086: The Cyrano Strategy for Delegating Important Comms
8 Dec 2025 · 16 min
Jenny Blake explains the Cyrano strategy: hire a strong communicator to handle client emails while you coach behind the scenes in Slack or Help Scout. She now only takes calls after clients pay a deposit, uses templates and TextExpander to scale responses, and documents everything so the role can transfer later.
Questions this episode answers
April 22, 2022.
She only gets on the phone once a client has paid a deposit for an event.
Chapters
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I just want you to know that delegate does not mean abdicate. Just because you delegate and you bring on a team member to help be your front lines of communication with clients doesn't mean you're not involved. It doesn't mean they have to know everything under the sun into the future of how to respond to every client, every situation, every opportunity. You're going to be there hiding behind the digital bushes, coaching them, guiding them, helping them understand how to reply. And yet the burden will not be on you to maintain everything, to keep all the balls in the air, juggling absolutely everything, including for your most important clients.
This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Hello. Hello my friends. Today's episode is a quickie on something that I've come to call the Cyrano strategy of delegating important communications. In my many years of doing business, it's been 11 now. The very last thing that I ever gave up that I ever decided or took the leap to delegate to somebody else was interacting with potential speaking and licensing clients. I held this so close to the vest because these were my highest paying clients. They were my VIPs. I would get so nervous if I saw an email inquiry come in with a big brand name company in the domain of their email address. And I just kept thinking over many, many years, there's no way I could delegate this. There's no way I could assign this to someone else. I wouldn't trust that it would get done right. Or maybe I would offend the person emailing me and they would wonder why I wasn't replying. I don't know. I had all these weird thoughts that held me back from getting help in this area. For a long time I was the one talking to potential Speaking clients having the intro or exploratory call, scheduling those meetings, I would send them the speaking agreement. I would then do a pre event strategy session. I would go deliver the talk, I would send the invoice. If there was a second part other than the deposit. You get the idea. I was doing it all. And I felt that because the volume wasn't that high, maybe, you know, in really good pre pandemic days, I would travel to do two events a month. That would be a really full calendar. And that was easy, easy enough for me to manage. But as the business grew more complex, I just realized I was no longer going to be the best person to be the fastest responder or the best schedule coordinator. And I know many of you have probably given up sending invoices long ago. I never minded doing it. There was something about Happy money. That's the title of a book. There was something happy money to me about creating an invoice for these big checks, because speaking was before licensing, my highest revenue generating activity in the business. So I just never minded any of these logistics too much. But over the years, as the business grew more complex, I realized I have got to take a risk. I've got to do what I say in the book, double what I delegate, and really push myself to my delegation outer reaches of my stretch zone and see if I can get somebody else not just to assist with potential clients, but, but actually do most of the work upfront. And now to the point where I only get on the phone once a client has paid a deposit for an event. So I'm no longer holding the exploratory call. I'm no longer sending information about pricing, the speaking agreement, the invoice, somebody on my team handles that. But crossing that bridge, going from zero to one in this area or something that feels really high stakes is incredibly nerve wracking. And I'm hoping that the Cyrano strategy can help those of you who are curious about doing this, but nervous to help you make that leap. Because the big secret is that you're still gonna be pretty involved, at least in the beginning. Let's talk about why I call it the Cyrano strategy in the first place. And by the way, the full name of this character from fiction is Cyrano de Bergerac. And I asked Michael. It's really intimidating to live with a fluent French speaker because sometimes before I come record a podcast episode like this one, I'll ask him, you know, hey, can you help me pronounce Cyrano de Bergerac?
And he will just look at me and go. Just say it like that. It's like, don't even attempt the French version. I wish I had him here. I'm in the recording studio. I wish I had him here to tell you. It's like Cyrano de Begerac. I don't know, with the fancy R's. I'm sorry. I apologize to all French speakers of my bungling this pronunciation. So Michael basically told me on this one, don't bother. Just call it Cyrano de Bergerac. Soft A, not Bergerac. He's like, let your American version be what it is. Okay, so the Cyrano de Bergerac is a play from Edmond Rostand. It was later made into a movie called Roxanne with Steve Martin. Maybe some of you remember it where Cyrano is this poet and he has the most exquisite mind, and he falls in love with his beautiful cousin Roxanne. And even though Cyrano is brilliant and charismatic, he has a shockingly large nose. So he considers that he's too ugly to even risk telling Roxanne his feelings. And then to make a very long story short, there's this very handsome nobleman named Christian. And the two of these guys, these two fellas paint hair up where Christian, the handsome one, starts courting Roxanne. But he's dumber than a box of rocks, and he doesn't know what to say. He embarrasses himself deeply when Cyrano is not there to help. So Cyrano hides in the bushes and whispers to Christian what to say and how to woo Roxanne. And so we have this melding of mind, let's say looks and personality. And now Cyrano can express himself secretly from the bushes and court Roxanne via Christian. Okay, Now, I won't tell you the end of this story. You'll have to go watch either the movie with Steve Martin or go read the book. Summary.
