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Episode #229
Stuart Leo

From 7 Figure Consulting Business To Software CEO

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Making the transition from a 7-figure consulting business to software CEO seems like a difficult pivot. This is one pivot that Stuart Leo has made with great success. In this episode, Michael Zipursky and Stuart, the CEO of, discuss business pivots and evolution. Stuart looks back at the roots of his consulting business, what he learned from it, and how these lessons help his current software business. Tune in for more great learnings from Michael and Stuart as they explore insights from a business consultant.

I’m very excited to have Stuart Leo join us. Welcome.

It’s a pleasure to be here. Thank you for having me on the show.

I’m glad to have you on. For those who are not familiar with you and your work, you are an entrepreneur, the Founder, you have a podcast and also the CEO of, an intelligent business management platform that helps leaders get more done. You have fifteen years of experience in consulting, leadership management and strategy. I want to get into how consultants can be able to manage and exceed their goals for 2022 and beyond. Before we do that, let’s go back in time and give us a glimpse into the early stages of your career. What did you study and then what was your first venture into the world of work or business?

I’m old enough to say that that’s going back to the last century, which sounds extraordinarily scary in the 21st century. I started off studying a double degree in Hotel Management and Business Commerce. I loved to travel, adventure, hotels and imagined myself running some boutique, exclusive hotel on the Swiss Alps somewhere and in life.

As life took me on a journey, I realized that I valued my holidays and I steered away from working in the hospitality industry to enjoying the hospitality industry. That meant I doubled down and focused on my business degree. I ended up doing a Commerce degree. I studied Commerce, majoring in Marketing. I ended up graduating in 1999.

My actual first job post-university was a tiny little startup I did with a mate at university. There was a little bit of entrepreneurialism back in the blood way back then. He was an IT student at the same university. I was Business and Marketing and we got together and we started a tiny little startup in the very first dot-com boom back in 1999.

It was a small site. We were the innovative little business model at the time where we sold advertising space for job ads to hospitals. Hospitals needed to recruit nurses, staff and whatever. We came up with a clever little subscription model that said, “Based on the number of beds you have in the hospital, this is your rate per year.” Now you can go ahead and place as many job ads as you like.

When I think back on it, it was far more innovative and interesting than I gave it credit for at the time and we did that for about a year until that first dot-com bubble burst. I don’t know if you can remember back in time to when that happened. The dot-com was like what Bitcoin is now. It was that new thing that money was flowing to. We were a tiny little business. Two boys on the beach in their parent’s attics and garages, trying to do a tiny little startup. It was as basic as you can imagine.

You can build a wonderful career working for yourself or build a wonderful career working for others. There's no right or wrong, but there are better fits for individuals. Click To Tweet

The bottom fell out of that market and we got to the point after about twelve months, which was a great learning experience, taking on some investments and running this thing and see where we go or do we go and get some real jobs and figure out how to do this thing called work. That’s not a bad question to ask because we said, “Let’s go get real jobs.”

Strangely enough, when we walked into our first jobs, we did not go through the traditional job interviews or anything like that. We walked into somebody going, “You should meet the CEO of this because they are looking for people like you.” Before I knew it, I was in a job in an agency in Brisbane, it was then the New Media Agency and working on digital strategies for companies at the bottom of this food chain but in the game. I did that for a few years before I ended up in corporate life. I could stop there but, in fact, it will stop there because you may want to join some other areas.

It sounds like you went from university to a year or so running your own small startup then got into corporate life. After a while, you decided that you wanted to start your own consulting-related business, which was Business Transformation. Talk me through a little bit of why did you decide to leave corporate life after being in it for a period of time? Why not continue climbing the ladder and moving higher up in the ranks and have that corporate career? Why did you decide to go off and start your own business again?

It’s a good question because corporate life is wonderful. I had a great experience in corporate life. I worked for a great company, a multinational. We got to spend a lot of money doing a lot of great things. I was in urban redevelopment and master planning large-scale communities. I worked in sales, marketing, product development and management strategy and it was exciting. It was amazing and it was a learning ground to see how certain parts of the world worked and there’s no greater training ground to meet and grow. I loved that.

To your question, why would a young 30-something who’s just married, first child on the way or we had our first child decide to throw a perfectly good career, earning hundreds of thousands of dollars a year in a booming industry? Throw that away to go and be a consultant. I always had that niggling inside to go and do something for myself. To not be a passenger on a train but to go and build a train. That’s hard to get rid of.

There were some other circumstances as well that probably helped catalyze that. You can build wonderful careers working for yourself or you can build wonderful work careers working for others. There’s no right or wrong but there are better fits for individuals. I certainly found that I was staring down the barrel of 10 or 20 years. My nightmare was waking up in ten years’ time with some BMWs in the garage and no life.

How long were you in that position where you saw the possibility or the potential to go off, start your own thing again, pull the trigger, decide to make the leap and to move forward?

