Coach2Scale: How Modern Leaders Build A Coaching Culture

What if everything you thought you knew about leadership was turned on its head? Join us for an enlightening conversation with J.D. Sillion, a two-time CEO and three-time CRO, as he dissects the myths surrounding leadership and unveils a powerful framework for guiding teams through both high-growth and turnaround situations. Drawing inspiration from sports legends like Phil Jackson, J.D. emphasizes nurturing potential over wielding authority to foster an environment where teams can thrive. Our discussion traverses the challenges of sales accountability and the critical roles of strategy, structure, and culture in achieving team success.

Imagine a sales process so efficient that each deal feels like a win for your entire organization. J.D. Sillion discusses the pitfalls of low win rates and their impact on morale and scalability, advocating for a culture of accountability. But what does it mean to truly empower autonomy within your team? J.D. explores the nuances between kindness and niceness, emphasizing the need for honest conversations that help team members grow. Learn about the success contract framework and how maintaining high standards can transform your organization and align teams with a shared mission.

Reflecting on personal growth and the mentors who shape us, JD shares stories from his own journey, highlighting influential figures like Lisa Gallagher and Sal Sylvester. Through personal anecdotes, JD reveals how overcoming ego and embracing continuous learning can lead to profound transformation. Whether it's climbing metaphorical peaks in business or contemplating the art of giving a TED Talk, J.D.’s insights are a masterclass in leadership. As we wrap up, listeners are left inspired to challenge the status quo, driven by the insights of thought leaders such as Greg Popovich, Jim Collins, and Marshall Goldsmith.

Chapters:
(00:00) Building a Culture of Winning
(12:16) Achieving Sales Accountability and Empowering Autonomy
(27:26) Leadership Lessons for Success
(34:39) Continuous Transformation in Business and Sales
(41:56) Navigating Leadership and Coaches

Takeaways:
  • Visionary Leadership and Team Success: JD emphasizes the importance of creating a compelling vision and fostering an environment that nurtures potential. CROs should focus on building a culture that supports team success rather than relying on authority or outperforming team members.
  • Strategic Framework for Transformation: JD introduces a strategic framework centered on strategy, structure, and culture. CROs can use this framework to guide their organizations through high-growth and turnaround scenarios, ensuring alignment with a clear vision and purpose.
  • Sales Accountability and Targeting: It is crucial for CROs to ensure sales accountability and target the right audience to enhance success rates. Focusing on product-market fit and maintaining high standards will boost win rates and morale within the sales team.
  • The Importance of Difficult Conversations: True leadership involves having honest conversations that drive improvement and growth. CROs should distinguish between being kind and being nice, where kindness means caring enough to engage in challenging dialogues for the benefit of the team.
  • Continuous Learning and Adaptation: JD underscores the value of continuous learning and adapting to new challenges, likening business obstacles to scaling Mount Everest. CROs should encourage a culture of perseverance, improvement, and embracing feedback.
  • Role of Mentorship: Mentors and coaches play a vital role in shaping leadership journeys. CROs should seek guidance from influential figures to transform their leadership styles and inspire their teams.
  • Autonomy and Accountability: Autonomy should be earned through accountability. CROs need to establish clear, non-negotiable KPIs and regularly review performance to foster a culture of responsibility and excellence.
  • Global Perspective: For CROs leading international teams, understanding cultural nuances and decision-making processes is essential. Tailoring leadership and sales strategies to fit diverse cultural contexts can significantly enhance global business operations.
Ways to Tune In:
CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Creators & Guests

Host
Matt Benelli
Co-Founder, CoachEm™ * Proud Dad/Husband * Entrepreneur * Leader * Coach * Risk Taker
Producer
Mike Montague
Founder of Avenue9, a Human-First AI Marketing Agency

What is Coach2Scale: How Modern Leaders Build A Coaching Culture?

Welcome to Coach2Scale - How Modern Leaders Build Coaching Cultures

Join Host Matt Benelli for conversations with management professionals in B2B companies who share the belief that effective coaching improves the performance of every team member. Our mission is to help leaders become better coaches.

Coach to Scale is sponsored by CoachEm, the world's first AI coaching execution platform that leverages evidence-based coaching to increase quota attainment.

0:00:00 - Matt Benelli
Welcome to this week's episode of Coach to Scale. Today we're sitting down with JD Cilione, a two-time CEO, three-time CRO, who doesn't play games Win rate under 50%. It's time to ask some hard questions. And let's be real a 20% pipeline conversion, that's not good enough, even if you're hitting quota. We'll dive into what it takes to build a culture of winning instead of a tribe of happy losers. Hint, it's not about handing out participation trophies. If you're ready to raise your game and connect with a community of like-minded pros who are pushing for excellence, make sure you engage with us on social media, share your thoughts, share your takeaways, be part of the conversation. Oh yeah, don't forget to hit that subscribe button on YouTube so you're the first to know when Coach to Scale episodes drop. Each week, let's go.

