How to Prepare for Difficult Conversations

Difficult Conversations

Between quitting my tutoring job and recently making a big life decision (I’ll share later), I’ve had a lot of nerve wracking conversations lately. I’m sharing tips on how to prepare for difficult conversations because communicating big changes can be really scary! Whether it’s a conversation in a professional setting or a personal relationship, I’ve curated tips to help you communicate everything you need to even when you’re nervous.

Write a Letter You Won’t Send

A lot of times when we’re nervous about difficult conversations, we’re nervous because we have a lot of emotions tied to the decision we’re making. When I quit my tutoring job in March, I felt really guilty about leaving my job because I had a personal connection with my boss after working for her for three years. By writing a letter you won’t send, you can process all your emotions, filter out things that might not be appropriate to say IRL, and learn what actually needs to be communicated.

Difficult Conversations

Make Bullet Points of What You’re Actually Going to Say 

After writing your letter you won’t send, look at your letter again. Within your letter, you’ll see what you actually need to say. I always like to write my main points down on an index card to keep my conversations on track. Writing has always been an amazing outlet for me to communicate as an introvert because I have time to think about what it is I want to say. When I’m actually speaking to people in real life, the words don’t come easily to me. An index card of what I plan to say really helps me communicate everything I need to in difficult conversations.

 

Practice Your Conversation With a Loved One

The scariest part of having a difficult conversation is actually starting it! By rehearsing what you’re going to say with a loved one, you can ensure that you feel prepared to have the conversation as opposed to feeling like you’re jumping off a cliff. Your loved one might even be able to point out things that need to be added or subtracted from your speech. It never hurts to bounce ideas off another person!

Set a Date

The biggest mistake I made in preparing for my last difficult conversation was not setting a date for myself to have the conversation! I was so terrified to take the leap that I ended up procrastinating the conversation until the very last minute. If you set a date, you are essentially setting a deadline for when you need to have “the talk”.

 

Let the Person Know You Need to Talk

This might not be applicable to all difficult conversations depending on the situation, but it’s always nice to let the other person know you have something important to say. If you need to have a discussion with a loved one, let them know when you want to talk (ex: “Let’s talk about _____ when you get home from work”). If you plan on having a conversation in a professional environment, be sure to shoot the person a quick email. This not only holds you to actually going through with the conversation, it gives the other person a heads up.

Whether you’re asking for a raise, quitting a job, or making big changes with a loved one, I hope these tips are helpful! <3

 

Outfit Details

Lulus Cropped V Neck Sweater ($46)

Similar Madewell Midi Skirt (on sale for $50)

Similar GC Shoes Yellow Sandals ($50)

 

*Photos taken in Yerington, Nevada

29 COMMENTS

  1. Omaye | 14th May 20

    This was well informed post.
    Some things are quite hard to do when you are trying to actualise it.
    Sometimes you even practice in the mirror.
    Thanks for the post. <3

    • Jill Gilbert | 15th May 20

      Thank you so much Omaye! That is such a great idea to practice difficult conversations in a mirror! I hadn’t thought of that

  2. Celyn | 15th May 20

    super cute outfit! I love your skirt and also the pop of yellow that your shoes add to the overall look! Great pointers too, thanks for sharing!

    Life is a Shoe

    • Jill Gilbert | 15th May 20

      Thank you so much Celyn! The best thing about this outfit is that it’s super comfortable, although I don’t have anywhere to wear it besides the middle of the desert since we’re all quarantined haha!

  3. jodie filogomo | 15th May 20

    You are wise beyond your years Jill. This is such a good idea for almost any conversation that brings up angst!!
    OXOX
    Jodie
    http://www.jtouchofstyle.com

    • Jill Gilbert | 15th May 20

      Aw thank you so much Jodie! You are so kind!

  4. Radi | 15th May 20

    This is a tough one… I definitely need more practice. Somehow in my head it goes perfectly and then in real life turns out a bit different.
    Thanks for these tips Jill!

    http://www.fashionradi.com

    • Jill Gilbert | 15th May 20

      Thanks Radi! I definitely have the same problem when it comes to difficult conversations. I think I imagine all scenarios of the conversation except for how it actually goes down.

