3 Ways to Avoid a Job Change Misstep

Self-awareness and due diligence can help you side-step instead of misstep

Over the last few months, I’ve had dozens of mentoring conversations with junior product managers, senior PM’s, and product leaders. They are all working hard to have an impact in their day job, but in parallel many are thinking about a job change. It’s not a topic they can talk about freely at work, so they ask for my advice about how to think about a change and how to avoid making the wrong one. This is the framework I share with them, a framework I’ve forged from my own missteps and successes.

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1. Don’t jump at the first company that tries to recruit you

There are many triggers for a job change, but a common one is simply that another interesting company reached out and showed interest in you. It’s flattering. Talk to them and be open to a conversation with a recruiter or hiring manager, but don’t put on the blinders and don’t plunge full speed ahead with that company without going through the other steps of this framework.

The risk of going too far, too fast with one company is you may get an offer before you’ve had the chance to explore other companies and get a sense for what’s out there. You’re faced with the tough choice of either accepting a potentially sub-optimal offer at a sub-optimal company vs. missing out on what might be the right opportunity because you want more time to play the field.

Slow your roll and leave time for other companies to catch up. Your best outcome, and best negotiating position, will come from having multiple compelling opportunities you can evaluate at the same time. Note: I am not advocating for a shotgun approach where you interview with a bunch of companies at the same time purely to get competing offers you can leverage against each other.

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2. Decide what you’re optimizing for

For a moment, forget about the company that reached out and the industry they’re in. Put them out of your mind. Ask yourself, “What do I want to optimize for in my next job?” Write down a ranked, numbered list of what is most important for you in your next job - maybe the top 3-5 things. Doing this narrows down the decision space and makes evaluating companies and opportunities much easier.

If the company recruiting you or the role they’re recruiting you for doesn’t meet your #1 criteria, it’s not the right place. If it only partially meets your #1 criteria, you need to try to find a job that meets it fully and best. If you join a company that doesn’t meet the top criteria you’re optimizing for, you only have yourself to blame.

These are some of the things you may be optimizing for, and ways to evaluate whether a company might meet them.

Learning PM Skills. This is a GREAT thing to optimize for if you’re a junior PM early in your career, or if you’ve been a PM for years but never worked for or with PM’s you’d consider great role models. Reading blog posts, joining Lenny’s Community, and watching Gib’s talks should all be mandatory for PM’s, but they’re no substitute for working with and for great PM’s and seeing how they operate first-hand.

Here, the advantage goes to working for a larger organization (e.g. Amazon, Meta, Google) with many PM’s. These companies are crucibles that forged the PM leaders that advanced within them. At a big tech company you can learn from PM’s around you, see which PM leaders are the strongest, and look for opportunities to work and learn directly from them. Having a top big company name on your resume also gives you a tailwind when you go to make your next move.

You may learn good PM skills at a small company, but you’ll be learning primarily by doing and your learnings will primarily be from your own work. You won’t get the development and you won’t get the benefit of learning from many other PM’s at a larger company.

Working Directly with Software Engineers. If you don’t work directly with software engineers, the single biggest thing you can do to make yourself a more valuable product manager is take a role that embeds you with engineers. A builder role. Scratch and claw to find this, and once you have it, be wary of moving into a role without it unless you’re doing so intentionally to round out other aspects of your product experience…

Rounding Out Your Product Experience. I’ve spent 22 years in the e-commerce space and been somewhat intentional in my path. I started as a software engineer at a startup that got squashed by the dot-com boom, moved into e-commerce and started to get some product and management experience at a mid-sized company, moved into a PM role at Microsoft, and levered that up to the GM-type role that started my 12-years at Amazon. At Amazon, I led organizations in retail customer experience/conversion, social, direct traffic/loyalty (AmazonSmile), devices (leading Alexa International), and finally in Operations where bits meet bytes.

