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A lot has been written on the subject of management vs leadership when it comes to guiding teams. I’ve heard it argued that great executives lead whereas poor executives manage. I think they are two very different things, and you have to do both well to succeed.

The idea of managing people should not always imply micromanagement. Like nearly every other executive skill there are both strategic and tactical aspects of people management, and different levels of involvement ranging from deeply immersing yourself in a team member’s day-to-day to only framing success conditions for a project or role.

When I think of what management means as opposed to leadership, I think of setting constraints. There is a perceptive that setting constraints on mature, professional people is a waste of their abilities or even insulting, but I believe quite the opposite: failing to set constraints, or to put it another way, expectations, reduces the likelihood that people will find their way to success and makes it harder for them to succeed.

People know how to do their jobs better than you do (hopefully) but they don’t necessarily know what the broader group, or the rest of the organization, or the CEO, or the board, or your users, or the market really needs from them. It’s up to you to manage these expectations by setting very clear success criteria whenever possible, and to manage their paths to meeting those expectations by course correcting early and often if they begin to drift off course, because though everyone on the team should have the ability  to succeed on their own, almost no one will have the perspective to know how they’re doing at all times.


There are four kinds of investors:

Those that know your business and know that they know your business. They are sources of wisdom. Use them.

Those that know your business but act as if they do not know your business by being hands-off. They are sleeping partnerships. Awaken them and extract value.

Those that do not know your business and know that they do not know your business so are hands-off. They are helpful in other ways and can be great support.

Those that do not know your business and do not know that they do not know your business. They will impose their will upon the business and destroy value. Shun them.

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Build vs Buy

We are often faced with a dilemma when considering how to use software to solve a problem: whether to build the solution to that problem, or whether to buy a product or service that we believe can solve it. Many people and groups struggle with this choice, and also struggle to find a reliable method for making well thought out decisions. 

Every situation is different but as a rough guide I’ve found it useful to ask 5 directional questions:

  1. Is there an adequate solution that you can buy?
    • You can integrate it
    • It fits timing needs
    • It has features you need now
    • It has features you’ll need later or can be modified
    • It is reliable
    • There is support available
  2. Is this a key differentiator for your business?
  3. Is there an industry standard solution that you can buy?
  4. Can you build it adequately for less than the cost of buying it?
  5. Do you have other projects that would be a better use of your time?

Often, this is how those questions guide the way to an answer:

Product Creating vs Operational CTOs

I’ve heard CTOs described as Product-focused versus Tech-focused, and I’ve heard people described as strategic versus operational, but I wonder if these are false dichotomies. I wonder if a better scale may be Product vs Operational — or to put it another way — CTOs that excel more at considering what to build versus CTOs that excel more at considering how to help many different people build it.  

Executives at either end of that spectrum can be strategic or tactical at different times. It’s a common misconception that operational CTOs are weak strategically, when in fact it seems impossible to implement long-term vision of operational excellence without having a strategy to guide decision-making. Likewise it’s a common misconception that Product-focused CTOs are weak technically. Some of the most gifted Product people I’ve known were also very strong implementers. 

However, I’ve known hundreds of CTOs and I don’t think I’ve ever found a strong Product-focused CTO who also excelled operationally at scale, and likewise I don’t think I’ve ever known a strong operational executive who excelled in Product creation. I’ve known many people who have done both, but in all cases they were either excellent at only one of them or neither.  


There is a difference between being good at the CTO job and being good at the CTO role. 

The job is everything that is required to deliver real results: hiring great people, building great software, buying the right things, defining strategy and doing everything it takes to execute on that strategy accurately.

The role is the perception of the job you’re doing; how well you play the part.  

It is much harder to learn how to excel at the role than it is to learn how to excel at the job. Expectations can change via conversations that happen in conference rooms you’ve never been to, involving people you’ll never meet, who discuss questions and decisions that will never be communicated to you. The CTO role is not a game played with complete information.

Despite that, it is important that we do everything we can to create and fulfill roles that we feel are right for the organization. Sometimes that means forcefully arguing for change, other times diplomatically finding compromise. Sometimes it means spending more time interfacing externally, and sometimes it means putting in extra face time internally. It involves finding the right balance between different stakeholders’ ideas of what the company needs, which are very often mutually exclusive.

Recovering from Mistakes

One gauge of how good someone is at their job is how well they recover from mistakes. You can tell how great of a guitar player Neil Young is by seeing how well he recovers from a misplayed note in a solo — somehow, he actually makes it sound good. Likewise, chess grandmasters are excellent at making their mistakes as difficult as possible for their opponents to exploit and so turn many losses into draws.

In our jobs we often make mistakes when it comes to project management, hiring, putting the wrong people into a big role, politics, architecture, and so many other things. Being able to quickly realize that a mistake has been made, and somehow having the mental fortitude to leave the past behind and re-approach the current situation with a fresh perspective is what sets apart amateurs from professionals.  

CTO Skills

Which skills are really necessary to excel as a Chief Technology Officer?
What enables one CTO to perform better than another in a given situation or role?
When looking to improve, how do you know what to focus on?
What does it really take to do this job?

I believe that skill as a CTO is an amalgamation of several dozen discrete skills, each of which can be strengthened independently, and the relative value of which varies from role to role.

Team Building Skills

  • Recruiting
    • Attract, hire, retain the best people
  • Staffing
    • Having the right people and matching them to the right roles are two different things
  • Team Organization
  • Evaluating People
  • Firing

Organization Skills

  • Time Management
  • Project Management

People Skills

  • Leadership
  • Motivation
  • Diplomacy
  • Advocacy
    • Getting stuff approved
    • Getting stuff killed
  • Therapy
    • Supporting people up, down, and across the org
  • Emotional Control
  • Empathy
  • Negotiation
  • Mentoring
  • Teaching
  • Crucial Conversations
  • Bullshit Detection

Communication Skills

  • Speaking
    • Sub-Skill: Communicate via phone
    • Sub-Skill: Communicate via video
  • Writing
    • Sub-Skill: Effectively use email
    • Sub-Skill: Communicate via text chat
  • Reading
  • Listening
  • Presenting
  • Documentation

Technical Skills

  • These vary greatly depending on the role

Creative Skills

  • Product Management
  • Strategic Planning
  • Tactical Execution
  • Innovation
    • Awareness, understanding, and experience with cutting edge technologies and solutions
  • Ideation
  • Questioning the ordinary
  • Being resourceful

Mental Acuity

  • Energy
  • Acting quickly
  • Judgment
  • Confidence in forming opinions
  • Making and committing to decisions
  • Situational Analysis
    • How big of a mess are you in?
    • How can you improve your position?

Financial Skills

  • Budgeting
  • Accounting
  • Valuation
    • Every executive should at least understand options and intrinsic value.

Facilitation Skills

  • Build vs Buy
  • Vendor Management
  • Industry Knowledge