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By: Debbie Madden

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May 18th, 2015

7 Habits of Highly Successful CTOs

It’s Monday morning at 10:30am. Jon, CTO of Acme Co., has a decision to make. He’s having trouble scaling his Ruby on Rails application and is considering migrating to Python. In fact, he’s had this issue weighing on him for over a month now. He knows he can’t put off the decision any longer. His team is looking to him to make the call. He’s gathered input and weighed options. Yet, he fears he doesn’t fully have all information he needs to make a decision. What should he do?

The truth is: In order to be a successful CTO, Jon needs to get good at making high quality decisions quickly. To learn how you can make high quality decisions quickly, and to get key insights into 7 habits of highly successful CTOs, read on.

I’ve been working with CTOs for more than 20 years.

Over the years, I’ve seen seven distinct habits weave a thread among the most successful of the bunch. Whether you are a veteran CTO or aspire to be one, executing well on these seven distinct behaviors will go a long way in helping you achieve success in your career. Today, I’m going to share with you the secrets behind executing them well.

Which is why I’m going to give you a test you can take right now for immediate feedback on how good of a tech leader you are. 

The 7 Habits of a Highly Successful CTO

Use the links below to jump to specific sections of the post.

Habit #1: Make High Quality Decisions Quickly

Habit #2: Know When To Code

Habit #3: Foster Trust

Habit #4: Delegate Effectively

Habit #5: Manage Up

Habit #6: Set expectations & Measure progress

Habit #7: Give timely feedback

Habit #1: Make High Quality Decisions Quickly

We’ve all been there with Jon. Whether you’d had to make the call on migrating your tech stack, breaking out your monolith, or firing an employee. CTOs are faced with difficult, high impactful decisions all the time. Yet, it’s a mistake to sit and let the issues fester. Come to grips with the fact that you are never going to have 100% of the information you need. Instead, use these three tips to help you move from analysis paralysis into action:

  1. Rely on the 80/20 rule. You’re likely never going to be 100% sure about anything. Get enough info to be 80% sure and make the decision. As a bunch, CTOs are analytical, and I get that. It’s the analytical thinking that makes you you. Yet, at some point you have to make a call.
  2. Ratify a decision-making process in your company - There are many to choose from and implementing one is a lightweight way to add confidence that you know who’s responsible for each area of your business. This can save hours of time and makes decision-making 1,000 times more effective.
  3. Actively manage the biggest risks - Read the book Waltzing with Bears. It walks through a powerful process to use to identify all potential risks and create a plan to proactively manage the biggest threats and fears. This way, you are proactive about risks and they don’t paralyze you. 

Habit #2: Know When To Code

Knowing HOW TO Code is a given. The more important thing as a CTO is knowing WHEN TO code.

I know CTOs that code 100% of the time, and CTOs that code 0% of the time. Successful CTOs are proactive about deciding how much of their week to spend inside the code. They plan for it and iterate on that plan.

As an example, at Stride, our CTO spends 20% of his time coding, by design. And our VP of Engineering spends 10% of her time coding, by design. They don’t walk into the office Monday morning and say “Hmmm, I wonder if I should code today.”

Pro Tips:

  • This will and should change over time. If you are a CTO of a 3 person dev team, you might start out coding 70% of the time. If you grow into a 20 person team, you may then code 25% of the time.
  • The key is to be PROACTIVE about the decision and understand WHY you’ve made that decision. After you’ve made your decision, set a monthly calendar reminder to ask yourself if you should adjust the percentage.
  • All code is not equal. I was talking to a CTO last week who said one of the biggest mistakes he’s ever made is thinking “Since I can only code 10% of the time, I’ll make sure it REALLY counts. I’ll contribute to the MOST IMPORTANT piece of the code.” As a result, he was consistently the bottleneck for the critical path through the system.

Habit #3: Foster Trust

Trusting others is the foundation of this. But it’s more than that. Successful CTOs FOSTER trust by creating a culture of trust.

