Joe Conley Tagged leadership

What is a CTO?

Tue, 01 Sep 2020 00:00:00 +0000

I’ve spent a lot of time thinking about what a CTO is. It’s important to really think through this role as it can have such a huge impact on companies both large and small. You can search the web for “startup CTO vs. big company CTO”, “CTO vs. VP Engineering”, etc., but those debates miss the point. What matters is understanding the function of a CTO in your organization. And I assert that a CTO is an executive who serves the business through the deployment of technology.

That’s it! The details of implementation will vary widely based on company, industry, and the strengths and weaknesses of the individual CTO. But at its heart, this role requires a leader who has a strong fundamental understanding of technology and how to use it to support a business.

What, then, is technology? It’s easy to assume that things just “get better” over time. We’ve emerged from the cave and tilled the earth, dammed the streams, and harnessed the power of the sun as we march towards greater standard of living. However, none of these advancements were inevitable. Progress depends on us inventing the future.

This topic is more important than ever. It’s hard to argue that software is eating the world, and as a result, every company is now becoming software. Technology advancement has accelerated change in every walk of life. Powered by trends of cheap computing power and new techniques to analyze data, this wave of extracting value from data is overhauling every and any domain it gets its hands on.

Is this wave of technological progress “good”? Any type of significant change can and will cause issues like job displacement, but I believe that as technology helps automate mundane labor, it should create opportunities for human beings to focus on higher-level, more creative work. This underscores the importance of having strong, thoughtful education for everyone young and old.

Given the speed and complexity of these trends, it’s important to have someone who understands technology at a sufficiently deep level (software, hardware, whatever). I’ve found the best CTO’s form strong opinions about their technology choices, yet dispassionately remain open to searching for the best solution. They rely on tried-and-true systems rather than chase what’s trendy. They push hard for excellence, but balance that with sensitivity to solving the customer’s problem in a cost-effective way.

It’s also important to note that a CTO is an executive. I think the toughest thing for a newly-dubbed CTO to learn is how to scale not just code but an entire organization. As a lead engineer or architect, your choices are mostly constrained to scaling infrastructure or analyzing data. Once that “C” shows up in your title, however, your biggest challenges tend to be people-problems. Which seats on the bus do I fill first? Can I grow this junior resource into a contributor, or do we need to move on? Can I make peace between two warring factions? You’re definitely moving “up the stack” here, and it requires a wholly different skillset than what got you here.

Personally, I value the opportunities I’ve had to serve as CTO because I know that I can have a meaningful impact on a company. I know my decisions will have consequences, and I relish the challenge to move the needle where I can. Most of all I enjoy aligning a team towards a common goal. By its nature, technology strives to improve how we live our lives, and to serve as the steward for its application is a privilege.

I’ve also been blessed to have found an informal network of mentors who I rely on regularly when facing tough decisions. I’m hoping I can start to do the same.

At the end of the day, it’s just really cool to helping spearhead the deployment of technology for an organization. I’m a huge Elon Musk fan for a lot of reasons, but his quote about why he went into engineering really spoke to me:

Just really cool to think about engineering in terms of building new things which enable really smart people to keep making progress and ultimately improve our collective consciousness. It’s inspiring to think we’re all trying to play a part to create a better future. It’s why I pivoted from a pure mathematics career to one grounded in technology. Because it’s “what’s next”

Shape Up or Ship Out!

Wed, 29 Jul 2020 00:00:00 +0000

Have you worked on a software team that consistently shipped high-quality work on-time? I’ve seen companies large and small have plenty of difficult delivering software. Either things break in production, or things don’t ship on time, or worst-case both.

And in most cases, the antidote was supposedly to “be more agile”. Planning poker, Fiobancci story pointing, backlog grooming, and all of the other well-trodden ceremony should make these issues disappear. And to be fair, I’ve seen these things “work”, but only to a certain extent, and usually over the short-run. I’ve tried them myself with mixed results, and an underlying apprehension I could never put my finger on. Did software engineers pick this profession out of a love of project estimation and ticket management tooling? Does any of this feel like a natural way to treat human beings?

And so it is with this undercurrent of dissatisfaction that I recently found Shape Up by Ryan Singer. It’s a refreshing take on how to craft software. The book is a perfect size to read, and has a great blend of thoughtful ideas paired with practical advice from the trenches of a well-known and successful product company, Basecamp.

This book hit a lot of notes for me, but the biggest idea was how work is shaped and handed off to the development team. Projects aren’t chopped up into tickets, doled out and estimated. The product strategy team defines a project with CLEAR BOUNDARIES and a FIXED TIMELINE, and lets the development team work through the details and manage themselves, with clear checkpoints along the way. This allows developers to use their brains to come up with their own implementation ideas, frees up the product team to stay focused on high-level strategy, and doesn’t require a middle-manager (i.e. Scrum Master) for communication.

