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Building Confidence in the High Stakes Game of Sales Leadership

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Confidence is a tricky thing. It’s hard to gain, and easy to lose. This week we take ideas and insights from J. Ryan Williams, an experienced and certified executive coach and individual who has done the Zero to $100 million dollar journey three times. He speaks with us about building confidence in the high stakes game of sales leadership.

What you'll learn:

  • How to build confidence in a high-stakes world.
  • What is the zero to 100 million dollar journey.
  • How to deal with imposter syndrome.
  • How does a sales leader impart confidence into their sellers.
  • What are some common stakeholder motivations.
  • The importance of responding instead of reacting.


Free offer for listeners of the Full Funnel Freedom Podcast.

It's incredibly frustrating as sales leaders when our sellers get a deal almost across the finish line, but can't quite push it to the finish, even though they've promised us that it's coming in real soon.

We are offering a Free white paper on Three ways to get those sales across the line.

To get this free, insightful report, visit us at



Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist - by Brad Feld and Jason Mendelson

The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to Go from $0 to $100 Million. - by Mark Roberge

The Effective Executive: The Definitive Guide to Getting the Right Things Done - by Peter F. Drucker

Designing Your Work Life: How to Thrive and Change and Find Happiness at Work - by Bill Burnett and Dave Evans

MasterClass - Learn from the Best, Be Your Best

  1. Ryan Williams' YouTube Channel

The Power of Feeling Safe

[0:00] So once that safety exists, and I know that I'm in a safe place, then I could do a lot with that.

Introduction to Full Funnel Freedom Podcast

[0:12] Welcome to the Full Funnel Freedom podcast. If you are listening to this, you are likely leading a team, responsible for generating revenue.
Purpose of Full Funnel Freedom is to support people like yourself and keep your funnels consistently reliably full.
Welcome to the Full Funnel Freedom Podcast. I'm your host Hamish Knox. Today I am delighted to have Ryan Williams, certified executive coach and individual who has done the zero to a hundred million dollar journey three times to talk about building confidence in the high stakes world of sales leadership. Free offer for listeners of the Full Funnel Freedom Podcast. I've got a report called three ways to ensure your sales cycle doesn't sputter in the last mile.
You can get that at slash sputter.
It's incredibly frustrating as sales leaders when our sellers get a deal almost across the finish line, but can't quite push it to the finish, even though they've promised us that it's coming in real soon.
So go get your free report, three ways to ensure your sales cycle does not sputter in the last mile at forward slash sputter.
Now back to the show.

[1:34] Thanks so much for having me. You're very welcome. So Ryan, I've given the audience the 30,000 foot view of who you are and what you do.
Take us down a level, tell us where you came from. I told the audience he did the zero to 100 million three times, so there's gotta be some good stories there. And then tell us what you're doing today and who you're supporting.
Yeah, sure. Well, I mean, that's a great intro. The very short and sweet is I spent the last seven years working as executive coach to founders, leaders, and teams, primarily in tech and SaaS companies.
But the thing that comes up over and over and over again is really around human potential.
It's, we know our founders are onto something interesting when they get funded by their VC, but there's a big journey from interesting idea to things someone will buy, to process that someone will buy again and find that.
And then we end up with a people problem, hiring the people, scaling the team.
And so what happened for me personally is I started my career in human development and education and social work.
I got a master's degree in social work at University of Chicago.
And my friends about the same time as graduation said, why don't you come to the San Francisco Bay Area, and get involved in technology? You've always liked computers.
You've always liked teaching people. Teach someone how the computer works and then ask them to buy it.

[3:00] And more specifically asked them to buy software. And so this is the very beginning of the SaaS revolution, you know, a handful of years ago. And then shortly after I spent 12 years in sales leadership.

Building a $58 million sales team at AdRoll

[3:10] And so I built a $58 million sales team at a company called AdRoll.
That was a 22-month journey I'll never forget.
On both sides of that experience was working with some people that I consider very, very dear friends, but I got to see what it looks like to go from, well, I guess we were doing about $4,000 a month in ARR.
And, uh, or an MRR and I left there, we were doing $750,000 a day USD.
And so, um, you know, roughly call it zero to almost 300 million.
And then I, during that experience, I started advising other companies that were looking for the same, same journey.
I worked with the founder of envision app, which is a tool similar to what most people have heard of Figma today.
But I was with envision as we grew from 10 employees to 2000 and did zero to a hundred million dollar journey there. They were one of the fastest growing software companies of their day and are still doing some great work today. And it was right after that, that I realized, hey, actually sales leadership is interesting. I became a VP of sales at a YC backed data company. And I love that job for a lot of things. And I also didn't like that job.
The part I loved was, it will be no surprise to you, is where my career started to come back together. Developing people, helping managers become directors and directors become VPs.

