Office Hours, July 23rd: 17 Interesting Questions About Fractional Work, Answered by Taylor Crane

I hosted my second Office Hours on July 23rd. 144 people registered, a great crowd showed up, and we all chatted for about 90 minutes

Here are all 17 questions from the session with my answers. Some are about finding the work, some are about doing the work, and a few are about what I'm seeing from the companies making these hires.

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There's no clean fractional title for the work I do. What now?

Craig asked this one. He started an advisory firm a couple of months ago helping CFOs and CIOs turn their AI and technology investments into real outcomes, he's had about 20 conversations with those buyers so far, and there's no such thing as a posting for a "fractional value realization" leader.

The roles that make it onto job boards, including the one I run, are the ones with obvious full-time equivalents. A Series A founder prepping for a Series B with nobody doing finance thinks "maybe I need a fractional CFO." That's a short trip. It is very unlikely a founder is sitting there thinking "I need someone like Craig."

Work like yours is something you go out and get, far more than it comes to you. Approach the CFOs, CIOs, and COOs directly, iterate on the pitch, and add value by going to them.

And you've already proven the demand. You told me 90% of those 20 CFOs and CIOs said this is top of mind for them. That's the hard part solved. What's left is a matching problem, and my guess is it resolves iteratively. Land a client or two, turn them into proof points, use those to pull in the next ones.

For more reading on this, check out Why Don't I See any Fractional Roles for Me or My Function Area?.

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How do I do business development when I'm already booked?

Nish asked this. She does fractional product leadership, she's six months into an open-ended engagement at 10 to 12 hours a week, and she caps her fractional work at 15 hours because she's building her own startup with the rest of her time. So one client is close to full for her, and she doesn't want to hit famine when this engagement ends.

One honest thing first. When you only have room for one client at a time, some amount of feast or famine is just more likely. Working with several clients gives you a cushion, because losing one doesn't take the whole business with it.

Your own instinct was to ask your client's CEO how he's thinking about the timeline for the engagement, and that's the right first move. Do that before anything else.

Then treat business development like it's its own client. I'd give it five hours a week, which is both a good level of investment in general and roughly the three to five hours you have left after your client work and your startup. Fill it with networking, including second degree connections. What you're driving toward is a real lead who wants to work with you, and that hands you leverage in two directions: you're fine if your current client walks, and you have a reason to renegotiate your current contract for more money. Best case, you end up running a waitlist, telling excited leads you'll reach out the moment you have room.

For more reading on this, check out Lead Gen: How to Get Your First Fractional Clients.

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Which industries are actually hiring fractional right now?

Carla asked this. She's reaching out to companies, edtech especially, asking whether they need fractional help, and mostly getting "what do you mean?" back.

If we surveyed every small business owner and startup founder in the country, I'd bet the overwhelming majority land in one of two camps: never heard of fractional, or heard of it and never paid attention. So when the word doesn't land, that's the norm, not a sign you're doing it wrong. You're on the leading edge.

On sectors, we have a research report coming out in the next two to three weeks that goes deep on this. The short version: early stage startups of every shape and size are the dominant buyers, venture backed ones especially. Healthcare is the other big one at around 14% of the hiring in our data. What I can't tell you yet is whether that 14% just reflects how enormous healthcare is as a share of the economy, or whether healthcare hires fractional talent at a higher rate than everything else. Either way, most of your clients will still come from you working your network, not from a company out shopping for fractional talent.

For more reading on this, check out The Types of Companies That Benefit Most From Hiring Fractional Talent.

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Is it worth requesting an intro if I miss one of the must-haves?

Holly asked this. She found a featured role on Fractional Jobs that she fits on every requirement except one, and wondered whether requesting an intro anyway would just waste everyone's time.

Some context on how our Featured Jobs work. I write every one of those job descriptions myself, based on my conversations with the client, and the "about you" section lists must-haves and often some nice-to-haves. The client and I build that must-have list together, so it reflects what we both believe is genuinely required.