I did not rush it. I was in a role that took me to lots of different places. The role I was in the corporation meant that I would travel to lots of different project sites and work with lots of different people. I was on the road constantly and that gave me a lot of thinking time. I was able to sit and think about it and process it. I reckon it was about a year of thinking it through and trying to wrestle with it and talk with other people, my wife, good friends and mentors. The catalyst was when I saw the company restructuring doing a whole bunch of stuff, I was like, “Now’s my time to jump.”

CSP 229 Stuart Leo | Software CEO


That was probably a little bit naïve, to be honest. I should have hung around and potentially waited until life outside in the real bad world in the JFC was not so bad. Those are the lessons you learn along the way. I took that moment to go, “Do I want to spend the next few years here in turmoil or is in turmoil the best time to jump and see these opportunities?”

Being the opportunistic idealist optimist that I am and a stubborn idiot sometimes, I jumped. To be honest, that jump was simple. It was saying to my boss, “Thank you for the opportunity and what you are putting in front of me. I don’t like it. I can forge my own way forward doing this,” which was met with, “You’re insane,” which is normal. That’s okay. To be honest, it was practical. As soon as I had said that to a few friends, I landed my first client.

I want to explore how you got your first client and subsequent clients. You then spend about nine years or maybe even more building this consulting business and more you have transitioned to building a business that is all around the software. I want to get to how you did that. A lot of people are interested in the idea of productization. We did a workshop at Consulting Success about the productization of consulting services that were very popular. It sold out. There’s a lot of interest around this but before we do that, tell me about that transition of going from having a corporate job saying I’m out of here and starting your own thing. You said that you landed a client almost right away. How did you land that first client?

It’s not what you know but who you know sometimes. In that instance, a friend of a friend. They said, “I’m going off doing this. I need this person who can help do some strategy, research and marketing.” I’m like, “That’s me. I can do that.”

How did that happen? Did you send out an email to the people that you knew when you were leaving? Were you at a barbecue having a beer and a conversation came up? I want the details of how did get that first client?

You are making me think now about the detail. That’s difficult. I was sitting down having a coffee with one of my best mates, who I still work with to this day and I said, “I’m going to go do this,” and he said, “Someone is doing that.” He set up the meeting. It was the referral straight away. I did not have a website or a business name. I did not have anything. All I had was me, what I did and my experience, which is pretty much what any consultant has at the end of the day. Take away all the fluff and bubble, that’s what people are buying.

Talk me through your next client, number 2 or 3. Aside from that initial coffee introduction, referral, how did you start getting business? Where did the majority of the initial clients come from in your new consulting business when you started?

That’s why most of them were a referral. I would say 90% were referrals. It was a case of doing some work, demonstrating that work, getting a referral to somebody else or picking up the phone and talking to the network of people that I knew.

Action creates a reaction that generates momentum. Click To Tweet

I’m a little bit more detailed because very often, people will say, “Most of my business has come from referrals,” yet their approach is very inactive. It’s referrals come to them. Great but they don’t have a strategy behind it. Was that also your case where you did great work, provide value and people contacted you or were you taking proactive steps to request referrals? It sounds like you had some strategy that you were working through.

When you say referrals, most people think, “Lucky you, you sat there and the business comes to you.” That’s out of BS. That so rarely happens. Anybody telling you that does that, that’s not true. There’s other stuff going on in the background.

What works best for you?

I’m not a natural salesperson. It sounds a bit weird because I work in sales and marketing and at that time, I had come out of that space. I struggled to have the confidence to pick up the phone and talk to somebody or to send a letter or an email. I don’t even know the basic motivation. I hate that I’m quoting Anthony Robbins in the very first quote I’m giving you. It was probably his quote that says, “Action creates a reaction that generates momentum.”

Your business world of referrals is like a bucket and when a bucket is still, all the sand or the rocks in the bucket float to the bottom and they do nothing. If you grab a big spoon or something can stir that bucket up and start shaking it up and moving it around then stuff starts hitting into each other or you get a bit of momentum. It starts creating a bit of a whirlpool. It starts building some energy, action and some momentum.

I had resolved to try and pick up the phone and ring at least ten people a day. I never did that. I probably got 2, 3 or 4 sometimes only 1 but picking up the phone and ringing somebody and saying, “How are you going? What are you doing? What are you up to? What’s working and what’s not?” Something might drop out of that conversation to say, “We are looking for X. Why don’t you put a prop forward,” or, “I was chatting with someone. They are looking for this. Why don’t I do a quick intro for you?” There’s your referral.

Were you calling those people that you already had an existing relationship with? What was the connection?

