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Empowering Others Through Mentorship with Will Milano

“Leadership is about empowering others and maintaining focus on the horizon.”

Will Milano, the CMO of Integrity Solutions, was thrown into his first leadership role with no training but was lucky enough to have a manager who instilled confidence in him. He understood he needed to do the same for his team if he wanted to excel.

In this episode, Will talks about the mental shift every leader has to undergo, going from tactical work to focusing on developing others. By empowering his people and balancing short and long-term strategies, Will is able to lead his team to success. Listen in to hear how to unlock the potential of those around you and become an inspiring mentor and leader.

After You Listen:

Key Takeaways:

  • Empower others as a leader to create independent problem solvers
  • Build strong relationships across departments to ensure a successful marketing strategy
  • Find yourself a mentor in someone you trust to maintain a fresh outlook and enhance your business tactics

Things to listen for:

  • [02:52] Lightning round with Will
  • [08:55] Will’s first leadership role
  • [16:41] Effectively communicating as a leader
  • [21:25] Marketing strategy vs. business strategy
  • [25:23] Advice Will would give to his younger self
  • [28:10] Craig’s takeaways


[00:00:00] **Craig:** Far too often we place people into leadership positions because they were strong individual performers, and we believe, well, if they were successful here as a solo performer, they certainly can lead a team.

[00:00:14] **Craig:** That is not always the case, and it is always the case that to be successful, that leader’s going to need mentoring. They’re going to need guidance, they’re going to need coaching and training. Leadership is not a happy accident. It’s something that takes intention and effort.

Welcome to Executive Evolution. I’m Craig Anderson and my mission is to equip accidental leaders like me with the confidence, confidence, and calm to level up their leadership.

So I’ve had several experiences in my both coaching practice and my work experience where we did, I came up through sales and in sales organizations. It’s the curse of leadership. We see a strong salesperson who hits their numbers, who blows things outta the water. They’re an A performer. They wanna feel like their career’s moving forward.

We want them to feel like their career is moving forward. So we promote them into these roles and they think that what made them successful, if it was grinding or whatever it was that they did to be successful as a sales rep, they just need to do those same things as a. And what we have to step in as, as their senior leader or as a coach working with them.

We have to step back and say, let’s take a look at those things that made you successful and pull back from them and really understand how do you develop that into this new leader so that they can start to. Realize the importance of things like communication and vision and accountability and all the things that are part of being a leader.

So it’s important that we step in and provide those development opportunities and those growth opportunities.

[00:01:55] **Craig:** And in today’s interview, will talks quite a bit about how the support of a mentor helped him to develop the confidence, helped him to set priorities, helped him to become a better leader. So why don’t we jump right in to this week’s interview on Executive Evolution with Will Milano. so I’ve been, uh, with Integrity Solutions for just over seven years, uh, as Cmmo Integrity Solutions is a c. Sales training and development firm. We’ve been around for over 50 years actually. but we help mid to large size companies with sales organizations and sales leadership teams, as well as customer service teams, call centers, things like that, to develop both the, the skillset and the mindset of becoming great customer-centric sales and service organiz.

Fantastic. Well, are you ready?We always open up with the lightning round. Are you ready to jump in today?

[00:02:51] **Will Milano:** I think so.

[00:02:52] **Craig:** All right, let’s get started. What is the best leadership book you have ever read?

[00:02:59] **Will Milano:** So I thought about this and it’s, it’s fortunate and unfortunate, but it’s a book called The Score Takes Care of Itself by Bill Walsh. He was a longtime head coach of the San Francisco 49ers. I only say unfortunate because, I grew up as a Los Angeles Rams fan, so I’m very anti San Francisco 49ers.

So I begrudgingly have to admit that that’s. Definitely the leadership book that I’ve read that has stuck the most with me and that I, I learned probably the most from

it’s like almost kind of a weird guilty pleasure. Your favorite book is your least favorite team.

[00:03:31] **Will Milano:** it is, but it, it, it really is excellent and you don’t have to be a football fan to take a lot from it, but it’s a really, really good sort of introspective, leadership philosophy book. I’m gonna have to add that to the pile cuz you can’t argue with his results.

No, absolutely.

[00:03:47] **Craig:** All right, question number two. Who is your leadership crush? And I hope it’s not Bill Walsh.

