Category: The Business of Writing

Working With Freelancers? You’d Better Have a Plan – and Be Ready to Talk

~ iambeastwood ~ Leave a comment

Since branching out from journalism and market research nearly a decade ago, I’ve worked with a lot of clients (and clients’ clients) in a content role. These companies have operated in several healthcare and technology market segments, and they’ve ranged in size from startups to multinationals, but many have had one thing in common.

Sometimes it happens almost immediately, and sometimes it takes several months. But nearly every time, the conversation shifts from “We’d love to have you on board to do foundational long-form content!” to “Hey, can you write a press release?” or “Hey, have you ever written web copy?” (Or, in the case of where I worked full-time for all of 8 months, “Hey, can you copy edit a PowerPoint our client’s using for an internal meeting?”) In most cases, this shift follows a period when my workload has been lighter than expected, whether explicitly stated in my contract or generally agreed upon in principle.

Be honest about the workload you can offer

There are typically two factors at play in these situations. One is immediate, readily apparent, and fairly superficial: The client ran out of things for me to do. Throwing another project my way can certainly serve as a stopgap measure, and make me feel appreciated and wanted, but it tends to reflect the second, much more systemic, factor: The client never had enough things for me to do in the first place.

I’m generally sympathetic toward whomever the client has tasked with managing me, since the dried-up content pipeline usually falls on the shoulders of someone else. I’ll express frustration, but I’ll do it politely.

I’m less sympathetic to the clients themselves. Why would you enter a business agreement with a content person without a clear-cut plan for providing them with a steady stream of work that makes the most of their capabilities?

I’m not arrogant enough to think that every content meeting has an agenda item called “What to Assign to Beastwood, Our Amazing, Funny, and Handsome Content Guru,” but it’s not unreasonable to think that you’re at least occasionally talking internally about how to use the skills of the person you agreed to pay to do work for you on a regular basis.

If you don’t expect a regular cadence of work, that’s fine. Hire the writer to do your foundational content, pay them, and then call it a day. Or, hire them to do occasional work, with the understanding that they may not always be available because, well, you’re only asking them to work occasionally, and chances are they have other work from other clients who do give them regular assignments, and therefore plan for a project to take a few weeks to complete.

Both of these arrangements are perfectly reasonable. I’ve done single foundational pieces for more than one client, and we’ve both walked away after the piece was done, happy with what we’ve produced and knowing full well that would be the end of that. I’ve also worked with multiple clients who’ll reach out every few months with an assignment that’s not especially time sensitive. This work won’t win me a Pulitzer or pay for our overdue bathroom renovation, but it will add to my writing portfolio and After-School Snack Fund without leaving me frustrated or befuddled about a lack of follow-up.

Make a plan before making promises

Don’t promise a writer a regular cadence of work – a set number of hours per week, or a set number of pieces per quarter – without first knowing how you plan to get the writer that work and then sharing that plan with the writer. You need to be able to account for five things:

  • What you want.
  • When you want it.
  • What you can pay for it.
  • Who you’re relying on (mostly internally, but occasionally externally) to get the writer what’s needed to get it done.
  • What will hold it up, whether it’s a release date that may not actually happen or a team of executives arguing in Microsoft Word comments whether a solution synergizes data or leverages it.

At best, without a plan you’re flying by the seat of your pants trying to keep a writer busy, and you’re not meeting the expectations set forth in your contract. At worst, you’re leaving a writer on standby, telling them that work is coming at some point, probably soon, but maybe later – and giving them all the more reason to look for clients that don’t promise something they can’t deliver. (And, if you have the person on retainer, you’re probably lighting some money on fire, too.)

Don’t be afraid to talk about it

Here’s another way to think about it. That freelance writer is essentially a business partner. Odds are they’ve created an LLC, or at the very least a DBA and business checking account. They probably have an accountant and calculate business expenses (even if they’re primarily Post-It notes, newsletter subscriptions, and reams of printer paper that may or may not also feed their child’s crafting supplies).

