How Habits Determine Your Success, with Jeff Winkler

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How habits determine your success is something our guest for today knows firsthand! Jeff Winkler is the co-founder of Origin Code Academy, an organization that helps students get the skills they need to start and succeed in software development.

On today’s show we begin by talking about good habits, bad habits and affirmations. Specifically we dig into which books are most helpful, and what Jeff does to persevere in the face of the many challenges of an entrepreneur’s daily life. Join us to dive into those topics and more on today’s CTO Studio!

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How to Evolve With Market Changes, with Benji Koltai

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The market can change in the blink of an eye so how to evolve with market changes is a valuable tool to have in your repertoire. Our guest today has done just that and he’s here to share his wisdom.

Benji Koltai is the CTO of Galley Solutions, a company that only exists because of what he learned from previous failures. Hear how it all began and how to evolve with market changes like Benji when you listen to this episode of CTO Studio.

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What It Means to be a Product Manager, with Jessica Sweeney

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Ask for a definition of the terms product manager and product management and you’ll get a different answer depending on who is answering the question! So what does it actually mean to be a product manager in the tech world?

Here to tell us is Jessica Sweeney. Jessica is a product management and marketing executive in the B2B, IoT and SaaS industries. During her career she’s found what a good PM does and doesn’t do, and why sometimes CTOs find themselves in the role of PM You’ll have to join us to hear the reasons on this episode of CTO Studio.

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How to Provide Solid Tooling as a CTO, with Aaron Contorer

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Audio Version

One of the talks Aaron Contorer gave that I’ll never forget is the talk in which he covered two topics: functional programming and how to provide solid tooling as a CTO. Those two topics are our focus for today’s show, and we waste no time jumping into the deep end!

Aaron has a technical background and built his company, FP Complete, around those very same subjects. You’ll hear how and why he started that company and much more when you listen in to today’s episode of CTO Studio. 

In this episode you’ll hear:

  • When does it make sense to start slow and when should you start quickly?
  • Why should CTOs be more optimistic and aggressive?
  • How to use bootstrapping to build something big in incremental steps.
  • What is the single most useful and most powerful management model?
  • What is the biggest problem we are facing in software today?
  • And so much more!

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When Aaron was at Microsoft and was managing a number of different R&D projects, he was surprised to learn how much of their time they were wasting using old-fashioned tools. He thinks even among the smartest IT people there is a bias to work around something and see that work-around as productive, when in reality is not.

He likens it to building a factory: every day with our work we are building a factory to build the things we really want done. We don’t run the web site by hand, for example, we build a factory that runs the web site. And if we are really good we build the factory that builds factories. And if we are in the tools business we build factories for those tools.

We are trying to get leverage in what we do, but we sometimes forget if we aren’t investing in building a better factory then the products that come out of our factory are not going to systematically improve or get any cheaper or more reliable. We need to invest in better tools and better processes – that is what being a CTO is all about according to Aaron.

An example he gives is a medical device company, one of his clients, that makes a successful medical device. They said they needed a data cloud that is would gather all the data from all their devices in the world and put that data together. This would allow all the users to see what is going on with their health and practitioners to see what is going on with groups of patients.

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So they built a V1 product to get something out, it was thrown together quickly. They thought maybe 10,000 people would use the app. It turns out the device was really good and people really liked the app, and a million people wanted to use the app. The problem became not just that the app was never designed for that amount of users, but neither was the data storage nor any of the infrastructure. The engineering systems themselves were never built to support that number of customers.

Next I asked Aaron to weigh in on whether it is true that devops is what happens when the engineering culture doesn’t take care of or consider the infrastructure.

To him, devops looks like this: you’ve got dev and you’ve got ops. In between the two is the middle ground called deployment where you are done building something but it’s not yet running on a production cloud or something similar. In general when talking about devops he considers it the family of technologies and design approaches that are all one big factory.

He gives the story of the Airbus A400M which fell from the sky in 2015 while they were doing a test flight. On that test flight they had designed their software in a tiny little computer inside every engine to control the fuel flow. The software must have passed its test because it was used in the build.

So they took it for a test run one morning with the new software added to the engines. The plane took off fine, but when the pilot adjusted the throttles downward all the engines went into idle except the one without the new software. So three engines turned into idle, and no matter what the pilot did with the controls he couldn’t get any more fuel into those other engines. As a result, the plane couldn’t maintain air speed and it fell from the sky, and everyone aboard died.

