One of the biggest traps I fell into after leaving the corporate world was believing that I needed to lead by example, often clocking twelve-hour days just to prove a point about work ethic to my team. I’ve realized that while leading by sheer effort creates a bottleneck, leading with radical clarity is the true force multiplier that actually scales a business. I’m breaking down how I shifted from micromanaging the "how" to defining clear outcomes for the "who," a strategic pivot that has allowed me to 5X my output, escape the weeds of daily operations, and stop being a prisoner to my own company.
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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.
About Ray:
→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.
→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.
→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com
→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.
→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com
And this is one of them. And it is that leading with clarity, instead of effort or instead of by example, is a force multiplier that will accelerate the growth of your business by multiples.
And what I mean is: when I went out as a solopreneur, I developed some bad habits. Because I came from corporate—you know, I came from Managing Director, CEO roles where I had teams. I was very good at delegating and, you know, hiring the right people, building the right systems, letting them do their work. But I had big budgets, right? And when I went out on my own, I didn't have that same $10, $20, $30 million budget. And so, what I started doing was just started doing it all, right? If I needed a funnel built, if I needed some copy written, if I needed virtually anything in the business, I started doing it all.
And then when I would hire people, what I would end up doing is kind of micromanaging that role. I would hire for a "how" to do something instead of like a "who." Like Dan Sullivan talks about "who not how," and you know, if you hire a "who," they'll help direct you, they'll help create the role, they'll help you learn from them as much as they're learning from you. And if you hire a "how," they're just following your SOPs, following your processes, and then you're just managing tactical execution.
And I hired "hows." And I just found myself in the weeds of the business all the time. And no matter what, as I tried to grow... because I now knew about the funnel, I now knew about the CRM, I now knew how to write copy, I now knew how to create a content system... knowing these things as a CEO, I didn't necessarily know how to do those things, but I knew I kind of did, but I would hire somebody to do it. Solopreneur? I do it myself. Once I knew how to do it myself, I would hire the wrong person and then I would manage them the long way. Because I would be focused on how they're doing the job, and I would try to lead by example.
Right? And similarly, I would exert a ton of effort trying to demonstrate to my team that that's the level of effort that's kind of expected. Like, "Hey, we go hard in the paint," and, "We work our asses off," like, "This isn't a lazy, complacent culture, we need to be driven." And I would lead by example by clocking a whole bunch of hours and pumping in a ton of effort.
And ultimately, what I've learned, and maybe relearned, is that leading by clarity is a way fucking better approach. Because when I hire the right person—which is actually another lesson that I shared, because hiring the right person is 10 to 20X better than 10 to 20% better—when I hire the right person, and then I take the time to clarify to them what's expected of the role, what the boundaries of the role are, what success looks like, and I take what's in my head of what I want from the role... with the right person in place, I can then give them that degree of clarity, turn them loose, truly delegate the execution of something, and really focus on the outputs, and making refinements to the clarity that I've given them, right?
And by doing that, what I do is effectively create massive leverage on my time. Because instead of spending 12 hours a day clocking hours and checking off to-do lists trying to show the team that this is how we execute, instead what I say is: "I'm going to invest all my time into creating clarity for everybody on my team." And now I have—we hired five people this past year—I have 5X the output. Because my job becomes clarity. And then just essentially managing to the outputs as opposed to doing all the inputs to show them how it's done and leading by example.
And that has been a huge lesson for me. Because it's more leverage on my time, like I mentioned. We end up with better documentation, so the role ends up being more scalable. If we need to replicate it, if we need to clone it, if we need to replace for any reason, you know, that clarity that I document, that I establish with people becomes a scalable type of thing. It's part of a repeatable process. And I can document it, I can share that clarity with them, we can use what I want from the role—that document, that foundational piece of like "This is what success looks like" and "This is what I really want you doing," "This is what a home run... like if you want to knock the cover off the ball, this is exactly what that would look like"—we use that in our one-on-ones as a follow-up, and we make revisions to it as needed.
True delegation happens. And what you end up with long term is a much more sustainable business. Because as you add more and more people to the business, it doesn't require more and more of your time, more inputs from you directly. Right? Because you take the time to establish the clarity, and somebody else can come in and execute according to that, and then you can collectively, together, make revisions that are necessary as you keep going.
And I think long term this is one of the ways that you avoid becoming a prisoner to your business. Because I'm going to take the time to develop clarity, and then I'm going to expect you as an A-player to go execute. I don't expect me to have to execute. I expect you—because I've hired strategically—I expect you to go do this. So the business can expand beyond me and doesn't require... and I think this is like a limitation I see in so many businesses, they hit like the million, five million, even ten million mark, and the time of the founder or the CEO becomes the limitation for the business because they're leading through effort and through example and through mechanisms that require more micromanagement, instead of leading through clarity, which enables you to expand significantly.
So, I hope this was helpful for you. Good lesson for me to relearn and to get back to my roots of defining what outcomes are and hiring properly, delegating properly, and watching the business and the team grow and expand. And I have a high degree of confidence that two years, three years, five years from now, this results in a business that is far more enjoyable for me to run and own, and attracts the best people, which ensures we get the best quality of work and everything else that goes along with it. So, again, hope it helps. Adios.
