Hard Conversations


Animated picture of a man talking to an elephant.

hard conversations


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Here’s my advice on how to handle hard conversations with clients. Either they cut off contact after a proposal has been sent, don’t pay your invoices, or try to push you out of your scope of work.

A process should be established with clear timelines and methods of communication outlined in the contract. Attention should be paid to any scope changes, and being understanding and kind is important when following up on invoices and payments.

  • 00:00 Handling the Hard Conversations: Prospect Ghosting, Scope Creep, and Invoices
  • 04:57 Establishing Processes to Handle Clients Who Ghost You
  • 10:19 Learn How To Say No and Manage Invoices With Kindness and Compassion


The transcript is below if you would prefer to read this yourself instead of watching the video!


Hi and welcome back or welcome to Sidekick COO. I’m Sandra B, your Sidekick COO and today we are gonna talk a little bit about the hard conversations that you have to have with clients in your business and what to do. 

So we’re talking about ‘prospect’ or when a client ‘ghosts’ you and you have deliverables that have already been done, when scope starts to creep, what to do, and you know, following up on invoices and all of those lovely things. So let’s get to it. 

First of all, for all of these things, the answer to how you’re going to handle them is really to

Look at your Process

Which means you have to have one! You have to have a process for dealing with all of these things in your business and a lot of the time, you’re not gonna have a process for it until it happens. Unless you’re listening to this video and it hasn’t happened yet and you’re thinking, “Ooh, I should have a process for that”. If that’s the case, document a process so that you know if it does happen, and how you’re gonna deal with it. All right? You’re always gonna refer back to your process. 

What should the process be? 

For instance, when you have a prospect, it’s somebody that is potentially going to be a client. They’re not a client yet, they haven’t paid you anything, they haven’t signed anything but you’ve had a discovery call & you’ve sent them a proposal and now nothing…It’s just crickets. 

For something like that, typically what I do is I just have a certain number of times that I’m willing to follow up with people. I’m not here to chase anybody. If somebody wants to work with me, they’re gonna work with me and if they don’t wanna work with me, they’re not gonna work with me. What I have found a lot of the time is that the people that ghost me, which is super, super rare, but if they do, it’s usually just something’s happened in their business, something happened in their personal life that just took them away and they totally forgot to follow up. Or, they had it in their head where they’re like, “I need to follow up with Sandra” but you know, stuff just keeps happening and it just doesn’t make it on the priority list. 

So typically those people, if I ever have had somebody that completely ghosted me, I think they’ve all ended up reaching out to me at some point in time, profusely apologizing. So I don’t think I’ve ever really had anybody just completely ghost me. Maybe in the early days, I might have, I just can’t remember. 

It’s really about not counting your chickens before they’re hatched, right? So I don’t put a lot of expectation on a discovery call or a proposal sent out or I try not to as much as possible. Even though I might send it to somebody that I really, really wanna work with, I try and just divorce myself from the expectation and say, “well, I’ve sent it out” and you know, “now the ball’s in their court and I can’t control that. So there’s no reason for me to worry”. 

What I will do is…I send the proposal and if I don’t hear back from them again, (this depends on how busy I know they are) so if it’s somebody who I know they’re very busy people, I’ll wait two days. If it’s someone who I don’t really, really know that well and I don’t know much about them, then I just wait one day. But that first interaction is literally just me saying, “Hey, just wanted to make sure that you got this proposal that I sent you on this date. Let me know if you have any questions at all”. If it’s a new person, I might say something like, “and just a reminder that this proposal is valid until X date”. 

Usually, that expiration is in the original email, but if it’s somebody that I really don’t know, I’m gonna remind them that there is an expiration date. So it’s just basically, “hey, wanna make sure that you got this? If you didn’t get it, let me know and I’ll resend it asap. Otherwise, let me know if you have any questions and just a reminder that the proposal expires on X date”. If after usually about three days, I still haven’t heard from them, I’d send a little follow-up that says, “Hey, just checking in, making sure everything’s okay. I haven’t heard back from you yet and you know, I know you’re busy so I’ll follow up with you again on this date if I haven’t heard back”.

You just kind of keep it light and no pressure really to hear back from them. Just being understanding typically opens them up a lot if you’re really nice about it, a lot of people will be like, “oh my gosh, I know I’m so sorry. I will have it back to you by this date”. Whenever it’s going to expire, I’ll do a reminder three days before and then the day before. If I haven’t heard from anybody, like if at any of those times I don’t hear from them, usually that’s it. I don’t follow up with them again afterwards with anything. 

