What The Most Successful Entrepreneurs Know & Do Differently With Kirk Dando

To find out what most successful entrepreneurs know and do differently, I sat down with Kirk Dando. Over the last 20 years, Kirk has helped more than 5,000 executives – including eight Ernst & Young Entrepreneurs of the Year and several “Best CEO” winners – kill it in business. In this interview, we cover what successful entrepreneurs think and do differently, so that you can begin to change your thoughts and actions. Enjoy!

Have comments, questions, ideas, or feedback? I want to hear it. Tweet me at william_griggs.


Topics Covered In This Episode

  • Can you tell us more about your clientele?
    • Why do CEO’s typically come to you?
    • What are you able to help them with?


  • You’ve spent a lot of time with successful entrepreneurs. I’d love to dig in briefly about things you think they do differently.
    • In your experience, what makes them different?
      • Is there a difference in how they think?
        • Mindset?
      • What about what motivates them?
        • Mercenary vs. Missionary?
        • Chip on their shoulder?
      • What do they do differently?
        • Problem Solving vs. Problem Predicting?


You cover all 12 in your book called Predictive Leadership, but I want to spend the rest of the interview going through a few of what you call the 12 “warning signs of success.”


  • A warning sign of success? What do mean? Don’t most people focus on warning signs of failure?
    • What’s the value of this approach?
    • Why don’t more people think this way?
  • 12 Warning Signs of Success
  1. Right Idea, Wrong Person
  2. Bad Management of Great Opportunities
  3. Open Door, Closed Mind
  4. The Leadership Bottleneck
  5. Hope Is Not a Strategy
  6. Core Values Meltdown
  7. Drinking the Chaos Kool-Aid
  8. Communication Vacuum (aka: It Sucks)
  9. Incentivizing Failure
  10. The False Security of Revenues
  11. Random Acts of Accountability
  12. Sowing the Seeds of Decay



Startup Slingshot Radio’s audio transcription is done by GMR Transcription

William Griggs: To find out what most successful entrepreneurs know and do differently, I sat down with Kirk Dando. Over the last 20 years, Kirk has helped more than 5,000 executives, including eight Ernst & Young Entrepreneur of the Year award winners and several Best CEO winners kill it in business. In this interview, we’ll cover what successful entrepreneurs think and do differently so that you can begin to change your thoughts and actions. Enjoy. Alright Kirk, thanks for joining us today.

Kirk Dando: Thank you William. I’m really excited to be on this with you. I have several friends that know you and that have been part of Startup Slingshot. And this is a great opportunity and I appreciate it.

William Griggs: Yeah, basically, those friends, Sam Decker, Brett Hurt, they all told me, in a way, they didn’t use this language, but they all told me I’d be an idiot not to have you on here. So I definitely appreciate your time and the audience appreciates your time. In our time together today, I want you to help the early stage entrepreneurs in our audience succeed in growing their businesses.

And to do this, you kinda have a superpower that’s unique from what a lot of the previous guests have had. And I want you to tap into that, your research, your experience as a coach, advisor, some really successful CEO’s across the nation. Really blow the minds of the audience so we can help them succeed in building their business.

Kirk Dando: Well, I’ll do my best.

William Griggs: Very cool. So can you tell us a little bit about your clientele? Maybe share some of the names that you work with on the CEO level.

Kirk Dando: So I work with the executives, predominantly CEO’s, but executives in organizations. I’ve worked with probably over six dozen entrepreneurs over the last 15-20 years. I’ve worked with eight to ten Ernst & Young Entrepreneurs of the Year, several CEO’s of the Year. I work really in a range of small to mid-market companies. Some that actually doesn’t sound small or mid-market, but Fortune 500 down to very small start-ups that are pre-revenue and are coming out of the ground.

William Griggs: Okay cool. That’s where our audience is today so like you said eight to ten Ernst & Young Entrepreneurs of the Year that sounds like a lot of the people in the audience are shooting for that as their business starts to grow. What do people, or what do executives or CEO’s typically come to you for help with?

Kirk Dando: Typically what they’ve realized is that, as the saying goes, change is inevitable, it’s going to happen, but growth is a choice. And what they found is that they made that choice to grow. And, typically, they’re either at some kind of strategic or organizational crossroads.

And they realize or they start to think, “Hey I don’t know what I don’t know,” or “We’re starting to grow to a point that we’ve not been before.” Or they’re very clear about, “Hey I know where I want to take the business, but I just feel like I might be missing something.” And, typically, what happens is they’re talking to another CEO that they’re friends with and my name gets brought up and we make the connection.

