WHY NOT Wednesday with Daniel Hammond

Daniel Hammond, a former Army interrogator, uses a 20-minute diagnostic called "business interrogation" to help entrepreneurs identify problems and plan backward from success. He and his wife raised $235,000 to build a nursing school and clinic in Honduras, far exceeding their initial $50,000 goal.
Questions this video answers
14 years
He was in an E8 position while holding E6 rank (promoted to staff sergeant twice).
Initial expectation: $50,000; amount raised: $235,000 (raised over five years).
Interrogate 100 entrepreneurs before the end of the year (goal).
Approximately 25% complete (he stated "I am 25 of the way through").
Chapters
These last few years have made us question everything.
Our relationships.
Our jobs.
What constitutes an office.
And who we are.
In a.
World filled with chaos, confusion and uncertainty. It's time for some clarity. It's time to start understanding one another.
It's time to start understanding ourselves.
We envision a world where everyone knows their why. But even more, we envision a world where everyone knows their why. O s their why, their how and their what. The operating system that drives you, that lets the world know where you stand.
What your unique gift is, and most importantly, who you are.
YOS.
Are you ready?
Foreign.
And welcome to why Not Wednesday. We are here today with my good friend Daniel Hammond, the business interrogator. If that doesn't make you want to ask a question, I don't know what else will. Somebody who's a business interrogator and we were just talking in the pre show, Daniel, about me getting interrogated about a new venture that I'm starting. So I'm looking forward to that. But let me introduce you to Daniel Hammond real quick. I want to let you know a little bit about him. He is an entrepreneur. He serves in the senior leadership nonprofit role with a Central American focus on solving root causes of irregular migration in Honduras, El Salvador and Guatemala. His unique ability is to quickly adapt and build trust, absorb knowledge, discern connections, optimize strategies, overcome problems, and positively influence outcomes in order to maximize success, to protect against risk, to oppose evil and injustice, and to fight for what is right and true. You sound like a superhero, Daniel Hammond.
That's. That's part of my origin story right there. Dan.
I love that introduction. Tell us about it.
Yeah, it's. I think that people, when they're connected to who they are, what they.
What.
What they do better than anyone else. And that's what unique ability is all about. I learned that in Strategic coach.
Right.
And. And really understanding what drives you is. Is huge in life. And. And I think people who don't have that level of clarity in some ways are walking around a little zombified. Right. They a little aimless, without purpose. And I think.
I love getting clarity in what drives people and why certain things matter to some people and not other people. Those are fun things to interrogate on, man.
That is one of the best introductions. I always ask guests, hey, how do you want to be introduced? And I've got to give credit to whoever helped you come up with that because that's one of the best introductions I've read here because I know who you are based on what I'M reading I love, you know, where you talk about maximizing success, protecting against risk, but opposing evil and injustice and then fighting for what is right and true. How. How does, how does a person not get behind that?
Well, I wish everybody were on team Good Guy, but they aren't, you know, and, and so a lot of.
I believe that things go well when you work them from the bottom up. Right. I think a lot of people have solutions that they're selling top down that don't take us in a good way as a humanity.
Yeah, that is so true. Well, Daniel, one of the things I like to do to get started, as you know, I lead everything with my why.
And.
And of course, every guest that comes on why not Wednesday takes the yos discovery. So we did yours. And I like to introduce you to our audience because that's what they talk about. That's what they know is the yos. So let's talk about your why of better way, your how of makes sense and your what of contributes. So what we know about folks with your combination of why, how, and what is you're a constant innovator. You're somebody who's always looking for a better way and you're looking to share it. When you find a better way, you want to share it with others. And the way you find those better ways is by making sense of things that are complex and challenging. And I can see that we're both veterans. You were in the intel space. You like to solve problems. And when as you solve problems, you find better ways to help people. And then ultimately what you bring, what people can count on from you, is that you're going to contribute to their success. I can see your, your superiors in the army being very glad that they had a guy who was going to look for a better way to do things, who was going to make sense of what information you grabbed. And you probably got a lot of information as, as an interrogator and then ultimately contributing to the mission at the end. So how did that resonate with you, Dan?
Yeah, yeah. No does. And I was.
It was an interesting time for me in the army because when you're looking for a better way in the, you know, there's one way to do things in the army. That's the army way, and that's not always the better way. So finding out how to do things better enough and army enough to not get myself in trouble, that was a pretty fine line to walk. But what I think my superiors appreciated was when there was a job that nobody knew what to do. You could just throw me at it, and I would figure it out. And so I became sort of that.
