Ambiguity Making You Crazy? Ask Madeleine

January 7, 2023 Madeleine Homan Blanchard


Dear Madeleine,

I have risen through the ranks of my organization very quickly. Last year I took on a lot of new responsibilities with almost no direction, did a good job, and got a raise and a promotion. My boss, the president of the company, has told me several times that he sees me as partner material.

One of my superpowers is figuring things out—but I fear I have reached my limit in one area.

I keep asking my boss for more clarity on what is expected of me to be able to reach partner. And he keeps saying I need to become “more comfortable with ambiguity.” It is maddening. If I knew what I was supposed to be doing, I would be doing it. But he won’t tell me.

Any ideas for me on how to break through this impasse?

Flying Blind


Flying Blind,

You have just described the exact conundrum of making the leap from operational leadership to strategic leadership. When you reach the top ranks of any organization, the biggest shift is that there is no longer anyone to tell you what to do. What your boss is trying to express is that at the level you are playing, it is up to you to use your best judgment and make it up.

What most people don’t realize (until they are doing it) is that executive leadership is a wildly creative—and risky—business. When people are young, a little naïve, and lacking in experience, it can be incredibly exciting. When people have suffered the pain of making expensive mistakes, it can be terrifying.

Here is an article published recently: “The Ultimate Test: What I learned about leadership from Covid-19” that lays out exactly what I mean.

Managing ambiguity literally means figuring out how to get things done when things are not clear, nothing is certain, and there is no road map. It means looking at the whole picture and envisioning the path from where things are now to where you and the other senior leaders say you want to be.

Almost nothing you have been good at or thought you knew up till now is going to help you much, but it can be a good foundation. You will be required to let go of your addiction to checking tasks off your list and get comfortable with moving from incomplete task to incomplete task. For people who define themselves by their ability to get things done, this is a mind-bending transition. Get used to spending your time sharing your vision for the direction your people need to go and experimenting with approaches. Be prepared to adapt as new information comes in, and to pivot if necessary.

The metaphor that has been helpful to many is instead of checkers, you are now playing chess. Instead of moving all your pieces across the board quickly in a day or a week, you will now be lucky to make one or two moves in that time. Each move will require a lot of thought and consideration, frequent checking with others on the team, and possibly accepting a temporary fix until new information is revealed. It is dealing with constant change—and the job is never done.

One thing you can’t do on your own is decide on strategic imperatives. If your boss cannot articulate those, you can push for the leadership team to make decisions on what they are. Once you have those, and a sense of a budget, you will have to make up the rest.

Hopefully, you have organizational values to guide your decisions. If you don’t, you will have to decide on your own leadership values. That means you must know what is most important. That is a whole can of worms in itself and you can find more on that here. If your organization has not spent the time to articulate its values, you can advocate for putting some attention on that. Get some arguments for doing that here.

To be a partner means to be a co-owner with the other partners. Your boss is waiting for you to be brave. So be brave.

Make a plan for what you think needs to be done for you and your people to achieve, or even exceed, the strategic goals that have been set. Do you have the right people in the right seats? (Do they have the skills to do the job the way it needs to be done?) If not, how will you address that issue? Do you have all the resources you need? What hasn’t been thought about yet? What obstacles need to be cleared?

Let me be clear here: this is not a plan for how you will make partner. It is a plan for how you will lead your people to accomplish what needs to be done for the organization. It isn’t about you, it is about the success of your team and the organization.

Lay out the path for how you will do everything. Make a list of the unknowns and the obstacles you can see today. You will be worried that you’ve made mistakes, that you’ve missed something, and that it won’t be perfect—which will almost certainly be the case. That’s OK. No one and nothing is perfect right out of the gate.

Take your plan to your boss as your best guess of what you think you should be doing in the next 12 to 18 months and see what he says. Talk it through, get feedback, and share it with other leaders in the organization. If you think you are right about something that others disagree with, have the courage of your convictions and make your case. Or, if you think someone else’s point of view makes sense, let yourself be influenced. Then tweak the plan, share it with your team, and go.

You have passed the point of studying for the quiz and getting 100% and a gold star. You are now in unknown territory where you have to make your own map, and the test is about making decisions in the absence of enough information. Not only are there no gold stars on offer now, you will be surrounded by people who think they could do it better if they were in your shoes.

You say you have reached your limit for figuring things out? I say you are just getting started. Get comfortable with being uncomfortable. You are signing up for a bumpy but exciting ride!

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.


About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

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