Frequently Asked Questions about CTO Coaching and Mentoring

Depending on the client and their needs, we typically meet more often early on and adjust our cadence as we progress. Typically every 2-3 weeks to start to help get going quickly, and then every 3-4 after a couple of months.

Most clients find that 90 minutes is a good session. It is good practice to block 15-20 minutes before each session to gather your thoughts and set a clear intention for our time. Similarly, having some time after the session to lock in the key points and set yourself up to translate the talk into action is essential.

Call me old school, but, I like to meet in person. However, that isn’t always practical or possible. Even my clients in Melbourne, where I live, frequently ask to meet by Zoom due to scheduling constraints. As a result, we will use Zoom as required.

Many of my clients are not located in Melbourne. In that case, I try to arrange some of our key sessions in person, especially early in our engagement. Otherwise, we meet on Zoom, which can be highly effective for most sessions.

I generally structure CTO coaching engagements on a set fee basis. My assumption is that we will have regular sessions, but there will be times when we need to meet more often. In that case, we can catch up on the phone or via video between regular meetings. I am here to support your development and growth.

Most engagements last 6 months, long enough to see material improvements. Many clients extend for an additional 6 months, and I am generally happy to do so.

Yes! There will be homework. It is generally not very time-consuming but critical to development. Sometimes, it’s reading; other times, it's setting aside time for self-reflection. I will send “Reflections and Reminders” session notes to prompt follow-through. 

I only work with six clients at a time. I am frequently asked why I do this. There are a couple of reasons.

1. I love coaching and mentoring tech leaders. However, I find that I enjoy it less if I have to many clients going, for reasons I’ll discuss below.

2. I want to ensure I have the time and space to give each client my full attention and support in achieving their specific leadership goals.

3. Every engagement is bespoke; frankly, that takes more time than running a “coaching mill”.

4. I’m at a point in my life that I take my fun seriously. Having more than six clients limits my ability to do things I want to do. That includes travelling, ski adventuring, mountain biking, and hiking.

5. If I want to make more money, it’s more efficient to just return to full-time work.

I'll tell you if I am currently at my limit, and we can agree on a start date.

While the employer generally engages me and pays for the engagement, I work for the client to help them transform their leadership and deliver excellent outcomes for the organisation. Our ability to accomplish this rests on trust. As such, our coaching is confidential. I do not discuss the content of our discussion with anyone other than the person I am working with.

I work within the code of conduct set by the International Coaching Federation, which includes confidentiality. Companies agree in the contract to respect this.

In almost every case, the organisation engages and pays the coach. However, most CTOs only receive coaching if they identify the need and propose the idea. The client almost always asks the company for coaching and finds the coach they want to work with. We can talk this through.

Before engaging a CTO coach, it’s important to meet with a couple of people to better understand what you need/want. Most coaches offer a free 30-minute “getting to know you” session.

Questions

Once you decide to work with me, I will give you a proposal for our engagement. In most cases, your leader or HR leader will approve it.

I can walk you through this process. It’s typically pretty straightforward, as most CEOs and HR will have worked with coaches before.

To get started, text me at (0438)003-619, and we’ll set up a 30-minute meeting to discuss how I can help you achieve your leadership potential.