Unconventional advice for transitioning to Head of Product


From Product Manager to Product Leader

This is not going to be your typical ‘how-to’ article for moving up into a Product Leadership role. I’m not going to cover the things you normally hear, like advice telling you to be a better PM, to be a better leader, to think strategically, etc — because you already know that stuff. 

Rather what I am going to cover are the major differences I’ve regularly observed between being a Product Manager and moving into a Head of Product type role. I want to talk about all the skills which are unique to being a Product Leader which you generally wouldn’t get much exposure to as a Product Manager.

Don’t get me wrong, all the skills you are already honing as a Product Manager are great and valuable for being a Head of Product — so keep working on them — but I want to help bring light to potential blind-spots so that you can better roadmap your way towards that role.

A leader of leaders

Often people say, the number one thing is that you’ve got to grow your leadership skill, and although true, as a Product Manager you are already in a leadership position (at least in my opinion) which means that you are already miles ahead in this department.
In fact, in my experience, the best Heads of Product I’ve worked with haven’t always been better leaders than the Product Managers they lead but rather they are usually very seasoned Product Managers who have a wide toolkit. This presents a new challenge — as a Head of Product, how do you impart your experience and wide toolkit onto your team?

This is often a paradigm shift for people who move into the role. The role starts to shift away from hands-on craft and you start to have new challenges like, how do I coach my Product Managers? How do I build alignment? and cultivate the right product culture for the product teams to succeed?

Often in my experience, it’s these soft skills side of the role that people struggle with and less on the more hard skills side like how to manage a portfolio of products? or investment questions like how much do I put into each product versus how much do I set aside for more moonshot ideas?

So rather I want to focus on the former, those soft skills, and how to build them.


Coach your Product Managers (and their teams, and your colleagues…ok coach everyone)

One of the big ways in which the role shifts when you move into a Head of Product type role, is that you now have direct reports. This means not only the management overhead that comes with people management but also your responsibility to them as a manager, to mentor, coach, guide and grow them to be the best Product Managers they can be — and ultimately one day succeed you as Head of Product.

“Directors / heads of product should be judged by their weakest product manager. Their #1 responsibility is to coach them, and the rest of their team, to be more effective in their role.” — Marty Cagan

Coaching is a skill which most good Product Managers should already be honing, even though you don’t have any direct reports you should still be coaching your Product Team, peers and stakeholders on what good product practice looks like — if you are a Senior Product Manager you’ve likely taken on coaching your more junior counterparts.

However, this is usually only a small percentage of your time as a Product Manager. All that dramatically changes when you move into a Head of Product role — coaching your team of Product Managers starts to become one of your primary roles and for some this can be quite a shock.
There’s a lot to learn in this domain, but don’t worry you don’t need to be a professional coach level. I usually recommend checking out Coactive’s coaching toolkit, there’s lots of great resources in there as a starting point.


Since starting to write this, Marty Cagan, founder of SVPG, has been releasing a series of coaching Product Managers articles on his companies blog



Think big-big-picture

Now when I talk about thinking big picture, I break it down into both breadth and depth. In other words, I’m talking about how wide you think (10,000ft) as well as how far into the future you think (1 month vs 1 year vs 10 yearsor even 100 years!)

The best Heads of Product (and Product Managers) I’ve worked with are not only great at casting a wide net but also about considering the future — they aren’t fighting tomorrow’s battle they’re thinking about the next generation of leaders and trying to solve their problems. 

This is a core component to good strategic thinking, it’s about playing the long game — great leaders are focused on the marathon, not running the sprint. 

With this comes a particular way of viewing the world — take coaching your Product Managers for example; do I step in and help a junior Product Manager have a successful first launch, or do I let it be a failure so they can learn from the experience? 

Those running the sprint are more concerned with making sure their people don’t make mistakes, so they jump in and take over at the expense of them learning a valuable lesson. Those running a marathon will let them fail (as long as it wasn’t going to have a massive impact) so they can learn a valuable lesson and avoid such mistakes in the future.

This is often the paradox many product leaders face day-to-day — do I do A at the cost of B — unfortunately this is the job, and having a wide breadth and depth will help you consider all the parameters and help you make more informed decisions. 

What I’ve found is that, Heads of Product who struggle in this domain are often missing either breadth or depth — they either making decisions within their world and haven’t considered the wide organizations (too narrow), or they’re too tactical and aren’t looking far enough into the future to make the appropriate trade-offs (too shallow).

To help build breadth I often advise going broad when it comes to knowledge and competencies — who’d guess! — This means becoming more of a generalist. I talked about this shift in Product Management in my talk at Leading the Product in Sydney last year that we are moving away from narrowness towards breadth. 

So go learn about different parts of the business, even move into them if you can — if you’ve been a PM in the same team, the same company for a while it’s definitely time to move to a new team, a new product area or even a new organization. Perhaps even consider some adjacent domains to do a course in, UX or even an engineering one — I have a friend whose a Product Manager and he recently did a certification in AWS Cloud! 

Having more breadth of knowledge and skills has also been widely researched to increase problem-solving and abstract thinking skills.

As for depth, a good trick is to break your thinking into horizons. Consider horizon one as now — what is the impact not? What the most important thing to do now? — then look at the next horizon, what about next year? — and then again with 5 and 10 years. Build up this reflex and you’ll start to build thinking in these different horizons as a habit. 


