Startup mentoring

Finding startup mentors and getting the most out of the relationship

Starting out young meant that much of our entrepreneurial journey has been heavily influenced by the smart people we’ve met along the way.

We were teenagers with an unbridled sense of ambition, but little clue what steps we needed to get there. We were guided by the insights of far more experienced entrepreneurs who gave up their time, wisdom and contacts to help us navigate the crazy world we had flung ourselves headfirst.

We’ve been direct beneficiaries of the power of strong mentor relationships. It’s hard to imagine if we would ever have got anything off the ground in the first place without them. But these elusive oracles are not easy to find.

Startup mentors come in all shapes and sizes and don’t conform to any fixed model. Here’s some of what we’ve learnt about finding them on our journey with CharlieHR and making the most of them.

The best startup mentors aren’t always the most obvious

If you identify a company you admire and want to learn from, it’s tempting to shoot for a conversation with the most obvious candidate, perhaps a founder or the CEO. These guys are probably not the best option. They’re busy, hard to reach and (often) too self-absorbed in their own day-to-day.

You’ll likely find there’s another lower profile, but just as talented, senior figure who’ll have fewer demands on their time but still have all the insights. These are the gems.

Choose someone you respect as a human being

Great mentoring relationships are about far more than business. They’re about making the right decisions across the whole spectrum of life. You might call them when you have a bust up with your boyfriend, you feel lonely because you’re working too much or your mum’s freaking out because you left a nice paying job to go start a company.

Choose to work with mentors whom you admire and respect for more than just their business achievements. If you share the same life values you’ll get the advice that’s right for you.

Ask for specifics

Believe it or not, one of the biggest concerns for most prospective mentors is whether or not they really can be useful. When you get in touch with them identify exactly what it is that you’re looking for and why you feel they specifically are best placed to help you. Aside from an opportunity for brief flattery, you’ll give them the confidence they can add value to the discussion and their time won’t be a waste for everyone.

Look for what you can offer

These relationships don’t have to be two way – most (good) mentors are happy just to give something back. But, don’t underplay what you could bring to the relationship. You will have a fresh perspective, huge energy and new insights that are all valuable.

You’ll likely find there’s another lower profile, but just as talented senior figure who’ll have fewer demands on their time. These are the gems.

Rob O’Donovan, Co-Founder and CEO of CharlieHR

In the past, we would help mentors understand more about our peers or how they could hire great graduates and we even introduced a few of our smart friends for jobs at their companies. If nothing else, the effort demonstrates that the value of the time they’ve afforded you does not go unnoticed.

Ask for context

Anyone can have an opinion. That’s not to say opinions aren’t important nor that you shouldn’t listen to them, but the one coveted thing that mentors have and you might lack is experience.

Don’t ask how they think you should solve a particular problem. Ask for examples and stories of where they’ve seen a similar issue in the past. How they or their colleagues went about attempting a resolution and if or why it was a success. This will force mentors to substantiate their views and help you identify bias where one particular experience has led to an irrationally strong opinion.

Follow-up on your mentor’s advice

Mentors want to know that you’ve listened and actioned their advice. The more value they feel they bring to you the more likely they are to engage long term and build a relationship.

Mentors want to know that you’ve actioned their advice. The more value they feel they bring to you the more likely they are to engage long term.

Advice is the most precious thing in the world, but it can also be the most toxic. Seek out as much of it as you can, but think long and hard about what you chose to act on.

Rob O’Donovan, Co-Founder and CEO of CharlieHR

Send them an email within 24 hours of your meeting thanking them. Outline your key takeaways and how you intend to take action on them. A few weeks later, drop them a line to show your progress and learnings. It’s also a good opportunity to suggest another meeting if you’d like to.

Do not take all advice

Advice is the most precious thing in the world, but it can also be the most toxic. Seek out as much of it as you can, but think long and hard about what you chose to act on. They may have lots more experience and big brains, but they aren’t you and they don’t run your business.

Sometimes these conversations become confusing – different people give conflicting advice. Often those with experience can fail to have the imagination you do. Listen intently, but remember that you own the decision.

Long-term mentors are hard to find

Long-term relationships with mentors rely on the strength of the personal bond you create. With some you will pick up an instant rapport. They’ll love what you’re doing and you’ll realise you share many of the same ideals. With others, you might have a great first meeting but the “spark” just isn’t there. Just like dating, finding a real connection with someone is rare and it’s unlikely to happen on your first few attempts – don’t be disheartened.

Mentor relationships can really be the making of not just your business but you as an individual. They can be equally as rewarding for both parties and culminate in real and genuine friendships that have a huge influence on your life. Seek them out earnestly, but pick wisely.

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Rob O'Donovan

Rob O'Donovan

Rob's the co-founder and CEO of CharlieHR, the HR platform for small businesses. He's also co-founder of startup studio The Eleven.

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