Now, this metaphor is going to fall apart a little bit because we're not saying that anyone in the business is ugly or dumb, okay? But when you're first delegating, what I want to encourage you is that if you find a team member, even part time, they don't have to be full time. I'm always saying that. That they don't have to know the ins and outs of your business in order to help you tremendously in this area. They don't have to be the one that's been working on these programs for 10 years. They don't have to be the expert knowing every last detail. What I would look for is somebody who has experience with their career and with communication. You want somebody who is a strong communicator. They can write clear emails, they're warm, they set the right tone. Maybe you want to conduct an interview process where you have people writing sample communications for different case studies. You are going to have a lot of the canned or guided responses already from your years of interacting with your highest level clients. So a lot of this content already exists. And if you've been reading free time or listening to me at all, you will have saved those responses in something like textexpander. I also use Help Scout for managing our team inboxes and you can save emails there. Gmail also has a canned response feature. Whatever you do, put them in one place. I like textexpander because it's app agnostic and that comes with you wherever you are on your phone or your computer. And you can quickly, with one little keyword, populate a three paragraph message. So let's say somebody's interested in your programs. You would already have a pretty well thought out reply of what to say to somebody who's interested. Maybe in my example, they want to know the price of a keynote speech. Okay, great. Tell us more about your event. When is it? What's your budget? Jenny starts at this rate and we'd love to work with you if it's a fit and so on. Then you're going to have your own messages that the person will help guide and craft and customize around. It's a yes or it's a no. If it's a yes, great. Next steps are the agreement and getting some of the logistical details pinned down. Maybe scheduling the pre event strategy session. The reason I call it the Cyrano Strategy is that what I have found is that as long as I'm delegating to someone who's a strong communicator and once they meet with me they can figure out what to say or how to craft things or how to answer a potential question from a client. I'm there hiding in the bushes, AKA our Slack channel or our notion pages guiding them. So yes, they have the base template, but they don't always know what to do or what to say or how to handle each individual request. Maybe there's a little budget back and forth, maybe it's a timing issue, they want it yesterday and my schedule's full for two months. There's always little things that come up, but the Cyrano strategy is there. I am hiding in Slack, hiding in the Help Scout notes we can send back and forth on a certain email message or in notion talking about a project and I'm able to provide feedback before they respond. Yet I am not the one responding. So in this case I realize I've made myself to be the one with the big nose hiding. And I have to say it takes a really bright, warm team member. There is nothing dim about the role but that they can have confidence knowing they don't have to have all the answers and neither do you in order to start delegating this area. What I found was that it was conveying too much that I was a one woman shop when I was doing all the things the exploratory calls, scheduling, invoicing agreements, then the strategy session, then the keynote. It didn't send the right message. It didn't show how valuable my time had become and how much complexity I was juggling in so many other aspects of the business. So by having a team member take over, it sends a message that time with me is rare. It is valuable that they're going to get me once they've paid and I go to the pre event strategy session and when I show up it's more meaningful. And in fact they probably feel relieved that all the details are taken care of with someone on my team who is making sure that nothing falls through the cracks.
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So the reason that I love the Cyrano strategy is it makes the time with me more valuable. Also, my team member is much stricter about sticking to my pricing than I am. Sometimes reflexively she'll just put out the full fee, whereas I might have said oh well, for this client we can say half off or whatever. And so I love having this person to check me and not have me over, give or underprice, things like that. I also love knowing that this team member, their sole role is keeping an eye out for red carpet clients and communicating with them and making sure that I don't forget. Because as business owners, we're just juggling so much. There's every area of the business, every team member. For me, the big creative projects, these things get my time and energy and attention. And I'm not going to be the best person to remember what we owe which client and when. And so I love knowing that there's someone on my team who handles that, even if she goes to me and we discuss behind the scenes exactly how to respond or how to craft a message. We have tricky client situations come up all the time, and I don't expect her to just know what to do. I'm always grateful for her to make a recommendation and say, here's what I would do, or here's what I suggest we send them. But sometimes it really does take the two of us putting our heads together saying, what the heck is going on here? And we need to go back and forth and have multiple drafts. I'm kind of giving you the behind the scenes, and it would be pretty funny if one of my clients was listening to this exact episode. I just want you to know that delegate does not mean abdicate. Just because you delegate and you bring on a team member to help be your front lines of communication with clients means. It doesn't mean you're not involved. It doesn't mean they have to know everything under the sun into the future of how to respond to every client, every situation, every opportunity. You're gonna be there. You're gonna be the Cyrano hiding in the slack bushes again. Slack makes me jumpy, so I try to avoid it when possible. But for quick or time sensitive, my team and I use slack for everything else. We're communicating in help Scout and in notion. You're gonna be there hiding behind the digital bushes, coaching them, guiding them, helping them understand how to reply. And yet the burden will not be on you to maintain everything, to keep all the balls in the air, juggling absolutely everything, including for your most important clients. You can sleep easier at night knowing those clients are taken care of, knowing that you are putting a premium on your time and your energy and making sure that nothing falls through the cracks. And bonus, you have someone holding you accountable for your pricing and your boundaries. That can be a great middle person between you and your clients. Hope you found this helpful. I encourage you to stretch yourself. Try delegating some of your comms, even if you're right there behind the scenes holding somebody's hand for months in the early days until you get enough of a cadence and they get enough experience and you can get enough captured. Don't forget to document as you go and to tell your team member the same. Nothing, nothing, nothing should live in anybody's mind. So you want to make sure that if you are going to do the Cyrano strategy and provide all this extra coaching and guidance behind the scenes that gets documented in your manager manual in your guided responses so that not only the person gets smarter and more intelligent about how to run this area of the business, but your business information and documentation gets smarter and more intelligent over time. I always encourage people to say, imagine we're going to hand off this role to somebody completely new three months from now, and they don't get to talk to either one of us. Let's make sure that our guide and our materials and communications are clear and up to date so that's possible. Because you never know. Maybe your team member will love doing this kind of work and maybe they won't. But if they don't and you document really well along the way, it's even easier for them to hand it off to somebody else. I would love to hear your take on this or if you've tried anything like it, you can always leave me a voice memo@itsfreetime.com ask thank you so much for listening everybody. Have a beautiful rest of your day.
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