William Griggs: Got you. Very cool. So there a lot of people in this audience that are
either beginning to work on their business, they’re already working on their business, and like you said change is either happening to them now, or it’s about to happen to them. So in this episode let’s help them with that growth piece and kinda overcome some of the obstacles, and some of the hurdles that are right around the corner.

Or they’re facing right now. So, before we dig into some of those principles that you talked about in one of your books that you wrote, recently. You spent a lot of time with successful entrepreneurs. I think I’d be stupid not to ask if you saw any themes or trends that maybe they set them apart from other entrepreneurs.

Kirk Dando: I think that one of the things that sets them apart is often times the thread that I see weaved through that’s very common is they just got that entrepreneurial itch or that leadership itch at an early age. And they were either put in a position where they had to organize something or whatever the case may be. And they just realized that they got the bug and they just couldn’t get rid of it.

And along the way, as they started kinda growing in their career and in their influence. They started their ability to get other people to rally around an idea or a thought, or a concept. And get them to follow that. And so that’s a fairly common theme and from there it kinda grows and blossoms into they want to make a difference. They want to change something. They want to create personal wealth and financial freedom, whatever it may be. But, typically, that the seed is just that itch that they have to scratch at some point.

William Griggs: Got you. Very interesting and yes that definitely sounds like it fits a lot of the people in the audience. As far as the next piece, which is around the growth piece. Is that something that you think differentiates a lot of the experienced entrepreneurs that you work with as compared to maybe less experienced? Or people that are – have been less successful to date in their career?

Kirk Dando: The growth piece is absolutely a critical part of it. That’s what I love about your mission there at Startup Slingshot and what you’re doing. The reality of it is that if you’re gonna grow something it’s gonna take leadership to do it. And it’s gonna take an entrepreneur who’s got that mindset. And just like anything there’s entrepreneurs and executives who are excellent and there’s ones that are struggling and trying to figure it out still. But in that growth mentality of having a healthy dose of paranoia about can I do this and will we do this.

And a healthy amount of confidence to say the difference between thinking, “Can I do this? And how can I do this?” That’s a mindset. It’s a very subtle, but significant mindset difference between “can I,” which is a kind of a little bit wondering and worrying and anxiety versus “how can I do this,” which is a sense of curiosity and I’m gonna figure this out in a path that may not be straight, but I’m gonna always keep leaning in. And I’m going to surround myself with wise, intelligent people that have been there and done that. And whatever it takes I’m gonna get there.

William Griggs: That’s interesting. Like you talked about the growth mentality, thinking about how can I do this. And that’s obviously something that’s in our audience today. That’s why they’re listening. So let’s start to dig in. You talk a little bit about in your book the difference between problem solving and problem predicting. And how that kind of ties into this whole growth theme that we’re discussing. Can you talk a little bit about that?

Kirk Dando: You bet. It almost sounds like a fun play on words, but as you kinda peel back the layers and start to understand it. One of the mentalities of the leaders and executives I work with, it’s a once again subtle, but significant difference. They have a way of thinking about things. Problem solving makes companies work, but problem predicting allows them to grow. So you think about it there’s been thousands and thousands of companies for years and years. And we can exploit the historical transactional data to see what does and doesn’t work.

And as a startup organization, you’re predominantly focused and need to be focused on developing a product or service, raising the money you need, and surrounding yourself with a handful of people that can help you start to bring those dreams to fruition. But as you really start to grow that business and you start to get success and you start to have some of those sales, what you start to see is that single-mindedness and that focus that allowed us to grow actually starts to cause some problems, or what I call warning signs of success.

And if we’re not – if we don’t have that shift and that mentality between problem solving versus problem predicting and seeing the things that are coming, we actually start to get to where the business actually grows itself into so many problems. There’s a saying out there, “Nothing kills faster than success.” And we actually start to build this muscle set of problem solving. And rewarding the people that are the best at problem solving versus being able to see things ahead that for thousands of companies have already solved these problems. We need to shift that mentality.

William Griggs: That’s interesting. So you talked about looking at the data seeing that there’s a common path right. So once a company reaches a certain amount of success there is a warning sign of success is something that you talk about in your book, “Predictive Leadership.” So you look at the data, you can start predicting the problems as opposed to just reacting to them and trying to solve them as they come. It’s that shift in mentality today that we’re trying to drive home today for the early stage entrepreneurs in the crowd.

You cover about 12 of these warning signs of success in your book, but I want to spend the rest of the interview kinda going through a few of them. Right, can we – we don’t have enough time to go through all 12. People want to check out more, they can go grab the book. But as far as going through some of these warning signs of success, can you first just start with – you touched a little bit on it, but can you tell a little bit more, talk a little bit more about the warning signs of success? Most people think about the warning signs of failure.