[4:36] What I loved was helping founders figure out their sales model. The same thing I'd been doing, as an advisor earlier in my career. And so with those two things happening, at the same time.

[4:47] The normal VP of sales stuff. So some politics, some boards, some investor management, things like that that I didn't necessarily love as much. I said, okay, how do I do the VP of sales stuff but only the things that I like?
And so I left to become an advisor, consultant, and later an executive coach because there, and this is where I am today, focusing on how high potential leaders can actually.

[5:13] Find and embrace the best parts of their day and their career and their life. And so, so yeah, so that's where I am. So I spend most of my time working with founders who are venture backed and they are making a bet on their doing sales themselves usually, or they're hiring their first couple of sales reps. Usually they're doing it themselves, kind of DIYing sales, but really, from the perspective of how do they find the pattern so they can hire the right people. You know, we don't want them to go hire our friends and then fire them right away. And so, yeah, so that's how I spend my time. And so I got to see the $0 million journey as an operator, as an advisor, and then later as an executive coach with a company that was one of the fastest growing technologies in the transportation sector. And I just have been having a blast doing it.

The importance of confidence in sales and leadership

[6:03] And yeah, so that's me in a nutshell. Amazing. What an incredible journey. And, obviously you've seen lots of things and now you're back, like you said, not at the beginning, doing what you love doing in developing people. And you made a very present comment just a second know about founders who have a thing, they launch the thing and then they decide, well, I got to hire a sales VP. So they go find one of our friends and then three, six, nine, maybe 12 months later, our friend calls us up and goes, hey, I'm back on the street again.
So when we talk about confidence, let's start with the founder because the founder has to have a lot of confidence to even like take the leap in entrepreneurship. What have you seen from your work with founders around confidence as it relates to sales and then bringing on a sales leader?
Yeah. Well, a lot of people think that the thing they notice about a salesperson right away is.

[7:05] Bravado. They see somebody and they think, oh, this person must be selling me something. They're cocky. They don't separate confidence in the way that I think about it. I think about confidence in the product. I think about confidence in yourself, which is how well do you know what you're doing, which is really presence.
If you think about it, it's not, do I know what I'm doing right now, but do I know that I'm doing it?
Right, it's kind of like when we go to the fridge, open it up and look for food and forget what we're there for, right? Do I know why I'm here?
Do I know what I'm doing?
And then the third piece, when I think about confidence is not in the thing that I'm selling or the how that I'm selling it, but also confident in terms of where this conversation taking place, where in the industry, where for the prospect and where for us personally.
If this is the deal that I need to pay rent, I'm not often operating from the, this is a no-brainer, it's going to happen. I'm operating from a place of fear. I'm operating out of a scarcity mindset. This has to happen. And our sales leaders often put pressure on that. It's the last day of the month. What have you done for me lately? Get this done, get this done, get this done. I work with a lot of founders who sing that tune to their sellers.

Pressure in sales and the impact on mindset and performance

[8:24] Ouch. Hey, is this thing going to happen? I'm not trying to put any pressure. I just want to know because the board meeting is tomorrow. And that's not their fault either, right? Because they will get the question. So they're rolling that question downhill. And that doesn't necessarily help our people be in a place of presence, be in an abundant mindset of this is going to have the right fit. And really, if you've done the chores of identifying the right customer, prospecting them appropriately, setting the conversation, setting the table, explaining what the reason for your call is, whether that be an enterprise motion where, we're going to do something that is going to be 17 steps or an SAB motion where I may be selling in the same call of my same cold call. Do I know why I'm there and what I'm doing?
And does that actually fit for the other person? One of the things I love about.

