12 Questions to Ask a Business Mentor Before You Start

The best questions to ask a business mentor fall into three groups: what they have actually done, how they work with people like you, and what they honestly think of your plan. Asking all three before you commit tells you within one short session whether this person can help, and it sets the tone for a relationship built on specifics rather than pep talks. If you are still deciding whether a mentor is the right form of business advice online for your stage, the questions below will help you find out quickly.

Before you ask anything

Prepare a one-paragraph summary of your business: what you sell, to whom, current monthly revenue (even if it is zero), and the single decision you are stuck on. Send it before the session. A mentor who reads it and arrives with questions of their own is already showing you how they work.

A mentor is not a consultant. A consultant solves a defined problem for a fee; a mentor helps you make better decisions over time. Many people on ConsultChat offer both, and a paid 30-minute session is a low-risk way to test the fit.

Questions about their experience

1. What have you built, and what happened to it?

You want a specific story with a beginning and an end, including the ending if it was a failure or a modest exit. Vague answers ("I've been involved in several ventures") are a warning sign. Someone who sold a business for a small sum and can explain why it was not larger is often more useful than someone who only mentions wins.

2. When did you last do this yourself?

Markets, tools and costs change. Advice on hiring, pricing or online marketing from 2012 may be actively harmful now. Look for hands-on experience within the last three to five years, or a mentor who is open about where their knowledge is dated.

3. What is the most expensive mistake you have made in business?

The answer tells you two things: whether they are honest, and whether their mistakes are relevant to the risks you face. A mentor who says they cannot think of one is either not reflective or not telling you the truth.

4. Have you worked with a business at my stage and size?

Advice for a venture-backed start-up is often wrong for a sole trader turning over £60,000, and vice versa. Ask for an example of a business they have helped that resembled yours, and what changed as a result.

Questions about how they work

5. How do you prefer to work: scheduled sessions, ad hoc messages, or both?

There is no right answer, only a right answer for you. If you need someone to think aloud with every fortnight, a mentor who prefers one long quarterly call is a poor match.

6. What do you expect from me between sessions?

Good mentors expect you to do things and report back. If the answer is "nothing in particular", the relationship is likely to drift into pleasant conversations that change nothing.

7. What will you not advise on?

Every honest mentor has limits. Legal structure, tax and regulated finance are the usual ones; for those, GOV.UK's business section and a qualified professional are the right sources. A mentor who claims to cover everything is overreaching.

8. How will we know if this is working?

Agree a measure early: a decision made, a first customer, a hire completed, a pricing change tested. Without one, you will carry on out of politeness long after the value has gone.

Questions about your business

9. What is the weakest part of my plan?

This is the single most useful of all the questions to ask a business mentor, and you should ask it in the first session. A strong mentor will name something concrete: your margin assumption, your reliance on one channel, your pricing. Then listen for whether they can explain how to test it rather than just criticise it. Our guide on how to validate a business idea covers the testing side in detail.

10. What would you do in my position in the next 30 days?

You are not obliged to follow the answer, but it reveals how practical they are. A list of three actions with reasons is a good sign. A speech about mindset is not.

11. What do businesses like mine usually get wrong at this stage?

Patterns matter. Someone who has seen twenty small service businesses can tell you that most under-price, most hire too late or too early, and most avoid their numbers. Ask which of those applies to you. If hiring is on your horizon, our piece on hiring your first employee covers the costs and obligations most founders underestimate.

12. Who else should I be talking to?

A well-connected mentor will name a type of person, and sometimes an actual person: an accountant who works with your sector, a peer a year ahead of you, a supplier. A mentor who positions themselves as your only source of advice is not acting in your interest.

What good answers sound like

Question	Weak answer	Strong answer
What have you built?	"Various ventures over the years"	"A cleaning franchise I ran for six years and sold in 2021 for less than I hoped"
Weakest part of my plan?	"It all looks solid"	"Your 40% margin assumes you never discount; test it with your first ten quotes"
Next 30 days?	"Focus on your why"	"Call five past enquiries, raise your day rate by 15%, and set up basic bookkeeping"

How to use the answers

Once you have worked through these questions to ask a business mentor, score each candidate out of three on experience, working style and insight into your plan. Anyone scoring two or lower on experience is out, however likeable. Between two strong candidates, choose the one whose working style you can realistically keep up with for six months.

Taking the next step

Twelve questions sounds like a lot, but most take a minute to answer and the session will move faster than you expect. Send your one-paragraph summary in advance, ask the questions in order, and write down the answers. You will know by the end of a 30-minute call whether to book another. For the broader options, from one-off sessions to ongoing support, see our guide to business advice online. When you are ready to test a mentor with a single paid session, create a free ConsultChat account and search for people who have run a business like yours.