How to nab yourself a career and money mentor

Main pic: Alicia VanNoy Call

Getting yourself a mentor – it might just be one of the best decisions you’ll ever make. I explain how that special someone can help guide your career and finances, where to find them, how to approach them and set up the relationship so it lasts the course.

Say the word “mentor” and certain images of Mr Miyagi teaching Daniel to wax-on, wax-off will spring to mind (if you’re of a certain vintage, of course).

To sceptics, it indicates a certain power imbalance – an older, wiser mogul telling a young slip of a thing what to do. But while Mr Miyagi’s methods were unconventional, you never doubted that he had his young apprentice’s best interests at heart.

By contrast, anyone who has been in the workforce long enough will have come across a fair number of condescending power-trippers, who just *love* to dispense inappropriate and blunt advice purely to massage their own egos.

This is one reason why I used to be wary of mentoring. Okay, I have been luckier than most – my dad was in a closely-related career to mine before he semi-retired, and he has been a constant source of advice throughout my career.

I certainly know he is on my side, with the added bonus that we can communicate far more frankly with each other because we’re related. I have also always viewed myself as independent-minded and, at times, quite rebellious – so it certainly goes against my instincts to defer automatically to other people.

But there are downsides. Taking all your decisions on your own can be very frightening and difficult. You get too close to situations and stuck in a rut. It’s easy to let your emotions overrule your reason. And family and friends are often not well-placed tell you what to do next. As well as lacking knowledge of your industry and career field, they may let their personal relationship with you get in the way of giving objective advice.

I was named Freelancer of the Year for 2018 by IPSE, the trade association for the self-employed, and one of my prizes was a mentoring package. Mark Roper from Aon has been helping me to crystallise my goals and work out the necessary steps to take over the past few months. I was blown away by how helpful the process was. While Mark isn’t exactly in my career field, he has a wealth of business expertise (as well as a fantastic personal manner) that made him an ideal person to guide me at this time. I can express views, doubts and ambitions to Mark that hasn’t been possible for me before. Just taking a step out of the usual grind to check in with my goals, and see how I’m working towards them, has been hugely worthwhile.

Now, I’m a total mentoring convert. But finding someone to listen, guide and support you is not always easy. I was fortunate to be introduced to a great mentor by a third party, but it can be daunting to ask someone much more experienced than you if they’ll take on the task.

But it’s worth doing your homework, scouting out some likely names and drawing up your own shortlist. Because if you pick the right candidate, and set up your relationship well, the results will speak for themselves. In this quick guide, I’ll take you through how mentoring works and how to make that all-important approach to someone you trust – catching flies with chopsticks optional.

What is mentoring?

Remi Walle

Mentoring should help you clarify your long-term goals, work through the steps you need to take and help you get ahead. Yes, you can do this on your own but an outside person will help you interrogate your current methods and aims, act as a crucial sounding board for your ideas and gently steer you towards the outcomes that are going to be far more effective. But you don’t have to be too prescriptive about what you want to get from mentoring. You might benefit from learning how to manage your time better or how to get more from your network. It depends on your age, stage and personal habits. And there are no hard and fast rules about how mentoring should be arranged: your meetings could be weekly, monthly or even quarterly. It can take place in an office, your local or the park – whatever suits you both.

Gold-star mentors should also have a rich contacts book and resources they can share with you. They will be enlightened enough to believe that a “rising tide lifts all boats” – if  younger people in their industry are thriving and innovating, everyone wins. So don’t worry that this is a one-way street – mentors benefit just as much from the relationship, gaining a fresh insight from younger people and passing on knowledge that sustains businesses and industries. Most people love to be asked if they can help others and will do everything they can to build up your confidence.

How do I find the right mentor?

