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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

Sun Ho, Founder of LittleLives Inc



Sun Ho has an edtech business, LittleLives. She’s helping turn complex school operations into simple and enjoyable processes.

What’s your story?
I’m just a small town girl who won’t stop believing.
Someone recently told me that the curious little 10-year-old girl in me is still shining through with excitement for the world today. Although, now, instead of being curious about how things work, I am interested in how we can solve real world problems. Today, I get to learn and build everyday on our dream to turn complex school operations into simple and enjoyable processes.

What excites you most about your industry?
Have you been to a preschool lately? In our day-to-day, we get to hear the wonderful laughter of children. We see the innocent smiles of our little ones, who learn as they play. We meet the tirelessly loving educators, leaders and parents who give their best. These are the people we serve everyday at LittleLives. It excites us greatly to be in an industry that meaningfully impacts the future of our world. When we see a new feature we have implemented in our system helping to shave off minutes or hours of administrative work for schools (and put a smile on many faces), it is deeply satisfying.

What’s your connection to Asia?
LittleLives started in Singapore. We have since expanded to multiple cities in Malaysia, Vietnam, Cambodia and China. Everywhere we go, we gain unique insights about different cultures. One thing that remains unchanged around the world is the passion to improve education. This includes the desire to refine school processes too. I absolutely love the people I work with, in schools and in my own team overseas. They have taught me so much about their cultures and countries.

Favourite city in Asia for business and why?
It is so hard to choose one. We love Kuala Lumpur, Penang, Ho Chi Minh, Hanoi, Beijing and pretty much every city we have visited. Setting up in multiple Asian cities has really become faster and more transparent than ever before. What a time to be alive and working on a startup, and even more so for a young woman in Asia.

What’s the best piece of advice you ever received?
Be true to yourself.

As a woman and as the founder of a tech startup, I have heard the many ways in which people express their surprise that I do not fit into – for lack of a better word – the norm. I am my own mix of feminine and geeky. I have a computer science background that I am passionate about and, at the same time, I love fun aesthetics and product development. Technology is an industry in which venture capitalists traditionally favour white, male founders as the stats show a concentration of success in this small demographic. Despite this, I have found that the people around me will respect me for being me because I let my personality and passion take the stage.

Who inspires you?
Beth Fredericks, the Executive Director at Wheelock College. She is a wonderful educator, leader and orator. At 67, she is as active as any young teacher and as wise as the oldest, most experienced professor. She has inspired so many early childhood educators with her stories, her teaching and above all, her warmth and delightful personality. She has contributed so much to the early childhood field here in Asia, and all over the world, over the span of her illustrious career. Her charm and kind heart makes her one of the most sought-after collaborators in our industry today. Yet, she remains humble, approachable and personable. Her enthusiasm for education and children, coupled with her infectious humour, are what I aspire to.

What have you just learnt recently that blew you away?
What continues to blow me away every time I witness it, is incredible potential that can be unlocked when a great team comes together. When you put together bright, experienced, communicative and open-minded people in a team, miracles can happen.

Creative ideas that were recently put forth in a small ad-hoc project team are now being turned into a new product that LittleLives will soon offer. When we first began discussions, we had no idea where they would take us; the only thing we knew definitively was that we wanted to help educators gain better access to resources to help them in their everyday classroom. It all fell into place when our team started brainstorming ideas that were based on the problems we knew were present in early childhood education.

Now, we have the trial version of a new module, LittleAcademy, and I am in awe of how all of this came together. I would like to quote Margaret Mead here, “Never doubt that a small group of thoughtful, committed citizens can change the world; indeed, it is the only thing that ever has.”

If you had your time again, what would you do differently?
To be honest, I would not change a thing. We made so many mistakes when we started this journey, but the lessons we learnt from our failures are what make us stronger today.

On a related note, there is this beautiful quote from Batman Begins:
Thomas Wayne asked, “Why do we fall, Bruce? So we can learn to pick ourselves up.”

How do you unwind?
It is important for us to allow our body, mind and soul to unwind and recharge. Badminton is my go-to exercise. I play twice weekly to keep fit and nimble. Recently I have picked up Yoga Nidra with an excellent instructor who has opened my eyes to all the good that meditation does for our minds.

Beyond this, I find that spending time with my loved ones, friends and teammates helps me feel grounded and loved.

Favourite Asian destination for relaxation? Why?
I travelled to China twice last year and truly fell in love with the country. It provides such a rich variety of experiences, from culture and art, to commerce and tech. I was in a constant state of amazement. It is a fast advancing nation that I really enjoy my time in, both learning and relaxing with the people I meet.

Everyone in business should read this book:
High Output Management by Andrew Grove, late CEO and Chairman of Intel. This is a book written in the 90s, but its ideas are still very much applicable to businesses today.

Andy lays out what you need to do to successfully manage your business in simple and concise terms. This does not mean that it is easy to grow as successfully as Intel did, but the book shows us that the path to greatness is apparent. What I personally love about this book is that it presents its ideas both logically and emotionally without judgement.

