Leadership Coaching

For a healthy team culture to thrive, you need both top-down support and bottom-up support. Team Workshops support bottom-up cultural change. Leadership Coaching supports top-down cultural change.

Employees need support to thrive. In modern tech, managers are expected to actively support their employees as professionals. Sometimes this works out and you have a great people-manager who supports your growth and cares about your happiness. This doesn’t always happen, but when it does it works out great for the employees at least!

Who supports people at the top? Who can a CTO talk to about CTO problems? When a CTO is too busy to be an active mentor (it’s common!), who can support technical leaders like engineering managers and product managers?

Ignore this situation and everyone loses out: you lose out as an individual, your company loses out by not having you stay and grow, your customer lose out by having less effective, engaged employees. Conversely, doing a great job at this has huge benefits: employee happiness, effectiveness, retention, easier hiring, and happier customers. It’s a shame any company misses out on these!

Without Support

employees languishing
stagnant growth
employees leaving
hard to recruit
worse project outcomes
unhappy clients/users

With Support

employees flourishing
constantly growing
employees staying
more employees joining
better project outcomes
happy clients/users

Where does anyone get professional support?

There are generally three approaches to getting one-on-one support as a professional: internal coaching, external coaching, and personal coaching.

Internal Coaching

your manager
a senior employee in your role

External Coaching

professional coach

hired by your company

Personal Coaching

professional coach

hired by you for yourself

Casey's Coaching

How can Casey help?

Internal Coaching

creating communities of practice
peer mentorship programs

External Coaching

direct coaching
coaching your coaches

Personal Coaching

coaching for you

Who is this for?

Casey coaches people in these positions and others. Casey has worked in many of these roles himself, directly.


Chief Technology Officer
VP/Head of Product
VP/Head of Engineering

Technical Leaders

Product Manager
Engineering Manager
Tech Lead

Coaching Goals

Together, we create goals and track them. We define these at beginning of the coaching relationship, and update them periodically. These help focus our efforts, making sure the coachee gets the most out of the engagement. Sometimes externally-set goals are a part of the process, but to be successful goals must be defined and agreed to by the coachee.

Here are some example goals for different roles.

Example Goals for a CTO

fostering a culture where employees can speak up
being aware of issues before they arise
being aware of issues before they arise

Example Goals for a Product Manager

deliberate, transparent prioritization
communicating effectively with stakeholders
working better with developers

Example Goals for an Architect

balance contributing and consulting
making people are aware of your contributions
approach for choosing a language/framework

Weekly One-on-ones

The bulk of coaching progress is made in weekly 60-minute one-on-one conversations. We talk through areas for professional growth, and strategize how the coachee can approach that growth. In these, we talk through current challenges and potential approaches to dealing with them. The process of talking through a problem with someone who really gets it is hard to overstate.

Engagement Duration

Engagements are done for 3 months at a time, which is 12 coaching sessions per coachee.

Get in touch

meet with Casey