ļ»æHoward Full Interview Transcript
Introduction and Background
AJ: Howard welcome to the thriving through podcast I'm delighted to have you as my guest today.
Howard: Thanks, AJ. It's a pleasure to speak to you again, and I'm really honored that we can have this conversation.
AJ: I have 2 questions that I ask all of my podcast guests right out of the gate. How long have you been a self-employed consultant?
Howard: I've been on my own. Now this is my 3rd year.
Career Journey: From Attorney to Sales Leader
AJ: Tell me about your path to becoming self-employed.
Howard: That's a really good question and an interesting story, and I'll try to keep my journey as short as possible. But I actually started my career here in Chicago as an attorney, and I litigated for 5 years. I was 30 and bored and was not enjoying my day to day fulfillment in my role, and I actually sat down with a family friend and went through an exercise of trying to figure out what I liked and didn't like, and what I did well, and things I did not do well.
I knew I wanted to leverage my law career, but I didn't necessarily want to be in court every day arguing about this, that, or the other thing. I found my way to a very large organization that was a division of Reed Elsevier and I went into sales, and I was actually working with law firms of all sizes, helping them to manage their information and their front office and back office solutions. I quickly fell in love with sales.
I had always in the back of my mind felt I was always in sales, but it was never a formal role. I started working at 15 in a restaurant, and just worked my way through law school, and then, obviously, being a lawyer, you're selling every day, but from a KPI perspective and having goals against you that was certainly new. But I did really well as an individual contributor, and was promoted relatively quickly into management. So I was now building sales teams and managing people and process. And then I got experience with that company more at a regional level. So I was in charge of helping to craft the strategy regionally and then implementing it across multiple teams.
Now fast forward about 25-30 years of corporate life. I moved around to various number of firms, about 5 or 6, always in that sales leader role, and where I developed a passion, was really helping businesses align their business plan to a sales plan that was also tied to the marketing plan. I refer to that as the business development ecosystem and really make sure that's aligned. And then laser focus on people process and how company drives sales in order to impact top line revenue.
The Decision to Go Independent
Howard: In 2014, I actually was leaving a private equity based technology firm. And I sat down and wrote a business plan for what at the time was called Vice President of Outsource sales, and I came up with all these names. I then decided, well, I couldn't be the smartest person in the world. So I googled and came across sales acceleration, and at the time they were founder led with about 20 former VPs of sales senior VPs of sales across the country.
I had a 3 year old daughter. So I actually had an opportunity to go in house and lead the Security risk consulting sales for a company called Hillary Hines, here in Chicago, and it was in that sales leader role, and I decided being in house was maybe a little bit better for my life stage than being a consultant.
We quickly grew from 8 million to about 20 million dollars, and then we sold to a private Equity Company, and I stayed with them for about another 3 years before I really developed a desire to brush off my business plan and really give back to the small and mid-sized business community. I did that, and I re-engaged with sales acceleration, and left my job in May of 2023, and then I launched in that next month, June.
Early Challenges and the Volume vs. Strategy Lesson
AJ: Tell me a story or 2 about the biggest challenges or obstacles you've faced, and how you've overcome them.
Howard: Well, I think the first obstacle was getting my arms around some of the guidance I was giving about how to build a business and making it my own. And what I mean by that is that in the fractional space, I would say 99% of the business is traditionally done through referral networks. So whether you're meeting with other folks who could be conduits to your decision maker or ideal client profile, groups or associations, and it was initially shared with me that it was more of a volume game.
I quickly realized in the first few weeks that volume wasn't where the answers were at. It was really strategically understanding who my decision makers were going to be and who I wanted to work with. And then I asked the simple question: well, who are they complaining about? Because sales are not where they want to be?
So, when working with founder led, or family run businesses their traditional couch moment, who they're actually complaining to is going to be business coaches, or usually someone in the financial lane. So a fractional CFO or the CFO in their company, or even their financial wealth advisor. So I really started to focus in on that.
Plus, I was fortunate in my network that I'd worked with a lot of small mid-sized business owners. So I also made the conscious decision: Well, who are they networking with who's in their circle, and how can I get to them? And when I shifted that lens in month 2, that's when I would say the business development side of my own business started to flourish.
Becoming a Trusted Advisor
Howard: So I think that was the first challenge that I took on and was successful to overcome. I think the second challenge is actually doing the work because you're really passionate about the lane that you're in. But then, when you get that first client, it really comes to the rubber meets the road, so to speak, and you have to take in all those experiences you've had, and to a certain extent the partnership with sales acceleration has helped in that regard, but at the same time you have to make it your own, and you also have to figure out how it's best going to meld into the relationships you want with your clients.
