Debbie Oster: Messaging Strategy, Marketing Leadership, and Agency

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Why do smart business owners keep treating marketing like an execution problem?

This episode of The Business Owner’s Journey brings together host Nick Berry and guest Debbie Oster, a leading messaging and marketing strategist.

They dig into how leadership decision-making impacts messaging strategy, why crystal-clear client profiles are the backbone of effective B2B marketing, and what true marketing leadership looks like behind the scenes.

If you’re a business owner, CEO, or marketing lead looking to reduce guesswork and create marketing that actually supports business growth, this conversation will challenge you to think bigger and act with greater intention.

What You Can Learn from Debbie Oster

Better decisions lead to better marketing. Debbie shows how getting clear on who you serve, what you’re building, and what actually matters in the business makes marketing easier to manage. When leadership is aligned, teams stop guessing, priorities become obvious, and strategy stops changing every quarter.

That kind of clarity creates consistency, and consistency drives growth.

How Messaging Strategy Depends on Executive Decision-Making

Are your marketing problems really execution issues, or is there a decision you’ve been avoiding?

Debbie explains that most messaging struggles start with unclear leadership decisions. When goals aren’t defined, when target customers keep shifting, or when priorities change every few months, marketing has no stable foundation to build on.

To prevent those issues, Debbie advises that you decide who you serve, who you don’t, and what the business is trying to accomplish. When those choices are clear, messaging gets sharper, teams move faster, and results become more consistent.

What a Focused Ideal Client Profile Does for B2B Marketing Strategy

It’s tempting to believe that serving more people leads to more growth. Debbie challenges that idea. When you get clear about who you’re actually for (and write it down in a shared brand and messaging playbook), your marketing gets easier to manage. Messaging becomes more relevant. Sales conversations improve. No more channel-hopping or “shiny object” syndrome.

Focus creates consistency, and consistency builds results over time. When you know who you serve best, your time and budget go further.

How Marketing Alignment Reduces Guesswork and Improves Results

Is your team running in circles, or running the right play? Consistent alignment across leadership, marketing, and sales removes friction and confusion. Debbie breaks down common symptoms of poor alignment (like shifting targets, channel confusion, and vague success metrics), and how her workshop-driven approach turns chaos into clarity.

With a shared playbook and regular check-ins, everyone from founder to front-line staff knows what matters, what channel to use, and what to ignore. Suddenly, guesswork disappears.

Whether Your Growth-Stage Marketing Is Driven by Strategy or Fear

How often do decisions in your business come down to avoiding risk, rather than pursuing the best opportunity?

Debbie explains how growth-stage marketing decisions are frequently driven by fear of missing out rather than clear strategy. That leads to reactive planning, inconsistent messaging, and wasted time and budget.

A clear messaging strategy gives leaders the confidence to stay focused long enough to see results build.

Her Take on Marketing Leadership, Agency, and Positioning Strategy

What does effective marketing leadership look like when you’re not chasing scale for its own sake?

Debbie shares why she chose to build a focused, senior-led consultancy instead of running an agency. That decision required her to get clear on the kind of work she wanted to do, the level of involvement she wanted with clients, and what success actually meant to her.

It’s a practical look at leadership, ownership, and building a business that reflects your goals, not someone else’s version of growth.

Resources from Debbie Oster

Quotes from Debbie Oster

"The decisions are often, they're poorly made due to fear. If you're gonna be very clear on a really important decision, like who are you for? Who are you targeting? You've got to also decide who are we not targeting?" — Debbie Oster

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"If you are consistently changing who you're targeting, or channel hopping, that's a symptom you're missing something in your strategy." — Debbie Oster

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"Strategy is no good to you if it's just sitting in a Google Drive or in a Word document." — Debbie Oster

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"My ultimate goal was to have freedom. For me, that's I do want to do the work because I enjoy it, but I want to do the work that I love, which is strategy." — Debbie Oster

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"If something goes wrong or if something's not easy, it's not, that's not going to work or, I failed. It's, okay, how can I make this work? What's another way of doing it? How do I pivot to figure this out?" — Debbie Oster

