310: 5 Steps to Better Listening with Alana Dobbins

https://youtu.be/l5fLRKRgpQc Alana Dobbins, Executive Director of the Business Owner Success Alliance (BOSA) and Business Development Specialist at W.G. Nielsen & Co., shares how servant leadership and active listening help advisors and entrepreneurs make smarter, faster, and more aligned business decisions. Alana introduces the 5-Step Listening Framework she developed through her extensive experience in investment banking and business development: Mandate, Plan, Team, Execution, and Self-Awareness. This framework helps leaders build trust, uncover risks, and strengthen alignment between vision and execution. She also discusses BOSA, an upcoming mentorship platform connecting business owners with trusted advisors through short, video-based guidance — creating an accessible way to get sound advice at the right time. From building chemistry with clients to balancing empathy with accountability, Alana shares how genuine listening and mentorship drive growth and confidence in the world of M&A. — 5 Steps to Better Listening with Alana Dobbins Good day, dear listener. Steve Preda here with the Management Blueprint podcast.  I’m the founder of the Summit OS Group, which developed the Summit OS Business Operating System. And today my guest is Alana Dobbins, the executive Director of the Business Owner Success Alliance and The Business development specialist at W.G. Nielsen and Company and Mid-Market Investment Bank in Denver, Colorado. Alana, welcome to the show.  Hi, Steve. It’s such a pleasure to see you again. I enjoy every time I get to share a conversation with you.  Yes, you’re referring to me being a guest on your podcast, which I very much enjoyed, and I’m sure this one is even gonna be better than that one. So let’s get into it. And, you know, I’m very interested in what drives people, and I always ask on this podcast, what is your personal why and what are you doing to manifest it in your professional life?  I love that question. I’ve seen you ask that on the podcast I’ve watched yours. Gosh, everything is different when you get older and over the years you realize what is important to you, and I wanna live a good life. And I don’t wanna walk by somebody that needs help and not help them. I don’t wanna over promise and under deliver like I have in the past. So I think that would be my why, and manifesting that in my career, it's every day we're serving business owners every single day in some capacity we're showing up Share on X and we’re utilizing skill that we’ve built over my 25 year career, your wonderfully distinguished career, but we bring that to the table. So I think manifesting living a good life is to really utilize everything that I’ve honed and I’ve developed, and that can be put to make someone else’s life better.  Yeah, it is so true. And when I was younger, even not that much younger, even a few years ago, like 10 years ago, I wasn’t really aware of this whole idea of why it’s important to think about who you are serving and how we are helping people, but it’s really a huge tool to empower ourselves to do our best work. And also to be able to have a long-term perspective, which helps iron out some of those rollercoasters that we all face. So yeah. You love your servant philosophy. You have developed an organization called the Business Owner Success Alliance. So what made you want to be involved with this organization and what is the mission of this organization? What I’ve seen and witnessed over my career are the business owners who are in growth mode, the business owners who are looking to exit the business owners who are leaning on others for sound advice, to make business decisions. And I’ve been very fortunate to have been exposed to this environment since I was 19. I was very fortunate for that and in seeing so many different types of business owners. The mission around BOSA is to bring together advisors and mentors that have sound advice that can very easily address something that might change the trajectory of a business owner's decision and having that advice at the right time along with it… Share on X We wanted to bring that in a way that was digestible. Connections can be made on BOSA where if an advisor and a business owner want to establish some sort of ongoing relationship, that’s completely up to them. But we wanted to bring an opportunity to have a business owner pop a question out and get a response, a 15, 22-second video response from someone that has valuable advice that can possibly help them make that decision at that moment so they can position themselves to do the best they can do in leading their companies.  Wow, okay, so this is a unique format. It sounds like, that you’re not bringing the peer groups together live, but it’s more about communicating through asynchronous video. And giving them a platform where they can look at other questions that have been posed and review other content as short video snippets that they can easily digest and go, ‘Oh, I need more information on that. Maybe I’ll reach out to that advisor’. But having that video library of other things, business owners in their realm, so questions that mom and pop business owners have are going to be different than established businesses in growth mode. So we have a dynamic way of allowing the person that owns the company in growth mode to see relevant contact and vice versa for the other stages of growth.  I love it. This is very interesting. And how many members are there in this alliance?  So we haven’t launched our platform yet. We are taking pre-registration via our website, and so we have quite a list of business owners and we’re building up our business advisors. When we want to launch, we want it to really add the value that we’ve built it for. So, we’re looking for additional mentors and advisors. We have quite a few business owners who are waiting. So we’re in the process. So if you’re a business advisor with an excellent career that you think you might be able to donate a little bit of your time. Mentors that are leaders in various different spaces, that’s what we’re looking for.  