People Aren’t Stepping Up? Ask Madeleine

Dear Madeleine,

I lead a team of seasoned, expert professionals in a fast-growing global company. My boss has told me in no uncertain terms that my biggest priority in the next year is to develop my team and groom a successor.

My biggest obstacle is, although every one of my team members is very good at their job, not a single one of them seems to have any idea how to rise above their day-to-day and see the bigger picture. I’ll give you an example of how this shows up.

I recently gave one of my people—I’ll call her Sharna—the opportunity to present to our executive team, which my boss is part of. It didn’t go well. I laid out the requirements for the presentation, which was two weeks away. I gave her clear direction on what the ET would want to hear about and what and how to think about it going in. I offered as much support as I thought she would need.

The meeting was scheduled for a Monday afternoon. She sent me her initial draft the prior Friday afternoon. I gave her feedback over the weekend and she sent me her final deck a couple of hours before go time.

I knew it wasn’t going to meet the ET’s expectations, but it was so close to the meeting that I thought it would do more harm than good (in terms of her confidence) to get her to make changes at that point. I did provide a few comments and she made some last-minute edits, but there were still typos and some repetition. It wasn’t up to standard at all.

My boss was not happy—and he, quite rightly, blamed me. But Sharna is a seasoned professional and an expert in her field. She had delivered much higher quality work in the past, and I had no reason to think I couldn’t trust her. Did I really need to express to her more clearly how important the presentation was? I thought it was glaringly obvious.

This is just one example. I guess I am expecting all of my people to be able to understand things that I see as self-evident. How do I to get them to think more strategically? I have to somehow get them out of the weeds—but I don’t want to turn them into versions of myself.

My People Are in the Weeds


Dear My People Are in the Weeds,

Oh dear, this is a can of worms. Essentially, the leadership competency you need to build is Developing Others. As Stan Slap has said (I am paraphrasing; he is so witty), most leaders would prefer to go where they need to go by themselves and then send a postcard to their people saying “wish you were here”—because it’s so much work and so time consuming to get people to see your vision and help them walk the path you need them to walk! The problem is you simply can’t do it all yourself, which is what your boss is trying to get you to see. You must shift from doing everything yourself to getting things done with and through others.

If your people could see what you see, they would have your job. It sounds like you might suffer from a condition I, too, have, which is that if something is obvious to me, I assume it is obvious to everyone else. Big mistake.

So you and your people all need to develop some new skills. On top of the 24/7 scrum of day-to-day work, it feels like a lot. Because it is.

For you, this will mean getting crystal clear about your expectations. And don’t stop repeating them until you see evidence that each person not only understands them but also has a plan to figure out how to meet them.

This will require patience and diligence on your part. Expect it to be tedious. You are addressing people who have been successful their entire careers because of their subject matter expertise and their ability to get things done. You are asking them to think differently and step out of their comfort zone, which takes practice. And it is scary for people when they are asked to try new things they know they aren’t good at.

To help them think bigger picture, your people need to understand what the executive leadership team is thinking about, their immediate concerns, the problems they are trying to solve, and the threats they see coming at the organization that are keeping them up at night. If your CEO is not sharing all of that intel regularly, it really is your job to relay anything you know to your team. The more you do that on a regular basis, the more your people will develop the habit of paying attention to how their job connects to the bigger picture. You just cannot expect them to tear their eyeballs away from their day-to-day tasks and look to the horizon unless you are directing their gaze there.

Regarding the presentation, I agree that the lack of thoughtfulness and preparation was clearly not where it needed to be. We all know that there is simply no substitute for preparation and time to iterate and practice. You might just get curious and check in with Sharna with some questions. Something along the lines of: “What happened? I expected more preparation and for you to allow time for iteration and you came in hot. Is there something going on I should know about?”

Is it possible she has an issue with presentation skills? Subject matter expertise is critical, of course, but taking into consideration who is in the audience, what they need to take away from the presentation, and how they prefer to consume information is a whole skill in itself. You might turn her on to the work of Nancy Duarte, who helps people master the art of using data to tell a story and shape information so that it connects to their chosen audience. She has multiple excellent books and workshops.

I hear your concern about not wanting to micromanage people so they simply parrot what you want them to say. I have heard this from many leaders. But here’s the thing: If people knew how to do what you want them to do, they would be doing it. So be specific about what you want, teach them if you have to, and stay alongside them until they can fly solo. They are still going to be themselves and bring their own strengths to the party as they get more comfortable with the task. Don’t worry about turning people into mini-me’s – it won’t happen, I promise.

You are obviously a pro, a high achiever, and a hard worker. You can do this if you think it is important enough.

Love, Madeleine

About Madeleine

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 soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

2 thoughts on “People Aren’t Stepping Up? Ask Madeleine

  1. Madeleine,
    Great advice as always.

    I’m not sure all CEO intel is to be shared with everyone. I believe this does require a filter of sorts.


    • You are so right. Some CEO’s are more transparent than others, and I do find that many executive leaders forget to share much needed context they get from the top. But a filter is always needed!
      Thanks for the kind words.

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