The ask behind the ask

Give people what they want instead of what they ask for

A few weeks ago, I sat in a team meeting where one of my direct reports went through their “day in the life.” This is one way we’ve stayed together during the pandemic, and I comfortably listened to a familiar schedule until hearing my own name snapped me to attention.

“One of the things Benyamin taught me is that what people ask for isn’t really what they want. People ask for specific work instead of general results, and if you can understand what they’re trying to accomplish you might be able to help each other without adding more work.”

So nice! I was gratified to hear that someone listens to me talk, and especially that they listened to this point — which is so very common and so very important. 

How many times do you get requests from another team and think “huh?”

In a big team, other people start asking you for help. Which means you work to maintain a delicate balance. If all you do is what other people ask for, you’ll never get your own stuff done — but if you say no to everything, you’ll become isolated, not able to get what you want, and won’t be helping anyone. 

Plus it's just not very sporting.

The way around this problem is to listen to what people actually ask for, because it’s almost never the same as what they ask you for. 

The other day someone asked me “hey is your team still using WordPress for the blog?” We are, and it would be a huge undertaking to switch CMSs, so the question confused me. 

When I investigated, the situation was “I get a forbidden message when I go to the login page,” a simple fix involving our VPN. 

This was a minor situation resolved in 2 minutes on slack. But look at how much distance there is between the ask and intention.

• The intention: I would like to publish something on the blog.

• The ask: Hey do you still use WordPress.

By the time a person comes to you with an idea, they’ve already reached a conclusion about what they need — whether or not their conclusion is the right one. The idea comes to you as “hey I need [thing]” or “do you use WordPress,” instead of “this is the situation I’m dealing with and I could use your help.”

What’s an eager-to-help-but-has-other-stuff-to-get-done person to do in this situation?

I think there are two parts:

1. Make sure anything you ask for comes with context

2. When you get a question, work to understand the ask behind the ask

When people ask for stuff, what are they really asking for?

What’s the ask behind the ask?

Instead of “do you still use WordPress,” it’s “I am trying to publish a blog post.”

Yesterday I got a note asking if we had any information about the impact of customer stories on conversion rate. We don’t have that number exactly, but it piqued my interest. Why did the person want to know?

The person was trying to decide between using a customer story or some other point of persuasion — and with context it turned out we didn’t need the data at all. Just including a testimonial alongside the other argument got us the best of both worlds. 

But again, the question I got was very different from the intention:

• The question: Do we have any data about how customer stories affect conversion?

• The intention: I need to decide whether to use a customer story or something else.

• The deeper intention: I am trying to convince someone to become a customer and need to know what to do.

When I dug in, it turned out the question I was asked didn’t need answering at all — there was a way to address the deeper intention.

If you don’t understand the ask behind the ask, you wind up in a lot of frustrating situations. You become reactive. You spend a lot of your day answering questions or digging into research or doing work that is relevant to other people’s goals instead of yours.

Worse, you miss out on opportunities. People come to you with a question, but often their question is the wrong one. If you answer it without digging in, it becomes harder to find the “right” path forward, to uncover an approach that better addresses the underlying problem.

Why does the ask behind the ask happen? 

Because people have worked out the approach they want to take before they come to you. They’ve gone through the steps in their head, concluded (rightly or wrongly) what they need, and decided that you are the one who can give it to them. 

Of course, often people jump to a conclusion that isn’t good for anyone (the number of times I’ve been asked “can we get a blog post for this…”). The reason they come to you is for your expertise, and the logical extension is that the question they’ve formulated was created without your expertise.

It is part of your job to call attention to wrong questions. Your job, almost definitely, is not to sit in a room and answer exactly what people ask for — it’s to employ your skills in service of a larger goal.

How do you uncover the ask behind the ask?

What do you need to do to figure out what people are really asking for?

I try to ask “what” and “how” questions, instead of “why” questions. I use the phrase “I’m curious to know more about…” I answer specific questions by not answering the question and first giving more general context, to see if that prompts people to share more information. And, finally, I make educated guesses about the intent behind a question, once I’ve come to know a person reasonably well.

This is difficult to write about, because there’s no instruction manual. There are times when asking “what’s the goal here” is going to feel needlessly confrontational — if a stakeholder is under time pressure and the request is reasonable, they are unlikely to want to zoom out. But there are also times when saying “before I answer, I’d be curious to step back and get a sense of the bigger picture” is crucial (and I like that phrasing more than “what’s the goal.”)

The most important factor is vigilance (CONSTANT VIGILANCE! Remember that guy?). To probe for more information, you have to remember that more information exists. It’s easy to fall into a pattern of answering questions as they come in — even when you and the person you’re talking to would both be better served by a pause.

When people ask “what skills make people successful at this company” (which they often do during interviews), I answer “the successful people find a way to say yes.”

The question you get is often the wrong question, and if you don’t dig deeper you’ll have to say no. The ask behind the ask makes it easier to find a path forward that benefits everyone.