Mastering Freelancer Management with Becca Breslin, Director of Creative + Strategy at Stanley Black & Decker

This in-depth interview is part of Worksuite’s ongoing series on Mastering Freelancer Management: Expert Strategies for Effectively Managing a Remote Talent Network. Download the full guide here, and subscribe to our YouTube channel to see the latest videos.

Becca Breslin
Director of Creative + Strategy, Global Campaigns
Stanley Black & Decker, Inc.

Becca Breslin is currently the Director of Creative and Strategy at Stanley Black & Decker, Inc. She is responsible for empowering teams to produce work that is rooted in strategy, brought to life by unabashed big thinking, and spectacularly executed. A designer by trade, somewhere along the way she fell in love with user research and developing briefs that inspire teams and make them want to run and get started…not run away and scream because they have a hundred clarifying questions.

She’s proud to have built award-winning campaigns and global teams from the ground up, and workflows that keep both clients and creatives sane so they can concentrate on producing the best work possible.

Let’s start with the easy stuff — about you. What do you love about your job when it comes to managing freelancers and external creative resources? 

I love the fact that there’s so much unique talent out there and that every brief might have its own very particular strategies and needs. You need to build that team to accomplish that, and it feels like compiling your ideal roster every time you get a project brief and saying, okay, what are all the pieces I need to accomplish this?

And sometimes that’s really fun to put completely wildly different people together too. And that’s where sometimes it’s really hard at the same time to find all of those unicorns and put them together and say, how is this going to accomplish what we need out of the brief? 

How do you match those ‘unicorns’ to the right projects?

I’m always a big fan of briefs because that’s going to be your measurement for success. So I think if you can start out and say, okay, what is our end goal, and then work backwards from there. And start to say, what are all the steps in the process that get us there? And sometimes that means you might need a different team for each step of the process too, right?

It might mean, okay, there’s some really big thinking that needs to happen here at the front. So therefore I’m going to. But this group of people together, and then when it gets time to like, how do I really tangibly start to bring those big ideas to life visually, tonally, that might be a different group of people, or it might be the same.

But I think it involves identifying what your end goal is and then what are all the steps along the way to get there. And that’s how you, you bring in those different people. 

In your experience creating scalable processes in-house for brands, what does that brief look like? Do you have a template or framework for briefing great work? 

Yeah. So I’ve worked with similar processes, I think, in every place I’ve been, whether it’s a smaller nonprofit or a larger company like Stanley Black and Decker.

But I’ll speak to just right now. The way our process works is we do have a brief “template” especially when we’re thinking about what we call our tier-one campaigns. And it’s a brief that very clearly identifies, 

All of your standards. But then there are some non-standards like, 

So it’s got all of these checklist items to accomplish for a successful project. And that’s what grounds every step of our process here. We start first with making that brief. It’s usually myself as a creative director, and our director of account management with our client, our internal clients, our brand marketers, and our product team. So we build that brief with them and then we go through a creative strategy phase, and then we go through creative development and then eventually creative production.

So you can see even in, I mean, as you know from your world, those are all three very different steps in the process. Right? And those just require different groups of thought and how people strategize and contribute. So it’s often for us, three different groups of people in our in-house creative agency that contribute to that.

Very true. And what are some other challenges you run into with managing freelance creative talent? 

I think one challenge is always just creating the clarity. What are we trying to accomplish first? But then once you get past that and you get to what you’re talking about — the people part — I think some things that are challenging are…

Our world is just different now. And I know every generation of creatives and people probably say that, right? But every brief I feel like I’ve gotten, I’m like, woof, I’ve never done this before! 

And I’m not fresh and new. Mind you, I’m by no means 40 years into my career, but I’ve seen a lot of projects and I’ve been in a lot of kickoffs. Sometimes you get a kickoff and you think to yourself, ‘I’ve never done this before.’ And sometimes, no one in the room has done that before. And that’s a challenge in that, how do I get all of the right people to help us tackle this? 

On the flip side, sometimes everyone in the room has done it before. And that’s where it’s also a challenge: how do I make sure I’ve got the right people in the room to bring fresh ideas and to make sure that this isn’t rinse and repeat?

