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9. How do you avoid mistakes when structuring your team?

Hiring the right people for the right roles can make or break a marketing department. Kyle and Jeff examine some of the struggles a marketing leader can face in hiring, and give insights on how to make the best hiring decisions possible.

Topics Covered

Common hiring mistakes and misconceptions

  • Hiring based on expectations (which roles & skillsets you’re “supposed” to have).
  • Hiring as a reaction (planning for the present rather than the future).
  • Hiring too early (look for what you can outsource rather than wasting a role).

How to hire effectively

  • Know what your department is for, what your goals are, and what that will look like day-to-day.
  • Use contractors, agencies, & freelancers to fill the gaps and test the waters.

Resources & References


(Primarily autogenerated, let us know if you see any errors!)

Kyle: Hello and welcome to unReactive, where we look to help marketing leaders reclaim their time and sanity by exploring the topics that keep us stuck in a state of reactivity. I’m Kyle Morck, and I’m joined as always by my co-host Jeff Reynolds. How’s it going today, Jeff?

Jeff: Hey, Mr. Kyle. I am fantastic. How about yourself?

Kyle: I’m doing well. Yeah. I’m excited. We have another listener-submitted question this week.

Jeff: Always a nice way to start off the conversation.

Kyle: So I’ll just jump right in here. We’ll get into the meat of it. The question reads, “I inherited a marketing team and I’ve been thinking a lot about team structure. I wonder if you all have insights from your experience working with various sized companies in different industries.” Obviously this question is a fairly huge concept, the way you hire and structure your marketing department.

There’s a lot of nuance that goes into that. It’s very dependent on your marketing budgets, all of those pieces. But I did think that from this question, it could be really helpful to focus on some of the big picture mistakes that we really regularly see.

Jeff: I think that’d be a great place to start. I would add that I think it’s interesting that he called out size as a difference, and I would actually say that size at least once you get past, sort of, the one person marketing team or maybe three person marketing team, size seems to have less to do with it than probably some of the other issues that we see.

That’s not the characteristic that actually shapes marketing departments because they’re so different regardless of size.

Kyle: Yeah, and what you end up with if you have a really large marketing team, you know, 25 plus, what you end up with is really a lot of small marketing teams that have that same issue, but it’s just in a silo within that organization.

Jeff: Yep. And I guess I’m also thinking about this: I don’t know if it has reached meme status, but that image that was going around, you actually shared it with me, that was somebody’s example of an org chart, their sort of recommended org chart for a marketing team. And my, I can’t remember exactly, but there were like, you know, you had the CMO at top and then there five or seven or so different sort of departments, you know —

Kyle: Like pillars within it.

Jeff: There you go. And, I mean, it had thousands of likes, and I’m not even necessarily saying it was wrong, but it definitely wasn’t appropriate as sort of a prescription for most organizations.

It just simply didn’t fit the reality of how many organizations work, even though some may. So I, I guess what I’m trying to say is I think if you just saw that on LinkedIn, you’d be like, oh my gosh, I don’t have eight different department leads or whatever that report up to me as the marketing director, I must be doing something wrong, and that is totally not the case.

Kyle: Yeah. And we’ll get into the specifics of this, but really, inherent within that kind of org chart was all possible types of marketing that you could do. And the reality of the situation is that only the largest companies, if even the largest companies, should be doing all types of marketing.

Jeff: Yes, and if they do all types of marketing, chances are they don’t all flow up to the CMO. Like that neatly showed. So tell me, how would you categorize some of the issues that we regularly see when trying to design your marketing department?

Kyle: Thinking through this topic, there were three high level issues. They are all various levels of interrelated, but three areas that I would really be focusing on if you are doing hiring, looking at how you’re structuring your department to be really wary of essentially in how you’re approaching that

Jeff: So hit us.

Kyle: Number one, and this is very much relevant to that org chart example, is hiring based on expectations. And that might be the expectations of your company’s leadership or probably more likely it’s the pressure you feel from the idea of this is what a good marketing department is supposed to look like.

So when you see those beautifully laid out org charts that cover all possible facets of marketing, you aspirationally start to think, “Hey, this is what I need to be able to make my marketing department look like.” And you start hiring with that focus.

So diving into some specifics. What it comes down to, to me, is you’re focusing either too heavily on the marketing domains, or specific skills when hiring. So when looking at the domains, it’s amazing to me how often a marketing leader’s first hire is a social media person.