[00:03:52] **Will Milano:** No, it’s not. and actually I’m not gonna use his name, but I, I thought of it as, you know, it was like, oh, was it like Simon Sinek or somebody like that? But it’s actually the person I thought of as somebody I worked for years ago. It was a c e o, that I worked for many years ago that, I just had so much respect for.

And, he was actually the, the first person I worked for when I came into the corporate training and. Industry taking over as I say, it was the first time I was working without a net in that I was the one leading the marketing function versus being part of the marketing team. And he was just a very, very empowering leader.

One of the anecdotes I remember about him is that I was early on in that role. I’d been with the firm maybe two to three months, and I. A little bit hesitant to sort of make decisions or be as vocal as I probably should have about what I was seeing and what I wanted to do. And I remember him coming to me, or maybe it was just in, in part of a one-on-one, but he said to me very subtly, but clearly he looked at me and he said, look, I want you to know that whatever you think we should be doing, I’m gonna back.

I’m gonna be behind you, And it was just, it was a very, I forget how he exactly worded, but it was just a very motivating and confidence building interaction that I had. And it just, it’s always stuck with me.

[00:05:16] **Craig:** Oh yeah. That’s incredibly empowering, especially for a newer leader.

I was just talking to a client earlier saying, you know how to motivate their team and it’s not the big la, I mean, the big lavish stuff is great, right? The awards. But those little moments where those words of encouragement or recognition are so incredibly powerful as a leader, and they shouldn’t be underestimated.

the other anecdote I thought of him, that always stuck out to me too, and it was around the idea of caring about people as as people. And about a year and a half year, year and a half later, my mother had gotten suddenly very, very ill. And I flew down to Florida and I was there and it was, it was a bad situation.

[00:05:57] **Will Milano:** I was going to an I C u four times a day every day for a couple of weeks. And I was also, when I wasn’t dealing with that, stressed about work, and trying to stay in communication with work and keep caught up on things. And again, he very subtly and succinctly said to me, I, I don’t know if it was by email or by phone.

He just said to me, we’ll, see when we. That was a huge thing to me that just very, again, very clearly, but simply communicated first things first and we’re here and you’re supported. it was an important moment to me that I’ve always, that’s always stayed with me.

[00:06:38] **Craig:** Oh yeah. Yeah. That’s amazing. the power we have as leaders of things that aren’t even. Moving a company forward, but just building that culture with people. That’s amazing.

All right, well, so now this will be an interesting, on the heels of that discussion. In 10 words or less, how would you define leadership?

I define it as one, empowering others. Leadership is about empowering others, and it’s about maintaining focus on the horizon.

So giving people the ability to get things done so you as the leader can be looking out a year, 18 months into the future to prepare for what’s coming.

[00:07:15] **Will Milano:** Yeah, I think your, I think one of your primary jobs as a leader is, again, as I said, em, empower others, which is giving them not only the skills, but the, the confidence and the runway to get out of their comfort zones. To let them feel like they can make decisions on their own, and which I think in turn, also adds to their, their confidence and their motivation.

And, um, that idea of maintaining focus on the horizon lets your people focus on the day-to-day, week to week, while your job as a leader has to be focused on where are we going as an organization, 6, 12, 24 months from. I think that’s what your people want from you. They wanna know that you believe that they can do the work day to day, while also having confidence that they know where you’re taking them longer term.

I had a friend who talked about helicopter leadership. That leader that just kind of floats around you, watching you every day. , we don’t want that. We want our teams to be empowered so they can do the job. Because you’ve got to be thinking about what’s coming down the road from what’s going on with your customers and the economy and all these things.

[00:08:24] **Craig:** And you, when you get people lifted up to the point where they can really take things on, that frees you to do that big work.

[00:08:31] **Will Milano:** Because I think your, that term helicopter leadership is good because I think what that, what does that communicate if you’re doing that, it communicates a lack of belief and confidence in your people. And what does that then do to their motivation?

[00:08:46] **Craig:** And I’d argue it’s probably not even leadership. it’s more managing, right? It’s more sitting on top of people and that, and some people think that’s leadership, but it is not

Well, so now that we’ve kind of talked about that incredible leadership mentor that you had, what was your first real leadership role that you, that you.