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Transcript for: Debbie Oster: Messaging Strategy, Marketing Leadership, and Agency

00:00 Messaging Strategy Mindset Shift

03:21 Executive Decision-Making and Marketing Strategy

08:07 Building a B2B Marketing Strategy Framework

13:14 Symptoms of Weak Marketing Alignment

18:08 Debbie’s Business and Leadership Shift

23:01 Agency, Intentionality, and Marketing Leadership

24:37 Messaging Strategy Resources and Next Steps

Debbie (00:00)

I think what I've learned over the years is the decisions are often, they're poorly made due to fear. if you're gonna make, if you're gonna be very clear on a really important decision, like who are you for? Who are you targeting? Who are you gonna spend all of your marketing effort on? You've got to also decide who are we not targeting? Who are we

not going to go after, what are we not going to spend time and money and effort on? And it's very difficult for any business owner or executive to make a decision like that because it's an opportunity cost. You know, they have to weigh it okay, is this the way to go or is this the way to go? Because we can't go all the ways, And that's scary for people.

Nick Berry (00:37)

Mm-hmm. Mm-hmm.

Nick Berry (00:52)

Why do business owners keep diagnosing marketing problems as execution issues? What if the real constraints, just a lack of clear decision-making at the top. Debbie Oster is a messaging and marketing strategist for growth stage B2B founders. She's also a former business partner of mine and someone that I still work closely with and rely on. I wanted to have Debbie come on the show, not just because of how she understands strategy.

but because of the work that she's done to grow herself as a leader and how that has unlocked her potential as a marketing strategist.

Debbie explains how leadership growth sharpens messaging strategy. What separates marketing strategy from tactics? Why unclear business goals sabotage B2B marketing strategy? Whether your ideal client profile is fear-based or focused,

her take on decision-making at the top in a business, the best and the worst ways to build marketing alignment, and how high agency changes your effectiveness as a marketing leader. Enjoy this episode with Debbie Oster.

Debbie (01:44)

in any business, when you're trying to get very clear on what tactics you should be doing, what kind of channels to be using, it all is gonna go back to some really important core decisions that have to be made at the executive level. And that kind of starts with like, what are our business goals? What are we trying to accomplish in the business? Whether that's,

your revenue growth or customer retention launching a new product, what are the core things that the business is trying to accomplish over the course of the next one to three years? And then from there, you can, that'll help, you you to align your marketing efforts to that. So what are you trying to accomplish? Who's going to help you do that? what are the marketing things that you need to be?

focusing on in order to do that and that kind of leads to a bunch of other decisions you need to make from a marketing perspective. So that's what I mean when I say that. It really it starts with decisions, important decisions that have to be made versus just jumping into the tactics.

Nick Berry (02:44)

seems like those are decisions that are made maybe really poorly a lot of times, answers that are just not that good of answers. They're really not good enough to do everything else well.

Debbie (02:55)

I think what I've learned over the years is the decisions are often, they're poorly made due to fear. So, if you're gonna make, if you're gonna be very clear on a really important decision, like who are you for? Who are you targeting? Who are you gonna spend all of your marketing effort on? You've got to also decide who are we not targeting? Who are we like?

not going to go after, what are we not going to spend time and money and effort on? And I think in my experience, it's very difficult for any business owner or executive to make a decision like that because it's like an opportunity cost. You know, they have to weigh it like, okay, is this the way to go or is this the way to go? Because we can't go all the ways, right? And that's scary for people. That's scary as a business owner, as an executive whose job

Nick Berry (03:39)

Mm-hmm. Mm-hmm.

Debbie (03:48)

you know, is based off of it being successful or not, you know?

Nick Berry (03:52)

Yeah, because it does feel like you're, cutting yourself off from.

some of the potential, but that's not the case.

Debbie (03:57)

Mm-hmm.

Yeah, I mean, you're opening yourself to more potential, when you really hone in on like, who are we going after? Like, you're opening up more opportunity for your business than if you're trying to go after five different segments or people

Nick Berry (04:15)

So what was it that defining moment whenever you had that shift, that realization that it was…

these aren't execution issues. It's that lack of clear decision-making. did your epiphany come from?

