Planning Your Career in Product – P3

Two hands shaking

This is the third chapter of how to plan your career as a product manager. The first chapter described the various product titles (here), the second was about whether product management is for you (see here) and today we’ll discuss what should be your considerations when you believe it’s time for you to upgrade yourself to the next step in the ladder.

Of course – the advice given to a junior product manager vs. an advice given to a veteran one can’t be the same. Therefore, the tips and considerations will be provided based on your current role.

Let’s dive into it

For a junior product manager who wants to become a senior one

Ok, so you’ve done your first steps as a product manager and you liked what you’ve seen (and experienced). That’s a great start.

Do you think you are ready to step up your game?

A reality check

  • Did you spend at least 18 months as a junior product manager?
  • Did you take at least 10 small features or 6 big ones from ideation to production? 
  • Has your level of self expression evolved to the point where your boss has a very few remarks on each of your specs/PRDs before the spec review?
  • Do you feel comfortable conducting spec reviews and working with the R&D and the other various stakeholders?


If the answer to one of the questions above is ‘no’ – then I wouldn’t rush to look for a promotion just yet. Take your time. There are advantages to being a junior, you know – people are expecting much less of you, and you can take things at your own pace (well… as long as you don’t exaggerate). You are also marked as someone who could use mentoring – which is good for you as well (personally, I think any level could use some mentoring, but for some reason – this is not the common practice). 

Bottom line – don’t focus on promotion just yet. Focus on honing your skills and get the maximum out of your mentorship. It’s uncertain whether mentorship will be available to you once you are promoted, and expectations would certainly be high.


Anyway – if you do feel that you meet all the criteria above then the next step would be to inform your boss that you are ready. Good bosses would probably be proactive if they believe you are ready, so if you haven’t received any hints from your boss towards your readiness from such a promotion then either they don’t believe you are ready, or they haven’t put much thought into this. By informing your boss you’ll see which one is it – and work with that.


From the organization perspective – promoting someone from being a junior product manager to a senior one is usually the easiest thing to do. No need to wait for new ‘vacancies’ or available roles. No one needs to leave their chair for you to get promoted. No org changes. Well, at least most of the time.

Your organization will need to allocate more budget, because your salary is going to be promoted together with the title. That’s the only downside from the organization’s perspective. If the budget is secured and if your boss believes you’re ready – it should be relatively easy for you to get the ‘senior’ title and be treated as one. Good luck!

For a senior product manager who wants to become a product leader

You’ve done some mileage as a senior product manager and you believe you are ready to become a product leader. Before we delve into the reality check – let me ask you – why do you want this? Which aspect of the product leadership you desire the most?

Is it the desire to lead and mentor new product managers? (e.g. – becoming a manager) OR is it the desire to have more impact?

I will provide my take on this question at the end of this section. In the meantime let’s proceed to the reality check:

Reality check

  • Have you spent at least 18 months as a senior product manager and accumulated a period of about 3 years as a product manager?
  • Have you taken countless features from ideation to production to the level where this procedure is ‘walk in the park’ for you?
  • Do you easily establish trust with the engineering team? Have you worked with more than one engineering team who can vouch for that?
  • Have you taken an active participation role in roadmap planning? Did you make a positive contribution in such a planning?
  • Do you feel comfortable meeting and interviewing customers or users? Are you making sure to do it often enough? Are you effective enough with collecting actionable feedback?
  • Do you feel comfortable deep diving into the data behind the dashboard? Do you often work and brainstorm with data analysts? Have you designed several dashboards yourself?
  • Have you experimented enough with setting KPIs? Do you feel that you know how to measure value and impact?


As you can see – this reality check is more complex and thorough than the junior’s one, and for a reason. Making progress towards product leadership is a serious move. I’ve seen many senior product managers who spent nearly a decade as senior product managers and still haven’t mastered all of the above.

If you answered ‘no’ to one or more questions above – I’d recommend holding your position until you master it. If your current workplace doesn’t provide you with the ability to evolve in one of the areas mentioned above – then switch a workplace. Promotion is not the solution for you yet, in my humble opinion, since mastering all the bullets mentioned above is required in order to be successful when you are finally promoted.

Yes, you can learn ‘on the job’ as well, but you’ll probably make plenty of mistakes – and since you’ll be playing the ‘impact’ game now – the damage of each mistake is gonna be bigger.

