271: What Big Tech Taught Me About Leading Without Code

 Can you really lead a tech company if you’re not technical yourself?

David Windley has done exactly that.

He’s the former CHRO at Yahoo, held senior HR roles at Microsoft, Intuit, and Activision, scaled a startup from <$1M to $50M as CEO, and now leads HootRecruit — a recruiting tech company. 

David has spent his career at the intersection of people, technology, and leadership.

Listen to this episode to learn:

• How non-technical founders blow it when hiring their first developers
• Why a startup CTO is nothing like a corporate CTO
• The “Windley Rule” — why engineers must make sure you understand, not the other way around

If you’ve ever felt shut out of the tech conversation because you don’t code, this episode will show you how to step up as a leader.

Resources from this Episode

Tech for Non-Technical Founders course https://www.techfornontechies.co/tech-for-non-technical-founders

Growth Through Innovation

If your organisation wants to drive revenue through innovation, book a call with us here.

Our workshops and innovation strategies have helped Constellation Brands, the Royal Bank of Canada and Oxford University.

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TRANSCRIPT

David Windley  0:00  

Is like you need to be able to explain this, so that when we can understand it, now understand the context. I'm the human resources person, so from a job title, the kind of the least technical person right in the room, even though I do have an understanding of tech. But the point was that you need to be able to explain your product, even if it's a very technical product, right, if you're going out to the marketplace, so that a non technical person can understand.

Sophia Matveeva  0:36  

Hello and welcome to the tech for non techie podcast. I'm your host. Sophia Matveeva, if you're a non technical founder, building a tech product or adding AI to your business, you're in the right place. Each week, you'll get practical strategies, step by step, playbooks and real world case studies to help you launch and scale a tech business without learning to code, and this is not another startup show full of jargon venture capital theater or tech bro bravado. Here we focus on building useful products that make money without Harry and without code. I've written for the Harvard Business Review and lectured at Oxford, London Business School and Chicago Booth, so you are in safe hands. I've also helped hundreds of founders go from concept to scalable product, and now it's your turn, so let's dive in.

Hello, smart people. How are you today? I got a question for you. What do Yahoo and a Coldplay concert have in common? Well, they're all HR nightmares, and today's guest has lived them. Today you're going to hear from David Windley. David was the CHRO at Yahoo, and he has also held executive roles at Microsoft and Intuit and Activision, and he also scaled a startup to 50 million in revenue, and that startup is called IQ talent, and now he is the CEO of another company called hoot recruit, and that's a recruiting tech company, and he sits on various boards anyway. Why should you care about this? David is a non technical leader who runs a tech company. He has also been a non technical leader at the helm of seriously successful Silicon Valley tech companies, and so he's proof that you don't need to be a technical person to drive innovation. Instead, you really need to understand the problem that you're solving. So you need that vision, you need judgment, and you also need the ability to hire the right people so they can build the technology. In this episode, you will hear what non technical founders get wrong when they hire developers. You'll hear the difference between startup CTOs and big company CTOs, and this is really important, because people make mistakes, and I don't want you to do that. And you'll also hear about the windy rules, and that's basically about why it's the engineer's job to make sure that you understand, not necessarily the other way around. If you've ever felt left out of the conversation by tech bros, this one is for you, David, when we spoke earlier, you told me that Yahoo executives were really determined to decide whether they were running a tech company or a media company. Now, why did that matter? It's a good question. I think a lot of companies here in Silicon Valley, I don't want to say, struggle with that, but that it is important more about the culture of the company and sort of how you approach the market. Let me tell you a little bit more about what I mean. I also work for Microsoft, and Microsoft is clearly a tech company. I don't think anyone dispute that. And what is the difference there is, I think, you know, Microsoft leads with technology. They obviously have great products that you know, in many cases, dominate their market, but from their founding and ongoingly, they're always researching the next Tech and then figuring out that technology, what sort of products may be come out of that, and introducing the market like an entrepreneur would, right? I think Google, clearly, you would say the tech company. I think Yahoo is, was, is when I was there in the in the 2000s

David Windley  4:27  

and they were the leader in digital media. So I understand the argument and why people care right a lot of its identity. And I think for technologists, they want to be part of a tech company, but it really should be irrelevant. It's focused on what is your business, trying to figure out how to succeed in the business you're in, and using technology to succeed in that business. Again, I'll go back to say, a Netflix or an Airbnb or Uber, right? And I think, yes, it. It was a discussion as a discussion that seems to always happen here in Silicon Valley. But I think what people should focus on, and especially if you're starting your company, is maybe there's new technology that got you to come up with a new product or whatever, but at some point you are going to be competing in a market. You know, what is your solution? What are your customers buying? And that's the business you're in. And stay focused on that, and being number one at that, that would be my take on it.