Does your company leave its traditional business parters guessing, or do you routinely check in with vendors and consultants? When things start to get light, do you forget about them, or do you work together to come up with ways to get more done, in accordance with their skills and your shared expectations?

There are plenty of reasons for a content pipeline to dry up. I get that nearly all of them are beyond your control when you’re one cog in the corporate machine. But if you want to build longstanding relationships with freelancers – who will remember you when you take on a new role and, on the other hand, won’t be afraid to spill the tea if things fizzle out – then it pays to treat them as partners.

That means having a coherent plan for how you intend to work together, along with having difficult conversations when that plan starts to fall apart. The sooner you open those lines of communication, the more likely you are to avoid the awkwardness of explaining to them (not to mention your boss, and probably the people who make your budget) why there’s nothing for them to do. You’re also more likely to salvage the situation without having to tell a freelancer they can’t work with you any more because you ran out of money or capacity – or having the freelancer walk away because they’re smart enough to see the writing on the wall.

You Don’t Have to Pivot Just Because the Pretty People on the Internet Tell You

~ iambeastwood ~ 1 Comment

Back in April, Allbirds made lots of headlines for pivoting from sustainable shoes to AI, which is pretty much the opposite of sustainable. I won’t miss them; I prefer shoes with support, stability, and no army of tech bros behind them.

Like any halfway decent Th0u9ht LeaDer *and* self-proclaimed small business owner, though, I couldn’t help but look at the reaction to the Allbirds news and think about what it means to honestly, actually, and meaningfully pivot. It’s an inevitable dilemma for just about everyone in the working world: Do I stay where I am, and risk becoming less relevant, or risk leaving behind what I know for something less familiar but potentially more lucrative?

The dilemma is especially acute when you’re a writer. The ol’ algorithms serve up all kinds of content aiming to convince you become a strategist, launch a podcast, or start a newsletter. If you’re independent, you’ll see advice to go in-house; if you have a corporate gig, the world will try to convince you to go solo. One post will tell you to become a generalist; another will suggest you find your niche. Oodles of people will offer unsolicited advice on using AI to automate all kinds of stuff so you can (presumably) spend less time working and more time sipping drinks in Cabo.

Your pal Beastwood isn’t here to tell you what to do. I’m just going to tell you to think long and hard about what you want to do and how you want to do it – and shut out all the noisy distractions.

Mistakes? I’ve made a few.

I say this because I have a good history of professional pivots that, um, well, uh, leave Current Me wondering that the hell Past Me was thinking. (Some of you who have known me long enough were probably wondering, too…)

  • In the summer of 2000, lured by a classified ad promising $18 an hour (plus commission), I took two days off from my job at the local supermarket to get a crash course in selling knives door to door. Even if you only know me through my writing and haven’t met me in person, you can probably guess how hilariously bad I would have been at this. (It’s OK to laugh. I am, too.)
  • At TechTarget, bored by .NET application development, I moved to the company’s fledging Enterprise Software group, the publisher of which had ambitions for dozens of complementary sites. The group and its exceptional burn rate folded within a few months. Luckily, one of the verticals had been in healthcare, and I was able to move over to the not-yet-launched SearchHealthIT.com. (That at least worked out in the long run.)
  • In 2012, I left TechTarget for CIO.com so I could get “senior” in my title. But I missed covering healthcare fulltime, so in late 2014 I left for Fierce Health. There, I quickly remembered why I’d left the daily news business a decade ago, and less than eight months later I landed at Chilmark Research.
  • Though Chilmark was serving me well, the company was struggling to grow. I pondered additional steps and landed on joining an agency, as it would round out a resume that included stints as a journalist and analyst, and who wouldn’t like such a well-rounded resume? Shortly after joining, I pondered why I thought that was a good idea.
  • I left the agency for World Congress in June 2019, thinking that conference production would make use of my expertise, somehow be better than agency work, and make the resume even rounder. (More circular? Who knows?) It wasn’t. In this case at least, the pandemic forcing the company to lay off everyone who wasn’t a VP was a professional blessing in disguise.

