What a Fractional Leadership Engagement Looks Like – Part 2

:image-photo:checklist-concept-check-mark-on-wooden-shutterstock_1925103629 copy

:image-photo:checklist-concept-check-mark-on-wooden-shutterstock_1925103629 copy

At this point, you understand at a high level why bringing someone onto your leadership team who’s built a business like yours before will help you. In Part 1, we illustrated a high-level Fractional Leader engagement with a real-life business example. Now let’s take a look at the some of the details involved in a Fractional Leadership engagement.

Accountabilities and Deliverables

You and your FL will agree to certain deliverables or areas of accountability and a time frame in which you expect to see the results you want. This is a critical element of any type of Fractional Leadership engagement.

Here are some examples of the deliverables one Fractional Chief Sales Officer (FCSO) included in an agreement:

  • Lead sales team to achieve the company’s already-established targets for the year
  • Participate in weekly leadership team meetings
  • Document the sales process and ensure the team is trained in it and follows it
  • Determine and implement measurables to which she will hold herself and the members of the sales team accountable
  • Collaborate with the head of marketing to ensure all efforts are absolutely in tandem
  • Evaluate current CRM/technology and improve or revamp as appropriate
  • If a client has implemented the EOS management framework,
    • Hold Same Page Meetings™ with the company’s Visionary (an EOS® term that usually refers to the CEO).
    • Participate in EOS sessions with their EOS Implementer®, if applicable.

You and your FL will structure the accountabilities based on the FL’s proven process and your own unique needs. The important thing is that you and your FL get absolutely on the same page regarding the deliverables or accountabilities so there is no misunderstanding or crossed wires later on.

Time Commitment

Fractional Leaders make three primary types of time commitments: X number of (i) days, (ii) half days, or (iii) hours per measuring period—that is, week or month. Some engagements even involve as much as half-time work; these individuals take on no more than one or two clients. Other FLs work with their clients only one or two hours per week or a half day per month.

You must agree with your FL on expectations when it comes to time commitment because you can’t define the accountabilities or deliverables without knowing how much time the FL has to accomplish them. As Gary Braun, owner of the FCSO firm Pivotal Advisors, says, you cannot expect your one-day-per-week FL to attend five meetings and still have time left over to create sales processes and manage a sales team.

You should also discuss with potential FLs their client load in general relative to his or her proposed time commitment. Mark O’Donnell, Visionary (CEO) at EOS Worldwide, cautions against entering into an engagement when the FL’s client capacity is filled to the max. As business ebbs and flows or an FL successfully enables you to grow, your needs may change.

“It’s set up for failure systemically when they have three to seven clients [if each are ten to fifteen hours per week]. They end up being forced to not do the right thing for one or more of their clients based on a nonlinear growth trajectory of all their clients.”

Another time-related factor is the fact that like everyone else, FLs need and want to take vacation from time to time. If they commit to a certain number of hours per week and a monthly retainer, they build in a mechanism for vacation time in their engagements.


Many Fractional Leaders charge a monthly retainer in exchange for a weekly or monthly time commitment. Some charge for each quarter in advance. And still others charge by the hour. Rates vary greatly depending on a number of factors:

  • The time commitment
  • The depth of the FL’s experience
  • Whether the FL is an independent solo practitioner or using a licensed system (licensees generally charge higher rates than solo practitioners)
  • Whether the FL is part of an Organizational Fractional Leader firm (OFL) (OFLs generally charge more than both licensees and independent solo FLs)
  • The local or regional market (FLs in major metropolitan areas charge more than an equivalent person outside a metro area)

Because of the extreme variation in the size and type of companies, FLs’ experience level, and market rates in each geography, monthly retainer amounts vary significantly. It is therefore impossible to identify a narrow market rate for each type of FL.

Some FLs charge $2,000 for a half day per month or for one hour per week. Others charge $2,500 for a half day per week. Most charge $4,000 or $12,000 per month for a one-day-per-week commitment. I even know of some FLs whose clients pay about $15,000 per month for a one-day-per-week commitment.

Among those who charge an hourly fee, I have seen anywhere between $125 and $325 per hour. Some, both business owners and FLs, prefer the hourly model.

Finally, some FLs agree on a hybrid retainer/hourly approach with clients by establishing a retainer for X number of hours per week beyond which the FL will bill the client at an agreed-upon hourly rate. Another approach some FLs take is accepting a lower retainer in exchange for an equity interest.

Payment Terms

Many FLs, like myself, require clients to pay for each half month in advance, on the first and fifteenth of each month. I personally offer a money-back guarantee on the payment for the first half month if the client and I realize that we are not a good fit.

Others require a whole month in advance. And some require payment for each quarter in advance to take their clients’ minds off money and onto the work they should be doing together since the fees are already paid.

Length of Engagement

Engagement lengths vary from just one quarter to years-long. There is no typical amount of time because the reasons business owners retain an FL vary so significantly.

Those who lose a full-time member of the leadership team or who are just beginning a search process may retain an FL as an interim solution during the process. Such engagements may last only three to six months and end with the successful transition to the FL’s full-time replacement.

Other business owners retain fractional talent because they need an FL’s expertise and leadership but cannot yet afford someone full-time. Engagements like this often last one to two years or longer. They end when businesses’ finances and operations start to require full-time focus and commitment. Once they’ve onboarded the right person, usually with the FL’s help, the FL can help with the transition and step out of the way.

Accountabilities and deliverables, time commitment, cost, payment terms and length of engagement form the foundation of a FL engagement. To help you further define what the best FL engagement is for your business, in Part 3 we’ll discuss a strategic vs tactical FL as well as the categories of FLs, such as organizational, Independent and Licensee Fractional leaders.

What a Fractional Leadership Engagement Looks Like



Sometimes, illustrating the concept of Fractional Leadership by way of a real-life example can help make it easier to grasp its true value. Consider the following example of one business owner’s experience to better understand what FL engagements look like.

