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Why Your Product Team Is Failing



I build teams that build products. It’s my thing that I do. Engineering, Design, Marketing, and Product Management. That’s what I did with the pretty-big Firefox team at Mozilla. That’s what I did as a consultant with tiny to medium-sized startups in Toronto. That’s what I’m doing now with the growing and amazing team at Hubba. I love it.

Are you in charge of a startup product team? Do you love it? Because, and I want to be honest here, a lot of the people I talk to who run product groups are not having a good time. They are not even having an okay time.

They are having a not okay time.

What It Feels Like

The hard thing about a busted product org is that the problem isn’t obvious. The engineers seem to know what they’re doing. The product managers have roadmaps. The designers are always busy and things look nice. But it just. doesn’t. work.

Your team seems to run fast, they ship a lot of code, but features take forever. You never feel like you know when something’s going to come out. When it does, it never looks like you thought it would. The engineers celebrate when they complete a heavy project, but the rest of the org doesn’t get why it ever mattered. People don’t respond to new features, and bugs in old features never get attention. Things break that we should have seen coming, and you have to drop everything to fix them. Which makes the other problems worse.

If you’re hyperventilating right now, I feel you. I’ve been where you are. I wrote this post for us.

Whose Fault Is It?

“Everyone’s fault. No one’s fault.” I think I’m supposed to say those things. That there are a hundred reasons for product teams to fail to execute well. I guess that’s probably true.

But in my own life almost every team I’ve seen struggle with this stuff fails for the same reason. There is one role in the product organization that we ask to be the integrators. The systematizers. And companies, especially startups, usually set them up to fail. We call those people Product Managers.

If your product managers aren’t on their game and well supported, you will have a bad time. Not because it’s always their fault. At all. But because when they’re in trouble, strength in other areas is unlikely to compensate.

How to Build Your Product Team

Any time I write a new job posting for a product manager, I brace for impact. Few people would apply to be heart surgeons, or forensic accountants, without any relevant experience. But lots of people apply to be product managers without experience. Everyone thinks they’d be good at product.

If none of your founders/executives have run product orgs before, it can be hard to know what to do. These candidates have so many amazing ideas. They have a lot of energy.

If you find yourself saying something like, “anyone can learn how to file bugs and run a standup, but what I like about this person is…” you’re about to make a mistake.

Hire Product Managers as Product Managers

There are lots of times in the growth of a startup where you should take a gamble on candidates with gumption, even if they don’t have the background. It’s a great strategy for building a more diverse team, and gives your senior folks mentorship opportunities. There are many times when it’s a wise and progressive call to make.

Your first few product management hires are just not one of those times. Your first PMs will set the tone for how your product team operates. And since few people have any kind of formal education in product management, your best indicator is significant, direct product management experience.

After those first few hires are in and operating well, go ahead and hire some trainees. Build a reputation for product excellence by training people up and setting the standard. Your people may get poached, but your inbound candidate pool will more than cover it.

That’s a high quality place to be, but not until you’ve locked on fundamentals.

Hire Product Managers, not Visionaries

Oh I know it’s unromantic. Great product needs vision. And good CEOs want partners in setting that vision. You want PMs who understand it and can bring their own light to it. I’ve heard all that. And it’s not wrong.

But the truth is that I need vision from my PMs about 5–10% of the time. I need brilliant, focused, measured execution from them all the time.

I didn’t say 0% vision, don’t straw-man me. Vision matters. But ideas are cheap and execution is very, very hard. Interview for the hard part. Hire for the hard part.

Product management is a real discipline, not a pretend catch-all title. That “anyone can learn” garbage up there undercuts the value of clear requirements, clean process, measurement, and accountability. Your product managers put the machine on rails and make sure it gets to its destination.

Vision is one of the tools they use to get there. The whole team benefits from clarity in the product’s narrative. You’ll meet candidates who blow you away with their list of ideas, prepared over the weekend looking at your product. It’s exciting.

But if they can’t tell you when a waterfall development process would be a better choice than scrum, or how they feel about personas as a user-empathy tool, or how they prefer to see new features instrumented, they aren’t your first product hire. Or at least, they wouldn’t be mine.

Hire Product Managers, not CEOs-of-the-Product

Poor Ben Horowitz. He said, “The product manager is the CEO of the product” and I suspect he’s regretted it ever since. His intention was noble enough — arguing for buck-stop accountability and whole-product view. But it has armed a generation of asshats with a terrible self-importance. He even wraps that post with a disclaimer these days.