TL;DR I bounced around a few times and learned the hard way that I didn’t want to do before I managed to figure out 1) what I did want to do and 2) how to actually succeed in doing it.

Too much pivoting = spinning in a circle

As I tell my 5-year-old whenever he doesn’t get something quite right, it’s OK to make mistakes. (For my purposes here, I mean mistakes like “took a job because it gave me a 15% raise even if the CEO gave me weird vibes” or “took a job so I could leave a company behind even though I didn’t love the new opportunity” and not, like, “forgot to put out the fire at the campsite.”)

I believe it’s also OK if you don’t learn from those mistakes right away – provided, again, that no one’s in harm’s way because of it. It takes time to figure out what you want to be when you grow up. Especially in Today’s World, the first job you take isn’t going to be your last, and no employer worth their salt should be the least bit surprised if a worker wants to leave for greener pastures.

Eventually, though, you need to reach a point where there’s a method to the madness of your pivots. Want a managerial role? Want to move into an adjacent vertical? Want more money? Want to live in Europe? Want different projects? They’re all perfectly reasonable motivations taking a new job, or a new client – but you should be able to explain why you’re making that move. Otherwise, you’re not pivoting; you’re spinning in a circle.

And – because, yes, I am in fact tying these points together – you understand why you’re making the move by learning from your mistakes. I’ve learned the topics I’m suited to cover, the varieties of products I like to work on, the types of clients I prefer and – critically for me – how much structure I need to have in place if I’m going to do something new. I can stray a bit off topic, or create written content in unfamiliar, if a client has given me good guardrails; otherwise, experience has taught me I’m not going to do so well.

Sorry, not interested

I’ve learned the hard way that there are a few professional pivots I’m not interesting in pursuing.

  • Content strategy. I strongly prefer working with people who can tell me what they want.(What they really, really want, in fact.) I’m a sandwich-generation caregiver for my son and my mother, both of whom happen to be at opposing developmental stages where it’s often frustratingly difficult to communicate with them. I don’t need work to be the same way.
  • Straight-up marketing. I know web copy, email campaigns, and social media posts are vital for many digital health brands. I’ve also found a lot of this work is below my pay grade, especially if clients plan to pay an hourly rate. This is one of those areas where I turn to my network for referrals so at least I’m not just saying “No” and moving on.
  • Standalone proofreading projects. Same as above – the juice isn’t worth the squeeze given what these projects tend to pay, especially if I have to get onboarded and do cybersecurity training and fill out six forms to get paid. (If it aligns with topics I know well, though, I’ll consider it for existing clients.)
  • Very niche topics. There are a handful of elements of enterprise tech, drug development, and healthcare operations that make absolutely no sense to me no matter how many times I try to figure them out. I’ve let myself – and my clients – down enough times to know not to bark up that tree any more. Again, I’ll put some feelers out to my network in these cases.
  • A paid newsletter. The mediocre middle-aged white man confidence bouncing around my head tells me I could probably do this. The Principal and Co-Founder of my one-man LLC says it’s not worth it. I tend to agree with him: I just can’t foresee the payoff being worth all the work that would require. (Also, have you seen who has newsletters on Substack, or what the beehiiv founder’s been posting about? I have no interest in being even remotely associated with that.)

If you pivot, you should have a reason

I present that list of Stuff Brian Doesn’t Wanna Do because each item has something in common. If you spend enough time aimlessly scrolling, you’ll inevitably come across accounts (whether they are in fact people is partially in doubt) suggesting those are the things you should do to build your business.

I’m here to tell you that you don’t have to if you don’t want to. In fact, you should resist the temptation to pivot just because voices on the Internet say you should. Remember the lure of $18 an hour plus commission to sell knives door to door? It wasn’t worth it. Hell, it was probably a pyramid scheme. I was better off without it.

That brings me to a broader point: Nobody telling you that you simply must pivot has your best interests in mind. They want to sell you something.

