How to ask for mentoring


I get a lot of email from people who want advice. I usually reply. Sometimes I get an email from someone who is clearly a pain but I’m impressed that he or she asked for help, so I answer. Sometimes I get such a good question from someone that I actually give him or her a call.

I learn a lot from answering peoples’ questions. First, I learn about how to ask for advice because I can listen to how people do it to me. Second, the more I hear myself give the same advice over and over again, the harder it is for me to not take it myself.

Here is an example of someone asking for help in an effective way: She sent one of the thirty press releases in my in box that week. I was interested in a few of her assumptions in the press release, so I emailed her. She wrote back lame answers. I ignored her. Then she wrote an email asking me how she can do better at addressing the press. She asked three, very specific questions. I was impressed at how well she asked me to help her. I made a note to myself to ask such good questions. Then I called her to give some advice.

Here is an example of a different exchange, but one that I have all the time:

Me: “Did you know that outside of schooling, the quality of your network of mentors is the most important factor in how successful your career will be?”

Other person: “But how do I get a mentor?”

Me: “You read a lot and find people you want to be like and send them an email.”

Other person: “What do I ask?”

Me: “How that person overcame the specific hurdles you see yourself facing. And what advice they would give to you to get on a path to achieve what they have.”

But to be honest, it’s not like I do this all the time. So, like I said, the more I give advice the more likely I am to take it, and finally, I decided to try contacting someone I read about. She got a big columnist position that is not in my genre, but the person seemed like a real go-getter and I like her writing. So I emailed her to ask if she could give me some career advice. I sent her some sample columns and I made a little joke about how even the career columnist needs career advice. After all, humility and humor go a long way in getting someone to want to help.

She replied to my email ten minutes later. I couldn’t believe it. I rarely respond to my emails that fast. I decided she was very organized and on top of things and she would really have a lot to teach me. I got excited. And then I got nervous that I wouldn’t have good questions, or that I wouldn’t know how to steer the conversation. So I didn’t call her for three weeks.

Finally, I called. She was so incredibly useless that I can’t believe she writes an advice column. She said she had no career plan for herself. She said she just fell into everything. She said she just lives day to day. I don't believe any of that. She fought too hard to get where she is.

But you know what? I felt great after that call. I felt great that I took action to get a new mentor, even if it didn’t work. I felt great that I read about someone and talked to her. That’s what people should do, and I knew that after having done it once, I would do it again. It wasn’t difficult at all.

23 replies
  1. Ryan Cooper
    Ryan Cooper says:

    You say “I don't believe any of that. She fought too hard to get where she is.”

    There are really 2 possibilities here, and it seems you’ve only considered the first one:

    1) She is lying to you for reasons unknown.
    2) You are projecting your view of and assumptions about career-building on her. She is telling the truth, but it doesn’t make sense to you because it doesn’t match your assumptions.

    It seems like you are saying it is unfathomable for someone to have success without “fighting hard” for it I strongly disagree. My experience has been that those most focused on “fighting” for success are the least likely to find it.

    Perhaps you mean something different by “fighting” than I do, but it seems to me much easier to lead a successful career by cultivating relationships with interesting people that you like, waiting for interesting opportunities to fall into your lap, and pouncing on those opportunities. This does not require a career plan. Reality has a way of differing from plans, so going with the flow and adapting to reality are often much more useful than following a plan (and trying to force reality to adapt to it). Often a plan only gives us an illusion of control, and blinds us to opportunities we didn’t plan for.

    This way of looking at things has certainly worked for me thus far (I’m 26 and run my own software development consulting business), and I suspect it has worked for many others as well.

    Perhaps I’ve misinterpreted your words. I hope you ‘ll take the time to share your thoughts on what I’ve written.


    * * * * * * * *

    Hi, Ryan. I understand what you’re saying. So much of life is being at the right place at the right time. And you’re right that if you forge relationships with interesting people, and do good work, surprising things fall into place.But there are some things that are very, very competitive. And they don’t fall in laps. The stuff that is very competitive takes some planning to achieve. It will always be about timing, but when competition is heated, it’s preparation, as well. You have to be prepared for that door to open so you can walk in.  

    That said, this woman probably is not as tactically oriented as I am. It’s a good lesson, I guess. To not assume that everyone thinks like me. That’s a good thing about the conversation on the blog. The comments section is great for giving the other side of things. Makes me smarter about everything. Thanks :)


  2. RM
    RM says:

    I have tried asking this question to multiple people who are what/where I want to be. The biggest problem is getting back very common words of wisdom. The times when I got good advice or feedback is when I know the person at a deeper level than just their name. If the person connects with you, there is true sharing.
    And as Guy Kawasaki says, about mentoring, there has to be a reason why the person wants to mentor you. Teachers are a big exception to this rule but then their advice is generic too for the first 2 times you meet them. It is only with the say 3rd or so meeting that they know you are genuinely interested and they try to learn more about you.
    There might be a way to ask the right question and set the right framework for a quiky kinda interview. But I have not mastered that art yet.

  3. Sarah
    Sarah says:

    I agree with Ryan on this one, Penelope. I heard this really inspiring business woman speak about her career recently. She was obviously competitive and driven to have achieved what she did, but she said that she’s never had a career plan as she believes it blinkers people to the other opportunities around them.
    She compared it to being a trapeze artist. You have to always be ready to shift your focus at a moment’s notice to grab another bar that may be within easy reach but just out of your line of vision. But you only have a split second to react and if you’re too focussed on that one distant bar, then you risk missing all these other opportunities. I thought that was really inspiring, all the more so because it was counter intuitive.