Your product managers are not the CEO of anything. They can’t fire people who are hurting the business. They can’t sign partnership deals. They do not live the 500 daily struggles of trying to keep everything alive and growing. It’s facile to pretend that the analogy holds.

PMs are much more hub-of-the-wheel than root-of-the-tree or top-of-the-pyramid. They synthesize, they decide, and they orchestrate. As Andy Grove would say: Input, Process, Output. If you think of them as a CEO you’ll manage the good ones badly and keep the bad ones around too long.

Be curious about how they listen and seek counterpoint during the synthesis phase. Challenge them on how they make trade offs in the deciding and planning phase. Measure them based on their results in the orchestration and delivery phase.

(I’m sure someone will tell me that’s exactly what a CEO does. This is the internet after all. It’s still a broken and unhelpful metaphor.)

How To Know It’s Working

When you’ve got good product leadership the chaos starts to make sense. You ship fewer features, but they speak directly to customer needs. They come with instrumentation so that you can measure their impact. Great ideas get amplified, missed attempts are spotted and quickly culled.

When your product team is working, the product connects directly to the strategy of the business. You can see how the roadmap elements move the needles you care about. You can elevate the conversation from “Ship this feature by Friday,” to “How should we tailor our onboarding to maximize engagement for different kinds of users?” Your PMs start to surprise you with vision and creativity that is rooted in reality. It makes sense. It matters.

This rarely happens right away. In my experience, good PMs often start with the safe, obvious bits. It helps them get processes in place, and ensures that they put up some immediate wins to earn the respect of their engineers and the broader team. On that foundation, I expect to see them take broader autonomy and scope pretty quickly and make the product their own.

A product manager that’s still running someone else’s roadmap a year in is effectively a project manager. A product manager that throws the roadmap away on day 1 in favour of their new vision is very likely a liability.

What if it’s Too Late?

You’ve already hired them, haven’t you? The ideas people. The CEOs of the product. And maybe you’re reading this and it makes some sense to you but you don’t think your existing team can get there.

You might be right.

But let’s choose to believe in them. Most people can learn most things. And I’m a really big fan of treating people like adults. So talk with them about this stuff. Ask them what they think of it, and what supports they need. Ask them if they agree.

And they may not. And it may be that they are not going to work out in your organization. And that can be okay.

If your team does agree they need a change, they’ll still need support to make it real. And so my second piece of advice, worth whatever you paid for it, is to hire an experienced product leader to drive that cultural shift.

Most product leaders love building things, and this is a good meaty role for the right candidate. Give them the founder’s vision. Expect them to want to see pitch decks and understand the state of the business. Get them to meet your existing product folks to see the potential that’s waiting to be unlocked. You can do it.

Sorry not Sorry

If any of this stuck, I’ve made your job harder. You had such a huge candidate pool before! You could hire exciting people with great ideas! Now you have to go hunt, and you need them to have well developed operational chops. There are fewer of those. And they are more hotly contested by savvy organizations that know what they’re trying to build.

But I’m not sorry. They’re out there. They work hard, they rarely get the credit, and they deserve to be courted. It can be thankless to wrangle a team of engineers and designers week after week. Particularly when the output is “reliable, measured, upward progress” which is easy to take for granted. So if I drive up their market rate a bit, I’m not sorry at all.

Go find them. Add your vision to theirs and their system to yours. Make something amazing.


About the Author

This article was written by Johnathan Nightingale of the Co-Pour. The Co-Pour is dedicated to leadership lessons with relevant articles and insights on the subject. Johnathan is also the CPO @Hubba and editor of

Callum Connects

Jonathan Oh, CEO & Co-founder of Supplycart



Jonathan Oh’s enquiring mind and love for learning has led him on an entrepreneurial journey, with him starting Supplycart which helps businesses manage their offices better.

What’s your story?
I am a person that just can’t sit still. I was always intrigued by how the world spins and how people connect. Spending a lot of time outdoors, I had an affinity with exploring new paths, thus leading me to become a serial entrepreneur with experience in creating, operating and building new companies. I am a firm believer there is so much to learn in the world and I love talking to people about ideas, what they are passionate about and what drives them.
Starting off my career in the medical industry, I realised I had a flare to create something that mattered, something that impacted other people’s lives. After exiting my first company in 2014, I continued my journey with two other ventures with a purpose to look towards impacting businesses in the region together with like minded individuals, and here I am.

