Everything startup founders need to know about finding and keeping a mentor

Holly Cardew mentor

Photo by Matthew Ho

In the early days of Facebook, Mark Zuckerberg turned down a $6 million investment offer by Don Graham, chief executive of The Washington Post. Graham, however, was impressed by him and became his mentor, guiding him on how chief executives behave and later on hiring Sheryl Sandberg as chief operating officer.

When I was starting out, everyone was telling me I needed a mentor, but they didn’t mention how difficult it is to find one. Sure, you can get good general advice, but finding someone in your industry who can guide you through obstacles takes a lot of time. And being a solo entrepreneur for so many years, I became accustomed to doing everything myself. Plus, everyone I met at networking events seemed to be in the same boat as me  —  hustling!

Now that I have been both a mentee and a mentor, I understand how important it is to find someone appropriate who is a good match for you.

Don’t underestimate the impact a mentor can have. After working in the Macintosh division at Apple and later when starting Salesforce, Marc Benioff looked to Steve Jobs for guidance. Benioff even says: “There would be no Salesforce.com without Steve Jobs.”

Read more: Female mentors foster greater sense of belonging among women studying engineering

So how do you find a mentor?

Your best route to finding a mentor is to build authentic relationships with people in your field who you respect. Use social events and interactions and grab lunch or a cup of coffee with people you look up to. Make an effort to stay in touch  —  even if your paths lead you in different directions.

Alternatively, if you can muster enough discipline, you can consider the furnace of experience as your mentor and source guidance and wisdom from online influencers. This could work, sure, but a personal relationship with a mentor offers much more substance in the form of accountability and one-on-one conversations that boost your drive to succeed.

Often, a lot of the things you will learn will be from these mentor-like interactions and conversations. “Start having conversations and soaking in the mentorship moments,” says Robert Herjavec of Shark Tank.

Start by giving and asking for counsel, and thank people when you get a positive outcome from received advice. A mentor is also looking for something from this relationship … often the pleasure of seeing someone they help achieve great things.

If you feel like the person across from you is a good match, take the next step and offer a more formal mentorship. Ask them to mentor you, and outline the form this relationship will take: the ways you’ll communicate, the frequency, and your mutual objectives.

And don’t get discouraged. Mentors are important. “Find a mentor. Mentors are positive people who will help you find the lessons in your experiences and use them to move forward”, says  Bud Bilanich.

The benefits of having a mentor

A good mentor really cares about your success, keeps you in check, and always tells you the truth … even if it hurts.

A successful mentor-mentee relationship brings benefits to both sides. Find a mentor who you admire and who is also looking for someone to pass along their experience to.

What you get is inspiration to take risks, support during setbacks, and goals clarification from a more mature and experienced individual, often helping you understand the lessons from your own mistakes. Your mentor is also there to ask you the uncomfortable questions that you often push aside.

Twitter’s founder Jack Dorsey has said to have learned to think bigger and better from his mentor Ray Chambers.

Your mentor is someone you aspire to be like and whose values and work ethic you share, so the relationship is like an informal education that helps you to make better decisions. By gaining access to your mentor’s toolkit and network, you can deepen your expertise in your field and encounter more development opportunities.

Rob Kalin, the founder of Etsy, got a hand in raising funds from his mentors Stewart Butterfield and Catarina Fake, co-founders of Flickr.

You also receive the gift of motivation and drive from the power of accountability. When you set objective and have to report to your mentor on your progress and the steps you are taking, you are bound to be more diligent in execution and more likely to get better results.

A good mentor will help you acquire the mental tools and characteristics that keep you on track to success. In return, the mentor gets the pleasure of seeing you grow under their guidance. Most successful people love to be able to help others learn from their own mistakes and feel like they’re creating another legacy by having a hand in your success.

The chief executive of Pepsi, Indra Nooyi, believes in finding mentors for all aspects of life and says, “If I hadn’t had mentors, I wouldn’t be here today.”

Follow the rules of conduct

Think of mentoring like the relationship between Obi-Wan Kenobi and Luke Skywalker in Star Wars, but usually in a more formal setting. Show respect for the relationship so you can grow with it.

1. Know your objectives

Guidance is not going to help you if you don’t know where you are going. Be honest with yourself about your mission and values and then match them to a mentor. It is vital that your objectives are clearly communicated so your mentor can build on them.

General Motors chief executive Mary Barra believes in acquiring more than one mentor and says: “When building your network of mentors, be honest about your mid- and long-term career goals, and how hard you are willing to work to achieve them.”

2. Respect your mentor’s time

Be on time, show that you are committed to staying on track, and respect the time they are investing. Your mentor is setting aside time to help you grow and being punctual demonstrates commitment and enthusiasm. Often, starting out with 15–20 minute calls can help shape and establish the relationship without too big of a time commitment.

Respond to any calls or emails timely and in a way that corresponds to the nature of the relationship. Your mentor is a key figure in your development and should take priority. If your relationship involves assignments, meet deadlines and be prepared to defend your work to demonstrate your commitment and keep your mentor engaged.