Therefore, stay a senior product manager until you master all of the above. It’s totally fine to switch roles and employers, and I actually recommend that you spend time in more than one environment.

One exception to what I wrote above is when an opportunity shows itself. For example – one of the product directors got fired and your company is looking for someone to replace him/her – you can offer yourself to this role, even if you still don’t check for all bullets. However, you still need to master most of them, or otherwise I’d sadly recommend passing on this opportunity. Again – the stakes are too high for risking your reputation.

Assuming opportunity hasn’t shown itself so far, but you believe the time has come – everything checks out and you are ready – it’s time to look around you. Can your current company accommodate a new product leader? This usually requires a vacancy in one of these roles or some sort of a mini reorg. Talk to your boss about your desire if you believe there is a chance that your company can make it work.

If you don’t see any creative options for a promotion within your company – then look outside. There are always several companies who are looking for product leaders. However, since you haven’t done it before – you’ll need to put on quite a show and be very persuasive as to why a company which doesn’t know you should give you, a senior PM, the opportunity to be a product leader. Don’t worry, though. If you do master the bullets I’ve raised before – it’s just a matter of time until the opportunity shows itself (either within your company or with a different one). One thing, though, and that’s going back to the ‘why’ you want it – if you read my first post about the various product titles – you noticed that being promoted to a product leader doesn’t necessarily mean you’ll be managing other PMs. For example, as a head of product, it might be a while before you’ll have other employees to manage. So – if that aspect is important for you – you might need to wait even longer for such an opportunity.

My advice to you – grab an opportunity when it’s available and you are ready, even if it doesn’t include managing people at day one. Managing people will happen eventually – I assure you. Don’t condition this.

For a director of product or head of product who wish to become a VP product or CPO

You know how to deliver products. You managed several product managers and maybe even product analysts and/or UX/UI designers. You led several quarterly plannings and dealt with roadmap planning. It’s time for you to lead the (product) ship. Congrats. Let’s do a reality check first, just to make sure, ok?

Reality check

  • Do you master the ‘hands on’ aspects of the job? Do you write great product specifications and master the product delivery process?
  • Do you know how to analyze and read the market trends and where it’s heading? Do you have any proof of that? (for example – designing a roadmap that delivers on its business goals)
  • Did you take an active role in shaping the main KPIs of the company, including the north star? Have these KPIs proven to be useful? (reflected well how the company is doing)
  • Did you manage more than 5 different PMs during your career? If asked – would they testify you were a good manager and mentor for them?
  • Do you radiate trust with all the internal stakeholders? Do they enjoy working with you? Are you doing well with the company’s internal politics?
  • Did you actively participate in any of the product strategy discussions? Do you know what the current product strategy is and why it’s designed to achieve? Do you agree with that? If not – do you know what needs to be changed?


Becoming a VP product or CPO is a huge responsibility. Your ability to create an impact is huge. You really don’t want to f%#$k this up. Therefore, if some of the questions above make you feel uncomfortable – maybe you are not ready yet and there are some gaps you need to fill.

Now, here is the thing – there are not a ton of openings for these types of roles. Companies usually prefer to grow someone from the inside, and even if not – there can be only one CPO in a company, and most likely the same applies for most VP product roles. I will therefore tell you this:

If an opportunity within your company shows itself, and you spent at least one year as a product leader – apply to it, even if you don’t check for all the boxes above. My main reasoning is that such opportunities are too rare to dismiss easily.

However, my recommendation only applies to an opportunity within your own company, where you already know the people, politics and domain – so your chances of success are higher.

Don’t look for an outside opportunity until you are ready according to the criteria above and feel ready.

Again – the chances of you making painful mistakes is much higher in this role, and you really don’t want to stain your reputation with such a big opportunity.


There is no playbook here as for how to nail such a job aside from doing a remarkable job as a product leader. Master your game. The right opportunity will follow. I’m 100% sure.


For a VP product or a CPO who wants to advance to the best next thing

Become an entrepreneur. Really. That’s my best advice.

Reality check

  • Do people call you crazy?
  • Are you ready for a high stakes game where reality is gonna be an endless roller coaster for the next several years?
  • Does your wife/husband support you?


If all check – good luck!


That wraps up the post for today.

If you found this post/series useful – let me know in the comments. If you think others can benefit from it – feel free to share it with them.


Thank you, and until next time 🙂

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