How to Scale Without the Chaos: Smarter Growth for Founders with Chris Davenport II #101

Scaling a business beyond its early wins often reveals deeper cracks; misaligned teams, operational bottlenecks, and a drop in service quality. In this episode, Chris Davenport shares battle-tested strategies for overcoming these growing pains and building healthier, more resilient organizations.

With a deep background in tech and nearly 30 years of entrepreneurial experience, Chris brings fresh perspective on hiring smart, leading with clarity, and running meetings that actually move the needle. His approach blends structure with emotional intelligence helping leaders foster real accountability and trust.

GUEST BIO:

Chris Davenport II has nearly three decades of entrepreneurial experience, including building and successfully exiting a technology company. He’s faced the full arc of the business journey; success, failure, and everything in between.

As a certified EOS Implementer, Chris now coaches and mentors business owners to gain clarity, strengthen accountability, and scale sustainably. Through a blend of proven frameworks, tech-savvy insight, and a strong focus on people, he helps leaders turn complexity into structure—and stress into momentum.

Chris's mission is simple: equip business leaders with the skills and mindset to confidently grow their businesses and transform challenges into successes.

TOPICS EXPLORED:

• The biggest scaling challenge for small tech businesses: operational maturity lagging behind growth
• Why hiring friends or family often backfires and what to do instead
• How one effective weekly meeting can transform accountability and communication
• The key metrics every role should track to drive team alignment
• Balancing under-communication vs. meeting overload in growing teams
• How to create a culture where employees feel heard and valued
• The listening habit that builds trust, reveals hidden issues, and improves negotiation outcomes
• Why emotional reactions in negotiation often mask deeper fears and how to respond instead
• Building partnerships, even with competitors, through integrity and open dialogue
• The surprising upside of addressing fears early in business relationships

RESOURCES:
Chris Davenport Next Level Leadership Academy: https://chd2.com/

Chris Davenport Free Consultation: https://chd2.com/book-a-call/

CONNECT WITH CHRIS DAVENPORT II:

 On LinkedIn: https://www.linkedin.com/in/chd2/

If you're interested in more visit ▶ https://almcbride.com/minicourse
for a free email minicourse on how to gain the psychological edge in your negotiations and critical conversations along with a helpful negotiation prep cheat sheet.

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Transcript

Al McBride  0:00  
welcome to the dealing with Goliath podcast. The mission of dealing with Goliath is to sharpen the psychological edge of negotiation, ethical influencing and high impact conversations for business leaders who want to be more effective under pressure and cover hidden value and build greater connection and business relationships, all while increasing profitability. This is the short form espresso shot of insight podcast interview to boost business performance in around about 15 to 20 minutes. My guest today is Chris Davenport starting growing and running a business is one of life's toughest challenges. With nearly three decades of entrepreneurial experience, including building a tech company from the ground up, Chris has navigated success, failure and everything in between. As a certified EOS implementer, Chris coaches mentors and guides business owners to achieve clarity, accountability and structured growth, leveraging proven methodologies, technology expertise and emotional intelligence. He empowers leaders and their teams to overcome operational hurdles, implement best practices and create a thriving, less stressful business environment. Chris's mission is simple equip business leaders with the skills and mindset to confidently grow their businesses and transform challenges into successes. Chris, welcome to the show.

Chris Davenport II  1:25  
Al, thanks for the great introduction there. I appreciate that. Well,

Al McBride  1:28  
there's a lot, there's a lot in there to talk about. Chris, love to break down. So let's dive into it. So who exactly are your ideal clients, and what tends to be the biggest challenge that they face.

Chris Davenport II  1:42  
My ideal clients, you know, really circle around the experience I've had as an entrepreneur. So I've, I worked a ton of my time in the technology space, and while I was there, I did, did work through cybersecurity. You know, you hear that buzzword thrown out, thrown around a lot, and also worked as something called a managed services provider, which is basically a fancy way of saying Help Desk and professional services to the outside world. And you know, really their revenue somewhere between 1 million, up to 10 million. And I'm looking to help those guys, because they're they're typically challenged. Costs with their vendors are going up. Client acquisition cost is going up. There's more, you know, turbulence in the marketplace with, you know, people that the barrier of entry into their business is low, but the experience, you know, is vastly different from someone who's just starting out to someone who has a real business that's operating and functioning. So I'm really looking for those businesses that are stuck there. They've hit a ceiling, you know, and their operational maturity really hasn't scaled alongside their sales and marketing efforts, you know. So these are people that have had success, and they found clients, and they have those evangelical first 10 clients to get them started as a real business, and then they go hire employees, and they expect everything to be great and the same, and they find that the employees don't have the same oomph that they have, you know, when it comes to servicing the customer and And so I help them get aligned as a team and figure out how to communicate that to their internal teams so that the experience is great through the organization. That's ideal client there.

