Can’t Delegate? Ask Madeleine

Dear Madeleine,

I am the new CEO of an asset management firm. I am concerned that my executive team is not up to speed and I am nervous about delegating to them.

They are all super talented, bright and experienced. The problem is the former CEO was a micromanager who was punitive when people asked for help. Now I need to change the culture in the group to make sure people ask me for help before they dig themselves in too deep.

I have told them to feel free to come to me if they have doubts, but they don’t—and then there is a mess to clean up.

This is a critical juncture. The eyes of every board member are on us. But I am traveling too much and doing work my team should be doing because I don’t trust them not to screw things up.

I know I have to stop this, but I don’t know how. Ideas?

Can’t Delegate

Dear Can’t Delegate,

It is true that most new leaders would prefer to shoot off like a rocket to where they are going and send a postcard from the destination. Welcome to the brave new world of getting things done through others. This is the transformational journey that you unwittingly signed up for, and it will be fraught, difficult, and intensely rewarding. It will require patience and generosity and—probably most challenging for you—slowing down right now so you can go faster later. Here are a few ideas:

  • Shift your mindset. It’s hard being a genius (I use Immanuel Kant’s definition of genius as someone who creates new things with existing materials or ideas.) I know this because for 25 years I have specialized in coaching them—and I have been married to two. I’m guessing you have an exceptional ability to make connections between big abstract ideas that are obvious to you. Because they are obvious to you, you assume they are obvious to everyone else—but this is where you are wrong. You have to slow yourself down enough to articulate the steps and connections between your big ideas. You have to draw pictures, show the progression of logic, and connect the dots between your big cognitive leaps. Tedious? Yes. But a critical part of your job right now.
  • Address the problem head on. Pull your team together and articulate the problem as you see it. Talk about the former CEO and his method of operating, making clear that your approach is not the same as his. Be explicit about how you will reward people when they ask for help. Scott Blanchard, who works on many complex deals, has a mantra he repeats: “Don’t lose a million dollar deal by yourself.”
  • Remember that you are suggesting a big change. Asking for help makes some people feel vulnerable and can require fairly intense personal development. Challenge each of your people first to figure out what gets in the way of their asking for help—and then to push themselves past it. Introduce them to Brene Brown, who is at the forefront of the research showing that learning to be vulnerable makes better leaders.
  • Apply a method to assess competence and confidence. In our flagship model, Situational Leadership® II, we teach leaders how to work with people to zero in on exactly where they need help to become the wiz they are. Remember that the tasks you are delegating are highly complex. How come you don’t screw up? Are you that much smarter? No, but you learned a lesson along the way—figure out how to help people identify their development level on a task.
  • Allow the team to reason through complex situations even if you already have the answer. Let them work it out together, learn from each other, and grow as a team. If you absolutely must, you can throw in your wisdom at the end.
  • Share your thinking. Anytime you learn something new, send the learning to everyone on your team. A short email is all it takes. When you travel, take someone with you and share your every thought on what you are learning and experiencing along the way. You think they can read your mind,—or you wish they could—but they can’t and they won’t. So tell them everything you think they need to know.

You were made CEO because it was assumed that you will be able to do what you do and empower your executive team to be brilliant. If you apply only two of these ideas, you will be well underway.

Love, Madeleine

About the author


Madeleine Homan-Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response here next week!

5 thoughts on “Can’t Delegate? Ask Madeleine

  1. Giving the team challenging goals with attractive rewards helps in succeeding at delgation. We also need a good measurement system with metrics in place. Nice article. Learnt something today. Cheers Ramkumar

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