Mentoring is incredibly important for anyone navigating their career and wanting to succeed, and as discussed in an earlier post, the benefits for new tech leads are numerous. But, rather than simply guiding ‘juniors’ through various stages of their career, transformational mentoring — through mentoring circles, coaching and peer support — is a way of giving and receiving so much more.

At CTO Craft we’ve made it our mission to bring together incredibly experienced and knowledgeable tech leaders, covering everything from engineering culture, hiring and motivation, stress management to tech strategy planning and put them in one accessible place. Because when you’re in a startup and spending all day every day building MVPs or scouring the market to source talented developers as you scale, you often don’t have the time to network properly or seek out an appropriate mentor. Without access to a formal process (like those often provided by larger companies), sometimes it’s hard to know where to look if you’re a new tech lead who’s so far learned on the job. Even if you do find someone, just because a person has been there, done that, it doesn’t mean they know the best ways to teach other people — and this is where mentoring circles come in.

What is a mentoring circle?

We offer the opportunity for emerging CTOs and technology leaders to meet on a weekly basis for one hour over the course of three months. Facilitated by one of our experienced CTO coaches, such as Douglas Squirrel, the sessions use role play, industry standard tools and mental models for bolstering decision making, team motivation and communication, and help build skills around leadership, process and planning. Limited to a working group of three to five people, you’ll get the chance to share your experience, discuss hurdles faced in the workplace and help solve your own and others’ problems. Covered by the Chatham House Rule, you can also rest assured that what goes on in the group, stays in the group.

The CTO Craft mentoring circles are guided and structured in such a way that both common and isolated issues can be worked through with peers, who can offer advice both during the meetings and afterwards through designated Slack channels. Whether you’re concerned about talent acquisition and retention, managing a team or scaling a business, all engineering managers and CTOs from the most experienced to those just starting out, will learn invaluable skills and have the opportunity to form lasting relationships.

What are the benefits?

They say a problem shared is a problem halved / we’re all in this together / there’s no ‘I’ in team — and it’s true. Often in startups, you can feel alone, overwhelmed and like you’re failing, even when you’re not. Sharing your experiences and problems with people who are (or have been) in similar situations is vital to feeling like you can cope and in fact, push forward. Being able to talk freely and openly with peers you both respect and trust, assists learning, contextualises issues and helps deliver resolutions. Plus, having a seasoned expert steering the sessions can help with visualising long-term goals, and ensuring team growth and product development aligns with them.

And that’s not all. Dealing with hardships together forms bonds so, in addition to gaining knowledge, insight and mentoring, be prepared because you’ll also gain friends.

Why join our circles?

If we haven’t yet convinced you that this is the right thing for you, just check out what our former attendees said they loved about it:

“Varied style e.g. discussions, lectures, active involvement, role play. Made the sessions engaging and something I looked forward to.”— A.K.

“The circle was an amazing experience. Not only was Squirrel a great coach but hearing from other CTOs with similar challenges at different stages was equally as valuable. I feel a lot more equipped to manage as the company grows and changes.”— T.H.

“Creating specific, actionable solutions to existing problems.” — J.R.

Just remember as Helen Keller once said: ‘Walking with a friend in the dark is better than walking alone in the light.’ We’re ready, we’re waiting, and we have the lights.

Find out about fees, how to sign up and more on the CTO Craft website or email and we’ll be in touch shortly.

If you, or your CTO / technology lead would benefit from any of the services offered by the CTO Craft community, visit: or contact us via email at:

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