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What Are The Top 5 Questions For Startup Mentors?

Chantelle Argent
26 November 2020

Getting the best advice from your startup mentor is about asking the right questions. Every second with your mentor is an opportunity for growth and development, so it is important that you don’t waste this precious time!

Here are the top 5 questions you should ask to maximise your startup mentoring session…

What experience provided you with the biggest learning curve?

This is a great question to ask your startup mentor, especially in the early stages. Mentors are usually great talkers and will enjoy sharing snippets of their own experiences as a way of helping you.

Invite these anecdotes, and really get to know your startup mentor. You have the best chance of successful communication in your mentoring sessions if the ice is broken and you feel that you understand one another.

This questions also encourages your mentor to revisit the testing times that they faced when starting their own business. This could provide key insights that you can then apply to your own startup. You get to reap the benefits of the lesson without having to make the same mistake!

What would you do in this scenario?

A session with your startup mentor can often feel like it goes by in the blink of an eye. There are so many questions to ask, and so much information to be gleaned. Sometimes, the best thing to do is to get straight to the heart of an issue you are facing.

Don’t be afraid to ask your startup mentor to step into your shoes. Ask the mentor what they would do if they were you in a given situation. This allows you and your mentor to begin tackling the tricky areas within your startup business head-on, and leads to practical, tailored advice.


What are your tricks of the trade?

Your startup mentor has likely been in the industry for many years or has had success in growing a startup into a fully-fledged business. Over this time, they will have developed a knack for certain recurring situations.

As a startup business owner, you may still be getting to grips with the things that your mentor now views as second nature - So be sure to tap into all their savvy shortcuts and entrepreneurial cheat-codes!

Your aim is to find out what the most useful startup hacks are. The future of your business is likely to involve a lot of wasted time, missed opportunities, and needless effort without asking questions like this.

What do you think my blind spot is?

This is an important one.

As a statup business owner, you have so much going on that there is often very little time to reflect on what you might be overlooking. It's also easy to become overly protective over your business in the early stages, and criticism can be hard to take.

This leaves you trying to justify every decision you make, with very little room to assess where you might be falling short. Here's where your startup mentor can offer some invaluable insight.

A startup mentor will be able to recognise things that you don’t yet see in yourself or your own business. You might even be making the same mistakes that they were blindly making when they were starting out.

Instead of getting defensive when your mentor points out your weaknesses, you should proactively seek out this feedback. This will, at the very least, allow you to pause for a moment of self-reflection; Or it could open up a dialogue that ultimately sets you on a path to become the best possible version of yourself.

Is there anyone else I should talk to?

No single startup mentor is a one-stop shop to the business hall-of-fame. Every individual has their own unique set of skills and experiences to complement the many different aspects of your startup.

There is nothing to say that you should stop at one mentor, or that you should only have one at a time.

Startup mentors are often well-connected people with an extensive list of industry contacts. Make the most of this opportunity to expand your network. The best startup mentors will tell you, you are never done learning.

Got some questions you want answering? Wiseup offers a carefully curated network of over 100 mentors who have the answers. Browse here today to begin your mentoring journey.
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