Ben Wolf Of Fractional Leadership

    We Spoke to Ben Wolf Of Fractional Leadership on Being an Effective Leader During Turbulent Times

    As part of our series about the “5 Things I Wish Someone Told Me Before I Began Leading My Company,” we had the pleasure of interviewing Ernie Villany.

    Ben Wolf is a bestselling author and founder and CEO of, the first platform dedicated to referring vetted fractional leaders to small and midsize business owners and leaders.

    Ben recognized the value of fractional leadership while building operations at a healthcare startup from pre-launch into the largest organization of its type in New York State. Today, he operates Wolf’s Edge Consulting, a Fractional Integrator firm for small and midsize businesses, and hosts the podcast Win Win — An Entrepreneurial Community. He lives with his wife and four children in Long.

    Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

    Happy to be here! I grew up in Nashville, TN, went to college in New York City, and stayed in New York when I met my wife in college and we got married a couple of months before graduation. Fast-forward a couple of lifetimes and I joined a healthcare startup called FreedomCare after practicing corporate restructuring and bankruptcy law at one of New York City’s top law firms. Because you have to wear “all the hats” in the startup world, I learned a huge amount building most of the operations at that company, which became the largest organization of its type in New York State in less than three years and numbered over 130 people by the time I left.

    When I went on my own, I hung up my shingle as a Fractional Integrator (outsourced COO). After building up that practice, I ultimately turned it into a Fractional Integrator firm made up of several great Fractional Integrators, and met many other fractional executives through my podcast, Win Win — An Entrepreneurial Community and the constellation of people I connected with in the Entrepreneurial Operating System® (EOS®) world.

    I realized that while there are thousands of solo practitioner and firm websites explaining what fractional executive leadership is, there was simply no comprehensive guide for business owners about what Fractional Leadership® is, what it does for businesses, how it works, whether it is for them or not, and how to find a right-fit Fractional Leader®.

    I wrote Fractional Leadership: Landing Executive Talent You Thought Was Out of Reach to fill that need and created as the first vetted Fractional Leader referral platform to make it easier for business owners to find right-fit Fractional Leaders.

    I now live in Long Island, New York with my wife and our four wonderful children.

    What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

    As a member of various leadership teams trying to find the right Fractional Leader for several searches and as a Fractional Leader myself meeting with potential clients, I was struck by how manual, slow, and disorganized the process was for both sides. You have to kiss so many frogs. You often don’t have any clear way of finding out whether someone has the right industry experience, what they charge, or whether they’ve worked with companies like yours before until you get on a phone call or Zoom meeting with them. You also don’t know if they’re the real deal or not if you don’t know someone who’s successfully used them before. The whole thing is hugely inefficient.

    That’s when I wrote the book, Fractional Leadership: Landing Executive Talent You Thought Was Out of Reach. Before, there was no comprehensive guide for business owners on what Fractional Leadership even is, what it could do for your business, whether it’s right for you at all, how it works, and how to find a Fractional Leader if you conclude that’s the right path.

    And to relieve the time sucking process of finding the right Fractional Leader, I created as the first platform for finding your right-fit, vetted Fractional Leader. I set up a team and process where we don’t add Fractional Leaders to our network until we have done screening interviews with them, profiled them for the attributes business owners care about, and independently gotten a reference about them from three of their actual clients. We then refer them to business owners looking for fractional executives in marketing, sales, operations, finance, and technology,

    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?

    I left the company where I “grew up” entrepreneurially 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 Learned 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.

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

    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 solopreneurship 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 others’ 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 as the first vetted Fractional Leader referral platform for business owners.

    What do you think makes your company stand out? Can you share a story?

    Imagine ZocDoc for patients and the AMA for doctors all rolled into one.

    I wanted to make the easiest possible way for business owners who know they want to retain a Fractional Leader to find the right person, with the background and experience they need and rates they can afford, with the confidence that they’re the real deal because they know we’ve heard directly from their clients.

