In Will’s Head: Emails—Or, the Tale of the Squirrel and the Sloth

If you’ve taken a Maestro training, you know our two pillars—control what you can control and mitigate risk. Nobody takes the pillars to heart more than Maestro’s founder, Will Fuentes, and I don’t just mean in high-stakes situations like when closing a deal or meeting with an investor. Will puts just as much work into mitigating risk with every phone call he makes, every meeting he has, and every email he sends.

Our “In Will’s Head” series is meant to shed light on what it means to uphold these pillars every day. Will thinks through all possible outcomes in any situation. He could be sending a message to a prospect, or to the 12-year-olds on the basketball team he coaches. He might be introducing himself to a potential client, or to a friend’s daughter who’s interested in sales.

We don’t need to emulate all of Will’s thought processes—we couldn’t if we tried. But we can learn from his approach and realize that there is more that we can control than perhaps we initially considered. Or we can simply marvel at the thought and energy he puts into something as basic as email.

ALLOW ME TO INTRODUCE MYSELF

“Let’s say someone introduces you to another individual in their network via email—what are you thinking about when you respond?” If someone asked me this question, I don’t think I would know quite how to reply. It would depend on who it was from, right? And whether or not you could help the individual, or if they could help you? Luckily this isn’t the “In Rachel’s Head” series because I (and many of us) don’t have a strategy with which we approach every email. But Will does.

“First is how quickly I can get back to that introduction,” he replies. “I like to move super fast. Is this email for business purposes?” he asks me, but before I can even answer he says, “Never mind, it doesn’t actually matter. Whether I’m getting introduced to a kid or a friend of a friend, my goal is to react to it as quickly as possible.”

“Even for friends and kids?” I question. “Why?”

Will replies as quickly as possible for several reasons. First, he wants to establish consistency in his behavior, “so that nothing ever seems out of turn in terms of my intensity,” he says. “I know what I’m like.”

I know what he’s like, too. Until this moment, however, I didn’t know what I was like—I suddenly feel like a sloth, interviewing a squirrel. A squirrel who is making it clear that I am not thinking through my emails properly.

“The biggest risk,” he says, “is that they think I don’t care about the initial introduction.” By responding quickly, Will is showing that he does value the introduction, plus it gives him an opportunity to judge how important the introduction is to the other person.

Will mitigates several risks by responding right away. If he doesn’t hear anything back and the introducer asks about it, he can say that he responded that day but received no reply. Risk: mitigated. If the introduction came after an emotionally fraught discussion between the introducer and introductee, a quick response ensures the recipient is still in that emotionally charged state. Risk: mitigated.

CONNECTING EVERY DOT

By responding quickly to an introduction email, Will has mitigated a number of risks I had not even considered. Let’s move on to the next scenario, says the sloth to the one and only squirrel who will never get blindsided by oncoming traffic.

“Let’s say you have a new client with whom you’re communicating over email,” I posit. What are you thinking about?”

“Number one is I try as much as I can to avoid any mistakes in my communication with them,” says Will. “Grammar, spelling, punctuation—that kind of thing.”

Now we’re back in my comfort zone. Maybe I’m not so sloth-like after all.

“But I’m also establishing that I’m fast,” he continues, “so if I’m not in front of my computer, I’ll respond on my phone, but be sure to let them know I’m on my phone—so please excuse any errors.” (Never mind. I just fell out of my sloth tree.) “Speed in the advice I’m giving is most important, but with that comes the possibility of mistakes.”

Next comes readability. Not only does Will want to be speedy in his delivery of information, but he wants to be sure the recipient will be able to quickly synthesize the content of his message. Hey, I also think readability is important…He’s moved on. Now we’re back to speed.

“I’m trying to establish with clients,” Will explains, “that if I have the answer, I’ll give it to you right away without wasting time. If I don’t have it, I’ll let you know that I need time to synthesize and do some research so it will be a day or two before you get it. I let them know right away, though, that I’ve received their question and I’m acting on it.”

Will goes on to explain that establishing this pace early with email responses makes using that pace easier later on. If a client were to miss a payment, for example, it’s not out of character for Will to email them right away. But if his intensity around payment is the same as his intensity around solving their problems, there is no cognitive dissonance.

We often talk to clients about “connecting the dots” for their prospects. You understand how your own product feature connects to benefits and to something the client values, but those connections might not initially be obvious to a prospect unless you spell them out.

Similarly, Will connects all the dots for clients. They might think a quick response means he’s not thinking through something thoroughly. They might think a slower response means he’s not working on the problem. Will mitigates each of these risks by clearly communicating in his emails when he needs more time and what he’s doing in that time. Nothing is left to interpretive chance.

EMPATHY MINUS FEELINGS = STRATEGY

“What if you are asking your client a question over email,” I inquire. “Let’s say you’re asking a start-up founder about their sales process. What are you thinking about?”

“How do I write this so that they think logically about the question I’m asking and not get emotional about it,” Will says. He then explains how after he writes an email like this, he’ll read it in different voices to see if there is any way someone could read negativity into it. This surprises me because Will openly tells people that he’s not an empathic person.

“You’ve said that your lowest-ranking leadership trait is empathy,” I say. “But here you are putting yourself in the position of the reader, and thinking about how your message could make them feel. Doesn’t that require empathy?” I’m feeling a little less sloth-like because I think I’ve out-smarted him, or at least out-smarted the StrengthsFinder assessment.

“My number-one strength is strategy,” Will tells me. “That’s the strength I’m leveraging when I consider how my message is landing. Strategically, I need to think about what the possible outcomes of this are and where things could derail. I’m not thinking, ‘Oh, I hope they don’t receive this poorly.’ I’m thinking, ‘I don’t want them to receive this poorly because then it’s counterproductive to what I’m trying to accomplish.’”

Will goes on to explain that sometimes it’s nearly impossible to ask a question without the possibility of someone reading it negatively. For those questions, he’s come up with risk-mitigating phrases like, “curious, not confrontational.” Or when he’s trying not to come across as pushy with an email reminder, he’ll use the phrase, “gentle nudge.”

He mentions other email risk-mitigation strategies—to avoid a client thinking he doesn’t understand their business, to avoid increased friction in the sales process, and to avoid massive misinterpretation. “Doesn’t it make you anxious looking for every possible risk all the time?” I ask.

“No,” Will replies, “it doesn’t make me anxious. I’m good at identifying what’s a real risk, and I can quickly process how to mitigate it,” he says matter-of-factly.” I sit there, exhausted, at the bottom of my sloth tree, wondering what risks that I haven’t mitigated are about to run me over. “Okay,” he says, “gotta jump, I have a demo. Talk to you soon!” and off he scurries.

Interested in learning more about Maestro’s consulting services and trainings? Contact us at mastery@maestrogroup.co to learn more. Squirrels, sloths, and all other wildlife welcome.