We’re doing some thinking about leading your leader. Senior leaders have a unique blend of gifts and dysfunctions (as we all do). This requires those in subordinate roles, if you will, to take that into account when working with them. In other words, you have to pay attention to “how” to lead your leader. You might want to read the first part of these musings here.

With this in mind, what can people do to both inform and challenge their leaders, while at the same time avoiding the sharper edges or soft spots (choose your metaphor) of the leader. Because, here’s the deal: APPROACH MATTERS. So…here are some ideas…


Questions, honest and forthright, are a great way to lead your leader. Questions also create options–which most leaders like AND which invites them, NOT YOU, to make choices. (By the way, getting them to make choices requires that you have done some work first: designing the options for them. More on this in an upcoming post.)

Let’s say that your leader continues to pile on the projects without much regard for what he or she asked you to do yesterday. You probably don’t want to say, “Look, knock it off, I’m maxed out here and your inability to prioritize is not my problem.”

A better approach is the question/option method:

Boss: I really need you to get right on this new X project

Me: Got it. Let me ask you. I’ve got four major projects out there right now. Project B and C are in the early stages. And of course, because of the importance of the initiatives tied to both of them, I am giving them my best energy. Also, project A is going to need my attention for the next two weeks as I hand it over to Sarah. I would say I have about 10 hours of work to go to finish project Y, and let me tell you, project Y is already making a difference. I want to make sure we finish it strong. So, I’m curious, in your mind do you see this new project, project X, trumping all these other projects from a time and energy standpoint?

Now, you might be thinking. Wow. That’s an awfully long response Dave. My boss probably doesn’t want to know all that. Well let’s see, read the response and time how long it takes. I just did it and added a few words here and there and came up with 35 seconds. I think anything under 60 seconds is OK. The problem is when you OVER talk about your time and energy constraints, not when you talk about them in the first place.

Allowing your boss to understand your world is part of leading her. Giving her options allows your boss to take a bit of accountability for her directives and can create more realistic expectations between you.

Let’s say you are dealing with a troubled employee and you need to bring your boss into the loop on it. DON’T wax on and on and on and on and on and on and …. about it. Present the issues, with some narrative examples and then: PRESENT OPTIONS. Do the hard work before the conversation. Give your boss your best thinking before you get in the room. Then, your conversation with him/her can be used to refine that thinking and choose a course of action.

Let’s say you are waiting on your leader to accomplish “something.” She’s not doing it. She’s late getting it to you and it’s holding up the team.

You: Hey Jim (your leader) do you have document X done?

Jim: Oh man, I don’t. I’ve just been swamped and to be honest, I really don’t have time for stuff like this. I mean, I know it’s important, but I just have to much to do.

You: I hear you. Let me ask, would you like me to take a shot at drafting the document, or would you like to set up a meeting and draft it together, or would you like to push the deadline back and give yourself more time to finish it. Which one would be easier for you?

When your leader does what you see above. Don’t just shrug your shoulders and walk back in your office. Give them options. Invite them to stay accountable for things that were so darn important yesterday and need their attention. Leaders get enamored with the newest and the shiniest. Yesterday’s new and shiny may still be important, but leaders may need some gentle prodding to remember that. Do that through OPTIONS and QUESTIONS not COMPLAINTS.