Ideally, a mentor should be in your industry so they have enough knowledge of what you’re trying to do. It goes without saying that they should be experienced, but that doesn’t necessarily they have to be much older than you. Indeed, a mentor closer to your age might grasp some of your dilemmas more vibrantly. Either way, they should be inspiring to you and a good communicator, someone who doesn’t leave you in any doubt about what you should try next. They shouldn’t be your current boss or senior manager, but nor should they be someone working for a rival company (if you’re a full-time employee). Your mentor needs to be impartial and able to take the long view. Maybe there is a leader in your field you admire, or perhaps someone approaching retirement after an illustrious career. Of course, they may be too busy but you’ll only know if you ask. Don’t downsize your expectations in the beginning – aim high and see how far you get.

If you’re looking for a money mentor, you can cast your net further afield. Is there anyone in your personal circle who seems to be really clued-up and confident about their finances? Someone who seems to know what all the latest financial apps are, is constantly switching their savings or seems to have a way with discounts? If so, they’ll be uber-flattered if you ask them for some tips. Okay, it doesn’t have to be as formal as a career mentorship but having someone who will help you clarify your financial goals would be immensely useful.

How do I make the approach?


If you don’t know your ideal mentor, send a quick email. Tell them why you admire them (but don’t be too gushing), and try to be as specific as possible. Again, make it clear that you’re looking for their ongoing advice. A few sentences will suffice, ending with a suggestion to meet over coffee. No rambling emails that would give James Joyce a run for his money. Give them a week to respond before sending a polite follow-up. Two follow-ups are your maximum – don’t badger them with any more. And refrain from sending a stinging email at 2.30am saying what a stuck-up, arrogant popinjay they are, unless you want your email to be shared with numerous WhatsApp groups and possibly the Daily Mail. Always be polite and walls of silence are your cue to move on in a dignified fashion.

If you already know your ideal mentor well, pick up the phone and suggest meeting up, with a view to discussing a mentorship. Being clear about your agenda means they won’t feel they are being accosted unexpectedly. The lunch or coffee should be a pleasant formality, with both parties knowing whether it will be a ‘yes’ or ‘no’.

If the response is lukewarm or negative, leave the door open – don’t slam it shut! They may be too busy right now but things could change – they could go on sabbatical, gardening leave or retire sooner than you think. And your confident approach will be viewed very favourably, meaning you could gain opportunities even without a formal mentoring arrangement.

As a compromise, ask if they would mind some quick questions over email once in a while – most wouldn’t say no to that. And if the answer is no, ask if you can check in with them again in the future, just in case their circumstances have changed.

My ideal mentor said yes – what now?

Great news! But before you get carried away, you need to weigh up whether they are the right mentor for you. That’s why the meeting is a crucial testing ground. Remember that this is a two-way street – you’re eyeing them up for the position of mentor, and you have a lot to offer, so you don’t have to be Mr or Ms Desperado. Start with your personal chemistry – do you get on well? Can you (at the very least) do some pleasant small-talk with them so your meetings don’t feel like a total grind? Next, assess whether your mentor has the right expertise and knowledge to help you – be specific about the progress you’re looking to make, and invite them to tell you where their credentials fit in. Then you need to understand whether they have the right personal qualities for the job. Are they empathetic? Can they do “constructive criticism” well, or is it liable to just become criticism? Will they encourage you but not let you off the hook? A hard-headed mentor should feel like they can be honest with you at all times.

If they pass the test, it’s time to arrange the practicalities: how often will you meet? What issues will you concentrate on? How will you measure progress? At the beginning, having a precise outcome in mind – such as getting a promotion or more commissions – will give you both something to work towards. Okay, your goals might change radically over the course of the mentorship (that could be a sign that it’s working really well) but you don’t want to be too nebulous from the outset (hope Theresa May isn’t reading this!)

Bonus points if you can go to your mentor and fit in around their schedule. Finally, you need to come well-prepared to every meeting. Be on time, make notes or record your conversation, clarify any action you need to take at the end of the meeting – and make sure you put them into practice in-between!

What are your experiences of mentoring? Let me know by leaving a comment or tweeting @ionayoungmoney…

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