“Know when you’ve closed” and other notes on handling challenges

Published on 29/04/2025

I recently attended a meeting, it’s a regular meeting where I work, where new technology implementations get discussed and approved. The point of this meeting is for your ideas to be challenged. Picked apart. Poked and prodded. And it’s never personal!

But even knowing that, and having done many of these meetings now, it doesn’t make it any easier. Facing this interrogation and having to justify yourself is daunting! But there are certain things you can do, approaches you can take to make it a little bit easier.

One of the directors on the call said something which stuck out to me, which was “Know when you’ve closed”. I will come back to that a little lower down this post, as I think it’s both super important and super difficult. Great combination!

Before that though, what are some easy ways you can make approaching these interrogations easier? If you have something similar coming up, what can you do to make your nerves a little less nervy?

First off, remember it’s not personal. In this particular meeting that is definitely the case, and you might think that this point doesn’t apply more generally. But I am here to disagree! Well, I’m here to write about the more human aspects of software development, but right now! Right now, I’m here to disagree. By and large, people don’t turn up to work to be difficult. Or rude. Or mean. Everyone is there to achieve the same thing, and while you may disagree on what the best course of action is, you want the same outcome. So, when someone challenges your ideas - try not to take it personally. Don’t get defensive.

Now that your hackles are back down, and you’re not immediately going into defence and fight mode, let’s look to point two. Listen to understand, not to respond.

Let me say that again. Listen to understand, not to respond.

A little confusing at first, no? We need to respond, so surely we… No. Let me explain. Listening to respond is simply waiting for them to finish. Listening to respond is already thinking of your counter arguments as they’re talking.

Listening to understand, on the other hand, is trying to understand the deeper meaning of what they’re saying. Thinking about why they’re saying it. Trying to pick up on context clues. On the bigger picture. Listening to understand is about paying attention to why someone is saying something, not just what they’re saying.

At some point I’ll do a full write up on this, as I think it’s super crucial! For now, let’s move on.

Sometimes you don’t understand, even after trying to listen in that mindset, and that’s ok! I struggled here to know where to put “know your shit” as a tip for feeling more confident dealing with challenge - and I think I’ve settled on after “it’s ok if your don’t know you shit”.

Sometimes you need to ask clarifying questions. Sometimes you need to do a bit of digging to understand what they’re truly asking you. Don’t be afraid of this. It shows that you’re truly trying to understand before you answer, which builds trust (and therefore confidence) in your answer. If people see you’re spending time making sure you’re answering the right question and not just jumping in on auto-pilot, then they’re likely to feel respected. Valued. Heard. And they will be more engaged and bought-in on your response!

Which ties nicely into owning anything you don’t know. Again, a full article could be written on this, but for now let me just say this - when you tell someone you don’t know something, they’re more likely to trust the things you’re saying you do know. Because it shows honesty, self awareness, and integrity. There’s just one caveat! Always follow it up with, “but I’ll find out”. And then go and find out and get back to them. Ok, so maybe two caveats.

So, while you need to be comfortable with not knowing shit. Equally? Know. Your. Shit.

Sounds simple, but the easiest way to feel more comfortable being questioned on something is to know it inside out. Prep for the questions they don’t ask. Have the documentation they didn’t ask for. Have the data & dashboards they don’t look at. It’s better to have it, and not use it than not have it, and need it.

So, finally, the titular comment “Know when you’ve closed”

Why did this resonate with me? What does this mean? Well, in a word? Shut-up.

Just as you should be listening to understand, you need to be paying attention as you talk. Just as you identify the question someone is truly asking, and the best way to answer it, so to do you need to pay attention to whether what you’ve said/are saying is doing an adequate job.

Knowing how to pivot mid answer is skill, knowing that what you’re saying hasn’t landed and you need a new tack. A new angle. But equally, knowing when you’ve said enough. Look for when they smile. Look for when they nod in agreement and make a little note in their notepad. That’s usually a signal that you’ve done enough. You’ve convinced them. Stop there, move on, next point.

With practice, you’ll get better at understanding what people are really asking, identifying the best response to answer that question, and giving no more or less than is needed to do just that.

Answer their question.

Because really? That’s what this all boils down to.

Remember it’s not personal.

Don’t get defensive.

Listen to understand, not to respond.

Clarify if needed.

And then?

Answer their damn question.

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Created by Keeghan McGarry