3. Keep confidentiality

Mentors will often share things they do not tell their general circle of acquaintances to illustrate a point or motivate you. Even if confidentiality is not formally established, you should adhere to common courtesy and refrain from sharing matters that may be sensitive and over-revealing.

4. Be diplomatic during meetings

Read the relationship, and communicate and behave in a manner that corresponds with it. Keep in mind that this is not a personal relationship and you should always extend certain courtesies. For example, if your mentor suggests something that you think is stupid, don’t call them out on it like you would when bantering with a colleague at lunch. Show a little more sensitivity when you explain why you disagree.

What to do at your first meeting

Establish a timeframe

Introduce a timeframe that works for both of you, including the frequency of meetings, length  —  on average an hour  —  and format. Outline what each meeting will address so your mentor can prepare materials and examples.

Take notes and dig deep into them

Make mental or written notes during sessions, mull them over and build your questions on them for the next meeting. Demonstrate that you understand and dig deep so your mentor can offer ever more detailed insights and guidance.

Think ahead and summarise

On closing each meeting, take a few minutes to outline what has been addressed and what is outstanding to discuss at the next appointment. By clarifying, you will both stay on the same page, and your mentor will know what to address next time around.

Schedule your next meeting

At the end of each session, sync your calendars and make arrangements for the next meeting, making sure the time is convenient for both parties.

The etiquette of gift giving

There are no strict rules on what is allowed and what is not in terms of giving a gift to your mentor. But, it is very important to be as thoughtful as possible so that you don’t offend them or give the wrong impression. If the relationship has been productive, that is already rewarding enough for both sides. You get invaluable guidance, and your mentor gets the pleasure of seeing a pupil achieve and grow under their wing.

Going the extra mile and offering tangible proof of appreciation should be within the boundaries of the relationship you have created. Avoid gifts that are too personal and can be misinterpreted  —  especially if the pair is of mixed gender. Money and expensive gifts are usually never appropriate and can be very uncomfortable for everyone. Often, a gesture is more valuable than an actual gift.

Steve Jobs was Facebook’s founder Mark Zuckerberg’s mentor, and when he passed away, Zuckerberg posted on his page: “Steve, thank you for being a mentor and a friend. Thanks for showing that what you build can change the world. I will miss you.”

Use what you know about your mentor and offer something small but meaningful, like a book they have mentioned they would enjoy, a desk bust of a famous philosopher, say, Marcus Aurelius, whose teachings were used to illustrate a point, or a framed photo with symbolic meaning.

Stay in touch and communicate key career developments

Your relationship with your mentor should not just evaporate after the last session. Stay in touch by inquiring about their affairs and update them on your career development. The best mentor relationships are those that last a lifetime.

Some of the most successful mentees worked alongside their mentors for decades before receiving the torch to leading their mentor’s company, like Tim Cook and Steve Jobs of Apple or Satya Nadella and Bill Gates of Microsoft.

Never stop giving back and sharing experiences and findings that are insightful and inspiring. Enriching your relationship is the best way to foster a lifelong friendship and repay your mentor for their selfless gift of wisdom.

Mentee Checklist

Here is a quick checklist when finding a mentor

  • Make sure you have clear goals.
  • Communicate with people you think can help you achieve them.
  • Research your mentor’s digital channels — Twitter, Medium, LinkedIn etc.
  • Send an outline of your goals and development aspirations.
  • Start with 15–20 minutes calls to establish compatibility.
  • Agree on the frequency of meetings (this does not have to be done on the first call).
  • Schedule your first in-person meeting.
  • Send a meeting agenda of the couple of things you would like to cover.
  • During your meeting, revisit goals and how they relate to the meeting agenda.
  • Address any feedback or direction promptly.
  • Prepare agendas for each meeting based on current challenges.
  • Always follow up — Yes I am guilty of not doing this every time
  • If the relationship is set to expire, offer your gratitude and suggest staying in touch.
  • A small thoughtful gift can be appropriate — offering to buy their coffee during your meeting is great too.
  • When you find the right match, offer a formal agreement, this might include stock options in your company.
  • Stay in touch, and communicate key developments.

Mentee Email Template

Here is a sample email on how to start a relationship with a potential mentor.


It was great to meet you at EVENT NAME. I’ve had a chance to read some of your Medium posts and thoroughly enjoyed your blog on XYZ. I agree that XXXXXXXX.

As I mentioned, I run a successful B2B eStore, selling high-quality yet affordable basics, such as socks, t-shirts, and jeans. Despite the fact that we have a solid business model, we still have challenges scaling our operation due to external factors.

Our Chinese manufacturers often have problems automating certain aspects of their logistics, which can have a huge knock off effect on us. You mentioned you might be able to offer some advice on how to manage the situation.

I’d love to schedule a quick call at a time that’s most convenient for you. I’m happy to send more details beforehand if that’s easier. I understand that you are very busy and really appreciate your time.

Look forward to hearing from you soon,

CEO of Basics & Co.

Let me know if I am missing anything on my checklist. I would love to add to it!

This article was first published on Medium

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4 years ago

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4 years ago

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4 years ago

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Zahid Anowar
4 years ago

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2 months ago

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