especially given that employees are very sensitive to perceptions of unequal standards.

Just this week I wrote an article about RTO! ? I totally get why you and many others prefer WFH, given that we've all adjusted our lives around it in the last few years. So if a company decides to RTO, they have the responsibility – and really, an exciting opportunity – to then provide an alternativeI to WFH experience that is actually appealing. It means getting creative in designing an effective in-person collaborative environment that actually makes people want to go in… or at least, be less resistant/resentful about it!.

Check out the post and maybe drop the link to your management/HR team as well ;) But I hope it goes well! It's a really tricky time. We're all still in a transition after the shock of 2020 and all the fallout. And it's gonna take us at least a few more years to sort but in the meantime, hope you can find what's best for you. So nice to hear from you!

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Jennifer Kim is the CEO/Founder of Workflow , an education and consulting company that trains the next generation of startup leaders on all things Recruiting, People Ops, and DEI. Through its flagship program, the HireEd Accelerator, Jen and her team have taught hundreds of startup leaders to make hiring a competitive advantage. Previously, Jen was Head of People at Lever and advised dozens of top startups. She is known for her hot takes on tech industry and culture as @jenistyping.