Kirk Dando: Yeah, absolutely. Like I said in an early stage business we’re focused on developing a product or service and raising the money that we need to. But one of the issues that happens in growth – these 12 issues are the most common issues that I’ve seen over the last, like I said, 20 years. In dealing with thousands and thousands of executives and organizations, these are the 12 most common issues that as we grow interestingly enough are always a result of success.

And so for instance, we’re gonna talk about a couple of them. One is right idea wrong person. As we grow a business and we’re starting to hire and promote people, we get it right about a 1/3 of the time. About a 1/3 time it’s okay. And about 1/3 time, it’s just really not very good at all. And there’s really no other area in business where we would really tolerate such poor results as we do in the hiring and promoting of people.

Well, what do we need to do early on? What muscles do we need to start building to make sure that we don’t just have the right idea? We have the good processes. We have the good interviewing. We test and we do all this stuff, but how do we make sure we get the right idea and the right person?

William Griggs: Got you. Very interesting. So you talked about that as the right idea, wrong person. Thinking about these issues as people at home are trying to wrap their head around this. So thinking about this as once they have some success, these are some of the problems, these are some of the issues that result from that success. Right?

So you wouldn’t be necessarily promoting people hiring additional people if you didn’t have some success under your belt. So the next step like you talked about right idea, wrong person. How do you rectify that and how do you look forward, or look ahead to that moment? So what is kind of a solution for the warning sign of right idea, wrong person?

Kirk Dando: So part of it is, is just having a mindset and understanding that as an organization grows and this is, once again, it’s very subtle. As an organization grows and we’re all focused on the goals, often times we bring people along that are critical in that success. But as they’re focusing on helping the business grow, they kinda stop growing themselves and their capabilities. And we’ve seen this before where organizations grow and then it just kinda outgrows somebody’s abilities or experiences.

And so often times we say, well we need to put in a process that’s going to be great for hiring or whatever. But sometimes it’s just a mentality and having a conversation with people early on. And saying, “Hey, just because a business is 2X today, doesn’t mean we have the people that can run it at 5X. So what is gonna take for us to not just grow the business, but grow ourselves?” So the very people that helped us get here and be successful, we don’t end up with this emotional issue in the future. Having to talk to people and let them go that they can’t help us go forward.

And that’s often times that’s where people don’t have those conversations early and often. And then when they – when they’re upon them, they do all these kinda workarounds and they don’t deal with it. So the solution, there’s not a single solution, but a big part of it is just having a reality check. That, “Hey this has been happening for a long, long time. What do we do to pressure test our team?” To really review them. To really have the hard conversations and the accountability about what does it take for you to grow because I want you to be here. I want you to be a part of the success, but you have a role in that journey.

William Griggs: Right. So you talked a little bit about that reality check. The making sure in the mindset there’s an understanding that this is up and coming. This is going to be a problem. And definitely you can see the downside. The emotional impact that that could have if you have to let somebody that was crucial to the early success of the company go. Or not able to promote them. Internally, do people think – or is it about setting the expectation that this is on the employee to continue to grow and get more experience? Or is this something that companies can build internally as far as processes, to make sure that they basically continue to track the way you want them to?

Kirk Dando: William, that’s a great question. It’s really, the answer is both. However, I do see a lot of times where organizations will set up and say, “Hey, we’re gonna have this kinda training and you need to get involved.” An unattended consequences is what they’re saying. They’re saying, “As an organization, it’s our responsibility. We’ll help you grow.” And I’ve not seen where that works. I’ve seen where great processes and systems, and training inside of an organization are helpful. But, ultimately, you said what’s the mindset of people that want to grow is they stay very, very curious. And they take it upon themselves to really grow in their role and grow in their responsibility. And to reach out and get mentors and things like that
outside of that to have their own kinda personal board. So they can grow with the organization as the organization grows. Because there’s never – it just doesn’t happen where an organization grows at the same pace as someone’s abilities. And it’s, again, it’s not intuitively obvious. These are things that are happening because we are successful. And you use the word expectations.

Setting those expectations early, not just around this, but other things. Often times when these things happen is when you start seeing doors close, people having back channel conversations as if something has gone wrong. And the reality of it is you only get to experience these kind of things, even though they’re not fun, you only get to experience them if you’re successful.

William Griggs: Right. It seems like some startups try to set that expectation around growth in a way of maybe an education fund. Right. They give you a certain amount of money, but they’re not actually doing the work to make you trained. It’s just greasing the wheel so that person that is super motivated or super interested in continuing to grow can do that.

Kirk Dando: Yes.

William Griggs: Very interesting. So let’s transition to that next piece, the number two in your, “12 Warning Signs of Success,” which is “Bad Management of Great Opportunities.” What do you mean by that?