It’s so important. I actually was asked to do a keynote last week and there were only very short time, I only have 20 minutes and I picked three topics. One of the topics was mentorship and how important it is and actually looked through my life and I realized that I used a lot of mentorship, but I also missed out on a lot of mentorship. And I think the better mentors you find, the faster we can grow our businesses. So I allowed this initiative. I think this is very smart and very useful.  We’ve been exposed to so many in our careers. I know you and I have talked offline and so many in our careers have taken the time to lift us up and help us through things and, and teach us. So this is an— it’s giving back, but it’s also allowing an avenue where the newest and greatest tools, you know, forget AI. I love AI. But this is one-on-one real advice from experienced people.  Yeah. And the couple of things there I’d like to mention. So, you know, AI is very useful. It really helps with productivity, but a couple of things AI cannot do. So AI is not always able to filter information. It can create a lot of information, which is sometimes overwhelming. But you need wisdom, not just information, and you need to filter this. And mentors are able to bring that wisdom to the table. Mentors can also give you validation sometimes, you know, because as entrepreneurs we don’t just need good advice. Sometimes we need someone who actually gives us some encouragement so that we are doing good work, even though we are struggling. And the third thing is accountability. So again, it’s not possible to be accountable to a machine, right? But it is to a human being. So AI, ChatGPT is not replacing mentors. For sure.  Well, and when you mention all of those, it’s, you know, the failures that we learn the most from. I don’t think AI can draw from its failure in business. You know, there’s going to be triggers in our mentors and our business advisors history that something that triggers something that they failed on, that they had to really learn the hard way. And, helping business owners avoid that. That’s our mission really.  And really, you are not gonna learn big things without failing big, I believe, because that is the forcing function to push you to be creative, find a solution, and then it could be a unique solution, which then gives you a competitive edge. So it is huge and mentors can help with that. Alright, so obviously the reason you are putting this together, because you are, and I experienced this when I was on your podcast and you were asking the questions. You’re a really good listener.  Thank you.  And I think that’s why you have utilized a five step listening framework that you talked about in, on the pre-call to this interview. I’d love you to share it with our listeners what those five steps are and how do you go about, you know, actively listening with this framework.  And you know, when we talk about framework, we all make whatever we’re doing specific to our world, our universe who we’re helping. And as an investment banker and someone that’s been doing mergers and acquisitions for a very long time, I've found that this process of listening, it not only applies to my industry, but every single person that is running a business that has a specific job, it's helped me immensely for years and years. Share on X I wasn’t the best listener. And when you come, everyone says, well, know your audience. Know your audience. It’s not just about knowing who you’re talking to, it’s about understanding what you’re trying to get. What is the mandate of this conversation? Why am I here? So the first part of active listening for me is really taking a minute and going, okay, what am I looking to get out of this conversation? But what are they expecting? In this conversation that I could bring to the table that they’re expecting me to bring to the table to it speaks to alignment. Alignment in our world is so important. Alignment around what we're trying to do for a client, what our client is trying to accomplish in a merger acquisition transaction. Share on X What are our goals? How are we aligned around those goals? Bernard Ferrari, he wrote a book called Power Listening. Wonderful book. I would suggest anybody, business owner, advisor, anybody listen, read it or listen to it on Audible. So that first part of my listening, active listening process is your mandate. What are you trying to do and aligning around that. Why are we here? You could apply that to, why are you running a business? What are you trying to do? Or why am I here with this client? What are they trying to do? So that, I would say the first part of the active listening processes, understanding the mandate of the conversation. So, now that you’re present and you’ve, you’re aligned and you’ve brought to the table what you’ve come to talk about. What is the plan? So in a conversation about with a business owner, maybe I’m going to ask him, you know, what are the specific objectives that you have in place to accomplish your vision? So getting a plan, conversation going, that is usually pretty scattershot when you’re first talking to someone and your conversations centering around what they’d like to do. There’s going to be a lot of talk about what their plan is, but then what they need to do, their plan, do they have. So if you can kind of drill down and get more granular on the plan related to the conversation, the topic at hand, you could kind dive deeper in every question. So what are you trying to accomplish? What will move your mandate forward? What are the specific initiatives that will move those objectives forward? And then that conversation partner ends up really starting to think through that granular aspect of the plan, no matter if it's selling their business or growing their business, or whatever that looks like. Share on X And a lot of times. Something that isn’t talked about that’s very hard to really nail down is the timing. There’s a lot of plans out there, but what does that timeline look like?  