Get to know your mentor
With some programs, you're given a list of mentors from which to select. For other programs, you'll be assigned mentors. Either way, you'll want to do a fair amount of research on the mentor to ensure that you have a good understanding of their expertise. Doing this research will also provide the context you need to build an agenda, define clear objectives for the relationship, and target successful outcomes for your ongoing engagement with your mentor.
For this exercise, you've already been assigned a mentor with whom you're supposed to meet.
Key areas for research
Some key areas you'll want to understand about your mentor before you choose a topic to discuss or make contact with them:
Experience
First and foremost, a mentor will be providing advice based on their own personal experience in the world of startups. To get the most out of your mentor conversations, it's important to have a base understanding of that experience. Were they a founder or are they someone with extensive knowledge of the startup industry? How many startups have they been part of? Did the mentor typically serve a business role (CEO, COO, CMO) or were they in a technical role (CTO, CIO, CSO)? Did their company bootstrap or raise venture capital? Were they in a role that would have participated in that process? Did the company acquire other companies or was it acquired? Were they successful or did the company fail?
Product
While every startup is focused on exponential growth, a variety of product offerings can lead a founder down that path. For that reason, it's important to understand what type of product(s) your mentor has built in the past. What was the product focus of the mentor's company/companies? Does the mentor have experience in a particular industry or across several industries? Was the mentor typically focused on consumer-focused products or business-to-business products? Was the product an end user focused product or a platform on which others build end user products?
Geography
While modern day mentorship allows founders to meet mentors anywhere in the world, geography still plays an important role in a startup journey. That's why it's important to consider geography as you're researching your mentor. For example, someone building a startup in San Francisco will have a different experience from someone building a startup in Amsterdam. Was the mentor's company focused on a global customer base or focused on a specific geography? Did the mentor start and build the company in a location that would provide interesting insights for your company? Did the mentor build a remote-first company or was the company anchored to a specific location? Is the mentor currently located nearby or will the meeting be virtual? Is the mentor located in a time zone that will make finding a meeting time difficult?
Networks
Part of the value of engaging with mentors can be gaining access to the mentor's extended network of colleagues and peers. Make sure to research whether the mentor has specific networks or areas of influence that may be valuable to you or your company. Did the mentor attend a well-known university or business school? Where did the mentor work prior to founding their startup? Was the mentor a participant in an upper tier accelerator program? Did the mentor receive investment from name brand venture capital firms? Does the mentor belong to professional networks that provide some insight into their area(s) of expertise?
Personality
While this can be difficult to determine without meeting the mentor, you can often use clues on social media to help provide some insights into your mentor's personality. This can also be a good way of identifying other areas of commonality between you and the mentor. Does the mentor participate in social media or are they fairly quiet online? Do they tend to focus energy on sharing more personal content or more business content? Do they tend to travel or remain in one place? Are they more likely to express themselves in long-form posts or short snippets?
Use various resources to do your research
With the popularity of startups and startup founders, it's likely that there's information about your mentor to be found online, whether that content was created by the mentor themselves or covered by traditional media. Use every resource at your disposal to gain a better understanding of your mentor, their areas of expertise, and other insights that ensure you can make the best use of the limited time you have with them.
The more knowledgeable and prepared you are for the initial meeting, the more likely that both you and the mentor will find that meeting valuable and worthwhile. This, in turn, sets positive expectations for future meetings and an on-going relationship.
For business professionals, LinkedIn tends to be the predominate source of relevant information. Using LinkedIn as a research tool, you can answer many questions about the topics above, including experience, geography, networks, and to some extent, personality. Use the mentor's LinkedIn profile to gain a better understanding of where the mentor has worked, how long they were at their startup, which networks they highlight, and the type of content they share.
Google or other search engines
Search engines can be an efficient means of finding other social media profiles, content the mentor has created, and stories, articles, newsletters, and podcasts featuring the mentor. Spending time researching insights the mentor has shared in media or on a personal site can be a great way of gaining a base understanding of the mentor's perspective. It can also be a guide for forming more nuanced questions for your mentor meeting.
Tip
If the mentor publishes a weekly newsletter on specific topic, it's safe for you to assume that asking that mentor for nuanced advice on that topic would be a valuable use of your and their time. But you might not realize that newsletter exists without doing your research.
Just as important as the content, itself, are the number of times the mentor appears in context with certain topics. Are they referenced as an expert in leading publications about a particular topic or startups in general? Have they had certain experiences—positive or negative—that have been covered in the news? Pay attention to the topics they regularly discuss and how they discuss them.
Social media
Finding a mentor on social media is another way to gain a better understanding of their experience and personality. Social media may provide insights into the topics that a mentor is most comfortable discussing. Or it may simply provide insights into the mentor's personal interests. Either way, social media can be a valuable resource for gaining a deeper understanding of your mentor, ahead of meeting with them.
Crunchbase
If the founder raised venture capital, using a resource like Crunchbase can also be an efficient way of learning about the mentor, their company, its products, and investors who funded the startup at various stages. It can also be a good way to determine whether the mentor has raised venture capital.
This can be a key differentiator for where you steer the conversation. For example, if you're a founder who is interested in potential ways to fund your business, then asking a mentor who bootstrapped about VC may need to focus on reasons why they didn't pursue VC, rather than how to pursue VC.
Next, let's take areas you know you need help and compare them to the areas where your mentor could be helpful.