It turns out the software was fine, the problem was in the deployment. The person who did the update of the software into the engines did so using a non-automated system, and he missed a step. There was a file that didn’t get copied onto the engines, and it was the data file that said how much fuel to put into the engines. As a result, the engines couldn’t operate and there wasn’t a thorough enough system test to discover the error beforehand.

It’s a tragic story highlighting the importance of every aspect of development, deployment and operations.

We continue with that discussion before seguing into functional programming, why his company provides commercial Haskell tooling and work, what it’s been like being a CEO at FP Complete. You’ll hear from Aaron and I on those topics and more on today’s CTO Studio.

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The Importance of Psychology as a CTO, with Dr. Dan Stoneman

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Audio Version

Making the leap from a technical role into the CTO position requires many things, and not everyone makes the jump. One man who has is our guest today, Dr. Dan Stoneman.

Dan recently completed his doctorate in Organizational Industrial Psychology. He continues to learn and try to understand his world. Throughout the course of his career experiences, he’s learned the importance of psychology as a CTO and we get into why that is (and much more!) on today’s edition of CTO Studio.

In this episode you’ll hear:

  • What does servant leadership look like as a CTO?
  • What three pillars are needed for employees and organization to achieve success?
  • Why is going from a technical role to a CTO role so challenging?
  • What is a destructive hero and why does this role fail so often?
  • Can you just flip a switch to go from employee to manager?
  • And so much more!

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Dan has spoken at our CTO gatherings a few times, and one of those times he was the Chief Innovation Officer at a school district. I wanted him to repeat something he said during that talk when he was describing his career. He said it’s hard to describe as a path or a trajectory, it’s more of a personal mission of understanding. He believes a big part of his personal being is to understand the world in which he lives.

He was fascinated by his computers when he was young, so he started to figure out how to build and design them. He went to college and got a micro electronic engineering design degree. He learned how silicon becomes transitors, transitors become chips, and so on. So he designed transistors and chips and then circuit boards, at each stage he tried to understand how things fit together.

And from there software sits on top of the hardware, so next comes how to design software, and how to build the software. That leads to project management, program management and product design and customer use cases – all of which eventually lead to business strategies, leadership and psychology.

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Next we dig into how industrial organizational psychology (or I/O psychology) works. He believes each person does make their own decisions, so all you can do is set up an arena where they can be successful. He is a big proponent of the book Drive by Daniel Pink.

In that book, Daniel Pink talks about the three pillars of autonomy, mastery and purpose.

He explains as a leader if you create an arena based on servantship in which people have a great deal of autonomy, feel a great degree of mastery, have the proper training and understanding of their profession while also aligning their work to your organization the rest takes care of itself. That’s his take on what it means to be a leader.

I agree with that premise. When I became the CTO of my start-up I realized the people I was hiring weren’t there to be an extension of me; they weren’t there to go through my to-do list and get stuff done while I was focused on the other parts of the system.

But instead I was hiring human beings who could think for themselves and have their own ideas, and the best thing I could do would be to activate their creativity and get out of the way. I remember that realization was a massive moment for me!

Dan thinks that is true for many of us who started in engineering. It was for him, and so he’s been investigating organizational psychology and how to set up your organization. If you think of it like having a baseball team, organizational psychology would be looking at and deciding how best to set up the game field, the rules and regulations, what does the field look like and how are the umpires going to treat the field.

And industrial psychology is typically how to treat each individual player: what does each person need specifically to succeed? Industrial and organizational psychology work hand in glove, and why it’s called industrial organizational psychology.

On today’s episode of CTO Studio, Dan also tells us a failure he’s had in his career. Dan explains a great engineer does not make a great leader. In fact, they are completely opposite. He says he was a good engineer and as an engineer you are rewarded for finding needles in a haystack. If one transistor is out of place or one semi-colon is not in the right spot, everything falls apart.

It’s the exact opposite when you are a leader. As a leader the needles don’t matter, what matters is the haystack. How you can traverse the business arena and leadership arena doesn’t have to do with tiny nuances, it has to do with people and relationships.

We get into why taking a technical path to leadership is one of the most difficult, and why it’s such a high hurdle.Then we talk about the differences in the roles of CIOs and CTOs, if leadership becomes your responsibility as you gain experience and Dr. Dan’s productivity tips! You can join

Episode Resources:
Dan Stoneman on LinkedIn
Dan Stoneman on Twitter
Drive by Daniel Pink

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