Sophia Matveeva  5:37  

We make this distinction between tech enabled and tech first on the show. And I generally tend to think that non technical founders are really well placed to lead tech enabled businesses, because usually they they, or we rather, have a vision, have an understanding of a problem. So it's usually some sort of business problem, or a human problem, basically, some sort of problem that somebody is willing to pay to solve, and then we use technology, or, you know, we hire people to help us use technology to solve that problem. But our we can lead these companies, because we've got the insight that really makes the money. And the insight, frankly, is not technology. Yeah. Would you agree with that? Would you say that if you're a non technical founder, tech enabled, that's

really the way to go?

David Windley  6:30  

Absolutely, I think you're going to be hard pressed to find many companies that are going to be tech enabled, or that technology will help you with a competitive edge. I mean, you know, even traditional companies these days need to use technology in a way to give them a competitive edge. But, yeah, absolutely, if you're talking to founders out there, you're you're either solving a business problem or a consumer problem, staying on top of new technologies. The newest one is like generative AI these days, but staying on top of that, understanding its capabilities, so that you can conceive of maybe new business models, new ways of approaching your business, your market, with this technology.

Sophia Matveeva  7:19  

And so in your experience, you have worked in large, we can say tech and tech enabled businesses. And you've also, you're now leading your own tech company, tech enabled company, and you're a non technical leader. And so how do you absorb this new knowledge. Because I think what tends to happen is that maybe, if you are living in Silicon Valley, you kind of just absorb it, because it's everywhere, and you don't even realize you're absorbing it the way, you know, if you're living like I used to live in France, and I used to know so much about different wines and different cheeses, I didn't take a course. It's just, you know, everybody knows you almost breathe it in the air. You know, now, I'm not impressed. I don't really remember it. So I think I would assume, and from what I've seen, is that people in Silicon Valley, who worked in Silicon Valley companies, they just absorb it. But when you see people who haven't had that path, how would you say to them, okay, you do need to, you know, you're a business person. You need to learn something about tech. But, you know, don't go crazy and take a six month long coding course, because that's just going to be

David Windley  8:29  

pointless. Yep, yep. No, you're absolutely right. I think here, you know your coffee conversations, your cocktail conversations is, is about tech. So you're right. You tend to learn a lot or absorb, as you said, understanding of Tech. Go out and seek it. And there's information out there for any of us to understand.

Sophia Matveeva  8:50  

And the key there is, the information is there, but you actually have to make an effort. You know, Silicon Valley, maybe you don't the way in France, you just learn about wine. But in other places, you know, put some time in your calendar to say that, okay, I'm going to dedicate, I don't know, three hours a week. And you know, they can be some some of those hours can be listening to a podcast while you're doing something else, but just be conscious about it, because unless you do it,

it's just not going to

David Windley  9:18  

happen. Yeah, and the follow on to that. It's sort of at what level you don't need to take a Python class, right, and become a coder. I would say it's more the equivalent I went to school a long time ago, computer science. 101102, right? Understand conceptually about these technologies. So let's talk about AI. So you need to take the AI, 101102, maybe a little bit deeper types of courses in education, right? You need to understand how it works, right? You know, conceptually, and you need to understand its capabilities and et cetera. So that's the level you don't. Have to become a machine learning engineer, and so I think that's important too. I think some people think they have to go into the guts of the technology and really understand you're not going to be a chip designer, right? But you need to understand how the chip works, how a GPU works, what makes it different than the previous CPUs, et cetera, but yeah, you don't have to become a hardware designer.

Sophia Matveeva  10:26  

And so now let's talk about your journey as a non technical founder. So you worked in these really large companies, and then you decided to set up your own business. Why on earth would you do that after being in a really nice position where you're respected, you're getting paid, well, everybody's really impressed, then you start a company, nobody knows its name. You don't know when you're going to get paid. What on earth happened?

David Windley  10:53  

Yeah, I didn't like retire from corporate and say I want to do startups, necessarily. So the journey is sometimes you're lucky enough here in Silicon Valley, Silicon Valley to retire fairly early. And so I did retire from corporate and entered what I call my portfolio phase of my career. Started getting on boards. I personally angel investor in the space I know, which is the combination of tech and talent space. So I invested in some companies in that area. We grew that company from less than a million to a $50 million company. At its peak, we did sell it to Caldwell partners. And so that was my first journey as sort of an entrepreneur, building a company, and then within that company, again, being a consumer of tech for recruiting and seeing where technology was going, which I can see with the with AI, that AI could do more and more of what the recruiter's job is. And so we started building software within that company, and then I convinced Caldwell to let me spin that out, and that is my tech startup coot recruit. So that's kind of my journey.

