In the last few years, I’ve had approximately 37981 calls1 with job seekers, career pivoters, and recent or near graduates wanting to “break into” product management2. I’ve learned a lot from these conversations about the shape of the tech job market, the slippery lore around a “successful career,” and the value of co-creating stories about ourselves as professionals. Supporting people in vulnerable and expansive moments in their careers has been a renewable source of energy for me.
Despite the breadth of people and situations I’ve worked with, there is one piece of advice I’ve found to be applicable and useful for almost everyone: know what you’re optimizing for.
“Optimize” deserves the cringe reactions it often receives as a verb recklessly wielded by corporate “growth” teams and VCs for years, but I keep using it in these (admittedly tech-oriented) conversations because it’s tidier and plainer than saying:
Define your values, clarify your responsibilities, and determine what role work currently plays in your life and how you do or do not want that to change in the next chapter.
When I talk with someone on sabbatical or in an intentional recovery period between jobs, they’re much more receptive to this headline question than someone who was caught up in a shock layoff or who’s been unsuccessfully interviewing for months and months. If you aren’t feeling mostly secure, psychologically and financially, you won’t be able to think generatively. Your answer will likely be some version of: “I am optimizing for a paycheck commensurate with my skills and experience in order to simply stay afloat in this late capitalist hellscape, but thanks for asking.” This is my plea for you to go through this thought exercise while you are already in or once you recover to a space of security. If you are a person for whom work is practically a hobby and not a necessary exchange of labor for life-sustaining dollars and (in the U.S.) health insurance, please understand this advice isn’t for you.
These conversations connected me with people actively job searching, networking closer to a target role or organization, and conducting unhurried explorations of fields, roles, or brands that interest them. When I ask, “what are you optimizing for,” I’m not asking for the job title they’re pursuing or their preferred salary band. (I’m not a total ass. We’ve well covered logistical details by this point in these conversations.) I’m asking them to reflect back to me the critical thinking they’ve done about what they want to change in their lives–if anything–as a result of the professional change they’re seeking. Let me share an example.
I spoke with an almost-graduate of a prestigious graduate program that positions itself as training and delivering the next generation of product managers. This person had been frantically applying for PM jobs for a couple of months despite still being in school full-time and having a standing offer for a company they’d interned with to join as a business analyst. We’d talked through their dream roles and companies as well as the approaches they were using to find, apply to, and interview for jobs already. When they’d down-cycled and talked through all of the uncertainty causing them anxiety I was able to nudge them toward more generative ideation by thinking critically (sounds contrary! it isn’t!) about what they really want next. The conversation went something like this:
CB: “Sounds like you’re really committed to the PM title. Let’s just assume one of these roles works out and you start as an associate PM at XYZ brand. What do you want to get out of that experience?”
Them: “I want to learn how to do PM for real and not just in the limited scope of an internship. I want to learn from the pros and figure out how to be great at it.”
CB: “Cool. Learning makes sense as a top level goal. Why?”
Them: “What do you mean? Why do I want to learn?”
CB: “Yeah, exactly. What are you going to do with what you learn? What’s going to be possible for you once you’ve learned those things in that specific context that isn’t possible right now?”
Them: “Oh. A promotion to product manager, I guess. Either at XYZ or somewhere else.”
CB: “Cool. Why do you want that?”
Okay, maybe I am kind of an ass. And you’re correct if you’re sniffing out some similarities to five whys. But hear me out: achievement and promotions for the sake of achievement and promotions isn’t what keeps most people curious about their work or motivated to bring value to their teams and organizations. Money isn’t either. There’s certainly a threshold of money that–until achieved–is wildly motivating, but in knowledge worker jobs at tech companies, that box defaults to checked.
