Mentoring for tech leaders. Why bother?

Tips to get the most out of professional mentoring.

Firstly, why bother?

For the last 15 years we’ve consistently heard our clients talk about some or all of the following outcomes from mentoring. Mentoring though, is not for the faint-hearted. Committing to mentoring is a long-term play, and one which requires planning and diligence – like most worthwhile things in life.

  • Learn more quickly by leveraging others’ experience – both the successes and the failures.
  • Accelerate your career progression by standing out – in a good way.
  • Improve your confidence and sense of empowerment in the workplace, because you’ve done the work to make sure you don’t have to “think on your feet”.
  • Improve the clarity and crispness of your communications with peers, staff & managers by taking advantage of the independence of a trusted and private sounding board who allows you to rehearse your thinking and message.
  • Improve your ability to envisage – and negotiate – a wider range of scenarios when needing to convince, direct, or influence by actively exploring the scenarios that you and your mentor jointly imagine.
  • Gain a clearer insight into what really matters to you in the workplace, then get on with creating an environment in which to thrive.
How to make it work?


  • Don’t just settle for anyone as a mentor. You need to respect your mentor from the outset and find it easy to establish a rapport, so take the time to get to know your options.
  • Don’t put off your mentoring sessions when time pressure is fierce. It is often at these times that your mentoring relationship will deliver the greatest value.
  • If you’re thinking of providing Agile Scrum mentoring, don’t fall into the trap of thinking that scrum master is the ideal mentor for every team member. The benefits of external input, distance and the freedom to open up about the real issues can far outweigh the innate value that the scrum master’s contextual understanding brings. An ideal mentor will share agile experience and ideas from a broader industry context when transferring agile knowledge to team members.


  • Work with your mentor to prepare a “charter” of outcomes for your mentoring relationship. Then set timelines for achieving them so you can stay focussed on those outcomes until you achieve them.
  • Block out and commit to preparing for and attending sessions with your mentor.
  • Stay in touch with your mentor on an ad-hoc basis in between mentoring sessions, sharing insights, asking questions and updating each other on progress.
  • Be prepared to acknowledge there always more to learn – even if you’re already an expert.
  • Bring complex questions/situations to your sessions and be prepared to step out of your comfort zone to “role play” those situations. Try playing the role of various individuals in the scenarios.
  • Be honest with yourself. Be harsh enough to be truthful and realistic, but gentle enough to give yourself permission to fail from time to time.
  • Be playful and curious. It’s a serious journey, but it should also be a lot of fun!

To provide a little extra context, here are just two of the mentoring assignments that I have personally delivered over the years to good effect.

  • I have worked alongside executive directors (“EDs”) who, by definition, need to manage both the operational (ie. “executive”) and strategic (ie. “director”) aspects of this challenging composite role. My approach has been first to develop a clear statement of what the ED needed to deliver for the organisation to be successful, both strategically and operationally. Thereafter, we co-developed a range of customised tools/techniques that would both deliver on the ED’s responsibilities as well as match the particular individual’s personal style and strengths. This was explored and tested through a series of private role plays and scenario planning workshops over a period of many months.
  • In working with senior program managers in a software delivery company, I have provided a combination of challenge (ie. anticipating the scrutiny they will receive from their manager) and support (questioning and suggesting alternate ways of managing the people, programs and data under their control) with the dual goals of reducing risk for the programs they manage and speeding up their personal / professional development.

Mentoring relationships can be extremely powerful. 33% of business creators with an entrepreneurial mentor became top performers; more than three times better than others in this New York-based study of tech companies. Similar results are evident for tech leaders such as system architects and engineering managers.

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