Difficult conversations: how to get what you want

Learning how to have a difficult conversation can increase your personal and professional happiness. Being able to calmly ask for what you want without awkwardness or anger is an important skill. Understanding the components of a successful, difficult conversation, and following the template below will teach you how to get what you want from others.

We use salary negotiation as an example throughout this article. Scroll to the bottom for an example between romantic partners, including what not to say.

We designed these tips for a verbal conversation. But, they work equally well if you want to have this conversation over text. Using email or messenger to lay out your point of view is effective when your recipient is a conversation dominator, scary, or likely to shut you down before you finish speaking. It’s a good way to go if you think you’ll struggle to get everything out before losing courage, crying or getting angry.

girl writing email to get what you want
You can have a difficult conversation over email. It will let you express everything you want to say without interruption.
  • Do you find it hard to express yourself without your heart pounding and a sense of adrenaline where you feel like it’s all-or-nothing?
  • Have you entered conversations planning to ask for one thing and leave wondering how you didn’t get around to asking for what you wanted?
  • Do you struggle understanding how to get what you want from others?

How to get what you want: The key to a successful difficult conversation is planning before the conversation happens.

Figure out your desired outcome

Before you launch into a difficult conversation, think about outcomes you would be happy or unhappy with.

What’s the ultimate best outcome of the conversation?

This is your “aspiration” or your ideal outcome. For example, in a salary negotiation, this is a number so high it would make you dance out of the meeting. You’d start by requesting your aspiration in a difficult conversation, before negotiating.

What outcome is the minimum acceptable to you?

This is your “reservation” or the minimum acceptable outcome. Anything less would not satisfy you. In the salary negotiation example, anything below this number would make you start looking for another role. Understanding these two possible outcomes is the key to your successful difficult conversation as you understand the minimum you need compared to what you want.

practising a difficult conversation is key for how to get what you want
Talking to someone can help you work out what outcomes are important to you, and you can practise your difficult conversation on them

Pick the right time for the conversation

You may have heard of the famous study that declared that judges are more likely to give a harsh decision right before a lunch break or the end of day, and conversely, to give the most lenient decision at the start of the day or right after lunch. The suggestion was that hungry or tired people will not be as generous as when they’ve had a rest. Interestingly, the study has since been refuted for correlation not causation, as the cases at the end of sessions were cases where defendants did not have representation.

How to get what you want: Pick a time when the person you want to speak to is usually relaxed and will be mentally available to hear what you have to say.

However, the study’s original message still has merit. Have you ever tried to wrap up a meeting because you’re getting hungry and losing concentration? Has your hunger or tiredness ever caused you to lose patience and be short with someone? Remember this when choosing to have your difficult conversation. Using the salary negotiation example, don’t pick a time right after your manager has had a two-hour meeting, has just walked in the door, is stressed under a deadline or when they have their lunch break. For a romantic partner, find a peaceful moment, rather than as they’re rushing out the door.

How to get what you want: Make sure your conversation partner isn’t hangry or stressed

How to get what you want: the difficult conversation template

Before having your difficult conversation to get what you want, it’s important to plan out your talking points. You can mentally prepare or write your talking points down. There’s no shame in having a few notes to refer to in a conversation with someone if you’re worried about forgetting what you wanted to say. It’s a visual cue to your audience that the conversation is important and it’s also a useful tool for you to keep you on track and avoid waffling.

The following approach is a proven method from dialectical behavioural therapy, as developed by Marsha Linehan.


Reflect on exactly what is bothering you and describe it using only facts. This is not the time to say what you want and there shouldn’t be any opinions or emotive language! In our salary negotiation example, the description could be “I would like to discuss an increase to my base salary. I am now earning $50,000 and I would like this to be increased to reflect the role and responsibilities I have”.


Once you have laid out the current situation, you need to explain why it is bothering you. For example, “When I started this role, I believed the remuneration to be fair. But in the last few months I have taken on a lot more responsibility, such as managing the new junior in the team. You have given me great feedback and I believe I am performing well above my job description. This leads me to feel that my base salary doesn’t fairly reflect the value I bring to the company”.


