Building a Career as a Fractional Leader

It was the spring of 2023. Nearly a year had passed since I had exited my venture. I had navigated all the emotions of an exit: anxiety, the decision point, relief, praise, becoming a ‘lame duck CEO,’ what I call “The Wall,” a failure to launch, and finally, readjustment and acceptance.

It was now time to search for my next endeavor. I was competent to be a CEO again, but honestly, I wasn’t sure I wanted to carry that load. I could acquire a business, but the debt load and pressure to hit targets again didn’t sound appealing. I could build again from scratch, but I truly didn’t want to go it alone.

Here was the core tension I was facing: I wanted the right combination of flexibility, income, and mission. Let me explain each of these.

Flexibility. I’m a father of four girls, all of whom are still at home. Being a good, present, and available father is one of my highest priorities. Yet, so many roles I was considering would require me to travel, keeping me far from family, or would highly restrict my ability to say yes to soccer practice, taking a kid out for lunch, or simply choosing to call my wife for a half hour one day. Time. I was happy to help build somebody else’s venture, but I couldn’t commit 45 hours of every week to a single one. I wanted flexibility.

Income. As I said, I’m the father of four girls. That means club sports fees, grocery bills, and outrageous energy bills for…long showers. I needed to earn a professional income that could both fund my family’s needs and allow room to save for the future. Most corporate jobs would have cut off my ability to say yes to my kids on a weekly basis, and most consulting jobs provided highly inconsistent revenue. Because my mortgage and my CostCo bill were recurring, I also needed recurring income.

Mission. Finally, I couldn’t bear the thought of just taking a job for the money. I had spent a career living out my calling and building a cause and organization I cared deeply about. Now, I wanted some say-so over the ventures I worked on, whether in business or the civic sector. I wanted to know that my life was making a positive impact on others. I believe that work is, as Dorothy Sayers says, “not primarily a thing one does to live but the thing one lives to do. It is, or it should be, the full expression of a worker’s faculties, the thing in which he finds spiritual, mental, and bodily satisfaction, and the medium in which he offers himself to God.” So, I knew I had to work at something I cared about.

But what was the right combination of flexibility, income, and mission?

I found that fractional leadership—or what we at YOKE call “co-building”—was the solution I was looking for. And today, I think it’s a great way to think about building a career.

The Benefits of Becoming a Fractional Leader

Here’s how fractional leadership solved the exact challenges I was facing:

1. Time & Flexibility. Here’s what I did. I went to a handful of CEOs and said, “I think I can help you build that.” But here were the constraints: I would only give about 1–2 days a week. And it was a range, not an hour commitment, because what I was offering was not my time, but the pathway to an outcome. Time mattered less than actually building the vision. I have experience leading teams, overseeing (and building) processes, and getting results. So that’s what I offered. And three clients said “yes” within about a month. As a 1099 contractor, I was accountable for outcomes and deliverables, but not hours. Fractional leadership allowed me to have a full plate of work, but still maintain the flexibility I needed to work when I wanted. It’s a shift many prioritize when considering where—and what—to build.
2. Consistent, Professional Income. Between three fractional clients, I found I was making more than I ever had before. I had more time flexibility than working a W2 job, and I had the monthly income consistency I was looking for that consulting or project work didn’t provide. I was making about what senior managers make, but still had control over my life.
3. Working on Mission-First Ventures. When I sat down with each CEO, my internal dialogue was, “I love what they’re doing, and I could totally help them, but they can’t afford me.” Fractional leadership opened the way. I could still lead and guide specific teams, but I knew they didn’t need me full-time. (Actually, I believe that full-time would have been problematic. I would have run faster than would have been healthy for the teams I was joining. See more about that below.)