I think the second problem was, I found a lot of people in my lane, or other fractional lanes come in and are really tactical and really want to focus in on their area, which I think is obviously the perfect thing to do, because that's what you've been hired for. At the same time I knew that my experiences were more well-rounded, and it wasn't just on sales. I'd worked with companies going through acquisition. I've been involved in HR scenarios and marketing plays, and really everything across the dynamic of a business. And so I said, I don't want to get in there, but I want to become a trusted advisor and counselor to my business owners and family members.
Switching on that lens and trying to add as much value as I could, has really transformed some of my clients from what should be a 6, 12, maybe 18 month engagement, and I've got 3 clients right now one that started year 3, and the other 2 are just completing year 2. And that's solely because I think I've risen to the challenge of trusted advisor as opposed to just being the sales leader or manager for the team.
AJ: Tell me a little bit more. How do you develop that? How do you become the trusted advisor?
Howard: I would say it's been a little bit more complex now, as my business has grown, and if we had time I'd love to share with you challenges 3 and 4, because those are ones that I probably need some guidance on. But I think what it is, is one of the things I mandate in my engagements is that I'm part of the executive leadership meetings, or I'm in the know-how about what's going on, and that has resulted in me being in at least 2, if not 3, being the sales chair in their EOS entrepreneur operating system teams. So that means I'm now going to their quarterly meetings. I'm responsible for getting things done through whatever software they have to manage it.
And then I also peel back the curtain, and as I tend to have very open and honest and vulnerable conversations. And because everything touches sales I can adequately share: This is my observation. This is what I see is going on here, going there. So it's not just about sales. It's people oriented. It's process, it's culture. And to date, my clients have really resonated to that. And that's been both fun and fortunate.
AJ: And a trusted advisor is always a much stronger position to be in than just a gun for hire, so to speak.
Howard: It is, and I will say that the challenge for all fractionals as your business grows and you want to scale your own business, it's figuring out that bridge, because it's tough to be the trusted advisor to all clients, because it's not just a scoping issue, but it's a time, energy and value issue. So there are times where I think you have to make value decisions based on what a client needs and where you can actually play. But for the most part, I'd say probably about 90% of my clients I could say, I believe I'm either on the path to trusted advisor, or I am trusted advisor.
Selling Your Own Services as a Sales Expert
AJ: So you are an expert in sales. Do you find it different selling yourself and your consulting skills? Has that been harder than leading sales teams and managing sales teams?
Howard: No, because when you're managing sales teams, you're really working with people, and every single person is different. Every experience is different. And I tend to find that when I come into an organization that has sales people, there's always a moment of pause that oh, my word! This person's coming in. He's going to make a lot of changes. You really have to really get underneath people and process. And really, how are they being managed? I really enjoy having conversations about what I do and the value I can bring. I find that to be extremely easy to engage in conversations, and for the most part prospects I've worked with have been very receptive to the process and engaging me.
I would say that where people might lean a different way. Sometimes people want to insource it. Fractional is usually like a half a day or a full day a week, though I hope my clients don't feel that. But that's from a scoping perspective. Some were like, we'd like to have a sales leader here full time. We think they might get bang for the buck better for that. But most of my clients really resonate to the fraction, because they want my 25-30 years of experience. They want me to bring the processes and the products and the know-how, and try and get that done as quickly as possible without the risk of bringing me on full time. Or maybe I don't hire correctly for the sales leader role.
So I think business owners and family run business do the cost benefit analysis. I think they lean towards a fractional leader like myself.
Working On-Site vs. Virtual
AJ: When you do your work you have to be on site, or is it virtual?
Howard: Another great question. It's a little combination of both relationships, even in this day and age, are better built on site. I also get to see how the company works. I get to hear other conversations. I really get to know the nuances.
But once again, I would say you have to pick and choose when you're on site with clients, and it also depends on the maturity of where you are in that relationship. So I have one client that I started working with actually August of 2023. So we're going on our 3rd year. And I used to go every week. And now, because the sales teams in place, the processes are there. We're getting the growth that they want. I'm part of the EOS team. I'm flexing. I'm only going in every other week, or when we have sales meetings or one on one meetings.
