How to Win Bigger Deals and Avoid Getting Ghosted

As an entrepreneur, you often end up wearing many hats, and sometimes you don't feel like quite wearing those hats. I see it happen all the time as it applies to sales. That's why today we're joined by Brian Cristiano. He's the CEO of Bold Worldwide, which is an agency here based in New York City, and he's a sales expert. Beyond that, he's also an expert of personal branding and how you can use that to get closer to a yes. Before you even get on the phone with a client, Brian's going to start by sharing his why. And I'm sure you've heard this before, people don't buy what you do, they buy why you do it. So let's hop into that right now. Sure.

Terry, it's good to see you. Well, you know, I'm Brian Cristiano, founder, CEO of Bold Worldwide, the strategy and marketing consulting firm in Manhattan. Also Bold CEO Brand, which I advise, invest and train up other business owners to grow and scale their businesses.

So I'm sure you've heard this before. People don't buy what you do. They buy why you do it. So what is your why?

Oh, man. I want to touch as many other businesses as I can. What I've realized is one of my biggest strengths over these last couple of years is I have the ability to take other leaders and make them better leaders. And if I can impact other leaders, meaning business owners, they have employees, they have families, they touch so many more people. So instead of me being focused in on, you know, how do I do something one time transactional, how do I create impact with other leaders who can create more impact? And so that, to me, is my why. It's exciting because I get to see that, you know, helping one other person become a better leader and grow their business impacts potentially hundreds or thousands of people.

Brian makes a great point here. Not only does he want to help people, he wants to help people who help people. And therefore, his impact will be multiplied. And guess what? You probably have the same situation. And I'm not saying this to put pressure on yourself, but realize the impact of your work goes further than the person or the organization that you're working with. So you want to make sure you deliver really good outcomes. And if you haven't noticed already, Brian's background looks amazing. So that's a part of his personal brand as well. And now he's going to go deeper on how his personal brand helped him pivot during 2020. Let me go deeper, because, Brian, you're. I know you're at home right now. Your home studio looks amazing, you got lights, Everything's just, you know, well designed. So my question is, you know, how do you think your personal brand has helped you build your business over the.

Terry, you know, that's a great question, because my personal brand has definitely impacted my ability to grow what I'm currently doing, my agency originally and my other ventures that I'm a part of. And the reason for that is, I think if people don't know what you're up to, if people don't know who you are, if people don't understand the mission and vision that you're trying to create, they can't get on board with you, they can't help you, they're not going to spread the word of what you're doing. And so having a personal brand, which allows you to really have a platform to showcase others and connect with others of what your vision is, what your mission is and what you're trying to do will collect the other people that want to get on board with a similar mission or have a similar view of life. And so without that personal brand, I don't think I would have been able to build what I did as quickly as I did and pivot and make changes as fast as I did.

I know I harp on building a personal brand, but that's how important it is. People already know, like and trust you before they even get on the phone with you. And if they don't want to buy your services, they might spread the word on your behalf. So if you want more help with that, check out the interview I did with Shanae Marais. She'll give you step by step advice on how to do so on LinkedIn, Clubhouse and more. But for now, let's get back to Brian. So I've seen your videos on social media and on your website, and I know you went to college for film study. Can you explain how that helped you? Just the way you present yourself and maybe what other people who maybe didn't go to college for this can do to better present themselves online.

That's such a great question because. And I don't get asked that very often, it's really a unique perspective that you brought there. Terry, you know, my background originally, you know, wanting to be a cinematographer and a film director and traveling down that path allowed me to really get better at the creative side of the business, which is how do you tell a story? How do you hook people into a message? And then as I started to realize that, I actually like the business side Better and built an agency and built bold CEO. And what I'm working on now, as I move further into that, my creative background absolutely has helped me because I find that a lot of people that just strictly have a business background really underestimate the power of really good storytelling. They underestimate the power of really good creative and quality visuals. They underestimate the power of that. But if you think about it and you look at, you know, what are the most successful movies ever and most, you know, successful action parks and things like that, they're the most polished, they have the best stories, they have the best experience of anything. And so I think that having a creative background has allowed me to take and consider the experience for clients, for customers, for people from a marketing perspective and then apply that in a business sense.

So what really stuck to me here was Brian's commitment to telling a good story. And you want to do the same. But if you want more help than check out Donald Miller Story Brand Principles. He'll teach you how to tell your story, but from your audience perspective and how you're guiding them towards success in helping them avoid failure. That's going to stop you from talking about yourself and make a more authentic connection with your audience. Again, I know you're doing other things now. You're doing consulting, you're doing advising, but you are excellent at building and scaling agencies. So I'm sure a lot of people ask you for advice on how to do that. But what is one question that no one ever asks you, or they rarely ask that they should be asking because the answer is so critical?