What excites you most about your industry?
Being able to part of the SME tech industry and seeing how technology is moving SMEs to go digital to improve workflows and efficiencies is an exciting space to be in. Users are consumers. More and more, they are familiarising themselves with using technology in their everyday lives. We foresee the SME space to be the next area where adopting new technology would become vital for any organisation to remain relevant. As I have dabbled in this industry for close to nine years now, I am really looking forward to working with more people in the business community to make a change.

What’s your connection to Asia?
Born in Malaysia, I had the opportunity to go abroad and I realised there was so much to do back home. Spending time in Melbourne, Australia for a couple of years and recently Silicon Valley, it has provided me with experiences and insights into the difference a multicultural community can make. It also made me aware that Asia is still a very culture driven economy, as each country has its unique differences. I believe that the time is right to be in Asia now. We are a growing economy and a lot of exciting stuff is happening in this region.

Favourite city in Asia for business and why?
Malaysia. I believe Malaysia is still a very attractive destination for business as it’s close to other neighbouring countries within the region and travelling between the countries is easy. There is also proper infrastructure in place, an affordable cost of living and a sizeable pool of talent. The government also has numerous initiatives for technology companies to apply for MSC status that permits companies to hire foreign companies without restrictions. Malaysia is the perfect launchpad to start growing businesses regionally. From a culture perspective, we are multicultural, which promotes diversity in business and language is never a barrier here.

What’s the best piece of advice you ever received?
“The difference between a businessman and an entrepreneur; one does a markup and the other creates value.”

Who inspires you?
I would say the people around me inspire me. I wouldn’t narrow it down to a particular person but lump it up with family, workmates, entrepreneurs and friends. From my eyes, everyone has a certain drive, a certain glow and strengths that sometimes they do not see, and that inspires me. I believe the journey to success is never alone, it’s with people.

What have you just learnt recently that blew you away?
Something recently that blew me away, made me realise, visually about how much time I have left. I was reading and stumbled upon the writer doing this. This might sound morbid but I drew a horizontal line and started plotting the year I was born all the way up to when I think I might go. It showed me that I have spent 25% of my life growing up, I am going to spend another 55% of my life working and the final 20%, maybe retirement. It got me remembering all the milestones I have achieved and to be thankful for and above all, how I want to spend the 55% of my life doing what matters the most.

If you had your time again, what would you do differently?
I believe that I am exactly where I need to be because of the experiences I have had before. Thank god for the journey so far. It has been filled with ups and downs, new experiences and people along the way these have moulded me. I guess a small thing, if I had my time again, would be to pick up playing a musical instrument which I think still possible now. You are never too old to learn anything.

How do you unwind?
Unwinding for me would be spending time with my family and my two little boys. The little ones are such a bundle of joy. Reminding myself to have balance in terms of not missing the early years with them. Other than that, having coffee with other entrepreneurs, sharing ideas and learning from them is also another way I unwind.

Favourite Asian destination for relaxation? Why?
A term I would use would be “cuti cuti Malaysia.” This means heading to a local destination for some R&R to save on the cost of going on overseas to travel. Top of my the list would be heading to a farm or the jungle with clear river waters and a waterfall all to myself. Staying the night, out in the open under the stars, with a campfire and heading back to nature. The other option would be taking a boat to one of the furthest islands in Malaysia, just before the border of Indonesia, to get away from civilization.

Everyone in business should read this book:
I would actually recommend two books that everyone in business in the early years should read. ‘Founder’s Dilemma’ and ‘Start with Why.’ After being in a couple of businesses and many mistakes later, I came to realise the importance of starting it right. Both these books address the whole mind-set on what founders need to have from selecting who is it we start a business with to why are we starting the business. The business foundation is built from the founders and moving forward everything is built from there. Sometimes we are so into the business that we forget we need to be on the business as well. I would have definitely avoided a couple of bumps if I came across these much earlier on.

Shameless plug for your business:
Manage your office better, that’s our motto. We are always on the lookout to work with organisations, suppliers and partners in this field for partnerships and collaborations.
Supplycart is a B2B procurement platform addressing a need for a change in the way companies manage their office supplies, products and services. We enable suppliers and companies to adopt digital technology when selling and procuring for their business, resulting in a more efficient and productive workforce.
Supplycart provides an easy to use, convenient platform that streamlines the whole procurement process by allowing users to quickly order and reorder, receive instant quotations, obtain quick approvals from necessary approvers and fulfilment items are coordinated/planned to ensure a timely a speedy delivery.
Businesses can now focus on the more important matters in growing and sustaining their business while leaving managing the office to Supplycart. Our vision is to be the number 1 office platform for businesses across South East Asia. “Your office will never be the same again.”