On the issue of an underperforming teammate, Andy offers a very simple explanation:
“When a person is not doing his job, there can only be two reasons for it. The person either can’t do it or won’t do it; he is either not capable or not motivated.”

And as a manager, all you can do is to train and motivate.

This is an excellent review of the book by Ben Horowitz of Andreessen Horowitz:
I highly recommend this book to all entrepreneurs.

Shameless plug for your business:
LittleLives is a leading preschool edtech company with a strong presence in over 700 schools in Singapore, 20 in Vietnam, 130 in China and 100 in Malaysia. LittleLives develops and provides applications that allow preschools to record children’s administrative records digitally, from attendance-taking to portfolio management. In addition to reducing the hassle of physical filing and documentation, the LittleLives system allows parents to keep track of the progress of their children’s learning at school through LittleLives parents’ app.

As an edtech company, LittleLives does more than facilitate day-to-day school operations. In 2017, LittleLives hosted the first ever International Pre-school Conference in Kuala Lumpur, which was attended by educators representing 1200 preschools in the region. LittleLives has helped over 215,000 children, 430,000 parents and 23,000 teachers bring schools into the 21st century and we are hoping to continue empowering many more around the world.

Reach out to us if you are involved in education or entrepreneurship. We’re always happy to chat!

How can people connect with you?
Just drop me an email at [email protected].

Twitter handle?
With so much to say, 140 characters is not enough. Hence, it is best to follow us on Facebook (, Instagram (littlelives_inc), YouTube (, and check out our LittleLives Blog ( to get to know us better!

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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Women on Top in Tech – Daphne Ng, CEO of JEDTrade



(Women on Top in Tech is a series about Women Founders, CEOs, and Leaders in technology. It aims to amplify and bring to the fore diversity in leadership in technology.)

Daphne Ng is the CEO of JEDTrade, a blockchain technology company focused on trade, supply chain, and financial inclusion projects in ASEAN. She is also the Scretary-General at ACCESS and Exco. of Singapore Fintech Association

What makes you do what you do?
I was introduced to blockchain technology in 2016 after I left my corporate banking career after 10 years. It was my mentor who first got me interested in this technology, which I then went on to delve further into, on its potential applications in the lending and trade finance space – domains where I came from.

How did you rise in the industry you are in?
Being in the space for 2 years and actively involved in the ecosystem, I was able to bring on the projects, network and a good degree of thought leadership in this vertical. Early on in the startup journey, our team faced many challenges. And to me, the key to rising above failures are two essential factors – resilience and support. While resilience is innate, I received a lot of help be it in terms of connections or advice. ‘Nobody succeeds without help’ rings very true for me.

Why did you take on this role/start this startup especially since this is perhaps a stretch or challenge for you (or viewed as one since you are not the usual leadership demographics)?
From the start, I focused on my domain expertise in trade finance and the application construct of how blockchain and DLT can be applied to these use cases. Also, my strategy from the start was to build a technology company made up of 80% tech and engineers, which is also our key competitive advantage today. At the end of the day, deliverables are about strategy and execution, which includes building and leading an ‘A’ team.

Do you have a mentor that you look up to in your industries or did you look for one or how did that work?
I have many mentors, which includes our company advisors (all of whom are well-known in this industry) and mostly informal mentors I meet via my connections, and on various occasions and circumstances. Creating opportunities also means putting myself in the right place, at the right time. And in my case, these were mostly organic and genuine friendships formed from the initial connection.

How did you make a match if you and how did you end up being mentored by him?
To me, a match in values is very important. It also takes humility to ask for help and be willing to listen to advice, which is important in order for mentorships to be successful – be it formal or informal.

Now as a leader how do you spot, develop, keep, grow and support your talent?
I love this question! I am passionate about building strong teams and helping my people grow. I abide by the 3Rs when identifying talents: resourcefulness, resilience and right values. And then I invest in the ‘potential’ and this means giving them room to lead, make decisions and take risks.

Do you consciously or unconsciously support diversity and why?
My support of diverse talents, skillsets and characters can be seen in the make-up of our core team – all helming specific roles and each bringing their own value to the table. We need the sum of all parts to build a great company.

What is your take on what it takes to be a great leader in your industry and as a general rule of thumb?
Great leaders emerge in times of failures and challenges, never abandoning the team, and always putting the team’s interests before her own. And I consciously live by these mottos every day.

Advice for others?
My advice to other entrepreneurs: be resolute and dare to be different. If you are going to follow others, then you will end up on the same path as them. No right or wrong; but I would rather chart my own path. This June, we are officially launching our blockchain project, Jupiter Chain (, which have garnered much interest in the industry, even before we made it public. We believe this project is the epitome of marrying innovation with practical implementation, and we want to be the first to truly operationalize blockchain for our ecosystem projects in this region.

If you’d like to get in touch with Daphne Ng, please feel free to reach out to her on LinkedIn:

To learn more about JEDTrade, please click here.

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