At a recent Art of Leadership event, broadcaster and anchor of ABC’s Good Morning America, Robin Roberts, talked about the importance of finding your quest – finding your definition of success or that place you are when you are at your best.

The middle years of our careers are, at best, the time when we take chances, learn what we like to do, and develop the network and resume that will support progress toward our aspiration. For many of our employees that time is more of a random navigation of assignments in the hope that our general trend will be toward more senior positions.

As mid-level employees and managers, we should take a more proactive view of how we progress. Equally important, as genuine leaders we need to help their people navigate that process.
Think of it as crossing a stream without a bridge. There are many rocks you can step on to navigate your way across. How do you choose which rocks to reach for?

Using this analogy, one approach is to consider each rock in the context of whether your other foot will be on solid, dry ground when you reach out to take that step. If your left foot is solidly planted on a nice dry rock, you can reach out with your right foot a long way to successfully get to that other rock. If your left foot is already in a wet, slippery spot, you are very likely going to miss the other rock or land on your bottom in the water in the attempt. And in the same analogy, if you decide to just leap for a rock with neither of your feet firmly planted, the risk that you will land in the water is very high. That doesn’t mean you shouldn’t jump for a particularly shiny rock, but you need to know the risk before you leave the ground.

You can apply the same thought process to mentor your mid-career leaders through their development choices.

Early in my career, before cyber security was even a thing, I found myself leading a cyber security project in a major bank. When I was approached by a global consulting firm to develop a cyber security practice, my initial reaction was to decline because I had never worked in consulting. Then I realized that one foot was firmly planted in the security experience I did have. That gave me the leverage I needed to take the far-reaching step over to the consulting rock. Within five years I was a recognized speaker and author in the then recognized security sector, and I was leading a specialized global practice.

Fast forward to a few years ago, when I decided to write a book that would bridge technology issues and concepts for non-technical executives and directors. I was able to demonstrate to my publisher that I can stand firmly on my experience writing and speaking to support my authorship habit. There have been many rocks, and slips, along the way, but where I took the time to understand the current and terrain of the river I was generally able to catch my footing and build on my capabilities.

Specific guidance as you coach your employees:

  1. Pick a spot. Encourage them to identify the specific skills that they want to develop. Encourage them to get input, and support them as a sounding board but make sure that they own the sorting. While it is absolutely appropriate to use mid-career changes to test out different experiences, each change should be directed toward some specific quest.
  2. Don’t try too hard to make it fit. Encourage them to map out their stepping stones as they go and then use that map to guide each next step. They should be able to see themselves successfully landing on that next rock. Moves for the sake of the money notwithstanding, their map will help them to avoid unintentional sideways or backward steps.
  3. Listen to the questions as much as the answers. A rule I learned early in my career was ‘never show up to a meeting without a notebook and pen. It is disrespectful because it suggests that you do not expect to get anything notable out of the conversation.’ Help your mentee understand that it is important to listen to the questions they are asked as much as the answers they get to their own questions. Suggest that they make notes that they can review what their mentors may see as opportunities for focus or improvement. Making notes also shows engagement in the conversation, which helps to solidify the relationship. Finally, notes let them map each new insight against what they want from mentorship or a change. Encourage them to keep a career planning book and actively develop their insight over time – I still have mine from the early 80’s and it is one of my best guides when I am assessing that next rock in the stream.

Experienced mentors know that there is no magic insight. We are generally all doing our best based on what we know at the time. Our real value as mentors will come down to whether or not our mentees find the foundations and support that they need to successfully navigate their careers.



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