Ashley Gross of AI Workforce Alliance and ChiefAIOfficer.com shares her specific strategy and tactics to solve the top 3 business problems every business experiences at some point in the business lifecycle.

Ashley Gross Strategy & Tactics

MKJ (00:00.888)

Hey, hey, CEO, Mischief Makers, MKJ here, and my incredible guest, Ashley Gross. Ashley, you ready to rock about strategy and tactics? My favorite, right? This is where the rubber meets the road. This is where, all right, what do we do? We’ve talked about all this great stuff, Mary, know, esoteric, yeah, mindset, blah, blah, blah. Now, what do I do? So let’s talk about what you do. You have helped so many people with AI. What…

Ashley Gross (00:10.33)

I’m ready.

MKJ (00:29.718)

If you can talk about a strategy, let’s say someone’s a small business owner and they’re looking at this whole AI landscape and they’re like, what the flip do I do? Jasper, what? Chat GPT? I mean, yeah, I can ask it a question. can write me something, but half the time it’s not right. What do I do? So first off for a small business owner, give me a strategy that they can think about, and then let’s dive into the tactics and the actual things they can do to use this to better their life.

Ashley Gross (00:56.337)

Yep. OK, so here’s the strategy. It’s very simple. Find the problem. Find the burning problem that you are experiencing this quarter. And not you, the business. What is the business’s main problem this quarter that you need to solve for? That is where I start my strategy off. Technology is only as good as its purpose and how good it was built. If you don’t know the problem, then you’re just kind of throwing AI in the shiny sticker effect on everything and hoping something sticks. There’s no strategy. Start with the problem, always.

MKJ (01:27.096)

Got it. So let’s say I’m in a small business and I’m looking at what I think the problem might be is I need more leads. So how, let’s die. Give me some problems and your diagnosis and the actual tactics people can use.

Ashley Gross (01:46.011)

Yep, so here are three business problems that every single organization I’ve ever worked for has, right? Lack of clean data without relying on third party tools, lack of insight into the customer journey, and then slow sales cycles, right? So those are the three problems I like to focus on because they’re painful and normally everyone is aware of them. Now they might not know that that’s the problem, but they’re feeling some of the after effects of one of those three problems.

Those are the three areas I like to start with. Now, my answer for once you find that problem and you diagnose it, where do you start? There’s already someone in your organization that is excited to take on AI. Give this to an employee that is in the trenches, they are a practitioner, they are doing this work. Because if you are a founder or a senior executive, the further up the chain you move, the less insight you have into the trenches.

And really, this is where AI implementation takes effect. So you need someone that is in the trenches doing work every single day. And they know the workflow. That’s the important part, because you can’t have human in the loop if you don’t know what that workflow looks like. So I would say look for the employees. It can be something so simple, such as putting a Slack message out and saying, does anyone want to form an internal task force, an AI task force? Call it whatever you want. And then in that call,

find the employees that are excited and they’re raising their hands and have them align with the founder. This is exactly what I did. I’ll just, I’ll give you the copy and paste playbook I had. I went to the founder and I said, what do you think the business’s main problem is? He gave me an answer. said, great, hold onto that and do me a favor. Don’t tell anyone else what you think it is. Then I brought in all the senior executives and the founder. And I specifically told the founder, don’t give the executives any pointers, right? So just the C -suite members and the founder and myself were in this call and I said, hey everyone.

We want to talk about what the business’s main problem is. And we’re going to go around and everyone’s going to tell me what they think it is. Here’s why I did this. If you take the senior executives and you put them in front of the founders, they become almost childlike. Where they have an open mind, they’re very vulnerable. They don’t want to have the wrong answer. They don’t want to look dumb. And that has to go immediately in order for you to feel safe to experiment. You’ve got to get rid of that mindset. So I purposely make them uncomfortable so that they’re willing to have an open mind.

Ashley Gross (04:03.749)

And so eventually someone’s brave enough and it starts this domino effect of everyone starts giving ideas. And one of two things happens. So one, the founder actually gets to hear from his senior staff what they think the problem is in a way that they’re not gonna be penalized for what they have to say. So it’s helping the founder, but it’s also helping the employees, because most of the time what the founder says is the issue is not what the senior executives are saying, which makes sense, because as you go further down the food chain, you’ll actually know what the problems are from those people.