    I also wanted to make Fractional Leadership a community for everyone in this newly exploding fractional executive industry to connect with each other, access peer-advisory groups with others who understand what they do and their unique challenges, and access all kinds of professional development opportunities so they can “sharpen the saw.”

    Shortly after launching, we got a request from Rachel Beider, founder of a clinical massage practice with several locations in Brooklyn, NY, PRESS Modern Massage. She needed a CFO but knew she could not afford to hire a full-time CFO who had the kind of experience she needed, nor would full-time have made sense at her size and scale even if it were affordable. Rachel’s story is not dramatic. She filled out the request form on our website, we sent her vetted referrals within two business days and she retained one of them soon afterward.

    Another business owner, the founder and CEO of a 20-person, Maryland-based, financial planning and wealth management firm, used to request a Fractional Integrator (COO). Again, within two days, we gave her three vetted Fractional Integrators who had availability, were within her budget, and had the industry experience she needed. She retained one of them and he has already joined their leadership team and is driving massive change and growth.

    Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

    The big law firms are known as being pretty intense places. Before I went into the entrepreneurial world, I was a corporate restructuring and bankruptcy associate at one of the big New York City law firms. To fight the loneliness everyone experienced working all hours of the day and night in our offices, the associates often just sat on the phone with each other for hours on end, quietly working or making random comments to each other from time to time.

    A few weeks after I got there, it was about 10:30 at night and I was assigned to a certain case with a senior associate. We were just quietly sitting on the phone while we worked. He asked me, “So, are you planning to stay late tonight?” I was confused, not understanding what he meant since it was already pretty late. I paused for a few seconds, assuming he was making a self-deprecating joke. After a long, somewhat awkward, pause, when I realized he was not being ironic, I answered that no, I was probably not leaving early that night. Ending at 10:30 actually was considered an early night. What had I gotten myself into?!

    I of course knew that it was going to be intense. But the takeaway, if any, from the story is to always ensure that your expectations are aligned with the reality.

    Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

    Yeah, one of the people I had some networking calls with swore that sheer volume of LinkedIn reach-outs was the key to successful business development. He assured me that even if even a small portion of them lead to a call, and only a portion of those converted into clients, it was still quite worth it.

    I didn’t want to dismiss the idea without giving it a shot so I retained an assistant in the Philippines, set up a process between the two of us to send people with a specific profile a four-week, relatively customized, sequence of messages. I put many hours every week and a few dollars into this project for two or three months before finally accepting that it was a waste of time and just annoyed people.

    I should have listened to my own experience and brushed off the suggestion since I always ignore these messages when people send them to me unless they are extremely customized and the writer obviously wrote to me specifically. And the one who gave me that advice gave up his consulting practice and took a full time job. But now I know from personal experience that mass LinkedIn reach-outs are a waste of time and energy, and only cheapen your image in others’ eyes.

    You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

    The three character traits I think contributed most to my success are (1) disciplined persistence, (2) a help-first approach to all interactions, and (3) authenticity.

    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. The difference was 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 the quotas I set for myself and those things have a cumulative effect. I wish there was a shortcut, but I haven’t found one that works.

    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. 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 friend actually do need what you do.

    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.

    Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

    The best way to avoid “burnout” is learning to say no. Greg McKeown quotes the German designer Dieter Rams in his book Essentialism: The Disciplined Pursuit of Less as always saying, “Weniger aber besser — Do less better.”

    Fractional Leaders burn out when they take on too many clients. Sometimes they do this because they have a scarcity mindset. They remember not having enough clients in the past, so they take on too many clients, like squirrels, mice, or beavers stocking up on food for the winter. Others do it because they don’t value their own services highly enough and undercharge. They are therefore forced to take on too many clients because they won’t make enough money otherwise. I believe this also comes from a scarcity mindset.

