Vetting Your Employer After Receiving a PM Job Offer

Essay originally published on the Product Teacher blog on July 5, 2022.

I occasionally receive questions from product managers who feel regret a few months after accepting their job offer, as they find that the employer they’ve chosen is not a good fit for them.

The good news is that this problem is mostly preventable. We can reduce the risk of “role fit mismatch” by asking a set of thoughtful questions to vet the employer when we first receive the PM job offer.

I know that it’s not our first instinct to ask questions when we get the good news that we’ve received the offer. After all, receiving a product manager job offer is exciting for any candidate!

It’s hard not to celebrate and to sign immediately. However, that’s not where the process of due diligence should end.

By vetting your employer after receiving a PM job offer, you’ll gain more insight into the kind of organization that you’re joining, and you’re more likely overall to accept a role that you’re truly a good fit for, which then increases your future career velocity.

To help you succeed, I’ve created this guide to help you vet your employer after receiving a PM job offer. We’ll cover the value of vetting your future employer, which kinds of questions to ask, how to assess responses, and employer red flags to avoid.

Note that we’re going to keep compensation negotiations out of scope for this guide. The core focus here is to help product managers accept a role where they’ll enjoy making contributions over the next 2–3 years at minimum.

Let’s start first by discussing why hiring organizations are eager to answer your questions once you’ve received a PM job offer from them.

How Hiring Organizations Change After the Offer

Once a hiring organization has decided to provide an offer to a given candidate, its recruiting mindset shifts away from “determine the candidate’s suitability” to “convince the candidate to join.” It shifts away from risk minimization and moves towards trying to secure upside.

In other words, when a hiring manager decides that they want to bring a candidate onto their team, they strongly believe that this candidate solves their pain. Therefore, they no longer have reservations about the candidate.

But, the most valuable candidates are typically being courted by other organizations who also want to hire them. Strong PM candidates will typically have 2–5 active offers at once to choose from once they’ve completed their recruiting cycles.

That’s why once an organization provides a job offer to a given candidate, they actively work to convince their chosen candidate to accept the offer, since:

• Hiring managers are evaluated in part based on how successfully they grow their team
• A significant portion of recruiter compensation is only paid out when a candidate joins the organization
• Candidates who sign with competitors present a risk to the organization because they’ll strengthen that competitor

There’s no better time to ask our hardest set of due diligence questions to identify whether we’ll enjoy working in the role.

But why couldn’t we ask these hard questions earlier?

Here’s why: pre-offer, the hiring organization isn’t yet committed to hiring you. Imagine if they invested leadership bandwidth to answer questions from a candidate that they then later decide not to hire. This time would have essentially been wasted.

But post-offer, they’re committed to hiring you, and every hard question they answer increases the chances in their favor that you’ll join them rather than a competitor. So, answering hard questions about role fit post-offer is a good return on investment for employers.

We now know that the best time to ask hard questions about role fit is after you receive the PM job offer. But, what’s the value of vetting the employer upfront, rather than waiting until we learn from firsthand experience on the job?

The Value of Vetting Your Employer

By vetting your prospective employer upfront, you’ll gain key insight into the role before joining full-time, such as:

• Professional development
• Managerial support
• Working processes and culture
• Product org structure and influence
• Company stability

These key components can make or break your experience with the organization. We don’t want to commit years of our professional lives to organizations that we’re not aligned with, as that misalignment will cause burnout. Burnout reduces our ability to create positive impact for users, and it slows down our own careers.

But if understanding these components are so important, why don’t more PMs vet their prospective employers upfront?

One reason I hear from PMs is that they feel that they can’t ask hard questions to the employer because they don’t want their PM offer to be taken away from them.

That fear is understandable, but let’s reframe the situation differently.

If an employer retracts an offer as soon as you start asking them hard questions, then that’s a definite sign that you don’t want to work there.

An organization that is fragile, ego-driven, and toxic is no place for a talented product manager to go. On the other hand, an organization that demonstrates confident humility, growth mindsets, transparency, and self-awareness is a place where product managers can thrive.

At the end of the day, employment is a two-way street. You want to find a place where you’ll learn and grow and create value for at least 2 or 3 years on the job.

Having the courage to ask hard questions upfront will help you avoid accepting roles that you won’t enjoy. You don’t want to wind up in a position where you leave the role within 3–6 months, as you’ll burn bridges within the company, you’ll cause future employers to doubt your commitment, and you’ll have to restart the time-intensive PM recruiting process.

So, to reduce the chances of you signing onto a role where you’ll have role fit mismatch, you’ll want to conduct due diligence and ask particular kinds of PM fit questions to the hiring manager.

Vetting Questions to Ask for Product Managers

Generally, I’ve found that the following four components have created the most heartburn for product managers.

• Role expectations: what defines success for this role, and how does this role evolve over the coming months and quarters?
• Career expectations: what career trajectory can I expect within this organization as a product manager?
• Process expectations: what kinds of processes are encouraged, and what kinds of processes are discouraged?
• Strategic alignment: where is the company going, where is the product team going, and how does this role fit into the overarching strategy?

