4th May 2022

Five reasons why Obi Wan was a terrible mentor

We all know the story. Jedi Master (Obi Wan) agrees to mentor Padawan apprentice (Anakin Skywalker) whilst training him to be a Jedi Knight. Mentee is seduced by the Dark Side. Mentee decides that he wants to rule the Galaxy. Mentee takes on mentor in winner-takes-all light sabre battle. Mentor emerges the victor, leaving his mentee to die. (Mentee later decides that he still wants to rule galaxy but that’s a whole different set of films)

Most blame Supreme Chancellor Palpatine for Anakin’s lure to the Dark Side.

Others blame Padme.

Personally, I blame Obi Wan. He was a truly terrible mentor.

And here are my five reasons why.

  • Lack of integrity: Throughout his training, Obi Wan labours the merits and integrity of the Jedi to his eager mentee. Jedis never give in to feelings of anger. Jedis never give in to feelings of fear. Jedis never tell lies … blah, blah, blah. However, during the course of this mentorship, Obi Wan instructs his mentee to spy on the Supreme Chancellor on behalf of the Jedi Council. Did this instruction demonstrate integrity? Not in my view. A mentor should demonstrate integrity at all times to a mentee and, as a mentor, Obi Wan failed in this respect.
  • Lack of challenge: The role of mentor involves a degree of objective scrutiny. A mentor should be able to constructively challenge his mentee about any issues which are discussed between them. Obi Wan fails on each occasion to do this. But let’s face it – this is not a surprise. Obi Wan’s inability to process information about anyone other than himself should have been obvious to all of us, given his complete failure to recognise that the Supreme Chancellor was in fact the Sith Lord! It couldn’t have been more obvious, had it been tattooed on his face. A mentor requires to listen, guide and, where appropriate, criticise constructively. Help me, Obi Wan Kenobi. I am losing hope in your abilities as a mentor.
  • Dishonesty: Acting as a mentor involves complete honesty, with the occasional degree of diplomacy. However even when Obi Wan gets a second chance at mentoring Luke Skywalker, he fails to disclose various essential truths to him. Yes, he tells Luke how evil Vader was. Yes, he tells Luke that Vader “betrayed and murdered” his father. However, he fails to get round to telling Luke that Vader is his actual father! There should be 100% trust and honesty between a mentor and mentee and, again, Obi Wan falls down in this respect.
  • Hypocritical: A mentor requires to be admirable and accessible. In my view, Obi Wan completely lacks these qualities and, at times, verges on being hypocritical and remote. Do we remember him telling Anakin that, at the age of nine, he was too old to begin Jedi training? Why then does Obi Wan wait for nineteen years before commencing Luke’s training? What a hypocrite. And what was he playing at living like a hermit in these caves whilst Luke was growing up. As a mentor, the door should always have been open to the mentee. Game over, Obi Wan. Game over.
  • Uninspiring: Let’s face it. Obi Wan is uninspiring. His style of mentoring involves lecturing and patronising his mentee. Moulding does not mean scolding.  Instead of lecturing him on his arrogance or recording the frequent incidents of insubordination in his calendar, he should have perhaps spent some quality time with him. A mentor and mentee should aim to do fun things together, as well as the more serious side of the mentoring. You should have shared a Jawa Juice with him, Obi Wan. Or at least taken him to an ice hockey match.

As an employer, if you encourage a mentoring programme in the workplace, you should ensure that this mentoring scheme is worthwhile. All too often, an employer will set up a mentoring arrangement and then fail to give too much attention to the benefits (or not) of it. Such a scheme should be of benefit to both the mentee and the employer. In the words of Yoda, “Do. Or do not. There is no try.”

So if you are involved in a mentor scheme, either as a mentor or a mentee, you would be wise to remember what happened a long, long time ago, in a galaxy far, far away, with particular reference to Obi Wan’s failings as a mentor. In fact, forget about Obi Wan and Anakin Skywalker. And look instead at Chewbacca. He turned out OK. As a mentor, why not style yourself on Han Solo instead? (Or, if you’ve seen the most recent set of films, Han YOLO)

Obi Wan, this is not the mentor we’re looking for….

Good luck. And may the Force be with you.

If you need any employment law advice, please get in touch with Blackadders’ Employment Law team working in Aberdeen, Dundee, Edinburgh, Glasgow, Perth and across Scotland.

Simon Allison - employment law partner

Simon Allison, Partner
Accredited by the Law Society of Scotland as a Specialist in Employment Law
Winner of the ‘Lawyer of the Year Award’ at the 2018 Scottish Legal Awards


The opinions expressed in this site are of the author(s) only and do not necessarily represent the opinions of Blackadders LLP.

Blackadders takes all reasonable steps to ensure that the content of this site is accurate and up to date. The site is not, however, intended as a substitute for seeking legal or other professional advice but rather as an informative guide to the services provided by Blackadders and topical legal developments. Site visitors should always seek advice tailored to their specific situation. Consequently, Blackadders accepts no responsibility for any loss or damage suffered by anyone acting or failing to act on the basis of information contained on this site. Downloading of material contained on this site is at the user’s own risk and all necessary virus checks must first be carried out by the user. Blackadders is not responsible for the material found on any web sites linked to this one and links to this site may only be made with Blackadders prior consent.


Blackadders owns the copyright in this blog and all material contained on it. The material on this site may be downloaded for personal use only and must not be altered. Otherwise, Blackadders’ written consent is required before any material on this site is reproduced, copied or transmitted in any way.

Privacy Statement

Information passed to us via this site is kept confidential and will not be disclosed to third parties except if authorised by you or required by law.

© Blackadders LLP 2022

Members of the Law Society of Scotland.

Blackadders Solicitors is a trading name of Blackadders LLP, a limited liability partnership, registered in Scotland No SO301600 whose registered office is 30 & 34 Reform Street, Dundee, DD1 1RJ. Reference to a ‘partner’ is to a member of Blackadders LLP.

Back to Business Legal News from Blackadders Solicitors