    People should look at what great Fractional Leaders like them are charging their clients to understand their market better. They should consider charging more so they can ensure that they’re giving the best results and maximum value to a smaller number of clients. They should set a cap on the number of clients they will work with or the number of “billable hours” per week they will do. This will allow them to build in a buffer time for business development work, pitch meetings, networking, and handling the little fires that come up. I know one Fractional CFO who regularly pulls all-nighters doing client work. That is not smart or sustainable! Those who don’t build in buffer time not only feel burned out, but they do not serve their clients as well because they have no flex time in which to help out when their clients need more help than usual.

    What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

    The most common mistake 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% of your results from 20% of your effort. After your first main push toward creating your new business or product, you’ll find yourself 80% of the way toward completion. You then spend 80% of your effort on the remaining 20% of the results you need. And your efforts get less and less productive the further into the remaining 20% you get. Your efforts have an exponentially diminishing rate of return.

    Get yourself most of the way there toward your MVP (minimum viable product), 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.”

    In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

    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 workstyle 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 they were hired 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 just want 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 to 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 own 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 who you have to let go or who leave will be happier and feel more successful in other organizations where they do match the core values.

    Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

    1. Have disciplined persistence. You win by staying in the game longer than anyone else. Identify the types of actions which get results and then set measurables to ensure you or your team are taking a minimum number of those actions every week, month, or quarter. Then later, rinse, and repeat. One of 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 2 clients for every 100 emails. They therefore worked backward, based on their top-line sales goals, to determine how many email reach-outs and pitch calls they needed to see from each team member every week. Their head of sales then set up a tracking process in their CRM together with weekly meetings to create accountability and help troubleshoot when people missed their numbers. 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.
    2. 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. Get in the habit of listening for problems or potential needs and see how you can help with an introduction, recommendation, article, word of advice based on your experience, or even a kind word that shows them you remember the things that are important to them, and don’t just see them as a prospect to be worked. I created and still maintain a weekly metric for myself 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.
    3. 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 like skeptics about their industry or product would ask because I feel it makes the conversation more authentic and helps them by giving them the chance to preemptively address the audience’s implicit questions. They build more authority and trust that way. I had one potential guest who insisted on controlling his every exposure and appearing perfectly scripted. He wasn’t a good fit for my show because I believe you build your brand and authority by showing up for readers, listeners, and viewers as authentic and real, not perfectly postured and coiffured.
    4. Launch and learn. Things will never be perfect before launching them, and you’re likely to be ever further from perfection if you delay testing what you’ve built against the reality of actual use. When I launched as a vetted Fractional Leder referral platform, I set it up using Google forms, documented processes on Google Docs, Google Sheets, Gmail, and a matchmaking team of awesome part-timers I put together. I could have automated 90% of what we do (and I plan to), but I didn’t want to waste the 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 just launch and learn!
    5. Start with 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, before setting up how anything works, make it documented and scalable. Imagine if you went on vacation on a cruise ship for a week without any access to wifi or cell phone service. Can the systems and teams you set up keep your business running without you? 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. Even though it’s more work up front to set up a process rather than allow people to ask you questions every time, it will cost you far more time in the long run and it will make you the bottleneck, stifling your own organization’s growth. Build things out with a scalable process from the get-go wherever possible.

    You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

    I want Fractional Leadership to create a revolution in the small and mid-size business world. People use Fractional Leaders when they can’t scale without an experienced, been-there-done-that executive in marketing, sales, operations, finance, or technology, but can’t afford someone like that until after they’ve scaled. I call this the “Entrepreneurial Catch-22.”

    If we assume that the average business has a gross revenue of $10 million and we can match 1,000 business owners with right-fit Fractional Leaders, and if the Fractional Leaders they bring on board can help them grow an average of 25% each, that means we will have added $2.5 billion to the prosperity pie for everyone. That’s thousands of jobs created and dreams fulfilled. That is the movement I want to see!

    How can our readers further follow you online?

    Read or listen to my book Fractional Leadership: Landing Executive Talent You Thought Was Out of Reach or check out my website, to learn more about Fractional Leadership, get a right-fit, vetted Fractional Leader referral, subscribe to our emails, or check out our blog and podcast.