Alex Cowan: An Interview About Redefining Preparation Of Tech Leaders For Successful Careers

By Amit Chowdhry • Feb 28, 2024

Alex Cowan has been working in the tech industry for 25 years, and he started exploring money-making opportunities with computers at the age of 19. With experience in new ventures, ‘intrapreneurial’ projects within established companies, and three successful exits as both founder and investor, Cowan has constantly sought ways to improve the field.

Currently, a professor at the prestigious Darden School of Business, Cowan is redefining the preparation of tech leaders for successful careers, with his approach gaining immense popularity and reaching over 500,000 practitioners worldwide. 

Alex Cowan’s Background

After asking Cowan about his background, he said:

“I grew up a small child in rural Massachusetts during what was effectively the ‘pre-Internet era’. It was a nice place, but by the end of high school, I was pretty antsy to see the wider world- so I moved to California for college.”

“That’s when things started to get weird. All of a sudden, I was in this choose your own adventure situation. I dropped out of college the first time right after my freshman year and started what’s now GovPlace, a consultancy that does digital work for the federal government.”

“After that, I went back to college, dropped out again, and then started and sold (and also not sold) a few more companies along the way. Once I got on the roller coaster of starting your own thing, it was hard to get off. More recently, I found a great off-ramp teaching at UVA Darden while still working with startups.”

Becoming An Author

What made you decide to become an author? Cowan shared:

“Mostly, it was the online courses I’ve been doing and that community’s interest in a book. I’m up to around 700,00 courses served. Believe me, no one is more surprised than I am- but, it turns out, if you have a clear outcome you want to get for your learners and you experiment enough, you can get to something that enrolls well.”

“Since the learners were asking, I figured, ‘Why not a book, too?.’ So far, so good: I’ve been really happy hearing about how readers are applying ‘Hypothesis-Driven Development’ and the other books in the Advanced PM Series.”

Idea For The Book

How did the idea for your book come together? Cowan explained:

“It came together in fits and starts, to be honest. Hypothesis-Driven Development is a way to approach product management, specifically with digital products. The basic idea is that your goal should be to minimize the cost of a successful product or feature by minimizing waste. That doesn’t mean making every single feature successful, but it does mean being ready to be wrong and testing your way to a reasonable conclusion about that- ‘do we continue with this or scrap it?.’” 

“Like a lot of instructors, I tried to do too much with the first version of the book. It was over 600 pages and I pretty much ignored early advice that it was too long. In retrospect, that was pretty dumb, but I think it’s important to reflect on those kinds of mistakes, forgive yourself, and get ready for what’s next. A lot of what’s hard about any consistent practice is being ready to invest the energy in making it work. Anyway, I did some early direct sales as a kind of test and did convince myself it was too long.”

“Fortunately, the book was already in two main parts, and editing it to the current, more compact version was relatively obvious. I wanted something that I could hand to any entrepreneur, any manager who wants to build a digital product and confidently say: “Read this, and you’ll understand how to do it,” I’m happy to say that’s where the book is now- it unpacks how to take a test-driven approach to creating new ideas, going from idea to design, design to code, code to deploy, and how to focus that whole cycle with analytics.”

“The other material I had in the original book I’ve been gradually reworking into stand-alone books, what’s now the ‘Advanced PM Series.’ I’ve been enjoying that a lot. Basically, those books are ‘deep dives’ about applying a test-driven approach to specific topics like digital infrastructure, cyber security, AI, and growth. I’ve had the chance to work with great partners on that material- Nir Eyal (author of Hooked) on growth hacking, Colin Zima (former CPO Looker/Google) on big data and AI, and Dave Mitchell, whose last startup I invested in, on cyber security.”

Favorite Memory

What has been Cowan’s favorite memory of putting the book together? Cowan reflected:

“This is kind of obscure and nerdy but as I was editing, I had a whole bunch of new citations I needed to write up. If you’ve ever done it, it is a pain, but it turned out to be one of those things ChatGPT does super well and I just remember thinking- ‘This is going to be so great. So much crummy grunt work that people had to do is just finished- they’ll never have to do it again.’”