Kirk Dando: So as an organization grows, often times teams grow up around the people, the ones that are doing the work. And we don’t truly understand what management means. Used to be everybody wanted to be a great manager. Now everybody wants to be a great leader. And there’s not a great definition of it. So I see a lot of times where people are managing teams and managing projects, but they really don’t have the skillset.

We’ve not really done anything to really define what great managing looks like. And we’ve not really done a great job of helping them get the skills. And so you often times see where a great technician gets promoted into a manager. And then they start to fail pretty quickly. So what happens is we’ve got these great opportunities. We’re starting to scale. We’re starting to acquire customers the way that we want to.
We’re starting to really do and compete in a way that we set out to do. And then it just starts to grind a little bit. We can’t quite figure out what it is. And the reality of it is, is these are one of the issues that growth and success causes. We’ve got to now start to really be purposeful about developing, not just saying what management is, but actually developing those people that have those capabilities into being managers.

One of the toughest transitions in anybody’s career is to go from doing to managing. And it always gets underestimated how hard that transition is. Especially, in a fast startup growth environment. We way underestimate it. And then what happens is we’ve got these incredible opportunities and we just manage it very poorly.

William Griggs: Got you. So you’re talking a little bit the company’s going well. You’re scaling the team. You’re taking an A player. You’re making him a manager. But without kinda coming around them and supporting them, they’re not destined for failure, but a higher likelihood of failing at that role. And taking what was a great opportunity, like you said, everything is moving up and to the right. There’s growth. You’re adding more people to the team. Obviously creating more value, hopefully. And then you talked a little bit about lack of support. How do you manage, or how do you advise people that you work with to kinda provide that support?

Kirk Dando: So being very intentional about the – not just the measurable outcomes, but sometimes it’s just the soft side of things. How do we want to develop a team? What are the expected outcomes that we’re trying to drive for as an organization, and as you as an individual? And, literally, having a plan and helping coach and develop somebody into those roles. Change comes at a cost. It always costs us something.

And when things keep going up and to the right. And we’re on a 90 day cycle and we’ve got external commitments to investors and things like that. We’re telling them how things are gonna go. Often times, it’s not intuitively obvious. We’ve got to let things get a little bit worse before they can get better. And that is very true when we’re trying to develop a manager.

Sometimes we have to slow down in order to cause them to speed up. Something in a startup environment that is very counterintuitive and very, very difficult to do. But the ones that make it through either develop those people. Or what ends up happening like we said, they end up replacing them. And find somebody that’s been developed somewhere else.

William Griggs: And as far as developing them, is that the responsibility of their direct superior? Is that someone in HR? How do you think through that?

Kirk Dando: It’s so – in a real small environment you may not even a HR. So, ultimately, the first person that’s responsible is the person that’s needing to grow. They’ve got to have that desire. And like I said, it’s one of the toughest transitions is going from doing to managing. And if you don’t really, really want it and understand what you’re getting ready to step into, no amount of help from your leader, or from HR or anything else is going to make the difference. There’s so many tools. There’s so much written about these things. It’s not because there’s a lack of content. It’s most times because there’s a lack of desire.

William Griggs: So part of that it sounds like is having a frank conversation with you’re A player about do they want to become a manager. Not just forcing it upon them.

Kirk Dando: Exactly. And there’s, and as you know and as discussed, there’s volumes written about this too. You’ve got to have an environment where A players can play and be successful. And not everybody has to be on a singular path up through manager and leader. That’s absolutely not necessary. It doesn’t work. It never has worked.

But often times, that’s what we’re signaling either indirectly or directly. But we’ve got to have an environment where people can perform. We all have gifts. We all have limitations. Often times, I see where people trying to put in, but got intentionally left out. We’ve got to play to our strengths.

William Griggs: So we talked about the second piece, which is bad management of great opportunities. Is there anything else we need to cover in that section before we go to the third one?

Kirk Dando: No. I think that’s good.

William Griggs: Very cool. So the third early warning sign of success is “Open Door, Closed Mind.” Can you dig in a little bit about that?

Kirk Dando: Often times as leaders, we – like I said, changes will cost us something. And as leaders, we don’t want it to cost us anything, the morale, the culture, or any of those kinda things. So what we do is we start talking about, “Hey, we’ve got this open mind mentality, open door mentality. We want your ideas. We want to hear from you. We want to hear about the problems and the issues you’re having. We want you to shift to predicting these things.” It’s open.

And then somebody brings some things that they’re seeing and all of a sudden, they’re kinda singled out as, “Hey they’re part of the bad egg network, or they’re always complaining.” Or, “Hey, just kinda do these things and quit doing this.” So what you do is you create this environment of, “Hey, we’ve got this open door.” But the real environment is, “Hey, we’ve really got a closed mind. We really don’t want to hear this.