I don’t mean, like, one eBook, publication list, or professional membership that will pay for itself as soon as a pitch is accepted, a project is assigned, or even a new connection is made. I mean those courses that give off the vibes of timeshare presentations and self-help seminars rolled into one – without the allure of free food (since they’re undoubtedly virtual for your viewing pleasure). Those resources that never quite give you the information you want, either because they’re so basic you already knew it all or the really good stuff costs five times more.

Look, I’m a privileged white guy. It’s easy for me to say “keep doing the work you like and pass on the stuff you don’t like.” My family will still eat if I say “No” to something that sounds lucrative but puts me too far out of my comfort zone.

But I also think I can say the seemingly aimless wandering of my career has taught me that pivoting for the sake of pivoting usually doesn’t work out the way you want it to. If you have good reasons, and you’ve thought about it, and you have a plan of action, it’ll probably work. But if you just want change – because you’re bored, external influences seem to suggest you should, or no one wants your eco-friendly shoes – it’s worth thinking about what’s truly behind those feelings and whether smaller, different steps can satisfy those motivations.

The Future of Telehealth: eBook Is LIVE

~ iambeastwood ~ Leave a comment

My first eBook – Telehealth’s Next Chapter: A Tale of Volume and Value – is officially live and available for download.

The eBook is a couple years in the making. Back in 2023, telehealth utilization was two years into a plateau following a mid-pandemic peak. In a lengthy blog post, I speculated on what that meant for telehealth’s future, and whether there was anything the healthcare industry could do to shape that fate. The post got a lot of positive feedback, including several recommendations for what I could add to augment my thesis and turn the post into an eBook.

If you’ve known me for even a short time, you know I like challenges. You also know I tend to overextend myself juuuuust a little bit – which is why, amid building a freelance business, raising a child, running marathons, hiking up mountains, and doing my best to clean the house, the eBook has finally arrived.

From a blog post to an eBook

So, what separates Telehealth’s Next Chapter: A Tale of Volume and Value from the blog post that preceded it?

  • There’s some historical perspective. This demonstrates that telehealth has pretty much always been about episodic care and explains why utilization has been on a plateau for four years running.
  • There’s a brief unpacking of the struggles of digital health companies not named Hinge Health, Omada Health, and (at the time I was writing at least) Hims & Hers. This offers perspective about why the road ahead for telehealth is a bit bumpy.
  • There’s a Debbie Downer take that the best time to act has passed us by. I think it’s because the industry’s bevy of stakeholders weren’t sufficiently motivated to act to remove barriers to adoption in the summer of 2021.
  • There’s an offer of a path forward – telehealth utilization that supplements value-based, purposeful in-person care in a wide range of scenarios – and a set of suggestions for how the many stakeholders involved will need to collaborate.
  • There are some lovely graphics, which I designed myself, and some of the best stock art that a free Canva account can buy.

Incredibly, over the course of 42 pages, there’s only one reference to running, and it’s in my bio. If I’m being honest, this very well might be the eBook’s greatest achievement.

Free for a little while longer

Initially, I planned to make the eBook available as a free download over Father’s Day weekend, complete with a great dad joke about it being my gift to you, and then charge folks for it. I even came up with a price of 73 cents per page, as a nod to Regina Holliday.

The idea, as I stated in a LinkedIn post I’ve since deleted as well as a blog post that has since disappeared for reasons I’ll explain, was to see if creating and publishing my own content would be a worthwhile extension of my freelance business.

Then, a few things happened in rapid succession.

  • I stopped using my web hosting service, which I’d decided wasn’t really meeting my needs. In doing so, I wiped out the version of my website that included the product page for the eBook and the blog post announcing it to the world. Oops.
  • As I transitioned back to WordPress, my website was down for a few days. At this point, I offered to send the eBook to anyone who asked me for it, as I had no way to collect anyone’s hard-earned money.
  • Sometime between finishing our Monday morning viewing of Daniel Tiger and attempting to start the work week, the wires that bring the Internet into our house got clipped. Even if I wanted to update my website, I couldn’t. (Unless I wanted to roll the dice with the open Wi-Fi at the public library, which I didn’t.)
  • I came to realize I never really gave a lot of thought – any, really – to how I planned to promote the eBook once I’d launched it.