[00:09:03] **Will Milano:** So my, my first leadership role was actually in my, my first job outta college. So I went to, school in Southern California and my first job outta college was working for a rental car company in, their office in Beverly Hills, California. So I should have written a book about it because I had a lot of really, Interesting and strange interactions.

In the almost two years I was in that role, but four, four months into that role, I was promoted to branch manager. And so I was a 22 year old kid who had just been outta school for less than six months and all of a sudden, four months later, in charge of the office and, uh, it. It was an interesting experience, but something, you know, that you, it was a literal, um, trial by fire, drinking from the fire hose sort of experience.

But I learned a lot and I, I’ve of, I’ve often thought about that role years and years later, how much I actually learned from it about leadership, selling, customer service, finance, operations. It was my first exposure to marketing because you’re literally doing all of those things all day.

So what was that like being thrust in? I’m gonna guess you had employees that were a lot older than you, definitely customers probably that were a lot older than you, and suddenly you’re in charge. it was interesting because you’re right, it went from having peer relationships with other employees in the office to all of a sudden I was leading them and, leading and managing, which as we talked about sort of two overlapping but distinct things. And, one of the things when I think back.

[00:10:39] **Will Milano:** I received no training on what it meant to be a manager. It was just like, here’s your role now, go out there and you’re responsible. so it was certainly a lesson learned that anybody that’s put into a leadership role needs to have training and mentoring themselves to succeed. Just telling them to go out and lead, go out and coach.

They’re not prepared on their own. It’s, it’s actually a lot of what at Integrity Solutions we do with sales and service organizations is help those people that are thrust into those roles to actually understand what it means to lead and give them the skills, mindset, et cetera, to be successful. So it was, it was one of the things I learned in that role is, that I was unprepared for it, but, give yourself a little grace and.

it’s something you can, you can take away a lot from, I think your first leadership role.

[00:11:27] **Craig:** sure. And and it’s so interesting because a lot of times people get moved into leadership roles like. And we assume, well, big companies like the company you worked for, well they probably have leadership training programs, apparently have a lot of different things to make sure leaders are successful in the organization and small businesses, you know, or mid-size businesses, they don’t have those resources so they can’t do it.

But even in that big of a company with those kinds of resources, it was, here you go. This is your job description. Now

[00:11:54] **Will Milano:** right. It was, you know, you were good in your individual contributor role, now you’re gonna develop other, and part of what you’re, you know, again, in hindsight, this is, uh, almost 30 years ago, but, part of what I was charged with doing was developing other people and helping them. Become, you know, we talk about leadership and coaching is a lot about developing independent problem solvers, right?

And so I, it was something I think I wasn’t conscious of that I was doing, but subconsciously that I was, I knew I had to get people that could do things on their own because I was gonna be stretched 75 different ways as it was. And, um, so anything that you can do to help people understand what’s gonna come at them and how to deal with it on their own without coming to you for all the answers. leadership is about, again, not giving people answers, but empowering them to come up with answers on their own and giving them the runway to make mistakes along the way, which I think is something a lot of leaders are, have a hard time doing, is actually giving people that that runway or that that leeway to make mistakes and get it wrong.

[00:13:01] **Craig:** Yeah, it sounds like you had a real intuitive sense of that at 22, to know that that’s what we needed. That I needed to do. Did you have, what input from whoever, was it a regional manager or something you must have had, did you have a lot of guidance? Maybe not formal training, but did he give you any guidance?

[00:13:16] **Will Milano:** Yeah, I mean there was a regional manager. I don’t, I, I, I can’t recall exactly what sort of, um, I didn’t get a lot of mentoring myself.

But he, you know, he was sort of a, a calming influence and sort of did what he could to instill confidence in this young 22 year old kid that didn’t know anything about anything, you know?

[00:13:36] **Will Milano:** but again, it was, it, it was a very interesting time to be in Southern California and, it was around the time of. Earthquakes and OJ Simpson and all of that.a lot of stuff. And I, I met some celebrities along the way that, that walked into the office and it was just, it was again, one of those experiences that in a lot of ways I, I learned a ton from, again, in all those different,


Again, sales, marketing, operations, et cetera. And, it’s one of those things where in the moment you don’t realize how much you’re actually.