We don’t really want your feedback. We don’t really want to hear about the problems and issues.” And so what you do is you create this underground kinda discussion pool where everybody’s backchanneling and having where the real conversations are happening. And often times as I go into organizations, I’ll spend time doing some confidential one on one conversations with people and get introduced into that kinda underground conversations.

And there’s some wonderful things. And there’s a lot of times where the issues that are gonna unlock the, not only the leadership, but unlock the business are happening there. And we just haven’t really figured out how to navigate an environment where it doesn’t just become, “Hey bring us all your complaints.” But it’s also how do we really get the best thinking of the best people out there.

William Griggs: Yeah so in that case is it really about – continue to have – is it about a leadership issue of they feel like they have to talk about having an open door policy, but they don’t really care. Or is it more that they haven’t set the expectations with the employees that you can come to me with problems, but also solutions? Or how are you thinking about that?

Kirk Dando: Very good point. It’s bring the solutions as well. And it’s just an authenticity. Often times once again in a startup environment, we’re doing three or four different roles. Things are going quick. We’re trying to get out and plan, but often times the day gets away. And so when people come to us, we just don’t make the time to really sit and listen in an authentic way. And like you said coaching them saying, “Hey that’s great, but you need to bring the solution.” Or, “How would you resolve that?” Or doing those kinda things. And sometimes it’s just an issue of having the time to slow down and have the right conversation.

This is not some very highly technical difficult thing that needs a big process overlay on it. Sometimes it’s just being in the moment and being able to listen. A lot of these 12 warning signs of success are overly obvious. They’re embarrassingly simple and that’s part of the issue is we tend to overlook them. We tend to give in to what we see as chaos. And we start to say stuff like, “Well, gosh, people are always going to be this way.” Or, “The market’s like this.”

And once we give in, almost in an instant we give up. And I’m here to kinda tell you that chaos can be corralled. It’s just you’ve got to be kinda on your toes thinking about shifting from developing a product and service, which now you should hopefully have a team to – really issues of growth and success, which is a different set of muscles.

William Griggs: As far as the open door policy and the CEO’s in the audience having this, how does it turn to kinda that backchannel chat that you talked about. Is it the person that has the open door policy isn’t really receptive or they’re not reflecting back what they hear? There’s no action based on what’s being brought to them. What is the transition? What causes the transition to that backchannel talk?

Kirk Dando: So you asked me earlier on about a mentality of the really successful entrepreneurs and executives. They have a level of humility. And your point – you brought it up. If somebody’s bringing you something and there’s no action and sometimes that – the action can be no action. You’ve got the explicit action, give them the why. Why is this happening? But to just continuously be – kind of being an order taker on hearing things we can do to improve and problems, whatever the case may be.

And not taking action, or just not really even giving it the time of day. What ends up happening is, is people are going to start expressing – because people don’t want to feel like they’re crazy, or that they’re seeing something incorrectly. So they’re going bring it up with a peer. They’re going to bring it up with somebody else. And, unfortunately, there are some people in this world that get energy out of that. And so what they – they’ll find the people that’ll listen and all of a sudden they’ve sparked this campaign. That’s an unhealthy way. There’s some people that are not like that. That have a very healthy and good intentions. And so then they, they go about trying to create change in a kind of a subverse way.

William Griggs: Very interesting. As far as a solution around this, you talked a little bit about it being hectic in the startup land. We all know that. All the audience members can relate to that. Is this something where a CEO as the first step sets up office hours, makes time to listen? And obviously listens through this podcast and understands how to reflect back what they’re saying. How to answer the questions, maybe act on it. That type of stuff?

Kirk Dando: Yeah. And it’s not just the CEO’s. It’s the other executives. And I’ve had a lot of CEO’s and executives that have done that. Have said, “Hey, I’m gonna set up office hours.” And then they report back to me, they go, “No one came by.” And it’s because no one had an issue, or had anything during that time. Or it was so burning. And so part of it is just being available with those office hours. But it’s also just as age old as walking around, being curious, asking questions.

Finding out where people are at. What are they wrestling with? What are they struggling with? Sometimes people will give you the symptoms, but they can’t really give you the root cause. Because either they don’t have the context. They’re not swimming across all the lanes of the organization. So as executives, we have to stay curious and always be on point to be connecting those dots. And then also feeding back to people.

One thing is if you wanna encourage feedback, and good healthy feedback is when you get it and then we take action on it, is share that. “Hey, we got this information from so and so. And we saw patterns of it over here and here and here. Because you guys did that here’s what the solution was.” You got to connect the dots back for them.