So, directly: if you read a must-have and you unequivocally don't meet it, you're in the long shot category. But job descriptions are an art as much as a science, and whether a gap actually matters depends on who else applies. I can point to plenty of cases where a client hired someone who missed a bullet, so it wouldn't be truthful to call it a hard requirement 100% of the time. There's no way for you to know which kind of bullet you're looking at, and usually the client doesn't know either, because they only get clarity once they start meeting candidates.

So here's the actual decision. My goal is for an intro request to take you 5 to 10 minutes. If it's taking longer, something's off, usually that you're stretching to explain your experience. The question is simply whether a long shot is worth that. And when you know you're missing a criteria, name it in your request and explain why you think it's still a match. That's by far the strongest move.

One related thing I hear constantly from people who don't make it to the intro stage: "I could learn that in a week." I believe you. But fractional is new to clients and there's skepticism baked in, which produces a strong desire to get it right. On a four or six month part-time engagement, there isn't much appetite for someone learning on the job when the alternative has obviously already done it.

For more reading on this, check out How to Submit a Great "Intro Request" on Fractional Jobs.

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Is fractional about how long the engagement lasts, or how many hours a week?

Holly asked this too. She'd noticed I keep calling fractional work short term, while her own definition is about hours, something like 2 to 5 hours a week.

Your version isn't wrong, it's just one of the two dimensions. Fractional is part time, and I'd count anything under 40 hours a week, so 2 to 5 hours a week absolutely qualifies. So does 20.

The part worth clarifying is what I mean by short term, because I don't mean the engagement has an expiration date. Fractional in my definition is indefinite and can run for years. What I mean is that if you compare the average fractional tenure to the average full-time tenure, full-time is longer. So as a category it sits in short to medium term, even though any individual engagement might not.

For more reading on this, check out What Does a Fractional Job Typically Look Like?.

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How do I pitch fractional to an industry that's never heard of it?

Christina asked this. She supports mission based organizations, education, nonprofits, and NGOs, where fractional isn't on anyone's radar, and she wanted to know how proactively pitching differs from reactively applying to posted roles.

This may be a strange thing to hear from the guy who runs the job board, so here it is plainly. If your only source of leads is browsing Fractional Jobs or LinkedIn, you're going to have a bad time. I'd expect at least 80% of your clients to come from your own network or from real work you're doing to generate inbound and outbound leads. Treat Fractional Jobs as the cherry on top. Nobody is building a practice on any platform right now, mine included.

So almost all of your effort belongs in the proactive column, and the proactive column is sales. When you're new, be virtually 100% focused on conversations with your network, then conversations with their network. Cold outreach and channel partnerships are what you graduate to. The gut check: if you can't find clients in your own network after several months, you're very unlikely to find them cold.

One more thing worth knowing when you're selling into a market that's never heard the word. Plenty of fractionals land their first client from someone who simply wanted to hire them and took the fractional arrangement as the only way to get them. It sounds like "I want to hire you full time so badly, and you're telling me I can't, so I'll take 20 hours a week instead." You don't always have to sell the concept first. Sometimes you just have to be the person they want.

For more reading on this, check out How to Get Your First Fractional Clients.

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Do I need a resume built for fractional work?

Robert asked this. He didn't have a fractional resume when he first went fractional, built one recently because Fractional Jobs kept putting him in front of opportunities, and wanted to know the best practices for it.

Your resume is not that important. Your LinkedIn is about ten times more important. That's why the resume attachment on an intro request is optional, by design.

What I'd especially avoid is dedicated time rebuilding your resume for fractional. I see people restructure the whole thing, fractional engagements moved to the top and full-time experience buried at the bottom. I understand the instinct, but when clients evaluate you they're trying to work out where you're an expert and where you're better than everyone else, and that mostly comes from your full-time record and your career trajectory. A client hiring a fractional CFO wants to see that you were a full-time CFO at relevant companies.

Your fractional engagements are still worth listing, and for some clients they matter a lot. I'm working with one right now who won't talk to anyone who isn't already fractional with multiple clients. But the full-time track record is what establishes the expertise, so take the effort you were going to spend on your resume and put it into your LinkedIn profile instead.

For more reading on this, check out The 10-Second LinkedIn Fix That Could Double Your Leads.