If they come back to me, it’s a whole new process and there’s a whole new timeline. That proposal expires and it is now expired. Especially if they haven’t responded to me at all and also depending on what they say when they do come back. If it’s a really kind of lame reason, there’s a good chance I’m just not gonna work with them. But the key is just having that timeline down for when you are gonna follow up with people.

Now, when it’s a client and they ghost you and there’s like deliverables involved, maybe you’ve already done the work and you haven’t gotten paid, or maybe there’s something that you need in order to do the work, Those two situations are different and you should have two different processes for those. But again, it’s gonna be about having that process set up and then just following your process on when are you gonna follow up with them.

I do highly recommend two things in this area, especially when dealing with clients. 

    • Have multiple ways of getting in touch with them. 

Obviously their email, maybe a DM, maybe something like Voxer or WhatsApp. Maybe (did I say phone number?) phone number if I haven’t sent that already, and mailing address. You definitely want to have multiple ways of contacting them and their mailing address is super important because that’s how your lawyer is gonna get in touch with them if necessary.

    • Have your process documented

Again, you’re gonna have a different process depending on the situation. Is this something where they owe you money or is this something where a project can’t continue because you’re waiting for information on them and you’re going to have that outlined. 

If this is an existing client that you have a really good relationship with, then you might want to, hmm, not change your process but just mod…I guess modify (which means change) lol modify your process just slightly for existing clients with who you have a good relationship with who like this is the first time. If you’ve been working with somebody for like three years and this is the first time they’ve ever ghosted you, then likely it’s just something big in their business happening. There’s something big in their life happening and it’s actually not them trying to like go to actually ghost you. 

In those cases, I don’t always follow the exact process a hundred percent. Also, it depends on if the person is responding back to you as well. It might change your timelines on when you follow up and things like that if somebody’s responding back to you. If you have a process where you send a reminder one day, wait three days and then send another reminder but you hear back from them the day before that second reminder, you’re not gonna send it. If you already heard back from them, you’re not gonna send the reminder the very next day. It just doesn’t make sense to do it. 

Having some reminders automated is great, but you really have to think about the process as a whole and know what the process is so that if there is an automated reminder that’s gonna go out and you can’t turn it off for whatever reason, you would let them know. If somebody’s actually reached out to you already, you can just let them know, “Hey, thanks so much for letting me know. Just so you know there’s probably gonna be an automated reminder happening, you can just ignore it since we’ve already made these arrangements”. 

If somebody is a brand new client and I have never worked with them before and I don’t know anything about them and I have don’t really have a relationship with them, then I’m probably gonna stick with my process pretty darn strictly. Which would in include sending something off to my lawyer if this person owes me money. If they get to a certain stage and it goes to my lawyer and my lawyer sends them a nice little message that says, “Hey Sandra’s done these things for you and you have not paid, you have to pay” typically that gets most people to pay.

I’ve only ever had to do that like three times in the last, you know, eight or whatever years. So actually not even three times, maybe only one time in this business and the other two times I’m thinking about are before I started this business like 12 years ago. So yeah, it doesn’t come up often that I actually have to send anything through my lawyer and that’s only if money is owed.

If it’s just that I’m waiting for them to send me information in order to move forward on a project, then I never send anything to my lawyer for that because it doesn’t really matter. I just let them know, hey, you have until this date to get me this information or else I’m going to move on and you’ll have to get back in line.

Again, this is all processes that you’re gonna follow, but also especially with clients, it is things that you’ve already outlined in your contract or your Statement of Work. You should already have something signed by them that says:

→ You’re gonna do this

→ They’re gonna do this

→ This is what they get from you

→ This is how much they’re gonna pay for it

→ These are all the timelines 

→ These are the cancellation policies.

All of that should already be agreed to in writing “in legalese” so that you have something to fall back on in order to, you know, make sure that nothing comes back to you legally speaking. If you have a cancellation policy where it’s like if you wait x number of days, the person is X number of days late getting you content in order to do a deliverable, then there’s a pause in the project. If that’s in your contract or statement of work and it has been signed and everything, then you can go ahead and pause that project and not have to worry about them coming back to you saying, “Hey, you messed up my whole business because you didn’t deliver on this”. 