You got to complete the loop so if you wanna build that muscle. You get what you reward. And if you on reward what people are continuously thinking about how to grow and make things better. But understanding that we can’t metabolize every single idea that comes down the pipe. Then you’ve got to create that environment and be very explicit about it and discuss it.

William Griggs: Yeah management walk – by walking around, asking questions, staying up to date on what they’re working on. Like, you said kinda going out of your way. Not just having the one on one time available, but then it also sounds like a little bit, like you said, not just the CEO, but also the direct superior. So it seems like office hours for the CEO is one thing. One on ones with direct superiors is another way to kinda do this.

Then you have to, like you said, connect the dots between what you did – or the feedback that you received and what you actually did. So, actually, I had a funny example. I recently met with a startup CEO here in town and he said in one of their surveys. They do kinda either a monthly or quarterly kind of a culture survey. And one of their developers had written after they asked a question, “What do you want to see more of?” And one of the developers as a joke just to see if it was written said, “More goats.”

And so then the office manager plotted on how they could get a goat to their next off-site. And they brought a goat to the next off-site. So now it’s a huge joke around their business. Again showing that they listened. Showing that they had a sense of humor. Showing that they cared. Right. Going above and beyond.

Kirk Dando: Yep. That’s an awesome example. Yep. That’s exactly right. And sometimes it’s just very practical. Like, I said overtly obvious and embarrassingly simple. I’ll have somebody just write out a little sticky note and put it on their screen, “Go find somebody doing something right.” “Go connect the dots on what’s working.” And it’s just being very intentional about doing these things. The good news is it’s not hard. But because it’s not hard and sometimes it doesn’t feel like super creative work, it gets pushed to the backburner. And then it becomes an issue.

William Griggs: As far as – we talked – the questions that I’ve oriented around so far are really around preventing it. Are the solutions for preventing it the same as the solutions for actually fixing it once you have all these backchannel chats?

Kirk Dando: So ask the question a different way. I’m not sure I fully understood the question.

William Griggs: So one of the – basically, I was focusing early on like how do we prevent the backchannel chats from happening? How do we make sure that people are heard? We talked about management by walking around asking questions one on ones with superiors, office hours. But say that if we’ve already gone too far. Now there’s all this backchannel chat. People don’t feel like they can come to the heads of the organizations. They feel like when they do come, they’re not heard. Are there other solutions besides the ones that are around preventing this backchannel chat that we need to talk about? Or is it the same solution that you would use to prevent it as you would use to kinda fix it once it does happen?

Kirk Dando: Yes, there are and I’m not shamelessly promoting the book. I’m just telling you like in the book I write about, “Here’s know this.” Meaning know this so you can recognize it. “Feel this.” This is what you’re experiencing. And, “Do this.” Meaning here are some very specific, practical, very easy to apply solutions. But yes. And I’ve been in a number of environments where it has gotten out of hand.

And what needs to happen is, typically, there’s a breakdown in trust and authenticity. Not just listening and walking around. And so what you need to do is to sit down and just be very explicit about those behaviors. We talk about do entrepreneurs think differently. Everybody thinks differently, but they really behave differently. And so in that instance, if it’s already – if that backchannel’s already starting to take hold.

It’s a matter of sitting down and once again just calling the game. Saying what’s happened. If you need to apologize for a breakdown in trust. And sometimes there’s a perception of breakdown in trust. As leaders, we can’t always share everything that’s happening inside of the organization. It’d kinda be like me sharing with my kids when they’re four and five years old everything about life and about intimacy. And everything else like that. It would just be overwhelming. And they couldn’t take contextually, couldn’t take it all in.

So in a business environment sometimes, we’re not able to share all that’s going on because we don’t even have all the data yet to make a full sharing. So it can give the perception of a breakdown in trust. But even having that conversation. People can see authenticity. They can see transparency. They can see somebody’s heart and what they’re trying to do. And they can also see manipulation. So if that’s been happening, just call it out and then make the choice.

William Griggs: Very cool. So that’s definitely some good advice for the listeners at home. Let’s transition to that fourth early warning sign of success, which is the leadership bottleneck.

Kirk Dando: So this is one that is very prevalent in very successful high growth organizations. In its simplest form, the way to recognize it is by looking at the org structure. And Tom Meredith, who is there in Austin, and I’ve spoken about this quite a bit, but org structure drives behavior. And often times as I go into an organization, I go into an organization, I’ll have everybody draw the org structure the way it’s functioning.

Not maybe the one that’s published, but the way it’s really functioning. And no one ever draws it this way, but if you could imagine having one box there at the top and that’s the CEO. And then having a single line coming down. And then a horizontal line with a bunch of lines going into it.

