The best question we’re too afraid to ask

Asking “Am I meeting your expectations?” demands bravery of you and the recipient

I got fired as CEO of FirstUp, a company I founded and spent 10 years (and 3 pivots) building.

Over those years, my lead investor (his name is on the door of the fund) became a close friend and still is today. But his operating partner in the fund was a quiet detractor. He was a CFO type, and he didn’t like the “messy middle” of building companies – or at least the messy middle that I created.

In my heart of hearts, I knew he was unhappy with me. But I didn’t want to hear it.

So I didn’t ask the question that could have laid bare his reservations:

“Am I meeting your expectations?”

It’s such a basic question, but so powerful. It encourages the recipient to expose their personal, often subjective expectations. Imagine asking it of your boss, your client, your best friend, your spouse – it would likely create a conversation you’ve never had before.

So today, let’s dig into how (and when) to ask it.

– Greg

When to ask “am I meeting your expectations?”

All relationships come with expectations – said or unsaid. Most people aren’t good at articulating them, and they won’t tell you their expectations (or even think to) without prompting.

There are two good moments to ask this question:

• Proactively: You’ve gotten to know each other, but you’re not so far into the relationship that missed expectations have built up and become unfixable. Look for a natural milestone – a signed deal, a completed project, the end of the quarter.

• Reactively: You’re getting a signal – even a weak one – that something is off. Your boss pushes your 1x1 too many times, the prospect keeps putting off a signature, or a friend can’t find time for lunch.

At these moments, you probably avoid asking the question because you’re worried about the answer. It’s human nature. But it’s almost always better to ask the questions you don’t want the answer to – and “am I meeting your expectations?” is one of those questions.

I see this with salespeople a lot. They invest their time with prospects that don’t say no – but also never say yes.

That’s when you ask: “Can we meet your expectations – and if not, are we ever going to be able to?”

It might be just what they need for a moment of honesty. They could say, “You know what – I want it to work, but I don’t think so.” And everyone could save hours of back-and-forth.

Why it’s different from “what could I be doing better?”

You might think, “Okay, but I do this every year in my performance review or even in my 1:1.” But I’m guessing you word the question slightly differently:

• What could I be doing better?

• Do you have any feedback for me?

• What should I work on this year?

These questions inherently assume that your boss/client/CEO has a short list of suggestions to improve your performance. They don’t leave room for the possibility that you’re doing the “right things” but still not meeting their unique, specific expectations.

Asking “am I meeting your expectations?” prompts the listener to mentally compare their actual experience with their desired experience – and show you the gaps.

A few weeks ago, Taylor’s chief of staff said to her, “Earlier in the year I was doing some things that I thought were important parts of the chief of staff role, but I didn’t realize that you didn’t care about those specific things.”

She’s right – Taylor’s expectations for chief of staff are different from others’. Her chief of staff was great about asking for feedback, but without asking “am I meeting your expectations?” point blank, Taylor wasn’t forced to reflect on and be more articulate about her personal, subjective expectations.

How to ask to get an honest response

It’s possible that you’ll ask this and still get a milquetoast response, like, “Yes! You’re doing great” or “Yes, though I might work on this one tiny thing…”

So we recommend asking in a way that incentivizes an honest response. Put differently – let the bravery of the question demand a brave answer.

You can make clear you’re expecting a thoughtful and honest answer by adding some additional context. Here are some examples:

• “Am I meeting your expectations? I really want to know, so could you take some time to think about it before we meet next week?”

• “Am I meeting your expectations? I want to make sure I understand your specific expectations for this role (not just the general expectations of a [x role]) and how I’m stacking up.”

• “Beyond the results we’re getting, are you comfortable with my approach and process?”

Our advice

For the last year, our board at Section has been signaling their approval – we’ve made a smart pivot, managed cash tightly, the business is growing, and we’ve hit the last eight quarters. If I ask, “How am I doing?” (or even if I don’t) they say, “Great.”

But if I asked one of our board members, “Am I meeting your expectations as a CEO?” I honestly have no idea how they would respond. So it’s time for me to ask the question.

“Am I meeting your expectations?” is a scary question. You’re stepping onto thinner ice – putting the relationship (and your own ego) potentially at risk. But more likely, the relationship will come out stronger.

My best advice is to learn to ask the question earlier in your life. Encourage the people in your life to make obvious what isn’t obvious to you – their idiosyncratic expectations. Ask it before those expectations have gone unmet for months or years.

Be brave, ask the question, and be willing to engage with the answer.

Have a great week,

Greg & Taylor