And sometimes that’s where supplementing and bringing in people to complement your regular roster is really helpful too. Like we talk about it here as, Hey, we’ve got our roster of key people and we kind of organize our creatives into pods, if you will. Each pod is working on particular clients, but every once in a while, you’ve got to pull someone from the bench, just like you would in baseball like, hey, I’ve got a DH for a certain team that I play or a certain pitcher who’s there, right. Like you’ve got to pull in those key players. So it’s both: when it’s like something you haven’t done before, and something you have done before, you need to really think about your talent network. If that makes sense.

And is there a difference in how you move that work forward — how you check-in and manage that creative talent — depending on whether they’re internal or external? 

Yeah, I think there definitely is. I mean, I think one thing we’ve noticed with our internal teams, and I’d imagine other companies can speak to this, when you own multiple brands, right?

For us, we own a lot of the market share in terms of tools and outdoor. Sometimes people don’t even realize we own everything from, yes, Black & Decker and Stanley on our nameplate, but we also own DeWalt, and we own Craftsman, and we own Cub Cadet and Hustler. Some of these can be somewhat cannibalistic if you’re not careful, right?

For example, I could be working on something for Stanley, but the same audience could theoretically also be shopping for Craftsman, but we own both of those brands. So how do we make sure that we’re separating our creative? 

And when we have our internal talent, we spend a lot of time when we onboard people, educating them on the “swim lanes” as we like to call them — of those brands and how we make sure we’re setting both Stanley up for success and Craftsman up for success.

We give each brand differentiating things in the marketplace. That gets hard when you’re pulling in freelance talent who don’t have all of that background. So I think for us, there is that period of building a freelance bench that feels like an extension of our team. We can spend the time and energy and make sure that they have that education of all the brands that we own.

And even if you’re just working on Craftsman, you really have to be aware of everything else, not just our competitors. But also the brands that we also own, so there is a difference in that we have the luxury of our internal folks that I feel like they kind of know and breathe that every day. 

And then the external folks, we just have to make sure we’re doing our due diligence of making sure that they still have that same background and awareness of our portfolio that internal teammates do.

What would that dream onboarding process look like to ensure external talent gets onboarded with the same education as internal team members? 

It’s a combination of, I guess I’ll say different learning styles. For example, we’ve spent a lot of time and effort, probably a solid two years when I first joined building really, really great brand standards and making all of our brand standards follow the same format. To the point where if you pull up the appendix or the menu of one brand standard, it’s going to look like the order of the sections, everything is the same so that someone can really easily go back and forth and reference those two.

So we have the educational pieces that you need to get smart on our brands. So that is a dream part of the onboarding process is just having really great tools and resources for your people, whether they’re internal or external. But then I think as well, part of that ideal onboarding process is facilitating opportunities for them to experience it firsthand.

Because it’s one thing, to just read it and say, okay, I’ve seen a couple of creative examples. But it’s another thing to immerse for the next two weeks you know, every time there’s a DeWalt status meeting, our account team is going to be able to pull you in for a 30-minute Zoom here and there. Seeing it, hearing the conversation, right?

Copywriters are one of the most difficult examples for us. With designers, it’s a little easier in that, visually you can say okay, cool. I get the difference. I see the font family. I see the textures. I see the colorway. I can understand that. Copywriters, it’s tricky to understand, tonally, how do I really immerse myself in this?

How do I understand there’s a whole set of adjectives that we give to one brand exclusively, and we actually don’t allow this other brand to use because we want to create that differentiation? And that’s really hard to get from a brand standard, until you’re in a creative review and hear someone talking about it, and that doesn’t always happen.

So just the onboarding process of, ‘Hey, let’s do a deep dive on each of our brands for the next two weeks. It’s going to be a 30-minute Zoom here and there.’ 

Switching gears in terms of creative direction of all these brands and talent working on different projects – and specifically around budgets. How do you avoid things going down the wrong path, dragging out the scope?

Honestly, I have to give good credit to our account management team who wears dual hats of both playing our resource managers and our project managers. And they’re frankly just incredibly experienced and smart at assessing, for example, ‘Okay I know if I have this level creative and they’ve worked with this creative before, I can really grasp how long this is truly going to take.’

They’re really good at scoping. I think that’s super important. But I think the other important part is just being really strong communicators and sometimes being strong communicators also comes from developing that type of relationship with that freelance partner. And it’s got to be a mutual respect and understanding of, ‘Hey, we have to check in and let me know how you’re doing on hours.’

As simple as having that conversation. Yes. Having a tool to track it is one thing, but I think going beyond having the tool as your foundation, but then also being able to build that relationship and have a conversation about realistic hours and what’s going on with the project.