To address these areas, I’ll provide three questions you can ask for each area.

These questions are simply meant to help you jumpstart your own set of questions. Don’t feel obligated to ask every single one, and feel free to add more questions or to remove a suggested question. Don’t hesitate to use your own judgment!

To clarify, there’s no single “correct” answer to these questions that you’re looking for from the employer. Instead, your goal with these vetting questions is to determine whether you’ll resonate with the role and the organization.

Role expectations

Every company has different expectations for their product managers. Even within a product organization, different product leaders will have different expectations for different roles.

Here’s a solid question to ask to understand PM role expectations: “What does success look like for this role 3 months in? 6 months in? 1 year in?”

Essentially, you’re looking to understand the roadmap for the role, and what kinds of milestones you should expect to achieve.

You’ll learn whether your focus will be to launch new products or to scale existing products. You’ll identify whether you’ll be spending most of your time with design and engineering, or with customers and end users, or with business-side stakeholders.

On top of that, you’ll learn how well-defined the problem area is for this PM role, and you’ll learn how much latitude you have for defining the solution.

Another great question to ask the hiring manager is “What’s the largest challenge that this role will need to overcome in the first year?”

This particular question will help you understand where the friction is within the company. It also serves as a check to see whether the hiring manager actually knows why they want a PM.

In large non-tech companies or in early-stage startups, some hiring managers don’t know why they want a product manager. This lack of clarity creates deep misalignment, as success becomes a “moving target in the dark.”

On the other hand, if a hiring manager can clearly identify the core challenge at hand, you’re much more likely to stay aligned over the long term about what success looks like.

The third question to ask: “Which cross-functional stakeholders are most crucial to collaborate with for this role, and what should I keep in mind as I look to build rapport with them?”

This question identifies whether the hiring manager understands which cross-functional stakeholders are at play. A hiring manager who deeply understands cross-functional stakeholders will serve as your champion and advocate, whereas one who doesn’t understand stakeholders will likely be unable to help you excel.

Furthermore, this question helps you understand who within the org has the most influence and authority for your particular product. In turn, you’ll then be able to set realistic expectations for yourself in terms of who you’ll spend the most time with.

Some product managers want to spend more time with designers and engineers, rather than with customers and end users. Other product managers want the reverse.

Since there’s no universal answer for “how much time should a PM spend with different aspects of the business”, it’s crucial that we identify upfront whether we’re aligned with how this prospective employer wants to allocate our time.

To summarize, here are three questions you can ask to assess role expectations:

1. What does success look like for this role 3 months in? 6 months in? 1 year in?
2. What’s the largest challenge that this role will need to overcome in the first year?
3. Which cross-functional stakeholders are most crucial to collaborate with for this role, and what should I keep in mind as I look to build rapport with them?

Career expectations

While product managers are in charge of their own careers, it’s helpful to understand the default trajectory that the hiring manager has planned for this role. That way, you’ll better understand whether the trajectory is too fast, too slow, or a good fit for you.

One good question to ask is “what kinds of professional development opportunities and resources are available for this role?”

This question helps you understand whether most of your learning will be on-the-job, or whether the company plans to invest significant resources into upleveling its product talent outside of day-to-day experiences. Again, there’s no universally good answer here — it’s all about whether their philosophy around professional development lines up well with yours.

Another good question to ask is “what does the process for promotions look like, and can you share an example of a product manager who was recently promoted?”

This question helps you understand the company is actively planning to uplevel its product talent. Some organizations are focused more on pure execution rather than long-term talent development, and it’s important that you know upfront whether there are opportunities ahead for promotions and scope increases.

Yet another excellent question to ask the hiring manager is “what excites you to work here, and what do you expect in your future here?”

This question gives you a different lens into the company’s growth. By understanding your future manager’s motivations and desired personal trajectory, that helps you understand the pace that your manager might expect from you.

To summarize, here are three questions you can ask to assess career expectations:

1. What kinds of professional development opportunities and resources are available for this role?
2. What does the process for promotions look like, and can you share an example of a product manager who was recently promoted?
3. What excites you to work here, and what do you expect in your future here?

Process expectations

Product managers work in context, and they need to understand the current working processes within the organization. I frequently see that product managers might get frustrated with lack of process or frustrated with too much process, which is why it’s valuable to ask upfront to get a sense of what level of processes you’ll need to work with on the job.

One question you can ask is “tell me about an effective partnership between design, engineering, and product management within the company. What makes this partnership effective, in your eyes?”

The answer to this question will help you better understand whether the organization is engineering-driven, design-driven, or product-driven. None of the answers are wrong! You just want to understand what the interplay between product managers, designers, and engineers are.

It’ll also help you understand whether you’re working with engineers who are empowered to push back, ask questions, and make product recommendations, or whether you’re working with engineers who need significant guidance and top-down direction.