Welcome to Coach to Scale how modern leaders build coaching cultures. I'm your host, matt Benelli. Join me as we build a community of like-minded professionals who share the belief that effective coaching improves the performance of every team member. Our mission is to help leaders become better coaches. The Coach to Scale podcast is sponsored by Coachum, the world's first AI coaching execution platform that leverages evidence-based coaching to increase quota attainment. And with that, let's get started attainment, and with that let's get started. Today's guest brings a massive amount of street cred to the conversation. He's a two-time CEO, three-time CRO, results-driven leader, important results-driven leader. Currently he's an advisor. He's an investor and CRO at ProV International. Jd Cilian. Welcome to Coach the Scale.

0:01:46 - J.D. Sillion
Thank you so much for having me. I'm really pumped about the conversation today.

0:01:51 - Matt Benelli
All right, and I practiced my French accent JD.

0:01:56 - J.D. Sillion
Even you told me it was all right not to do that. Cillian is perfect. I usually go with easier, like millions with an S, so, cillian, but it brings me back to my roots, so I appreciate it.

0:02:06 - Matt Benelli
Like the forecast. We don't need millions, we need zillions. Maybe it helps.

0:02:13 - J.D. Sillion
I don't know. It depends on who you're asking. My team.

0:02:17 - Matt Benelli
All right. So JD myth buster question always starts us off here at Coach to Scale. What's a myth about coaching salespeople, sales managers that you believe is, you know, either misguided or maybe even complete BS.

0:02:31 - J.D. Sillion
So actually there are two that are very correlated. The first one is usually the idea that when I become the boss, people will finally listen to me. I mean just completely misses the point of leadership. As you know, true leadership is not about authority. It's really about setting the compelling vision that people want to follow. You need to have people that follow what you want to be able to achieve. So and I've seen this firsthand through the multiple transformations that you mentioned that it's at Inri, at Flatirons, at Nixea or even here at ProV Success come not from telling people what to do, but really from creating alignment around a clear vision and purpose that we all want to be able to achieve.

The second myth is that you must be the best player on the team to lead the team, and you see this a lot in terms of the behavior. Oh, you're the best AE, so we're going to promote you, and then, as you've been the best, you want to stay the best and being able to challenge everyone on how to do things in a better fashion. Think about Phil Jackson. I love the NBA and he coached both Michael Jordan, kobe Bryant, two of the best players of all time. Do you think that he dribbled better or played better basketball than they did Hell, no.

Leadership is all about creating the conditions that really enable those that will lead to achieve life-changing results. It's about developing capabilities and helping people realize their potential. So those are really the two things that are kind of complementary and that I think are still living out there when people get into those positions that they always want to be right and they want to be able to tell them what to do, and it's like no, build the vision, work alongside your team and just create the right environment for them to be successful.

0:04:15 - Matt Benelli
You know it, it it as a Boston, lifelong Boston sports fan and you know, bostonian, it pains me to hear Phil Jackson's name being brought up so many times. He's probably got the most coaches. You know, bostonian, it pains me to hear Phil Jackson's name being brought up so many times. He's probably got the most coaches you know named in the 70 or so sessions that we've done. But obviously great. I always forget that he coached Michael and Kobe, which is amazing.

0:04:41 - J.D. Sillion
And I have other coaches, so when we're going to the coaches section I have other names for you that are not into sports.

0:04:46 - Matt Benelli
Well, you probably don't have Red Auerbach, and he was probably the best coach out there, and he definitely wasn't the best player on the court. I don't know if he was five feet tall, all right. So, jd, there's a lot of talk about coaching. Everybody's got their own definition. You've led turnarounds. You've led great growth stories. You've had to coach a lot of different types of people. Do you have a definition that you use a framework?

0:05:13 - J.D. Sillion
So, as I mentioned, the definition is really coaching is about creating the environment for success. It's helping people recognize and seize the opportunities within those environments. Recognize and seize the opportunities within those environments. So, from a framework perspective, that's something that I've developed over the year, leading, as you said, both high growth and turnaround situation. So every time I get into either a new organization or a new role, or I have a leader coming into a new role of his own, I say, hey, let's do the same type of 90-day framework, which is around strategy, structure and culture. So evaluating all of those three pillars and the key here is that you can't just look at the numbers, you need to understand the ecosystem that produces those numbers. So what that means.

As an example, at In INRI, when I joined them, they were facing a perfect storm. It was the tail end of COVID and, as you know, from a sales perspective, covid disrupted completely the traditional way of selling the different selling models. Our partner relationship with ServiceNow was really in need of work and we also needed to transform the business to be able to have an exit that was planned within the next couple of years. So the secret itself is not in one specific or single action. It's really into that systematic approach to transformation. So, strategy as an example we looked at our market positioning, particularly again, our relationship with ServiceNow, and what we found very interestingly is that we had really strong technical capabilities but we were not playing where we needed to. We were not effectively communicating our value to the ecosystem. Proof is win-loss. Our win-loss ratio was below 50 percent. Low 40 percent, that was was telling us something very specific about our market approach and our fit.

Second, the structure we assess. I always assess the team in terms of capabilities, in terms of the sales motions and, same thing, we discovered that we had great talents there, but we need better alignment between our sales process and what the customer buyer journey looked like and what really mattered to them. And our deal size same thing. The size of those deals was very indicative. They were much lower than what the competition and what the market really could bear. And even some of our sponsors within ServiceNow were like you guys are leaving money on the table Because, again, you're not articulating enough of that value.