Debbie (04:29)

think it kind of happened over years of working in marketing agencies and then working one-on-one with CEOs and founders of small businesses and having these conversations with them over and over again about the same things and realizing like they kept coming to me saying, want to know, how are we going to measure success? How are we going to measure success for our marketing efforts?

I could say what I thought they wanted me to say, but I kept realizing like, this shouldn't be this hard. And it was so hard because as the marketing leader, I wasn't privy to what they were really trying to do in their business. And without really understanding that, I can't do my job well and I can't align our marketing efforts to their business goals. So I kind of had to like back it up and start having these.

somewhat uncomfortable conversations with these business owners because they don't always want to tell you, you know, how much revenue they hit and what they're hoping to hit and what that's going to take. So you just kind of, and you taught me this when we worked together in the past, but you got to be, you got to get comfortable with having these uncomfortable conversations. And I think that's just kind of happened for me over the last probably three to four years, especially the more of these conversations I've had.

Nick Berry (05:48)

Are you getting more comfortable? Are they becoming less uncomfortable for you?

Debbie (05:53)

They are. I mean, they could still be uncomfortable, especially dependent upon the, the person you're speaking to. But, but yeah, I mean, it's like anything else. The more you do it, the more comfortable you get doing it, you know?

Nick Berry (05:59)

Mm-hmm.

And I think in those cases, so they may not be withholding information intentionally. They may not know how to answer the question well or well enough. going back to when we started working together in my case, there were things where I may have, there were answers that I knew that what I had were not good enough. And I could tell you that there were other answers that I did.

didn't know if they weren't good enough, that I would not have been able to tell you that definitively. I definitely didn't intentionally withhold any information, but there probably were things where I just couldn't give you the information that you might've wanted.

Having a conversation with someone like that, being able to kind of get through to them and them realize like, you're on my side, right? So you may be picking me apart, trying to find information or even questioning something that I felt like didn't need to be questioned. But you're doing it for the greater good. And that's why I had you there. That's why they have you here is because you're willing and able to do those things. And then I would think that would make

a lot of people much more comfortable and open to sharing and having those conversations. we're on the same team here, right?

Debbie (07:19)

Mm-hmm. Yeah, and that's a really good point. So it's like a therapist, as another example. They're trained to ask the right questions to pull the information from you that they need in order to help you, right? So as a marketing leader, I've learned over the years, I'm the one responsible for asking the right questions. Because it's…

every business owner doesn't necessarily know these things and how to like get into the nitty gritty of doing really, you know, really good marketing because that's not their specialty. Their specialty is running a business, right? Being an entrepreneur. So that's something I've had to learn as well as like asking the right questions and being able to clearly articulate why I'm asking them and how it's going to help us with their marketing.

Nick Berry (08:07)

when you run into a situation where a leadership team or leaders don't have the decisions made that need to be made, they don't have the information for you that is needed, what are you doing to help guide them through that?

Debbie (08:20)

I mean, it's basically like whether it's a one-off conversation or a team workshop where we gather the salespeople, we gather the marketing team, we gather the leadership team, and we talk through what are we trying to accomplish this year. In the next 12 months, what are we working towards? And we decide that. And then from there, we decide, OK,

who is our best audience, who is our ideal client profile, who do we wanna target? And that might have some segmentation in it, but ultimately, we're all getting very clear on this is who we're for, this is not who we're going after. And then from there, we figure out, okay, now we know who we're going after, this is how we're gonna speak to them. This is the messaging we're gonna use across sales and marketing, customer service, and then…

Then you get into, where are they? What channels are we using? What are the tactics? Budget, like all of the other things that people associate a marketing strategy or plan with, we'll follow. But first and foremost, what are the business goals? And then who are we going after? And then kind of setting everything up based off of those decisions.

And we have, so I specifically use what I call my brand and messaging playbook, but it's to help people make those decisions and document them. So everybody's on the same page. Everybody's working off the same playbook. They can get really clear on how the brand's gonna position itself in the market, who they're targeting, how they're gonna message to them so it attracts them, what channels they're using.

