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How to Say No Without Feeling Guilty

My mediocre superpower would be having the ability to say no without feeling guilty.

Naval Ravikant

How to say ‘No’ without feeling guilty? Here in Australia, we tend to cheat. First, we lull you into a false sense of affirmation before casually segueing into rejecting whatever you want us to agree with or do. Yeah, nah… is essential Aussie slang that reflects the universal dichotomy between yea and nay.

On the one hand, we want to be polite and not give offence. On the other hand, acting like a pushover who’s being taken advantage of isn’t a soul-nourishing strategy either. Do we have to choose between two evils? Yeah, nah… But how can we say no without feeling guilty – or cheating? Before jumping into three ways to nope out of a situation, let’s start by reviewing our relationship with the word itself.

The Power of Saying ‘No’

Yes, ‘Yes’ tends to be seen as positive, polite, affirming, collaborative and constructive. In contrast, ‘No’ has a bit of an image problem. It’s associated with negativity, failure, mistakes, or even hostility. This can make it hard to use it, even when it’s justified. There are good reasons to embrace it, though.

Arguably one of the best cases for the power of ‘No’ has been made by former FBI hostage negotiator and professional nay-sayer Chris Voss. I’ve reviewed his book Never Split The Difference here. Chris disagrees for a living but in a way that doesn’t upset his counterparts or himself. He challenges our perceptions with a counterintuitive look at ‘No’:

  1. At its core, saying ‘No’ isn’t an act of unkindness or hostility. It’s self-protection. When we say the word, we safeguard and reconfirm our autonomy and independence. I would add that deep down we probably know: If we can’t say ‘No’, we’re at the mercy of everything people want us to say or do. But if we can say ‘No’, it doesn’t have to be the end of a conversation either.
  2. In fact, Chris frames the ‘No’ as the beginning of an interaction. He even goes as far as suggesting to start negotiations by eliciting the dreaded word. It gives people a sense of safety and control over their decisions, which then allows the conversation to be more collaborative and productive. With what your counterpart doesn’t want out of the way, you can focus on what they do want.

So whether we hear it or have to say it ourselves, we can look at this seemingly guilt-ridden word as an act of self-care and the starting point of collaboration.

How to Say No

That only gets us halfway of course. And still leaves us with the question of how actually to say it. ‘No’ is a rather blunt instrument of disagreement. We need a more sophisticated way to safeguard our autonomy and interests without compromising our relationships. The real question is how you can convey such a categorical message effectively yet politely. Let’s dive into three different ways to say ‘No’ without feeling guilty.

1. The Constructive ‘No’

I did what you asked. Unfortunately it didn’t quite work out. How about we do this instead?

Our first way to say ‘No’ is the constructive ‘No’. It’s inspired by ex US Navy SEAL and notorious early bird Jocko Willink. Occasionally, he relates the story of a soldier being ordered to lead his men clear a machine gun nest in a frontal attack. It’s a suicide mission. Disobeying the order could cost him his job while compliance could cost him his life, including those of his men. Plus, if he doesn’t do it, some other poor soldier will take his place and probably die in the attack. There’s clearly a lot of guilt associated with either decision.

To solve the conundrum, Jocko suggests an indirect approach. Act out the order first. Just a little bit, though. Carry out your “attack” just enough to collect intel on the resistance you meet and develop an alternative plan based on that. Armed with the valuable feedback you then go back and make a suggestion: “Look boss, we did what you asked, but we were met with heavy resistance. How about we flank the enemy instead?” You may appreciate the irony that in suggesting to flank the enemy, Jocko also flanks the leader’s orders.


The principle of the constructive ‘No’ is simple. Instead of threatening your counterpart’s authority and sense of autonomy by trying to talk them out of their idea, you go with it and test it out carefully. Observe what happens, report it back and then suggest an alternative that you think has more chances of success. We could say the ‘No’ is shown as opposed to being told. In a best-case scenario, the person whose ideas you’re rejecting realises the futility of their suggestion on his or her own.

In fact, Jocko’s solution is two different types of ‘No’ in one. The first is designed to illustrate the consequences of acting out an idea. It’s not always necessary, but it’s worth going through on the off chance that the stupid idea turns out to be a pretty clever one. The second part is basic pedagogy 101.

As opposed to telling someone what not to do, potentially leaving them with no alternative action, you tell them what to do instead. The unwanted behaviour is replaced with something more desirable. You’re offering an exit strategy. To the very least you’re opening up a negotiation about the best way forward.

What I like about Jocko’s approach is the added compliance in-between. If done genuinely, it shows your goodwill and enables your counterpart to save face. Perhaps the reason for a bad idea was that the leader didn’t know any better. By offering a constructive ‘No’, you avoid creating a decision-making vacuum.

When to Use It

It seems to me that the constructive ‘No’ is best used whenever you’re:

  • in a dependent relationship, that is when your compliance is of importance
  • working in a team and it’s part of your responsibility to (help) solve a problem
  • facing a decision with a price you’re not willing to pay.

2. The Invitational ‘No’

I would invite you to have this feeling be present until it disappears on its own.