Jack1 owns a design construction firm that focuses on medical offices, employs about 40 people, and has $14 to 16 million in annual revenue. His attention to detail and nearly obsessive commitment to quality work led him to essentially teach his sales, design, and construction teams that all decisions had to go through him. Every deal required his approval and input. He was intimately involved in design proposals and construction projects. Mistakes were unacceptable and his people did not really know how to predict what he would consider a mistake. It was his view that it was safer to run everything through him for approval.

The firm had hit a blockage. They tried to continue growing, but no matter what they did, they simply could not push past that $14 to $16 million revenue ceiling. But they could not figure out why this was happening.

Last year, Jack took his family on a resort and cruise vacation for the first time in about five years.  They had an amazing time. It was so refreshing because much of the time, particularly on the cruise, there was little or no cell phone reception, so he was able to truly enjoy the time with his family without interruption.

As a result of his time off, Jack returned to work well rested and rejuvenated. But, to his horror, Jack discovered that basically nothing had happened during his absence. Not only had his team made no sales, but they had also lost several of their prospects who needed to the work to move quickly. When the salespeople or designers could not move their projects forward, the potential customers simply went elsewhere.

This was a huge wake-up call for Jack and his team. They finally realized that because he had made himself indispensable to every single sales, design, and operational decision, he was the bottleneck creating the ceiling against which his firm was hitting its collective head. The team hadn’t built any processes or metrics to ensure that people made sales, completed designs, and constructed medical offices the right way, every time, with or without Jack’s involvement.

Inspired by the wake-up call, Jack retained a Fractional Chief Sales Officer (FCSO) to act as the company’s head of sales. The FCSO created a true sales process by clearly documenting the right and best way to do things. He also helped the sales team establish metrics so they had specific actions they knew to take every day and every week to ensure they made enough sales to achieve their goals. He helped the design team do the same thing.

Because of the systems, processes, and metrics the FCSO helped the company put into place and which he oversaw, Jack was able to start redirecting salespeople’s and designers’ inquiries to the right people. He started taking himself out of the equation so the team could sell design construction contracts without him. They started to see their revenues break through that $16 million ceiling and finally had the bandwidth to expand into other types of construction.

At this point, you understand at a high level why bringing someone onto your leadership team who’s built a business like yours before will help you. And if Jack’s situation leading up to his outsourcing a seasoned executive to bring his company’s business growth to the next level sounds at all familiar to you, it might be the right time for to consider hiring a Fractional Leader.

Learn more about each of the five types of Fractional senior executives: the Fractional Chief Marketing Officer (FCMO)Fractional Chief Sales Officer (FCSO)Fractional Chief Operating Officer (FCOO)Fractional Chief Financial Officer (FCFO) and Fractional Chief Technology Officer (FCTO)

  1. Owner’s names has been changed.


Why Fractional Leadership Works



Now that we’ve introduced each of the Fractional Leader (FL) roles with a high-level overview, what does it mean for your business to have an experienced leader swoop in when you’re stuck and guide you to your destination? A strong leader who has “been there and done that” knows what to do and how to inspire your troops to charge.

The biggest reason Fractional Leadership works is you’re bringing someone on your side who’s already gotten past the point where you’re stuck — and they’ve usually done so multiple times. They shortcut you around bottlenecks and obstacles so you can break through and go way beyond where you could on your own.

Sometimes the best way to illustrate something is to go to those who have been there done that, so I spoke with many small business owners about Fractional Leadership. Here are but a few brief examples that I discuss in length in my book.

Wil Schroter, founder and CEO of Startups.com, the world’s largest startup launch platform and cohost of the Startup Therapy Podcast, explains that in the startup world, Fractional Leadership “is just called hiring.”

There’s no way I could possibly afford the kind of Chief Operating Officer or Chief Marketing Officer (CMO) I need. I bring them on in exchange for maybe a quarter point of equity because early equity is the only kind of currency I have at that point. And the truth is that I don’t need that CMO to run my pay-per-click anyway. I can find someone on fiverr to do the grunt work. What I need is for her to tell me what’s around every corner, which company I need a partnership with, and “By the way, here are the contacts you need to talk to.” She’ll send an email that will take 15 minutes of her time and save me a year of my time. That guidance and those relationships are worth their weight in gold.

Kwame Christian, Esq., Director of the American Negotiation Institute and author of Finding Confidence in Conflict, told me that he uses a Fractional Chief Financial Officer (CFO) in his company because it allows him to bring extensive experience and an objective perspective into his business but without the full-time cost:

My Fractional CFO manages the entire financial side of our business. He has that high-level expertise, but we don’t need to pay for full-time.

His benefit is also objectivity. I think it’s easier to be more objective about the company when you have a little bit of separation. My background is in psychology, and I do some implicit bias training from time-to-time because bias is just a natural state of the human mind. I have preconceived notions about my own business. So I tell him, “Listen, I’m biased. This is the way I’m seeing it, but I’m probably missing something. What am I missing?” He can see things a lot more objectively. It’s been really helpful to have that outside influence.

The bottom line for most considering a FL is that they need a leader in the fractional role. For people who are used to having to figure everything out for themselves, hiring a Fractional Leader can almost feel like cheating. They worry they’re doing something wrong by bypassing the obstacles and skipping straight to effective (though often not easy) solutions. Although this feeling is natural, it causes them unnecessary pain and makes their progress toward their own dreams much longer and harder than it has to be.

Leader, Not Worker Bee

Tactical, frontline-type work is a distraction from a Fractional Leader’s main value proposition. Fractional Chief Sales Officers (FCSOs), for example, generally do not make their own sales. Fractional COOs do not personally lead highly technical system rollouts. And FCFOs do not personally do your bookkeeping, A/P, and payroll. Instead, FLs set up systems and processes that cause the people in your organization to do their jobs far more effectively than before. They then train and oversee those teams. This ultimately gets you far more results than one person, even one who is very skilled, can accomplish on their own. The power of FLs is their experience and ability to focus your organization’s resources on your priorities.