There’s a lot of reasons for this and some of those we’ll get into later on in this list. But when it comes to expectations, it’s just something that so many marketing leaders take as accepted fact. Like you need to do social media. That takes a lot of effort. So one of the first hires we need to be looking for is a social media person.

Jeff: Whether or not it’s actually having a large impact on the organization or is important in any way to the organization. So clearly, and usually, you know, mathematically we’ve talked about this, and I always feel like we’re sort of beating up on social media, which we don’t mean to. But I guess the reason it comes off that way is because many organizations over-invest in skills around that without any proof of return whatsoever. And so that is almost, by definition, you’re doing it based on expectations, not on return on investment.

Kyle: Yeah, because social media, to do it well is a highly, highly skilled enterprise. And when every company has a social media person the chances of them having that really highly skilled person is lower, and the chances of that being the right thing in the first place is already so low that you’re really just compounding it negatively, that you are almost guaranteeing that.

Dedicating a salary towards something that is not going to move the needle.

Jeff: Yeah, you’re just chasing the trends.

Kyle: And speaking of trends, like the other side of this that we see with domains, especially at SaaS startups, you see this tendency to start with hiring trendy roles. So when you’re in that startup phase, once you start hiring, you get your head of demand gen, your head of growth, your head of community, you hire all of those in close proximity.

And it always feels like it’s coming much less from a place of, “We’ve put the thought into it and we know that this is what’s going to achieve that growth that we’re looking for.” And more just keeping up with the Joneses of, you know, “If I’m going to be this marketing leader that I wanna be, I need to have demand gen operation.”

Jeff: Yeah, and there’s real consequences to that. I just ran into somebody today who told me the story of how she got hired at a company. For one of these sort of trendy roles, I’ll leave out the details. And within weeks, the company decided to do layoffs and guess what? Her position was eliminated. So, I mean, that’s ridiculous in my mind that, you know, clearly there’s a disconnect between senior management in this organization and then the marketing leadership who was hiring for the roles.

And so all I’m saying there is that, chasing trends is dangerous because at the end of the day, if you haven’t decided what matters to your organization and then hiring appropriately to your organization, then it’s going to lead to a yo-yo effect where you’re sort of hiring and laying off, hiring and laying off.

And of course that hurts your reputation and it hurts people.

Kyle: Real human consequences too.

Jeff: Yes.

Kyle: So the other angle of this, so you’ve got that domain side of it, but we also see regularly hiring based on skillsets. Oftentimes, you know, smaller marketing departments might be made up just of a designer and a writer. And obviously those skill sets are needed within marketing.

But when an organization starts making their hiring decisions based on those skill sets, it’s leading to a very production focused marketing department that if you have a designer, everything becomes a design issue, and you just end up being kind of naturally reactive.

Jeff: Yep. Everybody, you’ve basically ended up hiring a whole forest of trees and nobody’s seen the forest, right? And a lot of times in the real world, the marketing leader might even fulfill one of these roles. So like a lot of us grew out of some deeper skillset, whether that’s design or writing or customer service, client service, that sort of thing.

And what ends up happening is you end up shaping your marketing department to match your background and not what the organization actually needs.

Kyle: Yeah, that’s a great point. And hopefully the advent of tools like Canva and Chat GPT, which are going to continue to kind of devalue that technical work that we’ve talked about before, that is seen as marketing’s domain more because it was something that there were higher barriers to entry. Hopefully those tools and AI will make this less of a regular occurrence.

Jeff: Yeah, and I, I’m still a big fan of sort of the deep T methodology, or it could be a deep H for some folks. You know, this idea that you’re sort of a generalist, or at least within a window, you’re a generalist. You are on a spectrum. You may not be able to do everything, but you understand many things, but then you have a deep expertise or two that can sort of be overlaid like a Venn diagram to complete a team.

That’s a general way of thinking about it. But, you know, I was thinking about this today because well, I was speaking with somebody who is on the job hunt and I was thinking what employers actually want to hire. And, frankly, a lot of what we were talking through was the challenge that you just discussed, which is a lot of times, there’s a tendency to want to hire experts, specialists, but the other reality is that that’s not what most organizations need.

You know, they’re not big enough to have a collection of 10 subject matter experts.