MKJ (04:26.894)

Okay.

Ashley Gross (04:33.637)

So everybody agrees on what the problem is. Let’s just say it’s lack of clean data. So we’re like, OK, great. When we’ve had this issue before, senior executives, what have we done? And then marketing and sales, product, everybody goes around and they talk about, well, when we had this issue with our CRM and we weren’t getting good leads, here’s what we tried before. Here’s the metrics we used to test this. Here’s the timeline that we used to test this. This is the AI ROI, right? If we don’t.

pick the use cases where we know metrics and we know pre -AI ROI, we’re not going to be able to actually get good figures post -AI. Then after that call -ins, we’ve diagnosed the use cases that immediately are solutions to the problem. And we’ve only picked use cases to test AI with that we have metrics pre -AI for, and we’ve applied a timeline.

MKJ (05:04.172)

Yes.

Right.

Ashley Gross (05:20.967)

So then these executives go back to their teams and they say, OK, here are the use cases we picked. And usually there’s like 10 per department, right? We have not narrowed this down yet. In that call with the department, so you have marketing having their separate call, product sales, everyone, then the leaders of those departments are saying, here’s the list. Out of this list, what do you guys hate doing? What do you hate doing out of this list? What this does is, one, you’re figuring out what that specific use case is.

But two, you’re not threatening anyone’s job security. Because if you’re picking a use case and you’re allowing them to help you pick the use case, they’re advocating for themselves. They’re giving you insight that you probably didn’t have as a senior executive. And you’re automating tasks for them that they hate doing. So of course they’re going to be more willing and intrinsically motivated to try this out. Once you have that use case, apply a timeline, tell them the metrics, have bi -weekly 30 -minute calls.

where you bring every department together and say, hey, as far as this use case goes, what are we seeing? What barriers did we run into? What roadblocks are there? And then that’s how you actually get pilot projects off the ground. But you have to do it in that order. And you’ll notice like 90 % of that was communication. That’s really it, is internally aligning, communicating expectations, making sure those expectations are realistic, and then hitting the ground running and experimenting.

MKJ (06:29.281)

Yeah.

MKJ (06:37.714)

my goodness yes and look at that i love how you just logically lay it out i know we talked off mike about you the whole imposter syndrome very briefly but that’s where so many people get stuck it really is that fear but you you’ve taken that scenario and just logically broken it down into into its component steps.

Ashley Gross (07:00.22)

Yes.

MKJ (07:00.258)

So now take that, that’s beautiful. All right, anyone listening, if you are in an enterprise or a small business that has a team, a large enough team that you can apply that, run with it, go join this community, find more information, you will be the savior of the company if you do this. You will be. So now let’s take that and translate it into, let’s say, an entrepreneur with a small team. They don’t have, you know, these components, C -suites and all the employees.

Ashley Gross (07:17.222)

You will.

MKJ (07:27.618)

but they do have maybe a small organization where they have consultants or they have maybe a few team members and they use consultants, how can they translate that idea that you just laid out into more of an entrepreneur, real small, small business?

Ashley Gross (07:43.025)

So when I did my research, I found three reasons why businesses fail to start or three reasons why businesses fail to last longer than five years. We’ve all seen that really ugly chart where it’s like, business’s success levels and then after like year five to seven, it’s like, boop, like huge drop off. Those three problems are a bad business plan, lack of resources and knowledge, right? Or lack of finances. Those three problems seem very silly to me because if you know that those are the three reasons,

MKJ (07:56.898)

Yeah, go on.

Ashley Gross (08:12.859)

there shouldn’t really be, like you shouldn’t be failing for those three reasons. And so for small businesses, I always kind of put an emphasis on the founders and the board of directors if you have any. Everyone’s bad at something. So humble yourself. What are you good at? If you look at those three reasons of failing, what is the one reason that concerns you the most? That’s probably where you need to set aside some time to dig in deeper. So.