That's a tool that I use with my clients typically.

Nick Berry (10:04)

Okay, and so, that tool is kind of like, if I'm understanding the frame, basically it would be like the framework behind what you just outlined, the steps that you go through.

Debbie (10:14)

exactly.

Nick Berry (10:15)

Okay. then, so then it's captured. essentially their marketing strategy and goals. And so then do they go into a, like a planning or

Debbie (10:21)

Yep.

Nick Berry (10:25)

sequence or cadence with you or like what, does it live on from there? the thing that I'm thinking about is like we've all done that. Let's capture, let's put a strategy on paper and then put, you know, it goes on the shelf and then it's there.

Debbie (10:38)

Mm-hmm.

Mm-hmm. Yeah. I mean, in an ideal world, we're creating this playbook, you know, collaborating on it collectively with the rest of the team. And then it is in a place that is consistently revisited and refined as needed over time. You know, with my client specifically, like, we do quarterly planning. So every quarter, we're revisiting this. We're making sure that everything, you know, still holds true. And we ensure that

everything we're doing is working off of this playbook, you know, can be tied back to it directly. And if, you know, say they just want the playbook and they're going to go on, you know, on their own, like the goal is that I help them to understand that this has to be revisited regularly. This is a living document. know, strategy is no good to you if it's just sitting in a Google Drive or in a Word document, you know, that

people look at once a year or whatever it is when they need a little bit of help with some messaging. I this is something that you should, I say it's like the Bible. Like this is your marketing and sales, everything that they do should be based off of this information that we've decided together based on your overarching business goals.

Nick Berry (11:57)

Yeah, it's that's where you've captured your intentions. The priorities are set there for things that we're going to use to decide what we do every day and week and month in the short term.

Debbie (12:10)

Yep. That's the hardest thing with businesses that I've seen is, let's just try this. Let's try this. How about we try this? You know, it's like a, I feel like it's a conversation that gets brought up almost every month with teams. And I just, I watched it time and time again, and it's really having a negative impact on their marketing results because they're not being consistent for long enough.

And so they're constantly restarting and that momentum has to rebuild. And then once you get kind of on the cusp of like, hey, this is probably going to start gaining some traction here. They're like, no, it's not working. Let's let's try something different. And then they restart again. mean, it's it's just so common. I see it all the time. And then on the flip side, I see when you are consistent, when you stick to your guns, you come up with a strategy. You know, this is what we're doing. This is how we're going to do it. So we're speaking to.

and you are consistent with it, it does work and it does have a compounding effect. You just got to give it some time to gain traction and momentum and let the results start to happen.

Nick Berry (13:14)

So tell me about some of the symptoms. What I hear you describing there, we could think of that as like the entrepreneurial ADHD, or maybe it's somebody who didn't have just expectations weren't clear, it could be the lack of a strategy.

what are some of the symptoms that occur in a situation like that? So somebody who's listening can kind of self-identify, like, okay, this is more likely the situation that I'm in right now.

Debbie (13:40)

you

Mm-hmm. Yeah, I'd say some of the top symptoms one is Constantly changing who you're targeting so, you know jumping from this is this is my ICP to know This is my ICP to know this is them I'd you know, if you're doing that Every few months every year. I mean, there's something you're missing something another symptom is

You're posting to LinkedIn regularly and then you decide, nah, I'm going to jump on Instagram. actually, I need to be on Facebook. No, let's do TikTok because everybody's on TikTok. We should probably jump on TikTok. So just jumping like channel hopping and not staying consistent on those channels. Another symptom is not knowing your numbers. So if you are regularly engaging in marketing efforts, but

You don't have like your North Star, your KPIs, your metrics that you're monitoring on a regular basis and making decisions based off of those metrics. It's likely you don't have much of a strategy occurring because strategy in itself is something that's you have to measure it or you can't improve it. You can't adjust it. You don't know if it's working or if it's not.

Nick Berry (14:56)

situation is familiar. It's really easy to recognize when you're on the outside looking in, but when you're on the inside and, and it's, and you're going through it, it doesn't feel like there's this big void, you feel like you've got there just so many things. It probably feels actually like the opposite of a void.

