Mentores: A practical guide for finding, engaging, and learning from mentors

Updated on Mar 14, 2021

As a tech entrepreneur, I’ve cofounded many businesses — and also failed many times. In hindsight, most of these failures were the result of having made simple mistakes. Those mistakes were not unique to the business we’re in; they’d been made by other companies before we made them.

There’s an important lesson here: Life is too short not to learn from mistakes made by others. What this means is that, as a company, we now subscribe to the view that making mistakes is okay as long as the ones we make are unique.

Fortunately for us, we’ve discovered the value of mentoring. By definition, mentoring is about the experienced counselling the inexperienced — but for us, it’s more than that: it’s also about companionship and camaraderie; it’s about sharing, growing, and getting ahead with the kind of confidence that will allow us to succeed at making a difference.

Systematically since 2011, we’ve made seeking, finding, and meeting mentors a proactive pursuit that has contributed consequentially to the success of some of my teams.

Why? Because our mentors help us envision the way forward as well as foresee potential mistakes. They’re able to answer questions based on their experience. More importantly, our mentors help us identify the questions we should be asking ourselves. As Fred Wilson wrote, some mentors will ask questions such as “why don’t you try this?”. Others will ask questions such as “why do you want to do that?”. Both are valuable.

The process of finding and engaging mentors never stops. It’s an ongoing effort that requires discipline, but the rewards are frequently substantial. By constantly finding new mentors and engaging with existing ones, we’re able to grow much faster than before, both as human beings and as professionals.

This guide is based on my experience in this regard. We've used it successfully at Torre for several years now. We call this framework Mentores (Spanish for mentors). I’ve divided it into four sections: identifying mentors, engaging them, meeting with them, and then following up. If you have any suggestions on how to improve this guide, please don’t hesitate to share them.

Part 1. Identifying potential mentors

What to look for in mentors

Usually, the best mentors are ones with experience executing objectives that are similar or comparable to yours. This applies to both short- and long-term goals. For example: As CEO of Torre, one of my objectives is to grow the impact and user base of the company. Some of my best mentors have been Gary Swart, former CEO of oDesk, and Diego Piacentini, Senior Vice President of International Consumer Business at Amazon. Both have vast experience in building teams and growing marketplaces.

For short-term goals, a good example is Camilo Gomez, a manager at Google and former entrepreneur. Camilo built inbound sales teams. When Santiago Jaramillo was building an inbound sales team for Bunny Studio, Camilo’s mentoring session was great for him; he was able to refine his approach to recruitment by having a conversation with someone who had encountered similar recruiting challenges and had had similar experiences. Santi stepped out of the meeting enriched and confident.

That said, however, it’s important to ensure you don’t confuse ‘objectives’ with ‘titles’. For example, just because your role is that of Senior Software Engineer, doesn’t mean anybody else with the same title will be a good mentor for you. The experience of other senior software engineers may be irrelevant unless they worked on objectives related to yours.

Where to look for mentors

Potential mentors can be found in many places and discovered in many ways. These may be the most common:

• Friends and co-workers. Your friends and coworkers can be your mentors. Even more importantly, they can help you identify potential mentors. Just ask them either privately or publicly via social media or company-wide communication channels.
• Vendors. Some vendors have experienced people who may be willing to help you, especially large vendors that have been out there longer than you have.
• Social networks. Recruiters use social networks for a reason! While LinkedIn limits the amount of searches you can perform without paying them, recently they have been experimenting with a matching service that connects mentors with potential mentees.
• Networks of professionals. Usually, the more difficult it is to get in, the better the mentors you're likely to find there. Examples include Global Shapers, Young Entrepreneurs Council, Young Global Leaders, a local chambers of commerce, etc.
• Alumni networks. Many institutions and companies (including Torre), have alumni networks. They often have people who have done great things.
• Accelerators. You don't need to have attended an accelerator to be able to tap its mentors. As long as a colleague has attended one, you may be able to tap the same network. For example, Torre has access to Endeavor, a non-profit organization that helps high-impact companies in emerging and growth markets. Tania Zapata, Santiago Jaramillo, and I were accepted as members in 2013. We share our login credentials with everyone at Torre so that they can look for mentors using the Endeavor network. When a team member finds a potential mentor, we do the introduction.
• Coworking spaces. Although most companies who make use of coworking spaces are young, some of their team members may have considerable experience. Most coworking spaces have some kind of chat facility or channel where you can look or ask for potential mentors.
• Meetups. Meetups are mostly attended by inexperienced people, but organizers and speakers may be good mentors or may know others who could be. To look for meetups near you, check out Meetup.com and look for interest groups on Facebook.