Ask for what you want in the simplest way possible. Make it as easy as possible for your conversation partner to understand exactly what you want. If you are writing a message, start your ask in a new paragraph so it’s not lost among your sentences. Continuing our salary negotiation example, you could say “I would like a 10% raise”.


This is the time to tell your conversation partner why it’s good for them to grant your ask. It is not a time for threats or other manipulative behaviour. In the salary example, your reinforcing reason could be “I think 10% brings my remuneration in line with the industry range, based on this salary survey. Fair remuneration is important to me and will keep me motivated, as I love my job here”. You would not want to say, “If you don’t give me this raise, I’ll quit”.

aggressive body language won't help get what you want
Avoid threats when asking for what you want – they won’t keep your relationship healthy

The only time to dangle the threat is if they have not agreed to your “reservation” ask (defined above in the Desired Outcome section), because it won’t be a threat anymore, it will be your next action. You decided what point you would prefer to walk away when you set your reservation.

Here you’d say “I appreciate you listening to what I have to say. I guess we have a difference of opinion in what a fair remuneration is for me in this role. I really want to stay here but I can’t continue long-term here without fair remuneration, so I’m letting you know that I will now start looking for a new role”. Importantly, do not say this if you believe they could terminate your employment at-will (especially common in the US). This is only something you should do if you trust your manager and if legislation in your country protects employees in employment relations.

How to get what you want: Describe, Explain, Ask, Reinforce

Stick to the topic!

Don’t let the ask get:

  • Watered down. Only discuss one thing at a time. Asking for too many things will mean you’ll only get some (or none) of them.
  • Over-reasoned. Stick to one or two good reasons. It’s hard to dispute one solid reason, but if it’s surrounded by four other weak reasons, it’s easier to decline the ask by focusing on those issues.
  • Distracted. By talking about other issues surrounding the main issues you’ll get distracted from the main request you want to ask.

Are you needing to have a difficult conversation with a friend? It might be time to review your friendship quality.

Romantic partner worked example

couple enjoying time in the sun
Being specific about what you need will help you get what you want, and help you grow closer to your partner.

Scenario: your boyfriend is always late to dates


❌ Hey boyfriend, you are always late when we go on dates.

✔️ Hey boyfriend, tonight you were late to meet me at the restaurant. This isn’t the first time you have kept me waiting for a date.

The first example uses an attacking label (you are always) and generalises the issue. The second example makes it very clear what the problem is by specifically describing the action that has made you upset.


❌ It’s annoying, I don’t understand why it’s so hard for you to get to our date on time. You had all day to get ready, it’s not like it’s unplanned.

✔️ When you keep me waiting, it makes me feel bad and like I’m not important to you. Sometimes I must wait outside in the cold for you and that isn’t a nice way to start a date.

Our first example attempts to make the boyfriend feel stupid or disorganised but doesn’t succeed in him understanding why his lateness is bothering you (which is the real issue). The boyfriend may not see lateness as an issue, so failing to explain what the impact of his lateness is may mean he won’t respect or understand why you value punctuality. Our second example makes the impact of the lateness clear to the boyfriend.


❌ Can you stop it?

✔️ Can you please choose a time that you will be able to make for our next date?

While the request is clear in the first example, it’s asking for a big change in the boyfriend’s behaviour. The second example asks the boyfriend to take accountability for the time of the next date and ensure he will be on time for it.


❌ If you can’t be on time, there’s no point going on dates anymore

✔️ My time is important, and I always make sure I am on time for our dates because I’m excited for them. I’ll look forward to our dates a lot more knowing you’ll also be on time.

A threat is a poor way to get what you want. Another common reinforcement to avoid is “you’d do it if you loved me”. These types of reinforcements try to leverage the relationship rather than have the issue properly understood. It allows the boyfriend to choose to do what you want because he respects and loves you not because he is fearful of losing the relationship.

The reinforcement is not about manipulating your conversation partner, it’s about helping them understand why it will be better for everyone if they can accommodate your request.


Please share with us! Have you got a difficult conversation you need to have? Or have you had one? Did this article help you? How will you ask for what you want?

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