Swiss army chainsaw of solving problems for them. And then, you know, usually when they didn't have that kind of work for me, I usually ask them a bunch of questions that made them uncomfortable, so they would look to send me off fairly often. But I did. I was blessed in that. My 14 years in the Army, I never worked a day in my rank. I was always in one or two rank positions higher than the rank on my, on my lapel. So that was unusual, I think, for the military career.
That is so good, Daniel. So tell me where you were. You. Did you start off as an enlisted soldier? Were you an enlisted soldier the whole time? And what was your rank when you got out?
Yeah, I was enlisted. I, I, I ended up, I was. When I finished, I was in an E8 position as an E6, and I was excellent. Getting promoted to staff Sergeant was so, so fun and exciting. I managed to do it twice.
Excellent, excellent. So you. Yeah, and I know, I know exactly how the army rank system works. I went in, I was an enlisted, and then I went through the ROTC program, and then I was an officer. Believe it or not, my first branch coming out of ROTC was to, in the military intelligence. And then I switched over to quartermaster, Then I became a quartermaster working for the third Armored Cab, and then I became a Ranger. You know, how many, how many quartermaster officers do you know that went to Ranger school? But I had that, that interesting opportunity to get to go to Ranger school and do that kind of stuff. One of the things I know you don't, you don't get to an E6, you know, and you don't get to an E6 twice without doing a lot of things Right. And one of the things you mentioned is you were always in a position that was probably two ranks above where your current rank was. What was, what was it, you think that helped? You always be at a level above, and you've talked a little bit about your yos, always looking for those better ways, so we're going to dig into that, too. But what was it that allowed you to operate at a higher level?
Yeah, I think curiosity is probably the biggest thing, is.
You can't give me a role. You know, I'm not, I'm not a guy that's going to sit here and push a button every five minutes, right. I'm going to get insanely bored, and I'm going to cause probably more problems than I'm Worth. So I was always curious as to not just what was I responsible for, but what is everyone around me responsible for and what maximizes success for the team and then for the higher organization and the higher organization above that. So I was always questioning even before I was an interrogator. You know, what does victory look like in this place? Right? And sometimes it's a simple, you know, we need to go get this box checked so we don't get in trouble. But you can also find, well, if we need to check that box, is there anything else we can do of value? Is there some good training we can get out of this? Is there some way we can make it less miserable for the team to go check this box? And that's one of the. Actually getting promoted to E6 twice is not a good thing because it meant I got demoted at some point as well, when, when, you know, I had a health issue that prevented me from checking the box. So, you know, it's. It's not always easy to do things the army way. And a lot of people, a lot of times you'll run into a situation where what's in it for me prevents people from doing their best. And, you know, I lived in a third world country as well, and I think you see that in first world countries as well, in bureaucracies. Right? You know, like, why should I help you? Because it's your job. They need to know their why better, I think.
Well, you. You bring up something so important, and it's something that obviously you did, Daniel. You did more than what was asked of you. And it's so important in whatever you're doing, whether, where you're. Whether you're in E1, private or you're. You're a master sergeant, do more than what's asked of you and be prepared. Because one of the things you. I know you learned because you're a combat veteran is you got to be ready for. To take over for your leader if he's gone in the next minute. And. And so it's one of the things the army preaches, hey, you gotta. The mission has to get down to everybody. But as a better way guy, as someone who's always looking for a better way.
I'm sure it was a challenge for you because there have to be times when you said there's a better way to do this, but they're asking me to do it this way. I am. And feel free to share if you want to, but I'm sure that had a little bit to do with it. You mentioned a health issue. Did that have anything to do with your having to be an E6 twice?
Yeah, actually, no, that, that time didn't. But I got. There were plenty of other brushes with trouble that I got into because sometimes you're ordered to do things in ways that are not particularly productive. In fact, one day I was ordered to go dig up a motor pool with my team with our entrenching tools and the concrete, it was like concrete down there. So that was not a better way. Especially since we had picks and shovels underneath every vehicle. It's like, why are we going to take our little, you know, aluminum tools down there to be destroyed when there's a better way? So that, you know, and, and I'll even go on to say it didn't make sense and it was going to limit our contribution. Dan. Right, yeah.
