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I’m a marketing director, not CTO, so take this with a grain of salt. But I believe leaders should be “good enough” in a wide array of disciplines. Certainly th

I’m a marketing director, not CTO, so take this with a grain of salt. But I believe leaders should be “good enough” in a wide array of disciplines. Certainly the disciplines involved in their department, but also, frankly, every aspect of the business. Meaning a CTO should also be good (not great) at sales, marketing, cash flow, customer service, user experience design, etc. Being well rounded means being able to garner the respect of not only the engineers but all stakeholders, from internal people to the customers to the general public, too. I’m certainly not arguing that a great engineer won’t make a great CTO. It should probably the area they’re strongest in. But if I had to pick between an amazing engineer who knows nothing about the rest of the business, or a reasonably knowledgeable CTO who is also reasonably knowledgeable on all other fronts, I’d pick the latter every time. No hesitation. There is a caveat to this, though. Being a generalist means recognizing that on any given topic, someone knows better than we do. So you have to be able to recognize that and defer to expertise, while also completing the picture by thinking about all the variables that lead to a business being successful. I’ve met plenty of engineers (and designers and copywriters, etc etc) who think everyone else’s roles are easily understood and accomplished. That’s fine if you’re a specialist. But a leader needs to understand the big picture, and no one is an expert in all areas. It’s just not possible, by my estimation.

spopejoy 4y ago
There's a huge difference between a Dropbox and an Uber here. Dropbox is a technology company. This is famously a place where deeply technical leaders can achieve competitive advantage. The whole company exists to support the tech, so if the tech fails, bad. Uber (and most startups really) don't do tech, they use tech to drive sales. Of course the tech is important but it's a solution not a driver. Here I agree that a "well-rounded" tech-average CTO can be advantageous. Tech strategy is where everything converges. If products literally live or die by it, you better have a crack technologist at the top.
- nickelcitymario 4y ago
  For clarification: Are you suggesting Dropbox’s leaders aren’t well rounded? Or that they are and that they also need to be stellar engineers? I think you make a great point either way. I’d elaborate on that and say a business leader needs to deeply understand the product they make/sell, so if your core product is tech, I agree and see your point. But I still think they need to be really good at all facets of the business. They still need to understand the market and how to promote and how to close sales. Those skills don’t really develop if the only thing you do is engineering. Take HubSpot’s CTO Dharmesh for example. Brilliant engineer! But he applies his curiosity to understanding people and markets and solving unsolved problems. He understands the whole business. He also understands his own shortcomings and surrounds himself with people with complementary skills, because he knows full well that engineering alone isn’t enough.
  - dshah 4y ago
    Thanks for the kind words. I don't consider myself a "brilliant" engineer. More of an experienced engineer. I've been building software products for 30+ years. I think the role of the CTO varies based on the scale of the company. This article on the types of CTOs is useful framing: https://www.allthingsdistributed.com/2007/07/the_different_cto_roles.html https://www.allthingsdistributed.com/2007/07/the_different_c...

spopejoy 4y ago

There's a huge difference between a Dropbox and an Uber here. Dropbox is a technology company. This is famously a place where deeply technical leaders can achieve competitive advantage. The whole company exists to support the tech, so if the tech fails, bad. Uber (and most startups really) don't do tech, they use tech to drive sales. Of course the tech is important but it's a solution not a driver. Here I agree that a "well-rounded" tech-average CTO can be advantageous. Tech strategy is where everything converges. If products literally live or die by it, you better have a crack technologist at the top.

nickelcitymario 4y ago
For clarification: Are you suggesting Dropbox’s leaders aren’t well rounded? Or that they are and that they also need to be stellar engineers? I think you make a great point either way. I’d elaborate on that and say a business leader needs to deeply understand the product they make/sell, so if your core product is tech, I agree and see your point. But I still think they need to be really good at all facets of the business. They still need to understand the market and how to promote and how to close sales. Those skills don’t really develop if the only thing you do is engineering. Take HubSpot’s CTO Dharmesh for example. Brilliant engineer! But he applies his curiosity to understanding people and markets and solving unsolved problems. He understands the whole business. He also understands his own shortcomings and surrounds himself with people with complementary skills, because he knows full well that engineering alone isn’t enough.
- dshah 4y ago
  Thanks for the kind words. I don't consider myself a "brilliant" engineer. More of an experienced engineer. I've been building software products for 30+ years. I think the role of the CTO varies based on the scale of the company. This article on the types of CTOs is useful framing: https://www.allthingsdistributed.com/2007/07/the_different_cto_roles.html https://www.allthingsdistributed.com/2007/07/the_different_c...