Newsletter 34 : The Joy Of Mentoring

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The 5 Minute Tech Break :
The Joy of Mentoring

Happy Friday

We took a break last week. Your groaning inbox was saved further punishment as we found ourselves all over the place in pursuit of new product releases and sunshine.

But we can’t deprive you of the “5 Minute Tech Break”for too long so we’re back and it’s a focus on Mentoring because, we’ve seen a dramatic spike of interest in mentoring services and some great results emerging from some of the relationships being formed.

Otherwise, we’re pleased to announce that the new, exciting version of CTO Academy will be unveiled next week.  Watch this (and other) spaces.

Happy reading (and mentoring).

Andrew Weaver

Article : Tech Careers and Why You Need To Hug A Mentor

We launched our mentoring service in January 2019 and it’s been wonderful to talk with and help so many of the CTO Academy community, from one off calls to assist with some immediate crisis to longer term career and business development strategies.

It can sometimes be lonely at the top (and in getting to the top) so having an experienced mentor at hand is often an invaluable tool.

This article from Jason, is a personal perspective of the tech career journey and how/when mentors can best assist.

How to find a good mentor


Getting the right fit is so important, particularly with longer term mentoring relationships.

This is a nice infographic from which illustrates the different elements to what makes a “great mentor”


How To Fire A Bad Mentor

Conversely, if the fit doesn’t work then you need to get out quickly. No point burning your time and cash, with a relationship that isn’t working, for whatever reason.

A recent fast company articled explained that by having a mentor you’re more likely to get a promotion and/or stay with one organisation for at least five years.

But … not all mentors are good.

Major red flags that mark out a bad mentor;

1.  They don’t have a success record

Beware of those who find it easier to teach others, than make a success of themselves. The world of business coaches is festooned with such charlatans.

2.  They don’t have a clear mentoring system

A good mentor will be focused on deliverables, setting out goals be achieved within a fixed period of time. Incompetent and/or inexperienced ones will turn up for a chat.

3.  They aren’t holding you accountable

Not only do goals and deliverables set clear targets within the relationship, they help to hold you and the relationship accountable. That’s a primary task for the mentor. Otherwise, what is the point?

4.   They Don’t Walk Their Own Talk

Linked to (1) above and beware the mentor who likes to dish out advice they don’t or haven’t followed through themselves. Sure they can speculate a little, but you need to get the cut of their mentoring gib asap and discover if they’re all talk.

More on this theme available via the fast company article here.


Book of Week : Tribe of Mentors

Most of you are probably aware of Tim Ferris – man of the 4 hour week, diet and various other motivational tomes.

I confess I enjoy a bit of motivational Tim from time to time.

This book saw him turn the tables on giving advice and instead saw him seek advice from industry titans.

This boy has access, his list of ‘mentors’ is impressive so if you’re looking for non-tech inspiration, it’s not a bad place to start.


And finally … what do we look for in mentors?

We’re expanding our mentor network. 

This is some of what we look for.

1.    Real expertise

The business world appears awash with business coaches, marketing gurus and mentors who, when you scratch the surface of their CV, bring very little coal face expertise to the party. 

A classic journey to ‘expertise’ is to write a book, find an amazon niche, and update their linkedin profile with ‘best selling author’ and as night follows day, ’keynote speaker’.

With technical mentorship that’s a much more difficult trick to pull off but some try.

We look for genuine experts, with strong track records, and minimal fluff. 

2.    Wear that expertise lightly

They also need a humility and ease with what they know. Mentoring is a platform for the mentee to learn, not the mentor to dazzle.

3.    Be adaptable

Each mentee is different and each mentoring relationship is unique. 

Mentors need to be adaptable and have sufficient levels of emotional intelligence to understand what that mentee needs and what success will look like from that relationship.

4.    Managing expectations

True of most relationships, particularly so with a mentoring one. 

The initial getting to know process needs to involve some radical candor and an immediate willingness for honesty and transparency about what is possible.

Immediate management of expectations helps both parties understand the potential fit and minimises the risk of later surprises.

Establish early any non-negotiables, best times and forms of contact etc. 

5.    This is about people

Mentoring is ultimately about finding the right the people fit. About establishing a relationship of trust and openness. Without either element, it has nowhere to go. 

We look for mentors who have been successful leaders in the past and ‘get’ people.

6.    Never assume anything

We all do it. We all make assumptions.

Just looking through a linkedin profile can lead to assumptions being made about that career decisions, personality, ambition, potential.

Never go into a mentoring relationship assuming anything. 

7.    Be open, admit it’s a rocky path, mistakes get made

Being a tech leader or manager can be an isolated role and sometimes, the mentoring relationship is as much about providing the mentee with a sounding board and sense check that they’re not going bonkers!  

It’s therefore crucial that the mentor is open and candid about their own ups and downs, that not only provides reassurance that we all have them and “you’re not alone”, but also provides the mentee with the confidence to discuss and analyse any of their own mistakes.

8.    Give more, ask for less

Mentioned already but it is a core pillar of our selection and feedback process. This is always about the mentee. From start to finish.

9.    Introduce to network

Working with a CTO Academy mentor will normally give the mentee access and exposure to their wider network and the mentor will be expected wherever possible, to provide introductions where and how they think it will help the mentee.

We don’t operate in silos, our raison d’etre is to use all the tools in our arsenal to help our mentees and subscribers progress.

10.    Celebrate their achievements

The best mentoring relationships involve some significant emotional investment. The mentor can’t help but take the progress of their mentee very seriously and so success should be celebrated. We want to know and to hear about the achievements. 

It’s writ large in our mentor agreements, “always celebrate their achievements” … 

11.    Lead by example

Most of our mentors are heavily involved in their own projects, companies and investments. We want to see them leading by example, not preaching from a distance. It’s a journey for both. 

If you know someone who fits our mentoring bill, ask them to get in touch with [email protected]

Star Wars Quote Of The Week

“Mentors have a way of seeing more of our faults that we would like. It’s the only way we grow.” 

― George Lucas, Star Wars: Episode 2 Attack of the Clones



The next version of CTO Academy is due for release during the next few days and we will provide more information in next weeks newsletter.

Bags of new material coming through the pipeline and additional features.

In the meantime, have a wonderful, safe and giving weekend.
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