Oh, the question no one asks when it comes to scaling any business, but especially advertising or creative firms, is should I scale? I think everyone needs to really ask that because you can have a hundred million dollar business where you never see your family, you have absolutely no creative freedom, you're working 100 hours a week and your margins are 2%. That's plausible. And that's quite frankly a lot of businesses of that size, especially in the advertising world, and no one ever steps back to say, hey, what do I actually want out of my business? What lifestyle do I want my business to provide for me? And Maybe that is $100 million business because there's nothing wrong with that. Maybe that is a billion dollar behemoth, or maybe that's a million dollar company with a good margin, with the flexibility and a good team where you can spend more time with your family. And most people don't ask that, they just simply go, how do I grow? Why do you want to grow?

I love this point. Who says you have to build a multi million dollar business society? Some magazine? Your friends? No, you define success based on your own terms. And when you think about the three time lifestyle and financial, there's a lot of wiggle room there for you to make it your own. You determine fulfillment. We know money can't buy happiness, but if you're stressed out over payroll, paying your vendors, your bills, you know what's going to make things better? Money. And that's why Brian's going to share some really good sales tips he's used internally as well as externally as a consult with people just like you right now. All right, so you're an expert on sales and I want to get more into that momentarily. But some people that are listening, they have a sales cycle that's super long. You know, it could be several months or years that it takes to get a yes. So how do you maintain a relationship in between that, that, that initial point of contact and a yes? How do you do that over time without seeming like you're pestering someone or just finding excuses to reach out? What does that look like to you?

Yeah, that's a great question. I think anyone with a really long sales cycle needs to consider two things. Number one, if you really do have a long sales cycle, you need to, you need to give value and create and build a long term relationship, right? Which is how do you really help them even if you're not actually trading commerce, can you point them in the right direction? Can you give them a resource? Can you connect them with somebody? Can an employee for them? Even if it's completely unrelated to what you do? I've always found that when you help someone out in one way, shape or form, that relationship bond becomes strong because most people in sales simply just go, hey, just following up. It's been three months. It's been six months. Did you get my proposal? Did you get my email from last week? And that's all anybody does at surface level. But people that go deeper and say, hey, how do, how can I help you? I know you're not ready yet, but how can I actually help you? What do you need in your business, your life? Maybe I can help you and maybe you can't, but if you can and you do, you're going to build a long term relationship. And number two, really question, does the sales cycle actually need to be that long? I think the problem for a lot of people with a long sales cycle is they're trying to sell an entirely large Complex package. Here's this big complex solution. Like for example, a marketing, you know, you know, marketing agency. We're going to be your full service marketing agency. Well, yeah, to close a deal that's a full service marketing agency can take a long time because there's a million variables, there's a lot of decision makers, a lot of change has to happen. There's a lot of risk, or at least perceived risk risk on the prospective client's part. And so you need to ask yourself, is there something that I can sell? I call it a wedge. Is there something that I can sell? That's a small step, a small engagement prior to the full engagement. Because if you can, not only are you actually adding value, but you're getting paid for that value before this long sales cycle even needs to take place. And oftentimes when you do that, the sales cycle shortens because you're already doing business together.

So I want to go deeper on this wedge you refer to. And I've heard you talk about the wedge strategy on social media. Can you unpack that? What does that mean in application?

Here's the thing. You know, when we're talking about a wedge strategy from a sales perspective, you got to think about this, right? Most people that try to sell, especially in B2B or service type businesses or consulting businesses, they try to go in, you know, they try to take like an ax and go up to a tree and they're like, okay, the ax is like everything I've got, it's my full proposal. It's all the stuff that I can do. Everything that the prospect asks for, every possible scenario. I spent tons of time putting the proposal together in the perfect possible way. And then they take that swing to the tree with the ax. One big swing. You're not going to chop down the tree. And that's what oftentimes happens and turns into long sales cycles. Because these big proposals, these complex plans, it just takes so much brain power and so many people to approve something like that. And so instead of going in and trying to swing the ax with one big foul swoop, look at a wedge. And this is actually true. Most people don't know this. The actually the fastest way to cut down a really big tree is you cut a little notch in it and then you put a wedge in there and you hammer the wedge in a few times and then the tree just falls over. And it's the same thing from a sales perspective is what is that wedge? What's the thing that we can actually sell? Might be strategy. It Might be consulting. It might be some small piece of your process or some small piece of your SaaS solution or your product that was like an initial step just to get them in to show them that, hey, listen, we understand where you are, we know where you want to go. This is the first step. And it's not a big commitment. Because if it's not a big commitment, it's simple, it's a no brainer and actually has impact. Well, obviously they're going to move forward with it. And then once you get that wedge in, guess what happens? You hit it a few times, you knock the tree over, and you close the deal.