Kyle: Yeah. And what I would add to that or kind of clarify from my side on it is that there’s a difference between a marketing expertise, ‘cause I think that there’s a lot of value in hiring marketing experts versus a skill expertise. Like having somebody that’s really, really good at design isn’t going to serve most marketing departments.

Because that’s nothing against designers. Like, you know, I come from a design background myself, but just being really good at Photoshop is not the most important skillset to a marketing department.

Jeff: Right, and I think that’s what I’m trying to say with this visual of the deep T or multiple Ts, is that you may be good at Photoshop, but you better damn well be also good at sort of the skills on the edge of that. So communication, being able to understand what customers need, being able to explain your ideas.

And that sort of makes up the top of the T whereas your design skills may be the thing that goes deeper in this metaphor. So I, I agree with you and it’s not to say that it’s not good to have expertise, right? You need expertise a lot of times to get the job, but you also need to develop the skills, the adjacent skills and then as as leaders, we need to be more open and intentional on who we hire to make sure that all these deep Ts can sort of weave together to make a mesh that actually serves our needs.

Kyle: Yeah, that’s right. Really gets us to our second topic because I think the real reason that we end up in that skillset focused hiring, this domain focused hiring is that we end up structuring our team as a reaction to something else. And most regularly, it’s a reaction to the workload of the marketing leader.

If you imagine how a marketing department naturally grows, you start with one marketer and they start to spend more and more of their time doing specific things. So it might be managing social media or trade shows. Then that marketing leader, when you’re looking to make your first hire, the tendency is to try to hire to get those time sucks off of your hands.

Jeff: Yep. So it’s like if trade shows are a giant pain, which they usually are for most folks, then the obvious next hire needs to be a trade show coordinator.

Kyle: Exactly, and there’s two issues with this. First is that there’s a good chance that the reason that you’re feeling like you want to get them off over your hands is because you feel like it’s not worth your time to be doing it. And if it’s not worth your time to be doing it, you should really be asking, is it worth doing at all?

That’s a really good sign to you that you’re probably not getting a return from it in the way that you should be. If you’re feeling like I’m wasting my time handling these things personally.

Jeff: That’s interesting. But there is sort of a difference there isn’t there If it’s, it’s valuable to the organization, but it just sort of needs a person who maybe isn’t as distracted by the other million responsibilities. So it’s more tactical. Does that make sense?

Kyle: it’s definitely possible, like, you know, obviously a marketing leader can’t do everything that needs to be done within marketing. I’m more saying that that’s a good sign of something that you need to reflect on before you make that higher.

Jeff: Love it. I totally agree. What else? You said there were two.

Kyle: The second one is that a lot of times marketing leaders look at those decisions as being just overflow of their workload.

So when you are looking at it as being overflow, you end up hiring marketing generalists and I’ve got nothing against generalists, ‘cause I really believe that a super strong generalist is going to be your most valuable employee, but most marketing departments aren’t in a place where they can recruit that top 10% of talent.

So hiring generalists just ends up getting you into trouble because I’m a big believer that a good leader should be hiring people that can do tasks better than they can. Really when hiring gives you the best value is when it’s, “Hey, this person’s so good at this thing that I never even have to think about it again because they’re better at it than I am.”

But that’s going to be really difficult to do when you’re hiring for a generalist, when you’re naturally trying to hire somebody that can do all of the things that you’ve done in the past and are just trying to move past, you’re not gonna get somebody that is really good at the things that they need to be really good at.

Jeff: Well, and in the real world, what that often translates to is a bunch of people sitting around staring at each other, looking for people to manage and boss around. But who can’t really do anything themselves, you know, and I don’t mean that as a negative against generalists either. I feel like I’ve become more of a generalist over the years.

But at the same time, I feel like, you know, at the end of the day, for me personally, my writing skills and, and some strategic skills, trump my generalist skills, right? The way I think about it is you have to be careful when you’re hiring generalists because generalism can often translate into “do-ism” which is exactly what you don’t want specifically on a smaller marketing team.

Kyle: Yeah, because your really valuable generalists are going to be able to show up in a room and seem like they’re an expert on whatever that topic is. If your generalists can just kind of barely hang in conversations about everything, then they’re not bringing a ton of value to the organization.

Jeff: I mean we’re using this term generalist, which is like a general term. You gotta be careful with that term, right? Because “generalist” could mean I just never developed any actual skills. Or it could mean what you just said, which is I’m an expert in enough to get through enough.