It's because you don't have something to filter by. there are too many things, but that's, you know, the benefit of a strategy is it gives you something to filter things out with. So then you have, it's a lot clearer, you know, once you're able to eliminate all the things that are not even in play, then you've got a short list as to what the actual options are for the, uh, how you're going to do something, what the tactics that you're going to choose.

Debbie (15:20)

Mm-hmm.

Mm-hmm.

Mm-hmm.

Nick Berry (15:46)

And

then, I mean, I think it's challenging enough in that situation, right? When you are able to filter, when you're in the trenches. So it's just probably not glaringly obvious to someone when what they're missing is a strategy. For me, where I learned to become really sensitized to it is when I feel like I'm always missing the basis for a good decision.

If I don't have that, know, like I've got to zoom out and figure out like what's the big plan here? When I'm constantly, when I feel like I'm almost guessing a decision or I'm missing some critical information, like that's, that's when I know I can make the, I can flip a coin all day long. I'm not going to get any closer to the end goal until I zoom out. We need a strategy and then we can go forward.

Debbie (16:35)

Yeah, and that's a really good point. If you've got a strategy in place, anytime you get that, I call it shiny marketing object syndrome, you're like, we should try this. You can go back to the strategy, look at the goals that you've laid out for yourself and say, will this thing

Nick Berry (16:47)

Mm-hmm.

Debbie (16:57)

in some way help me get closer to the goals that we've set, you know, and that this strategy is based on. Whether, directly or indirectly, because marketing's got all these nuances to it. whether it could help with brand awareness or it could help with actual lead gen, you can think about it in kind of different ways. But if you can clearly say, yes, this can help.

it's probably worth considering. But if right away you can say, that's really far from helping us get to the goals we've outlined, then file it away in an idealist somewhere for a later time. You can waste so much money and effort and time chasing all these shiny objects.

and you just end up in the same place. ⁓

Nick Berry (17:47)

Yeah.

I talk a lot about like answering the question, how do you resist shiny objects? How do you know what to focus on? Strategy. That's the answer. Strategy is what tells you what the priorities should be. Benjamin Hardy was a guest a few weeks ago and he talks about this a lot with science of scaling. But part of our conversation centered around using strategy, what to say no to.

It's just, it's the thing that lets you filter so much of the stuff out with and, the game, it becomes, I won't say easy, but it's a lot simpler. It's more feasible when you can reduce the options in front of you down to only the ones that are actually material. The only ones that matter. And then that kind of puts into perspective how much of a disadvantage you're at when you don't do that filter and you.

Debbie (18:28)

Mm-hmm.

Nick Berry (18:36)

have all the options in front of you or all the options that exist. It's like, talk about guesswork. That is an impossible game to win.

Debbie (18:39)

Mm-hmm.

Mm-hmm. Yeah, it's like trying to find a show on Netflix. I can tell you how many times I set out to find something and like after about 30 minutes of just scrolling because I'm overwhelmed. I'm like, all right, I'm done with this. I'm just going to read a book.

Nick Berry (18:48)

There you go.

Yeah.

There you go. Too many options.

Debbie (19:03)

Yeah

Nick Berry (19:03)

your story with your business is one that I think is interesting and there are a lot of lessons that you can share there. So let's talk a little bit about like your business and where you've gotten to. Before we go into that, just for the audience. So I've talked about some, my business partnerships and people that I've worked with, Debbie and I have been

business partners in the past. actually, so we hired Debbie as our fractional CMO for one of our companies in 2021. And then we, outside of that, we partnered together in early 22. It may have been in the late 21, but we were going to start and build this agency. And then.

Debbie was the operator and so, was her, her ship to run and her pretty early on, I think it became clear to Debbie that she didn't want to do agency. It was more building the business for her as a solo and which is, one of our outcomes from the beginning. if this has to be built around your vision. So.

whatever shape that takes is totally fine. And so we unwound the partnership after a couple of years and now Debbie's gone on and is doing really well. She's built the business that she was envisioning. So that was the purpose from the beginning. But it just looks different from what we originally thought that it would, but that's okay. What matters is that that's what's happening. So.