Kinda looks like a rake, what I call a rake organization. And if you think about it that leader is typically, they’re either very technically oriented. They’re technical geniuses and they’re just exceptional and that’s their comfort zone. Or they’re really great at building market and selling. They can kinda sell used Kleenex. But they’re typically not really effective great managers, developing people internally and developing them into their next role. Well that rake organization really makes them start playing to their limitations, which is developing and managing people.

And often times as I draw this, I’ve drawn it for small startups and I’ve drawn for Fortune 100 organizations, I’ll have the leaders say, “Well, we get it.” And then what they’ll do is they’ll move somebody in between them and the rest of the rake. And no one is sure what that person’s supposed to do. That person’s never really done it. And it just kinda starts to come in and creates what I call that “leadership bottleneck.” It’s not a bottleneck in the sense that we need to develop more leaders.

Often times it’s just we need to be able to as a leader whether it be over a department or part of the organization. Or the leader of the organization, the CEO. Like I said, change costs something and often times as we need to mature into our next role, we hold on too tightly to the things that made us successful. And we really don’t want to exercise those muscles to grow and we create a leadership bottleneck.

William Griggs: So the leadership bottleneck is around leaders that are doing this because it’s maybe easier for them to do this route. Or at least initially easier than to kinda get out of their comfort zone.

Kirk Dando: Yes. Yeah, and as the organization grows so quickly what they do is they have one on ones with people and they start setting up these structures. But really if you play the video what happens is the path of least resistance is always back to their office. What you said earlier, often times people are bringing problems, but not necessarily solutions.

So it becomes kinda the problem solving hour versus how am I going to develop and mature these muscles and these people so they can start to do these things as I would do them, or as we need to do them for the organization to grow. And all of sudden you look up and you’ve got a rake organization.

William Griggs: And is the solution to really just build up those functional leaders so they can handle their function?

Kirk Dando: The solution is, is to really design the org structure that you need for your next one or two levels of growth. And not put names in the boxes and get very, and get very clear about what is needed in those roles. So it’s not just tactically what do we need, but one year from now if that person was wildly successful. Let’s say we don’t have a CFO today. What one year from now, what is it that we need them to be wildly successful? How do we expect them to do this? That sounds like an odd question, but I’ve had in organizations where they’re hiring their head of product and they went through an interviewing process and they got the person in.

And this was an organization that really needed a strong product development. They had kinda stalled out as an organization. So this person going through the interviewing process up, they were supposed to ride in on a white horse and save the day. Well, if this person would have come in with that kind of attitude, they would have alienated everybody right away. And you say, “Well, that’s kinda obvious.” Well it’s not so obvious and it happens often times. So we had to kinda stop and say, “Hey we need to explain to this person how they need to come in is they need to come in and win the hearts and minds of people. They need to understand what is and isn’t working. They need to come in and talk about what is working and then they need to create the influence to come in and cause the change that’s needed. So part of that role is how you do it. So having that box be empty saying, “What do we need tactically? One year from now if they’re wildly successful, how do we expect them to go about doing this?” 90 days from now if they’ve done their job what does it look like?

And you define that role and then you start weaving names back to it and you start to see where there’s a gap. Then you start to close that gap with that person. Often times we just start trying to close this perceived gap. But taking three, four hours and really defining a role. It’s just things often times we don’t do and designing and org structure for what that needs to be.

And then we start communicating that to them and saying here’s what – here’s where we’re going. And here’s how we need to feel those boxes. So once again it goes back to our earlier conversation. If people are very aware of what they need to do personally to get to that if they’re not there. And we’re aware so we can come alongside them and support them.

William Griggs: Got you. That makes a lot of sense. Instead of just jumping to conclusions and jumping in and saying, “Hey, we got this functional leader here let’s move him into this box. Take the time. Think through actually what you need to succeed form that person. Identify if that person that you do have on staff is the right fit or not. And what are they missing to help get them to exceed your expectations and really help the business grow from there.

Kirk Dando: Yes.

William Griggs: Very cool. So we’ve definitely covered a lot in this interview, but there’s a lot more to cover in the book. Can you talk a little bit more about what’s in the book that we haven’t covered?

Kirk Dando: So one of the things that I talk about in the book is just the journey of growth itself. And I go deeper into this subtle, but significant difference between problem solving and problem predicting. And not just what it is, but to really have to build a problem predicting culture into the organization. I use the analogy of climbing Mt. Everest. How to prepare people? If we just prepare people to get to basecamp, but we don’t really prepare them how to get to the summit. Often times, for instance, climbing Mt. Everest when you get 28 – 29,000 feet, you have to put oxygen on. Well, if I didn’t tell you that we were gonna have to do that and you trusted me and thought that I had been up the mountain a bunch. When we got to 28 or 29,000 feet, you’d start to freak out and go, “Why is this person – why am I following this person?”