Al McBride  3:54  
So, yeah, no, it sounds very interesting. So it sounds like, as you said, they have that initial Verve they know their customer enough to be landing those decent contracts. They're fulfilling them quite well, but as they expand, that doesn't translate. It gets diluted. Yes, right? So what are some of those common mistakes then that people make when they're trying to solve that problem? What are they what do they usually try that hasn't worked before they meet you.

Chris Davenport II  4:22  
They, you know, a couple of things come to mind. I'd say the first thing they try is they just, they hire people that their friends or their family members, and they they have a trust for them. I say this too because I even went through this early on in my journey, and that's not always the best approach, because if you're starting out and you're not a seasoned entrepreneur, it's difficult to deal with people issues alone. So if you add in there a friendship or a family connection, it 10x is. That conversation difficulty level, and they're not, typically, they're not the right person to pick to, you know, to complete the job that they're they're looking for. So I'd say not looking out, not finding the best person for the role, and being patient at finding someone, and because I know trust is hard and trust takes time to build, but making sure you hire the right people versus just hiring who's around you or who you're comfortable with to to to get the desired result, it's

Al McBride  5:37  
an excellent point, because, as you said, if there's personal relationships there they make every, every conversation where there's friction a lot more stressful, yeah,

Chris Davenport II  5:47  
yes. And Al, I'll say it, that's it's tough, and it's one that I overcame, because in my last business, I worked alongside my wife for 10 years. Wow, and we have a great relationship, and people look at us like we're insane, which we probably were in the beginning, but we figured it out, and it just takes some maturity to get through those conversations being awkward, and that's so that's why I say don't start out hiring your friends, hire someone that knows what they're doing, and they have some experience, and you'll you'll sleep better at night doing that,

Al McBride  6:30  
it's a great point. So what would be one valuable free action that the audience could implement that will help with with all of these issues that you're talking about when you're growing to that sort of size, and as you said, you're feeling a bit stuck. You're hitting that plateau. You can't seem to get through the ceiling. So

Chris Davenport II  6:48  
you know, the best action is to learn how to have an effective weekly meeting with your team. And that sounds so simple. Al, but it's, it's an area that people, either they go one way or the other way that they you find the people, oh, we hate meetings here. We never have them. They're a waste of time. Or you'll find the other side of the pendulum. Oh, we have, we have daily meetings, morning and night, you know. And everybody's in sync, and death by meeting, as they say. But the if you have one weekly effective meeting where you drive accountability and accountability through, you know, checking in on your numbers, whatever that number is. You know, in sales, it's pretty easy to come up with numbers, but make sure each role has a number that's relevant to your business and the goals that you have and and then just checking in, talking through issues. So having giving a space and listening, being a good listener, hearing the issues, pointing them out and helping the team together solve the issues. And so when you do that, you drive accountability, you increase the communication level through the organization. People feel like they are heard and make a difference and are part of something. And you know, last but not least, you you just give air time to these team members, to to have somewhere to, you know, share a grievance or an issue or a win. And it does away with all the meanings in the in the hallways. And it brings everybody in sync. Every week, everybody gets back in sync together, excellent,

Al McBride  8:44  
as if it's the right level of communication that's needed in the right type, yes, structure, yeah, it makes a huge difference, because people know enough about what each other are doing, but not so much as you said that it's constantly being interrupted from doing the actual work. Yes, which, which is really quite tough, but people some, so as you say, some companies seem to like that, yes. So what would be one valuable free resource that you could direct people to that would help with that?

Chris Davenport II  9:13  
I've actually got some, some class work that I have done, and I give away a good amount of of the lessons that I help IT companies and SAS companies, MSPs. So that's on my website at CHD two.com and so I I have a link there to different resources that will help you with some of these things. And I am working on an example of this meeting, just, just a real life example to show people what it's like, so they can, you know, implement it themselves.

Al McBride  9:50  
Very good. Yeah, it's a great it's a great idea. First of all, thank you for for sharing that. That'll be very useful. But the before and after, nice one. Here's how to do it. Right? Yes, better if you want to be diplomatic. But yes, yeah, exactly. Now that that's again, just to reiterate and to double down on that for some of the listeners and viewers out there, it's something that I usually do when I work with client companies as well, where they're they're not talking enough to each other, which I find is more the case, or, as you said, there's over communication, but how detrimental it can be, because it burns through a lot of good will people otherwise have for their colleagues. It does so it is massive. I know it sounds simple, but it's absolutely key. So what would be your number one insider principle on how to negotiate or build, build, rapport, connection better.