That's a little bit of a different path from what I think most take and which is why I think that it's really neat and interesting and insightful for you to share.

Debbie (20:40)

Yeah, mean, thanks for the setup because that was, I think, helpful to have that background. yeah, I mean, I really thought I wanted an agency, you know, after working at agencies and having the skill set that I had and having all the experience and various roles of the marketing function, I was sure that I could do this well.

And especially with a partnership like, you know, with you, like it just felt like I had all the parts I needed to make it successful. And then, you know, as just time went on, I just realized a few key things that would have been kind of non-negotiables for operating an agency. Like I have to learn to manage people. And, you know, I have to be, I have to have a,

a good amount of clients if we wanted to, you know, generate enough revenue. And, you know, so those are just a couple of things. But I realized real quickly, like, wait a second, this is kind of the opposite of why I wanted to go out on my own and start a business. Like, my ultimate goal was to have freedom. And I know that that's a common theme with business owners. But for me, that means something different. You know, for me, that's I do want to do the work because I enjoy it.

but I wanna do the work that I love, which is strategy. I enjoy talking to my clients. I enjoy solving big marketing problems, but I also don't wanna work five days a week and I wanna take vacation when I want. And I don't wanna just sell the business one day to somebody else because I take pride in the outcomes that I create for my clients. And I didn't wanna just hand that off one day. So.

Yeah, that kind of like led me to the decision to bring it back to like a solo one person, one woman show.

Nick Berry (22:33)

so what I heard you describing there were your goals. Like once you got clear on the goals that you have, and really like in that case, some constraints, right? You didn't want to have a staff reporting to you. You want to do a certain type of work. You wanted it to be direct. And so we knew like, okay, we were going to have to shift our strategy to account for that. And so that's just, it's a different.

This is going to be a different machine than we originally thought we were building, but our overarching purpose was to build the thing that you wanted. that's the purpose of having those goals and how you apply those to creating a strategy that you've been able to execute. I think it was pretty easy to tell the difference immediately once you became clear. You knew what you wanted to do.

Debbie (23:27)

Mm-hmm.

Nick Berry (23:31)

So was easy for us to figure out how to go about doing it. And you've been on that path and it's been going very well,

Debbie (23:33)

you

Yeah, yeah. And I do think, you know, the process that we created, the way we worked together pretty early on was what helped us to get to that decision sooner rather than later. You know, like we set up these level 10 meetings and the way we were doing things and how we were doing quarterly business reviews and yearly planning and that

we were having those uncomfortable conversations on a regular cadence and we had our numbers we were measuring and we had our goals outlined. And those were the components that I think helped, I know me specifically, get to that decision sooner. Like, okay, I don't want this or this or this. I think I want this, this and this. And that kind of helped come to that final conclusion of, I think this is gonna be like a

me being the sole operator and that's just how this is going to have to work in order to achieve these things that I've set out to achieve.

Nick Berry (24:37)

It became clear enough to you that you could pivot with conviction. that's we did.

you mentioned the episode about leadership intentionality and the power of personal agency.

Debbie (24:50)

Mm-hmm.

Nick Berry (24:51)

What is it about that episode?

Debbie (24:52)

Well, it very closely mirrored a lot of conversations we had when we were partnering together. I still talk about intention and agency, having high agency really frequently, not only through internal dialogue, but with conversations with peers and friends and family, because I just think it's really important.

And I think we talked about this a little bit a week or two ago in another call we had together with some of our peers. But just leadership in general is being able to, solve problems and to be able to take in everybody's perspective, like all parties that are involved. And that was something that, until we worked together, I hadn't really thought about.

You know, like I'm always aware of how are people feeling? How do I want to make them feel? But it's a lot, it goes a lot deeper when you get into the subject of, you know, leadership and intentions and agency. And so that's, that's why I enjoyed that episode. It reminded me of a lot of conversations we've had in the past. And I think those are some of the biggest lessons that, you know, I learned from you as a leader.

and how to be a good leader.