When I talk to companies now, either about full-time exec roles or consulting work, there is no customer-facing aspect of e-commerce that I don’t have direct leadership experience in or at least strong working knowledge of. This is no accident. I have more inroads into a target company than someone who is typecast because they’ve spent 10-15 years working on the same thing. You can figure out what domain experience could make you more well-rounded and more valuable, and go get it.

Breaking Into an Industry. Targeting a specific industry and charting a path to break into it is a mature thing to optimize for. A different industry may be growing faster, align with your passions better, pay better, or serve other career goals. If you can’t join the top company in an industry right away, play the long game and join a tier-2 company in that industry, then gain the domain experience that you can use to ladder up to a tier-1 company next.

Product Wins. Banking a big product win feels great. What’s even better about a win you can put your name on is all the other opportunities it can open up for you. There’s a HUGE difference between saying “I worked on X” vs. saying “I created X from nothing” or, even better, “I came up with the idea for X, built out the team, launched it, scaled it, and had XX large impact for the company!”

Choosing your next job to optimize for a big product win is 100% valid, but tricky. Here, the advantage goes to smaller companies. At a very small startup you’ll have the ownership to lay claim to the win - if it happens - but there is inherent risk in the company itself and the scale of any win may not be that impressive to larger companies.

A medium-sized company can be a good place to bank product wins. They have the size and scale to provide some security and may have some name recognition. Just make sure that you are in a role that can create and lay claim to a win (e.g. Product Lead for X, PM owner for X). At a large company, you’re more likely to be layered and own a part of X, until you move to more senior roles and get a chance to lead/own a product.

Management Experience. Moving from an individual contributor (IC) PM at one company into a management role at another may seem like a great jump to make, but it’s a risky one. You have to learn how to operate at a new company, how your product works, and how to be a manager all at the same time, while earning trust with your team and figuring out how to hire.

You want to have some amount of stretch in any new role, but too much increases the risk that you’re not successful and have to bounce out quickly. Large companies may offer developmental support for new managers. At small companies it’s sink or swim.

Team Size. If you already manage PM’s, then it’s valid to want to manage the same number or more PM’s at your next role, and to try to level up your team size. Smaller, well-funded companies can grow quickly, and give the opportunity to manage more people even if you don’t start with many or any. At large companies, teams don’t always grow rapidly, but if you’re successful you’ll get the opportunity to take on additional scope and grow your team or org size that way. Team size shouldn’t be the #1 thing you optimize for, but it may be #2 or #3, or serve as a tiebreaker.

Compensation. This is on everyone’s list. It makes a good tiebreaker, but hopefully isn’t the thing you optimize for above all else. Large, public companies will always offer more near-term comp - useful when you want to buy cars, get a mortgage, or take vacations now. A small percentage of startups will make you f-you money over the long term, a meaningful percentage will net out even or significantly positive over the long term, and a similar percentage will leave you out of the money with options that are worth nothing. Is it more important to take nice vacations, or maybe buy a vacation house?

Good Boss or Team. If you’ve never worked with your prospective boss, you don’t really have any way to know how good they actually are. It’s a crapshoot. If you have, don’t bank on working for them long-term. They may leave the company or change roles, or you might get layered under someone else. Working for someone you know and respect and admire is a plus but be wary of optimizing for it alone.

More Senior Title. This is one of the worst things to optimize for in a job change, but also one of the most frequent. Don’t make it your #1.

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3. Ask yourself, “How could this job change turn out to be wrong?”

As you walk down the path with one or more companies, they’re selling you, and you’re drinking the Kool-Aid. It’s fun to dream about dominating an industry, running a big team, and having options worth millions. Pause. Reset. Ask yourself, “How could this job change turn out to be the wrong one?” Write down a list of things that, if they turned out to be true, could make this the wrong choice. For some, you have no way to know, but for many, you can do research or ask questions of your prospective new boss now to de-risk them. Here are a few.