Well, it's not a bit. Yeah, absolutely. It's not a better way. It didn't make sense and certainly wasn't going to contribute to the, to the well being of your troops that you're in charge of. And so I'm sure you pushed back. How did that go?
Well, I didn't get devoted, but I got, you know, when, when, you know, a lot of times, and this is sort of one of the things that I have is an operating system for organizations and a lot of that top down hierarchy gets in the way of doing things better because a lot of times the people at the bottom understand the problem better. And so when you have, let's say a commander, say our, our motor pool needs to be ready for an EPA inspection and then he tells the battalion commander, who tells the company commander, who tells the platoon leader, platoon sergeant, you know, section sergeants, and then you get ordered to take the wrong tool down there because somebody just decided, well, that's how you, we're going to solve this problem. There was a better way. Nobody asked. But if I'm ordered to do something and it's not an illegal order, I can get in trouble, in significant trouble, you know, like thrown in jail and lose my pay kind of trouble. So, you know, you have to make that balance. But for me, it's what best accomplishes the mission. And it's, it's, you know, a lot of times it's telephone game.
You get things muddled. Whereas, you know, somebody asks what does success look like for you really? If we never left the motor pool where it wouldn't pass an EPA inspection and the expectations were set at the lowest possible level and we were given the tools to make sure that, you know, we had drip pans under our vehicles. You know, we would never be down there chiseling the motor pool with picks and shovels. Right? So there was a better way. But you know, a lot of it is it's a hierarchical system and they are going to tell you what to do. And they many times think they know better than you do, you know.
You know, Daniel, you bring up a great point. What I have found in, when I was in the military. So I share a similar why in your yos of challenge the status quo and do things differently so that can get, that can get us in trouble. Whether you're looking for a better way or you're saying, hey, why do we have to do it that way? That often leads to a conversation behind closed doors with higher ranking officer or non commissioned officer. Right. But what I found is the best leaders did exactly what you talked about. They understand that the knowledge exists in the motor pool, the knowledge exists with the troops. So instead of saying, hey, this is exactly how I want you to do it. You give them the mission and then you say, how do you think we should do it? And it's not always a democracy, of course, there's some things you have to make quick decisions and this is how we're going to do and we're going to move forward. But I found that those leaders that said, hey Dan, what do you think we should do? And allowed me to use my creativity and allowed you to use your creativity probably were the best leaders you worked for.
Agreed. And I think, you know, there were times when, you know, it's deployed, you know, in a combat scenario and you know, there were, let's say, ten commandments of interrogation. Right. And you know, we wrote the, we wrote the policy for our unit because my partner and I were both instructors and so we knew the policy better than anybody else there. And the leadership said, okay, you can do these five rules, but not these five rules. And we're like.
Brain broken. Right? That doesn't make any sense. But eventually I got a detainee important enough that I was able to go back and say, hey, look, I really need to fight for these other five things because it's going to impact my success. Success, which is going to impact your success. So I, I literally got a two star general to sign an exemption to a bad policy.
So that I, that we could do things in, in this particular circumstance the right way. And if I hadn't done that.
Things would have gone hijacked. I mean, within 24 hours there were already people making requests that would have happened had I not gotten that exemption to the policy to follow doctrine, which.
Is weird to follow all 10 of your suggestions, 10 rules that you have. So Daniel, how have you, I mean, amazing stuff that you've done and, and I see you've got these licenses and certifications that, so you've kept up your skills. How have you translated? Unlike infantrymen in rangers, when, when, when we get out of the army, there's, there's some skills that we have not very useful in the civilian world unless we're going to be police snipers and or SWAT teams. You had a great set of skills that you've been able to convert to what you do in the civilian world. And you even have what's called a business interrogation. So tell me how you were able to do that, how you, how you use this, all the many skills of certifications you earned in the army to make to help businesses in the world that you operate in today.
Yes. So really I, I have a toolbox and I'm always looking for new tools to do new, new things. Right. I'm not, not a construction guy with a garage full of tools. But you know, figuratively, that's what I, that's what I do. I'm always looking to grow myself. I'm always looking to provide better ways for me to serve. Right. And so for me, you know, as I journey, I get bored with something and then I need to learn something new. And so I'm constantly looking to evolve. You know, I invest a lot of money in coaching, you know, being coached by people who know better than I know. And so that's.