Nick Berry (26:04)

Well, thank you. appreciate you saying that. So the reason that I wanted to ask you about it is because I feel like during that process of you, when you got clear and then decided to make the pivot and go from building an agency to building a solo business, your leadership took another step upward. Or there was an unlock or you shifted gears.

and I think it had to do with the conviction behind the decisions and whether it was knowing on your part or unknowingly just the corresponding actions that you then were willing to take and how well things have gone for you since then. getting clear is a great thing.

but you also have to have the agency to move forward and take action. And so I think that was noticeable with you. And I think it's been noticeable since then because we're talking about something that's been a couple of years. that's how you've been since then.

Debbie (27:04)

I would say that in order to be successful in any kind of business, whether it's your solo operator, you work for somebody, you're managing people, or I'm not saying work for somebody, but your partners, whatever that is, if you own a business and you're operating a business, no matter the size, you have to know what your intentions are.

You have to know what your goals are and you have to have agency in and say, if something goes wrong or if something's not easy, it's not, that's not going to work or, I failed. It's, okay, how can I make this work? What's another way of doing it? Or how do I pivot slightly to figure this out? Like, that's something that has, I feel like shifted in me in the last couple of years and has made a drastic

difference in the way I think about things, the way I operate with my clients, the way I operate with peers, colleagues, just taking that ownership of like, okay, maybe this isn't gonna work out the way I thought it was or I intended for it to, but I'm gonna go about it a different way this time. that's, I don't know, that's probably one of the most important life lessons I think I've ever learned. And I do attribute it to

to you and working with you. was a big mind shift for me and it's had a positive impact on all parts of my life, not just business, but especially my business.

Nick Berry (28:35)

That's awesome to hear. Thank you again for saying that.

Debbie (28:36)

Yeah.

And my husband hears it a lot now too in

Nick Berry (28:38)

Okay.

You

your work cut out for you on that one. It's funny that the way that you described it, I think was fantastic too, because another, so Jason Feifer the editor in chief for Entrepreneur,

Debbie (28:43)

I think.

Nick Berry (28:53)

In our interview, he talks about adaptability and, and I think, and he describes it a lot like the way you just described where it's like having that realization that, okay, this thing, it's not going to go exactly the way that I had it mapped out, but, that can be okay. it doesn't have to be exactly the way I mapped it out. There are elements of it that I want to hold onto, but like where I can transfer that somewhere else I can.

Debbie (28:58)

you

Nick Berry (29:20)

I can do this thing in other places, or I can do other things that are like this one in certain ways. And it's just being adaptable. he, yeah, we had a great conversation about it he talks about it being one of those, he says the most important skill or the thing that separates the successful from the unsuccessful. it definitely plays a big part. So at the end of the day, it's kind of like your vision for what you wanted to.

Debbie (29:38)

you

Nick Berry (29:45)

wanted to build with the agency, for us to be able to call it a success, we didn't have to build the agency that we sketched out on our first draft. The one for us to be successful, whatever we built, had to meet a few criteria. And there are a billion ways that we could have met those criteria. We just had to figure out which one was going to work the

Debbie (30:04)

Yeah.

Nick Berry (30:07)

the agency part was taking ownership of fit of that and figuring out like you're the one that has to get clear on these things because we're trying to design it around you. And so, and once you did, you you brought those things to the surface, got clear on them, and then we're able to reorganize the strategy around that. And I mean, it's been.

absolutely the direction that you wanted to be going in. So congratulations on that and well done.

Debbie (30:33)

Thank you. Yeah.

Yeah. It's funny, know, it kind of circling back to our earlier conversation about marketing and working with CEOs and founders and having to have these conversations with them about what do you want for the business? You know, what are we trying to accomplish overall? Because

If you'd, and maybe doesn't have to go in, you know, they don't have to go as deep into their dreams for their personal life. But, you know, I just need to have like a good solid understanding of, they trying to grow this to a certain, you know, annual revenue and then sell it? Or are they trying to do this so that they can launch, you know, start a new product line? Like what, what are they trying to do so that I can build their marketing system and, and strategy to, to align with that, you know?