Build the conditions for Product teams to succeed

One side to considering the bigger picture is the external functions — product strategy, A&M, etc — but another equally important side is looking internally. 

You play a critical role in enabling your product teams to succeed through determining vision, strategy, alignment, structure skill and investment mix. 

I was working with a newly appointed Head of Product the other week and she was really keen to help shift the way her teams work, but she could already sense the resistance — the organization had already undergone several restructures over the past couple of years and what she was sensing was likely a bad case of change-fatigue.

Although still super keen to get the most out of her product teams, she really had two options on the table:

  • Bet #1: Rip the band-aid off — It was completely within her authority to make the changes she wanted so despite the change-fatigue she could just go ahead and make them but risk adding to the fatigue and putting people offside and losing them within the first few weeks on the job. 
  • Bet #2: Take it slow — On the other hand she could take a much more iterative and evolutional approach. Things will go slowly and the benefits of the changes won’t be seen anytime soon but there would be a lower risk in regards to putting people offside.

The reality is there’s no right or wrong answer — it’s context dependent. In her situation, the level of change-fatigue led her to take option two but in other cases, it might make more sense to go with option one.

As I mentioned before these kinds of paradoxes are the day-to-day life of a Head of Product — do I take longer to keep morale up and retain people or do I go all-in and risk losing people?

Teams may not always appreciate or fully understand certain decisions you make as a Head of Product but it’s your job to help them see the larger picture and provide the rationale behind the decision.

Resources worth having a look at: 

Build a Product Culture

“Culture eats strategy for breakfast” is the famous quote from management guru Peter Drucker. And many of us have seen this play out on more than one occasion. I’ve watched brilliant Product Leaders, who are great visionaries, have an excellent strategy, failed to build the right culture and bring everyone else along on the journey which resulted in them failing to realize their vision.

This is therefore perhaps the most paramount part of your role as a Product Leader. And similarly, Building and maintaining culture will be perhaps the most difficult thing any leader will have to do.

Part of this equation is to help coach the right mindset and to help your Product Managers understand what great product practice is like. But equally, as a Head of Product your role is to also educate your peers, and even the CEO, to better understand what great looks like.

“The only thing of real importance that leaders do is to create and manage culture.” — Edgar H. Schein

I was once consulting at an organization (I won’t go into the details of what their product was exactly, as it’s not necessary) but they had a clear customer conversion problem on their app — hence me plus a few others coming in. Now when I say conversion, in this sense we were looking at those who download the app vs those who signed up (converted to a user).

So, we did what you would normally do, kicked off a 2-week discovery. Through our discovery, we became confident that the primary issue was trust. Many initially downloaded the app wanting to use it however very few actually signed up. The product required your credit card details for reasons I won’t go into, but the way the sign-up screen was being presented it did not look as you’d say, trustworthy

Now often trust is a perception thing, we will trust Apple a lot more than some garage startup, for many obvious reasons but also because of Apple’s brand, we know them, who we don’t know is Joe-Bloggs garage-app-adventures down the road.

There were a number of opportunities we identified to help turn this perception around, and many were ‘low-hanging-fruit’, small tactical issues with the app itself — things like the copy in the app. 

The copy at the time was very formal, corporate and had a cold-robotic-ness to it. Thus, one of the first things we wanted to do was to change the copy to be more warm, friendly, personal and geniune. For all those whoes changed copy before, technically it’s quite a straight forward thing once you nail down the appropriate wording. However, a week into this and I suddenly found myself being dragged into a number of meetings with the GM of Marketing. It turned out that our new proposed copy went against their extremely outdated branding guidelines. 

In the end, we had to fight tooth-and-nail for these changes to go through, but it’s a clear example of how your organizations culture directly impacts the products and experiences your customers see.

So whether it’s your organization’s understanding of branding or whether your organization values output over outcomes and is stuck in what Melissa Perri would describe as ‘the build trap’, as a Head of Product you play a pivotal role in tackling these cultural issues. If you’re org values shipping features and not doing discovery then you need to help educate your peers about why that’s a bad idea. You need to help build a more product-friendly culture so that you’re teams are able to do what they do best and deliver amazing products. 


Being a Head of Product isn’t always the glory people often think it’s going to be. I often speak with Product Managers and they want to be promoted so that they can “finally have control over the decisions that are being made”. But the truth is that as a Head of Product you actually move further away from the decision making, from the day-to-day. You start to be higher level, focused on capability uplifting, coaching and culture. 

Often those Product Managers are in a situation where their culture isn’t product friendly. This ironically means that the person in the Head of Product role is likely not doing their job properly, because they really should be empowering their team and setting the conditions for them to succeed — that’s what the job is truly about. 




Anthony is a Product Leader who heads up a team of 20+ Product Managers, Agile Coaches and Designers who partner with clients on all thing’s product and technology. Anthony has done everything from early stage product discovery to pivoting products and even sunsetting them. He is often called in at the CPO/Head of Product level to help them with strategy, scaling and increasing their organization’s product maturity. His experience pans across many different industries and companies of all shapes and sizes – from start-ups to large corporates. He loves great coffee, a good laugh and building meaningful products.

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