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7 Habits of Highly Successful CTOs

Debbie Madden
May 18, 2015

It’s Monday morning at 10:30 a.m. 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 have all the 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 to resolve such questions fast, and to get key insights into seven habits of highly successful CTOs, read on.

I’ve been working with CTOs for more than 20 years. Over those years, I’ve seen seven distinct habits 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 toward helping you achieve success in your career. Today, I’m going to share with you the secrets behind doing that.

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

The seven 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 and measure progress

Habit #7: Give timely feedback

Habit #1: Make high-quality decisions quickly

We’ve all been there with Jon. Whether you’ve had to make the call on migrating your tech stack, breaking out your monolith, or firing an employee, CTOs are faced with difficult, high-impact 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 processes 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 make 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 skill for a CTO is knowing when to code.

I know CTOs who code 100% of the time, and CTOs who 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 on Monday morning and say “Hmmm, I wonder if I should code today.”

Pro tips:

  • The amount you code will and should change over time. If you are a CTO of a three-person dev team, you might start out coding 70% of the time. If you grow into a 20-person team, you might 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 whether you should adjust the percentage.
  • All code is not equal. I was talking with 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.


Learn More:
Effective Team Communication Builds 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 has to be lacking in order for trust to feel low. Here are the four elements. Next time you feel you don’t fully trust someone, ask yourself if one of these four elements is the reason:

Type of trust Assessment
Competence Does this person have the skills needed? Is they say they are a senior Ruby on Rails developer, are they?
Reliability Do they do what they say they will? If I hire a remote developer who says they are working full-time, are they truly putting in 40 hours per week?
Motive Are the person’s motives in line with yours and the business’s?
Openness Is this person honest with others?

Take it upon yourself to place 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 the things we all know we should do. 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 the book 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 things, which are the most valuable to my team and company today?”
  • Venn diagram of Passion, Skill, and Value—three circles equally overlappingThen, 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 who are great at managing their team and awful at managing their boss—or better yet, who 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 minutiae 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 toward those 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? If not, fix this problem first. How? Ask yourself, “Who can fire me?” This person is likely your boss.

Habit #6: Set expectations and measure progress

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

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

  • things that are within their control;
  • self-measured by the employee and reported to you;
  • self-defined by the employee in 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;
  • biweekly 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 one 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 that they will guide you along your journey.


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