How to Have Tough Conversations

Whether you’ve been in business for a few months or a few years – one thing that is a constant is needing to have tough conversations.


But I have good news for you – it gets easier!


Whether it’s letting a client go, raising your prices, talking with a team member that’s not holding up their end of a contract or turning in their work on time – having these conversations is a business skill that you can learn as you go.




Here are some simple strategies that will lead to effective tough conversations:



First, let’s talk about having these conversations in person/Zoom. This improves the chance that what you say will be explained or understood in context. There’s only so much we can write or want to write in an email. Meeting in person or via Zoom is the best first start for many tough conversations. Don’t surprise people with the topic and/or don’t let them wait for days not knowing what you want to talk about. Ambushing someone with a tough  conversation when they think they’ll be discussing something else isn’t professional or fair. I.e. treat people the way you want to be treated. Make sure you have the space not just to say what you want, but also to listen to their point of view. This probably should be a stand-alone call or at least an item on an agenda with time space. It’s also always best practice to follow up after the conversation with a written summary of what was talked about and any action items from that talk.


Are there times when you don’t want to have these conversations in person? For sure! If there has been any type of purposeful or otherwise misunderstanding in the past, it might be best to use email as written documentation.
I hope no one ever works with someone like this, but if anyone has been unkind or abusive, save your sanity and have this conversation over writing. If you know for sure the person on the other side would want to read something and prepare for a conversation, then sending an email is a great idea as well. There are enneagram types and personalities who want time to prepare mentally for any meetings, especially ones that could be emotionally charged. Trust your gut on this and be brutally honest with yourself. There is a difference between not wanting to have the conversation and making excuses. In most cases, you and the other person will feel so much better if you can have this conversation in person.


Next, know what you want to say. Our goal is to be honest and not hurtful. It could be tempting to tell someone “I’m not doing this type of work anymore”, but that just sets them up to have hurt feelings later. Honesty shows respect and – we’re all adults – we can work with honesty.


The first place I look before having any type of conversation is myself. Have I been clear in my expectations? Have I been clear with my boundaries? If it’s a team member, have I set them up for success with clear instructions and due dates for projects? It could be possible that what you want to say after this assessment is – “I found myself upset because x wasn’t being done this way or by this date, but I realized that I’d never clearly communicated that expectation to you. I’ve _______, please let me know if you have any questions. If something isn’t clear or I’m holding you up on anything in the future, please let me know”. Not only is this a needed step, but you are also leading by example and showing what it looks like to make a mistake and take responsibility. By doing so, you are creating that company culture.


If you’ve done this assessment and a conversation still needs to be had, I’d still lead with where I take responsibility.


Examples: Project Due Dates
-We haven’t stuck to due dates in the past.
-I’ve realized I’ve set the tone for this.
-I want to have integrity with these dates moving forward – what can we do to get there?
-Here are some of my ideas – do you have anything to add?


Examples: When you are certain you are not at fault
-I’ve noticed _____.
-When this isn’t done on time it causes other team members to work late or extra hours or these mistakes cause people to not be directed to the correct link and we lose that sale, etc.
-Is there something going on?
-What can you do to fix it? Pause and leave it to them to make suggestions.
-Is it ok if I check back with you in ___ days/weeks, so we can see how things are going and if you need any other support?


You might be tempted to go on and on, but it’s best to keep the conversations and the emails short and sweet.


Two extra special tips to help you have these tough conversations:

  • Bribe yourself!! Examples of this can be I’ll order a sushi dinner or go get a nice cup of coffee shop coffee as soon as this is done (self-care).
  • Reach out to an accountability buddy and send them a Voxer of what I needed to do and then a follow up once it was done.


If you want to save time, simplify, and use a proven template for having hard conversations you can find my Tough Conversation Templates HERE.



If you’re building your business and want more time freedom check out the No Sweat SOP Templates HERE.



Connect with me:

Instagram: @juliecalcoteobm

Hiring Freebie: www.julietraining.com/starterkit


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