To be honest, people that had an existing relationship with but they are not like best friends. They might be somebody that I worked with, maybe once years ago. People that you could pick up the phone and say, “Do you remember me? Remember when we did this together? What are you doing now?” If you are interested in them. They are going to be interested in you. It’s that classic old saying of, “If you want to have friends, be friendly.” It’s not rocket science but there is a science to it. It was a case of picking up the phone, talking to people, trying to get that momentum moving, getting work in and looking at early days. To be honest, when I first started my first consulting business, we did very little strategy around it, even though we were consulting in business, brand and strategy.

We would take on lots of different types of work. We were still in that formation phase of going, “What should I do? I can do lots of things.” That’s one of the things. Coming out of corporate life, I was a general manager and general manager means exactly that. You can genuinely do and oversee most things across a broad spectrum of activities but you are the expert in one.

CSP 229 Stuart Leo | Software CEO


If you are good, you can generally do those things quite well, which means you can do a broad range of services. This is sometimes a negative for you out there in the consulting business because you take on lots of different types of work. At some point, you get to choose to narrow that focus. In those early days, it was talking to people.

If somebody wanted some consumer research, I would do it. If somebody wanted some brand work, I would do it. If somebody wanted some sales process or customer journey work, I would do it. It was a case of sitting there and earning my way to understand how to build this consulting business. It was very fluid in the early days. I hope that makes sense.

You ran that business for about nine years and then decided to shift into the software. Talk me through that decision. Why not continue running your consulting business and growing that business? Why shift into a completely different business model?

In order to answer that, I will go back. Interestingly, I was running the consulting business for about eighteen months and had gone through the first year, made good money. I was doing it right. The corporation that I used to work for picked up the phone and went, “We are looking for this person. Come in and work on this exact role. This is a great opportunity.” I wound down my consulting business to go and do that, which was an interesting decision. I told my clients, “I’m winding down. I’m going back into corporate life. I’m going to go do this.” That was both wonderful and extraordinarily painful. Once the bird flies the nest, it’s very difficult to get that same bird back in that same nest.

After about twelve months, I remember sitting down with my CEO going, “I think you are going to kill me or I’m going to kill you. This is not where I need to be and I’m not aligned with where you are going. You are not aligned with where I’m going. This is not great.” I packed up and walked away after about two years. That was a great learning experience for me, to learn what it’s like to step back into the comfort zone once you have made that first leap if that makes sense.

I saw that you made that transition from being in corporate life, to running your own thing, to going back into corporate life and then going back to where that nine-year stint of dedicated time working in your consulting business. What I’m interested to hear is when that’s working for you, it’s not like you have been doing it for a or two, trying to make it work and not having success. You were redoing it after almost a decade. What was going on in your mind telling you, “Now we are here 2021 or so. I want to now shift the model from services to more of software as a service?”

Every organization has seasons. My gut is there around about seven years each. I think you go through seven-year seasons. I don’t know why. I think it’s what it is. It was around the year 2007 or 2008 that I was starting to go, “What’s the next season look like?” Some of that thinking had started in the years 2005 or 2006. We had started to play with building some little products.

We had grown our business transformation service. We were a team of 15 sometimes up to about 20 people. It was a decent size consulting business. Millions of dollars a year are coming through the business. One of the things we had done was we had started to partner. This goes back to 2012, 2013 and 2014. We had started to partner with technology companies in the sales and marketing space, marketing automation and files automation.

You partner with clients; you build intimate relationships with clients, and you take clients on a journey to achieve business growth. Click To Tweet

That was back in the early days of that industry. That was interesting and it helped us understand the power of product and also the benefit of productization. By about the year 2007 or 2008, we must have partnered with 7 or 8 different technology groups and that’s common now. If you are in business transformation, you are partnering with the Adobes.

In the market, I was in the Sales Forces and the Microsofts. We were the first to partner with some of those organizations here in this country. Some of the smaller ones, at least. Anyway, in fact, I remember back in 2012, 2013, 2014, people like HubSpot ringing us up going, “You have got to become a partner and do this and do that.” I had no idea what that meant, by the way and I didn’t have a technology background. What we learned was the power of product and we learned the power of systemization. We learned the power of repeatable work. We also learned the shortcomings of product.

It would be helpful if you could outline very briefly what you have experienced or found is the benefit of product or productization and then any downsides or challenges as well, in comparing a productized model to a service-based model.

It was a completely different business model. If you are thinking about productization, you need to hear that if you want to go and build the product, you either need to A) Blow up your existing services business, B) Choose to be blown up. This is not a mutual experience. You are either a product company or a service company and don’t try and confuse the two. To be honest, that was one of the mistakes we made in the consulting business that we learned too late and we were a great services business and then we started playing with building our own product. We spent way too much time and money. It started to impact our traditional service models.

We realized and as I started to talk to other people who had gone through the journey, I remember meeting some people in San Francisco and sitting down and listening to them talk. They were telling my story. We are a consulting business during this and this, maybe $2 million or $3 million a year in services. We played around with product but we had started to suck at everything because we were trying to do this broad cross-section of services.