And thirdly, it's culture, and culture is crucial when you're looking at transforming a business. You want to be able to build this high-performing team and building that high trust and usually, when teams are not necessarily performing at their best, it's because there's a lot of drama within the workplace and usually that drama comes and stems from misalignment Misalignment either in terms of the expectations, in terms of the commitments or in terms of the communication and, as I said, all of those are not theoretical. At Flyerance, that helped us grow from 26 million to close to 200 million, getting also a glass door rating from the low twos to the high threes, and at Inry, grow our win rating from the low to the low twos to the high threes. Uh, and it uh plus uh. You know, at inry, uh grow our win rate from the four low 40s to the 55 plus and grow and almost doubling, or actually more than doubling, our deal size uh average. So, um, that's those are really good, strong frameworks for me to uh to look at every single time.

0:08:42 - Matt Benelli
Great and I love that strategy, structure, culture and the examples. One thing I want to dig into a little bit there, jd, is you talked about the low win rate at 40%. You grew it to over 50%. I've worked with a lot of companies over the past decade who had win rates in the lower, let's low, like see 20, and they were ecstatic to get it to 30. Um, you're laughing, which means you've heard this before. Um, oh yeah, what are you? What are you? What are your thoughts on those win rates like the being okay with a 25, 30% win rate?

0:09:28 - J.D. Sillion
So I don't want to hurt anybody's feelings, but usually I categorize organization into two camps winning organizations and happy losers organizations. And when I say this is again when you come from a DNA of scarcity, from a leadership perspective, where you're more comfortable with expanding your coverage, having a 5x pipeline and then allowing your organization to be at a 20%, 25% close rate, this is just creating a culture of happy losers. And the issue with this is that we were talking about sports earlier. Why do sports professionals how are they getting better and better and better? Practice, practice, practice, being challenged and practicing and doing and repeating. So we're talking about that, we're talking about baseball, we're talking about football, about basketball, the number of free throws or shots that they take.

So you get better at the things that you do the most, the more often If you lose, more often than you win, guess what your team gets better at losing they don't get better at winning.

So that's for me something that is extremely unnerving to be able to see that, culturally, over the last five to seven years, on the sales side, we have pushed those organizations. Sure that you look at those numbers and those numbers are telling you a story. And what do you do about that story and how do you get better at it? Because, again, what you want is being able to identify the areas of that sales journey and being able to get better at it. So, as I said, leadership seeks comfort in coverage, increasing pipeline, increasing volume of activities, activities volume, volume versus the quality of it, additional market segment, additional geographies. It's like scarcity versus abundance. Become the best that you can be at a few things versus being average on multiple things has always shown to me to be the best path to sustained growth on multiple things has always shown to me to be the best path to sustained growth.

0:11:53 - Matt Benelli
So in our initial conversation, you had a quote that I really loved, and you referred to it just now. The numbers are telling you a story. Are you listening? And so let's use an example. If an organization has a 5x pipeline, but they're converting at 20%, what is a likely story that those numbers are telling that organization?

0:12:17 - J.D. Sillion
So a few drastic stories. The first one is if you're closing 20%, it means that 80% of the shot that you take you're not making, which means that it costs your organization 80% of the time that they spend supporting you on the sales side, or 80% of the time that you spend as an AE is non-fruitful, does not bear fruits. So first, yeah, there is a lot of wasted energy and wasted capital. The second is who are you talking to and what are you selling to them? Because clearly, what you're offering to them does not resonate. So either you're talking to the wrong people so it's a personal issue or you have a product market fit issue.

0:13:08 - Matt Benelli
So, okay, product market fit. Talking to the wrong people. And this is maybe where your experience as both a CRO and a CEO multiple times comes in. Because what if the eight year you're only hitting 20% of the shots that you're taking, but it's enough to grow the business sufficiently, it's enough to achieve the number? Then what do you do? Do you do you go solve another problem somewhere else, or is this problem still worth digging into because you can be more efficient and perhaps even do better?

0:13:48 - J.D. Sillion
So in my opinion, it's a question of scalability. So if you again, if you do a 20% in order to be able to hit your next threshold of growth, look at the additional cost and pain across the entire organization. It's not just about the salesperson, it's about the marketing to be able to get all of those different leads. Then it's about sales sales engineering. Then, when you pull additional folks from from your delivery teams or professional services, it does not scale well. Also, it that 80% of the interaction that you have. You're not creating advocates, you're not creating raving fans. You're leaving a bad taste in somebody else's mouth versus being able to again create that momentum. So when you're talking about growth, yes, you can hit your numbers, but you're not creating the momentum that's going to really open, stick that momentum. So when you're talking about growth, yes, you can hit your numbers, but you're not creating the momentum that's going to really open, stick that growth. You're just going to barely make it and expend a lot of capital to be able to do this.

0:14:56 - Matt Benelli
Right, and eventually there's burnout, there's bad morale. There's a lot of things that come into play there.