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What if LinkedIn is dead for me and my network is tapped out?

Craig came back for this one. Two things I'd said in the previous answers had scared him: that LinkedIn is a fractional's most important asset, and that a network which hasn't produced a client after a few months is a bad sign for cold outreach. He's worked through all 3,000 of his LinkedIn contacts and watched his whole network disengage from the platform, so neither one landed well.

Let me try to unscare you, starting with LinkedIn. What I said was about your profile, in comparison to your resume. Resumes are getting harder to trust as a signal, because AI resume generators have gotten sophisticated enough to spit out a custom, keyword-stuffed version for every role, written to game the screening software on the other end. Your LinkedIn profile is different. It's public, it has your name on it, and anyone you've worked with can see what you've claimed. Using LinkedIn to generate leads is a completely separate question, and if that channel is genuinely tapped out for you, that's real and it means putting your effort somewhere else.

On the few months figure, that was a rough ballpark and I'd apply it to the more typical fractional roles I see. What you're offering isn't cookie cutter like a fractional CFO or CMO, and the more unusual the offering, the less these general rules hold. So don't be that scared. That said, I'd still want to know why your network isn't producing, because warm introductions are the easiest leads there are.

For more reading on this, check out Why Your LinkedIn Isn't Generating Leads (And What To Fix First).

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Should I pay an agency to run lead gen for me?

Matt asked this. He's new to fractional, and people keep messaging him on LinkedIn offering to take over his profile and run outbound to hundreds of people a week, usually around $5,000 for a one to three month engagement.

Short version: I'm very, very skeptical, for two reasons.

The first is that cold outbound is an advanced tactic. It belongs after you've exhausted your network and have some proof points, and it only really works when you have a dialed in ideal customer profile you can identify at scale. If your offering is still being refined, outbound isn't going to save it. The second is the incentives on the other side of the pitch. In a gold rush, you sell picks and shovels. Fractional is growing, and a lot of companies have worked out that the reliable money is in selling services to fractionals rather than doing the work themselves. That's who is messaging you, and they're happy to take $5,000 from someone who has never had a client.

I've also never heard a single success story from one of these agencies. Not one, and I've asked repeatedly. That doesn't prove they don't exist, and I'd love to be wrong. If you've worked with one and it went well, email me and I'll put it in the newsletter. In the meantime, if you're still curious, vet them hard and actually talk to references.

For more reading on this, check out Why Some Fractional Leaders Never Struggle for Pipeline (And How to Become One of Them).

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Why are there so few fractional product roles?

Ishan asked this. He's a product leader looking for fractional product work, and his theory was that companies want product leadership full time so they can plan longer term strategy.

I don't think that's it, and I should flag my bias: my background is product too. I spent 10 years as a PM, then a year as a fractional Head of Product. Product people especially assume the job can't be done part time, because the thinking goes that you have to live and breathe the user and think about the customer in the shower. I hear that about every function. And my answer is simple. A startup with no product leadership at all is way better off with 10 hours a week of Ishan than zero hours a week of Ishan.

Here's my actual theory, which I've written about before as the levels of fractional hiring. Level one is where it's obvious the founder has to look outside the company. They need strategic finance help, it's clearly not them and clearly not their CTO, so they look out and land on a fractional CFO. Product is level two. When a founder who came up through sales starts feeling the need for product strategy, the first instinct is to solve it internally, so the CTO gets told he's now also the Head of Product. Operations goes the same way. That's rarely the right call, but it means the founder never gets to the point of looking outside, which is why you see fewer of those roles posted.

Level three is my favorite: roles with no great full-time equivalent at all, like a fractional Head of User Research. How often does a company hire a full-time Head of Research? Almost never. In a fractional context it makes complete sense.

For more reading on this, check out Why Don't I See any Fractional Roles for Me or My Function Area?.

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What's the difference between fractional and consulting?

Ishan asked this as part two of his question, since he'd heard people insist they're the same thing and heard others insist they're completely different.

Both camps are partly right. Fractional work is a type of consulting work, so picture a Venn diagram with fractional sitting inside consulting. The differences are in the nuances.