You probably built your business by being a “doer” who gets as much accomplished as is humanly possible. Your leadership team always did the same. The problem is, as the saying goes, “What got you here isn’t going to get you there.” Even though the “all hands on deck,” “get ’er done” culture got you past the critically dangerous startup phase, you’ve now reached the stage in your business where that does not work anymore. Isn’t that why you’re frustrated and reading about Fractional Leadership in the first place?

Get Focused on the Right Things

Whether you use an FCSO to focus your sales process and message on what resonates with your target market, an FCFO to make the right decisions based on financial experience, analysis, and data, or a Fractional Chief Technology Officer (FCTO) to build and iterate the right product, focus is key. Because FLs have seen what works and know how to drive implementation, people use them to focus their limited resources on the right things for maximum impact and scalability.

The information herein is a partial excerpt from my book, Fractional Leadership, which  is a consolidation of my personal experience as a Fractional Leader (FL), retaining other FLs in businesses I managed or manage, interviews with FLs on my podcast, Win-Win—An Entrepreneurial Community, and my network and relationships with other FLs.

My experience in operations and being a Fractional Leader in companies running on EOS certainly contribute to my knowledge of operations. I am not, however, a subject matter expert in marketing, sales, finance, or technology. I’ve written these topics with reliance on business owners and FLs in those fields — from a 30,000-foot perspective.

Check out my blogs discussing the five main types of FLs: Fractional Chief Marketing Officer (FCMO), Fractional Chief Sales Officer (FCSO), Fractional Chief Operating Officer (FCOO),  Fractional Chief Technology Officer (FCTO) and Fractional Chief Financial Officer (FCFO).

How One Entrepreneur’s Persistence and Patience Led to Success



In a recent Authority Magazine Q&A article, Fractional Leadership Founder and CEO Ben Wolf shares his story about the challenges he encountered on his way to forming his own business and why he never gave up.

Q: Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

A: I left the company where I “grew up” entrepreneurially — a healthcare startup called FreedomCare — because I realized that I like making massive change and building things and my ability to do that had plateaued. I accepted a role as COO at a smaller organization I hoped would be an even greater opportunity long-term to make a massive difference in their mission, growth, and organizational health.

While I knew about some of their major organizational challenges, I had already joined the company when I Iearned about some organizational dysfunction among the partners. This dynamic doomed me to presiding over a slow-motion train wreck I was powerless to avoid.  

I had just left a stable position and had to choose between the misery of feeling responsible to solve problems I was not permitted to even address and risking going out on my own with a wife and four children to support with no certain prospects. With my wife’s support and some savings, I had built up doing some consulting work on the side, I decided that the misery of staying where I was outweighed the risk of taking the entrepreneurial leap.  

I submitted my resignation two months after starting the new role and hung up my shingle as a Fractional Integrator, a term coined by Fractional COOs who work with companies running on the Entrepreneurial Operating System® (EOS®). I was very scared.

I began doing business development by having calls with business owners, various kinds of trusted advisors, other Fractional Leaders, and EOS Implementers®. I started a podcast called Win / Win — An Entrepreneurial Community, met with 12-18 people every week, and created measurables for myself to ensure I was doing the right kind of business development work for my new solopreneur business.

It was maddening at the beginning. Together with my beloved wife, before I was able to get any clients, it felt like that song from The Greatest Showman, “Never sure, never know how far we could fall. But it’s all an adventure. That comes with a breathtaking view. Walking a tightrope with you.”

Finally, after over three months, I got my first client. That was amazing! I helped drive massive change with that company and they grew their top-line revenue 25% the first quarter I worked with them. Things got a lot easier for me personally then, but we were still financially walking on a tightrope.

I continued hacking away at emailing, Zooming, calling, and meeting with people for another six months, always putting on a confident, non-desperate affect, when COVID-19 hit. All the business owners I was speaking with froze up, but I kept plugging away at the emails, calls, and Zoom meetings. I wondered whether I would ever feel successful. Would it ever get easier?

Then, in May 2020, the dam finally broke. As people’s paralysis broke and they realized they could no longer put their lives and businesses on hold, more and more started reaching out to me to be their Fractional Integrator. I got one client, and then another, and then another. Once I became fully booked, I began referring the leads I continued to get to other Fractional Integrators and getting invited as a speaker at various entrepreneurial groups. I began paying off my credit card and student loan debt. It was a huge relief I would never have experienced if I hadn’t kept up my weekly regimen of emails, calls, and meetings without regard to the self-doubt I felt.

Q: So, how are things going today? How did your grit and resilience lead to your eventual success? 

A: As John Astin used to say on Night Court, “I’m feeling much better now.” Because I kept going out there and helping whoever I could and connecting with more and more people, I started to develop a bit of a reputation as one of the most competent Fractional Integrators and one of the industry leaders in the Fractional Leadership community in general.

Because I continued getting so many referrals and leads for Fractional Integrator clients, I converted my “solo-preneurship” into a firm, Wolf’s Edge Consulting, with several other Fractional Integrators. I developed a proven process we took our clients through, identified what made us unique, and set up a meeting pulse through which we helped resolve each other’s challenges with clients. Now none of us are on an island, a challenge every solopreneur knows too well. 

And the people I met through my podcast, in the EOS community, and in the Fractional Leadership communities ended up making me realize that the whole Fractional Leadership world was completely fractured. There were thousands of websites by the various Fractional Leaders, both firms and solo practitioners, but there was absolutely no center of gravity in this relatively new industry. That ended up being my inspiration to write Fractional Leadership: Landing Executive Talent You Thought Was Out of Reach and creating FractionalLeadership.io as the first vetted Fractional Leader referral platform for business owners.

Read the full Authority Magazine piece, Ben Wolf of Fractional Leadership: 5 Things I Wish Someone Told Me Before I Began Leading My Company.”