Kyle: Yep. The other piece that I would really caution around this topic is that you need to be really careful after you make a hire to protect them from being dragged into a reactionary role. Because even if you do hire an expert in one area with a really well scoped and reasoned job description, that matches your strategy exactly, if you don’t have a strong plan in place for how you’ll handle things like your social media or trade shows that are seen as this time suck, that doesn’t have that clear value, if those are still on the plate of your marketing department, then that new hire is going to end up getting looped into those tasks as a release valve for you regardless.

Jeff: Yep. That’s good stuff. So, to sort of wrap these first couple up, you identified two major issues, which is people hiring based on expectations and people hiring as a reaction to sort of outside forces. And you kind of went through the risks.

What else should they be watching for?

Kyle: The last one that I would be watching for is hiring too early. The other reason that we see marketing departments end up with a lot of generalists is because there’s not enough work in specific expertise roles to make up a full-time position. So you’re hiring for somebody that can do social media and design and your emails.

Anything like that because you don’t have enough work for, you know, just a dedicated email person or something along those lines and. I think it’s dangerous because marketing leaders of the future are going to need to become very comfortable with effectively outsourcing work to contractors. So obviously you and I, we come from an agency background, so there’s some bias there, but I truly think that a marketing department is going to have less and less need for that hands-on keyboard work that has traditionally taken up most departments’ time. AI, all of those pieces, you just have less need for people that can just produce things. So what that means is that you need to still have access to true expertise if you’re going to move the needle. And the easiest way to get access to that expertise is going to be using outside resources.

Jeff: Yeah, and you, you kind of mushed it all together, AI and all these other things, but I think there’s, there’s things worth talking about there. A basic one is that increasingly the world is templated and then sort of do it yourself, right? Like you don’t need to set up email templates or social media templates every week.

You know, so you need an expert to help you get that done once, or your CRM is another example. You know, you don’t need, yes, you need to maintain your CRM on a whatever, weekly, monthly, quarterly basis, but you don’t need to set it up and think through that. So you, you don’t need to hire a CRM expert, but there’s a risk if you don’t hire a CRM expert, then you’re gonna waste a whole bunch of time by having your copywriter trying to figure out the best way to use your CRM.

Does that make sense?

Kyle: Yeah, cuz it goes both ways. You don’t need somebody full-time managing your CRM, but if you don’t have somebody full-time managing your CRM, you can’t just let that overlay into just everybody’s job is to manage the CRM ‘cause then it’s just the blind leading the blind.

Jeff: There is skill in setting up a CRM. And believe it or not, your graphic designer or copywriter, whoever, might not have that skill. It’s a specialized skill. So investing in that skill. And then the other thing I’d say is that obviously with things like Upwork and, and 99 Designs or whatever are these different tools and agencies, you know, freelancer.com, and just the growth and boom of freelancing in general. You actually can get your hands on these experts and I just think, you know, there’s different skills that need to be developed to manage that, but it could be worth doing.

And I think the future is now as marketing departments being more like orchestra conductors and the people they’re conducting may or may not be full-time employees.

Kyle: Yeah, ‘cause the future of freelancing, I think is going to be a lot of the, smartest people in their fields are going to be going out solo and they’re going to be really hard to hire, which actually is a huge opportunity for the majority of marketing departments because now this extremely intelligent, strategic minded person is, instead of being locked to just one really well paying corporation, they’re gonna be somebody that you might be able to access a day of their time, a week of their time, whatever that might be, and get access to that knowledge only when you need it. And that’s a huge opportunity for marketing departments.

Jeff: But it requires a different mindset, and I guess that’s what we’re talking about. And sort of a little bit of a side note when we’re talking about this deep T idea and sort of building on what you just said, if you’re trying to get a job in marketing, if you can’t identify your T, if you can’t right now, say, “What would I freelance back to the company I wanna work for? What would I freelance as?” If you can’t answer that question, then you’re probably too much of a generalist.

Kyle: Yeah, that’s a great point.

Jeff: So I just think that’s a little sort of a measuring stick to ask yourself, have I developed the actual skills that make me valuable to a marketing team? And I guess one of those skills in the future, as is becoming an increasingly obvious, will be things like prompt engineer, or outsourced resource producer or, you know, manager, those sorts of jobs.

It’s not just marketing, traditional marketing creation skills that we’ll be looking for. Okay, so how do we deal with this? What should we be focusing on? If I’m not hiring too early, if I’m not hiring as a reaction, and I’m not hiring based on some other outside expectations.

