ļ»æHoward Wolpoff - Full Interview Transcript
From "I Suck at Sales" to Sales Confidence
AJ: Howard Wolpoff, welcome to the podcast.
Howard: Thank you very much for having me. I appreciate it. Nice to be here.
AJ: You told me something fascinating when we had our pre-interview - you used to say "I suck at sales," right?
Howard: I think that's pretty fair. A lot of people are not trained to sell, as I wasn't when I started my career way back when.
AJ: So what finally changed for you? Because I don't think you would say today that you suck at sales.
Howard: I would not say I suck at sales today.
AJ: So what psychological shift had to happen for you to go from "I suck at sales" to being good at it, maybe even liking it?
Howard: I think you really have to get some wins under your belt. Once you get some wins, you get some confidence, which obviously means once you get some sales, then you start to analyze what made that work. What can you use from that to move forward with other sales?
I was in my first sales job with no training whatsoever, but I was selling baseball. I was working for a Minor League baseball team in Brooklyn, New York, after the Dodgers had moved. We were bringing baseball back to Brooklyn with a Minor League team. I was getting some sales here and there, and that story was working, but looking back, I wasn't really selling - I just had a really great experience.
The Honeymooners Promotion: A Career-Defining Moment
Howard: We were planning a special day at the ballpark, honoring The Honeymooners - the old television show with Jackie Gleason, which was based in Brooklyn. He was a bus driver, and I was working with someone I connected with at TV Land because they had the rights to the show. I was able to secure rights to some of the programming we could put on the scoreboard. The giveaway item was a squeeze ball in the shape of a TV with the TV Land logo. This was a huge win for the team in general, but the fact that I was able to put all the pieces together and sell them on it and be successful really was a big confidence boost.
Long story short, the day we selected rained heavily, and the game was rained out. However, we did so much work to promote the event that we put all these press releases out, and it got picked up around the country. There were articles around the country promoting that we had Honeymooners night on August 16th - I actually think that was the date. It didn't happen then; it happened two weeks later, squeezed into a makeup game rain-out day. But the fact that all those pieces got put together and we sent out this press release and it got picked up nationally was pretty inspiring, and really was the boost I needed as I moved forward with that role.
Transitioning to Business Coaching and Consulting
AJ: Fast forward to starting your own consulting business. How did that confidence that you built through those jobs play out in your own business?
Howard: Well, thankfully, I grew much more as a salesperson from that point. There's definitely a timeline between when I left the baseball team to when I started doing business coaching. With that, I learned a lot of different types of techniques with sales. But I wouldn't say I was a sales master at that point either. Trying to separate a business owner from their money is not an easy task, especially when it's more personal as opposed to buying a widget for the company that you need to sell. Business coaching is something that's extremely important for business owners to go through, but not many of them would initially make that investment just from the first conversation.
You find different ways to go about selling. Actually, I just got out of a meeting right now, talking about what happens if people say no and the reasons they say no, and how to pivot from that. Knowing that type of information can help people, because not every no is a no. Some of it's a stall. Some of it is really trying to analyze what the offer is, and sometimes it's a no, but there are ways to walk through a conversation with someone to make that no into a yes.
Current Target Market and Impact
AJ: That makes sense. So tell me who your target market is.
Howard: Right now I'm a sales coach. I work with sales leaders and sales individuals. Sales leaders could be the director of sales, vice president of sales, or a business owner who has a sales team. They see the challenges they're having - they probably have people who really have no sales training that have been trying to work their way through. We work with them to come in and give a sales training workshop to their team to introduce sales coaching.
I also work with individuals who are looking at the challenges they're having, who know they need help. I work with them using the same plan that I would go through with a team of salespeople, so that they can really improve not just the revenues they're creating, but just their confidence and their understanding of sales. That changes everything in their life outside of work as much as it does inside of work.
How Sales Training Transforms Lives Beyond Work
AJ: So tell me more about that. How does it change their life in general?