I think I respect specialists in an extreme way. When you can reach a level of mastery in a job and understand it and believe me, I've run across those people. You're in a middle of a complicated web of processes and there's one person that always knows what the right answer is. But I'm pretty good at asking, well, how do all the connections work and what's important to each person here? And it makes me really good at being able to bridge the gaps between expertise and, you know, that's one of the things that, you know, I've delivered cyber exercises.
I've worked with cabinet level officials in four countries in five completely different job roles. So, and it's not, it's not something I seek, but it's something that I just end up being the right person to engage at a really high level. And you know, I, I, I appreciate the uniqueness of Each person, and I like to connect with them on a personal level in a way that's appropriate and helps everyone succeed. So, you know, for me, knowing sort of the whys of others is really important in, in bridging high level gaps. I mean, I, I literally, you know, the cabinet level officials I've worked for are no less important to me than the privates I was in charge of in the, in the military. Right. I mean, everybody has a value and everybody provides a value. And I think, you know, the military teaches you a lot of things. So I would never discount.
That there's any kind of less than value for whatever you did in the military because you had to get, you had to understand this culture that you're in. And you know, I guess the, the biggest challenge is knowing what to let go of and what to, what to embrace in the new culture you're stepping into. But it's certainly transferable. And I definitely, the veteran.
People that I've worked with, in corporate, in nonprofit work, they've all been fantastic. And I've done a lot of veteran volunteering as well.
There we go. Speaking of that, Daniel, tell us about business interrogation. What is a business interrogation? Because in the pre show we talked about it, you've got a goal of interrogating 100 business, business interrogating 100 entrepreneurs before the end of the year. So what, what is a business interrogation and why do you have that goal?
Yes. No, thanks. I appreciate that. For one.
Let'S say that, let's say you have a project and you have the perfect tool for that project, but you left that tool at home or, or you don't know how to use that tool. It's not very useful. So at one level, I want to add value to people, but if people don't know what I do and how I serve, then, you know, it's hard for them to find me. So I came really in October, realized I need a brand. I need something that says this is what I do and how I serve people. And business interrogation. I was an expert interrogation instructor. That was a level of mastery that I achieved before I got out. I was a contract interrogator and I helped design an advanced interrogation and analysis course for the US Military. I also did a lot of scenario design work and built complicated puzzles for interrogator analyst teams to solve together. So I'm really good at breaking systems down, seeing what works, what doesn't work, asking questions. I, I was the lead developer of the advanced questioning course or class within this curriculum. And so And I also, you know, going back to my unique abilities, I build trust fast. I, I care about people and I'm not looking for a solution that works for me. I'm looking for a solution that works for you, your employees, your customers. That's, that's the solution I'm looking for. So business interrogation is a 20 minute process where I interrogate an entrepreneur. I ask them, what is your biggest business challenge? Typically that's one of three categories. It's where do I have a problem? So it's a problem that needs to be solved. The other is I have a process that I'm not happy with. So there's, there's something there. I don't know exactly what it is, but it, it needs to be optimized, let's say. And the third one is I'm doing something I've never done before. And then usually I ask them questions about, well, if it went as well as you could imagine it would go, how you know, what's the end result. And then I help them backward plan how they can, you know, create the, the actions that get them to that success. And I look for where are some hidden risks along the route and where there's some hidden opportunities. Because even if you get clarity around, oh, I'm sure that there's no risk on this path, you might be running past some opportunities and some extra, leaving some extra money on the table. So I always help with that as well. And I do it in a 20 minute time period. It's, it's fun for me to keep honed on my focus for the client sitting in front of me. And then I write an interrogation report with some insights and maybe if I see, hey, I could help support you be successful in transforming this system or achieving this goal or solving this problem. Then I list some opportunities of where I see we might be able to collaborate for their success.
So, so you've got a system. You know, it sounds to me that clarity is a big, big part of this. And so asking the right questions is probably a skill that you learn from, from your interrogation background. Why 100 entrepreneurs before the end of the year.
Yeah, I want, so.
Well, we can talk about this now, right? I was unpublished a year and five months ago and our fourth book, my, the book that we've written together, which is Voices for Leadership Volume two, which is currently available in Kindle and will be live on Friday. We would love to have your support for that initiative. I've written, I've been the lead author on two books already. Collaborations, talking about customer driven leadership, which is the operating system. My partner invented it. And then I also have done. You can maybe just see up in the corner there, Success Secrets of Disruptors. That's another collaborative book that I participated in and may have influenced the naming of. I love to disrupt things for good. I love to ask you the hard questions that maybe you wish nobody would ever had ever asked you. But once they've been asked, then all of a sudden you start thinking, well, it's not going to be that hard to make it better. So going back to better way. Right, right. And then I've got two of. One other collaborative work is already submitted and that should be out in a few months. I've got an invitation for a sixth and then I want to use these case studies, these 100 case studies, anonymize them and weave them into my first solo book called Businesses Interrogation that talks about, you know, what are the types of questions you can ask yourself to improve aspects of your life and your business.