0:15:04 - J.D. Sillion
Yeah, and I was about to say and culturally again, what you're doing is that, yes, you meet that numbers, but more often than not you lose. Which, again, as a seller, as an individual, if every single day you go and you know that you're gonna lose more than you're gonna win, it takes a toll on you, it takes a toll on your mental health, it takes a toll on your energy, it takes a toll on your desire to get better, because you don't see necessarily that traction, that positive momentum to be able to grow.

0:15:38 - Matt Benelli
So, and from our initial call, I know you love the devil's advocate, so there's a saying out there Maybe it's my saying, I don't know. I've stolen everything I've learned from someone else. But even the best salesperson in the world wins more than he or she loses. Or even the best salesperson in the world hears no more than they hear. Yes, I've parroted that and believed that for many years. Maybe I'm wrong. It sounds like you have a different opinion there, so it depends where you are in your process.

0:16:17 - J.D. Sillion
Okay, From a sales perspective. So for me, your goal as a seller it's to get to either a no or yes as quickly as possible. But if it's a no, get it much quicker in your sales process. That's why qualification early and often throughout the sales process is critical. You do want to hear no if that's going to be the outcome, but you want to hear it very, very early on, before you expend too much energy your own energy, in your own time and all the organization's time and energy. So yes, it's. You will hear certainly no more often than yes. But the way I calculate my win-loss is once they've done through a couple of stages of discovery and validation, Because here those are good no's. I want the no's in that stage one to stage two. Once you're moving to stage three and start involving additional costs internally, then you better have a really, really strong win-loss ratio.

0:17:20 - Matt Benelli
A hundred percent, yeah, I mean if you're, if you're a 30, 40%, uh, 50%, even, that you know at that committed stage, then you got, you have. You have other problems, you get big, big problems, yeah for sure. So when, um, when there's problems, there needs to be accountability. I don't want to presuppose that you agree that there are problems in many organizations holding people accountable, but that's been my experience.

0:18:02 - J.D. Sillion
If you believe in that, why is it so difficult for sales leaders to hold their people accountable? Keeping people accountable it's tough, it's not very pleasant, it's also a little bit unnatural, because we are beings that really like to get along and have that sense of community. So the way I look at it is, there is a crucial difference in between being nice and being kind. Being nice avoids difficult conversations. Being kind means caring enough about them to have those hard conversations. So what you want as a leader is learning to be kind with your team, because we were talking about, culturally and behaviorally, how the organization kind of creates itself. Your culture ultimately becomes the worst behavior that you tolerate. Can you say that? I'm sorry? Can you say that again? Your culture ultimately becomes the worst behavior you tolerate.

0:19:06 - Matt Benelli
Wow, your culture eventually becomes the worst behavior that you tolerate. That's powerful stuff, explain.

0:19:15 - J.D. Sillion
That's why you have to have an accountability framework. So if you're saying, hey, as an example, what I do with my team is I usually draft a success contract framework. Actually, I learned this at home with my kids and then I applied this in the workplace. But that success contract framework is hey, let's agree on some very clear, non-negotiable KPIs. So we know that our revenue number non-negotiable.

Some level of activities that we've been are critical for the success of what you're doing are non-negotiable Personal development goals, because if you don't take care of getting better doing the work, learning and honing on all your skills, you're not going to be able to produce better Key contribution that you need to do for the team because, again, sales is not an individual sport, it's very much of a team sport. And then, just as I said, some of those critical activities in terms of how many times you need to go and meet with your prospect and be face to face, or being able to meet with your partner, and things like this. So if you do not measure regularly what you've agreed upon that yield success, then you're just talking. So you want to be able to create that accountability by reviewing, reviewing, reviewing what really matters and then being able to stay accountable. Most of the time, people are going to push back and say, hey, I've been doing this for quite some time, Leave me alone. Autonomy is earned Autonomy is earned.

0:20:55 - Matt Benelli
Yeah, I want to just frame that because I was going to segue into. I remember one of our conversations you talked about how autonomy needs to be earned and I'd love you to expand on that. But also, jd, because you've had experience leading teams across the globe, right? China, india, the U, us, like they're all different, and I know that a lot of people, a lot, a lot of my peers, a lot of my friends in this business, a lot of my clients, people that I have on the show, talk about one piece in their leadership repertoire that is missing is international experience, and so it's nice. This might be interesting for people. When you talk about autonomy is earned, explain it the way you're going to, but can you also talk about that in the context of what you find different in cultures, leading teams across the globe? Does that make sense?

0:21:51 - J.D. Sillion
Yes, it does. So let's go with the autonomy is earned and then into the international portion. So let's go with the autonomy is earned and then into the international portion. So on the autonomy is earned. It's when we're talking, for example, about KPI or financials in general.

