The Art of Project Management: Expert advice from experienced project managers in Silicon Valley, and around the world

It’s Just Lunch – Asking an Executive to Mentor You

Table of contents for Getting and Making Good Use of a Mentor

  1. Still Don’t Have a Mentor?
  2. From Mentor to Colleague
  3. Mentoring Circles – Better Leveraging a Mentor’s Time
  4. It’s Just Lunch – Asking an Executive to Mentor You

Some of the best mentoring I’ve ever received is from executives. Even when I was a mere pawn in the corporate chess game I longed to understand the game from the view of the king. Working in the basement of the building which is now the Facebook headquarters, I mostly had a view of the shipping and receiving dock. Although I had plenty to do in the bowels of what was then an analytical instrument manufacturing facility, I found working without a clear vision of where we were headed as on organization unsatisfying. And in my state of youthful exuberance I was truly convinced that I could make a meaningful difference to the success of our organization if only I knew what the goals were.

With no mortgage to pay and no kids in college, I was free to take some chances, so one day one of my scrappy gal pals and I invited our new division manager to lunch. He must have thought I was incredibly brazen, because he was moderately feared by some of the more timid souls in our midst, and I know he was incredibly busy. But he agreed to meet with us over lunch, and that was a real turning point for me. First of all, he paid for lunch, which was a nice bonus. In addition after that I really felt committed to doing my part to make our business successful. Here’s how we managed to get him to be a “micro-mentor” for us:

  • We told him we admired his leadership style.
  • We asked him to help us understand his goals so we could be more supportive of him.
  • We promised that we’d pay back his time invested in far greater productivity if he met with us.
  • We only asked him for one meeting. And we never used the word “mentor”.
During lunch we listened enthusiastically to his stories, asked him open ended questions, and told him (more or less honestly) what we thought about his effectiveness as a leader since he took over our division. And we asked him what we could do to help him successfully lead our organization. We must have seemed a bit naive, but I guess he wasn’t used to people listening to him with sincere interest, or sharing their opinions openly without their lips in a puckered pose, so he spent more time with us than planned, and even offered to do it again sometime. It was amazing how much more connected I felt to our business after that. I was inspired for months, and I always felt some kind of meaningful connection to “management” after that.

Of course one lunch with a senior exec can’t make up for a multitude of assine behaviors by other people in the work environment, but getting a chance to talk 1-on-1 to your senior executives can change your perspective on your place in the corporate hierarchy. This is especially true if you are fairly junior. In fact, I believe that the fact that we were so junior is what made it so easy for us to ask, and for him to say yes. We really had no power in the organization, and weren’t a threat. We had no hidden agenda. We were just two scrappy women in search of our place in the business world.

If you want to benefit from some face time with your execs here’s one approach that might work:

  • Just ask for one short meeting.
  • Tell them you are committed to helping them achieve their goals, and you’d really benefit from hearing their vision directly from them. (Make sure you are sincere. No BS!)
  • Listen Enthusiastically.
  • Follow Up Graciously.
You could say something like this to your division manager, for example: “Jared, I’ve been working here for just about 6 months, and I really like the way you’re leading this division. My manager has shared your strategic plan with our team, and I’ve read all of your messages about our direction, but I’d love to hear your vision from you directly. Would you be willing to spend 15 minutes or so over a cup of coffee sharing your view of our future with me? I promised I’ll make it worth your while by making sure my work is aligned with the direction you’re setting.”If they’re busy trying to save the company from bankruptcy, or staving off hostile takeovers, they might have to turn you down, but most executives will have a favorable impression of you after a sincere invitation like the one outlined above.

Oh, there’s a possibility that your manager won’t be quite so thrilled with your meeting. If you’re working with someone who sees your initiative as a threat you can diffuse that by inviting them along. Try it! The worst that happens is you’ll get rejected, then fired, lose your home, and your kids will have to go to community college.




About the Author

Kimberly Wiefling is the author of one of the top project management books in the US, "Scrappy Project Management - The 12 Predictable and Avoidable Pitfalls Every Project Faces", and the founder of Wiefling Consulting, LLC, a scrappy global consulting enterprise committed to enabling her clients to achieve highly unlikely or darn near impossible results, predictably and repeatedly. Her work focuses on keynote speaking and workshops on practical and sensible business leadership and project/program management scaled for the size of the company and the project. She has worked with companies of all sizes, including one-person ventures and those in the Fortune 500, and she has helped to launch and grow more than half a dozen startups, a few of which are reaping excellent profits at this very moment. She spends about half of her time working with Japan-based companies that are committed to developing truly global leaders. Kimberly holds a B.S. in Chemistry and Physics from Wright State University and a M.S. in Physics from Case Institute. She spent 10 years at HP working in product development project management and engineering leadership. She worked with several startups, including a Xerox Parc spinoff where she was the VP of Program Management. In 2001 she launched her consulting practice and never looked back. She holds a certificate in project management through UC Santa Cruz Extension, where she is an instructor in the Project and Program Management Certificate Program. Kimberly spends about half of her time facilitating leadership, communication and execution excellence workshops for leaders of Japanese companies committed to becoming truly global. Thousands of people have viewed the hysterical video documenting the final phase of completing her book at You can reach her via email at
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