Howard: I think in a couple of ways. One, when you're focusing on your time management - putting all the right time and effort into what you're doing in the sales day and structuring that so that you are not interrupted from the sales calls you need to be doing or the sales meetings - it also allows you to schedule the rest of your day. So it's family time with the kids and date night with your significant other, putting that into a calendar really does help the process.
Also, once you have confidence in yourself, once you're hitting your numbers and exceeding them, not feeling that stress of "what's going to happen if I don't hit my numbers, what's going to happen if I don't exceed my draw," and all you're getting is your draw, and three months later when you hit it big, you have all that money to pay back into the draw. Those are a lot of stresses that people have, and that does translate into everything they do in their life.
Using Podcasting as a Sales Strategy
AJ: I'm going to turn to podcasting, because you use podcasting as a sales strategy or lead generation strategy.
Howard: Yes, I have done that a number of times.
AJ: So tell me how that works. It's an unconventional approach that a lot of consultants wouldn't think of using. Tell me how you use podcasting to prospect for sales coaching clients.
Howard: Well, the key that you want to have with the person is a conversation. So, finding the right prospects who you think could be a good client would make for a great guest for your podcast, especially if your podcast is focused on the topic of what you're doing.
I had a podcast on small business marketing, and we talked about the journey of someone - how they created their business, what they did in the process of that, and how this evolved over the course of time. Small business owners who need sales coaching are great people to have that conversation with. Right now, I have a sales podcast where I like speaking to sales leaders with the same result.
When you have them on the podcast, you have a set of questions you want to ask, but you're looking for certain pieces in the answers as you're receiving them. Then, at the end of the conversation, a very strong tactic to use is: "Look, this was fantastic. I loved everything that you had to share. There are questions that I felt I couldn't ask - I really didn't want to record - but I really do want to dig in deeper and learn a bit more. Can we spend another 30 minutes tomorrow to talk about this?"
No one said no to me.
The Follow-Up Strategy That Works
AJ: Because when I'm curious what your follow-up sequence is - you talked a little bit about it. But how do you transition from "thanks for being on my show" to "let's talk about coaching"?
Howard: It's really about pacing yourself in the conversation. You do not want to jump in and say, "Hey, thanks for coming to join me. I've got to sell you something," or the translation that would properly go into that.
But the truth is, there are things I would really want to learn deeper about, and things that they learned. The next day, you're talking about these things you're asking now. You're digging questions as if you were really on a prospecting call, even though you're still focusing on the balance of it being a conversation, not a sales pitch. And then you say, "Hey, I have this idea. I have this thought," and then you go into your pitch of how sales coaching would help you and help your team, or how business coaching would help your business and some of the challenges that you're having as a business owner.
There are two ways to look at it. One is just a progression of them telling you some of the challenges that they're having. If you're just having it as a general conversation, and then when you feel you hit that point of "okay, here's some pain," then you go into it. Or there's a strategy to try to develop that information from people - to really find that problem that they're having, really putting salt into the wounds and asking them things about how they feel about the situations that they're experiencing, and then finally showing them that there is a way to address this. "I have this great idea, let me talk to you about it."
Overcoming Early Business Challenges
AJ: Speaking of challenges, I want you to give us a story or two about some of the challenges that you have faced starting your own business, and how you've overcome them.
Howard: I think the biggest challenge was starting off in the first place. I was Vice President at a marketing advertising agency here in Jacksonville, Florida. We were doing a number of things with our clients - really great work - but we also had a lead generation concept of creating a studio and having people come in for these online TV interviews that we were putting up on a website. They had access to put up on their social media and their websites themselves.
The goal after that was to bring them into a room and pitch them on this audit. The audit would go through everything about their business, their marketing, the images they're using, video, the back end of the websites - all of it. Then eventually bring them into an office with three screens and an hour and a half worth of drinking water out of a fire hose to eventually give them a pitch on how we can address all of it as a marketing agency.