All right, so to recap here, two things. One, if you have a very long sales cycle, find something to do during the interim. Help them with a new hire, tell them about a new podcast they should listen to. Maybe nominate them to speak on some kind of committee. Whatever it may be, do something besides reaching out saying, hey, just checking in here, because that does not work. I have tried it. Right, and another point he makes is, does your sales cycle have to be that long? Is there something small you can sell? You know, a quick win that will accelerate the process of getting a yes and build that trust in your expertise so it'll be easier for you to get a yes for larger offerings. So let's say you focus on organizational training for starters. They say, hey, how about I just train like three of your execs? We'll see how that goes, get some feedback, and then roll it out to the rest of your organization. Get that quick, easy, yes, just do a workshop, whatever it is, but build that trust, show your expertise, and then go for a larger package. All right, Brian, this happens all the time in sales. You know, things are going well, you send a proposal, you're having all these conversations, and you get straight ghosted. How do you reply to people? Or how do you follow people that just ghost you without seeming desperate? Salesy cheesy, like, what would be your advice for that?

Oh, great question, Terry. I see this happen all the time. And that's one of the other biggest challenges that come up for people is, you know, I get ghosted. The client's excited, the prospect's excited, they want to move forward. We hit all of their pain points, we solved all their problems, we presented the proposal, they were excited about it, and then crickets. First of all, why does that happen? That often happens because the solution that you're proposing is complex. And so it takes too much brain power, too many people to now make a decision. Because it's not just based on what's the price per the value they're looking at. This is going to take a lot of time. Is it really worth the effort for me to move things around? Is my personal job at risk if we're going to implement this big solution? There's a lot of psychology that happens when you present a proposal, even if the prospect likes it, and so they don't want to hurt your feelings oftentimes, so they just won't respond, which is worse. But they think they're trying to help you out. And so what you do in that scenario, and I'll give you an exact tactic that you can use, is you follow up and you. And instead of saying, hey, how's it going? Have you looked at it? Have you had enough time? Because that sounds desperate need to take command and take control of the situation. And what you do is this is you figure out, okay, based on what we actually proposed and based on what the outcome is for the client, when would this actually have to kick off? Is it a month from now? A day from now? Last week? Figure out that actual timeline, because timeline is important. And when you could put, you could put a pin in a timeline, then you can create urgency around it. And this is when you reach back out and you say, listen, I was looking at everything that we proposed and I realized that what you want the outcome that you want to correct this problem that we're trying to solve for, we actually need to get this going in a couple of weeks. And so I put the team on hold for you because I know that this is important to you. Should I keep them on hold for the next couple of weeks or should I move them onto another project? I'm telling you, I've had hundreds of people have, you know, send this kind of a message out and almost, almost 100% hit rate, they will get a response and you'll at least now understand where the prospect really stands. Are they blowing you off? Do they really want to move forward? Do they have some sort of problem with your proposal? They will respond because nobody, you know, if they're a decent person, is going to leave you hanging when you put the team on hold and you need to figure out what's going on in the next couple of weeks?

Yeah, I love that. And if they're not a decent person, you save yourself a big headache by not working with them.

Exactly. I'd rather know that as soon as possible too, so we can move forward.

I love the idea of reaching out with a sense of urgency, but it's all based on their timeline, not yours. So you have to ask that question. When does this need to launch? And as Brian said, if it's getting kind of close to that time, you can say, my team is on hold. I want to make sure we're here for you. Do you still want to do this? Another question I love asking is, how important is this? How much of a priority is this for your business? Then I know when they want to have it done and how important it is to their overall business goals. But keep this in mind. To do this effectively, you have to track their responses to these questions and set reminders for yourself when these timelines are coming up. Now, I use a tool called HubSpot. It's a customer relationship management platform you can use to track every stage of the user journey from prospect to client. I've been using the free version for, like, three years. Okay, so we've talked about overcoming objections, accelerating your timeline, even how to avoid getting ghosted. But for some of you, that's not the problem. The real problem is just getting started. And if that sounds like you, stay tuned. Ryan has some great tips for you. Let's get deeper on a personal level, and you don't have to give me names or specifics, but can you give me an example of someone who's just horrible at sales and how you help them get better?