Other clients I've worked in the past 100% remote. I've got a client today, that's on the east coast, in the Boston Massachusetts area. And that's a hundred percent virtual. So I think you can do either. I think it just depends on the client situation, and I think you pull that lever depending on how important it is for the leader to feel like they're getting their full value about whether or not you're on site. I've got one client that I don't think I have to be on site, but that's what he likes. He doesn't believe in remote working, so I go in on Thursdays and it's another client that I'm part of their EOS team. So it's really nice.
Scaling Challenges and Business Growth
AJ: Being a fractional, how do you see scaling your business? Because you can only be fractional for so many hours of the day, we only have so many hours. So how do you scale to go beyond sort of time for money?
Howard: When we talked a little earlier about challenges 3 and 4, that's where I'm at. So I was fortunate. I landed 3 clients in a 6 week period back in June. I reached out, and this is where the partnership with sales acceleration comes into play. There's about 200, and this is the first time I reached out for a sales expert to join me on my team, and I've done it in 3 instances.
Now I would say that the positives are working with someone else, getting to see how they do their consulting versus how I do it. It also helps me reinforce the way I approach it versus other people. I'm not saying the other people are wrong or right, but you got to do what feels comfortable for you and your clients.
But I think some challenges have been really getting your arms around revenue allocation. If you bring in a 1099, as a business owner, you've got tax implications also depending on the 1099. It also depends on how much work you have to do. So the goal would be to reduce my workload. But what I found at least initially, except for 2 of the 3, it's increased my workloads. I have to QC everything they do before I let it go to the client, and so I end up doing most of the work anyway. But now I'm sharing the revenue. So that doesn't feel good because I'm working with someone else, but maybe from a financial perspective, it might not be the best way to go at.
So I'm in the process of trying to figure out other models. I think potentially, it's probably finding the right people at sales acceleration that are really good at doing the work, but maybe not as good at securing the work and developing a partnership where I could sell us as a team. But there's some nuances to that, because we're all independent business owners. Everyone's going after business. And what if they land a client when they've already committed to your client. And now they're 1099. You don't really have control. So it falls back on your plate. So that's a long way of saying, I do a lot of thinking about it. It keeps me up at night, but I have not solved that problem yet.
AJ: Thanks for being open about it as it's a challenge yet to be resolved. But definitely one that's an issue.
Howard: Let me just share one other flavor that I've been thinking about is that sometimes I will take clients on as a part-time fractional, because I believe it will grow into a full time engagement. The tariffs were an issue earlier this year, especially in the manufacturing space, as I've moved through the summer and realized the workload of having 3 or 4 clients versus 9, just the maintenance and expectations. I think my mindset has shifted to probably less clients, more time instead of more clients, less time, because I think with the latter you just have more expectations. You're still doing a lot of the work, but now you're just doing it on less time, and you've got to be forthright with the client and be like, Hey, this is where we're at.
AJ: Plus 9 clients keeping all of that straight.
Strategic Problem Qualification
AJ: I want to go back to something we talked about when we met earlier. You have a great qualification question that you ask prospective clients.
Howard: So one of the things that is really important is not that they just have a problem. It's that they have a strategic problem that they need to solve. I think in this day and age for small to mid size, and I think a small to mid size, low end of 5 million and high end probably 200 million in that range. Give or take. There are a lot of things that people would like to talk to you about. They're looking for silver bullets on how they can increase sales, and I think everyone would love that if you could just pull it off the shelf.
But what I want to hear from a prospective client is they have a strategic problem, and they want to solve that problem because then they're going to put resources, time and energy behind it. Not just consider engaging me. So I look for those that have strategic problems. And they're like, I want to be that source to solve that problem for them.
AJ: I'm curious as to how you phrase that, because that is a qualification question. If you're not comfortable with sales asking that question is not comfortable. If you ask that question, you might find out that you've just wasted half an hour on a discovery call with somebody who, it is not an urgent problem that they really want to solve. So how do you go about it?
Howard: Well, I try my best. I'm not a hundred percent successful. But after you build rapport, and you start talking about the issues, I tend to just focus. And I'm like, where does this actually rise on your business plan as a strategic priority. And when do you want that solved? And what does that solution look like from a numbers perspective?
And once I get some of those answers I start to do if-then scenarios. So, if your problem is sales and it's a priority, what if we had to introduce some new processes? Would you support that. Yes, I would. What if we found out that you had the wrong people in the wrong seats, and we had to move people around, or maybe find a new person. Would you be willing to make that investment? Yes, I would.
And I'm asking those if-thens, because sometimes there are sacred cows in family owned, or smaller businesses, and if they say like Uncle John or Aunt Emily is in a certain position. And they can't be touched. Well, that could be an issue if they're not the right fit. So I want to know that going in to better understand the dynamic in the company, so I can manage expectations with the founder or family-run business.