Having that contract, that Statement of Work and then the processes and procedures that you’re gonna follow in all of these situations, those are gonna be your key to having those difficult conversations. It’s just reminders being sent out. 

When scope starts to creep, that’s when like you typically have to have a conversation because this is different for every client. How they do it is different and how they try and sneak it in there, is different. So usually what I do is the very first time that the scope starts creeping, I will say (and I am not a hundred percent perfect with this. I have a hard time saying no, but I am getting better and I am practicing) but as soon as somebody requests something that is out of the scope of the agreement, you should be deciding

    1. Is this something you’re gonna do for them? 
    2. Is it gonna be something you do for free or something you’re gonna charge them for?

Those are the first two decisions that you need to make. Then you need to go back to them and say, “hey, just so you know, this little piece of work that you have asked for is out of the scope of our original contract. I’m happy to do it for you, however, it’s gonna cost you X number of dollars” or “I’m happy to do it for you and I’ll do it pro bono this one time but I wanted to let you know that One – it is gonna add this much time to our timeline for delivery and also Two – that any future requests for things outside of the scope would result in additional fees”. 

Making sure that you either are charging them for it or you’re letting them know that in the future you’re gonna charge them for it regardless if it is outside of the scope of your original agreement. Just makes sure that they understand that you’re not someone that they can just take advantage of. 

The last thing I just wanna cover is

Following up on invoices

This is one thing that a lot of people are uncomfortable doing and again, it is just about having a process to follow and being human as well. In all of my years of working in every industry that I’ve worked in, I can tell you like the number of people that are actually out there trying to take advantage of you is very slim to nil. Even the people that are out there who they’re not necessarily out to take advantage of you, but if they feel wronged they’ll just like, you know, flip on you. Even that is a very small percentage. 

Most people:

✅ want to pay for work well done

✅ want the work to be completed

✅ are happy to pay

So, when you’re doing your invoicing policy, and of course, this might depend on, you know, the industry you’re in, sometimes you have to be a little bit more strict than others, but for the majority of people that I know, the majority of the people in this online space, you can afford to be kind. You can afford to give people the benefit of the doubt and not get that lawyer involved in your very first email (which I have seen people do). They’ve said “Just so you know if this invoice isn’t paid, I’m gonna have to refer it to the lawyer or escalate it” and they CC their legal team or whatnot. 

I don’t recommend doing that on the very first invoice. As I said, most people wanna pay. People who are having trouble with the invoice for some reason, won’t respond well if you immediately threaten legal action in the very first email. But if you are open to having a discussion about it and you say, usually what I do is I say, “Hey, just wanted to check in. This invoice is overdue, is everything okay? Let me know if you have any questions about anything” or whatnot. And just being open to having the conversation. 

I’m pretty open with, you know, making allowances for people depending on the person. If it’s somebody that I’ve worked with a lot or I know people who have worked with them a lot and there’s never had a problem and this person is, you know, has a financial issue, I’m happy to make accommodations in order for them to pay over a longer period of time. If it’s somebody brand new and I don’t know anything about them, it really depends on what I can know about them and deduce from them but I typically try and just be kind and understand that most people want to pay.

So again, have your process, follow your process, but don’t automate the crap out of it so that you can’t have any human interaction because that tends to cause more problems than it saves. 

That’s all for today. If you have enjoyed this, and have learned anything from it, don’t forget to like and subscribe. And if you know anybody that needed to hear it, please share the video with them. 

Why don’t you just go and do that now? I’ll wait. I don’t mind. 

And always together we thrive. 

Have a great one.

Meet your host

Sandra Booker, Founder of Changemaker Inc. (home to Sidekick COO and The VA Studio) and creator of Scale Society and The Advisory Board, is a mentor, Fractional COO  and growth strategist. She specializes in helping overworked, overwhelmed, multi-hatted entrepreneurs become the CEOs of sustainably scalable, and powerfully profitable businesses. 

After helping local businesses thrive, and receiving accolades in her community (like the 40 Under 40 award) Sandra turned her attention to the world of online service providers, and her clients include familiar names like Chanti Zak, Tarzan Kay, and Laura Belgray.

In her (efficiently used) spare time, she teaches others how to build and grow their own 6-figure virtual assistant practices and is on a mission to create a million jobs by helping her clients and students scale their businesses.

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