  5. Patricia & Miguel | 15th May 20

    Such a lovely post and full of value.
    Difficult conversations can be really hard to start but we feel like you gave really good information on how to do it! You are amazing and beautiful 🙂

    Sending you lots of love,
    Patricia & Miguel

    http://www.patriciandmiguel.com

    • Jill Gilbert | 15th May 20

      Aw thank you so much Patricia and Miguel! I’ve had to have lots of difficult conversations professionally lately so I thought I’d share some tips on how to tackle those types of situations. Thank you for reading! 🙂

  6. Jennifer | 15th May 20

    I hate having difficult conversations. I am going to try some of these tips next time.

    Jennifer
    Effortlessly Sophisticated

  7. Margot | 15th May 20

    Amazing tips here !
    I always struggle to start a difficult conversion. Putting everything on a letter I won’t send sounds like a good idea for me.
    And I absolutely love the skirt you’re wearing here.
    xx
    Margot
    https://troughthepasturesofthesky.com

    • Jill Gilbert | 16th May 20

      Aw thank you so much Margot! This skirt is surprisingly really comfortable! I hadn’t realized how effective writing unsent letters is! It really helps me collect my thoughts and figure out what I actually want to say to the person.

  8. Naya | 15th May 20

    Omg you are so beautiful! I love these photos of you, Jill.

    The letter idea is actually really amazing. I haven’t done that personally, but I do get how it can help you decide on what are the key points you want to highlight during an actual conversation (if you’re talking one on one). I usually chat about it with my best friends or family first, ask what they think if I write or say XYZ (when it is a serious situation), this way I can see what parts to keep and what to avoid. A longer process, but you do get better at it over time xx

    Naya
    http://www.nayatilly.com

    • Jill Gilbert | 16th May 20

      Aw thank you so much Naya! Writing letters has really helped me figure out what I want to say in my most recent difficult conversations. Bouncing ideas and practicing with friends and family can really show you what you should and shouldn’t say. I hope you are doing well!

  9. Saguaro Style | 16th May 20

    LOVE that skirt and yellow sandals, so pretty together! xx

    http://saguarostyle.blogspot.com

    • Jill Gilbert | 17th May 20

      Thank you so much! This skirt is actually pretty comfy. I like the length because I don’t have to pull it down when I sit down.

  10. Nancy | 16th May 20

    Difficult conversations are always hard to actually do. It is good that you found ways to go through the thought process. I am all about writing a letter that won’t be send. Hopefully it really doesn’t send like those romcoms haha. Practicing the conversation and even voicing it with others is a huge relief. You can get a third party perspective over it. Thanks for sharing all of these great tips for preparing for that convo!

    Nancy ♥ exquisitely.me

    • Jill Gilbert | 18th May 20

      Thanks Nancy! Difficult conversations are definitely hard to figure out especially if you’re an introvert like me. I always like to plan for things and I don’t think I would’ve had the bravery to tackle my recent difficult conversations without taking these steps. I know writing a letter sounds silly (it would be pretty funny in a romcom haha), but it’s such a helpful strategy.

  11. Nicole San Miguel | 17th May 20

    These are great ideas! I remember back when I was in college, I used to have a notebook where I write everything that I wanted to say but never did. It’s just nice to express what you want to say by writing.

    – Nicole http://www.nicolesanmiguel.com

    • Jill Gilbert | 18th May 20

      That is such a great idea to have a notebook for things you can’t say out loud! I definitely don’t stick up for myself enough, but the recent difficult conversations I had to have couldn’t be avoided!

  12. Missy May | 17th May 20

    These are great tips and definitely agree with you. On the other hand, you look wonderful! Gonna have to steal your poses for my next shoot. Ha!

    https://missymayification.co.uk

    • Jill Gilbert | 18th May 20

      Hehe thank you so much! I’m glad my poses come across well. Sometimes I find a flow with posing and other times, it’s like my body and mind become disconnected lol!

  13. Sonia Aicha | 17th May 20

    these are great tips that can definitely make it all easier, thanks for sharing !!
    PS : Love your yellow sandals, so summery!
    Sonia
    http://www.soniaaicha.com

  14. Miri | 18th May 20

    Love all of your points here. I really think that it needs good preparation to have a difficult conversation.

    lots of love, Miri
    http://www.meetmiri.com

    • Jill Gilbert | 19th May 20

      Thank you! I’ve had to tackle many difficult conversations lately so I thought I’d share some tips that have helped me get what I need to say across.

  15. Georgina | 22nd May 20

    Love the outfit!

    Such a helpful post, I always find the ‘send a letter you won’t send’ helps so much.

    • Jill Gilbert | 23rd May 20

      Thanks Georgina! I found that writing a letter I won’t send has been really helpful for me to collect my thoughts when having a difficult conversation!

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