[9:24] Some of the methodologies out there is that when you think about it from a standpoint, whether you call it a choreography, like some of our friends do, or you call it a methodology, or you call it a sales process, it all means I know what I'm doing. And if I know what I'm doing, Now we start to talk again about that confidence.
I know I'm here, I know what I'm doing. And so oftentimes if you can envision yourself in a place where you have some of those elements, where you have presence, where you have a belonging, you know why you're there, you know that you fit.
You know, a lot of people have trouble with networking because they start with that, do I belong here?
They start with that imposter syndrome. Instead, go, okay, start with a, what's a time that you felt like you belonged?
What's the time that you felt like you had influence? When have you been competent?

Finding the Missing Pieces in a Sales Conversation

[10:17] And, and can you take that, that memory and say, okay, what is missing about this sales conversation?
How do I get back to that same place? It might be who I'm selling to where I'm selling them, by the way, belonging, usefulness, influence and competence are the four pillars of the afterschool program at the boys and girls club where I started my career.
Love it. Right? So, so when we think about, okay, can a social worker do enterprise sales?
A lot of people didn't believe me that I could.

[10:47] And then once I started doing that, then it became, Oh yeah, of course, no brainer.
You know, of course those skills translate, but you know, tell that to me in 2010, when I was out hustling and trying to find that first startup job, people did take risks.
And I honestly, the, the fastest growing startup I've worked at, I'm quite certain I got the job because I could talk about Chicago pizza with the CFO who was hiring for the team, managing the team himself.
And he was from the North suburbs of Chicago. So he saw University of Chicago, my resume, he asked me how I liked my slice.
That was what our conversation is. And I got to tell you, I'd never admitted to him, I don't like pizza.
Like, but it's a very Chicago thing. But I can have a Chicago conversation, right?
I can even not like pizza, I can get to that zone of confidence and say, okay, I understand what we're trying to do here. And our goal there was building rapport.

[11:34] What's the goal with your meeting with your client? And how do you get back to that place where you feel that sense of belonging, feel useful and competent and can have influence over where it goes. That's how I think about it to answer that confidence question. So many amazing nuggets in what you just shared.
And it reminds me, I was doing a coaching call with a founder in the tech space recently, and they had been invited to a dinner with some very, very high level people, government people, very large companies. That's not intimidating at all for our founder.
Not at all. Not at all. And also they are – let's just say they don't look like the rest of the people around the table. Let's just put it that way. And so we were talking about how do you introduce themself and people are going around the table beating their chest about all the degrees they had and all these sorts of things. And I said, well, why do you feel like you have to do that? And they said, well, because of this and this and this. And I said, well, number one, differentiate on how you sell not what you sell. Also, you belong there because you're there.

[12:39] People who don't belong there don't get invited to those rooms. And so right away to reinforce what you were saying about, do you belong there and am I an imposter? If you're invited and if you're in that room, you belong in that room. So take what Ryan said about taking the pressure off of yourself and by extension off of your sellers and add that and go out and have those human to human conversations so you can sell without it sounding like a sales pitch.
And can we dig in there real quick, back to the imposter syndrome thing.

Overcoming Imposter Syndrome and Imparting Confidence in Sellers

[13:12] So imposter syndrome is a really fun, buzzy word that a lot of people throw around.
But an exercise that I like to do with sales leaders, which also works for founders, is to think about who does belong in that room.
Okay, so I'll run the sales leader example, and this is a true story.

[13:31] We've seen all the companies grow and take off and hit the headlines in the press with They fundraise and we go, Oh man, wouldn't it be cool to work at a place like X or Y?
Oftentimes leaders that work in those places, they never feel that I'm in the right place.
I'm here because I'm supposed to be because they're operating in different environment.
The environment they're operating in, the MBAs are getting hired.
People are coming in with impressive backgrounds. People are leaving Google to join their startup.
And they were there two years ago when nobody had heard of them.
So let's ask the question differently.
Okay, who has been in the environment that you're in?
What do you have? You've got a team of 20, they're doing a million dollars a piece.
Okay, so you're carrying a $20 million back, whatever that number is.
In the case of the example I'm giving you, it was probably about 16 mil.
Okay, how many other sales leaders have gone from zero to 16 million in less than 18 months?
Can you name anybody else? And this particular client said, no, I actually, I can't. But I would imagine they exist here, here, and here. He listed five companies. Okay, great. So of those five companies, how many people like you are there at those companies? Let's say it's two each.

