Once upon a time (well, actually many times over decades!), I was a mentor in a national program that paired experienced executives with up and coming business leaders. My first mentee in that program, Colleen Larson, and I have stayed in touch over the years. Along her life journey, Colleen demonstrated her own boldness in the decisions she made, the roles she took, the teams she built, and the results she delivered. She, like me, like many of us, believes in helping others find their boldness. She went from mentee to mentor in that same program and was paired with another clearly bright, high potential mentee, Diana Rehnberg.Diana-Rehnberg

Today Diana is the Second Vice President, Business Intelligence and Analytics at Travelers. When we sat down together, before we got into any conversation of what it means to be a bold leader, we reflected on that mentor to mentee thread that has connected us and so many others we met through supportive, nurturing relationships along the way. Context or operating environment, unwritten norms that exist in any organization, and relationship building are common conversations between mentors and mentees. They were also key themes through my bold leader conversation with Diana.

Reflecting on several companies she has worked in, Diana noted the significant differences between them while giving examples of how you can be yourself and be a bold leader – if you learn how to read the environment, identify unwritten norms (those you will abide by and those you will actively work to change!) and build the right relationships.

Example one: Large and dynamic

Context: It was expected that you would drive change – a very fast paced, demonstrate your ability to see and seize opportunities, kind of organization.

Unwritten norms: Focus, move and “pick your battles and best opportunities;” never settling; “Don’t wait to be asked – move yourself and your team forward,” Diana explained.

Relationships: Build a team that is movement oriented. Identify and cultivate the people that can make things happen. Diana says, “Be very deliberate about the composition of the people around you – a real mix of skills, perspectives, and experiences.”

These were all base skills Diana had but was able to develop and hone in this first context, and they are skills that still define her bold approach today.

Example two: Entrepreneurial

Context: “I only had to convince one guy.”

Unwritten norms: Make your case and go! You’re on your own to succeed or fail.

Relationships: “I love a roadblock.” (The old “never waste a crisis!” perspective.) “I am an optimist; I know I can figure a way around and I pull people in beside me who have that same orientation, who will challenge me and may have better ideas. And I like to have a ‘steady Eddy’ on the team too, to keep us grounded.”

In an entrepreneurial context, you don’t have the resources of a large organization and roadblocks are plentiful, so being creative about where you find ideas and support is a lesson Diana learned and carries forward from this example.

Example three:  Legacy writ large

Context: It takes a village. The near opposite of example one, this is an environment that is steeped in tradition and legacy, and where (unlike example two) you almost never are on your own to lead opportunity development.

Unwritten norms: Trust is earned. Know and respect past successes and take the time to “build consensus and understand the implications of any change on others.”

Relationships: Interestingly similar to the other examples, you still need advocates, a dynamic team, and close confidants that will test, support, and encourage you. Diana reflected, “I like to see change in my team, purposely orchestrated movement to bring in fresh perspectives, to give team members opportunity to move and grow.”

I have led a number of change initiatives working in and with organizations that are carrying what I have labeled “trailing history.” As I listened to Diana talk about this third example, it reminded me of how important it is to have bold leaders in these organizations who respect the history but are not tethered to it, so that they can help the organization keep what is important and shed what is needed to build the next great chapter.

Diana’s three examples are great reminders that mentoring, finding the future bold leaders with the innate orientation and skills, nurturing their development and honing their leadership abilities is a must in any and all organizations.

What are the most valuable lessons you have learned from a mentor? How about lessons you’ve learned from someone you are mentoring?