My definition: fractional work is part time work, typically paid on a monthly retainer, performed by experts in their field. The retainer piece is doing real work in that sentence. When we picture a consultant, we usually picture project based work. Someone comes in, makes recommendations, builds a deck, tells the company what the strategy should be, and keeps themselves at arm's length. A fractional leader is embedded. They are the CMO, just part time. They're leading the function, they're the expert in the room, and they happen to be a 1099 on a technicality.

For more reading on this, check out The Difference Between Fractional Work, Freelancing, Consulting, and Agencies.

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How do I protect myself from a client who doesn't pay?

Isha asked this one. Her first fractional client came through a warm introduction from someone she and the founder both knew, they signed a contract, and she still hasn't been paid.

This is exactly why some fractionals take payment up front. The common structure is that work begins when the first invoice is paid, and you invoice at the start of every month or before kickoff. There are variations too: first invoice up front with everything after that on net 7, or a deposit covering the first two weeks.

The catch is that invoicing up front takes leverage, and leverage is exactly what you don't have early on. If it's your first client ever and they know it, you're not in a position to insist. In the full-time world people get paid after the fact every two weeks, so a client won't necessarily see up front payment as normal. What I've noticed is that the more years someone has in fractional, the more likely they are to invoice up front, usually because they've been burned once.

I also want to be careful here. When I was doing fractional work I never invoiced up front, and I think that's still the norm early on. So please don't leave this thinking you must. It's a risk and reward call, and you should use your judgment. And on what happened to you specifically: this came through a referral from your own network, which is about as much diligence as anyone can reasonably do. You got very unlucky.

For more reading on this, check out How Fractional Workers Can Manage Late or Non-Payments from Clients.

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Does a professional website improve my odds of getting picked?

Ying asked this. Her theory was that a real company website reassures a client you're committed to fractional work and won't jump back into a full-time operating role the first chance you get.

Let me take the premise first. My read is that fractional work attracts exceptional people rather than repelling them, because it gives them more control over their career. So if a founder is worried you'll bolt for a full-time role, that's a misconception on their end.

On the website itself, I see the appeal. It plants a flag: I'm a fractional XYZ and I'm here to stay. But you can plant the same flag on LinkedIn. And spinning up a website now takes one prompt and about 10 minutes, so I'm seeing more and more of them, which cuts against whatever signal value they used to carry. If it's fun, build it. If it gets you to put case studies and work product somewhere public, even better, because those do lend credibility. But it's a nice to have. Your LinkedIn is by far your most important asset.

For more reading on this, check out How Fractional Execs Can be the Ideal Candidate and Win Clients on LinkedIn.

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Should I target companies that have already hired someone fractional?

Ed asked this. He's a fractional general counsel, a role that basically never gets advertised, so rather than pitch cold he looks for signals that a company is already comfortable with fractional, like having a fractional CFO on board.

Your instinct is right, and I've watched it play out. One of my biggest learnings in building Fractional Jobs was how many repeat clients we get, companies coming back to hire a second, third, and fourth fractional person. Way more than I expected.

It makes sense, too. When you pitch a company that has never hired fractional, you're doing double duty: first convincing them that fractional is a real way to solve their problem, then convincing them you're the right person. A company that already has a fractional CFO is done with the first half. All you have to sell is the fractional GC part.

Your other signal is companies hiring a chief of staff, on the theory that a CEO reaches for one right around the time legal issues start piling up, too expensive for outside counsel but nowhere near a full-time hire. I don't have a view on whether that holds, but it could be a good one. Two more I'd look at for your role. Target companies in regulated spaces that are going to need legal help, then check their LinkedIn to see whether anyone on the team is in a GC or legal role. And look for the COO or chief of staff who's clearly absorbing legal work they shouldn't be. Job postings that quietly stuff legal responsibilities into a non-legal role are a great tell.

For more reading on this, check out Hiring a Fractional General Counsel.

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Is my positioning real, or am I just getting work through my network?

Sean asked this. He's a CPA and fractional CFO whose work comes in through friends and former colleagues who can vouch for him, and he can't tell whether that reflects positioning that would hold up with strangers or just goodwill. He's also not sure the work coming in is the work he wants.