3 Character Traits of Successful Business Leaders



Perhaps there are a few people who can succeed in business quickly, but I’m not one of them. It took me three months to get my first client when I went out on my own and eleven months before things really started taking off. I had self-doubt and felt discouraged, though I never showed it outwardly. If I gave up and accepted a full-time job, which several people offered me, it would have guaranteed my failure at creating two businesses and taking on a formative role in the Fractional Leadership industry.

Boy, am I glad I didn’t give up. I learned that three character traits contributed most to my business success:

  1. Disciplined persistence
  2. A help-first approach to all interactions, and
  3. Authenticity

With disciplined persistence, I created measurables for myself and set minimum numbers of email and (custom-written) LinkedIn reach-outs, calls, and presentations each week, month, and quarter. I almost never went below these quotas. These efforts in the long run have a cumulative effect. I wish there was a shortcut, but I haven’t found one that works.

Next, I recognized that nobody wants to be sold to. You have to approach every email, call, and meeting with a help-first approach. Don’t wait for people to give you a lead or make an introduction before you help them. As the saying goes, people only care how much you know after they know how much you care. Here are a few simple ways to do this:

  • In every email, share an article or resource you know from a prior conversation the person can really use or needs.
  • Take notes about the people you speak with on your calls and refer to those notes before you send an email or have your next meeting with them. Ask about their spouse, kids, hobby, or cause the next time you interact with them.
  • Refer other people to them whenever it’s helpful, even if it has nothing to do with what you do. Send them a great florist, app recommendation, favorite movie, show, or connect them with a competitor of yours if they’re a better fit for the person.

Keep this approach up and you’ll build up social capital, your reputation, and people will become more likely to think of you when they or their friends actually do need someone with your experience.

Finally, being authentic can go a long way to developing business relationships. Some people feel they succeed by ensuring that every phrase they utter, every conversation they have, and every podcast interview they do is highly engineered to make them look maximally professional, successful, smooth, and polished. I’m sure that this is one approach, but to me, such people feel fake, slick, and untrustworthy.

I’m not great at posturing and creating highly calculated interactions with people anyway, so my approach is to speak honestly. I openly mention my areas of weakness or past mistakes when it comes up in conversation because it tells people that I am what they see. They don’t have to wonder what I’m concealing because they see I’m not trying to carefully maintain the perfect veneer.

By being authentic with people, they respect and trust me more because they’re not wondering who or what I really am and don’t feel like I’m trying to sell them something if it’s not right for them.

If you’re thinking of starting a business, knowing the positive impact these three traits ahead of time can help give you peace of mind and confidence from the start. (For other insights I believe help makes a successful business and leaders in my blog “The Most Underestimated Aspect of a Successful Company.”)

Perfection Can Hold You Back

As a business owner, insisting on perfection 100 percent of the time won’t get you results. In my experience as a Fractional Leader, the most common mistake I see an entrepreneur or organization’s leadership commit is waiting until everything is “perfect” before launching a new business, product, service, or system.

The Pareto Principle, also called the “80% Rule,” states that most of the time, you get 80 percent of your results from 20 percent of your effort. After your first main push toward creating your new business or product, you’ll find yourself 80 percent of the way toward completion. You then spend 80% of your effort on the remaining 20 percent of the results you need. And your efforts get less and less productive the further into the remaining 20 percent you get. Your efforts have an exponentially diminishing rate of return.

Get yourself most of the way there toward your minimum viable product (MVP), and then just launch it. You’d continue improving and iterating after release anyway, and your efforts at building “perfection” before testing your product or service against the reality of the real world are almost certainly not “perfect” anyway.

Most of the time, the right path is “launch and learn.”

If you can model your business approach around being persistent, helping first and being authentic while at the same time not letting a mindset that seeks perfection slow your progress down, you’re well on the road to success.

The blog is comprised of modified excerpts from Authority Magazine‘s December 2021 article, “Ben Wolf of Fractional Leadership: 5 Things I Wish Someone Told Me Before I Began Leading My Company

The Most Underestimated Aspect of a Successful Company




This might surprise you if you’re not a business owner. But if you’re a successful business owner, you’ll know what I’m talking about. Read on: The most underestimated aspect of running a company is being disciplined about only bringing people on your team who naturally share your core values. This means that their work style must be compatible with yours.

Many people tend to focus only on finding people who have the right skills, experience, or resume so you know they can effectively do the job you’re hiring them to do. That is, of course, important also. We cannot hire people who cannot effectively and consistently perform excellently at the jobs you hired them to do. But most of my clients’ issues with their people have to do with the fact that they don’t share the founder’s and leadership team’s core values.

I had one client, the founder and CEO of a construction company, who identified taking ownership as one of his company’s core values. But when I started working with them, most of the people in the company tended to check off their daily checklists without taking ownership over ensuring the success of their parts of the business. Whenever he needed them to do anything or implement an improvement we were working on, the founder felt like he had to pull, push, and drag them along. It was draining and exhausting.

Dan Sullivan from Strategic Coach talks about how the number one thing you need in team members is that they come with “batteries included.” They join the team already equipped with their energy, motivation, ideas, and commitment. They don’t drain your energy. Working with them gives you energy.

Because my construction client continued pushing for excellence and growth and didn’t let his team members’ negativity and lethargy stop him from pursuing what he wanted to see from his business, all of those energy-draining people felt more and more friction as they tried to maintain the status quo of their roles. Fighting change and resisting ownership over their results became more and more taxing and unpleasant until they all eventually left on their own. With a number of right-people hires, he now has a team full of people who came with batteries included.

It is possible to have people who fit your core values. You don’t have to resign yourself to having a team full of people who don’t. And anyway, the people you have to let go or leave will be happier and feel more successful in other organizations where they do match the core values.

But There’s More: What I Wish I had Known Before Starting My Business

Of course, having team members who naturally hold your core values is what I consider to be the most underestimated quality of successful business, but before you even hire your team, consider these five things that I believe every entrepreneur should hold in good stead before even stepping into the leadership role. I’ll cover them briefly here.