[14:45] Okay, so you're telling me that you're one of 10. I hadn't thought about it that way. Okay, so let's assume you don't know the entire market. How much of the market don't you know?
Let's say I don't know half the market, but I pay attention to who's getting venture funding. I pay attention to what other companies are in our space and doing similar types of SaaS. Okay, so multiply that by two then if you only know half the market, what's the other half the market? Okay, so you're on a list of 20. Even on your lowest self-confidence day, you are one of 20. And so now I go, okay, who does belong here? It's probably somebody who has done X, done Y.
And that looks a whole lot like a unicorn to somebody. I talked to a coaching client recently who is in the process of finding a new job. And he was like, I don't feel qualified for much of the things that I'm talking to because there's a particular leadership gap in his experience. I said, I totally get that. That would make me self-conscious too.
Can you name somebody else who's worked in this particular industry with this particular experience and has also done this other thing that he had done? Because I can't think of anybody else.
Do you think they're out there? Maybe two or three others. Okay, so then you're a unicorn.

[16:02] I don't think you should walk into the interview and say, hi, I'm Joe, I'm a unicorn. I don't think you should do that. But when you think about belonging, think about who should be in that conversation. So I totally agree with you that just being invited is one level of acknowledging that you're meant to be there. Somebody else thinks you should be there because you got invited.
But there's also this layer of what are the experiences that you're bringing into that room, to make it a better place. Well, those experiences often indicate that you belong or you're meant to to be in that conversation too. And so imposter syndrome and executive presence is just one of kind of the five most common things that come up for sales leaders that I've worked with as a coach.

[16:52] Amen. That's a great story. Thank you for sharing that with us, Ryan. So it also reminds me that we were chatting off air about how, as humans, we think that we're the only ones who have ever gone through this experience. And with a quick exercise and audience, I'll encourage you to go back and re-listen to that exercise Ryan walked his clients through.
With a quick exercise in one case, your client discovered that they were one of at least 20 people. So there are 19 other people that they could potentially reach out to and go, hey, I'm struggling with something or I'd love to connect with you and commiserate and etc, etc.
So sales leaders, if you're feeling alone.

[17:36] You're not. There's someone out there who is like you and who is willing to support you.
So Ryan, we've got the founder, we've got the executive presence, we've got the sales leader, this exercise you just gave us, you belong in the room. So how then does a sales leader, impart confidence into their sellers? They can't just magic it out of their mouth or rub sweat on them or anything like that. Some of that stuff is not okay by HR anyways. So how does a sales leader.

Building Confidence in Your Sales Team

[18:11] Build a sales team that also has that level of confidence that you've been describing?
Well, I think one of the number one things you can do to build confidence for your sales team, whether you're a founder thinking about your first group of AEs or you're a sales leader, hiring a group of AEs, or you are a first-time manager where you've just taken over the team.
All three of those types are people who will need to build confidence in their team.
One thing that we know when we think about making people confident or creating an air of confidence is that people have to be comfortable, they have to be safe.
And so what is safety when we think about it? You can look up the term psychological safety, there's some great definitions there, but But really it's, do I feel like I could be vulnerable and not get laughed at?
I think about safety and I think if I say what I'm thinking I'm saying, right?
What I'm thinking about saying, will you laugh at me?
Will your audience reject my idea? Do I feel safe where I could say something and that be an unpopular opinion?

[19:20] Without it coming back without me being questioned without being torn apart without you, Not posting this episode or whatever. It is that lives in my fear is am I willing to face that fear?
Whether that's through a conversation through a pitch. So once that safety exists, And I know That i'm in a safe place Then I could do a lot with that, So a founder who's saying hey, I need to get this deal done before the board meeting That saying that may not create that safety.
The sales rep might already know that, right?
But saying, hey, look, we all know the stakes.
Here's what it is for me personally. What is it for you?
Maybe there's a different set of stakes for that sales rep.
Maybe this is a make or break deal. I went to a girlfriend who I was living with and I said, I can't pay rent because the sales job's not going great.
I know what that level of low looks like too. Wow, right? And do you feel safe enough to say that at work?
Hey, this is why I need this to happen. This is a big opportunity for me.

[20:24] When that safety exists, then we can start to go, okay, no matter what happens, someone's got my back.
Someone's gonna keep me from getting laughed at, being humiliated, or feeling like I put myself out there for no return. All right, so that's our table stakes as leaders.