    But saying all that, I guess that anecdote also fits in with what you said in your comment above about planning, and being prepared for the open door. Hmm. Maybe your mentor-that-wasn’t doesn’t define this kind of preparation as career planning??


  4. Jacqui
    Jacqui says:

    I had a similar experience once, when working on a college project. I had read a book for the project that I truly enjoyed and bought into whole-heartedly, but I needed more information.

    So I did some research, found some information on the author (a professor at Carnegie Mellon), and e-mailed her to ask her my questions, along with telling her how much I enjoyed her book.

    Not only did she willingly answer all my questions, she was very grateful that I had taken the time to tell her how much I enjoyed her book.

    I learned that you can never assume who will feel too busy or too important to deal with your questions, and that most of time all you have to do is ask.

    (By the way, the book is called Women Don’t Ask: Negotiation and the Gender Divide by Linda Babcock and Sara Laschever – it’s a must-read for any professional woman and completely changed the way I view business and many other aspects of my life.)

  5. Denis
    Denis says:

    “But there are some things that are very, very competitive. And they don't fall in laps. The stuff that is very competitive takes some planning to achieve. It will always be about timing, but when competition is heated, it's preparation, as well. ”

    Some people have such an enormous talent in their chosen field that it is hard for us mere mortals to comprehend how one can be that successful without conscious planning. However, people are not created equal in their intellectual or charismatic abilities and sometimes no amount of hard work, learning, planning, self-improvement and preparation can beat a person whose creativity naturally express itself.

    I’ve seen people in academia making careers by finding good advisors, smartly chosing hot subfields of study, netowrking/collaborating with the right people, thinking through their presentations etc. They WORK on their careers, they do very good research and they reach close to the very top, getting tenures at the most prestigious universities. At the same time there are other people who are so talented that they reach the same heights (and more) without any planning. Sometimes, their enormous talent doesn’t require collaboration with the right people, or anyone at all for that matter; sometimes their ideas inspire other people to work with them and help them.

    I am sure the same types can be found in other fields, too. Some people build their careers, some get lucky and some — “naturals” — just know intuitively the path to success.

    Often times, these last ones are not consciously aware of what they do right and how they do it. Their success comes to them almost as naturally as breathing. They can’t teach other people how to successfully build a career because they are too different and can’t relate to the regular person’s mindset and experience.

  6. Amy
    Amy says:

    Thank you for letting me be one of the many who asked you for advice this past week. Reading your blog today on doing just that is a bit surreal. I’m thoroughly grateful for your presence as a mentor to all of us readers every day. No muss, no fuss – just your true opinions.
    – Amy Vachon

  7. Sia
    Sia says:

    Some professional societies like ASME ( provide electronic mentoring to students or entry level graduates, They hook them up with an experienced professional to be couched. it is very useful and very reliable

  8. zen
    zen says:

    Oddly enough I read about your blog on another blog, but stumble on your blog when I start researching my plans for searching for mentors.

    I agree with what you say, but also it was very inspiring – just one of those slaps to the face that pushed me to seek out and finally email the people I’ve known but just haven’t contacted about being my mentor.


    hello my name is stephanie blakemore and i need help to write a resume for a a good person to work with.i work at sheraton hotel for 6 years and i trying to get out of restaurant business and trying to do something different with my life.i did supervised,cashier,room service.but i still want to work with customers because that what i like to do.can you help me to do resume

  10. George Eastman
    George Eastman says:


    There’s this role model that I absolutely admire and want to mirror. He’s the CEO of 3 companies and have 5 kids. He does not know me. I’ve met him once at a conference, shook his hand and took a picture with him.

    I’ve dropped him an email before, but I assume he is too busy to reply (or someone else checks his email–secretary perhaps).

    Should I try writing him a snail mail? Include a print out of the picture so that we knows we have met at least once, and basically, follow the steps above you mentioned, asking for advice on getting through similar hurdles that he did?


  11. Kathleen
    Kathleen says:

    This story reminds me of something that happened at my office. I work for a company with annual revenues of $10 billion. I’m a finance manager for one of the business units in the company and I was talking to a someone who works for me. He was looking for ways to help him create growth in his career. I told him he needed to start networking with other people, including those in top positions in the Company. He was surprised by my advice, but decided to give it a try anyway. So, he sent an email to our CFO thanking him for increasing the participation in our annual financial offsite, because it allowed him to attend whereas he wouldn’t have been invited before. Not only did our CFO invite him to lunch, but they have had numerous lunches since then.

    I think this example shows that you can’t be afraid to step out of your normal boundaries, because you may find that networking with the right people can help a great deal in your career growth.

  12. ET
    ET says:

    Kathleen’s comment echoes an important point you made. We need to stretch beyond our comfort zone. Sometimes we know what we ought to be doing. We have heard it; we may even have advised others to do it. But we haven’t done it ourselves (or we haven’t done it recently, or we haven’t done it enough).
    Successful people make a habit of doing those “uncomfortable” things.

  13. Cheryl
    Cheryl says:

    I love your blog posts – I’ve been rummaging around since my own departure from my former employment of 7 1/2 years…

    I like the premise, but what are the characteristics of a good mentee? Everyone wants good mentors, but sometimes, I wonder if the mentors want the mentees. Just a question…

  14. Jessie Rasche, artist
    Jessie Rasche, artist says:

    Thank you for the article. I’ve been wanting a mentor for a couple years, but the whole idea of actually contacting someone has been… I just don’t know what to say.

    I am an artist, and what I really want is another artist whose work I love and respect to look at my work and tell me where I’m lacking / where to spend my energy. But that seems like a big thing to ask for. How would I make that worth the mentor’s effort?

    Thank you for the post!

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