I had one of the most, one of the best mentors, jeffrey Goddy, who was CEO of Flatiron for me, now is CEO at Quadient in Europe and in the US, and he would be drilling us all on our P&L from top to bottom, but not for the number, for what the numbers meant Meaning. Do you understand your business? Do you understand why that number is the way it is? I don't. He didn't really care about the number, that it was good or bad, that was a different conversation. But if you're not able to understand what the number meant for your business, for your people, for your customer, what drove that number, he would just keep asking, asking, asking, asking, asking. So you have to become a really, really deep understanding of what your business was and when you showed that you had that understanding and you would understand really the dependence of the different decisions, then he would just leave you alone. That again your result might be up down, up down, then he would help you strategically on how to get better. But to be able to get to that next set of conversation, you have to earn that next stage by showcasing that you were doing the work, you were understanding it, you were articulating it and you were in control. So for me it's the same thing from a sales perspective. You want to be left alone. Show me that your pipeline is growing in the way it needs to, that it's qualified in the way it needs to, that the level you're maturing your different deals is effective and that your win-loss keeps increasing and your average yield is also increasing and your customers are happy with us. If that's the case, of course I'm going to leave you alone. I'm going to come and just help you as much as possible, but I'm not going to go and challenge you every single day. But if I see that you're at 15%, 20%, I see that your pipeline is 5X, but you keep pushing the date five, six, seven times, like we talked about, and your win-loss is abysmal, well, I'm not going to leave you alone, first of all because that would be a disservice to you as an individual contributor, because you want to be able to be helped so that you're successful, but it's also because you've not yet earned the right to just fly on your own. Let's work together to be able to get you there.

Now, on the international portion, culture is, uh is very, very uh important. We've talked about culture and, and the way decisions are made, the way even buying decisions are made, are very different from one continent to the other, so I don't think that there is a a silver bullet there. Um, the culture map uh is a fantastic book. I have it somewhere, the culture map fantastic book that really explains the different cultures, the requirements that you have to share in terms of the level of context to be able to make a decision, and things like this. So what I've learned, especially being originally from Europe and French.

So when I moved first to the to the us, in french, you, you debate, you look at the information for a long, long time. You do a lot of analysis before you make a decision. In the us, you look, but you you say, okay, let's try something, and then, if it doesn't work, we'll adjust, because action is preferred in the us versus overthinking. So when I came to the us, they were like do you need to make a decision? Let's, let's go. You know we're not going to be looking at this for forever and ever. Um then?

So I did this for for many years and when I went back to Europe, and especially in the northern country, if you make a decision in the Nordics and then you change your mind, the belief from the team is that the boss is not in control and doesn't know what he's doing.

So you can't do that. So you need to be able to balance, depending again on the geography how best support the team, based on their own needs and based on the way they are making decisions, based on the way they are digesting that decision as well. So there is no silver bullet, because we talked also about Asia, india, china, where a lot, of, a lot of the team members are going to say yes, yes, yes, even if they are struggling in delivering the outcome. So you need to be able to create I think it always goes back to the same thing you need to create an environment where people feel heard, they also feel like they have an impact and they have a path to be successful. If you do those things, they will tell you how to best engage with them.

0:27:06 - Matt Benelli
Makes sense. It makes a ton of sense and thanks for sharing that experience. And it sounds like the culture map for those out there that are looking to understand how to work with different cultures, different markets. The Culture Map might be a good book to learn more about that. Great Love the book recommendations.

Going back to accountability, I took a note here. You brought something up at the end of making your point there and you said if we don't have those let's call them tougher conversations, we're doing a disservice to the, to, let's say, the salesperson. We're doing a disservice to that person because that person wants to get better and if we're not giving them the feedback, we're not having that tough conversation. They're not going to know what they're doing wrong, they're not going to get better. And so you could extrapolate that to say if we don't have the, the, if we don't hold people accountable, we're not helping them. Maybe expand a little bit more on that, because you know these difficult conversations that's another topic lately. It's why do? Why is it so hard to have that? Let's call it difficult conversation? And what we find all too often is that leaders know they need to have it and they know, but they kick the can down the road. Yeah, it's.

0:28:33 - J.D. Sillion
You know, we most, most humans are. They try to avert conflict and they feel like having that conversation is going to be a conflict and because they are not comfortable with having that conversation, they are not going to prepare necessarily very well and they're going to be a little bit awkward in helps. It is going to turn into a conflict that's not going to be heard and it's going to leave a bad taste and a bad experience at both the receiving end and the leaders that try to share that information connect to childhood memories of either a coach or friends or anything like this, where the best memories that I have growing up I played a lot of tennis have been with coaches that were hard on me. And they were hard on me not because they were mean. They were hard on me because they saw that I could do better and they were challenging me to do to do better, and it came across as I know you can do better, but right now you're not doing your best. Run around the court a few more times and then we'll go to go to go to do the practice again and if you don't hit the target five times out of ten, you'll do another one, because I know you can do it because I've seen you do it.

Um, and it's hard and it's painful, but those are memories where you felt and you knew you were growing, you were getting better. That's what your team members deserve. They deserve your slight pain and discomfort to be able to grow. They've earned that right. Every day you wake up and you decide to go to work. It's a choice they're choosing every day to trust you with the biggest part of their day and their livelihood the biggest part of their day and their livelihood. The minimum you can do is just show up for them and be kind and help them be successful.