How can people connect with you?
e : [email protected]
w :

This interview is part of the ‘Callum Connect’ series of more than 500 interviews

Callum Laing is an entrepreneur and investor based in Singapore. He has previously started, built and sold half a dozen businesses and is now a Partner at Unity-Group Private Equity and Co-Founder of The Marketing Group PLC. He is the author two best selling books ‘Progressive Partnerships’ and ‘Agglomerate’.

Connect with Callum here:
Download free copies of his books here:

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Callum Connects

Trung Nguyen, Founder & Managing Director of Advertising Vietnam



Having initial success with his first start up in the ad industry, Trung Nguyen went on to start other ventures in the ad world in Vietnam. He now has the largest agency community in Vietnam.

What’s your story?
Three years ago I got my first job in the advertising industry. I worked for a local agency in town, and I fell in love with the creative industry. In June 2015, I founded Agency Life Community in Vietnam. It quickly became the most engaging community in the ad industry. The main content focuses on entertainment. After six months we had over 30,000 organic followers, now we have 120,000 followers.

Because the industry had been good to me, I decided I had to something for the industry to help the industry be better. So, I opened – a creative industry ad site which keeps advertising informative, creative and inspiring.

After more than a year in the ads industry in Vietnam, I figured the industry needed a better solution for the recruitment of good staff. Given I own the largest advertising community platform, why don’t I utilise Agency Life to help connect talent with ad agencies. So, I founded job site, AdJob.Asia in January 2017.

What excites you most about your industry?
The ad industry is a creative one with very passionate people who are always challenging themselves. The exciting part for creatives, in the morning they might be working on a baby brand and in the afternoon they are answering a beer brief. There is so much diversity. Every day is the new journey.

What’s your connection to Asia?
I am Vietnamese.

Favourite city in Asia for business and why?
Thailand. The Thais are the kings of the creative industry in SEA. Thai ads are very smart and creative.

What’s the best piece of advice you ever received?
Do what you love.

Who inspires you?
My friend, mentor and partner Mr Nghi Nguyen, founder of We started our businesses at a similar time. He doesn’t see us as a competitor but rather, he believes that we share the same passion and we are working to provide better knowledge for the ad community.
Mr Nghi also guided me a lot when I first opened the business. I am inspired by his vision to make our marketing industry better.

What have you just learnt recently that blew you away?
Our business is a startup company and as a founder I do everything from operations, business development, planning and strategy. However, this is not the good way grow our business. You have to share the workload – find a co-founder or hire a great employee to help share the workload. “If you want to go fast, go alone. If you want to go far, go together.”

If you had your time again, what would you do differently?
Quit my full time job sooner.
During the first year of running my business, I was still working as an ad manager for an agency. However I lacked focus at work due to the overload of work and it affected the company I used to work for. I strongly recommend people who have an idea to start their own business, quit their job early on and focus 100% on it from the get go!

How do you unwind?
Play with my cat.

Favourite Asian destination for relaxation? Why?
I love to travel throughout all of Asia. I enjoy new places and meeting new people.

Everyone in business should read this book:
The Carpenter: A story about the greatest success strategies of all.

Shameless plug for your business: is a site where you can quickly update yourself on the advertising news in Vietnam. We have 15,000 unique monthly readers who are professional people in the advertising and communications industries.

The Agency Life, is largest agency community in Vietnam. This is the right place for ad agencies to share their creative work.

AdJob.Asia now has more than 160 agencies in Vietnam who use our services. We are a leading recruitment service for the advertising industry in Vietnam.

How can people connect with you?
You can connect with me:
Email: [email protected]

This interview is part of the ‘Callum Connect’ series of more than 500 interviews

Callum Laing is an entrepreneur and investor based in Singapore. He has previously started, built and sold half a dozen businesses and is now a Partner at Unity-Group Private Equity and Co-Founder of The Marketing Group PLC. He is the author two best selling books ‘Progressive Partnerships’ and ‘Agglomerate’.

Connect with Callum here:
Download free copies of his books here:

Continue Reading