[00:14:05] **Craig:** Oh yeah. So it sounds like there was so much learning opportunity there and maybe some autograph opportunities, but did you, uh, what’s, if you think back, what’s the biggest leadership lesson you took away from that very first role?

[00:14:18] **Will Milano:** I think it’s to give yourself grace that and when you’re in your first leadership, You’re in very much uncharted waters and that it takes a lot of time to understand that. Again, if regardless of what function, you know, if you’re sales, marketing, finance, operations, whatever you might be, that when you get into a leadership role, your job has fundamentally changed.

And it’s not about the tactical doer mode sort of stuff. It’s that your primary job is developing other people around. And also making sure that the customers that you have are being served properly through those people. and so it, it’s a fundamentally different skillset and you’ve gotta be ready and willing to embrace that.

[00:15:04] **Craig:** Yeah, and that’s such a key piece for that transition and that first area of any responsibility for people Everything that got was successful for you to that point may not work anymore. You now have to get those things done through other people and may help them be successful,

and it’s such a mental pivot when you have to make that.

[00:15:25] **Will Milano:** it is, and I think the, the mental pivot is the most important part. There’s certainly anybody that gets into a leadership role, they need leadership and development training. And coaching, but it’s the mindset shift that’s the most important. If they haven’t changed their view of what their role is and what, they’re charged with, going forward, I, I think they’re gonna have a really, really hard time being successful because they’re going to have that, they’re going to revert back to what they know.

And that’s what we usually do when we’re under stress. We go back to what used to work. So suddenly we just start taking over the work ourselves, which hurts us. It hurts the team, and things don’t ultimately get done. So managing to that stress is such an important, changing the way we respond to it, like you said, it’s, it’s the mindset pivot.

[00:16:10] **Craig:** So, all right, what can I do to get these people moving in the right direction? that’s not my positional a. , you must do this. It’s, I need to motivate them and show them why it works

[00:16:20] **Will Milano:** and I, I think the other thing that, that I remember just historically through my career is that understanding that leadership is, is about strategy. It’s much less about the tactics, it’s about strategy, and that strategy in turn is about making choices.

So now we’ve got all these great lessons you’ve picked up. Let’s talk about today. So you’re, you’re, you’re in a leadership role today. What does that encompass? You know, What are some of the things that you’re managing to or leading to?

[00:16:49] **Will Milano:** so a, as a marketing leader, I think the marketing function is unique in, in. One of the things I’ve always loved about it is that marketing requires you to have one foot in the here and now. The this week, this month, maybe this quarter, sort of what’s going on, and one foot equally on where are we going as an organization and as a brand, 12, 18, 24 months from now.

And it requires a discipline to spend the appropriate amount of time in. As well as to communicate to the rest of the firm why you’re doing both because developing your brand, and again, as, CMO for a professional services organization like this, it’s about building our brand. It’s about client acquisition.

Client retention. So maintaining and expanding existing client relationships and then providing what I call, sales enablement tools to our sales team. So those are sort of the four fundamental aspects of what I think, being a CMO in a professional services or consulting type firm. Entails. but again, you, you’ve gotta have, um, be able to balance the, what’s important right now in the short term with where are you going as a company, because marketing really is that sort of tip of a spear.

As far as getting your brand out there, establishing trust, credibility with clients, exposure and brand awareness, all of those things that just, you don’t flip a switch to have those things happen. So you’ve gotta have the discipline to understand that slow and steady wins the race. And, part of that is being able to clearly and articulately, communicate internally what you’re doing and why.

and what are the unique challenges? Especially when I think about a marketing area, right? Where outside forces can drive what’s urgent and important.

[00:18:43] **Craig:** And the other side is you have to have this long term, steady view of things. How do you manage that? You understand that intrinsically, because you have experience, but you probably have team members who don’t have that experience.

How, as a leader, do you effectively communicate people that idea of slow and steady and calm when everything’s really agitated in the external environment?

I like to talk about how a lot of the things that you work. The sum of those things are greater than its parts. And I think that’s especially true in, in marketing and brand building. you’ve got to be results focused. So you’ve gotta be able to communicate, wins, progress, that sort of thing.