You know, when I was starting this business and I knew it was going to be formed around a community, I had never started a business around a community before. So was like, I need to go do some research on communities so that I don’t have a bad business plan. That was my first step was really analyzing what my skillset was and identifying what my fear was. Because when you are afraid of failing, that’s when you’re going to make mistakes. Everyone’s going to fail. And so knowing that uncomfortability and knowing that that was the skill set I needed, I looked at AI tools that would help me

form the community and maintain the community so that I didn’t have to do it all on my own, because I had never done that before, right? And it’s not realistic for me to be the moderator, to be the teacher, to be the leader, to be all of these things. And so I looked at the AI tools that would help me do those things, and I implemented them so that I can’t fail for that reason now. So if we look at lack of financing, well, I’m bootstrapping. So I’m good there, right? And then if we look at lack of a bad business plan, I was like, OK.

MKJ (09:27.864)

Yeah.

Ashley Gross (09:34.075)

Well, previously when I built my business, I would just kind of put an MVP together, take it to market, just do the dang thing, if you will. And this time I was like, well, what would an AI enabled employer do? They would figure out how much they need to make right from day one so that if you’re bootstrapping, you don’t have to have this break even period. You don’t have to be throwing a dart into a cloud and hoping it sticks on the dartboard. You have a number.

MKJ (09:42.882)

You

Ashley Gross (09:59.921)

that you need to hit. And so then you define the pricing for the community and the pricing for your products around that financial projection. So you’re not guessing anymore. And so I implemented tools like Wave, which is exactly that. It’s a financing automation tool that is technically an AI tool where I knew that a bad business plan was something that I didn’t want to have happen. So I automated all my financing so that I had a firm budget. I had financial projections. I had the daily updates for them.

You know, it’s just really taking your skills, what are you not good at, use AI to figure out what you’re not good at and fill those gaps. And then once you have those gaps solidified, enhance what you’re already good at because you’re probably going to go a lot further as far as impact goes.

MKJ (10:44.396)

Wow, that is amazing. I love that because that’s so many people think AI is just generative AI because that’s what we’ve seen with chat GPT even perplexity. I mean, I use perplexity almost exclusively because I use it for research and I’m not going to use generative AI for writing. I’m just not, I’m not comfortable with that. I have a very unique perspective and persona and communication style.

and I just haven’t been able to teach AI to do that for me. And it feels kind of weird to do that because I really, then I’m not human, then I’m not actually building relationships. I’m using AI to do that for me. I just don’t want to go there right now. Who knows if I’ll do it in the future, but right now that’s not it. So AI to use different types of AI, I also use it in another tool that I use called Zero Work where I’m actually building automations for the company for doing things that would take

Ashley Gross (11:15.292)

Yes.

Ashley Gross (11:23.569)

Right.

MKJ (11:39.416)

They’re repetitive tasks and I don’t want to have to do these repetitive tasks and I don’t want to have to hire a human to do the repetitive tasks. I can build a robot to do it for me. So what final words, what final advice would you give someone who’s looking at using AI, but they’re still a little bit scared, but they’re feeling a little more emboldened with your process that you’ve laid out? Is there any last words you’d like to give them?

Ashley Gross (12:05.361)

Yeah, I think you hit it on the head, right? Not once have I said I’m using AI to write for me or replace me. When people are using generative AI to write for them and be their voice, you can tell. It’s so obvious.

I’m really over the, you don’t use AI, you’re going to get left behind. You won’t. But what will happen is we live in an instant gratification world, right? Consumerism is instant gratification. You can click a button, have something at your door within 24 hours. For better or for worse, that’s the world we live in. So when you’re looking at your business, you physically might not get left behind if you’re not using AI. But your business and the competitive landscape will, because your competitors are everywhere all at the same time. And it’s only possible because of the relatability.

and personalization that comes with using AI tools. So instead of using it to replace you, look at it as filling in the gaps. What do you need to figure out? What needs to move faster for you to push the needle? That’s where you have AI come in. But make sure that that skill set is already good so that when AI comes in, it’s enhancing the good and not enhancing the bad. That would be my final words.

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