4 Mistakes that Kill Mentoring Relationships

by Jeff Keltner

I’ve been very lucky in my career to have a number of great mentors who I could turn to for advice – and they have been invaluable. At Upstart, we believe that good mentors can make a tremendous difference in your career. However, we also see a lot of people struggling to figure out how to develop effective mentoring relationships. It is important to remember that these relationships grow and evolve over time and each one is unique. While there is no single path to having great mentors, here are a few common mistakes to avoid.

You ask them to “be a mentor.” Most people are happy to give advice and share their experience. However, the request to “be a mentor” is very poorly defined and can feel like a big commitment. Instead, start with a small, specific request – usually asking for some advice on a specific topic they have experience with. Then, continue to engage them more over time and grow your relationship. By keeping the initial ask simple, you make it much easier for them to say yes and get to know you.

You don’t make it easy to help. When you ask them for assistance – make it easy for them to help. If you want an introduction, make sure you are clear on whom you want to speak with, why that is the right person to talk to, what you want to discuss, and what you hope to get out of the conversation. No “do you know someone at Google who might be interested?” Make the request directly, and once they’ve agreed send an email that includes everything they need to tell the person – something they can simply forward with the brief personal request added. Don’t make them do the work of finding the right person, explaining your question/business, etc – make it easy as possible for them to help you.

You ask the wrong questions. If you’re asking for advice, spend some time thinking through what exactly you want to ask and why. Don’t just send a long essay about your current situation and ask “So, what do you think?”. Have a specific question you’re looking for guidance on (you can have a couple, but no more than three). Also, keep your questions open-ended and never ask them to make a decision for you. For example, ask “What key factors would you think about in deciding between these two roles?” not “Which job should I take”? It’s far more valuable to understand how they approach a problem than to be given an answer because you’ll learn more from it.

You don’t keep them updated. Once you’ve begun to develop the relationship, make sure to keep them updated on how you’re doing. If they give you some advice – let them know what you end up deciding and how it turns out. If they made an introduction, let them know about the meeting and the outcomes. Send out a regular update (timing varies a lot, but think monthly to quarterly depending on how much is going on). You’ll be surprised how often you get great advice and introductions when you’re not even asking for them just because you send someone an update and they have a relevant experience or contact.

Mentors can be an amazing resource in your career, so invest some time in finding and growing these relationships. They take time to truly develop, but they are well worth it. We will be working to incorporate these concepts into our product as we build out mechanisms for upstarts and backers to interact. Please let us know if these tips are helpful for you, or if you have others to share! - See more at:

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