Another great question to ask the hiring manager is “tell me about an obstacle that you overcame in this workplace, how did you overcome this obstacle?”

This helps you understand the kinds of processes that you’ll be expected to model when it comes to negotiations, problem-solving, and conflict resolution.

Finally, consider asking the question “what kinds of traits or personalities typically do well within the organization?”

This question helps you understand whether they expect product managers to build full consensus before running forward, or whether they expect product managers to be the primary decision makers.

To summarize, here are three questions you can ask to assess process expectations:

1. Tell me about an effective partnership between design, engineering, and product management within the company. What makes this partnership effective, in your eyes?
2. Tell me about an obstacle that you overcame in this workplace, how did you overcome this obstacle?
3. What kinds of traits or personalities typically do well within the organization?

Strategic insight

Don’t forget to ask about the future of the company! After all, product managers are responsible for building towards that future state, so it’s crucial to understand where the company is going and to decide upfront whether you’re aligned with their direction.

A good question to ask the hiring manager is “where do you see the company headed in the next three years, and why?”

By asking this question, you learn not just what the company strategy is and how the role fits in, but also how transparent the org is and how much info leadership shares with product leaders. On top of that, you’ll also learn how much say product managers have in influencing the roadmap and the strategy.

Another good question to ask is “how does product leadership balance resources between external commitments, product strategy, and engineering strategy?”

You’ll want to determine whether the company is focused heavily on securing new customers and is more sales-oriented, or whether they have a specific direction they want the product to go from an internal strategy perspective.

You should also be interested in understanding how they balance between investing in technical foundations vs. creating new functionality.

Companies that invest heavily in technical foundations might have less short-term bandwidth but will have more long-term bandwidth, whereas companies that invest heavily in product functionality might have more short-term bandwidth but less long-term scalability.

There’s no right answer to this question! Rather, it’s all about understanding whether you resonate with their approach to product management.

Another solid question to ask is “how do investors influence the product roadmap?”

This question gives you two different kinds of insights. First, you’ll learn whether fundraising will unlock new initiatives to pursue and whether it will increase staffing for design and engineering, or whether fundraising is more about driving sales and marketing.

The second insight is that you’ll learn how product functionality fits in with fundraising. Specifically, you’ll learn how much say investors have in terms of company strategy and roadmap, and how product leaders balance between external pressures and internal conviction.

To summarize, here are three questions you can ask to assess strategic alignment:

1. Where do you see the company headed in the next three years, and why?
2. How does product leadership balance resources between external commitments, product strategy, and engineering strategy?
3. How do investors influence the product roadmap?

How to Evaluate Responses from Employers

As we ask these vetting questions, we want to identify the following attributes:

• Do these responses resonate with my values, needs, and goals?
• Is the employer self-aware and insightful?
• Does the employer have confident humility and transparency?
• Does the employer plan to address identified gaps?

To clarify, no employer will ever have 100% fit for all of your needs! The key is to prioritize the aspects that you care about the most.

If your overall sense is that you’ll thrive in the role and that you can overcome areas of mismatch, then you’re good to go.

On the other hand, if your overall sense is that there’s too much mismatch for you to feel good about your work, then you should consider other employers instead.

And remember, it’s possible to iterate towards PM fit in the future! Your upcoming role doesn’t need to be perfect, nor should it be perfect.

As long as you’re aware of potential challenges you might face in this role and you accept these challenges, then don’t be afraid to commit to this employer.

That said, while we’ve clarified that there are no right answers, there are some answers that are definitely wrong.

Let’s cover which red flags we should watch for when we ask these vetting questions to the hiring manager.

Universal Red Flags to Avoid for Product Managers

You’ll want to watch out for these red flags for any PM role:

• The hiring manager is unable to answer questions about the day-to-day of the role
• The hiring manager is unable to answer questions about cross-functional stakeholders
• The hiring manager is unable to answer questions about company strategy
• The hiring manager shares that the company has “no weaknesses”

These are red flags because they demonstrate a lack of understanding for the product management role. If you run into attributes like these, you can be sure that the PM role won’t have the support and resources required for sustained success. When this lack of clarity exists, it’s hard for the PM to advocate for initiatives, secure resources, or get promoted.

These red flags typically appear for a couple of reasons:

If you run into these red flags, you’ll usually be better off looking for a different employer, rather than attempting to “change the organization from the inside.” You’ll make more impact in the long run, and your career will be more enjoyable and fulfilling.

Closing Thoughts

Product managers can sometimes feel disillusioned or misaligned after a few months on the job, and the root cause is due to role fit mismatch.

Thankfully, we can identify potential role fit mismatch before signing the offer. To ensure that you find a career that’s valuable while also minimizing thrash to employers, ask these kinds of questions to the prospective employer:

By having the courage to conduct our due diligence before accepting the PM offer that we’ve received, we’ll set clearer expectations for ourselves on what kind of organization we might be joining, and we’re more likely to identify upfront whether we’ll enjoy the role.