[00:19:24] **Will Milano:** And because you’ve gotta be results focused for the organization and that. Differently, depending on where you are, you know, operations, finance, sales, marketing, but it’s all about supporting the growth of the organization. So if you’re doing things that people can clearly see are making progress towards those goals, and you can sort of help tell the story of how all of these different things that you’re working on, weave. And build upon each other What you can’t do is get into reactive mode where you’re defending your own existence.

You’ve gotta be proactive and engaging to help people understand what the story is and not let the story be told for you.

[00:20:08] **Craig:** Yeah. And that that’s an important piece of dri where you can proactively drive your destiny as a leader, where you can kind of, you know, as we talked, looking into the future, really staying focused on that, even when it’s choppy in the here and now. So that proactive leadership is such an important piece of successful leadership.

[00:20:26] **Will Milano:** because I think whether you’re a, cmo, cso, you know, chief sales officer, coo, o o, Again, going back to what I said before about leadership is about strategy, and strategy is about choices. So you can’t be reactive and skipping from one bright, shiny object to the next. You’ve gotta be flexible and adaptable to some of the things that happened that are opportunistic that maybe you didn’t see or had planned for three or six months earlier, but at the same time, Maintaining that this is the direction that we’re going and these are the choices that we’re gonna make.

And letting people know that it means that you can’t do everything. you’re gonna make, prioritization, and decision making first and foremost. In, in, in your role.

I think you’re a hundred percent right. It’s, it’s communicating that and keeping people calm and keeping people steady, and keep keeping them focused and where you can really drive that vision. Is such an important piece. you sit in the C-suite for your organization. Obviously the c e o is setting kind of a long-term vision, but in that role, what is your role in kind of translating and supporting that vision from the c e O and the C-suite, both for your, your role and your team’s role.

[00:21:40] **Will Milano:** Well, I always talk about, marketing strategy is an offshoot of business strategy. So organizationally, the organization has to set a direction for here’s where we want to go as a company and here’s what our growth strategy is, and then the job of sales, marketing operations is to translate that into, and here’s how we are going to support that.

and provide the strong base for achieving that. , it, it can’t be the opposite. marketing strategy does not dictate business strategy. It’s gotta be the other way around. and part of the role of, I think a, a C-level executive is that idea of, working in the business versus on the.

[00:22:23] **Will Milano:** and and spending time in each, it’s again, just like we talked about earlier of, um, part of marketing is spending time on the here and now versus where you’re going 12 to 24 months from now. As a C level leader, how much of your time are you spending in the weeds versus working on the business of this is where we’re going as an organization, and if you again, say that you don’t have time to work on the business enough.

Are you leading and, developing the people on your team enough and empowering them to do the work so that you don’t have to be in those weeds? And that’s such an important piece of that mindset pivot is right, I’ve gotta be working on the business now, not in it. And that’s, that is kind of in how do I make that mindset shift. the other thing I think is interesting is how you said that, marketing doesn’t drive the business.

[00:23:12] **Craig:** So having that kind of vertical integration with the vision of the c e o. And then is there also kind of a horizontal integration when you’re a C-Suite leader to make sure that you are aligned with what’s going on with sales and ops and finance it? Where’s that balance point for you as.

[00:23:29] **Will Milano:** Yeah, I mean you, you’ve gotta have those relationships cross-functionally to understand what. What they need from you and what they’re hoping to receive from you, as well as what you need from them. It’s a reciprocal relationship, right? marketing can’t be a, sales says jump and marketing says how high.

That’s not a healthy relationship. It’s gotta be a partnership, and it’s why I’m, I’ve always been a firm believer. At least in, in the professional services side of the world, the idea of having a, singular function or person that leads sales and marketing, I think is a really, really dangerous thing because they certainly overlap and have to relate well to each other.

But the danger there that I’ve seen many times in companies is somebody that is the head of sales and marketing. Is that marketing becomes a gopher for the sales organization. And it’s a very, it becomes very reactive and it becomes very tactical versus strategic. but overall, I mean, I’ve gotta spend part of my time, making sure that I’m serving, and providing servant leadership to the sales organization as well as, again, communicating, Hey, this is what I need from you, what we need from you to help make sure that marketing’s doing what it has the potential to.

Well, and same with our head of operations, our head of product strategy, that sort of thing.

