Find a Great Product Mentor

Since I started my product career more than 20 years ago, I’ve been blessed to have great product mentors each step along the way. When I joined eBay in 2001, I was hired by Marty Cagan — now widely recognized as one of the founders of modern product management — and worked alongside Sr. PMs who have gone on to be highly successful entrepreneurs, CEOs, VCs, and thought leaders in the field. At Opower, I was advised by Gokul Rajaram and behavioral science experts like Robert Cialdini. Whether through smart decisions or good fortune, I can say with certainty that I would not be a successful CPO today without the lessons learned from experts such as these along the way.

Why a great product mentor is so valuable

A product mentor can be valuable both for the PM being coached and for the company that he/she works for.

For the employer, a product management mentor/coach can help to grow individuals and in turn the product and the business, but, most importantly, avoid costly mistakes or missed opportunities.

• Product management is an incredibly high-leverage function in a software company, even more so as seniority increases. In a product-led company, sales sells what product builds, marketing tells the story of what product builds, engineering creates what product management envisions.
• The cost of avoidable mistakes in product management can be massive. Not only because of the value of engineering time (often the critical constraint), but because of the high opportunity cost of having them not working on the most important problem.
• Consider that in the earlier stages, the company (or business line) is the product. Asking an inexperienced product manager/leader to figure it out on their own means “learning the hard way” with the entire business on the line.
• Unlike sales positions that are more plug-and-play and can be replaced with another gun for hire, a company usually needs to commit longer-term to a product manager/leader. Therefore, investing in those individuals is critical.

Of course, a mentor is also directly valuable to the product leader/manager.

• Product management is a notoriously difficult and ambiguous role (insufficient development capacity, responsibility without authority, etc.). Seeing how the role has been performed in other environments provides important context and perspective.
• There’s a lot of talk these days about the virtues of failing fast. But the fastest way (and least harmful way) to “fail fast” is to learn from someone else’s missteps and avoid repeating them yourself. A good mentor will share what worked and didn’t and accelerate your development.
• Product management is often thinking one or two years ahead, so you will encounter challenges (scale, competitive threats, etc.) that other functional groups in the organization haven’t yet considered, which amplifies the importance of getting guidance from outside the company, and from someone with experience handling those new challenges.
• Consider that just to maintain existing responsibilities at a startup, a person needs to grow at the same speed as the company (which could be 2x more year-over-year). Very real time constraints make formal training programs impractical, but 1:1 coaching can maximize impact without distracting from immediate priorities.
• Having access to someone at a later stage in their career provides clarity about the career path; simply seeing how someone more senior than you thinks, what questions they ask, how they frame decisions, etc. can be invaluable as you develop your career.

All the top Silicon Valley investors understand the criticality of the role of product management despite its ambiguity and varied definition across companies. Almost all the VCs and PE firms I speak with are desperately looking for ways to infuse expertise into their portfolio companies and are very supportive of efforts — both at the individual and institutional level — to bring external product expertise into their portfolio companies. Where they (and their CEOs struggle) is how to find it.

3 Things to Look for in a Product Mentor

The best way to ensure quality coaching and advice is by properly vetting the person you are working with in the first place. There are three attributes of strong product mentor:

1. They have the experience you are lacking because they are farther along in their product career or have already faced the challenges you are facing.
2. They have gone through the necessary diligence to convert their product management experience into true expertise.
3. They have the skill sets of a strong mentor, not just as a strong product manager/leader.

Attribute 1: More product management experience

It’s somewhat obvious, but a product mentor should have experience to draw upon that you wish you had but don’t. Without that additional experience there’s no particular reason the mentor would be able to provide you with something you couldn’t provide yourself.

One mistake many people make when looking for a mentor is that they value years of experience too greatly and don’t pay enough attention to the relevance of that experience. Fifteen extra years of experience isn’t useful if it doesn’t apply to the challenges you are facing now or will be facing soon. Here are a few examples why.

• Tools available to product management now are vastly different than they were 10–20 years ago, so experience working without modern software tools is no longer relevant.
• Company business models and fundraising strategy have shifted dramatically in that same time period.
• The best practices that apply to enterprise may not be appropriate for product managers working on a consumer product.

