This is part of the weekly ‘Ask Tristan’ series. If you have a question, please email me: [email protected]


Q: Dear Tristan, I am the owner of a small business that has grown considerably in the last 18 months.  Since starting the business 5 years ago I’ve had a mentor who has been with me every step of the way. But, I think she might now be holding me back.  When I’ve got great new ideas, she always asks questions that stop me in my tracks.  I’m not sure we are aligned to the same future any more.  What should I do? - WK

A: Dear WK,

Firstly, congrats on starting a business and growing it over 5 years, that’s a fantastic achievement!

Now, regarding this mentor, they’re supposed to ask the hard questions!  Some of the best mentors I’ve had have both supported and challenged me.  As entrepreneurs, we think of ideas that could create huge value everyday.  However, only a few of these ideas are any good!  It’s the less entrepreneurial people that we need to stress-test these ideas, ask questions and potentially poke holes in them.  The best ideas survive this testing and are the ones we should pursue (most of the time, sometimes it’s worth some risk on a crazy idea!).

By the same token, I’ve found that most mentor-mentee relationships often have a use-by date.  You’ve been with your mentor for 5 years, in that time you and your business will have both grown and changed a lot.  Has your mentor grown too?  If not, perhaps you need to consider someone new that has been where you are going?

My advice: have an honest conversation with your mentor about how she sees the future of your business.  If you are not on the same page anymore, it’s best you both realise this and respectfully part company.  Perhaps she actually wants to leave and will be relieved when you suggest different directions?

Whatever the outcome, make sure your mentor knows how grateful you are for all of their help and support.  If you couldn’t have done it without her help, make sure she knows it!

Good luck,