I'll answer with my own story, because it gets at this better than any framework I could give you. I started doing fractional work in early 2023, and my initial positioning, which I'd barely formalized, was "fractional Head of Product for early stage startups." That is not good positioning. My first client came through my network. My second came through my network, via a private group. Third and fourth, network again.

It was only after those first four that I looked back and started drawing threads between them. All four were non-technical founders who were deep industry experts in their own domain: mental health, legal, education, and web3. None of them knew anything about product or engineering, and I was adding most of my value as the conduit, helping them figure out how to build software, get an MVP to market, and manage an offshore dev team. That became the positioning, and the important part is that it emerged out of the work rather than being declared before it.

So I wouldn't over-focus on nailing your positioning right now. You have clients coming in the door. Keep going, then look back and find the threads. You refine it iteratively.

For more reading on this, check out How to Position Yourself to Attract Fractional Work.

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If networking is my main channel, do I reach out to everyone or wait for a signal?

Michael asked this. He's after fractional COO and head of ops work at small and medium businesses, he still runs a small education company of his own, and he's worried about pouring time into relationship building that goes nowhere.

If you spot a signal at a company that needs what you do and you have a mutual connection who can introduce you, that one's easy. Go.

The bigger question is what "networking as a channel" actually looks like day to day. It starts with the people who already know you and know your work. You're not prospecting them. You're making them aware of what you're doing so that you're top of mind, whether that's a virtual coffee, a catch up, or just an email. Then you're hoping it pays off three months later when they run into a company that needs you. The second half is reminding them, because one conversation isn't enough, and this is where LinkedIn earns its keep. Not thought leadership aimed at strangers. Just reminding the network you already told that you're still doing the work.

You also asked whether you could skip that public half, since posting about fractional work to an audience built around your education company might confuse them. Yes, and you should start with the private half regardless. My Lead Gen playbook covers the two in order: engage your network privately through one to one outreach, then engage your network publicly. Plenty of people can't do the second one, and that's fine.

For more reading on this, check out Lead Gen: How to Get Your First Fractional Clients.

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How do I handle a client whose hours swing wildly week to week?

Priscilla asked this, her first time joining. She spent 10 of her 20 year career on the vendor side of the Costco business and now helps small and medium sized suppliers save millions on their Costco operations, which makes her workload lumpy by nature. She has one client at one day a week, some weeks two hours and some weeks far more, and she's already capped contract carryover at four hours a month so she isn't left holding the bag.

Right now you have one client, so you have the flexibility to ebb and flow with them, and that's exactly what you should be doing. The problem gets bigger as you add clients, but so does your leverage. When you're at three clients and you have to tell client number one that two hours one week and ten the next no longer works, you walk into that conversation with two other clients and their income behind you. So handle it as needed, and reevaluate when you land the second one. A strict use it or lose it policy on unused hours is a valid option too, the more aggressive cousin of the carryover cap you already have.

This is also what retainers are good for. You agree on a retainer covering, say, 10 hours a week. Then when more work comes at you than that, you say: I can't get all of this done in 10 hours, let's prioritize, some of it moves to next week. Over time you're training the client that your job together is to scope the work to fit the hours. But it's a dance, and some clients take it better than others.

The one thing I'd add for your situation specifically is that some of the lumpiness isn't a problem to solve. When Costco comes at one of your clients with a big bill, that week is enormous, and being there for exactly that is a big part of what you're being paid for. Fractional CFOs on the controllership side live with a version of this too, since every client's books close on the same day. That's the game.

For more reading on this, check out Should I Charge an Hourly Rate, a Monthly Retainer, or Something Else?.

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That's a Wrap!

Two Office Hours in and I'm having a great time with these. My voice feels differently about it (lots of talking).

We're doing it again in August. If you've got a question you want to bring, watch the newsletter for the registration link.

The whole Office Hours series is presented in partnership with Collective.com, and I'm super grateful for them. If you're at the point in your fractional practice where you need to set up your LLC or S Corp and start taking your business more seriously, you should learn about how Collective can help.