0:30:43 - Matt Benelli
You know, when you first talked about I think it was the difference between being kind and being nice. If I, the first thing I thought about was how, how much coaching and leading in business and sales has to do with parenting. Right, the overlap is there. And then you brought about the success contract that you have with your children, which I think is pretty cool, jd. You've been doing this a while, which means you had a lot of success, but you also probably stubbed your toe a few times. What's a painful lesson in in uh in your career that you learned?

0:31:22 - J.D. Sillion
that's helped shape how you approach things today you know so many battle scars so it's, uh, it's like any success. No, gray hair.

You're doing all right oh no, no, I, I, I do. It's just a good lightning lighting, um. But it's like anything else when you, when you, when you see the success, you cannot forget what's below the iceberg and all the pain, um. But some of the key things that I've learned is really listen and be humble enough to hear it, um. So it's very important because I think, and I'm a firm believer, that the universe is going to offer you all of the opportunity to learn the lessons that you need to learn to be able to grow. And most of the time, when there are things that keep coming back, I keep telling myself what am I still not learning that the universe is putting the same challenge in front of, in front of me.

Early in my career, I kept getting the same feedback over and over again, which was you're not being promoted as the first one or you're not receiving the feedback from your peers that they would prefer you to lead them versus somebody else, and I was like I don't understand, because I'm doing all those things and I think that I'm doing a good job, uh, being able to do abc and d with them, um, and the best thing that happened to me is getting a coach and the coach to help me get with a 360 as to how was I perceived versus what I was doing, and there's usually a big delta in between your intent and the way it's actually being received. And those are very hard lessons to learn, because you're like, hey, I'm having that conversation and my intent is to be able to convince you of abc, and then the actual result is that person is actually pissed off and he's never going to do this and, on the contrary, he's going to do something different. Um, so those have happened quite a few, but the three things that I've learned throughout all that journey is you have to embrace the work. Success just does not happen.

I often post about this as well, but if you're improving your close rates, your ARR, your team performance, you have to do the work every single day. The second is that you have to stay hungry to learn. So learning is critical, that it's learning about your skill set specifically to selling, that it's becoming a better human, better leader. So what worked yesterday may not work tomorrow, so you need to be able to keep refreshing and keep accelerating that absorption of the information that is out there. So being able to maintain that learning culture is critical.

And the last one is just focusing on creating the conditions for success for you and for your team. If you don't do this, even in your own environment, how can you lead others to success? If you don't take enough time to be able to again recharge, to be able to learn, to be able to have your own sets of accountability charges? Did I do this? Did I not do this? Did I show up the way I wanted to? Oh, I did not. Why? What happened? What were some of the triggers?

How many times do you have a conversation and your ears kind of really start getting warmed up and you get really intense and then your voice change and then you don't get the result that you were expecting because you lost track. Take a minute, look back and say, okay, what happened? What was said? How did that trigger me? Why did that trigger me? And usually it always comes from ego. I mean 90% of the time, ego keeps like talking and it's like, oh, they didn't like what I had to say. And again, going back to I need to be the best, and it's like, no, you don't have to, you can make mistakes. Just embrace it. Everybody's trying to do the best that they can. Just have the conversation. Grow together, create that condition for mutual success.

0:35:27 - Matt Benelli
Your ego is not your amigo. Your ego is not your amigo Love that the took from the 360 and those three key areas that you learned to help you be more successful. So you're doing a lot of different things these days. You're at ProV now as CRO. What does ProV do and what excites you about doing what you're doing?

0:35:55 - J.D. Sillion
So ProV is an implementation specialist, implementer, specialist of the platform ServiceNow, love ServiceNow and the technology and what they do out there automating the rhythm of work and leveraging AI in many, many ways in the organization. It's great technology. Customers are happy with it. So, as an implementer, you have to do the best job that you can to be able to get that momentum of adoption going. What I like about ProV is that it is a transformation story. So it's how do we get better at differentiating ourselves? How do we get better at servicing our customers? We get better at servicing our customers. How do we get better at delivering value faster for our customers in a very, very, um, competitive environment? So that's I. I love transformation, as you can hear. I love to be able to challenge uh organization to become the best version of themselves. So that's that's what it really, what really gets me up and gets me fired up.

0:36:59 - Matt Benelli
And and you've been in. You've had success in the transformation game and you've also had success in the growth game. What, what is it? What's the difference between the, the you know, if you're going to join this organization that needs a turnaround, versus this organization that just needs to go from like good to great? How do you approach those differently?

0:37:21 - J.D. Sillion
you know the the core fundamentals are the same. It's still a transformation journey. It's just that the parameter of that transformation. They are different, okay, because there are areas where just it's broken and you need to fix it. The other one is it's working. You need to make it work even better. The other thing is sometimes, especially when you're in high growth, you're actually fixing multiple engines in an airplane while you're flying because there are multiple engines of growth. When you turn around, you're kind of working on one engine to make it actually start and start running. Um, so it's all. It's the same thing as what we discussed earlier. It's looking at the numbers, finding the numbers that are going to give you the best thread to pull on to be able to better your business. But it's always a transformation again, what got you here Is not going to get you there From Jim Collins again. So same thing you want to be able to keep pushing the envelope.

