These Leading Thoughts are for senior leaders, and this means that each of us is likely to have extremely capable people at our side, making our vision possible. I certainly do. My Executive Assistant is Karen Montgomery, and she is an amazing gift. She is far over-qualified for what she does for me but she puts her gifts in harness with the rest of our team to help us achieve grandly.

In fact, she is so important to me that I’ve asked her to write my next few Leading Thoughts. How should you relate to your EA? How and when should they deliver difficult news? How do they “stand guard”? Well, Karen is going to address all of these matters and more. You might want to pass these along to those you work with. There’s a lot of wisdom coming your way! Enjoy these. Use them. They’ll make a difference to your leadership. Thank you, Karen.


Stephen has written in previous Leading Thoughts about knowing and being able to articulate your leadership style. Some, like Stephen, lead best as the “out-front senior leader.” Others, however, lead best behind that senior leader. It might be because they have a certain specialization that falls within the scope of the organization, or that they are bent more toward organizational leadership, or perhaps they are a younger leader, still learning the skills of good leadership. This Leading Thoughts is written for them—which might include you.

Whichever of these categories you might fall into, you are not the one who is the face of the organization but you are essential. If we call the senior leader #1, then to be successful they are likely teamed with some #2s. As a #2, you are probably a leader as well, but let’s consider for a moment what your relationship with your senior leader, your #1, should look like.

In addition to your everyday responsibilities, and perhaps even more important than those, your job is to help your #1 succeed. It’s to help them put their best foot forward for the good of all. It’s to be watchful of potential pitfalls, possible public misperceptions, to have one ear tuned to the leader and the other turned toward the rest of the organization and beyond.

Your job is to listen and sometimes be a sounding board for ideas, and then to hold them carefully, but lightly and wait for the wind of time to sift them. When the moment is right, give that idea wings and help it fly!

To serve as #2 takes wisdom and some emotional intelligence. Develop these and be a student of your #1. Learn how they think and what’s important to them. Give them feedback when it’s needed. Anticipate their needs. Which problems or decisions can you handle and which will your senior leader want to weigh in on? Do they think best after 2 cups of coffee? Should that meeting that may become contentious be scheduled early or late in the week? Do they like “big numbers” or full detailed reports?

And finally, as #2, remember who you are. When you’re around others, be sure to honor your senior leader in word and deed. You may disagree with them in private, but not in public. And be humble. Though there may be times you feel you could do a better job, the truth is, you are not in their shoes, and you may not know everything they know. If the time should come that you are placed in a senior leader position, you will want a similar person of character in the #2 seat.

Stephen’s mission statement is, “Your destiny is fulfilled by investing in the destinies of others.” Help your leader fulfill their destiny. You might be surprised how the pieces fall into place for your own dreams as well.