You Don’t Have Access to Engineers. To be a great product manager you need to ship, learn, and repeat many times. If you don’t have consistent access to engineers, you can’t ship and learn. Ask how engineers are allocated on your new team and how many will be dedicated to the product area you own. Answers: “None yet, but …” = red flag. “1-2” = red flag as you’ll be under-utilized, and your impact will be limited. “X on the team, shared by you and 2 other product managers” = yellow flag as your projects might be lower priority and keep getting bumped. “2 butts in seat, with 2 open headcount” = yellow flag as those heads may disappear. “4+ butts in seats dedicated to the product you won” = green flag.

The Role is Program Management, not Product Management. Many companies and hiring manager don’t know the difference. Product is the "what” and the “why”. Program is the “how” and the “when”. Product builds. Program runs and keeps multiple teams connected. Product manager is a sexier title and at companies that have both role types, tends to pay better. Hiring managers have an incentive to call a role product manager because that title is more attractive to candidates, especially those in program who would love to switch to product. Unless you’re intentionally trying to gain program management experience, do everything possible to ensure your shiny new product management role isn’t really program. Scrutinize the list of job responsibilities. If the role entails a lot of glue connecting different teams, is heavily focused on repetitive processes (status reports, sync meetings, running sprints), or doesn’t have access to engineers (i.e. builders), then it’s probably program.

You Don’t Actually Get to Manage PM’s. You’re an IC at your current company and been promised the opportunity to lead other PM’s at the new company. Ask how many PM’s will report to you on day one. Answers: “None…” = red flag. “None, but the role has open headcount” = yellow flag. “1” = yellow flag because any type of re-org could leave you with none. “2+” = green flag.

Your Team is Smaller than Promised. You’re a PM manager who’s been promised a team of X size. Ask how many butts in seats (BIS) are there now. Answers: “None” = bright red flag. “<50% of X” = red flag. “50%-80% of X” = yellow flag. “80%+ of X” = green flag.

You Don’t Get to Work for that Specific Boss. Your great, former boss at company X recruited you to new company Y, then recruited you. What happens if that boss leaves the new company three months after you join? If that would suck, then maybe it’s the wrong move. Don’t let your decision be guided by or your success depend on riding a specific person’s coattails. It should meet your other criteria and that’s just a perk. If you get a year working for that great boss at the new company, consider yourself lucky.

You Don’t Get to Own that Special Project. You’ve been told you’ll be the lead for a cool project at the new company. It’s going to be your big product win. Ask how committed the company is to that initiative and listen for signs of its importance (e.g. “X engineers moved onto it”, “related to one of the companies top 3 priorities this year”). If you’re not convinced, be aware that it might get cut or deprioritized. Ask if you will be the sole product owner. If the answer indicates that other PM’s are working on the project, then you’re not the owner. Ask if you may end up being layered under a more senior PM or manager? A firm, “No” means that’s unlikely to happen in the next year, giving you time to prove yourself and earn the role. Anything less means you may not get the chance.

Your New Company Gets Squashed. I was a software engineer back in 2000 and saw the entire dot-com industry get squashed. There was no avoiding it. Today, tech is too big to get squashed as a whole, but big companies are freezing hiring, medium companies are doing layoffs, and there’s going to be a steady drumbeat of down rounds, acqui-hires, and companies closing up shop over the summer and fall. For startups, ask your prospective boss how much runway the company has and then divide that in half, because their current calculation is based on positive revenue growth which may not happen. Ask yourself, “If this company has to layoff 25% of staff next month, would I be one of the first to go?” For big companies, get the offer in writing and signed. Don’t tell your colleagues or your boss about the new job based on an agreed to verbal offer.

Your Comp Doesn’t Grow as Promised. Make the decision based on the comp in the offer letter, without giving much weight to bonus plans based on company goals or targets. They’ll tell you that X%+ of the bonus has been paid out in each of the last four years. It probably won’t this year. They’ll tell you that your comp is likely to go up and hit your target range next year. Don’t bank on it. Try to negotiate for it now because your leverage disappears once you join.

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You need to fill in the blanks for other reasons the job change might turn out to be wrong. Do the work, then ask the hard questions. Weigh the risks and either pass or take the new job with open eyes.

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