Tip: Famous people are hard to get hold of, but the people who report to them can be just as smart and helpful. They also tend to be easier to contact, so it’s a good idea to reach out to them first.

Tania Zapata and me after a mentoring session with Jimmy Wales, the founder of Wikipedia

Part 2. Engaging potential mentors

Why mentors mentor

Why would someone mentor you? The answer differs from person to person, but it’s important to understand the motivations of the mentor. Knowing this will help you to better engage with them. Some of the most common motivations are:

• They like you. Maybe they see the potential in you. Maybe your personality appeals to them. Maybe they’re physically attracted to you — but that could become problematic. In such instances, always be cautious and remain resolutely professional. Conversely, some mentors simply enjoy mentoring and watching others achieve their goals; they expect nothing in return.
• They like what your company is doing and would love to help you grow and have a wider impact.
• You have something they want. Maybe they need to hire somebody like you. Maybe they want to invest in you or your company. Maybe they invested in a competitor and would love to know what you’re up to.
• They are doing someone else a favor. Maybe somebody asked them to mentor you and they feel obligated as a favor or because they owe a favor to that person.

Contacting potential mentors

How you approach a potential mentor the first time is very important. Below there are three different scenarios and tips for each one: If the potential mentors knows you, if you have contacts in common, or if you don’t have contacts in common.

Additionally, ensure your social media profiles are up to date. Many potential mentors will scrutinize them to determine if you’re the kind of the person they’d like to meet with.

Scenario 1: If the potential mentor knows you

Keep in mind the following:

• In most cases, the first approach will be via email.
• Start with genuine flattery.
• Explain why you’re emailing the person.
• Pitch the awesomeness of the project you want feedback on, with a ‘why/how’ approach.
• If you’ll soon be in the same location as the potential mentor, tell the person you can visit them. Otherwise, propose a video conference.
• Have a clear call-to-action.
• Be brief and assertive.
• Don’t use the word mentor. It may intimidate.
• Be prepared to get rejected.

Tip: Here is a template for contacting a potential mentor you already know:

[Greeting] [Flattery] [Credentials] [Project details] [Meeting request]

Real sample message embedded in a stock photo of an overly organized desk.

Scenario 2: When you have a contact in common with the potential mentor

In this scenario, the first step is get an intro. If you have multiple contacts in common, get the most influential of those contacts to do the intro.

Ideally, this is how intros should work:

1. Verbally or via chat, you ask the common contact for an intro.
2. If the common contact agrees, tell him/her that you will send them an email they can forward.
3. You send a ‘forwardable email’ to the common contact, adding contextual information that will make you sound interesting.
4. The common contact forwards the email to the potential mentor asking if he/she is interested in an intro. (In some instances, the common contact may skip this step and go directly to step 6).
5. The potential mentor replies positively to the common contact.
6. The common contact introduces you both.
7. You reply thanking the common contact, move him/her to bcc, and ask the potential mentor for a meeting.

Tip: Here is a template for a forwardable email:

[Greeting] [Context] [Intro reason] [Project details] [Intro request]

... and a template for replying after a successful intro:

[Intro thanks]

[Greeting] [Flattery] [Credentials] [Project details] [Meeting request]

Sample embedded in a stock photo (shamelessly promoting one of our products, Torre Bio. Plus, I don't drink coffee!)

Scenario 3: When you don’t have a contact in common with the potential mentor

This is trickier, but doable. A cold email should sound more like a meeting of equals than a mentoring session.

1. Find (or guess) the email address of the potential mentor using tools like FullContact. Alternatively, send a tweet: “Hi Alex, I’d like to send you a brief, private email message. Could you please email me at you@domain.com?”
2. The message should usually be about ‘sharing notes’ because your project is related to his/her project.

Tip: Template for contacting a potential mentor you haven't met:

[Greeting] [How you learned about the existence of the person] [Flattery] [Credentials] [Project details] [Reason for the meeting and meeting request]

Sample embedded in stock photo. If you look closely, you'll see some cigarettes. Go figure.