So how do you get better? Better in terms of your pre-qualification from the market, from an MQL to an SQL? How do you get better on your SQL to be able to turn them into full opportunities? How do you get better to have a higher win rate, a ratio into full opportunities? How do you get better to have a higher win rate, a ratio? What are the right level of user stories and qualification stories that you can put in on with your team? So you're never there. Your objective always changes. So even when you get better, you had an objective of, for example, 100 million with X amount of growth and you get there. Guess what, as soon as you got there, the goal is completely different. So you always have to go and find this next threshold. That's what is exciting in those environments is that, no matter what, it is a transformation and you have to look at the patterns that you have to either break or tweak.

0:39:20 - Matt Benelli
JD, it's funny that you bring up the summit, the top of the mountain there. I talked to a guy one time who was in our business, you know, like you and I do, and he climbed Mount Everest. I was really intrigued about it. I was asking him a million questions and he comes and says he's like look, it was tough, I trained for it. But here's the difference I trained for it. I got there, you know, thankful it was a good weather, you know, the winds were blowing our way, so to speak, and I was successful. The reason why leading businesses is much more difficult is because when you get to the top of Mount Everest, they create another summit. You never get there. He's like Mount Everest is always going to be the tallest summit in the world, but they always create bigger mountains in sales and in business. I thought that was kind of funny.

0:40:14 - J.D. Sillion
Yeah, I mean, what's really tough about sales is that every year you're trying to get to the best year that you've ever had. Every single year, you're trying to get to the best year that you've ever had. I mean, it's the most challenging area of all. You always have to get just a little higher, a little higher, a little higher.

0:40:38 - Matt Benelli
So true, so true. So we've been talking about coaching and you referred to some folks along the way that helped shape who you are and what you do today. But can you because we're Coach to Scale, we believe, I believe that people who care about coaching and developing others and focusing on leveraging that force multiplier to achieve organizational scale, they've had that behavior modeled for them somewhere along the way. Can you share about someone whose coaching has had an impact on you?

0:41:11 - J.D. Sillion
So I mentioned Jeffrey Godet earlier. I mentioned Jeffrey Godet earlier so he was one of the most impactful, just because he's a visionary in the way he looks at business and he's very keen on empowering his team. So he gave me a shot when I needed one. He helped me grow, he helped me trust myself, challenged me, as I said, by putting me in very, very uncomfortable situation that he knew I could handle and just say, hey, go for it. And being able to take the training wheels out when needed. And but he was also very keen on flagging all the different weaknesses that needed to be addressed. So you know, having those kind conversation was part of what I learned with him.

Lisa Gallagher was another person. Earlier in my career at Higher Right. She was a crucial mentor. She also taught me what real leadership looked like. She was very, very tough, but she was even more caring about the person and their success. So she really helped me understand that leadership is all about taking responsibility and backing it up with actions.

The last one that comes to mind and I got plenty. I even wrote articles about my mentors and angels along the way but Sal Sylvester was my first formal coach and he was really instrumental in helping me transform key beliefs and behaviors that had a really a huge impact on on me and the way I was showing up, and and for that I could not be more grateful, because it it was really hard to get this mirror put in front of you and be like, hey, your intent is here, but here is the impact that you have, and you're like, oh, what happened? Let's course correct this, and those are tough conversations, but if you don't have them, if you're not being again coached to be able to get there, you keep repeating kind of the same flavor of the issue if you don't have that transformation.

0:43:16 - Matt Benelli
Awesome, wow. Thanks for sharing all those different coaches and mentors in your life and the impact that they had on you. Speaking of coaching, who's your favorite coach?

0:43:30 - J.D. Sillion
So you certainly have heard having your people in your bookshelf or in your kitchen cabinets, being able to have all the people that really have an impact on you and being able to grab information and concepts from them. So I have a lot of coaches that I look upon. I've named Jim Collins earlier in some of the conversation. Marshall Goldsmith as well has been fantastic of the conversation. Marshall Goldsmith, as well, has been fantastic. Patrick Leonsini is one of my favorites as well, because he makes those concepts that are so complex so digestible. And then I spend a lot of time on podcasts, so that's why I love being here with you. I have people like Ryan Hawk, david Novak, ken Parrish. I mean those guys just bring so much value every single week that it's very important. Last but not least, it's from Atomic Habits, james Clear. Yeah, so so good.

So there are so many different concepts that I take from those guys. From James Clear, it's the hats, the haircut hats and tattoos. You know, in terms of how do you make decisions that are going to have a lasting impact. From Jim Collins, it's the bullets versus the cannonball. So when you start mixing some of those concepts and you're like, okay, let's put a hat on and let's do a couple of bullets here to be able to try a new concept. It's not going to hurt us and again, it could be a marketing campaign, it could be a new way of going to market, but then you go into a pilot and then you do a very stringent strategic shift. So being able to apply some of those concepts I think is really important. So I can't just bubble up to one favorite coach. I think you need to find people that resonate with your style and being able to grab on and keep expanding that focus that you have.