Sophia Matveeva  12:07  

The line that I'm seeing here is basically your professional expertise working in HR and recruitment at these large companies, understanding that problem, when you know all the problems that come with HR, which are very colorful, you know, especially, especially if you go to a cold, black hotel, that's an HR nightmare. So, God, I forgot what I was about to say now, so there was this, there was this line of your expertise, and that expertise essentially got developed as as you group, but also then got scaled with technology. I think this something that I really want non technical innovators to see, is that I think the media really loves the story of a 20 year old dropout who then becomes a billionaire. And yes, that sometimes happens, really annoying, but most of the time it doesn't right. People who become successful entrepreneurs, they start their companies in their 40s, and there was a reason for that, because

you've got to actually know what you're doing

a little bit.

David Windley  13:06  

But yes, yes, no, that's true, and I forget the exact stat, but yes, said that is definitely true, that most entrepreneurial businesses are started people that are older than 20 and people that have knowledge of whatever kind of business or process that they develop. And so, yeah, so I would say to your other entrepreneurs, or future entrepreneurs out there, take something that you understand, that you know that, where you see that there's a problem to be solved or a better way to do something. And then, yes, if technology, and more times than not, technology can help you with a better way of doing things, yes, then absolutely, bring in the tech to enable your business to be successful.

Sophia Matveeva  13:56  

So now I want to ask about your original area of expertise, which is recruitment, because you have interviewed engineers when you're running HR at Yahoo, but you also interviewed tech people for your tiny startup.

Yeah. So

how so? First

of all, how different is that process, you know, big company hiring versus time you start up hiring,

David Windley  14:23  

yeah, for me, it's really different. Because for me, you know, being at the C suite or executive level most of the time when I'm hiring, or you're in the interview process with technologists, I'm looking for the leader, right? And so, and typically I'd be part of a team, an interview team, and so I'd have other people on the interview team that can assess more the technical capabilities of that person, and I would be focused on more their leadership characteristics and other characteristics that make you a great teammate or an executive when I'm in. Viewing for my small company, I do need to have some understanding of this person gonna be able to code and do the tech, right? So, you know, when I've hired I've only got two engineers, is I have to lean on, you know, their experience, right, looking at what they've actually accomplished, right? So I may not be able to go and understand their code specifically back and see the results, right? So what have you accomplished? What did you have you done? And see if that's good product, good, good results, and then heavily reference right their background, what they've done, and talk to their leaders, their other technical leaders.

Sophia Matveeva  15:43  

So this sounds like common sense, because, you know, I find that a lot of our students get really freaked out about hiring developments. And I think, well, you know, most of us have hired a lawyer at some point, right, whether it's to buy a house or, you know, some for something, but none of us decided that we need to go to law school before we hire a lawyer. We kind of be figured out generally what they're doing, but, but it was the same thing we look at, okay, does this person get results, or does this person have a track record of, you know, creating contracts, contracts that are, you know, then fall apart and, you know, we we see, Okay, who else have they worked for? And based on that, you know, we generally tend to make our decisions, and it's good to see that you were saying that actually technology use the same things. You use the same concept as you would,

David Windley  16:36  

yeah, exactly. And you will have to lean into those other indicators much more than if it was in your area of expertise, right where you can interview, ask the right questions, you can get a feel. But you're right. It's just like anything that you're not an expert in, you're gonna have to rely on look at the actual results, see how they've done. Referenced very you know, reference through looking at results, the reference to talking to people? Yeah, the same methodology.

Sophia Matveeva  17:04  

And also, I want to

differentiate between what you're looking for in a big tech leader versus in a startup, because, you know, you can even if you have a CTO in a startup, let's say that startup has 10 people, and then you have the CTO of Yahoo.

Are they the same job?

David Windley  17:25  

No, very, very different. And so I think, you know, the key is, as we say here in America, you got to roll up your sleeves right as a startup and and so I think that's critical, because there are a lot of people that are very capable, but for, you know, depending on where they are in their career, just their own mindset, it might be hard for them to really roll up their sleeves and work 12 hours a day, or 10 hours a day at least. And, you know, add some weekend time, which is necessary to start up. So, yeah, I think that's the two major characteristics that you have to look for at a startup that would be different, is, can someone really get in and do the details?

Sophia Matveeva  18:11  

You can't say that. You know, I've got this PhD from Oxford. I'm this brilliant person. It's like, well, we all do, but the print is broken. It has to be fixed.

David Windley  18:22  

That's the rolling up your sleeves Exactly. If you're not willing to do that, then, yeah, that's not a great match.

Sophia Matveeva  18:28  

So what does a CTO at a company like Yahoo do? Are they writing your code?