Have disciplined persistence. You win by staying in the game longer than anyone else. Identify the types of actions that get results and then set measurables to ensure you or your team take a minimum number of those actions every week, month, or quarter. Then later, rinse, and repeat. One of the clients knew that for every 100 target market prospects their salespeople emailed, they got five pitch calls and converted about 40% of those into clients. That’s two clients for every 100 emails. It’s not rocket science, but if you take the right actions consistently over a long period of time, you’ll ultimately see cumulative results you can’t imagine right now.

Help first. Don’t wait until people give you leads before you give them something. Help people out before they do anything for you. When you make this a habit, people don’t resist setting up conversations with you because they see from experience that you want to help them without asking for anything in return. I created and still maintain a weekly metric to track the number of referrals I make to others. It keeps me focused on helping others. It ultimately comes back to you anyway because people remember you as a good person who wants to help others and not just a selfish salesperson.

Be authentic. Don’t try to hide the things you don’t know or pretend like you never made a mistake. It comes across as fake, overly slick, and sales-y. In my Win Win podcast, I ask my guests the questions I feel skeptics about their industry or product would ask. It makes the conversation more authentic and helps them by giving them the chance to address the audience’s implicit questions preemptively. They build more authority and trust that way.

Launch and learn. Things will never be perfect before launching them, and you’re likely to be even further from perfection if you delay testing what you’ve built against the reality of actual use. When I launched fractionalleadership.io as a vetted Fractional Leader referral platform, I immediately set it up using Google forms, Google Docs, Google Sheets, etc. I didn’t want to waste time and tens of thousands of dollars it would have taken to create that automation without even testing which processes worked in real life with actual business owners and Fractional Leaders. Get your MVP (minimum viable product) and launch and learn!

Start with a process. When you start building your business, you’ll be tempted to do things in a way that works at the small scale you have at the beginning. Wherever practical, document your processes and make them scalable. Imagine if you went on vacation on a cruise ship for a week without any access to Wi-Fi or cell phone service. Can the systems and teams you put into place keep your business running without you? For example, instead of your team having to get pricing from you for each pitch or proposal, set up a rubric they can use on their own to do the pricing and pitch without you.

The blog is comprised of modified excerpts from Authority Magazine‘s December 2021 article, “Ben Wolf of Fractional Leadership: 5 Things I Wish Someone Told Me Before I Began Leading My Company.”

Fractional Leadership and the Fractional CTO and CIO

image-photo/big-data-visualization-network-connection-structure-1646128768 copy

image-photo/big-data-visualization-network-connection-structure-1646128768 copy


If your greatest need or what’s keeping you up at night relates to the proprietary tech products or systems you built and that you sell to your customers, or if you need your out-of-the-box systems up and running every second for your business to run, you may need a Fractional Chief Technology Officer or Fractional Chief Information Officer.

Let’s paint a picture of what that looks like.

You or a member of your leadership team are doing your best to manage a patchwork of freelancers, an Managed Services Provider (MSP), a VoIP provider, and internal or external developers or resources. Still, you don’t have the time, experience, or resources to do this well. It’s taking a toll on your ability to do what you need in other parts of the business. It’s holding you back.

Alternatively, you built a product using freelancers, and you sell usage of that product to your customers. But you’ve now grown the business big enough that the product and your customers’ needs are outgrowing your ability to serve them effectively. You’re one outage or bug away from disaster.

Another scenario is that you need to do a technology-heavy rehaul or turnaround of your operations, but you’re not sure where to start and certainly don’t have the bandwidth to drive and oversee

Do You Need an FCTO, FCIO or Consultant?

So, which role would best serve your business do you need, a Fractional CIO or CTO, or a consultant? Let’s run down the basics for each position.

The Fractional Chief Technology Officer

If you developed your proprietary technology and have an internal or external development team maintaining it, you may need a full-time CTO or a Fractional CTO. Without the right person focused on your product and the systems on which it operates, your entire business sits on very shaky ground.

You need someone who understands the servers on which those systems run, whether server-based or cloud-based. Your critical risks include data security, server reliability and speed, redundancy if something goes wrong, external and internal tampering, and hacking. You likely need someone with experience to take ownership of your technology.

The Fractional Chief Information Officer

Even if you utilize others’ technology, CRM, or ERP, if you’re over 1,000 people or have very complex, customized, or temperamental systems you desperately rely on every second, you may need an FCIO to allow you to sleep at night. You’ll also free yourself up to focus on running and growing your business once your technology isn’t hogging a huge share of your mental and emotional bandwidth.

Technology and Process Consultants

When do you need a technology or process consultant? In short, these professionals are most helpful when your need is more transactional or short-term. Suppose you need to choose and customize a technology once. In that case, a consultant can help you map out your business processes, research and choose the right technology solution for you to buy, and then hand off oversight of the actual implementation to someone internally.

Many technology and process consultants also offer implementation services. This still falls under the transactional or short-term umbrella. They’ll oversee the selection, execution, data migration, and rollout of the selected technology so that you don’t have to. But after that, their work is done.

Suppose you have significant ongoing needs that require strategic, ongoing leadership to oversee or continue improving and iterating the technologies on which you rely. In that case, you should consider retaining an FCIO or FCTO.

What Does the FCTO or FCIO Engagement Look Like?

The order of operations at the beginning of an FCTO or FCIO engagement depends heavily on why the business brings them in. Things look different if they’re there to implement a herculean technology overhaul or significantly level up and then shepherd ongoing operations. But first, they’ll lay some groundwork:

  • They’ll likely start off getting a lay of the land by getting to know you and the internal or external technology people you already have in place and exploring the systems you already have.
  • They will work with you and your team members to understand your business model and legal or regulatory framework.
  • Finally, they will learn from you about your long-term plans, vision, and goals.

This groundwork is critical for an FCTO or FCIO to ensure that your technology serves you not only in the short term but so that they have the information necessary to create a roadmap for the future to ensure that your systems continue to align with and support the achievement of your goals and don’t become an obstacle or liability later on.