I just wanted to reflect on this because as an investment banker, I also come from an investment banking background, although I left the profession about 12 years ago, but what I really noticed was that those clients who didn’t have a mandate, you know, maybe they just felt burnt out. They just wanted the relief and they want to sell their business, or maybe they wanted the windfall that comes with it, but they didn’t know what to do with their lives afterwards. They didn’t have a mandate. They really struggled after selling their business. They struggled with meaning. They struggled with the new challenge of managing their money, which was uncomfortable for them. And they had FOMO, you know, they had, they missed their business, because  they couldn’t channel their energies. And now I can really relate to this idea of what’s the ultimate objective and then how are we gonna get there? That’s the plan. So if someone knows what their mandate is and what their plan is, what’s the next step?  Okay. And, I wanna just touch on what you said because it’s very important what you just said. You brought up the risk. In that plan along with timeline, which a lot of people have a general timeline, but as you get more granular then you say, well, what are the risks we’ll be facing? And our risks as advisors are a business owner that doesn’t really have a plan after they sell their business. That’s going to bring issues to them greater than they can possibly imagine. So what is the risk to us? What is the risk to them? So addressing risk in that plan bucket is always a really good idea. I’m glad you brought that up. Now that we've identified our mandate and we have a plan and we understand the plan, we've gotten more granular. Share on X Now we’re going to talk about the team, not starting off with who’s on your team, but what capabilities do you need? And then do you have those? And it’s funny when you lead with that question, you know, you get a lot of people talking about how great these key executives are, or how well positioned you are to hit growth. That is going to really skyrocket your trajectory. But the team capabilities often are not met. You have some great key players, but then there’s going to be capabilities that they’re like, yeah, I don’t have a solid sales team or process.  And ultimately, the team is important because any business is basically a group of people with a mission, you can have a software, but someone needs to develop that software and to troubleshoot it and promote it. So without people, it’s really hard to build a business. Maybe in the age of AI, it’s gonna be possible, but not yet. Right. So we got the team.  Another thing that I bring up, I like to bring up in conversations when we’re talking about team members a lot of times there’s promotions within the organization and the management, the owner, whoever is making these decisions, they don’t always ask the question, is this role good for the team member? And I think when you take a step back and you say, oh, you know, I think they would excel there, but is that good for them? And so when those questions are brought to the table, a different lens is able to be brought in. Okay. So there’s not just that one way view.  Can you give an example?  Sure. So if there’s a professional, and it seems like a natural progression for them to promote into a higher role that will manage team members, but personally, they’re in a position in their life where the additional responsibility isn’t timed right, but they have all the capabilities, they’re solid, they’re loyal, they are a huge part of that team. Promoting them might not be the best, the best decision for them. Yeah.  Yeah. I experienced this. I had a very young, talented executive who did really well, investment banking, and I started kind of side business and I promoted him to be the managing director. And I totally burned him out and he ended up leaving and that was a huge loss for us. And one more thing in that vein is the chemistry. You know, we all are so different. All everybody’s so different to find that, you know, is the chemistry right? And if it’s not right, that’s okay. It might just take some shuffling but to address that question, people like to push aside personalities and just say, well there, you know, this is the job at hand and we’re gonna get it done. And we’re all professionals. The truth is chemistry matters and Steve, you know, as well as I do, we don’t take clients on that one principle if the chemistry isn’t there. We are working in very intimate parts of operating businesses and very confidential aspects of a personal and professional life of a business owner. Share on X So if the chemistry is not there, we have to address that. And so I think bringing that question up in conversations around team, it at least opens the door to start thinking about that being a component that needs to be considered.  Yeah. Love it. Love it. Okay, so we have learned about the mandate, we have a plan, we have a team. So what else do we need to listen to?  Well, none of that means anything if you can’t execute. So you can have the best plan, you can have a solid team. You can, everybody could be rowing in the right direction and know and there’s alignment. But how that execution actually plays out is going to determine if it’s successful or not. And so if you’ve planned well, if the team is aligned, if all of this is set to take off and you’re ready to pull the trigger, let’s talk about that execution. So how are decisions going to be made? That’s one of the questions I love to talk about because that is something that can, I’d say an SOP, absolutely can be in place for how decisions are made, but then to go outside that standard operating procedure, have you given your management the knowledge that they should go outside of that, and establishing that ahead of time is going to give everybody independence. Know exactly when to call an audible and when it’s better to ask for forgiveness than permission. Getting to the right decisions at the right time. And you know that execution going hand in hand with managing complexity. You have to have a rhythm for that, you have to be able to look at your progress, look at what you’ve done, understand you need to pivot in this area, and so that execution can continue to improve and you’re not going to make the same mistakes twice if you have a plan in place. To understand how you’re executing, then you’re going to be better positioned to fix anything that’s off kilter or isn’t working at all. That rhythm usually comes in the form of a calendared regularly occurring meeting and you know, it's one thing, bolts from the blue where something comes up and you're going to need to address it. Share on X We all have those, but having a rhythm in place where not only you know what you need to talk about and what you need to review and monitor, but also having that rhythm that other people know what they’re expected to bring to the table and to be prepared to talk about and respond to.  