Economics Of Decisions

In the book, there is an emphasis on the economics of decisions. Could you discuss this and the impact on product management? Cowan pointed out:

“Yes! As a manager, your job is mostly to decide things, and yet so much of what we do in product management is just on auto-pilot. If you’re in product, your job is to ‘innovate’ and so the natural tendency to just do stuff and produce output is incredibly wasteful.”

“Instead, it’s important to embrace all the messiness of what product management is, which is basically trying to engineer certain user behaviors on top of a digital platform. You’re never, ever going to be right 100% of the time. But, if you can batch the work of your team into explicitly testable chunks with a clear target outcome, you’re going to reduce waste and create more room for wins. Hypothesis-Driven Development is just a practical way to do that.”

Hypothesis-Driven Development

What led to your interest in Hypothesis-Driven Development? Cowan noted:

“I think most of what product managers need to be successful is already out there- they just need to connect with the right practice, try it out, and establish some consistency with the approaches they find work. So, I hate the idea of introducing new frameworks. I love the material we have on how to build great products- product design, design thinking, Lean Startup, even agile. Applied in the right way at the right time, they all work great.”

“But what I was finding with my advisees and my students was that it’s hard to reliably create that pairing of right tool, right time. In particular, it’s crucial that there’s some relatively immediate payoff, some kind of observability that the tool is helping- otherwise, why bother? What I did start to see was that no matter the topic, pushing on testability reliably got practitioners to a more disciplined execution. From there, I just kind of tested and revised the material to get to what’s now HDD. And I keep at it!”

JTBD Methodology In Business

Do you believe that the JTBD methodology would help many business owners/managers determine if there is a product-market fit before a full rollout of their ideas? Cowan replied:

“I do, 100%. It is the fastest, least expensive way to test whether there isn’t product-market fit, and that’s actually a super power. My favorite vignette on this is from my sometimes collaborator Laura Klein: Consider a job board for pets where pet owners can hire out their pets. Just a bad, crazy idea. You can go talk to pet owners, ask them the top five things they wish were easier or better about having a pet and you will never hear ‘finding them a good job.’”

“Now you can move on to your next idea, which is hopefully better. It’s not a sexy way of looking at things, but that’s the reality of the innovation business: you make money by having better processes to test ideas with a minimum of waste and a maximum of velocity. That’s what good venture investors do, it’s what good CEO’s do, and it’s what good product managers do. Zombie ideas that just aren’t going to get to product-market fit kill companies all the time.”

Challenges Faced

What challenges have you faced in writing the book, and what steps have you taken to overcome them? Cowan acknowledged:

“On the writing part specifically, it’s been a lot of work but not too challenging in the sense of problems with non-obvious solutions. I think part of that is that I have some great, complimentary talent I’ve worked with for years- designers, editors, that are always ready to ask me the hard questions and do beautiful work themselves.” 

Feedback Received

Could you discuss some of the feedback you have received in teaching these concepts on Coursera? Cowan cited:

“My favorite feedback is when I see the learners I’ve connected with on LinkedIn getting cool new jobs! Now, I don’t mean to suggest that the courses singularly did that for them, and, regardless, it’s ultimately something they did for themselves.”

“My second favorite feedback is really that the course helped them learn something in a substantial way. There is a lot of hype around product management right now- the idea that there’s some secret recipe that only certain people or certain companies know. I don’t think that’s true, but that’s a much harder message to sell- so when I hear, ‘I took a bunch of courses on Reforge with industry people, but I learned more from your courses,’ then I have to admit, I’m pretty pleased. Teaching is a job, and it’s hard to do well. I’m not the perfect teacher, not by a long shot, but I take that part of the job seriously.”

Main Takeaways

What are the main takeaways that you want readers to understand from the book? Cowan concluded:

“Just framing your ideas in testable terms will help you do better, more intentional work, and it will make you a better collaborator: If we do {x}, then {y} will happen. Give it a try!”

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