After doing the work of a fractional leader for several years, I realized that I received at least four additional unforeseen benefits:

• The Camaraderie of a Team. Being on a mission-driven team again was great. I didn’t want to go it alone, and now I had a few highly committed teams that I could play a key part in helping.
• De-Risking My Sources of Income. I was paid monthly by my clients, like any employee, but now as a 1099 on the leadership team. Because not 100% of my income came from one employer, I felt tremendously more comfortable. If I lost one, I was just fine financially. I could readjust, take my time to find a new client, and still cover my bills. And this led to…
• Better Management Presence. Because I had more diversified sources of income, I felt far more open to be honest. And on each team that I was leading, this is exactly what they need. Advisors/consultants often don’t have enough insider knowledge to speak truth to CEOs and their teams. But here I was, taking real responsibility for outcomes. Because this was the case, I could say what needed to be said in leadership team meetings. A curious result: this made me even more valuable to the business. So, for example, when I said, “Our sales process is a disaster,” or “I think you and your senior VP need to work through your trust issues,” it wasn’t speaking as an outsider throwing stones. I was an insider, committed to solving the problem alongside the team. I had the knowledge of an insider, but the objectivity of an outsider. And this made me a far better manager, ready to build but also to speak truth. And if I were to lose a client over saying an honest word, I still knew I had other sources of revenue (but that has never happened).
• Professional Growth. Fractional leadership increased my range in a really healthy way. The challenge with our careers is that we become highly paid technicians. We get a narrow skill set that somebody will pay for, and we build a life around it, until something changes, like a disruptive technology. I worked across three vastly different industries, using my core skill set, and grew tremendously as a result. I offered those cross-disciplinary benefits to all my clients, helping them see blind spots, even while I was overcoming my own.

What’s Good for the Leader…Is Good for the Business

But what about the business? Was fractional leadership as good for the businesses I served as it was for me?

Absolutely. Here’s what I learned:

1. Owners just need somebody to do it. As I sat and listened to owners at the beginning of my fractional journey, it became clear that they didn’t just want my advice. They wanted me to go and just do what they had envisioned. For two owners, they had a vision but not the know-how to turn that vision into a strategy and then core operator procedures. For the third owner, he just had too much on his plate and needed another leader around to help think, strategize, prioritize, and get things done. Fractional leadership says to an owner, “Let’s go build this together,” rather than “Here’s what you really ought to do.” Game changer.
2. Owners are cash-strapped and need leadership talent at entry-level management costs. None of the owners and CEOs I spoke to could afford me full-time. The solution: fractional leadership. This gave them access to me as a leader on their team for about the cost of an entry-level manager in their industry. It was a great deal for them, as they could now delegate a large initiative or project to a leader, without even knowing the best next steps. I’d do that for them.
3. Owners need long-term, steady support to achieve their goals. Not everybody will agree with me on this, but here are my two cents: most ventures don’t need “speed and scale.” They need good, consistent leadership over time to figure out, say, product/market fit, to manage a team, and to build trust with clients. With fractional leadership, we had the time to figure out the right model, build momentum, and grow. And the results: amazing, strong, incremental growth with three clients. Not a rocket ship, but the kind of organic growth that is healthy.
4. Owners don’t just need to delegate tasks; they need to delegate problems. If you know a workflow that can be automated, just have an AI agent do it. If you have a clear list of unconnected tasks that need to be done, hire a virtual assistant. But if you have vague visions, too much on your plate, a lack of clarity about the future, or just the feeling of being overwhelmed at all the options before you—you need a leader to do it.
5. Owners need flexible hiring solutions. I’ve been a CEO. I know the weight of hiring leadership roles as W2 employees, knowing that my performance directly impacts that person’s kids. And I know that my customer base is not unassailable. The future isn’t set. Hiring a fractional leader transforms hiring from an on/off button to a lever, scaling up or down as the future demands. Fractional leadership solves a key problem for owners: hire just what you need, when you need it.

Navigational Hazards of Becoming a Co-Builder

I’ve found that becoming a co-builder (fractional leader), however, has some hazards that need navigating.