David Windley  18:34  

Yeah, yeah. So in fact, at a big company, you have different tech leaders and organizations organize differently, but you could see that there is a leader of development, like product development, so the one that's actually the products that are being developed, being engineered. You know, sometimes it's even just head of engineering, right? Sometimes they put it together product and engineering, so they're different constructions. And then you also often have someone set aside doing more just pure technology. I think

Sophia Matveeva  19:06  

this actually is a good demonstration, like, I don't think you meant it, but I think it's a good demonstration of why people from big companies, when they join a small company, why it can be a complete disaster. Because, you know, if they're used to doing research, which is really useful for a company like Microsoft, for a startup, you can't only do research, and there's a token, AI, but that's a whole world of its own, right. Yeah. And so before I let you go, there's one thing I want to ask you. One more thing I want to ask you, told me earlier on about the Windley rule. So tell me, tell the audience, what is the Windley rule and why did

David Windley  19:50  

it arrive? About? Yeah, earlier in my career, I used to work for a company, Silicon Graphics, which for a lot of your younger viewers may not know Silicon Graphics, but in. 90s Silicon Graphics. Basically invented the graphics chip, the GPU, yes, of Nvidia, which is doing now, which is behind all these AI supercomputer servers, right? But they were the first sort of graphics company. They had graphics chips, the graphic language. So very, technical company. They kind of invented the graphics. I was an executive in, you know, many meetings. And in one meeting, we had one of our product people kind of explaining and talking to the team, and one of our executives, the top executive, you know, was talked looked at the guy, and he like, whatever his name was, I'm not going to declare his name. He's like, You need to be able to explain this so that winley can understand it. Now understand the context. I'm the human resources person, so from a job title point of view, the kind of the least technical person right in the room, even though I do have an understanding of tech. But the point was that you need to be able to explain your product, even if it's a very technical product, right, if you're going out to the marketplace, so that a non technical person can understand it. So that was the winley role. He was saying it jokingly, but then it caught on inside the company. It was like, when someone's a tech person is talking too techie to a general audience. You know, people would come back and say, yeah, the Windley rule, you know, make sure that Windley can understand it. So kind of jumping. But the point is, is well taken.

Sophia Matveeva  21:37  

I think this is really useful for non technical leaders to under to actually know that this is a thing, because I've certainly been in situations when a technologist is speaking and I have no idea what they're talking about. I don't understand at all. And at the start of my journey into tech, I used to think that I am doing something wrong. I should figure this out. And so I would secretly go on YouTube and try to watch these technical videos, which would be even more confusing, and it would just be a road to nowhere. Yeah, but now my view, what you're basically saying is that okay if a technical person is speaking to other tech people, fine, speak your language, but if you're coming outside that bug bubble, if you're speaking to business leaders, and often business leaders are the budget holders. They're important. So then it is upon the engineer. It is upon the technical person to speak to us in a way that we understand. It doesn't mean that we don't make any effort, like you said. You know, we also make an effort to learn, but it's an effort from both sides, and it's like any success

David Windley  22:46  

relationship. I think that's the key. Yeah, what you said is the key is, you know, we talked earlier about non technical people knowing enough about the tech, right? Knowing that conceptually what it does what, and then the tech person needs to lift it up to that abstraction layer and talk in those terms, and then that's where we can intercept, right? So if we educate ourselves enough to understand the tech at an abstraction level, what it can do, what it's capable of, and then the technologist, instead of being in the weeds, bring it up to that level, then that's the intersection, and we both have to make that effort absolutely

Sophia Matveeva  23:23  

Well, I think this is a really, really good and positive note to end on, and I think it's also just a sign of any kind of good relationship, right? It's both people thinking about the other person's perspective and thinking, Okay, how what can I do to make life better, to make it easier for the other person, and that's how we have great relationships, great friendships and so on. So thank you so much for joining us, David. And if people want to learn more from you, where can they find you?

David Windley  23:54  

Well, they can come to hoot recruit.com that's our company. And if they wanted to find me directly. I'm at David at IQ recruit.com Awesome.

Sophia Matveeva  24:05  

Well, thank you so much. All right, thanks. I hope you found this conversation useful. But remember, inspiration without action is just entertainment, and frankly, there's so much better entertainment out there than listening to business podcast. So if you're serious about building your product and changing your career, then check out our signature tech for non technical founders program. There you'll get the framework that my students have used to go from idea to product. There you'll get the framework that our students have used to go from idea to product to get into top accelerators, raise funding and even land dream jobs in venture capital and product leadership. Not bad. You learn how to go from idea to life product. You learn how to avoid wasting money, super important. And also you will figure out when to use AI and when to hide the price the link. For the tech for non technical founders program is in the show notes, or just go to tech for non techies.co. And on that note, thank you very much for listening today, and I shall be back in your delightful smart years next week. Ciao.