Handling rejections and indifference

Many times potential mentors will either reject your request or plainly ignore it. That’s ok. Even if only one out of ten potential mentors agree to scheduling a session, you still have a 10% conversion. When it comes to email marketing, a 10% conversion rate is great! On the other hand, if you have a 100% success rate, it may mean you’re not shooting high enough, so target people with higher profiles. Keep in mind that Mario Andretti, the famous racing driver, said: “If everything seems under control, you’re just not going fast enough.”

Tip: If you sent an email and received no reply within a week or so, you can follow up by replying to the original email with this text: "Hey Joe. Just circling back."

More tips: Yesware is a tool that allows you track when people see and click on the emails you send. It may be worth using to track the performance of the messages you send.

Scheduling

Once the potential mentor agrees to a meeting, it’s time to schedule it. Keep the following in mind:

• Ideally, meetings should be in person. If that’s not an option, then do a video conference. I discourage mentoring sessions over the phone. Not seeing the face of the other person seriously reduces the human factor.
• For in-person meetings, select a quiet place. Offer the mentor the opportunity of going to his/her office or home, or invite them over to your place and cook dinner for them. Avoid coffee shops and restaurants as they tend to be noisy and distracting. If you must use one, get a quiet table. If you eat something during the mentoring session, it’s best not to let the mentor pay the bill.
• For video-conferencing, give the mentor the option to select the software s/he prefers using. Make sure you have a noise-canceling mic and excellent Internet connectivity.
• Mentoring sessions are usually between 30 and 60 minutes. Let the mentor decide how long it should be. If you invite the mentor to dinner, you may be granted more time — although the meeting may be more personal and less structured.
• Knowledge isn’t valuable unless it’s shared. As soon as you schedule a mentoring session, let your colleagues know about it. This will allow your coworkers to suggest questions that might generate useful insights or worthwhile connections.

Example of a scheduling message:

Thank you Gary. Where would you like to meet? Your office or any other location of your choice will be fine. Please let me know a few time slots that work for you. I’ll adjust my calendar accordingly. Alternatively, my wife and I would love to host you at our place for some home-cooked, traditional Colombian food for both you and your significant other. We live in Soma.

Part 3. Meeting the mentor

Before the mentoring session starts

1. Look for information on the mentor. Read his/her bio. Watch his/her most popular videos. Read his blog posts and books. You don’t want to ask questions that have been answered online already.
2. Find out about his/her recent thoughts and activities on social media. They may be great icebreakers.
3. Come up with three to five questions and prioritize them. Don’t ask simple, ‘yes/no’ questions. If you do, the mentor may feel he/she is wasting their time as these questions could have been addressed via email.
4. Memorize the pitch of your company and the project you’re working on.
5. Have a notebook and pen handy.
6. Be at the location 15 minutes before the meeting starts, even if it’s a video conference. A mentor’s time is usually extremely valuable. Being late for a mentoring session will leave a very bad impression.

Tips: Some questions I love asking mentors include:

- "You were successful doing something relatively similar to what we’re trying to do. What were the main reasons for your success?"

- "What mistakes did you make that we should avoid?"

- "If six months into the future you learn that I/we failed on this front, and you had to guess the reasons for failure, what might those reasons be?"

While in the mentoring session

Follow these steps:

1. Turn off your phone.
2. Break the ice, if possible.
3. Thank the mentor for taking the time to meet you and congratulate them on their achievements. Explain, sincerely, why you admire them.
4. Tell the mentor you have x number of questions and you hope to be able to ask them all before time runs out.
5. Ask the mentor why he/she is meeting with you. What motivated him/her to share their time with you. Whatever the answer is, it’s likely to come in handy going forward.
6. Pitch your company to the mentor, and explain the why and how of the project you’re working on. Be passionate and sincere. Your level of energy during this step will determine the mentor’s level of excitement.
7. Ask your questions. Make use of time wisely so that you can ask all your questions and leave extra time for more questions that may come up on the fly. It’s fine to glance at your watch every now and then to ensure you’re on track.
8. Write down some answers on the notepad. This will make the mentor feel they’re being taken seriously. Don’t use a laptop, tablet, or smartphone.
9. The best mentors will help you realize the mistakes you may be making. Don’t try to justify them. Don’t get involved in a debate. You’ll look like a fool if you do. Listen and learn.
10. A few minutes before wrapping up, ask the mentor how, or if in any way, you could help them.
11. Ask the mentor to suggest other potential mentors: “Who do you think I could talk to about this?” Almost 100% of the time they’ll recommend someone.
12. Ask the mentor if they’d like to receive updates on your progress.
13. Thank the mentor.