Managing a Boss Who Doesn’t Know What They Want

I received an email from a coach last week asking for advice on how to get better feedback. She has a client who is trying desperately but failing to meet her boss’ expectations. The coach described the scenario as the boss saying, “Bring me a rock,” and when the employee brings the rock, he says, “Not that rock!.” It’s infuriating (not to mention demoralizing and hugely inefficient) when you work for a boss who doesn’t know what they want.

You’re unlikely to fully fix your boss’ muddled mind, perforated plans, or revolving requests, but you should be able to reduce their negative impact on you. Try these steps.

Get As Clear As Possible from the Start

In my book The Good Fight, I tell a silly story illustrating how unclear expectations lead to unhappy outcomes. The short version is that your boss asks your team to bake for a company bake sale. He provides no specifics; neither you nor your colleagues ask for clarification. Flash forward to the morning of the bake sale. You bring your famous carrot zucchini muffins. You’re proud as punch bringing your scrumptious golden-domed muffins to the sale, but the boss scolds you for bringing muffins to a bake sale. “Kids don’t like carrot muffins!” While he’s chastising you, he starts trying to pull out the obvious bits of carrot and shoves some M&Ms in for color. “Kids, what kids?” you think to yourself.

Dumb story, real problem. Here’s how to get off to a better start.

Clarify What They’re Looking For

The first round involves simply asking questions to get your boss to describe better what they’re looking for. In the bake sale example, asking “Who is this for?” would have clarified that you were baking for kids, not adults. That alone would have gone a long way.

Another place to probe is if your boss has filled their request with adjectives. Work through them one by one, asking for examples. “You said you’d like this to be “innovative.” What would innovative look like in your mind?”

Understanding why the work is important can also be useful. I’d avoid asking “why” directly because it can seem challenging to a superior, especially one who’s a little cloudy on the answers. Instead, ask, “Where does this fit with the work Marc is doing?” or “You’ve specifically asked for this to be a written document; what do you see as the benefit of that approach?”

Seek Principles and Parameters

Where possible, and especially if your boss struggles to answer the what and why questions definitively, switch to questions that help you understand the principles and parameters they will use to evaluate your work.

Of course, if your boss is struggling to define what they want, they probably aren’t going to be able to lay out a crisp set of principles and parameters, so you’re going to have to help them out with questions such as “Where there are choices to be made, should we err on the side of inclusiveness or speed?” or “What would be the minimum number of customers I should factor into the analysis?”

Define Bad, Good, and Too Good

Another risk with an unclear boss is that you go off trying to build perfection and invest way more time than necessary in your output. While I’m sure it’s apparent that you should leave a conversation with your manager understanding the difference between bad and good, it’s just as vital that you know the line between good and too good. Try questions such as, “What would be out of scope at this point?” or “How many hours do you think I should invest? Should I limit how much time I spend?”

Seek Clarity from Others

If you’re getting nothing but blank stares or mumbo-jumbo from your manager, there might be alternative sources of clarity. Are there other members of your team who have a better sense of what’s needed? Can you ask to participate in any customer or cross-functional discussions that set up the work? Is there a project manager involved who might have a better shot at facilitating alignment? Don’t assume your boss is the only source you can go to to get a better handle on what’s required.

Bring Work in Progress

If we return to the bake sale analogy, multiple opportunities exist for direction and course correction, if necessary.

Summarize Your Understanding

When your boss finishes their delegation, summarize what you heard and what you’re taking away as your marching orders. Ideally, do this in writing. That might mean on a whiteboard in a meeting room, in a Slack channel, or through a follow-up email. Ensuring that you are at least on the same page at the start can save you from getting way off course from the get-go.

Bring a Plan

Next, share your high-level plan for tackling the assignment. In our bake sale example, that would have meant saying, “I’m thinking carrot-zucchini muffins.” Doing so would have avoided wasting time, resources, and frustration. Because of the bake sale story, I think of this as always sharing your recipe before buying ingredients.

“Always share your recipe before buying ingredients.”

Show Your Work

If you’ve clarified the goal and shared your plan, it would be nice to think that you could go away and deliver with little risk of getting off track, but if your boss is a little slippery, you might want to add one more step. Share your work in progress and get feedback before you take it too far. I call this “tasting the batter” because it’s much easier to add M&Ms before you bake than after.

“It’s easier to fix batter than baked good.”

Highlight the Cost of Unclear Expectations

If your boss is a repeat offender in the unclear expectations department, it’s usually worth highlighting the cost of that poor delegation in hopes that it will lead to more care and effort up front next time. Of course, you want to be careful and diplomatic, but if you think you can safely say something, take the opportunity.

Lay Out the Windy Path

When you present your work, document the initial scope and all the iterations and course corrections you went through. Use the exact language you used to confirm the expectations so you’re not showing anything your boss hasn’t seen before. This will highlight the twisty path you took and set you up for giving feedback or searching for more efficient processes later.

Track the Investment

Where it makes sense, keep tabs on how much time you spend and what proportion of this time is wasted because of changes in direction. Some managers don’t have a clue how much of a wake they leave behind them. Share this information after you’ve completed the project to your boss’ satisfaction. It’s a better fit as part of a “lessons learned” than as complaining along the way.

Give Feedback

If your relationship is strong enough, provide clear and direct feedback about how the lack of clear instructions affected you. For example, “When the specs changed after week one, I had done two days of work that didn’t end up being used. How could I get a better handle on what you’re looking for before I invest that much time?”

You’ll notice that I soft-peddled it by framing the question in terms of what you could do differently rather than what your boss could. That’s a safer approach, but feel free to switch to a request of them, such as “Would it be possible to spend a little more time upfront sharing your expectations next time?” if you feel comfortable doing so.

Conclusion

I’ve baked a lot of muffins when the boss was secretly hoping for cupcakes. It’s disheartening and wildly inefficient. These tips aren’t likely to cure a boss flying by the seat of their pants or furiously flip-flopping, but they should get you a somewhat more precise target. You might need more than one recipe and a few tweaks to the batter, but hopefully, once it’s fully baked, it comes out exactly as they had hoped.

Additional Resources

How to Get People To Live Up to Your Expectations

10 Tips for Being Accountable at Work

From Jason Cortel Help! My Boss Sets Unclear Expectations

 

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