Going Beyond Safety: Helping Sales Reps Build Confidence

[20:42] To make our team feel safe, then we can, if that's table stakes, then we can start doing some other things on top of that.
Right? We can help people take an inventory of times that they have been confident.
Times that they have been right times that they've been able to say, Hey, I've got it.
So some people are in the frame of mind where they have to say, I need to have 10 experiences.
They don't usually have that number, but let's say it's 10. I need to do this 10 pitch 10 times and I've got it cold.
Right. That's true for some people. Other people need to screw up quietly.
They're the ones who go in the call booths and they do a couple of pitches before they're comfortable doing calls on the floor.

[21:21] Okay. Others may ask you for something else. But if you've created that safety then your seller can ask you for what they need. There was a rep on my team named Brittany years ago who was one of, was a great person to work with. She was a lot of fun but also knew what she needed when she was training. So she came to me in her like second or third week work and she said, hey at 10 a.m. tomorrow I have the sales pitch and I'd like you to join me. So I joined and I asked the question that I think all of your listeners should learn to ask if they're not already. When I joined that call before we dialed in, I said, Brit, what is my role on this call? And she said, the role I want you to play is to be here and do pricing. So if it gets to the place, they say, how much does this cost? I'm not confident in my explanation of pricing yet. I need you to handle that.
Okay. So in order for me to do that in a way that's appropriate for the client, I got to participate on the front end of the call too. So they know we're both on the phone, so I don't come out of nowhere. Okay. So we build rapport. We all know we're there.
She does the product pitch. Here's what our product does. Then we come to the pricing.
I take over the pricing question, and then we wrap up the call with what the next steps are.
And don't worry, there were next steps. There's always next steps. If I'm showing up on a sales call, we're talking about next steps. And she did a great job of getting next steps. She had had six or seven years of sales experience by the time we were doing this together.

[22:44] The very next day, she said, said hey.
I saw that you're free at 10 a.m. Will you join another sales call with me? I know I'm asking a lot. It's two days in a row. 10 a.m. is free. Will you join this call?" She had booked a call with a, customer who was almost exactly the same as the customer we saw the day before.
This is why I remember the story so clear. One was like The other was like It was something like that. It was very, very similar. And Brittany had set up this call. We go there. I said, what's my role? And she goes, your role is to listen to me, give pricing and then give me feedback. She had put me in the feedback chair. I can't remember if I was in a silent listen to the whole call or if I was introduced, but she knew what she needed from me and then she got it. And then she went and aced the pricing conversation. And for me, being able to tell her she aced it, that's what she needed. She needed to have someone else.

[23:35] Certify that she had the pricing answer down in a way that was on standard with what other successful reps were doing. We accomplished that in two one-hour sessions that happened to be back to back, which is again why it's so memorable. But Brittany went and asked for what she needed.

[23:53] She got what she needed from her manager. This isn't a story about me being so great. It's a story about a rep knowing what you needed and asking for it. But that safety has to exist for our people to be able to do that. And so that's what I would encourage people to do, whether you're a founder, a leader on the team, or a trainer or a peer mentor. How do you create a safe enough place so that people around you can ask what they need to, ask for the support they need, but also feel like they've got a backstop where someone's going to have their back if something goes awry. That is an incredible story. Thank you very much for sharing that with us and totally resonates. Until our people feel safe, they are not going to tell us what's really going on. They're not going to tell us what they need. Now let's flip it in the other direction because you've been chatting a lot on LinkedIn recently as we're recording this about the sales leader to the board and you've shared some fears that you had as a sales leader, questions you weren't going to – weren't comfortable asking that you've now subsequently asked and got information. So would you be comfortable sharing a little bit about what are those questions and what are some of the answers you've heard that maybe you would have appreciated knowing when you were in a sales leader role. Yeah, so I think the number one thing is understanding everybody's motivation.

[25:11] Your customer has a motivation and why they're buying from you. Your boss has a motivation on why they built the team that you're on. That's true at any level at any company, right?
Everybody has a motivation. Our investors have motivation too.

[25:26] And so anybody who hasn't done a deep dive into the stakeholders of their company.
Now, I'm not talking about going to the founder and saying, who's our stakeholders?
That's not going to be a really positive conversation. But there's a lot of stuff you can look up. And then the conversation is, hey, I was looking at our stakeholders, and I saw that so-and-so had invested. Are they still involved? What do they want?
If you ask that conversation for that conversation in an elevator, it's not going to go anywhere.
But if you ask that at a time when it's appropriate, and it's part of your professional development to know and understand that. Great. There's a book that a lot of people who work in tech should read and they haven't read, which is a book that basically lays out.

