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How to Work with a Leader Who’s Consistently Unclear

No matter how high up you are in your organization, it’s frustrating when your boss thinks they’re being perfectly clear about plans, goals, and premises, but you know there are details they’re unaware of, concerns they don’t understand, or important considerations they don’t care about.

I’ve worked with many strong operations execs who have been perceived to be negative for identifying and pointing out all the likely shortcomings in an otherwise exciting idea. Certain leaders simply don’t want to hear about hidden flaws or potential downsides. They’re so excited by the possibilities, or invested in achieving a particular input or outcome, that they feel their job is done once they’ve announced their plan.

Whether you’re a subordinate or a supplier, from time to time, you may be convinced that something in your leader’s grand idea won’t pan out the way they think it will. When that happens, what can you do? You don’t want to come across as negative, but you don’t want things to come to a bad end either. Try approaching your leader in three stages.

Hear them out completely.

If you interrupt their flow to explain things that won’t work or might go wrong, they’ll feel forced to justify why their plan is perfectly fine the way it is. They may see you as a nitpicker, fearful, or in league against them. Don’t give them the ammunition.

Instead, be extraordinarily attentive. Take detailed notes of their aims, intentions, and preferences as well as your own concerns. You’ll need lots of patience for this, and you may have to work hard to hold your tongue.

Give their own content back to them.

You can do this either at the end of the same meeting or after you’ve gone away and reviewed your notes. Remember to bridge: “Boss, I think I’ve got it, but I’m going to go through my notes and come back to you tomorrow to review everything.” Then, depending on the way they like to work, you can respond in person or via email.

Stick as closely to their own words as you can, smoothing them out to sound as clear and even as motivating as possible, and check to verify your comprehension. Focus on the leader’s desired outcomes and impacts, not on the actual implementation details. This recitation should reassure them that you’ve got it, you’re on board, and you appreciate where they’re trying to go.

I’m not asking you to agree with them: “Oh, that’s a wonderful plan.” Rather, simply acknowledge them: “I think this is what I heard you specify as the most important aspects, right? And you’d like to see such and such happen?”

Ask explicitly for their understanding, leeway, and support.

Make it clear that you’re going to figure out the best implementation, or that you’ll be presenting the problem to your team so they can get to work on it. Explain that, for things to go smoothly, it would be helpful for them to clarify X, let you do Y, or show patience as you’re figuring your way around Z. You can even tell them that you’ll be coming back with other requests like that.

In most cases, concept “champions” don’t mind helping you out if you’re stuck, so long as they believe you’re on the same page and trying to give them what they want. They’ll be happy to provide you advice, and maybe even protective cover. They just need to know you’re committed to the success of their ideas.

Onward and upward —


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