As it turns out, there are four distinct elements of trust, as I learned from Doug Sundheim years ago. Only one of the four elements have to be low in order for trust to feel low. Here are the 4 elements. Next time you feel you don’t fully trust someone, ask yourself if one of these four elements is the reason:

CTO Trait Assessment Chart Success

Take it upon yourself to treat trust and integrity high on your values list. You’ll be glad you did.

Habit #4: Delegate Effectively

Being able to delegate effectively is one of these things we all KNOW we should do it. It’s just moving from KNOWING to DOING, and putting it into practice that’s the hurdle here.

Start from a place of knowing what is your Great Work (read Do More Great Work for amazing exercises on how to identify your Great Work)

  • Ask yourself - What am I most passionate about and most skilled at. Of these thing, which are the most valuable to my team and company today.
  • Highly Successful CTOsThen, work like hell to delegate as much of everything else as possible so that you can spend time doing these things. If you spend most of your day at the intersection of Passion, Skill and Value you can be assured you are doing great work for both you and your company.Pro tip:
  • When hiring, figure out which things are valuable to your company that none of your current team members are passionate about AND skilled at. This is a great way to identify gaps in your current team and help you hire to fill these gaps.

Habit #5: Manage Up

This is easily the most missed habit of all seven. I soooo often seen CTOs that are great at managing their team and awful at managing their boss. Or better yet, don’t even know who their boss is.

What does it mean to manage up? Know what your boss expects of you and communicate on your progress toward those expectations regularly.

An example is Lisa, Stride’s VP of Engineering. She and I meet every week. She has a 90 day plan. We both know what the plan is. We don’t discuss minutia weekly. Instead I ask her “What obstacles can I help you remove? Are you still on track?” And she asks me “What can I be doing better? What am I doing well?”

She tells me her progress; I don’t have to ask. She owns the responsibility of managing up, of telling me what progress she’s making.

It is your responsibility to know what your boss expects of you, and then to continuously show progress towards these expectations. It is your boss’s responsibility to help you understand how your expectations fit in with the bigger picture, and to remove obstacles so that you can do your job.

Pro Tip:

  • Don’t know who your boss is? Fix this problem first. How? Ask yourself: “Who can fire me?” This person is likely your boss.

Habit #6: Set expectations & Measure progress

Just like you should know who your boss is, you should know exactly who works for you and set expectations with those folks. Read 3 Signs of a Miserable Job to help learn how to effectively set expectations and measure team progress.

Then, sit down each direct report one-on-one and ask “What would be a good way for you to measure if you are doing a good job?” These things should be:

  • Things that are within their control
  • Self measured by the employee and reported to you
  • Self defined by the employee how and how often to measure

This conveys a sense of control and empowerment which is very rewarding. Then, it is on you to check in regularly and measure progress.

Habit #7: Give timely feedback

Give feedback and reward behavior for things that align with your company values. At Stride, our core values are Integrity, Autonomy and Collaboration. We are continuously rewarding behavior aligned with these values. We have:

  • Monthly huddles where we give “Shout Outs” to each other
  • A Victory channel on Slack that we use daily
  • Bi-weekly one-on-ones

We also hire, promote and fire based on these values.

Speaking of firing, don’t shy away from giving negative feedback. And don’t be afraid to fire people. When giving feedback, there are a few rules to remember:

  • Use “and” not “but” whenever possible. It’s amazing how changing this one word makes such a big difference.
  • Only say things that people can do something about.
  • Be prepared to be wrong.

Whether you’ve been a CTO for 1 year or 20, there’s always room for improvement. Keep these seven behaviors at the forefront of your mind and my hope for you is they will guide you along your journey.


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About Debbie Madden

Debbie has over 20 years of experience in NYC tech. She is passionate about helping businesses improve through software. As CEO, Debbie has unparalleled leadership experience in the technology space - she built 4 companies from the ground up prior to co-founding Stride.

With a reputation as a passionate woman executive in technology, Debbie is a sought after writer and speaker. She has appeared in popular media outlets such as Harvard Business Review, Huffington Post, Forbes and The Wall Street Journal.

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