There was a buy-in of $2,500 for the audit, and a lot of these businesses were - you could see the uncomfortableness because they didn't have a budget structured. Here's money allocated for marketing. There were challenges to them that if they took the money from wherever they were taking it from, that would remove it from something else, and they could see that calculating in their heads. More often than not, these small business owners did not take us up on the offer.
I saw an opportunity there, and with a couple of changes and timing being everything, it was the right time for me to move on and start working one-on-one with some of these types of business owners. It was definitely a challenge. I had worked from home before remotely at that point, but not full time remotely from home. It's definitely challenging getting used to that. You definitely want to make sure that wherever you're working is as far away from the refrigerator - that's always very helpful.
But getting in that rhythm of prospecting and pitching and developing a funnel took a while to get into the rhythm and then figure things out along the way.
Getting Decision Makers in the Room
AJ: When we talked earlier, you mentioned the importance of getting the decision maker in the room, which is a challenge that a lot of consultants have. How do consultants actually make that happen? What's the conversation that gets the CFO or the CTO or the CMO to join that call?
Howard: There's a whole process that I go through when I'm coaching my sales clients that really develops the conversation and allows for you to have this information be revealed. Taking a step back from that, whenever you're selling, you want to be asking questions. You want to be asking the right questions and answering them so that any objections that they have, you've somewhat addressed in the earlier process. So at the end, they're not saying "let me think about it," "I need to call you in six months," "I need to speak to my boss," or "I need to speak to my spouse."
If you ask certain questions along the way, then you've already combated those objections. So you're leading them towards saying yes. But it's very key to start the conversation as part of the conversation - asking the right clarifying questions of where they're at at this point, and the things that they are happy about that are happening right now. You shouldn't be afraid of asking those questions, especially if there's another company that they're working with. Don't be afraid of that - find out what they like, find out what they don't like, and that's the key.
Now you have a sense of what's the good, the bad, and the ugly, and why they're speaking with you. Then you want to find out: is there someone else that needs to be part of this conversation? Before you go any further and throw them a pitch, you want to know who you need to speak to. If the person's not there, then you need to speak to them at another time when they can schedule the appointment.
The Biggest Mistake in Multi-Decision Maker Sales
AJ: What's the biggest mistake you see consultants make when they're selling to companies where multiple people are involved in the decision?
Howard: You want to have everyone on the same page as fast and quickly as possible, and that's it. Sometimes it's hard to get everyone to a room, but you want to make sure that if you can get people into a room as fast as you can. You don't want it where "Oh, okay, let me go speak to my boss" because now you have the game of telephone. They're not going to have the same information that you are providing. They'll give highlights of it, and that other person might not have the same excitement that they do sharing it with them. So it's just about making that appointment the right way.
The Art of Follow-Up: How Many Times Is Too Many?
AJ: How many times should a consultant follow up with a prospect before giving up?
Howard: That's a very interesting question, and that question has evolved over the course of time. I've learned a lot of different things. You've got to speak to them five times. Try five times, and that's it. No, now it's changed to 10 times. Now it's changed to 20 times. You've got to think about it sometimes as a television campaign. They're looking for reach and frequency because people aren't paying attention all the time when the conversation is being put in front of them.
You have to have a mix of ways you're reaching out to people. It's not just on the phone. It's not just an email. It's a blending of it - it's communicating with them through LinkedIn.
The unfortunate answer is: it depends on the person in the end. My strategy on marketing is people want to be marketed to the way they want to be marketed to, and that could be a lot of different things and a lot of different methods. So sometimes it may take 10 times. Sometimes it may take 20, but revisiting someone every so often is not a bad thing as long as you know where that line is between positive follow-up and absolute harassment. You've got to know what that line is.
Lead Generation Strategies That Work
AJ: How do you generate leads?
Howard: In different ways. I think first and foremost, the best way for anyone to develop a lead is through referral. You have an endorsement of someone already having the conversation. If you're able to start the conversation the right way, you can get people very excited about the fact that Joe gave their name for you to speak to, and that just rolls into the process.
