How To Find (And Be) The Right Mentor

Finding the right mentor is hard. And while they are essential to success, most mentoring models are stuck in the past. 

I mentor 40+ entrepreneurs alongside my family commitments, and role building Drop Bio. If you’ve just thought, ‘how does he fit that in?’ or ‘that must be a distraction’, I’d like to introduce you to a very different mentoring model. I also have four mentors who don’t fit the typical mould. 

In this post, I share how people can find their perfect mentors and how to approach being a remarkable mentor. I base my views on over 20 years of leading and following a broad spectrum of personalities, and one lesson: To become a great mentee or mentor takes time. 

The best mentees are people who love to listen and learn.

The best mentors are ready to deploy their domain expertise at a moment’s notice to advance their mentees’ mission. 

And on the other side of the equation are people who like the idea of being part of a mentor relationship but probably shouldn’t be. With that, let’s start with some myth-busting.

Mentor relationship myths

There are exceptions to these rules, but here are the myths I’d like to bust to help you create valuable mentoring relationships. 

1. There’s money in mentoring

There is one exception to this rule, but for the most part, no, there’s not. My general rule is if someone requests payment for mentoring, you should run as fast as possible in the opposite direction. 

Building a consulting business model around mentoring is a bummer for two reasons. First, it creates incentive asymmetry between the mentor and the mentee. The mentor needs payment to stay in business which inevitably drives short term thinking and decisions. And the mentee needs long term support and foresight. Second, it’s an impossible business model to scale. The hours-in-the-day maths simply doesn’t work. 

I believe mentoring should be an act of altruism. If done well, it can generate reputation and relationship capital, but it’s the icing on the cake.  

That said, mentoring should not be confused with coaching. Coaching is a profession in which people like my friends Melissa Rosenthal and Andrew Williams are paid to improve the strategic capability of individuals and organisations. While they face challenges in scaling their reach, the role of a coach is grounded in behavioural psychology, structured programs and achieving long term performance gains. 

On the other hand, mentors tend to be domain experts and provide more tactical, as-needed support and guidance.

The one exception I mentioned earlier relates to organisations that match people with mentors. In both cases, the mentors and mentees are hand-picked and vetted. The critical factor to note here is that this match-making is in service of achieving a specific purpose, not just to make money. A great example of this is Inspiring Rare Birds and their work in supporting women entrepreneurs (Disclaimer: I’m an Inspiring Rare Birds Ambassador and mentor). 

Finally, I think to be a valuable mentor (or coach), the mentor must have lived experience that’s directly relevant to the mentee. If they don’t, there’s an excellent chance they are wasting your time, and theirs. 

2. It always happens face to face

Nope, doesn’t need to. Mainly when geography is an issue. 90% of my mentoring conversations happen via Zoom. 

It’s a quick and high-quality alternative to travelling to, meeting and then travelling from a mentoring conversation. Importantly, a zoom call is free and can be started at a moments notice and is especially useful for when the unexpected arises. And when you’re building a company, the unexpected is a daily thing. 

3. Mentors are older (and the same sex)

While wisdom is often proportionate with age, it’s not a universal truth. One of my mentors is 12 years my junior and she is fantastic. 

It’s also not uncommon for men to feel uncomfortable being mentored by women and vice versa. 

All I will say is this: Gravitate towards those with wisdom and compassion regardless of age or sex. 

And it’s essential to have both because as Fred Kaufman says, ‘Wisdom without compassion is ruthlessness and compassion without wisdom is folly’.

4. Value flows one way

The people who I consider the best mentors share one trait in common: they get more out of mentoring sessions than the mentees. 

They learn from their mentees’ situations and questions because they are genuinely invested in their future. This usually means mentees receive more value per interaction than those being ‘mentored’ by people who are doing it out of some sort of obligation. 

The bottom line is that value flows both ways when the right mentee and mentor work together.  

5. It’s an open-ended relationship 

A mentor relationship should be time-bound. Because the needs of a mentee and the priorities of a mentor change with time. 

12 to 24 months is about the right time for a formal mentoring relationship. Anything longer or open-ended will likely result in one of the parties becoming disengaged. 

However, there are exceptions to this rule. One of which is the relationship transition that often happens. It’s common for a well-matched mentee and mentor to become colleagues or friends after the formal relationship concludes. 

To me, that’s a sign of a successful mentoring relationship. 

6. Experience equals mentor material 

Not necessarily. The reality is that a great many experienced people are not interested in mentoring, and they have their reasons. They may be focused on other priorities or could be taking a break from mentoring. 

How to find the right mentor 

I think there are three critical steps to finding the right mentor:

  1. Determine your mentor readiness
  2. Identify mentor magnets
  3. Make the ask

Let’s dive into mentor readiness. One of the best first moves a person looking for mentorship can do is honestly answer these five questions:

  1. What skillset or knowledge gaps do I need to fill to achieve my next level?
  2. What is the plan for my organisation or side hustle for the next 24 months?
  3. With who else can I share my mentor’s advice?
  4. How ready am I to be vulnerable?
  5. How ready am I to show up and listen?