You’d start to worry about getting off the mountain alive versus getting to the top, which was the goal. Versus if I started off at the bottom and said, “Hey when we get to 28 or 29,000 feet, we’re going to be carrying these oxygen bottles that are going to be heavy. They’re going to be a pain, but you’re going to be happy.

And in fact we’re gonna stop and we’re gonna pop a cork and we’re gonna have some champagne because only about ten percent of people actually get to that level on the mountain. So when we got there, you’d actually be looking for it. You’d be anticipating it. And when it hits and it’s hard, you’d be excited and you’d stay focused on the goal because you know we’re closer to the goal. Well suddenly in business often times when we have the right idea or wrong person, or we have a leadership bottleneck, or whatever, we start to see where everybody kinda loses hope.

Well, these are conversations that we can have early on. So I spend a lot of time in the book helping executives understand how to have those conversations. What do they look like? How do you prepare and mange expectations that growth and success brings? And then I go through each one of the warning signs in a very practical, in a very deep way like I said talking about “know this, feel this, do this.”

And it’s written more as like a field guide so people can kinda go back and use it as – with their teams and individuals. I’ve been very fortunate to travel out of the country. And it’s always very humbling to me when someone walks into an interview with my book and they’ve got it dog-eared and tagged and everything else like that. And that’s not about me. What it says is about is it’s just a good compilation of real practical experiences and it’s not a lot of theory. It is advice that you can apply.

William Griggs: Right. It’s definitely a different book. Not a lot of books out there on the market. And it definitely applies very much so to the audience of early stage founders like you said it’s that reference guide, it’s that practical guide. It’s all about helping those early stage founders whether that’s the first time or second time, always prepare for and predict for what’s coming next and how they can best prepare themselves and their organization for that next step. If people want to learn more about you, find the book, learn more about your company, how can they do that?

Kirk Dando: Well, the book is on Amazon. So it’s called “Predictive Leadership.” And so it’s easy to find there. It’s on Kindle, wherever, and in bookstores. If they want to reach me, website is dandoadvisors.com. You can also email me straight. I’m really good, I’m like you William in the since that I think you and I are very kindred spirits and want to help make a difference in the lives of those that are wanting to grow. And so email is a great way to get a hold of me, which is just kirk at dandoadvisors.com

William Griggs: Very cool. I’ll put the URL to your website and the Amazon links in the show notes below the video. Kirk this has been a great interview. And definitely appreciate your time. Thanks for coming on the show today.

Kirk Dando: Thank you William. It’s a pleasure and I meant what I said at the beginning, this is very much of an honor. I appreciate it.

William Griggs: Thanks again.


Kirk Dando’s Bio

kirk_dando_potraitKirk Dando is a highly sought-after and well-respected leadership and growth expert whom executive clients call “The Company Whisperer.”

Business leaders find a “friend in the foxhole” with Kirk; he helped scale and sell a billion-dollar company. As a C-level executive, he walked the lonely road of leadership and worried himself to distraction, but learned a lot. For more than 20 years, he has worked with more than 5,000 executives – including eight Ernst & Young Entrepreneurs of the Year and several “Best CEO” winners – overcome common business pitfalls to unlock explosive growth.

His bestselling book, “Predictive Leadership: Avoiding the 12 Most Common Mistakes that Derail Growth-Hungry Companies,” shows execs how to predict and prepare for the most common business pitfalls. It helps eradicate their fears and doubts that make it “lonely at the top.” Kirk has a stunning track record of causing breakthrough growth for companies that face problems stemming from their own success.

As seen on Fox Business and Bloomberg Television, audiences relate to his real-world stories and his high-energy, no-nonsense style as he demonstrates how leaders can predict problems before they show up in the results.

You won’t find another leadership expert like Kirk. He combines the raw emotion felt by leaders with the real-world action needed to achieve and sustain success. Forget complicated theories and bogus acronyms; Kirk gets to the heart of the matter to help leaders create real change in the lives of their employees, shareholders and themselves.


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About William Griggs

William Griggs

William Griggs is a product and customer acquisition strategist who has helped numerous startups including companies backed by Andreessen Horowitz, FLOODGATE, & 500 Startups. In addition to his consulting work, he has written for Mashable, VentureBeat, & ReadWrite. You can check out his podcast on iTunes (The Startup Slingshot TV) or follow him on Twitter @william_griggs for Tweets chock-full of delicious knowledge nuggets.

In addition to everything tech startups, William loves breakfast tacos, dogs, short emails, and Amazon Prime. He currently resides in Austin, Texas with his beautiful wife Elizabeth.

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