Yeah, I mean, I agree that if you want to have good decisions, you need to harvest the ideas and engagement of your people. And you need a structure for this. It’s not gonna happen by default. You have to communicate that you are, you want their opinion so that they actually should bring it. And then you need to create space for it. And then you are gonna get, you’re gonna teach people to make decisions, and you’re gonna get better decisions by people who are closer to the action. It’s all very good. However, none of this matters without self-awareness. So how is self-awareness plays into this listening structure?  And I love this because all of those conversational, active listening topics that we’ve talked about, we’re here, Steve, you and I are business advisors, and we’re here to gather information so we can help them be better and help them accomplish something, growth, you know, whatever that might be. But there’s a personal aspect to active listening. When you know somebody, it’s easier to understand how they might present information because they believe a certain way or what’s important to them. So when you are working with someone that’s self-aware and understands everything about like if they’re risk adverse, then what they might project to you when you’re talking about risk is that there’s no way that could happen because they are so scared of taking any risk. You know that, well, no, I’m not going to believe that. I know that it might be able to happen. They’re just highly risk adverse, so being able to filter what you hear from a conversational partner and then understanding more about their personality and how they view things. And so some of the questions I might ask somebody I don’t know well, and I like to lead with these is, you know, what do you value? What’s important to you? What are your personal aspirations? And I just spoke to someone yesterday via Zoom that I hadn’t had the pleasure of meeting. Very interesting individual, very engaging. I don’t think anyone had asked him what his personal aspirations were outside of what he’s doing right this moment. And it was so interesting to hear him start talking about that. So that gave more depth to see how he’s going to color all of these other areas about his mandate and his plan and his team. But then to get to the, you know, the real understanding, personally, I know what he wants to aspire to do now and then if you’re able to, which I know you are, to see them interacting with their colleagues, you know. How does this person interact with other people? Are they bringing this happy go-lucky attitude? Are they always looking at the glass half full or half empty? Are they, you know, however that goes. It's all of these different little tidbits of information lead you to what is this person's self-awareness. And if you know that, then you'll be able to do better helping them. Share on X   Hopefully. Especially if they’re aware enough, if they have very low self awareness, it’s gonna be difficult to coach them. People are not coachable when they’re not self aware. Now, this is great. This is a great framework. So this is the power listening framework. And mandate, plan, team, execution and self-awareness. One thing that struck my ear, you mentioned that a risk aversion, so sometimes people are risk aversion. Risk averse. It is true, but also entrepreneurs are often poor in risk management. Sometimes they’re risk averse and then they don’t make decisions, but sometimes they are risk unaware, perhaps. And maybe it’s not intentional risk seeking, but risk unaware or not sufficiently careful, cautious. And they make bad decisions. Stupid decisions. Why do you think that in general, the risk management is not so much of a strength of entrepreneurs?  The entrepreneurial journey is up and down. It’s not for the faint of heart, and we attract people to build, grow, establish, build, and grow businesses that tend to take risks and they’re independent. They typically have certain advisors or someone in their network or a few people in their network that they lean on for advice and when their ideas can be confirmed, it’s pedal to the metal. We’re gonna grow this thing, nothing’s gonna stop us. That is what’s in their character to do so as entrepreneurs, experience those ups and downs, that I think is typically why we find so many willing to take risks. But if, you know, if you actually ask enough questions that can get to where those boundaries are, then you can advise from a much better position. Okay.  Yeah.  So this is fascinating. So you are about to start your work at this investment bank, W.G. Nielsen and Company.  Yes.  How are you going to approach your work? I mean, business development has changed so much over the past 15 years since I did it for my investment banking firm. And we used to be able to cold call people and send them your newsletters, printed newsletters, and they would actually read– it’s no longer the case or it’s much harder. So what do you see as being the best practice business development process in investor banking? If you can talk about this.  