0:45:30 - Matt Benelli
I love where you went with the question because you went in a direction that speaks to what a lot of us in this business listen to right, the, you know, the James Clears, the Jim Collins of the world, et cetera. Let me ask the question a different way, if I may. Yeah, you talked about Phil Jackson before you're a tennis player. If you think about coach in the sense of a name, just about everybody would know, in the sense of a name, just about everybody would know, like you know, whether it's a sports person or some other person. Way, you know up there what is a who's a favorite coach or a coach you really admire that comes to mind, and what attributes about that coach's style interest you?

0:46:17 - J.D. Sillion
So I'll stay with the NBA, I'll go with Greg Popovich, and the reason being it was just the composure that he had and he was known for once in a while telling Tim Duncan hey, I'm going to get a technical and get thrown out of the game because the team needs to be shaken up, so you're going to go in and coach them for the last five minutes of the quarter. And then he would go and blow up in front of the referee and everybody was like, oh my God, wait, no, no, it was all calculated, because this is just not his personality. But he knew that that's what the team needed and being able to manage that team. And if you look at the Spurs during those years, they were a humble, hardworking team Compared to all of the other superstars. Now they're just a very different culture.

0:47:13 - Matt Benelli
Love that team, love that whole thing. Tim Duncan love how they approached the game and their business. So does that mean like for for people watching this that work with you? Like when you blow up at them? It's just a charade.

0:47:29 - J.D. Sillion
So when I'm really in control, that can happen and sometimes, like anybody else, my ears are are warming up too much and then I lose a little control. I'm like, oh my gosh, why did I do this? This is not the best version of myself. Like anybody else, most of the time I'm good and once in a while I'm not the best version and I keep learning, and that's still something that the universe keeps putting in front of me. And I'm very passionate, but really then, because when you're too passionate, you're not getting your message across.

0:47:59 - Matt Benelli
I think there's a lot of people out here that will resonate with that comment. For sure, jd, if you had to give a TED Talk on any topic, we've covered a lot of ground here. If you had to give a TED Talk on any topic related to leading, coaching, telling people, what topic would you choose them on?

0:48:14 - J.D. Sillion
You know it's a tough question because I love coaching and leadership so much, but I think the theme today was really results. So results or speaking, are you listening? Would be kind of my TED Talk, and I would look at some of the key learnings from my time at Inry. As an example, with those low win rates, and what does that tell us in terms of market fit? How do you get better from a partner-influenced deal increase? How do you get better from an average deal size? Because, again, if you don't have the right value proposition, the right messaging, so again, every time, as I said, the universe is giving you hints. So results are speaking very loudly, but are you listening?

0:49:01 - Matt Benelli
I love that Results are speaking. Are you listening? Is there a question I should have asked you, but didn't?

0:49:13 - J.D. Sillion
So you know, earlier I talked about the success contract and I told you it was coming from my kids. I think the question is are your kids high performing team of teenager? And the answer is no. I have still a lot to learn there. So, but joke aside, it's. I think one of the key learning area is when you understand that it's at home or that it's within the workplace. It's not about you. It is not about you when you do coaching, when you do leadership. It is all about the other person, and that's why we talked earlier about ego is not your amigo. It is so true because it's nothing that you're going to do. It's all about they most of the time. Of all the answers, it just needs to have someone that cares enough to be able to help them take the next step. It's just one step at a time Incremental upgrade 1% every day, as James Clear would say 1%.

0:50:14 - Matt Benelli
Better every day, for sure. And you, you ended that sentence much differently than I thought you were. So that was the ultimate pattern interrupt. I thought you were going to, like you know, pump your kids up. You fell on the sword there like a real parent. So it's always a work in progress.

0:50:34 - J.D. Sillion
It sure is.

0:50:35 - Matt Benelli
I have a 23-year-old and a 25 25 year old.

0:50:38 - J.D. Sillion
And we have the same as the business every, every year, every day. It's a little bit more, it's a different challenge.

0:50:45 - Matt Benelli
And I've gotten a few times dad, is it ever good enough? You know, and it's like you know. You know, of course it is, but you know, I don't want to tell you that all the time it is. But you can do better. Yeah, but you can. Yeah, but you can do better. Beatings will continue until morale improves. No, I'm just kidding. All right, jd, we covered a lot of ground. We talked about accountability, we talked about the importance of culture, we talked about the importance of getting feedback and acting upon it. The results are speaking. Are you? Are you listening? Um, we talked about, you know how to approach a growth story versus a transformational story. Um, just a lot of different things today, and I really appreciate the energy and thoughtfulness that you brought to the conversation.

0:51:33 - J.D. Sillion
so thank you very much well, thanks, matt, for having me and I hope I hope that people will enjoy listening to us.

0:51:42 - Matt Benelli
Well, I enjoyed the conversation, so you know. That's that's why I do this. No, just kidding. I know people are going to take things from this and be and you delivered the information in such a way where people can hear something and then take action on it, and a lot of folks that listen to podcasts and a lot of folks certainly that listen to this podcast that's what they're looking for there. The jobs are hard out there, right, being a frontline sales leader, being a sales director, being in sales, like you said, it's super difficult. People are looking for that extra edge, something to make what you know the job they're doing. That's really hard. A little bit easier. How to get a little bit better. So thanks for helping them get that 1% when they listen to it. So, all right, and for everybody out there watching and listening, thanks for doing that.

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