Absolutely. Actually, an employee of mine, Alex, who's worked with me for years now in multiple of my companies. And when he first came on board, he was here to do outbound sales, and he had no idea what he signed up for. And I sat him down and said, okay, here's the process. Here's what you're going to do. You're going to make 150 outbound calls every single day. And he was like, wait, what? And he has told me since that he went back to his wife that day and said, hey, honey, we're probably going to have to move out of New York. I don't know if I can keep up with this pace. And the kicker was I was having to reach out to Fortune 500 executives. And he was like, I don't even know how to talk to people like that. And here's the thing. In the first handful of calls, and he would connect with people, and he would totally fumble on it. But then what I started to get him to see, really, is they're just like you and I. There's no difference. Just because they have a bigger paycheck, just because they work at A bigger company with more zeros and more employees. They're just like you and I. They've got problems, they've got challenges, and they're looking for good people and good companies to partner with and to work with to help them get to the next level. And if you can really connect with them and you have a framework and a script and you understand what the right questions to ask are and when to ask them and how to do it simply and quickly, you can get Fortune 500 executive on the phone and you can get a deal. And when Alex, after a couple of weeks of training, he got in front of the CMO of Carnival Cruise Lines and he actually turned it into an opportunity. And he was like, I can't believe it. It worked. But it was because he followed the process and he changed his mindset to, instead of putting these people up on a pedestal, understand he's just there to connect them with our company and help them move forward and solve problems that they have. Because they all have problems regardless of their size. And typically the bigger they are, the more problems they have.

So after he called out Alex, he had some really good tips for you. The best way to get better at sales is to just get started. Now, he had Alex calling Fortune 500 CEOs, which is pretty bold. That's why it's the name of his company. On my end, I took a different approach when I had a similar role. I called very small companies because I figured if I messed up, there wasn't too much to lose. But just like Brian said, you know, we all have problems, right? You know, no one's on this pedestal. We all have problems. And if you have a solution, it is a disservice to your company and to that individual not to share it with them. And here's the thing. You don't have to have all the right answers in the moment. You just have to ask the right question. Brian's going to explain more about that now.

The biggest thing that I've seen after working with so many people in this kind of regard, different than when I was really managing the agency, is a lot of people lack confidence in their business. And I'm talking people that have million dollar companies, $10 million companies, $80 million companies, because the scope of the people that we're training is wide and they lack confidence. They might not seem so on the outside, but when you really start to break it down, you realize that they're putting their prospects up on a pedestal because they lack their own confidence. They're afraid that they don't know enough. They're afraid that they can't answer every single question. And what I found that really solves that is getting people to understand. It's not about having the answer to every question. It's about understanding what are the most powerful questions that you can ask that gets your prospect to come on board and see from your perspective what you see about them. Because it's like you have a good friend or a spouse or something and you're trying to get them to see this problem that you see this thing that they're doing. But like if you just told them, like, hey, you're doing this thing and it's stupid, they're like, shut up, like they're not going to listen to you. And a prospect is exactly the same. And so. But how do you actually get somebody to see what you see? You ask them questions, hey, how's this working for you? What are you doing about this? You know, what's your outcome that you want? Where are you going? Where do you want to be? Where are you today? And asking those on a much deeper level than I'm giving examples here right now, to where all of a sudden that person starts to connect the dots for themselves and says, wow, I need to change. And then you're there assuming that you can help to help them solve it. You're there in that moment of need. You just got them to take the wool off of their eyes and to see it. Finally, the problem for what it actually is, that you could see that is powerful and that builds confidence. And it doesn't require to have every answer, it just requires understanding what are the most powerful questions that you can ask?

Alright, so I know asking questions might seem like a weird way to establish your expertise. Let's think about it this way. Imagine you go to the doctor and you tell her you're sick. How would you feel if she said, what should I do? You would say, I don't know, you're the doctor, ask me some questions, give me some drugs and I will leave. That's what doctors do. Well, they don't always give you drugs, but you get the point, right? That's what a business partner should do too. A vendor is going to get on the phone and ask the prospect what they want. A business partner like you, you're going to get on there, you're going to ask power questions. They reveal blind spots and opportunities and prescribe solutions. Asking powerful questions and delivering powerful solutions is how you stand out even in a competitive environment.