Follow the Money Strategy
AJ: So you talk about following a follow the money strategy in your first year. What was your biggest fear about the follow the money strategy?
AJ: Tell me first backtrack for a moment. Explain the follow the money strategy, and then we'll get into what the biggest fear was.
Howard: Yes. So the follow the money strategy goes back to the first challenge which was identifying the right referral partners or centers of influence that could introduce me to founder led, or whoever's running the family business. And that's where I said, well, you got to follow the money in the sense of well, who are they going to complain about sales not being where they wanted? And usually I find my clients in 3 emotional states: disappointed sales going the wrong direction, exhausted, wearing lots of hats or discouraged because the exit's moving further and further away. So that's why initially when I was looking at the business referral network, I was like, Well, who are my centers of influence?
And I said, Well, business coaches would be so. Anyone with a Vistage group, or maybe they're running their own Vistage peer to peer group because they're hearing from 21-22, whatever it might be people in their group, and they're hearing common things. And they're going to want those people are going to want skilled people in each of the lanes that might be impacting a business so they can be a better resource to them. And the other person is financial, and that would be CFOs or fractional CFOs, because they know if this is a revenue problem, or this is an expense problem. And if it's an expense problem, they're just going to cut expenses. If it's revenue, they're going to say, Hey, maybe it's time we invest in sales infrastructure, sales people, sales processes, sales technology. And that's where hopefully I want to be top of mind for them that they'll make that introduction.
So that's the follow the money strategy. And so then, that's what I did, as I just looked to meet as many business coaches and offer to do lunch and learns, do speaking engagements with CFOs also just trying to let them know I was here. Participate in B2B networking groups. And then I think the first key with any business networking is to make sure you're giving and not just receiving. So I was fortunate. I have a pretty deep network, so I'm always looking for people to introduce other people to.
In my engagements I've brought in marketing specialists who are other referral partners. I've brought in HR consultants when there's been an HR issue. I have someone who just does client relationship management assessments and installation. So I'm trying to do that as well. Brought in a CFO into an account, a fractional CFO because we were growing so fast. One of the partners who was running the business was struggling with managing the money, so needed help there. So that's my follow the money strategy.
And I would say that probably challenge number 5 is allowing yourself the grace to continue the business development, even though you're probably uneasy because you have 4 or 5 other deliverables that you need to get done for clients. So it's a delicate balance between winning clients doing the work and continuing your business development, because at the end of the day, my goal is not to be with the clients forever. But my goal is to help them grow at some point. They're going to grow, either where they're going to have someone internally that can take over the sales management, or they're going to say, Hey, we'd like to have a full time person, Howard, can you go find us that person, onboard them, and then offboard yourself, so there's always an exit. I just don't know when that's going to be for most of my clients.
Client Sunsetting and Portfolio Management
AJ: You mentioned when we talked earlier, that you are sunsetting a couple clients.
Howard: That's my plan. That's in my business plan. I've got a couple of clients I need to sunset. I've got a couple of clients that I was just asked to do some recruiting and build infrastructure, and then coach and exit. So I think I have 2 of those clients that are ending in October, the other at the end of the year, and I've got another one that I think I should sunset. I've been there with them a couple of years.
My role is at a point now where I think they internally can take over my role, and even though it's not a huge spend for them, I think it gives them the confidence. And it does take me away for some other clients, so I'm looking to probably off board 3 or 4, and then hopefully bring on one or 2 here in the next few months. I've got a really nice opportunity next couple of weeks we'll see how that develops.
Most Surprising Podcast Question
AJ: You've been on several podcasts recently. What's the most surprising question you've been asked?
Howard: That's a good question. I'm gonna have to think about that for a second. I don't know. There's been anyone that's been most surprising. I think what is always taking me back is maybe what hasn't been asked. So when someone asks is like, okay, well, what does it look like when you successfully exit a firm? They don't really. They talk about the problem and the engagement. But they don't talk about what that exit looks like.
So from a metric perspective, I hope they now have the right processes in place. They're using the right technologies. They have the right people, and the business owner or owners has confidence. They have a sales operating system that can gain growth year over year.
But at the end of the day, what I think I'm really delivering is I'm changing emotions. We talked about being disappointed. Well, now after my engagements, we want them to be excited. They're no longer exhausted. They're engaged in their business because this part of the funnel or this part of the business is now working for them, and they are also anticipating what the future can be. So it gives them new lanes of opportunity, whether that be private equity, investment, strategic, family handoff, or just simply continuing to grow the business.