Given all that, I’ve decided to make the eBook free for a bit longer, either as a download on this here website or by asking my nicely on LinkedIn or via email. The $30.66 cost will go into effect on July 8, after we’ve all recovered from the long weekend. 

The first of more to come

My rationale for charging for the eBook is partly to try to cover expenses (I paid my reviewers, got professional headshots, and upgraded my website) and partly to see if there’s true demand for this type of thing. It’s not the end of the world if I take a loss. For good or ill, in the back of my head this was as much of a passion project as it was a business venture, along with a fairly low-stress way to revive my rudimentary graphic design skills. Plus, it’s already had more views than my graduate thesis, which took a lot longer to write and cost a lot more to boot.

That said, it’s hard for me not to scratch the itch for longform writing. One of my Internet-less tasks this week was starting the outline for the next eBook I hope to write, which I’d previously scrawled on a few Post-It notes in my planner. The topic: Why the philosophy of patient engagement has made great strides in the last decade even if the market for patient engagement technology kinda sorta floundered. It probably won’t be 42 pages, but it also probably (hopefully?) won’t take me more than two years to write.

As long as my schedule allows for it, I intend to create more content of interest to the digital health community.

Holy Cow, I’ve Been At This For Five Years

~ iambeastwood ~ Leave a comment

Roughly five years ago, I joined the ranks of millions of Americans who lost their jobs at the height of the pandemic. I wasn’t shocked by any means, as I worked for an in-person event company and focused on the healthcare industry. In fact, after my managers delivered the news to the entire editorial team, they called me for the first of the one-on-one chats with the recently departed because they expected, correctly, that I would take the news well.

I don’t remember the exact date, but I do know it was a Thursday morning with weather similar to this one. For the rest of the week, I spent some time relaxing and some time fiddling with the WordPress site I’d launched in 2017 and then quickly forgotten about.

I also spent some time thinking about what to do next. Getting laid off was the latest in a series of turns in my career. In both 2012 and 2014, I left one tech publishing company for another. In 2015, I took a job as a research analyst. In 2018, I moved to an agency. In 2019, I went into the event business. It’s fair to say I was having trouble figuring out what I wanted to be when I grew up.

Amid my various moves, I’d started freelancing a few hours a week in 2015. One friend recommended me for some work reviewing running watches; another thought I’d be a good fit to write about executive leadership and enterprise IT. Over time, I took on a couple more clients in higher ed and healthcare tech, and I set up the aforementioned website to highlight my work. Soon, though, the work eventually became juuuust a bit too much to handle.

I missed it. I frequently chatted with full-time freelancers who were not only making a living as writers but thriving, thanks to their business acumen and time-management skills. In the back of my head, a future version of myself had that role. I can’t remember if it was something I daydreamed about on my commute or during my runs, but I definitely thought about it.

That said, I couldn’t see myself leaving a full-time job with benefits. Fear of the unknown proved more powerful than building a professional life as a full-time freelancer with a lot more writing and far fewer meetings. Put another way, the perceived risks of going out on my own outweighed the benefits of being my own boss, as numerous as they may have been.

Then, well, it was April 2020, and pretty much nothing was stable – jobs, health, the future, one’s supply of peanut butter, etc. I sat down with my wife for a chat. The main takeaway: “Go do this thing. It’s now or never.”

So, on Monday morning, after filing for unemployment – a key safety net as I got started – I sat down in front of the personal laptop I hadn’t opened in close to two years. I reached out to my former freelance clients. I got in touch with past colleagues from my (many) previous full-time jobs. I researched publications, consultancies, and brands with content that aligned with my past work and crafted some cold emails to send along. After that, I probably went for a run on a secluded path.

As those early hours turned to days and weeks, I’m forever grateful to everyone willing to give me work in the early days of my shift to working for myself.