So which type of entrepreneurs do you want to interview, Daniel? If someone's listening and says, hey, I want to. That sounds like something I want to take part of. I want to contact Daniel who. What type of business owners or entrepreneurs are you looking to talk to?
Yeah, well, first of all, if Business Interrogation scares you away, that's probably, you're probably not the kind of entrepreneur I want to work with. And I chose that name intentionally. Right. It's got a little edge to it. And I'm going to ask you questions and I don't care if they make you uncomfortable because my goal is to ask you the questions that help us find that better way. So to that end, you know, I love. So I'm in a strategic coach 10x ambition program. There are a lot of insanely successful entrepreneurs there. I love doing interrogations with them. The more complex the issues, the more fun it is. The more irons in the fire you have, I think the better we'll work together on a long term relationship. I would love to be kind of on a retainer with some global changing entrepreneurs. Entrepreneurs just to help them. You know, Daniel just have being that extra thinking partner, strategic advisor in the room that says, hey, maybe there's a better way here or maybe there's a risk that you need to at least consider. And, and maybe we can come up with a way that we can avoid walking into that trap.
Yeah, that, that is perfect. So where are you on your, on your number? I mean you've got a hundred before the end of the year. We're on November 15th. 15th. You got 45 days, Daniel. So how's that going?
I am 25 of the way through, so.
25. So you. You've got a. You've got some work to do. Any what. What? Any. I know you've got a strategic plan to get to that 100. I know I'm one of those people you're going to be interviewing, so I know you now. We're 26% of the way.
Yes, thank you for that.
And.
And really, you know, the number's. The number.
I'll. I will, you know, if I get half that number, that's fine. But at some point in December, I'm going to stop taking other calls, and I'm only gonna, you know, if you want to talk to me, it's going to be for an interrogation. And so I think the end will kick out a few as people hopefully are aware that. That I'm doing it and are. Think have it in the back of their mind. But, you know, 101 would be better.
Yes. Well, let's. Let's do this. You probably have quite a few of these, but our signature question is tell us about a why not moment, Your biggest why not moment. A time in your life when you said why not to something and you're so glad you did.
Yeah, I ran into a situation, Dan, where.
The priest at our church had run into a priest in Honduras that had a nursing school, and it was not up to code. She was teaching out of her. Out of her, like, community room, and they were going to shut down her nursing school. And so my wife and I said, why not? We'll try to help you raise some money to build the school. And we said that in 2015, figuring we would have to raise $50,000 and having no idea where we were going.
To find that money.
Five years later, we had raised. We, you know, had grown the team, and we had raised $235,000. Not only built a modern nursing school at that church, but also a local clinic where people could get, you know, basic health care needs taken care of. And they have doubled their capacity for students as well as now are within code. So that helped me run into my partner in customer driven leadership. And so truly, it has transformed more ways of my life than I can imagine. And most of those students were single moms looking for some way to support their families. And there was a huge medical shortage in Honduras, So it's transforming how medicine is done in this region of the country.
That is an outstanding why not answer. And I really appreciate, let me say thank you on behalf of the world for saying why not to a big mission and to help an underserved area. And that's the work that you're currently still involved in. I love to hear that. You know, Your goal was 50, 50k and you 5x that and more, more than that, you're still continuing to support it. So, Daniel, I want to thank you for being on the show. What do you say we, we end the show on that positive note?
Why not?
Thank you so much for being on, Daniel Hammond. Thank you for the difference you're making. Thank you for being a co author in our book, which you were. We were able to get that in there. I know Brian Brogen is going to be really happy that we did that. And we're going to share this with the world. We're launching it very soon and it'll be available on Amazon by the time this show airs. So I hope you get out there and get voices for leadership. Thank you for sharing your wisdom, your story of success with Wine Nation today. Daniel, we look forward to being interrogated by you.
Thanks. Appreciate it so much, Daniel.
Have a great rest of your day and we'll see the rest of you next week on why not Wednesday?
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