Once they have the lay of the land and understand your ultimate destination, your FCIO or FCTO will prioritize the next steps necessary to align your systems with your current and, ultimately, future business.

On an ongoing basis, an FCIO or FCTO is your partner and continual resource in driving, overseeing, adapting, and iterating your technology infrastructure or products so that you can sleep at night and focus on growing the other parts of your business. You can rest assured that someone who knows exactly what they’re doing is taking care of the technology side of things.

Critically, this technology leader is a strategic partner and participates with your leadership team in their regular meetings and discussions. Ongoing operations, issue solving, budget, and plans all touch your tech in some way. You want your FCIO or FCTO to hear and be aligned with the other parts of your organization. The rest of the team needs your technology leader’s input regarding day-to-day operations, financial decision-making, and planning for the future.

What to Ask When Hiring an FCTO or FCIO

Once you’ve decided to move forward and hire a Fractional CIO or Fractional CTO, Consider the following when interviewing potential candidates:

  • Ensure that you and your potential FCIO or FCTO speak the same language, literally. The terms CIO, CTO, Head of Product, Product Manager, and Chief Information and Security Officer (CISO) all mean different things, and not everyone defines them the same way. Confirm that you’re both talking about the same things when using these terms.
  • As always, communicate exactly what you want the engagement to achieve and in what time frame.
  • Ensure that they have relevant, demonstrated experience doing something similar to what you need. This particularly applies if your potential FCIO or FCTO has a daunting technology goal like overseeing a new system rollout and data migration or directing the development of a product for sale to your customers.
  • Ensure they have industry experience if that is important to you. Examples include when your industry has an unusually specialized business model, complicated regulations that affect technology (like hospital systems or Department of Defense security requirements), or standards that would make the learning curve of someone without that industry experience unwieldy.

Virtually every business, and certainly one in growth mode, requires technology, including hardware, networking, security, internet, VoIP, and various Customer Relationship Management (CRM) software or Enterprise Resource Planning (ERP) systems to run the day-to-day business. If your business is struggling in any of these areas, a Fractional CTO or CIO might be the answer.

This blog is the last in a series that outlines some high-level considerations and offers insight into the five major types of Fractional Leadership: marketing, sales, operations, finance, and technology.

The information is a consolidation of my personal experience as a Fractional Leader (FL), retaining other FLs in businesses I managed or manage, interviews with FLs on my podcast, Win-Win—An Entrepreneurial Community, and my network and relationships with other FLs.

My experience in operations and being a Fractional Leader in companies running on EOS certainly contribute to my knowledge of operations. I am not, however, a subject matter expert in marketing, sales, finance, or technology. I’ve written these topics with reliance on business owners and FLs in those fields — from a 30,000-foot perspective.

Check out my blogs discussing the Fractional Chief Marketing Officer (FCMO), Fractional Chief Sales Officer (FCSO), Fractional Chief Operating Officer (FCOO) and Fractional Chief Financial Officer (FCFO).

Fractional Leadership and the Fractional CFO

image-photo/businesswoman-drawing-strategy-plan-over-ladder 1200

image-photo/businesswoman-drawing-strategy-plan-over-ladder 1200


Is your company suffering from lack of a clear financial strategy or your revenue isn’t where you want it to be despite having strong marketing and sales and operations leadership?  It might be time to consider a Fractional Chief Financial Officer (FCFO).

Generally, there are two main scenarios that could cause you to consider engaging the help of an FCFO.

The first is simply that the person who grew up with the company handling finance is somewhat out of their element at your current scale.  Your head of finance is someone who’s not a professional CFO with experience advising and analyzing the needs and unique decision points of a multimillion-dollar venture. They may have learned finance through taking courses, bookkeeping training, YouTube videos, or perhaps they’re a certified public accountant (CPA) or have experience as a controller.

The second scenario is that you’re facing a specific finance-related crisis, challenge, or transaction, such as facing a cash crunch, experiencing low or negative profit margin, suffering from high expenses, outgrowing your finance systems, navigating an audit, raising capital, or preparing for a sale or acquisition.

In either case, your revenue might be between $2 million and $50 million and you recognize that your leadership team lacks the financial experience and expertise you need at this stage.

Do You Need an Accountant or FCFO?

It’s sometimes unclear to small business owners when they need CPA or a Fractional CFO. The first thing to do before moving forward to improve your finance team is to be clear about whether it’s tax and financial advice your business needs or execution of an internal financial overhaul or strategy under experienced leadership to help your company earn or increase its profits.

If the former, an accountant is your best bet. If the latter, it’s an FCFO.

What Does FCFO Engagement Look Like?

Depending on the mandate you agree upon, the Fractional CFO will likely oversee all finance operations, including your bookkeeping, accounting, insurance, banking, tax, and legal functions to ensure that you’re managing your risk and that you’re covered from all angles.  However, they’re leadership role is often required to go deeper:

  • They will ensure that the appropriate financial staff and technology systems are In place and integrated with marketing, sales, and operations.
  • They will overseeing financial reporting, so you and the other members of the leadership team have the data you need to make great decisions. This includes the all-important budgeting process. Approximately 50 percent of businesses close within their first five years of existence. You don’t want to become one of those because you spent more than you could afford, ran out of cash, and couldn’t make payroll.
  • Once your organization is healthier and has the tools and practices it needs to scale successfully, they will stay with you until you’re ready for them to help level up someone internally to take on the CFO or Head of Finance role or to help you hire a full-time CFO.

What to Ask When Hiring a FCFO

As with any Fractional Leader (FL), it’s critical that you communicate your desired outcomes and deliverables when hiring an FCFO. By doing so, you can ensure that you both are on the same page. Consider the following when interviewing candidates:

  • If you’re retaining an FCFO because of a specific transactional need or type of crisis like an M&A transaction, due diligence, bankruptcy, restructuring, or cash crisis, you definitely want to ensure they have proven experience with that kind of scenario.
  • Ensure they have full-time CFO experience before they “went fractional.” Like other kinds of FLs, people must have first gone through the gauntlet of deep CFO service with an organization to earn the chops necessary to spot issues quickly and find solutions in a fractional scenario.
  • If the learning curve for your business model is great, ensure that they have industry experience. For example, if you have a home care business that bills Medicaid payors and you need someone who understands that industry so they’re not starting from scratch, make sure that background is there before either of you waste your time.