I’m honestly shocked sometimes to look back and see where I am now. I’ve found my footing, achieved stability, and learned where I want to focus my efforts. I have an LLC, my own domain name and, once I get around to it, a business email address. I never imagined I’d be in a place where I’d feel comfortable bringing an eBook into the world, and yet here we are. (You didn’t think I’d get this far without mentioning my eBook, did you?)

I’ve also made some mistakes along the way, and I’d be remiss in talking about my success without acknowledging these failures. For example, I discovered that content for life science isn’t my forte, short turnaround times are difficult for me to accommodate, and certain nuances of enterprise technology are beyond my expertise.

I need to recognize that I didn’t start from scratch, too. I was privileged to have a robust network, a nest egg, experience as a 1099 contractor, a business checking account, an excellent mortgage rate, employer-sponsored health insurance, and clips when I started sending those emails asking for work in April 2020. Heck, I even had that dormant website. Yes, I had skills and expertise, but even that was mostly a matter of being in the right place at the right time and managing to take advantage of my good fortune. After all, I never would have gotten into healthcare if the CIO group at TechTarget wasn’t in need of an editor for its new healthcare site and I wasn’t in need of a new role as the Vertical Software Media Group was shutting down and just so happened to have recently dabbled in writing about EMRs and practice management software.

That’s why this post is primarily a Thank You to so many folks for helping me along the way. I may have done the work, but *you* have trusted me to do that work and been willing to vouch for me when others are looking for someone who can do that work. While I’d like to think it’s improbable that I’d be wandering aimlessly in the wilderness without all of you, I do know I’d be nowhere near my current level of success.

Here’s to five years of freelancing down and many more to go. Now if you’ll excuse me, it’s time to go for a run on a secluded path. After all, no matter where things stand in my professional life, some things will never change.

You Say You Want a Content Strategist – But What Do You *Really* Need?

~ iambeastwood ~ Leave a comment

My last three official roles all involved content strategy to some degree. Two even included “content strategist” in the title.

None of the three roles really focused on strategy, though. While that’s not the lone reason I’m no longer in any of those roles, a lack of clear expectations certainly played a part.

As I’ve continued my transition to full-time freelance writing, I’ve been thinking about why none of these roles met my expectations, and whether my experience is solely related to me or emblematic of a larger challenge for anyone seeking to fill a role with what they believe should be a content strategist.

Strategy Is Easier Said Than Done

The biggest challenge, I think, is that strategy is easier said than done. When you hire or promote someone to a role with strategist in their title, whatever the job or the industry, your primary aim is to project to the outside world, “We’re thinking big. Change is coming.”

Are you really, though? And is it? Consider the following.

  • If your strategist is limited to working within the confines of your existing processes and systems, without having much leeway to operate differently, then, well, you’re not thinking big. You can’t and shouldn’t be surprised if the results turn out to be pretty much the same. You can only fix a broken dishwasher so many times.
  • If the bulk of your strategist’s work is actually tactical, that’s also a problem.
    • Perhaps this role, like many others, involved a new title but not a new job description. How many companies have a Senior Associate Somethingorother who was given the title mostly to justify a higher paycheck because they’ve been there so long? In this case, you’re not innovating; you’re perpetuating existing bureaucracy. Don’t string the person along with a false sense of hope.
    • Maybe there’s just too much tactical work that needs to be done. If that’s the case, and you move ahead and hire someone for a strategic role, all you’re doing is reeling them in with a bait and switch. Don’t do that.
  • If your strategist isn’t given any guidance or direction, then you can’t expect to get much out of the role. Yes, some degree of autonomy is necessary – and, to reinforce the first point, you can’t innovate inside a rigid box – but you need regular check-ins (or at the very least a set of requirements and expectations) to guide their work. This is especially true if you’re bringing in someone who’s proven in your subject matter but new to your industry vertical, or vice versa. Simply saying “We’re trying to be like a startup” won’t cut it.
  • If you confuse strategy development and product development, there’s a good chance you’re going to hire the wrong person. These require different skill sets, not to mention different ways of thinking and approaching a problem. If you’re in a rush to fill a role, step back and figure out what you truly need. Simply putting a body in a seat rarely succeeds.