Pay close attention to the type of experience that a mentor has and how closely it maps to your specific needs. Key questions to ask when evaluating a prospective mentor’s experience:

• What would you say is the most relevant experience in your background to the challenges you expect to work with me on here and now?
• What are some examples of recommendations you would have made 5–10 years ago that you would no longer make today as product management has evolved?

Attribute 2: Expertise that stems from their experience

The words ‘experience’ and ‘expertise’ are sometimes used interchangeably, but they are not the same at all. Experience is in essence of bunch of data points, but expertise represents applicable insights drawn from that data points. To demonstrate real expertise, mentors should have developed frameworks, methodologies, or some other rubric that you can use to make better decisions yourself.

2a: Frameworks

Seek a mentor or coach who has established frameworks for product decisions. Ask to see those frameworks. They should be enlightening, novel and applicable to your product, your team, your goals, etc. and not break when tested by your unique circumstances. Having a framework is not just useful in its own right, but is also an indication that the mentor has abstracted the problems they’ve encountered and their solutions enough to figure out “the why”. That pattern matching is an essential skill that any mentor, but especially one focused on product management, needs in order to provide the best counsel to you.

Key questions to ask when evaluating a prospective mentor’s frameworks:

• What frameworks or strategies do you have for solving my top 3 items that keep me up at night (whatever they are)?
• How did you develop them? What experiences led you to adopt these in particular?

If you’re unsure what’s meant by a “framework”, here are a few examples all applying to various concepts within product management and design:

• Kano Model for planning a product strategy based on competitive differentiation
• RICE Model for prioritization across long lists of product enhancements
• Fogg Behavior Model for identifying opportunities to drive behavior change
• Vision-Led Production Management for connecting the dots between product vision, strategy, KPIs and roadmap (this is something I co-developed with my advisory partner Rajesh Nerlikar)

2b. Toolkits and real-world examples

The addendum to a framework is an associated toolkit, making it more immediately actionable and providing a common language for you to communicate with your mentor. These could be canvases, templates, guides, processes, etc. for applying the framework in real life. For example, I have provided several VPs of Product Management with a framework for evaluating their product managers by establishing a set of expectations broken down by seniority level. The concept itself is helpful, but much more actionable is the actual master career ladder spreadsheet (generalized for SaaS companies) outlining the specific skills and levels, which can be used as a foundation for hiring, promotions, and career development discussions with individual product managers on the team.

Key questions to ask when evaluating a prospective mentor’s tool set:

• Is there something specific you have used to put that framework in place? Can you show it to me?
• Will you walk me through how we would use this for ongoing conversations about myself or my team?

2c. Adaptability

Product management best practices are not one-size-fits-all. The correct product management approach can depend on a broad set of factors about the individual being mentored, the product, its usage and so on. A few examples:

• A/B testing methodologies require sufficient customers and product usage.
• Sticky notes are great for in-person sessions but inappropriate when working with remote engineering teams.
• User research plans have to be altered when the intermediate “B” in a B2B2C business blocks access to end users.
• Limited roadmap commitments can’t be avoided if they are necessary tools for highly competitive enterprise sales.

This list could easily be hundreds of items long.

Either your mentor must have deep domain knowledge in your market or must be highly adaptable to help you think through how their “ideal” activities, organizational structure, hiring practices, prioritization methodologies, etc. must be altered to suit you and your situation.

Key questions to ask when assessing a prospective mentor’s ability to adapt:

• Can you explain a circumstance in which your default framework/tool didn’t apply to a mentee and you had to adapt it for the situation at hand?
• What are some characteristics of a product or company that would affect the ideal product management methodologies or processes?
• What are some of the details about me or my situation that would cause you to advise me differently than you’ve advised someone previously?

Attribute 3: Dedicated Teaching Mindset

The last essential element of a strong product mentor is exhibiting the passion and skill sets of a true coach vs. just being an older and more experienced you. A mentor’s job is not to solve the problems for you and tell you to “start doing this” or “stop doing that”. A product mentor should instead be helping you to get better at product management, providing you with new ways of thinking through problems and solutions, and establishing new skills you may not have been able to develop quickly otherwise.

3a. Honesty and integrity

This one should go without saying, but it doesn’t. Most people think of the obvious things, such as maintaining confidentiality or tracking time accurately (for paid mentors). But a great mentor won’t just cover the basics.