Other than that, like years ago, you really would go - pre-COVID - going to networking events was such a big thing. But the challenge with that is, unless you really are dedicated and you're going to play the long game, it's going to take a very long time to really make enough relationships with the people in that room for them to be comfortable with giving referrals. Even if you're spending money on a BNI, it's still going to take time for you to really start to see that investment being recouped in the process.
You have a lot of people that know you, and they may not be your prospect, and that's probably a good thing in this process. But if you start digging deep into your network and reaching out to people, you'll find lots of different people who can refer you to the right people, because they know a lot of people. It's just really trying to find that right rhythm to it.
But other than that, there are so many different resources to do searches and find leads - lots of different programs out there that will generate the leads for you. Leads can be found. It's not hard to find leads. The hard part is trying to sell them.
The Reality of Third-Party Lead Generation
AJ: Do those methods of having a third party find leads for you work for consultants?
Howard: I think in the same way that trying to connect with people randomly on LinkedIn because they have the right title works. It all depends on the mechanism of how you're trying to connect with them. If you've signed up with a company and they've given you a thousand names that match your avatar, that's wonderful. Hopefully, they've also given you some sort of suggestion of how to communicate with them.
But the truth is, if you can get them on the phone, that's the best way. Texts and emails might have been successful, but you've got to be smarter. You have to be really strategic about what you're writing to capture people's attention. Someone sent me an email before that I didn't know who the person was, and the subject line was "devastating diagnosis." I opened it up because I wanted to know what that was. Basically, it was "I have something to sell you" and all the other basic subjects for emails. Most people are just going to delete those.
So it's really: can you get them on the phone? Can you create rapport with them quickly so that everyone - each of you and they - are smiling in the process so that you can have a conversation with them as opposed to "It's another sales call where I'm getting myself into trouble picking up the phone."
Breaking Through the Cold Call Barrier
AJ: So, but people are busy, and if you call them, they weren't expecting your call. They don't know you. How do you actually get them to talk to you without them being on guard that "oh, this guy's going to sell me something"?
Howard: Well, you have to really have a light approach about it. If you don't want them to be annoyed, you don't know what their personality is, but you want to say, "How can I make them smile immediately when I get them on the phone?" So one of the tricks that I use is confusion.
I will say, "Hi! Is this Joe?" And wait to get a response and say, "Yes, this is Joe." "Hey, Joe? This is Howard Wolpoff," and I will stop talking, and I will sit there and wait just a little bit to see what kind of response that they give me. Sometimes they're like, "Oh, oh, Hi, Howard!" because they don't know - they can't remember if they know me or don't know me. Or "Hi!" with a question mark, and then I'll let them off the hook: "If you're trying to put a face to the name, it may not work because we actually have not had the opportunity to meet yet."
The hope is you're going to feel them smile. You're going to hear them laugh like, "Oh, that's why I couldn't figure out who you were." And now you've got a little chit-chat conversation going as opposed to some cold caller on the phone.
And now, if you have someone who's referred you: "Yeah, Joe, Michael suggested that I give you a call," and then start. You've already taken notes with Michael of good things to talk about Joe. "You're the best bowler on our bowling league. What a great father! All the things you're doing! You're the most successful partner at our law firm," and then, after you've built them up like that, you'll say, "This help me, or does this hurt me? Did I miss anything?" So now it's all about them.
It's all lighthearted, and then you can go with "the reason why I'm calling is" and then go into your pitch. If you've just gone, "Hey, my name's Howard. I'm a sales coach. I would love to talk to you about sales coaching for your sales team," 99.9 out of 100 are not going to let me go any further than that.
Three Essential Pieces of Sales Advice for Consultants
AJ: If you could give three pieces of sales advice just to a self-employed consultant, what would they be?
Howard: Advice to a consultant: Have a plan. You have to have a plan. You're not just saying, "Oh, I'm going to do this, and here's my shingle." You have to have a plan.