Understanding VC Economics: Two and 20 Fund

[26:07] Why VCs do what they do. It's called Venture Deals by Brad Feld. And in Venture Deals, he lays out the economics of a venture fund. I shouldn't say he, Brad has a co-author, but They lay out their, here's how fund works. And so if you don't know how your investors are getting paid, which is mostly what they call a two and 20 fund, then you don't know what their incentives are. You don't know what they need the company to do. Two and 20 means if they raise a hundred million dollar fund, they take $2 million for a management fee. That's how they pay for their office, their private jets, their ball pits, whatever they've got at the VC and the parties that they've invited you to. But then they get 20% of the upside in all these investments.
Which means they need you to increase the value of their investment.
How do we do that as salespeople? We do that through revenue.

[26:56] And so oftentimes that investor is looking for benchmark data that shows the investment is going the right direction.
They're also, if they're doing their job, they've got a fiduciary responsibility to other stakeholders, if they've got the board seat, which is you too, right?
If you own stock in your company, like they're, they're there to support you.
And ask hard questions about what's going wrong.
Not only what's going right, how do we mark up, what's going wrong, is this potential markdown?
Are we losing value here for something?

[27:28] As a VP of sales, I had had a really rough board meeting at a series B stage company.
We had presented the sales plan and the next person to go in the meeting was marketing.
Marketing presented the marketing plan and in the marketing plan, that leader who, I don't falter for this. I did at the time said we have a thousand leads.
I'm making up a number for this case, but a thousand leads and we have 500 good leads.

[27:53] That are helping us move forward, that are entering the process.
So the board made the same face you just did and said, okay, what about those other 500?
She goes, oh, those are in the toilet because the VP of sales doesn't want to work on those.
They weren't aligned with what we would call sales qualified lead.
It wasn't ICP lead, it was an ideal customer that we wanted to go after, that I felt like fit the strategy that we had laid out.
The board said, are we going to be losing value by not having a product that leads with these qualities, these SMB leads would want.
Why are we only going after enterprise? Ultimately we ended up kind of building more products than we had the team to build, which ended up being a bit of a dilemma.

VCs as Potential Allies: Asking for Help and Advice

[28:35] But the lesson I learned was, here's this board person whose job it is to ask the question, are we at risk of losing value or is there opportunity to gain more value?
It's easy to call that a vulture capitalist because they're trying to gain value.
But the truth is their job is to protect their limited partners and increase the value of their investments the best they can, which also means they're a great person to go ask for help.

[29:03] If it's appropriate, you have the support of your founder and the rest of the board.
Asking that VC for help is also not a bad thing.
When I interviewed five VCs for a project that I did recently that covers about $10 billion worth of funds and sitting down and saying, Hey, what do you want from your VPs of sales?
They all said, we want VPs of sales that will come and ask us for help because I may not have the answer, but I know somebody who does.
I know another VP of sales who was at this stage. Investors want us to ask for that as leaders, but we often feel intimidated.
Like we have to show that we have all the answers.
Wow. And that goes – circles back to imposter syndrome, which we were talking about earlier.
Ryan, I could visit with you all day about this stuff. You and I have very similar passions.
I am curious if you could go back to younger Ryan, however far back you want to go and say, hey, younger Ryan, fast forward, you're going to be a certified executive coach. You'll have gone the zero to 100 million journey three times. You're also going to have a bunch of bumps and bruises and a bunch of scar tissue. What would you coach younger self to say or do differently to arrive at the same place, but with a little less scar tissue and fewer bumps and bruises?
I think if I could go back and give myself some advice, one of the things that I would do is.