(OK, So I *Might* Not Be An Expert…)

I think each of these problems is solvable, to a degree. But before offering solutions, three caveats:

  • I’m not a recruiter or hiring manager (and likely never will be). So there’s a chance I don’t know what the hell I’m talking about. I also recognize that you need to shoot for the stars in job descriptions. Noting that 50% of a job is wrestling with an home-grown and obsolete content management system, or that 40% of a job is sitting in meetings that could have been emails, surely won’t bring in top candidates.
  • It’s entirely possible that I didn’t like or succeed in my content strategy roles because I’m simply not cut out to do that type of work. I operate best when I have a clear assignment, objective, and deadline. Strategy obviously is more fluid. Sometimes I can work with that; sometimes I can’t.
  • Two of my three recent roles were in conference production. I learned the hard way that I really, really don’t like that work. The expectations of the role, coupled with how the work tends to be done, is a stark contract with how I prefer to work and am motivated to work. I’d like to think it’s not clouding my judgment here, but I can’t promise that it’s not.

Four Possible Fixes to Your Content Strategy Conundrum

Now that that’s out of the way, let’s talk about how to try to fix these problems.

Rigid processes. Don’t hire someone to change something that’s already firmly established, whether it’s an event that’s already been planned or an editorial calendar that’s already full. A strategist can have minimal influence over something that’s already set in stone, and trying to change what someone else has already created is bound to lead to conflict. Instead, put a strategist to work on new projects – or don’t hire them at all.

Too much tactical work. In one sense, there’s a simple solution: Hire someone who will do, and is expecting to do, the tactical work that actually needs to be done. This points to a bigger issue, though: What do you need to fix? Are the Big Ideas really not there – or are they there, just not trickling down into your finished products? In the former case, a strategist might help, but you also need to explore why you’ve been missing the Big Ideas for so long in the first place. In the latter case, you don’t need a strategist; you need an experienced manager of products, people, or both. Again, these are different roles with different skill sets.

No direction. The temptation to hire a strategist and send them on their merry way to concoct business-changing ideas is great. But, let’s face it, that’s not how work gets done (unless you’re a tenured professor or inventor). A strategist needs to know where to focus – new or expanded markets, new clients, new content types, etc. – along with when, how, and who to coordinate with to begin execution. Arguably more so than with any other employee, set clear guidelines and milestones for specific tasks to be done. Establish a clear reporting structure as well. “Dotted lines” to multiple managers will only add to the confusion for the strategist – and it gives managers a valid reason to pay less attention, since technically they’re not “in charge” of the strategist.

A need for product development, as it turns out. If the aforementioned Big Ideas aren’t there, but your company knows how to turn ideas into reality, then a full-time strategist won’t help you. Because – here’s a feel-good moment – you actually know what to do! You just need a nudge. Hire someone on a freelance or contract basis to hand you a polished idea and then run with it. Yes, there are a lot of details to work out, but keeping a full-time strategist on your payroll to do work that you know you are better at managing isn’t going to help your business. You’re going to be overpaying someone to do a job that, most of the time, isn’t really what they signed up to do.

Let’s Think About It

While I’m happy with the direction that my career has taken in recent months, I’m also a bit sad that my content strategy roles didn’t pan out. I liked my coworkers and managers, and I appreciated the work that we were able to accomplish together.

I don’t think my experiences entirely reflect the shortcomings of the places I worked. I think it’s part of a larger trend: Content companies think they want a single strategist, or even a team of them, but their true need is a bit different, and they haven’t taken the time to explore what (or who) will best impact the business. (It’s not unlike data analytics – everyone says they want AI, but really they just need better business intelligence.)

I hope these rambling thoughts are helpful for anyone who’s either planning to hire someone for a content strategy role or looking for a job with that type of title. They aren’t easy roles to fill, or jobs to do, and I hope we can all give them a little more thought as we work to create better content.