So yeah, it just kind of came full circle for me in our conversation.

Nick Berry (31:26)

And if when they can give you that information, then they can turn you loose. You can go make your magic. They can get out of the way, which as, you know, as the CEO, music to my ears, right? Like that's okay. So, leaders, if you're listening, this is how you set your CMO or your marketing leadership up for success.

Debbie (31:32)

Mm-hmm. Yep. Yeah, yes.

Yeah.

Nick Berry (31:51)

be decisive and get out of the way. Is that helpful?

Debbie (31:54)

Yeah.

That's music to my ears.

Nick Berry (31:58)

Yeah, everybody wins. mean,

so we're, of that's tongue in cheek, but there's also some truth to it, some of us don't mind being told get out of the way or reminded that we need to get out of the way. Not everybody wants to hear that, but it happens.

Debbie (32:06)

Yeah,

Well, and two, think there's different definitions getting out of the way. know, there's, hey, help me decide what the goals are. Here's a strategy. Do you approve? Now you step aside and you don't have to deal with anything unless it's a budget decision and we're going to bring you in, fill you in. Or it's, hey, let's figure the goals out, figure out the strategy. I still want to work close and stay close with you on this. Cool. But you're the decision maker.

You're guiding me here because this is your expertise and you have the knowledge. I'm here because I write the checks and it's my business and I want to make sure we're moving in the right direction.

Nick Berry (32:54)

I mean, like most working relationships, just getting clear on the expectations. I think there's a lot of demand out there for a marketer who's willing to come in and help elicit the it either doesn't exist or it's not clear enough. And someone who's willing and able to say like,

Debbie (33:12)

Okay.

Nick Berry (33:14)

This is not clear enough for us to do this well. We need to dig in here and work on this some more. And it sounds like that's what you're doing with the branded messaging playbook and kind of, and workshopping them through, so they have like a more clear, polished playbook to operate by.

Debbie (33:20)

Mm-hmm.

Yep, yeah. I mean, with that playbook, like they'll clearly on everybody, not just the owner, the CEO, but the sales and marketing support. They know who they're trying to attract, how they're going to attract them, where they're going to do it, what channels they're using, and what they're going to say to them.

in order to attract them and nurture them and convert them ultimately. it is literally, that's why I call it the playbook. It is like step by step,

Nick Berry (34:02)

that sounds fantastic. So where do listeners need to go? How do they get a hold of this?

Debbie (34:09)

Yep, so if you go to my website at DebbieOster.com, you can contact me. My email address is on there. There's a form you could submit. I also have a newsletter. I send a weekly email that talks about the kind of things we've talked about here, talks about marketing at a strategic level.

Nick Berry (34:30)

It recently talked about why January creates bad marketing decisions.

Debbie (34:35)

yeah, yeah, it's.

Nick Berry (34:37)

So DebbieOster.com and the

strategy vault is the newsletter. This will all be in the show notes. And then they can also contact you or schedule time to discuss the brand and messaging playbook.

Debbie (34:48)

call.

Yep, yep, scheduling a call with me would be ideal, but if they aren't quite ready yet and just want to chat back and forth via email, they can certainly reach out that way as well. Or on LinkedIn, one more.

Nick Berry (35:00)

Okay. Yes, you're definitely active on LinkedIn.

Debbie, thank for doing this. I appreciate it. And congratulations.

Debbie (35:07)

Yeah, thanks for having me.

Entrepreneur and business advisor Nick Berry's headshot on a dark gray background.

Nick Berry is an American entrepreneur and business advisor, whose track record includes founding, leading, and advising award winning small businesses since 2002. He has built companies in multiple industries, hosts The Business Owner’s Journey podcast, and created the Business Alignment System™ framework that helps owner-operators scale without burning out.

After his most recent exit he founded Redesigned.Business to advise and coach to other entrepreneurs and business owners who are looking for a trusted (and proven) advisor.  

Among peers, colleagues and clients, Nick has been referred to as 'The Anti-Guru', due to his pragmatic approach and principled leadership. He shares his thoughts, experience, and lessons learned each week in The Golden Thread newsletter.

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