This method of how to say ‘No’ politely is a pensive and reflective way to object. I remember doing a tour through the U.K. Parliament a few years ago. It’s an impressive building, full of beauty and one of those places you get a sense of taking a stroll through history. I was surprised that we were even allowed to walk across the floor of the British House of Commons. The tour led us past the so-called Dispatch Boxes, which act as the lecterns where those in power stand to give their speeches.

Elephant in the Room

Unfortunately, I wasn’t allowed to step up and make a short improvised announcement of my own. Nothing kept me from leaping to the podium. Except for our guide who sensed my desire. But instead of telling me off, he was very British about it. He invited me, not for tea, but to cherish the feeling of wanting to impersonate a British politician until it disappeared all by itself. It gave me pause, and that’s the idea behind it.


The principle of the invitational ‘No’ is similar to the constructive ‘Nope’. First, it subtly implies that the action you’re rejecting is something generally understandable and positive, or at least not objectionable in principle. Then you’re offering an alternative, to sit with the desire that cannot be fulfilled. At its core, it’s an invitation for introspection similar to the meditative practice of not labelling or judging thoughts and emotions that bubble up while sitting quietly.

By framing the objection as a polite invitation, you’re also respecting the other person’s sense of autonomy. Admittedly, you only give them the illusion of control. Reading between the lines, the invite is really about what you don’t want them to do. Though, coupled with a genuinely friendly tone and a hint of self-irony, you lower your chances of coming across as a passive-aggressive, sarcastic and judgmental douche.

When to Use It

Obviously, this won’t work when you’re laying in the trenches with Jocko Willink. But you could try it whenever:

  • you’re in a generally friendly, polite and perhaps emotional environment
  • the interaction is in good faith with both sides giving each other the benefit of a doubt
  • the idea or action that’s being rejected tends to be a neutral or positive one.

3. The Questioning ‘No’

How am I supposed to do that?

Our final way of how to say ‘No’ comes courtesy of Chris Voss, our hostage negotiator from the beginning. In one of his many thrilling anecdotes, he tells us about José, a U.S. citizen who is kidnapped in South America. José is held for ransom somewhere in the mountains of Ecuador. The criminals ask the victim’s wife, Julie, for $5 million. It looks like they hold all the leverage. Who would want to say ‘No’ and antagonise the kidnappers in that situation?

Voss’ solution is a real game-changer, though. He’s aware that the kidnappers think of themselves more as businessmen than cold-blooded murderers. He wants to buy time. Chris’ strategy is to have the victim’s partner reply with different versions of what he calls calibrated questions. “How am I supposed to do that?” is his go-to substitute for ‘No’. It can come in many forms: “How can we raise that much money?”, “How can we pay you anything until we know José is okay?”

José manages to escape eventually. The calibrated questions sowed confusion among the criminals. The kidnappers had to repeatedly travel back and forth between the mountains where José was held and the town where they were on the phone with Julie. In working to respond to the calibrated questions, they dropped their guard and José used their disorientation to his advantage.


The principle behind “How am I supposed to do that?” is threefold. It signals your general willingness to comply and collaborate. At the same time, the calibrated question enables you to reject a proposition without openly antagonising your counterpart. Lastly, it triggers a thought process and forces the other side to consider your point of view; something Voss refers to as “forced empathy”.

Broadly speaking, the questioning ‘No’ hinges on Voss’ idea that a ‘Yes’ is worthless without the ‘How’. By asking your counterpart calibrated questions, you stop them in their tracks and make them realise they haven’t thought things through properly. In a best-case scenario, this prompts them to solve problems for you.

We should note, though, that the positive effect of the calibrated question is very much dependent on your tone. It should be calm, warm and questioning with an emphasis on the word do rather than harsh and accusatory. If you nail both, the question and the tone, you’ll keep it collaborative and safeguard the autonomy of both parties until you reach an agreement everyone can live with.

When to Use It

Given its origin, the questioning ‘No’ surely works in pretty much any negotiation scenario. That is whenever:

  • you’re being asked to do something you don’t agree with
  • you’re in a position to have the other side solve your problems for you
  • someone has created a problem they now want to make yours.

Closing Thoughts

How to say no without feeling guilty? I think the guilt associated with saying ‘No’ comes from an understandable yet often misguided feeling of inadequacy. From thinking that we’re doing something wrong, or at least aren’t doing everything we could to solve other people’s problems. But it doesn’t have to be a zero-sum game in which you either let down yourself or someone else.

To overcome the guilt it helps reflect on what exactly you’re objecting to and under what circumstances you’d happily agree. When you do object, you may want to think of saying ‘No’ as an act of preserving autonomy, which marks the beginning of an interaction rather than the end. Sure, your counterpart doesn’t know that. For this reason, all our examples convey the message without actually using the word.

It may not come as a surprise that all ways are built around some form of empathy. The constructive ‘No’ prompts you to have empathy with the people whose ideas you reject. The invitational one encourages introspective empathy. The questioning objection leads your counterpart to have empathy with your own perspective.

In the end, it comes down to knowing when to use which strategy of how to say ‘No’. That’s of course the hard part. But you can manage it and there’s a good chance you get what you want minus the guilt. Would it be absurd to think there’s nothing mediocre about this superpower?