I would also say, make sure you save up before you start. You don't want to go in - granted, sometimes you're fired and you have no other choices. "Okay, this is the kick in the butt I needed. I'm going to go do this." It does make it easier if you have some flexible funds, not only just to live off of, but to spend on certain things - building the right website instead of "okay, I've got to go do it myself through software, and it doesn't look good." Being able to purchase certain other methods to help you move the needle forward. That is very helpful.
And just understanding how to sell, because no matter what you're doing, you have to be selling. It's very rare there's a job that you're not selling. Someone goes to medical school and becomes a dentist and opens up a practice. What do they have to do? Sell themselves as dentists. It's not just fixing teeth. It's selling people to be a client. I can go on with all these other different industries, but selling is the heart of everything that has to do with business.
The One Sales Skill That Transforms Everything
AJ: Sales is a very big, broad area. What's the one sales skill that, if mastered, would transform most consultants' businesses?
Howard: Understanding the personality of the person you're speaking to. I say that because there are basically four different types of personalities, and some blend into each other, but they're four distinct ones. If you can figure out, first of all, if you have an understanding of your personality and how it interacts with the other three, and then you can quickly pick up what that personality is, there are ways to speak to that person within your personality that will open up a conversation better than butting heads with people.
There are people who you get on the phone, and it's clear this is the worst decision in the world they've made picking up the phone. But if you know how to soften that person, you might actually get a sale out of it. But if you fall into the pattern that they are sharing, then that's never going to happen.
For Those Who Can't Afford Coaching
AJ: For somebody who's listening to this podcast who's thinking, "I need help with sales, but I can't afford coaching," what's the one thing they could start doing tomorrow?
Howard: There's a lot of information out there. I think even if you just go to my LinkedIn profile, what I write on a daily basis really gives a lot of different types of tips and things that sales leaders and sales individuals should focus on. Even that would help build up your mindset differently about sales, even if you don't have the full hand-holding one-on-one coaching that someone who goes into sales coaching is getting.
Because the truth is, it is very, very rare that anyone has any school training on how to sell. So you're not alone in that, because I would say 75% of people who are selling right now had no training whatsoever, whether they've gotten some specific training at the places they've worked at or coaching. That's the only way that it's really developed.
Working with Self-Employed Consultants
AJ: Do you work with self-employed consultants?
Howard: Yes, I do. I think that they have a great need to sell, because most of them are wearing multiple hats, and the faster you can teach them to sell, and the faster they're able to create the revenues they need, then the faster they can hire other people on to build this into more of a company than just a solopreneur operation. Someone else can do the selling for them while they're focusing on what their real talents are.
Final Words of Wisdom
AJ: Any last words of wisdom before we sign off for today?
Howard: I have a friend I used to work with in baseball, and his slogan was, "If you're not selling, you're not selling." So if you look at the phone and say "not again," you've got to get that out of your head. Pick up the phone, make the phone calls. That's the only way you're going to keep your business and yourself moving forward.
AJ: Phone calling is often not in that list of things people want to do when they talk about lead generation techniques, so that's challenging advice, but challenging for a lot of people who don't want to have to do that.
Howard: Unfortunately, at some point you're going to have to speak to the person if they're going to be clients, and the only way to get them to be a client is to speak to the person.
The Role of Lead Magnets and Discovery Calls
AJ: One of the popular sales processes or marketing processes right now is to develop a freebie or a lead magnet that gets somebody to opt in and give you their email address. And then from that you hopefully figure out a way to get them on a discovery call, otherwise known as a sales call. What do you think of that as a way to get leads without having to make phone calls?
Howard: I think it's a great way to generate leads. I think if you have the right email campaign that goes along with it, you may not have to make phone calls in that situation, depending on what you're selling. If you're selling a course and you do everything online, that's the best way to go. But if you're really selling a service - selling yourself as an educator of someone in different ways and different methods - you're going to have to speak to them at some point in time.
AJ: Thank you, Howard, for being on the podcast today.
Howard: Thank you very much.