Kyle: When it comes down to it, all of these issues are really stemming from one place, and that is doing your hiring, structuring your marketing department without a strategy in place. So if you don’t know what your department exists to do, where you want to go, and what tasks and actions are going to get you there.

It’s really impossible to structure your department in a way that’s going to effectively achieve results. So that’s number one, is you shouldn’t be doing any hiring until you know what you exist to do.

Jeff: Well, could I just add, that really is we’re talking about is really clear marketing objectives and sort of that strategy or path for how you’re gonna get there. Like you, you need to be able to articulate both those things. To even have a sense of what you were just talking about.

Kyle: Yeah, you need to know what your department is actually going to be doing day-to-day and start there like writing a job description for your hire should be so simple and clear to you because you know exactly what they’re going to be doing from day one. If you know that email marketing is going to be the thing that’s going to move your marketing forward, then really you need to be looking to hire the best email marketer you can find and let them loose to do their thing.

And that’s likewise, if it’s SEO, digital ads, community management, any of those things.You know, create these job descriptions. If that’s a mishmash of 17 different skill sets, that’s probably a sign that you don’t actually know what levers you can pull that are going to move things forward.

Jeff: Yeah, I love that. And then I think part of that, and of course you’re sort of zero basing it as if you don’t really have a team, but if you can still do a basic gap analysis and just say, “Okay, here’s where we’re trying to head. Here’s what we need to do to get there. And so here are the roles that need to be filled.”

And then the creative exercise as a marketing leader is to figure out how that puzzle comes together, right? Like reimagining roles that suit, they’re sort of custom built for your organization’s needs. Instead of saying, “Oh, I need a project manager,” and literally having no idea what that means or what they’re managing, you know which happens all the time.

Kyle: That’s exactly right. So the last piece of advice that I would give is, with every hire that you’re looking to make, you probably should start by using outside resources. So that can be a freelancer, that could be, you know, a contractor that you’re hiring with the intention of them becoming full-time, or it can be an agency.

And you should only really bring it in-house once it becomes financially infeasible, not to, you know, when you’re spending so much money on those outside resources that you are going to be making better use of that budget by bringing that in-house.

Jeff: I freaking love that. It’s, to me, what I hear when you say that is to check the ego at the door. It’s not about how many people you manage, it’s about getting the job done right. And you can do that by testing, basically doing a little pilot of a position or a role with freelancers.

Kyle: Yeah.

Jeff: And I mean, frankly, that could be even what seems like grunt work.

You know, you can find people, great people that are looking for flexibility in their schedule or other things to test out these roles and who may turn into your next hire if all things work out. So that’s great advice.

Kyle: Yeah. So I think to sum things up, what this really comes down to is as you’re looking at, you know, the future of AI, if you’re looking at recession, anything that are those big pressing issues that are facing marketers today. The core of a lot of those solutions and how you can plan for the future comes down to how you hire and structure your team.

So being really intentional about it is going to be one of the keys to set yourself up for success in the future.

Jeff: Yep. And I do think the future is a much more nimble marketing department, which probably stresses people out because right now they feel overloaded, but the source of that overload is likely not, in reality, that they have too few people. It could be, I mean, it is often that, but even more common it’s that you’re doing the wrong things in the first place.

You’re keeping everybody busy with things that are not the most important things.

Kyle: I think another way to think about that and thought experiment with it is, your hiring should come from success, that it should be, we’re doing such a good job at this, that we can do more of it at a bigger scale, and we’ll need more people to do that. If you’re sitting there feeling frustrated and feeling like you’re not getting anything done, then hiring is probably not the solution.

You need to be looking at what you’re spending your days doing and why that isn’t getting you the results that you’re expecting.

Jeff: Excellent. I have nothing to add to that.

Kyle: Thank you all for listening today. If you wanna get more content like this directly in your inbox, be sure to sign up for the unReactive newsletter at upMarketer.io. Thank you very much to the listener that sent in today’s topic. And if you have any topics that you’d like to hear discussed, please reach out to us on our website or social media.

We’d love to hear from you.

Jeff: Yeah. And make sure you’re following or subscribing or whatever the various, you know, apps ask of you.

Kyle: If you liked it, then make sure you sign up to listen to more. Thank you so much, Jeff.

Jeff: Hey, thanks Kyle.

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