Like other Fractional leaders, most FCFOs do not want to permanently embed themselves into your organization. They want to get your ducks in a row, financially speaking, so your business can become healthier, and you can thrive and focus on what your business really does for its customers or clients.

This blog is part of a series that outlines some high-level considerations and offers insight into the five major types of Fractional Leadership: marketing, sales, operations, finance, and technology.

The information is a consolidation of my personal experience as a Fractional Leader (FL), retaining other FLs in businesses I managed or manage, interviews with FLs on my podcast, Win-Win—An Entrepreneurial Community, and my network and relationships with other FLs.

My experience in operations and being a Fractional Leader in companies running on EOS certainly contribute to my knowledge of operations. I am not, however, a subject matter expert in marketing, sales, finance, or technology. I’ve written these topics with reliance on business owners and FLs in those fields — from a 30,000-foot perspective.

If your company’s marketing or sales efforts aren’t generating the level of performance you need, check out my blogs discussing the Fractional Chief Marketing Officer (FCMO), Fractional Chief Sales Officer (FCSO) and Fractional Chief Operating Officer (FCOO).

Fractional Leadership and the Fractional COO




As a small business owner, are you at the stage in your company’s growth where you’re experiencing poor cash flow, stagnant business growth, increasing overhead, or low or dipping conversion rates? Perhaps your operations can’t keep pace with your sales revenue or are slow or mistake-ridden. You’ve tried several solutions, but nothing has worked, and you’re not sure what to do about it.

At this stage in your entrepreneurial journey, your company has likely grown big enough that you can no longer afford to continue without senior executive leadership of your operations, and you don’t have the time to fill in. The challenge is that you’re not yet big enough to afford a chief operating officer (COO) with the kind of experience you desperately need on a full-time basis.

Or, in some instances, people are ready to hire (or replace) a COO full-time but know that the selection of the right person is so critical that they don’t want to rush it and are willing to spend the six to 18 months it might take to find the right person. They engage with a fractional chief operating officer (FCOO) on an interim basis because they cannot afford to leave that seat unfilled and lose precious momentum during the search process.

How Does an FCOO Engagement Work?

If you’ve decided that hiring a Fractional COO is the next step for your business, begin with the end in mind. This is the typical mantra of FCOOs. At the beginning of an engagement, they will work with you to learn about your business and determine where you are now and where you want to go.

Once you’ve determined that, they will work with you to map out a plan for getting you from point A to point Z. Depending on the critical issues weighing you down or causing you the most pain, they may tackle people issues, process issues or data issues first.

If successful, your Fractional Leader (FL) will help you grow and scale in a way you could never do on your own. They will ultimately help you interview full-time COO candidates, collaborate with you in the hiring process, and then transition a new COO into the position. Alternatively, using your new structure and processes, you may be able to transition the head of operations role to someone internally. The FCOO can help you train and mentor that person to level them up into the role.

The next step is to decide what type of FCOO is best suited for your business.

What Type of Leader Do You Need?

In terms of size and scale, I’ve seen two major types of businesses engaging the help of a Fractional Chief Operating Officer — small and midsize businesses. There are Doer Leader and Manager Leader FCOOs custom-made for each.

The Doer Leader

If you’re a small business, you probably have five to 20 employees and one person, or maybe no one besides yourself, on your leadership team. You need help with organizational structure, processes, and better data, but you also need someone to get higher-level stuff done. I call the kind of FCOO you need a Doer Leader.

FCOOs of this type typically come at a lower price point relative to Manager Leaders. Business owners often engage them for one day per week or more. Because, in addition to their leadership role, they’re also doing more tactical operations leadership or getting multiple cross-functional projects done, they may work two or two and a half days per week.

The Manager Leader

If you’re a mid-sized business, you probably have 20 to 250 employees and have a leadership team of two or more people. Your primary need is the leadership of someone who’s already built a business as big or bigger than yours and can put into place the structure, data, management systems, and processes your business needs to get to the next level. I call this kind of person a Manager Leader.

This type of Fractional COO typically has experience with larger organizations and engages with their clients at a higher level to determine the proper structure for an organization, define its goals, establish the right metrics to ensure it achieves those goals, and then drive implementation of those goals at the leadership team level.

These FCOOs typically, though not always, work for about one day per week or less. They frequently come at a higher price point relative to Manager Leader FCOOs for the same time commitment because of the more strategic nature of their leadership and their experience running larger organizations.

What to Ask When Hiring an FCOO

As with any FL, it’s critical that you communicate your desired outcomes and deliverables. By doing so, you can ensure that you’re on the same page with your potential FCOO. Consider the following when interviewing candidates:

  • If industry experience is essential and you believe the learning curve is too great and would take too long, ensure that the FCOO candidate has the industry experience you need.
  • If you need help on a specific kind of activity or transaction, whether that’s an M&A transaction, a due diligence process, a new product rollout, or a new system rollout, make sure you’re satisfied the FCOO candidate has experience with these types of operations.
  • Be clear about whether you need or expect them to physically work in your office, whether the engagement will be fully remote, or some combination.

Although each Fractional COO engagement looks different depending on the industry, your style and values, and the organization’s size, they result in improved team health, standardized better processes, real traction toward goals, and less stress. It also means that as a business owner, you can finally regain the feeling of satisfaction and enjoyment from the businesses you founded.

This blog is part of a series that outlines some high-level considerations and offers insight into the five major types of Fractional Leadership: marketing, sales, operations, finance, and technology.