Embracing the Long Game and Creating Long-Term Value

[30:20] Really preach the long game. There's a way to approach your career and every sale as, how do I create a long-term relationship? How do I create long-term value? I think I have done a a good job at that. But it feels like there are places where it would have been easier to recognize, hey, this is a small blip. This is a short story in a longer book. And I think that as a leader, our responsibility is to have that perspective. But as founders, that perspective is important too. This is just one blip at a time. This is a thing that we're trying to learn from.
It's not counter thesis when we do something that's that's different or an experiment.
It's let's do let's find out and then let's make decisions based on what we know, rather than what we think. You know my wife has been talking to my kids. My kids are 10 and 11 right now. She's been talking to them about this concept of responding and not reacting. It's very easy when you're a young kid to react. Some punches in the shoulder you're going to react to that and lash out as opposed to respond and say, what's going on?
Right, they just got hit in the shoulder. Maybe you weren't punched.
Maybe somebody bumped into you because they lost their balance.
It's a chance to catch a friend.

[31:37] If you're responding, you're going to see that. If you're reacting, you're not going to see that.
So I think that'd be another place where I tell myself, hey, this may be a time to sit, look at the whole picture and respond rather than react.
The example I gave you a minute ago about marketing and qualified leads and what sales thought was qualified versus marketing, I reacted to a really negative situation.
And that hurt my cross-functional relationships. It set a bad role model for the team.
And it also didn't look good to the rest of the people that I wanted to look good around.
If nothing else, wanting to look good and wanting to feel like you're in place is something that I think all of us think about. But if I had looked at a bigger picture and responded instead of reacted, I think things would have gone a little differently for me there.

Resources for Personal and Professional Development

[32:24] Fair enough. Two incredible pieces of advice. Thank you for sharing those with us. Curious, what have you read, watched, listened to recently or in the past that you would encourage our audience of sales leaders to check out as well to further their own personal and professional development? Yeah. I'll give you a couple ones and then I'm going to give you a really selfish plug. Sure.
If I'm allowed to. Amen, brother.
So the first is they need to listen to Full Funnel podcast, Full Funnel Freedom. But in In all seriousness, there are a lot of resources that can help us get better, but we often will flock to the resources that have the most noise around them, as opposed to looking at our specific use case.
Sales Acceleration Formula by Mark Roberge, great book, check it out.
But you're also not building HubSpot and it's not 2010. So maybe think about, okay, what can I take here?
What can I not take here?
When I started my first VP of sales job, I read The Effective Executive by, I think that's Peter Drucker. And I got a lot out of it.

[33:29] But I also went in thinking, what can I take and what can I leave? A lot of the management examples is 1950s America, post-World War II, starting to think about where we were as an industrial economy at that point. That's not the executive. I'm not trying to be Don Draper, but there's some things in there that were really helpful to take the way to do an inventory on what's working, what's not working. So I would say, just think about resources that way.
And then there's a lot of resources that are more non-traditional that will help you assess where you're at.
And so that could be doing your personal work around confidence and belonging, if that's a place where you struggle.
If you struggle with knowing that you're the right place for where you want to be in your career, then there's a great resource from Stanford. Dave Evans and his partner Bill wrote a book called Design Your Life.
I think you could read that book, Design Your Life, and actually think about how you want to design your sales life in your career.
But it's written for how to choose your major as a freshman at Stanford.
But it's really helpful for me personally for thinking about, okay, what are my priorities?
What am I trying to do?

[34:43] I got a lot of value out of a membership. I mean, all salespeople have signed up when they heard Chris Voss was on there, and he's got a great piece.
But you go and you listen to the comedians talk about structuring jokes and talking about communication.
I think there's a lot of value there.
I got a lot of value watching documentary filmmakers talk about making movies.

[35:04] Does that help me as a seller? It absolutely does. When we think about our job as storytelling, our job as presence, our job is choosing the right setting for the conversation that needs to happen.
Like that is setting a scene.
Okay. So those are some resources that I would encourage people to think about.
There are a lot of things out there that you could be doing, um, but those things, you know, it's, it's kind of like the, the advice that trainers or coaches will give to athletes of the stretches and work doing, if you're not doing it for 10, you know, 10 seconds or whatever that, that advice is.
And there's a bunch of those in athletics. We need to have some of those in sales and career.
And listen to a podcast. It's not really worth it unless you're going to write notes from it and think, okay, here's what I'm going to do.
And that should make that decision. There is other content where it's actually really worth listening to as a wash over exercise.
Listening to content that you already know, let it go wash over.
And then, you know, we also talked about venture deals.
It surprises me how few sales leaders understand the venture economics of the investors who back their companies.
They don't know who the people are and they don't read the same things they read, which would really help when you're having a conversation at the board level on what you're doing, why you're doing it, if you're making the right size bet.