• He/she will consistently give you the brutally honest feedback you need and the “tough love” that others might shy away from.
• A good mentor will also let you know you’re doing something well already and hold back on attempting to “add value” when they have no value to add on a particular topic.
• The strongest mentors will dig deeper when they sense something is wrong (burnout, strained stakeholder relationships, etc.), urge the mentee to fix underlying issues, and offer help even if outside the bounds of the mentor relationship, as long as it’s always with the support of the mentee.

Simply put, a mentor should prioritize your growth and ultimate success above all else.

Questions to ask when evaluating a prospective mentor’s integrity:

• Have you ever intentionally ratcheted down your time with someone because you felt it was the right thing for them?
• How would you handle a situation where I felt I was thinking about a problem the right way, but you felt I was thinking about it the wrong way? What if I didn’t back down?
• If you are working with both our head of product and our CEO, and you feel like we are off track, what actions would you take?

3b. Passion

A great product mentor must be passionate about the engagement. They need to believe in your company, the value your product can bring to the market, and the potential of you as their mentee. If the mentor doesn’t believe he/she can positively influence you, your product, or your company, then they cannot possibly bring their A-game to every session. And, you should expect nothing less than their A-game every time, since it is coming at the cost of your time (and perhaps your budget).

• When I was mentoring PMs full time, I would often find myself waking up at 3am with ideas for their products and immediately take notes to share with them the next day.
• I would use their B2C product in my personal life to identify usability gaps that may not be apparent at first glance or out of context.
• I vetted recommendations through other product experts in my network to get their feedback when applicable.

Determine whether your mentor is going to bring that kind of energy to the engagement.

Questions to ask when evaluating a prospective mentor’s passion:

• What excites you about what I’m working on?
• How could our elevator pitch be improved to further explain the value?
• What milestones could we hit that would be equally aggressive and attainable?
• Would you be willing to refer us to an investor if we asked? Why or why not?
• Have you done any talks about product management? What were they about?
• What are you top resources for staying up to date on the latest in product management?

3c. Proactivity

One of the biggest obstacles to receiving good mentorship is not knowing the right questions to ask or having blind spots that neither party ever realizes are important to discuss. That’s why finding a mentor who won’t just wait for the phone to ring but will actively be thinking about how they can maximize their value is so important. A great mentor should be proactive by doing all of the following activities:

• Set a long-term mentorship roadmap and check in on progress with you regularly.
• Create a shared document with a repository of topics for future conversations, and depending on the type of relationship, bring their own backlog of ideas to the table for ongoing discussion.
• Ask you to show some them of the deliverables you’re working on so they can comment on points you may have not thought to ask about on your own.
• Think about your product, the challenges you’re facing, and working to solve them behind the scenes. (For example, when identified usability issues that could be easily addressed, I’ve provided unsolicited product tear-downs and sent those notes out as general recommendations.)
• Reach out when it’s been too long since the last call. And, between calls, share relevant articles, podcasts, books, conference talks, etc. that keep the momentum going.

Questions to ask when evaluating a prospective mentor’s level of proactivity:

• What kind of work do you typically do between calls with your mentees?
• What activities would you expect me to do between calls?
• What percent of the agenda is usually set by the person you’re mentoring vs. by you?
• What are the attributes of a good student or mentee, and how would you expect me to demonstrate those?
• How do you evaluate the success of a mentorship relationship?

Summary

A strong product mentor can be a true game-changer for careers and companies, as I know from personal experience having been both a mentee and mentor. But not all mentor relationships are set up for success; take the time to find the right product mentor for you by asking the right questions up front. Look for a combination of experience, expertise, and coaching mindset that will ensure you have the right fit with your mentor. Seek to work with them through tangible resources, such as frameworks and toolkits that ensure transferability of their expertise to you.

More

At Prodify, a boutique product advisory and mentorship practice I founded several years ago, we’ve strived to raise the bar on mentorship relationships because we’ve seen firsthand how effective it can be. We’re truly passionate about the art and science of product management and in helping founders, investors, and PMs realize their full potential. If you’re interested in learning more about individual product management coaching (at any level from CPO to APM), product advisory relationships, product management consulting, or anything in between, feel free to reach out and discuss at hello@prodify.group.