Chris Davenport II  10:45  
You know, I've thought a lot about this, and I wasn't always good at this, but I over time, and in my career, I've I've learned that when you become a great listener, you become really good at negotiating and and helping and whatever the situation is just, just being a good listener. You know, God gave us one mouth and two ears for a reason. So it you know, as a leader, you need to aim at speaking less than you know others and listening, taking in what they're saying, and really mirroring back to them in a different way, something they've said to you to make sure that they know without a doubt that you're listening to them and you care, and so you're basically meeting them where they are. And they need to share this, and they need to talk about this, and whether it's in a negotiation, everybody's got what they you know, you know they're cloaking what they need, and listening and allowing them to to communicate to you is a good way to find out where they are at. And I'd say the most negotiation breakthroughs happen when you you know when, when you listen and you start to identify the underlying emotional pieces of that thought that they're sharing. Because when we're when we rush to say things, emotion is typically met with emotion, and the emotion is not the root issue at hand. It's something else. Emotion is just the reaction of the fear or the distortion that we have inside. So by actively listening and genuinely empathizing with people, you'll build that deeper rapport and trust, and then you'll uncover, you know, hidden opportunities, absolutely,

Al McBride  12:42  
absolutely. I mean foundational, fundamental stuff, but, but as you said, it is, it is that first key, well, foundational piece to building trust? You know, there's all these stats about people when they go into negotiations of all sorts of positive intent, but they quickly get into the fear factor by misreading little cues. Whereas, as you say, when you can actually put your ego aside for a minute and just listen to the other side and ask curious questions, open questions, and then, as you say, mirroring back to ensure you're accurate, yeah, this is not rocket science. But ask people how often they do it. It's

Chris Davenport II  13:27  
it really isn't rocket science, and I think that people are afraid to do it because they're afraid they're going to lose something by not just speaking. And I have hundreds of examples of that not being the case, you know, just closer relationships, you know, and the space, the the spaces that I work in, I become friends with my competitors. You know, before I sold my company, we would work for each other. And there was a period of time where, where a third of my revenue came from competitors and working for them,

Al McBride  14:05  
wow. And that's some good relationships, right there, yes. And

Chris Davenport II  14:10  
part of that is being a good listener and building trust. And you know, if they're worried about, you know, hey, I'm worried you're going to take my client, well, I have something for that. And then you just the level of trust is built higher and higher to the point to where you know, you end up doing an acquisition and and it just makes, you know, with that person down the road, and it made it so much easier, because we'd already worked together. And it just was a was a great thing to see happen.

Al McBride  14:39  
Absolutely. That's a fabulous example. Yeah, you know, where, as you said, the bravery to have that level of not just engagement, but relate, business relationship, and then, as you said, the trust built over time with your competitors. Because a lot of industries, it some industries, is more normal than others. You know. That abundance mindset, shall we say, whereas others are all protect, protect in all cases, don't give nothing away because they think any sort of gesture in that direction could be seen as weakness and all that sort of stuff. That's right, may I ask, how did you get over that, and maybe that initial or occasional fear that any of that good will be used against you. Or did you just accept that was a small possibility, or

Chris Davenport II  15:27  
I accepted it was it was a possibility. And when I started out with these relationships, I did have some fear. At first, I did have a unique position, because I was typically on the other side of it. So I was the one providing services for their company. And I just, I always like to do the right thing, and so I think I led by example, and then when reciprocally, they would need to, we would need their help. I I just didn't have any worries, because I knew I'd treated them right. And so that really helped just leading, leading with honesty and openness. And if you had a fear, just get it out on the table and say it versus, you know, holding it in and worrying about it, and that really seemed to help curtail the, you know, any of those fears, and never had an issue. You know, 1000s of tickets, you know, issues helped each other back and forth. Never had an issue with someone stealing a client, or, you know, breaking cover causing issues. It just never, never happened.

Al McBride  16:44  
I love that. That just the profitability of integrity. Yeah, it's what we all want to be true. But that's right, fear, it's not quite, you know, yeah? So excellent. That is a fabulous message, and fabulous, as I said, business history that you've managed to achieve that, yes, I would imagine you're quite a good judge of character in the first instance. And you go with your gut.

Chris Davenport II  17:11  
People tell me that around me and and it's you know something about having, you know, having a good eye for, you know, honesty. It does come with experience. And I don't think it was something I was born with. I think it was learned and watching and seeing what someone with integrity, how they operate. And then, you know, unfortunately, sometimes you see the opposite, and it's glaringly, obviously different. And, you know, typically, though, those, those were issues that happen internally with employees in my case. So, Okay,

Al McBride  17:52  
excellent. Well, look, thank you for your honesty today and and so where can people learn more about you, potentially even get in touch? I see you're on LinkedIn, quite a bit. I'm

Chris Davenport II  18:02  
on LinkedIn. My handle there is CHD two, which are my initials, and then I also have a website. It's CHD two.com,

Al McBride  18:12  
excellent, see, and that's with the number two, right? Yes. Thank you. Excellent. CHD two, excellent. Thank you so much, Chris, for your time. It's been a pleasure. Yes,

Chris Davenport II  18:21  
thank you. Thank you. Al appreciate it. Cheers. You.

Transcribed by https://otter.ai