[36:26] Very cool. So we will put links to all the things you mentioned and strongly encourage the listeners as well to take notes. All the stuff works, but if you don't implement it, well, you're never going to know. So all of it works in theory until it's actually executed.
So take Ryan's words to heart, take some notes, actually go ahead and execute it. Ryan, I've loved our visit today. I look forward to continuing our chat offline. What's a closing bit of wisdom, a final thought, or something you want to plug before we wrap up?

[36:57] Well, I'll take the selfish plug moment and share that recently I've launched a YouTube channel.
And the first two pieces of content on there are a group of leaders talking behind the back of a VP of sales. I interviewed the CFO, a CMO, a head of customer success, and a CEO.

[37:15] About their thoughts on the VP of sales and sales leadership. I've heard a lot of feedback from founders that they appreciate that as much as sales leaders did. And then the second part of that, which is kind of warming this channel that I'm launching, is a video with the investors, which is what you had asked me about earlier, digging into what the investors are looking for.
But the thing about that video that was really fun for me is I deliberately chose investors at three different stages from seed, series A and B, to cloud investors. Marriott Bessemer, she does, deals with the cloud 100, the biggest companies in enterprise tech. She's investing in and evaluating those spaces. So to hear her say, here's what I expect as a board member, you got to take those words to heart. And if you're at the earlier stage, you probably want to listen to Charles from Precursor talk about, here's how he thinks about experiments and bets.
So anybody looking for that, you can search on YouTube for J. Ryan Williams, but still a small channel, you might not find me. So start it over on LinkedIn, you'll find me on LinkedIn, and there'll be a link in my profile to get to that content, which I would love to hear from people. And everybody says, like, subscribe, comment, all that stuff. For me, it's not the selfish smash that bell. It's, this is the community I want to keep the conversation with, because I think this is the community that's going to have the most value on content like that.

[38:37] And so I would encourage people who are curious about the stuff we talked about today, to go check out both of those videos. They're eight minutes and like 12 minutes respectively.
They're not long. They're kind of short digestible pieces of wisdom.

[38:51] Amazing. And we will absolutely put links to your LinkedIn profile and the YouTube channel in the show notes. So make it super easy for our listeners to find. I had a blast today.
Thank you so much for being a guest on Full Funnel Freedom today.
Thanks for having me. This has been great. Wow. Sales leaders, Ryan is a guy that I could talk to for absolutely hours. I love his presence.

The Power of Quiet Confidence

[39:18] I love how quietly confident he is and I really appreciated a few things about his insights from today.
The first one is around that idea of confidence. You know, too many of us as leaders, especially if we're newer into the role and definitely too many of our sellers feel like they have to project confidence by chest thumping and bravado.
And that just isn't the case. That quiet confidence, acting like you've been there before, whether you have or not, that projects real confidence, which increases our credibility with our team and our seller's credibility in front of their buyers.

[39:57] I also loved how we talked about imposter syndrome. It's something that I suffer with to this day.
I say sometimes that I really someday would really like to be the person that my team and my colleagues think I am. And I still do have some head trash about growing up in a village of 500 people and where I am today.

[40:22] Realizing that, you know, I am good enough and I am worthy of all the things that I have done and am doing and will do.
And the other big takeaway that I had from Ryan was his exercise of how many of you are out there.
And in his example, going down to, well, I'm one of 20 and we certainly are not going to walk into a room and be like, I'm one of 20 because that kind of sounds like a Star Trek reference.
However, when we realize where we are, what our echelon is, that can really increase our confidence as well because we realize that we are not just a small cork bobbing in an, ocean.
We are playing in a very finite pond and the right people are going to want our services because they will recognize that we are one of a very, very finite group.
Let me know what your biggest takeaways were in the comments and until we connect on the next episode, go create full funnel freedom.

Wrapping up the Full Funnel Freedom podcast episode

[41:26] Thanks for listening to today's episode of the Full Funnel Freedom podcast.
You can continue to support us by leaving us a review and a rating, sharing this episode with a couple of sales leaders in your network who you care about.
I'd love to connect with you. I'm easy to find, Hamish Knox on LinkedIn.
Also if you'd like a free 15 minute call with me, go to forward slash howtosandler.
Until we connect on the next episode, go create full funnel freedom.

[41:58] Music.