The information is a consolidation of my personal experience as a Fractional Leader (FL), retaining other FLs in businesses I managed or manage, interviews with FLs on my podcast, Win-Win—An Entrepreneurial Community, and my network and relationships with other FLs.

My experience in operations and being a Fractional Leader in companies running on EOS certainly contribute to my knowledge of operations. I am not, however, a subject matter expert in marketing, sales, finance, or technology. I’ve written these topics with reliance on business owners and FLs in those fields — from a 30,000-foot perspective.

If your company’s marketing or sales efforts aren’t generating the level of performance you need, check out my blogs discussing the Fractional Chief Marketing Officer (FCMO) and Fractional Chief Sales Officer (CSO).

Fractional Leadership and the Fractional CSO




This blog is part of a series that outlines some high-level considerations and offers insight into the five major types of Fractional Leadership: marketing, sales, operations, finance, and technology.

The information is a consolidation of my personal experience as a Fractional Leader (FL), retaining other FLs in businesses I managed or manage, interviews with FLs on my podcast, Win-Win—An Entrepreneurial Community, and my network and relationships with other FLs.

My experience in operations and being a Fractional Leader in companies running on EOS certainly contribute to my knowledge of operations. I am not, however, a subject matter expert in marketing, sales, finance, or technology. I’ve written these topics with reliance on business owners and FLs in those fields — from a 30,000-foot perspective.

Check out my previous blog discussing the Fractional Chief Marketing Officer (FCMO).

If your marketing is in good (or good enough) shape, what about your sales team? To ensure your sales team capitalizes on the demand created by your marketing, it might be time for you to consider engaging a Fractional Chief Sales Officer (FCSO) to help dial in a high-performance team.

Does Your Sales Strategy Needs Help?

Let’s briefly discuss the several scenarios that trigger the need for an FCSO ( In my book Fractional Leadership, I detail these scenarios as described by Teresa Renaud, an FCSO affiliated with SalesQB.

Scenario 1: you’re personally “half-managing” the sales team. You don’t have a Head of Sales you can trust or rely on, or, because you’re the best at sales, so you’re running the team. I say “half-managing” because you have an entire business to run, not just sales, so your full attention isn’t on it. You don’t have the bandwidth to develop a proven sales process, figure out how to collect and use data to hold the team accountable for actual sales results, and you don’t have the time to teach, manage, and coach the sales team to excellence the way they need. You’re frustrated with the results.

Scenario 2: You hired a sales leader or manager at a lower price point because you can’t afford more or don’t see sales management as hard. You underestimated the skills and experience you need your sales leader to have. Now you have an underperforming sales manager who’s frustrating you and the team. All the salespeople still go to you almost all of the time anyway, they’re frustrated, and the sales manager is one more person you have to manage. He isn’t saving you any time.

Scenario 3: You decided to take your best salesperson and make them the sales manager or team leader. They either take a passive role, simply answering other salespeople’s questions, leaving them with essentially no manager at all. Or they try to live up to that role but aren’t good at managing people, creating systems and processes, collecting data, or using that data to hold the team accountable. You’ve now lost your best salesperson, so sales are down, and you still don’t have an effective sales leader for everyone else. It’s the worst of both worlds.

The common denominator in all of these scenarios is recognizing that being a good salesperson is an entirely different skillset from leadership, management of people, and the creation of accountability.

To get past this blockage, you want someone who’s built and led sales teams successfully before. The catch is you think you can’t afford someone with that level of experience full-time.

How Does an FCSO Engagement Work?

A Fractional CSO might be what you need, but how does it work?

Again, I go into more detail in my book, but briefly, depending on the situation in your business, your FCSO will tackle the various elements of a powerful sales team in different orders. These can include:

  • Locking down your lead generation process and head up your marketing efforts.
  • Ensuring that whatever you’re doing for lead generation gets you leads in your target market and that you have the correct information for them.
  • Creating a scoring system to ensure accountability for the quality and the number of leads.
  • Drawing on your and your sales team’s experience to clarify and document the right and best way to make sales in your unique organization with your unique customer or client base.
  • Determining how best to use technology like a CRM to manage these metrics and create actionable data. Using this data, you’ll find out how many of each type of action you need to get the results you want.
  • Taking ownership over building up your sales team when appropriate by driving recruiting, interviewing, hiring, and training to build a team of “A” players.
  • Creating corrective action plans with underperforming salespeople and make the difficult decision to let someone go when it becomes apparent that they aren’t going to be able to level up.

This all sounds great. So, what is the next step?

What Type of FCSO Do You Need?

Now it’s time to determine which type of FSCO is best for your business.

Some FCSOs operate as a group under one umbrella — which I call organizational Fractional Leaders (OFLs). You engage with an FCSO firm, and they work with you to find you an experienced FCSO from their firm to serve on your leadership team.

Other business owners engage with solo practitioners or individual, “single shingle” FCSOs. They like the independence and greater simplicity of working with a single individual. If that person has the right experience, this often works very well.

Some independent FCSOs are licensees of an established sales management system. The two main licensing organizations are SalesQB and Sales Xceleration.

Great FCSOs are using all the above models, so you need to ask yourself which resonates more with you. It can be helpful to speak with FCSOs or clients who have used the various models to determine which would be best for you.

Define Deliverables When Hiring an FCSO

If you’ve decided to hire an FCSO, be sure you’ve define the deliverables you expect from your fractional hire before the engagement starts. This includes:

  • Discussing your current sales and what you expect them to achieve, and in what time frame;
  • Discussing the level of authority you can and are willing to grant the FCSO; and
  • Ensuring that the two of you are 100 percent on the same page to avoid misunderstanding, frustration, or disappointment later on.

If your company’s marketing or sales are not your biggest pain points right now, but you’re having pervasive issues with your people, business structure, or processes, your main pain point might be your operations. In my next blog, I’ll discuss how engaging a Fractional Chief Operating Officer (FCOO) or, for companies using the Entrepreneurial Operating System management (EOS) framework, Fractional Integrator, can tighten up your business operations.