A nuance that immediately distinguishes confident, experienced job seekers from the rest is their ability to:
- Crystallize their values and requirements for how their next job/chapter/professional endeavor complements their lives and their goals (Homework; not discussed in 99% of interview contexts)
- Explain or hypothesize (when role details are sparse or a hire is opportunistic) in specific detail how their unique skills, perspective, drivers, and experience connect with the role or business challenge they’re pursuing. (Prepared for ahead of interviewing; verbalized in 99% of interview contexts)
Does this feel scary and limiting? YES. Does doing this automatically rule out certain jobs from your consideration and identify you as a great OR terrible fit to recruiters? YES. These things are true. This is why this advice isn’t useful when you’re desperate and simply looking for work to stabilize your life. Come back to it later.
Going through this exercise will make you a more attractive and sellable candidate for the jobs you’re best suited for. Period. You will be more quickly eliminated from consideration for jobs you are poorly suited for, which is a win for everyone. Depending on your job search and application tactics (another post another day), you might receive many, many more “thanks for applying, but…” than “we’re excited to move you to the next round” responses. This is an expected outcome. Brace yourself for it.
Curious how the rest of the conversation with the almost-grad went? After I asked them why they wanted to be promoted and they laughed and said because it meant they were succeeding, I pushed them toward the central question:
CB: “Listen, it’s normal to want to know you’re doing a great job. I get it. But I struggle to believe that validation from your manager is really all you want. What are your drivers or motivations one level up? If you remove any specific job or company or title from consideration, what is it you want your job to do for your life?” Do you want flexibility in your schedule? A fully remote role that allows you to be home with your dog? A metric ton of cash as quickly as possible so you can move to Europe and spend your early retirement renovating a raggedy villa? A mental challenge so your brain is quiet by every evening and you can just enjoy your cat and playing guitar?”
Them: “Oh. I’m not sure. I think–I think I just want to make enough money to be able to pay my student loans and save up a down payment for a house. It would be nice to know I’d have my evenings free because I play league basketball. I also want to work somewhere that I’m able to learn about the practice of product management because I know there’s a lot I don’t know yet. And working on products with a lot of users would be cool because I like running experiments and using analytics.”
CB: “GREAT. Those are really clear, orienting goals. Is it fair to rephrase that and say you are optimizing for salary, predictable working hours, and learning about how software products gets built especially where analytics, experimentation, and data-informed decisioning are central to the process?”
Them: “Yeah, that sounds right.”
CB: “Do you have to have a product manager title or work at XYZ to achieve those goals?”
Them: “No, I guess not. No.”
CB: “Sounds like you have a lot more options than you expected. And some great questions to ask when you’re interviewing. Ask people when their days end and how consistent that is. Ask what coaching, mentoring, or internal learning and development programs exist. Ask if there’s a defined path for new hires in roles like the one you’re applying for to move into product management, or what would be required to define one. Tell your interviewers you’re keen to learn from them, and ask how they mentor new hires.”
They wound up taking the business analyst role because even though the title wasn’t what they’d initially wanted, the job was with a mature company investing heavily into internal analytics and experimentation practices, the entry salary satisfied their requirements, they had enjoyed learning from their coworkers during their internship, and they knew the company’s working hours and culture supported their outside interests. They also asked their hiring manager and learned that they’d facilitated the transfer of two people from their team into product management roles within the last year and would be happy to help them learn and prepare for that. Could this person have stayed the course, continued networking and applying, and eventually landed a PM role? Of course. But that isn’t the point.
It is my dearest hope that this question finds you when you are ready and that the practice of asking it unburdens you from arbitrary constraints, brings you joy in the creative possibilities you imagine for yourself, and supports you in crafting a new story you’re excited to share. Please tell me about it? 🩵
- This data has not been fact checked and cannot be used as evidence in a court of law ↩︎
- I’m begging you, please don’t say this phrase out loud, write it in a LinkedIn post, or use it in an industry Slack channel. It only emphasizes your unfamiliarity with your audience. If you do choose to use it or anything remotely similar, please prepare a compelling, incisive answer to someone asking you, “why?” ↩︎