So I like to see that hopefully, that my business partners, my owners, have had an emotional change, and that it's not just impacted their work life, but it's impacted their personal life. And if I can deliver that for the majority of my clients, then I should be able to sleep pretty well at night.
AJ: You. It strikes me that you give them hope.
Howard: Yeah, I think maybe hope realized might be right. It's not just hope, but that it's now realized that they can attain the goals that they wanted for the business or their dreams.
Client Flexibility and Meeting Needs
AJ: And what's the question that you wish you would be asked that you haven't been. What question should I be asking you that I haven't yet?
Howard: I always love that question that's my most recommended sales coaching question at the end of a sales moment is, what question should have I asked that I didn't ask, because that's the catch all at the end. So I think the one question would be: how flexible are you, Howard, in helping your clients because you have to meet your clients where they're at.
And I think that the answer to that is highly flexible to a point meaning that I'm very willing to engage, especially when a business might not have as much to invest as I might be putting in it at the initial start, but knowing that business has a lot of legs into it, and that the business owner is very passionate about growing, and wants you to be part of that success story flexible to the point. The point is that sometimes they're not really looking for what they think they're looking for, and what I mean by that is, sometimes they come in like, well, just fix my marketing lane right? Or come in, and just fix my people.
Well, if it's a very distinct marketing issue, like they got to build a new website. Or it's more brand awareness, because that's how they think they're going to grow sales. Then that's not me. But I know a ton of people that can be, or if they have a lot of problem people on their sales team, and they're like it's more of an HR exercise than it is a sales exercise. And I'm like, let me introduce my HR partners first, let's take care of that.
Let them take care of that while I'm simultaneously helping to build the infrastructure. So it's trying very upfront to really understand where the owner thinks their sales issues are, and then really aligning your scope of work to that need.
AJ: What do you do when the issues that they think are the problem, after looking inside the organization, aren't really the problem?
Howard: I would say a lot of times, I'll be told, like my people stink they're not doing what they should in sales, and you get in there. And I mentioned early on that I'm a big believer in the business development ecosystem. So the sales plan needs to fill the business plan, and the marketing plan needs to ignite the business or the sales plan. And it's just one big ecosystem and a lot of times I've gone into businesses, and they don't have a business plan. They don't know where they really want to be 1, 3, 5 years out.
Well, they only want to make their number this year. Well, yeah, we can build a sales plan, but then it just becomes spinning it on a wheel. I want to know where we want to go. And what are those levers to pull us? And then the corresponding marketing plan usually is not aligned. Unfortunately, a lot of business owners look at marketing and sales in silos, but that's a true partnership.
Marketing's reason to exist is to generate leads for the sales team period. That's just what my thought is. I realize there are other great subjective values to have marketing. But if you're not feeding warmer leads in this day and age when people are educated before they raise their hand and say they want to buy. I'm not so sure it's the best use of spend.
And then the sales team needs to take that lead and the leads that they're self generating and be able to move them through the process through excellent vetting and creating sense of urgency and using subject matter experts, if needed, or anyone else on their team as needed when the appropriate time kind of quarterbacking them in and then closing the deal from there.
I think the biggest last point I'll make here fallacy that I see some business owners like: Well, we'll pay more for net new leads. We'll pay more for someone that's generating a cold call or an email. And whenever a business owner asked me that I asked them: can you point to one relationship where you are now working with a company or for a service or product that you got to solely by a cold call and you responded to that cold call. And now doing business with them?
And the traditional response is, well, I don't respond to cold calls. I'm too busy for that. I'm like, well, if you're too busy to do it in your own business. What makes you think that someone else in your client business that you don't know today is going to respond to cold calling. So I'm not a big believer in cold calling. I am a big believer in strategic outreach, which is where the partnership with marketing has to be hand in hand. It can't just be: Get a list. Make all these calls. That to me is not sales. That's someone who just wants to feel comfortable, that someone made a hundred calls, dials or emails today.
I've always managed my team to results. If it takes you 10 calls to get 5 meetings that you need: Great. Takes you 100 calls: great. I don't care about the volume. I care about the result, obviously coaching along the way. If you need to support development in certain areas, like conversations, relationship building, asking right questions. But activity based metrics solely alone, I don't think ever get the job done.
AJ: That's important words for consultants to hear as well in their own businesses. Howard, thank you so much for being my guest today on the thriving through podcast and that is a wrap for today's episode.
Howard: Thank you, AJ. It was a pleasure. Appreciate it.