The answers to the first two questions help determine your stage and the type of help you need. These answers also help with the next step: Identifying mentor magnets). 

Question three is unique and might seem counterintuitive. The reason for answering this question is that you might need help processing the advice provided by your future mentor. I learned this lesson from a number of my mentees. Let me explain. 

When a mentor is invested in your success and has the right context but not immersed in the daily operations of your business, answers to strategic questions or issues can appear with relative ease. That can be helpful, but it might take some time for you to digest and formulate a plan to action the feedback. That’s where someone you trust, who is outside the mentor relationship can help with this digestion step. Typically partners or close friends do a great job of playing this role. 

Questions four and five are where the most important. Being vulnerable isn’t easy, but a mentor relationship should be a safe place where most topics can be discussed. While vulnerability evolves with trust, mentees (and mentors) need to enter the relationship prepared to be vulnerable. 

I cannot underscore enough the importance of showing up and listening. Showing up means appearing at the designated time, prepared to talk and discuss topics that are keeping you away at night. I have discontinued mentoring relationships where the mentee hasn’t respected this virtue and repeatedly been late or cancelled at the last minute.

And by listening, I mean considering the messages that mentors share with you. The most effective mentor relationships are an exchange, not just a situation of one person talking and the other listening. 

Identify mentor magnets 

The next step after determining mentor readiness is identifying who might be your mentor. The best way to short circuit this process is to look for mentor magnets. These are people and organisations whose mission is enabled by creating impactful mentor relationships. 

Inspiring Rare Birds and the Obama Foundation are examples of mentor magnets. These organisations have built the infrastructure to attract and match high-quality mentors with mentees. 

As I mentioned earlier, it’s essential to understand a mentor magnet’s incentive for being. Walk away if their primary motivation is making money. Engage if their motive is to create a better future. 

Making the ask

The next step is to make the ask, and this can be achieved in two ways. Either by applying to a mentor magnet or by asking to be introduced to someone who might be a potential mentor. 

In both cases, mentees will be asked, ‘why do you want to be mentored?’

Here’s the template I use to answer this question:

Dear [Name],

My name is [Name] and I’m [role title/student] at [Organisation].

I write to seek mentorship to help me [insert skill set or knowledge gaps from question one, above] to help [insert plan for my career/organisation/side-hustle for the next 24 months, from question two above].

I learned about you through [insert source], and I’m excited to join this community to gain valuable experience and [insert how you plan to add value to the community]. 

Please refer to my LinkedIn profile for more details about my background or contact me via email.

[insert LinkedIn profile link]

Perhaps we can discuss further next week?

Many thanks, 

[insert name]

I encourage people sending messages like this introduction to think about it as a business development activity. As I wrote in how to create a business development habit, you might need to send several introductory messages to capture a mentor’s attention. That’s part of the process!

How to be a great mentor 

I’d like to share my perspective on what it takes to be a reliable and helpful mentor. 

The minimum requirement to be a great mentor is compassion. Mentors need to go beyond wanting to walk in their mentees shoes and have a deep desire to help them achieve their potential. 

Beyond compassion, I think great mentors:

  • Understand their experience and know-how they can help. This also means they know the industries and organisational growth stages where they cannot help
  • Are accessible. They expect and take calls from their mentees outside of scheduled meeting times. In doing so, they don’t make mentees feel like they are imposing
  • Know their bandwidth and say no if they have too much on to not deliver a substandard experience to a mentee
  • Know that feedback takes time to sink in and that mentees may need help processing the multiple voices of advice (of which the mentor is one)
  • Ask mentees for help because they value their curiosity and intellect

How I mentor

At the time of writing this blog post, I mentor 42 entrepreneurs. I embrace each of the qualities above, and I don’t have a formal mentoring schedule with each of them. Instead, I have hand-picked them to join a community I have built using the collaboration platform, Slack. 

Our slack community has subject-specific channels like Product, People, Mindset and News. Conversations flow freely between members, and each person knows that they can message me whenever they have a question or need to talk through an issue. 

My commitment to them: If I can’t talk when they need me, I’ll call them as soon as I’m free. 

What I love most about this community is that each member is an accomplished leader and doer in their own right. This means that community members don’t only have access to my experience; they can take advantage of 42 other leaders’ expertise and perspectives. 

And no money is exchanged because the value exchange is the knowledge that is continually being offered and repaid. 

If you’re a mentor with multiple mentees, I recommend this community-based approach. Slack and Mighty Networks are two platforms that can enable this. 

One last thing… 

Mentoring and being mentored are enriching experiences. It’s a relationship where encouragement is continually on offer and truths are openly discussed. The best mentors bring their A-Game to supporting their mentees, and as a result, they often hear comments like, ‘You always help me so much, I feel like I want to repay the favour’. 

To mentees who feel that way, know that if they ever need help in the future, your mentor will come knocking and ask for help. It’s just the nature of mutually beneficial relationships. 

Good luck!