Your first 90 days as CTO (article summary)

A summary of Your first 90 days as CTO by Will Lethain.

  • Definitions of CTO and VP of Engineering differ across companies.
  • Priorities for a brand new CTO vary; different priorities for a startup versus a mature company.

Priorities and goals

To figure them out Will defined some questions to ask yourself:

  • How does the business work? (sources of income; spendings, business domain nuances)
  • What defines company cultures? (are there true values defined? who is valued and what for?)
  • How to build healthy relationships with peers and stakeholder? (how to earn their trust)
  • How does engineering team work? (processes)
  • Is technical quality high? (do the team uses/has access to proper tools, does technology limits them somehow?)
  • Team morales (what motivates the team? are there leaders? who is unhappy and why?)
  • Pace (how to make you and the team motivated and energized for a longer period?)

Set measurable goals for each of priorities and track them over time. Find good tools and practises (like skip-levels) to help you.

You need to understand the organization and systems very well before making the right changes. As a senior leader, your role is to implement durable improvements. At the same time, you cannot introduce a lot of them at the same time. It is easy to lose trust and feedback.

The three top onboarding issues defined by Will are:

  1. Introducing changes before fully understanding a problem.
  2. Judging without context.
  3. Referring to previous jobs (with a totally different context).

Tasks for the first 90 days

If you find something that urgently needs to be corrected, go ahead and try to fix it. At the same time, do not spend all the time on it. You are responsible for both short and long-term success. The bigger company the more time you will need to understand its complexity well.

Learning and building trust

Learn as much as possible.

  1. Ask the CEO or CTO about explicit expectations.
  2. Figure out if something needs to be addressed immediately.
  3. Try to meet everybody in person (individual and group meetings).
  4. Setup recurring one-on-ones and skip-levels.
  5. Share your feedback.
  6. Observe how meetings are conducted, especially the ones you are supposed to lead soon.
  7. Listen to the company’s customers (by e.g. login into CRM system or attending user testing meetings).
  8. Find a business analytics system and learn how to use it.

Support system

  1. Find a support group of people in similar roles.
  2. Find a coach.
  3. Take care of yourself (sleep & psychical exercise).

Organizational health and process

You can’t change organizational processes in one day. It’s your responsibility to find gaps and address them, though.

  1. Document existing processes.
  2. Implement one or two changes at most.
  3. Plan growth for next year (including missing critical roles)
  4. Set communication pathways (monthly team meetings, weekly updates etc.)
  5. Pay attention to non-engineering roles.
  6. Remember about people working outside the office.
  7. Do compensation review.


  1. Attend existing interviews, onboarding and closing calls (your presence in a room will have an impact).
  2. Identify key missing roles.
  3. Track hiring funnel metrics and hiring pipeline.
  4. Organize a recurring meeting about recruiting to constantly improve the process.
  5. Attend closing calls for high priority candidates.
  6. Build a brand around engineering (blog/conferences/Twitter).


  1. Do not disrupt the current execution before you have a working alternative. Measure and iterate instead.
  2. Find out what is working and scales.
  3. Define internal measures of engineering velocity.
  4. Define an external measure of velocity (impact on business).
  5. Consider adding a small amount of process and controls.


Even though engaging in major technology changes usually does not happen in the first 90 days, you should start some activities.

  1. Try to find out if the existing technology is effective?
  2. How are high-impact technical decisions made?
  3. Make a trivial change and deploy it to production.
  4. Do an on-call rotation.
  5. Attend incident review.
  6. Record technology history.
  7. Document the existing technology strategy.
  8. Avoid having too many lightly-held opinions.

My review

An excellent article with an actionable list of tips on how to start a new job as a senior executive.  Even though I am not one, I will make usage of some of them.


Igor Springer

I build web apps. From time to time I put my thoughts on paper. I hope that some of them will be valuable for you. To teach is to learn twice.


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