I’m happy to talk about it. And unlike you, I was in this space before, there were online data rooms. When we would share information with interested suitors, we would literally make Xerox copies and we’d put them in binders and we would FedEx them, and then we’d wait three days to follow up and make sure they had what they needed in the information we sent. So, you’re right, it has changed dramatically. And with all of the opportunities there is a very specific process, I think, regardless of the industry to approach them. And that’s, you know, if I can have an introduction through someone I know, obviously that’s the best. A nice warm introduction. Someone saying, ‘Hey, you need to make meet Alana, she knows what she’s talking about.’ Something like that would be ideal. But, you know, nine times out of 10 we don’t have that, that luxury. So, somehow getting in front of them, whether it be through a video clip and a podcast that has something that interests them, being on LinkedIn and posting something that adds value to a question they had, but we bring a very unique in the investment banking space, and especially the middle market and lower middle market. We bring a very unique skill to a very important problem. So my goal in business development in this day and age is to show our expertise in their space and to offer them an ear for them to ask questions. Share on X An avenue for them when there is something on their mind related to selling or buying a business, I wanna be the person they think of. So establishing a rapport that’s genuine because it is such a unique space, we genuinely do wanna help these business owners clarify their direction. We might not be the right firm. W.G. Nielsen is extremely diverse in the investment bankers that they have on their team. So whether it’s healthcare, telecommunications, industrial, we have the right person that will have the right answers, but getting that comfort with business owners who don’t need you right now. Those are the ones I wanna talk to. They might not need me today, but if I can share with them that you have a place to go, when you do have a question, call me and if I don’t have the answer, I will connect you to the person that does, and that strategic direction that that one little tidbit of value that they might get six months before they’re ready may be the reason they call us when they’re considering who to hire. Yeah. This is very, very insightful. So it’s basically building the trust and building the awareness top of mind awareness that you’re there to help them when they need help. And also, I mean, I think the trust piece is very important in this business. Yeah. I mean, what I experienced was that people were very reticent about sharing their plans because they didn’t want competitors to get wind of it, didn’t want their staff to know. So for them to be willing to even share that they are thinking about exiting required a high level of trust from the investment bankers that they talk to. So if you have a good process to build that trust and you have a good team that is trustworthy then it’s a good spot to be in. And that, you know, it speaks to that chemistry, again, it speaks to if there’s five different investment bankers, which there’s usually 10 or 15 investment bankers talking to the same people, the same attractive business owners that run operations that a buyer would be interested in. But not all of them really care and business owners are astute. They know when they’re trying to be bamboozled. They know when someone’s trying to sell them something. When you come to the table, honestly, offering help and honestly wanting to give them direction, whether it involves your firm formally engaging or not, they sense that, and that’s I think why some people are successful and some people aren’t. Do they really care? Do they really wanna help or are they trying to land a new client, which in our space there’s a lot of both.  Yeah. And that brings us full circle to your why– helping people and the servant,  leadership, why that is so important. So, Alana, if people would like to learn more about the Business Owner Success Alliance and potentially W.G. Nielsen, or you, they would just like to connect with you and maybe have a conversation or invite you to a podcast, where can they find you? Okay, well I’m on LinkedIn. You can search Alana Dobbins,  you’ll be able to find me A-L-A-N-A-D-O-B-B-I-N-S. We are, as I mentioned, we are accepting applications for pre-registration on BOSA, so you can go to bosuccess.com and give us your information. We’ll reach out once we receive it, and we’ll talk you through our projected timeline and if we think it’ll add value to what you’re doing. So looking forward to that. W.G. Nielsen is W-G-N-I-E-L-S-E-N.com.  I’m looking forward to just this next year. There’s been a lot of ups and downs in a lot of different spaces. So the M and A activity is, it’s a very busy space right now. A lot of deals are being done, and a lot of questions people have with tariffs and other things. Speak to a professional. Don’t try to figure it out on your own. We have answers. We can help guide you, and you don’t formally engage anybody, just to get advice on something like that. Reach out to people you respect, you know, or someone like us and we can help guide you.  Okay, well, I can vouch for you, Alana. You are a great person. I would trust you with advice. So when I want to start my company, which is not gonna happen the next five years, I’ll try to keep you in mind.  Thank you. Thank you.  So, yeah, thank you. Thank you for coming to the show, to sharing your wisdom about powerful listening about the Business Owner Success Alliance, for which I wish you success. Thank you.  And, those of you listening to this conversation, if you enjoyed and you found this informational make sure you follow us on YouTube and on LinkedIn and stay tuned because we’ll have an exciting entrepreneur or subject matter expert on the show every week. Thank you for  coming, Alana. Thank you, Steve. This is always so much fun to talk with you. Thank you again.  Thank you. And thank you for listening. Important Links: Alana’s LinkedIn Business Owner Success Alliance (BOSA) W.G. Nielsen & Co.