• First, all of my clients have tried to hire me full-time. I was flattered, really. But because of the reasons listed above, I respectfully declined. I had to communicate to them that staying fractional didn’t mean I was any less committed to their venture. Just like a parent with many children, I had to communicate my care for them, their vision, and their team—while maintaining my time boundaries.
• Second, as businesses scale, your job will change. And as a fractional leader, that’s fine. Replace yourself and level up. You move from projects to management, or out of one management role to another. You need to continually cultivate a range of skills. If, for example, you’re good at numbers and are a fractional CFO, can you also grow into a significant manager role, with all of IT, HR, Admin, and accounting reporting to you? Or, if you’ve been an operations manager, can you also develop a relationship-first sales skill set, and so help build out a sales team? Change is inevitable in all living organisms. You can expect it as a co-builder.
• Third, you need to set limits on your time—and you must use your time well. Fractional leaders need to time block well. This, however, has another unforeseen benefit. It forced me to decide what I can and cannot do in any given week. That, in turn, led me to developing another core management skill: delegation.
• Fourth, you need to master delegation. Rather than “get pushed down” the organization (doing entry-level work), my time constraints forced me to decide what tasks only I could do as a leader, and which ones I needed to either delegate inside the organization or hire a contractor to do. This “forced delegation” then meant that I saved the business money because I was hiring somebody who was far less expensive to do the task that was on my plate. This forced me into wisdom and remaining in a leadership role in the company.
• Finally, you need to master context switching. Context switching is the ability to cognitively switch between different types of tasks or environments. My three clients were a small business, a university, and a church. Each is a very different world with very different expectations. How I manage this: I can take calls from any client on any day of the week, but I block full or half days to work on specific tasks for my clients. There’s more here (something we address in YOKE training with our co-builders), but suffice it to say that great co-builders have the ability to both switch between different environments and manage time, energy, and priorities with excellence.

Co-Building Isn’t For Everyone…

I will say, however, that co-building isn’t for everyone.

These folks should steer clear of becoming co-builders:

1. The Unmotivated. If you’re just looking for a “cush” role, it’s not for you. Do something else. If you don’t have an intrinsic desire to help owners and CEOs build great ventures, being a co-builder won’t fly because it’s too easy to take advantage of the time flexibility. If this is you, get a W2 job at a place with low expectations.
2. The Risk-Averse. The reality is, a good fractional executive is an entrepreneur managing a handful of high-commitment clients. You could lose those clients! But here’s the deal: at the top of any company, you see risk. There really is no such thing as a 100% “stable income.” There is some fluidity to income as a co-builder, just as in a business sales can increase or decrease. (We at YOKE can, however, offset some of this by helping find new clients, helping to manage a P&L, and helping to provide ideas, solutions, and networks to help clients succeed.) You can either acknowledge this risk at the top of a business, or you can be shocked when, one day, you lose your job because your unit wasn’t profitable. Risk is everywhere. In my view, it’s better to see it and manage it rather than pretend it doesn’t exist.
3. Non-Leaders. If you show up to work and wait to be told what to do, becoming a co-builder also isn’t the right fit. Co-builders are always finding ways to go from vision to reality, connecting the dots of strategy, team, capital, and operations to build, grow, and scale great businesses. They take initiative and are self-driven.

The Co-Builder Advantage

In summary, co-builders enjoy time flexibility, consistent professional income, and the chance to work on mission-driven ventures. In so doing, they get the added benefits of professional growth, the camaraderie of a team, a de-risked income stream, and greater managerial presence.

The businesses that hire co-builders get bright, character-first, experienced leaders who execute their vision, are stable and consistent over time, can adopt—and solve—problems, and can do so at a fraction of the cost of a full-time hire.

Hiring or becoming a co-builder isn’t right in every situation, but for many, like me in the spring of 2023, it was an answer to prayer.

About YOKE

YOKE is a company that specializes in fractional executive placement and support. We serve the builders and businesses ready to grow together. 

For senior leaders looking for their next role, YOKE offers a suite of services:

• We help create proposals and contracts to work with clients.
• We help co-builders set competitive rates based on their experience and skillset
• We can serve with onboarding and creating expectations for a fractional leader and their clients. We help with conversations around time, expectations, and what success looks like.
• We can help fractional leaders think through your own LLC (if need be), finding a bookkeeper, and advising on how to build a strong, stable fractional executive business.
• We help you think about how to build your ‘fractional executive business,’ while focusing on the types of gigs you love doing.
• We can manage all billing and backend for you, so you can do what you love.
• We can help with training on areas of business leadership you’re less strong in, but your clients may want/need, ranging from operations to finance to business management.
• And we’re creating a community of fractional leaders focused on wisdom in leadership on the back end that can help you solve problems for clients and grow as a person.

If you’re interested in hiring a co-builder or becoming a co-builder, we’d love to hear from you.