Confessions of First-time Startup CTO

The struggles and glory of growing from a coder to leader

"I don't think I can keep going."

It came out of nowhere, so I just stayed silent.

"I mean I love coding. I love what we are building. I just don't love my job." 

I first met Chris at an early mentorship session of the accelerator her startup attended. We were paired up based on similar industry experiences and found we had an instant rapport. Since meeting several months back, we got into a regular cadence of chatting every two weeks for advice and brainstorming.

Chris was the pragmatic, down to earth type. Never prone to exaggeration or overly expressive conversation, we tended to stick with more practical how-to topics and matter of fact things. Our chats were always technically minded, so this was new territory.

I replied, “What about the job do you not love?”

“Not sure, I just feel like I am failing at everything. There is all this other stuff I was never prepared for and the one thing I’m good at, coding, I hardly do anymore!”

Chris let out a sigh and looked away. This was the first time I saw her optimism turn to defeat as she seemed resigned to her inadequacy.

I have heard many similar thoughts from first-time CTO’s in startups. What I shared above is a real conversation, just with the name changed to protect the identity of someone that shared her personal struggles in confidence. The common thread in each conversation though is the feeling of not being suited for the role.

The role of a Chief Technical Officer is not an easy one. There is the constant balancing act of keeping the engineering team productive and shipping reliable code with the need to be the technical ambassador to the executive team and board.

For CTO’s in early stage startups however, the stakes are higher. Often much of the initial codebase is the product of the CTO, who starts out as the first developer. Then there is the added pressure of building an entire engineering organization from the ground up. It is a huge responsibility that can humble the most confident of persons.

Imposter syndrome is the phrase most often used to describe the feeling of inadequacy in one’s work. I tend not to use this phrase given that it can reinforce gender biases. Instead I call this the confidence gap, the space between first entering into a new role to the point in time when enough exposure and experiences in the role fills the gap. Regardless of experience and background, we all feel the confidence gap.

As a startup mentor and host for CTO roundtables, I hear many of the same common struggles that emerge in our discussions. Rarely are the questions of a technical nature such as coding practices or architecture considerations. The most popular sessions are on leadership and management topics, especially when working with first-time CTO’s.

When I look back at my notes and reflect on my conversations with Chris, the three most common challenges for first time startup CTO’s were in becoming more business oriented, building out an engineering team, and managing staff. Let’s dive deeper into each of these:

Going from Chief Coder to Business Leader

A startup CTO is often co-founder and the very first developer. Even if part of a team, the team itself is small and the CTO is usually the most experienced and technically adept. As the startup grows however, the codebase expands, the feature requests and scaling needs increase, and the engineering team expands. It is at this point that the CTO needs to be more than just the technical leader.

This is a huge mindset shift. First is the realization that ownership and control of the code has to be entrusted to others. It simply becomes too overwhelming to know all that is going on in the code. Second is the need to engage as much with peers as with the engineering team, working in unison with product, marketing, sales, support, HR, and finance.

The key to navigating this shift is trust. First is earning trust with peers through listening and understanding situations from their perspective. I often recommend the books “Never Split the Difference” and “Influence: The Psychology of Persuasion” as helpful resources. Though these are thought of as books on negotiation, they provide useful skills and strategies for working collaboratively with others and navigating difficult conversations

The other aspect of trust is the need to place trust in those on the engineering team to take ownership. This reminds me of something Steve Jobs once said about talent:

"It doesn't make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do."

This means bringing in the type of people into the engineering organization that are ready to take on responsibility and to deliver results. That gets us to the next point...

Making Tech Hiring an Organizational Muscle

Hiring in the early days for developers and technical staff often means relying on personal networks. This could be school connections, previous work colleagues, friends, etc. Recruiting, onboarding, and managing is relatively easy at this stage because the team is small, the complexity of the product and code is low, and you probably have past experience with everyone on the team.

Then at the point when the startup is ready to grow and the need for more engineers becomes critical, two issues emerge. First, where do you find talent? Second, how to hire the right talent for the work required?

This is not a task that can be tossed over the wall to recruiters and HR to manage. The most important role a CTO plays in a startup is bringing on the right technical talent. This means partnering with HR and recruiters and taking a strategic approach to hiring, starting with culture and employee branding, creating a thoughtful candidate experience and interview process, and following through with onboarding and training.

Managing Team and Individual Performance

The last challenge is the one that often causes the most grief and anxiety for first-time startup CTO’s. This is the part of the job that is messy because it is not code issues, it is purely about the people. There is no algorithm for solving the mystery of people.

This is why spending extra time on shaping the culture early on and building a robust hiring and onboarding process is so important. This sets the tone for what is expected and provides the roadmap for employees to fit into the team and succeed in their role.

Things do not always go as expected however. People are messy with all sorts of biases and ticks that make management such an adventure. Culture and the values you espouse will be the guide, but I also recommend leaders take to heart what folks such as Brene Brown and Simon Sinek share about leadership, which is that effective leaders serve others. As Simon Sinek says:

“A leader’s job is not to do the work for others, it’s to help others figure out how to do it themselves, to get things done, and to succeed beyond what they thought possible.”

Often the process to help those on your team reach their potential involves awkward and difficult conversations. One book mentioned in previous CTO forums is the book Radical Candor by Kim Scott with the caveat that some of the advice in the book will not translate well in certain cultures.

I also recommend finding mentors and others you trust to help talk through difficult situations when they arise. This can be through various startup groups, but also local CTO communities like the ones AWS partners with or hosts in various regions globally. Leadership is already a tough journey, especially in fast-paced startups, so there is no need to struggle on that path alone.

There are certainly many other challenges that come up in my conversations with first time CTO’s. Working on the three challenges above though is usually enough to establish a strong foundation for success and filling the confidence gap. Leadership is a lifelong learning process, so expect to be stretched and tested along the way as you gain your footing as a CTO that inspires the team and delivers results.

What are your superpowers as a technology leader? How are you able to develop your leadership skills on an ongoing basis while at work?

Mark Birch, Editor & Founder of DEV.BIZ.OPS

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The AWS Startups club on Clubhouse has passed 1,500 members. Plus, I am super excited to see that the Android app for Clubhouse is now in limited release. If you want an invite, please send me a message and provide your mobile number.

I am also excited about a bunch of shows coming up on the topic of building a SaaS business in the cloud, the intersection of music and tech startups with the rapper Jim Jones, and the one today (May 13 at 6 PM ET / 3 PM PT US) with the FinTech Startups team at AWS. We plan to talk about FinTech trends, AWS customer stories, and have Q&A with our community. Come join us using this link to the event!

If you want to be on the show or have an idea for a topic, please let me know! We have shows in the APAC, EMEA, and Americas time zones, and always open to interesting content 😁

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