Can you say more about the relationship aspects with your freelancers? 

Yeah, I think as much as you can make freelancers not feel like freelancers. Again, we keep describing it as this “extension of our team” and we like to say here, it’s not a dirty word for us.

It’s not like there’s an in-house versus out-of-house. It’s, these are a team. Just really great, unique talents and levers that we get to pull as needed and building that relationship. Like any relationship, whether you’re onboarding somebody new to the company, it just takes time and effort, and you have to put in that time and effort upfront.

So, you know, as you’re doing that resourcing planning for hours, such as making sure that you’re planning for, ‘Hey, I want this person in a part of the kickoffs. I want them in all of these reviews. I want them pitching work.’ We let our freelancers pitch work. It’s not just that they do the work. And then we take it away internally and pitch it.

We’re really transparent to our clients in-house. ‘Hey, I have a great connection that I previously worked with and we want to bring them into this project.’ To the point now where they’ve asked us, ‘Hey, this is different. Do you have anyone in mind who’s done something like this before?’ 

And I think they appreciate that we’re being really thoughtful about doing what’s best for the project and the company and making sure that we’re rounding out our team accordingly.

Yeah, I love that. Not to put you on the spot, but what’s your number one piece of advice around managing a large creative workforce or setting up for scale in terms of your creative output? 

My number one piece of advice is to just be really aware of what capabilities and talents you do have and what you don’t. And that’s okay. And being really curious about finding the pieces that you don’t currently do well and owning up to that and admitting it. It’s so rare. That you have every single role that you need perfectly staffed with the level of talent that you need. That is an anomaly. Especially in-house. 

And we’ve even seen it and experienced it at agencies. It’s why you’re constantly staffing up and down according to clients. So I think if you can do a good job of holding yourself accountable to constant check-ins to say, Hey, what do what am I working with? What do I need? 

And always being prepared to quickly supplement things in to round it out according to the project need. That kind of awareness and agility will really be helpful. 

I’ll give another example with copywriting. And I think it’s evident with design too.

For example, if you have a really cool idea that comes to life and it’s an illustration style. And you realize, we don’t have an illustrator in-house, right? That seems like a really quick ‘get’ to see, ‘Okay, I need to supplement with this type of illustration.’ But it happens with our copy teams all the time too.

And I think we’re trying to always educate both our teams and our people, our creatives, that it’s okay if you don’t write humor and lyrical rhymes for headlines, right? 

We just had a scenario where we just released a huge campaign for Craftsman and we partnered with a really great agency, Colle McVoy, and we wondered to ourselves, ‘Who did they have in-house writing these jingles!?’

Yeah, our copywriters aren’t jingle writers, right? Because that is a craft and a skill that someone has honed over time. And we just had to be really honest with ourselves as we transitioned some of that work, and we’re doing it in-house to say what do we need to do to, to either upskill or be transparent that this is an area in which we need help — especially when it’s a niche skill.

You need to realize that this isn’t going to happen across all of our brands. It’s not going to fill 80 percent of someone’s time. How do we supplement with somebody to really help us do this? I’ve done a lot of things, but I’ve never done this.

One last question. What does the future of work mean to you? What are you seeing that you feel is going to be really important in the workforce?

Wow, that’s a big question, Zack. That makes sense as an ending one. 

I think that there’s always a lot of focus on innovation and moving forward and thinking about what’s groundbreaking and what’s next.

And I don’t disagree. I think innovation is super important. However, I think what we sometimes tend to lose sight of is the healthy balance with learnings that we already have, right? How do I take past learnings, whether they’ve gone well or not so well, and combine that with forward thinking and innovation?

And I think that’s kind of a sweet spot that sometimes we innovate for the sake of innovating, without even having a purpose for it yet. How do we constantly balance where we’ve been and how we build on it with being forward-thinking? 

I think it’s really hard to take action on this when our world is moving so fast, but I think one way is to have postmortems. For example, after a campaign has launched or after you’ve done an event or anything to really carve out the time to look at, 

It can be learnings about the work itself, or it can be learnings about the process.

But I think one actionable way to be both innovative and forward-thinking while not overlooking learnings is to carve out that time to reflect and look back. Let’s not just put our heads down and move on to the next thing. I think we need to take time to both celebrate the wins, yes, but also learn from how the heck we actually got there.