This is the essence of management that delegates without abdicating responsibility. Shaping creates guardrails to allow a team to grow and experiment without hand-holding, trusting but verifying that the project’s thoughtful criteria will be met. I think these ideas would be borderline radical in most companies I’ve seen.

Why does any of this matter? Because I believe technology companies can be agents of change. Crafting tools that help automate and streamline rote tasks so human beings can focus more on human work should be the ultimate goal of most technology offerings.

In that same spirit, how do we as technology leaders ensure that the builders of technology are allowed to do more human work? By giving them more responsibility in an environment where they feel safe. I think the true measure of success for any company is not just revenue growth or user adoption but how did your team grow professionally and personally? Otherwise, what’s the point in winning?

In addition to managing teams, I think the concept of shaping and fixed deadlines helps us manage ourselves too. Rather than keeping an iron-clad todo list, think at a higher level what you’d like to accomplish for a given week or month, make sure you focus on achieving the core “functionality”, and then DELIVER. Keeping a blanket list can trick your brain into thinking all tasks are created equal and MUST be done. Being more thoughtful about time constraints and scope helps to reframe and reorient your mind, and start building your shipping muscles.

This speaks to another key point that Singer, Clayton Christensen in Competing Against Luck , and even Peter Thiel have all talked about. Namely, a lot of the time the key to solving a problem is how to frame the question. Whether it’s deciding what features to build into a product, how to build out your organization, or how to spend your life, the way we frame the question helps guide us to the answer.

Ultimately, finding humane ways to ship software will be an ongoing challenge for leaders and contributors alike. Amid the rise of automated coding tools like GPT-3, there will be a need for thoughtful, effective leadership that understands what questions to ask and what tools to build.

So Shape Up, or ship out!

Leadership Aboard the Santa Fe

Thu, 03 Oct 2019 00:00:00 +0000

What is leadership? It’s certainly a fancy term. It adorns countless corporate walls paired with some inspirational message or image. It appears as a common requirement for most management-level job applications. It can even inspire folks to come together in an almost cult-like fashion:

But defining leadership can be tricky. We can use words like humility, decision-making, servant to try to arrive at a definition, but that’s boring and often incomplete.

Leader-Follower to Leader-Leader

I recently read L. David Marquet’s Turn This Ship Around!, and came across a truly great example of what it means to be a leader. In short, leadership is creating an environment that helps your subordinates grow into becoming leaders themselves. Marquet did this in a seemingly unlikely setting: aboard a submarine in the U.S. Navy.

How?

Here are my main takeaways from the book to how to shift to this new paradigm:

Create an environment of ownership

It’s important that the environment is tailored to allow reports to make decisions and think on their own, but be accountable for their decisions. Marquet encouraged this by requiring his junior officers to recommend what actions to take. Instead of Marquet giving orders, he’d have his reports make decisions, having them say “I intend to” before acting. e.g. “I intend to take the ship up to periscope depth…”, while Marquet would give simple confirmation. Even little things like language can help encourage passive officers to think independently.

Delegate but don’t abdicate

Marquet tried out a Leader-Leader experiment on the U.S.S. Will Rogers without much thought into how it was implemented. This led to an oversight in readiness, a failed inspection, and a quick transfer to a Soviet outpost where he could spend time reflecting on just how poorly his first efforts had been. Simply delegating tasks without thought to how they’d be carried out is a recipe for failure.

Once he got another shot aboard the U.S.S. Santa Fe, he focused more on developing the level of competency of his officers. He resisted the urge to dictate solutions to problems, but instead gave his folks latitude to work through issues. As Marquet succinctly put it, “Don’t brief, certify”.

Communicate vision without dictating

Communication is paramount. Especially for significant changes that are new or uncomfortable, you can never communicate too much what your vision is.

Applied to Tech

I’ve certainly struggled with delegating, especially on a small team where there’s plenty of work to go around and never enough bodies to do the work. I think I’ve gotten better at communicating context and the necessary details of a particular issue or task, however I know sometimes I’ll lead with my proposed solution without allowing my reports to come up with their own design.

But overall the ideas in this book have helped me start to think more about how I operate and how I can do a better job of creating an environment that creates great leaders.

Results

Marquet’s work resulted in the Santa Fe earning a record number of awards in both excellence and most improved. Furthermore, Marquet’s officers were promoted at unusually high rates to lead their own ships, and applied most of what they learned aboard the Santa Fe to their own ships.

In business, it’s easy to get caught up in optimizing specific metrics, growing profits or increasing market share. But doesn’t that all pale in comparison to helping others grow? To inspiring others to build a brighter future? In that way, leadership can be boiled down to priorities. How you choose to spend your time, what you choose to value above all, and how you choose to impart those beliefs to others.

How do you define leadership?