[00:24:52] **Craig:** Yeah. It’s so interesting, juxtaposing that first leadership role you had where you wore all the hats.

[00:24:58] **Will Milano:** Yeah.

[00:24:59] **Craig:** leadership role you have now where you hold, you have one hat, but have to work really hard to work with all the other people representing the other hats. So if you think about it, if you could jump into a time machine today, go back to that 22 year old working at the rental car place and give him one piece of advice that would help him the most, what would that piece of advice be?

[00:25:23] **Will Milano:** I think the main piece of advice would be to show others that you have confidence in them. Make it really clear that you believe in them, and spend enough, allocate enough time to really, connecting and hearing with. Hearing from people on your team and letting them know that you believe in them and will support them.

And I go back to what, you know, I said at the beginning of the podcast about the, the leader that I remember from years ago who said to me again, Hey, whatever you decide that we should be doing as an organization to create this strategic marketing function, I’m gonna back you. That carries a lot of power and I think not.

Of leaders do that for their people, they revert back to, there’s a sort of a Venn diagram, right, of leading, managing, and coaching. And they’re all very important and they’re all interconnected, but they’re also very distinct. And you’ve gotta spend enough time, I think, as a leader on all three of those aspects and understand where they overlap and where they don’t.

it’s such a big role and, and I love what you said about instilling confidence in others and, and how that would perhaps change and simplify your role as the leader when the people have the confidence to know they can act,

if you’re not expressing confidence in people on your team, why did you hire them?

if you’re having to do the work for them or dictate what they should be doing day-to-day, week to week, then chances are you hired the wrong person.

[00:26:53] **Craig:** Yeah. And boy, that’s a whole topic for another interview because that’s actually a really interesting leadership problem right there. But Will, this was fantastic. Thanks for sharing both your growth and your evolution as a leader for us today. If people want to know more about you or more about Integrity Solutions, what’s the best way for them to get connected?

[00:27:13] **Will Milano:** Sure. I’m personally on LinkedIn. That’s the only social media that I I’m part of. so people can find me on LinkedIn. I host our podcast, which is called Mental Selling. Um, that podcast is. Sort of as it connotates, it gets down to the critical mental and emotional and attitudinal aspects of selling and sales leadership.

[00:27:36] **Craig:** So I, I would invite anybody that’s in a sales or sales leadership role or knows people that are to, find us, wherever you get your podcast and subscribe to that and our. Company That was a great interview with Will. He brought several important points to the table on how we develop leaders and how we grow. I think one of the favorite pull quotes for me from his interview today is that leadership is about strategy, not tactics.

So I’d encourage you to jump over to Will’s podcast and take a listen over at the Mental Selling Podcast to hear more from him and we’ll drop links to that and his LinkedIn profile in the show notes. But I always like to leave you with three takeaways within the context of the three important leadership characteristics of confidence, confidence, and calm.

What I heard from Will around confidence is how that mentor early on in one of his early leadership roles, helped him to really get the direction in the confidence in himself by telling him, Hey, I have got your back on these things. Not only his decision making, but also any. Had to go through a tough time with his family and helped him gain perspective.

So that confidence is so important and we as senior leaders can provide that for our new leaders in the area of confidence. He talked about the importance in leadership of making the mindset pivot. To working on not in the business. When you’re working on the business, that builds your confidence cuz now you’re looking at the long-term picture for your business as opposed to just rolling your sleeves up every day and being so lost in the detail that you don’t know where your business is going and when you’re setting that long-term direction.

That is both makes you more confident, but it also instills confidence in your team. And then the final point around calm again, I want to go back to that leader when he was going through that mentor of his as Will was going through that struggling time with his mother and he knew he was gonna miss a lot of time at work.

That leader helped him to see the priorities. He helped him to know that things would be taken care of until he was able to come back into the office, and that allowed will to focus on his family at a time when that was the most important thing in his life. Thinking about how we can do that as leaders for our teams is such an important piece and building that calm both within ourselves, within our leaders, and within our teams.

If you would like to see more content from me, I would encourage you to follow me over on LinkedIn. You can find me at Craig p Anderson on LinkedIn and lots of content going out through the week. Introduce yourself, send a connection request, and let’s benefit from knowing each other better on that platform.

Thanks, everybody. Join us next time on the Executive Evolution Podcast.