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Short-term vs Long-term mentorship - what's right for you?

“A short-term mentorship is like an emergency number you call when you need help to resolve something quickly. Long-term mentorships are more akin to an explorer and sherpa relationship where the sherpa is the expert here to guide the explorer (mentee) down the long path to success.”- Lloyd Jacob
Lloyd Jacob

I am a 5x Founder, Y Combinator Alumni, Product expert & Active Mentor to startup founders. I speak SaaS, Advertising, Product Development and Startup Success., Keywony.com

Most people if asked what a mentorship program is, will say it’s a relationship wherein one person who is experienced (mentor) will help another person or team (mentee) with less experience. The value proposition is clear. The mentor can pass along his/her hard-learned knowledge and experience to the mentee to help them succeed. While the mentee gets a ‘sherpa’ who can help guide them through challenges, teach strategies, and pass on knowledge to accelerate their businesses, career or personal growth.

Everything I mentioned so far is the dictionary definition. The reality is, the mentor & mentee relationship is defined by the mentee. The mentee can use the mentor for short-term help they need or develop a long-standing relationship. The use case is different in each. 90% of the mentees I work with have been short-term relationships (1-2 months), the remaining 10% stay with me for a year on avg.

How a long-term mentorship relationship develops:

To be open and honest with a stranger is not easy for most mentees. I’ve noticed most mentees (90%) will get straight to the point and want me to focus on their main point. Sometimes, I feel like Quora.com, where they ask a question and expect a 15-minute in-depth answer. This can continue for weeks this way. However, with some mentees, after we build a relationship over a few talks, they relax and open themselves up. This is the pivotal point where the mentee realizes the mentor is trustworthy and they can be vulnerable with the mentor. From here on out everything changes.

Let compare the conversations in a Short-term vs Long-term mentorship.

In short-term mentorships, we discuss:

  • How do I know if my idea is good?

  • What do you think of my idea?

  • I want to build X, but I am not sure how to start.

  • I am not sure if I have product-market fit.

  • How do I get my first few customers?

  • As a single founder, what is the most important thing to focus on right now?

  • I am not technical, should I find a tech co-founder?

  • I need advice on applying to Y-Combinator

  • How do I get started raising money?

  • I am a Product Manager; how do I convince my manager about my idea?

  • I am a student and want to get into Product Management; what’s the best path?

In long-term mentorships, we discuss:

  • I’ve been trying to grow, but growth is stagnant.

  • I am running out of money. What should I do?

  • I’m stressed out. How do I relax?

  • My co-founder is not putting in the same level of work as I am. What do I do?

  • How do I update my investors regularly?

  • I have an X family issue. Should I take a break from my startup?

  • How do I plan my personal life and work so that I pay attention to what is important?

  • Money stresses me out. If I become successful, will it change me and my passion?

  • I want to plan a 1-year goal for my business, How do I do that?

  • How do I create the right KPIs for myself and my team?

  • I am growing; what should I be doing as the founder to plan ahead?

I hope the above provides insight into the two types of relationships. Most of my longer relationships have developed out of short-term engagements and that’s rightfully so. The mentee needs time to determine if the mentor can be trusted with the inner details of the business and their personal challenges.

I feel long term mentorship provides the best value to a mentee. I’ve been on the other side; it’s a place where you can easily live inside the box, be happy coding all day and never taking the product to market, feeling depressed that time is passing with little impact to my KPI and sometimes simply feeling down because nothing seems to work. A skilled mentor can look at these behaviors and surface them. Rather than being complacent, they can push back and shake things up to get you into the right zone. A long-term mentor does this on an on-going basis to help the mentee grow in addition to providing all business, technical or marketing knowledge.

If you are looking for a long-term mentor, read this…

Always start with a short-term relationship. Be clear and set a 2 month relationship. Don’t expect to gain real depth with a mentor in 30 days. 30 days is more for when you need the mentor to give you help/guidance/feedback on an immediately concerning task/issue. During the 2 months, plan to meet once a week or twice in 2 weeks. Ask if the mentor is flexible in their schedule, if they are, it’s a good sign because they can be there for you when you need help.

Use the 2 months to gauge the mentor by asking yourself the following questions:

  • when we started, did they try to ask the right questions?

  • does the mentor pay attention to me when I talk? Do they listen, or are they barking their knowledge at me most of the time?

  • does the mentor agree with everything I say or do they push back and make me rethink my ideas/opinions?

  • do they ask me questions to learn about me, my drive, my passion?

  • do they ask questions to help me rethink what I thought I knew?

  • is the mentor honest about their success/failures? Does the mentor sound pompous?

  • do they have the experience to handle my problem? What experience do they bring? What are they not experienced in?

  • is the mentor experienced in taking me 1-2 steps ahead or are they miles away and thus not understanding my problems?

  • are they getting to know me better each time or am I just a person at the DMV line who they help getting a task done?

  • is this someone I can have my team talk to?

Once you reach the 60 day trial period, review the above questions. After answering them if you feel great about your mentor, extend that relationship. Talk to the mentor about creating a long term on-going relationship. Express why you are extending it, what you experienced in the 60-day trial, why you picked them, and what you would like from the mentor going forward. However, if after reviewing the above questions, you don’t feel so positive, drop the mentorship. Thank the mentor for their time and part ways positively.

Your search starts again…

Lloyd Jacob


T: https://twitter.com/malulloyd

I: https://www.instagram.com/lloyd.jacob/

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