It wasn’t until we made the bold decision to go one way that things start to work. You have to choose. You cannot be a professional athlete and a professional hotdog eater. No offense to professional hotdog eaters out there. They’re two different business models and it’s the same with services and product. We played around with some products. We were having some isolated success with product and we hit this junction point. This is in our business transformation consulting business. It was pretty brutal. It was over a period of about 1 to 2 years I was going, “The business I’m running is not necessarily the business I started back in 2009 and 2010.”

What was the big difference? What rubbed you the wrong way or what was the feeling that you were having and what was causing it?

When you are a services provider, you partner with clients. You build intimate relationships with clients and you would take clients on a journey and they take you on a journey and that journey is helping that client achieve that business growth. If your business is in the business of turning on technology then you become a churn and burn. You are not interested in the successful outcomes of the business. You are interested in quick, get that implemented, get that start and get onto the next thing. We had this situation inside our consulting business, where we had a small number, maybe 3, 4 or 5 intimate, high value consulting engagements and then maybe churning 30, 40, 50 clients a year in these technology environments. We had these products and we realized we were running about five different businesses in one.

CSP 229 Stuart Leo | Software CEO


That’s like grinding the gears at every movement. It was an interesting moment. I knew we had to step back and go through a big reinvention. It took a couple of years to build up to that. It was interesting. I got to the point where my wife and I were looking at the business and we had figured out this other business to go and do. This is back in 2018, early-‘19 and we were like, “We are going to go and do this. There’s a market opportunity over there but that means that probably means winding down our consulting business.” That’s okay with them. I called up a friend, a mentor or somebody who I highly respected who’s in that space of helping organizations merge, acquire and whatever you like.

We had a number of conversations by this stage with investment bankers and people ringing us up going, “We want to buy you and roll you up with that.” Doing all these things, we are at that stage of either be bought, be broke or do something else. It was one of those interesting moments. I said to him, “I have business A. This is my existing consulting business. I have got business B, which is a business plan and a business model and a market opportunity. I think we want to be doing business B but we have got this ten-year-plus business A sitting over here that you can’t turn off. Do something with it.” I said, “How do I get from business A to B?“

He’s a very clever man and he sat with my wife and with me over the period of about three months and by that, it was not too long into the conversation. We had a number of sessions with him. He looked at me and he’s like, “When you stand up and talk about business A and what it does, there’s something in you that turns on. The light goes on. When you talk about business B, which you could make a ton of money and do it, you get cold.”

Business B is a new concept or that’s the existing one?

Business B does not even exist anymore. It was the thing we were going to do. He said, “You need to be doing business A but maybe you just have not got the business model right on business A yet but what you are doing in business A is where your heart’s desires lie.” That resonated with me because I love that old Voltaire quote. I want to do it justice. “Wherever the world’s problems lie and wherever your heart’s deepest longings lie then that is where you will find meaning and purpose.” Wherever there are deep problems to solve and deep longing and passion, align those and you will find meaning and purpose and hopefully profits as well at the same time if you do it well.

That was not the answer I wanted. I wanted him to go, “I love business B. Let’s go. Spin that business out, raise some money, go ahead and conquer the world and we will just sweep all the problems in business A under the carpet and close that chapter and life will be peachy.” Instead, he goes, “I think your meaning and purpose is found in some of the things you are doing in business A, not in business B.” I knew he was right in my heart of hearts. I knew that I wanted to find the easy road, if I could put it like that.

I turned around, sat down. I’m like, “What are we going to do?” I feel like we have got to face the monster we have created. I’m being very intimate on this show. I’m probably going to get into trouble with some people and things I say. That started a very painful journey. I knew from past experience that if we wanted to do a product-based business and make that transition from product, we had to go through some significant pain. We had to go right back to the beginning and start again. I also knew that the product business we wanted to do was that all the IP and the brains of that new product business were inside my existing consulting business.

I’m going to ask you specifically, you have this business that you are saying is generating millions a year in revenue. You have a sizeable team of 15 to 20 people. What happens to your existing clients and employees? Can you walk us through the different pieces and what changes you had to make to go from a service-based business to now potentially a small starting point for a product-based business?

Wherever the world's problems lie and wherever your heart's deepest longings lie, then that is where you'll find meaning and purpose. Click To Tweet

That’s painful so thanks for bringing up the pain of the past. We knew we had to wind down, which is a horrible thing to do in a business. Most business people think that winding up is the only thing you should ever do. Winding down is a negative but you got to think about business like fields and harvest, fields in a farm. Sometimes you harvest sometimes you sow sometimes you move that crop from one field to another crop so that the earth regenerates and it gets different minerals, nutrients.

Sometimes you wind up and sometimes you wind down. That’s the seasons of life and you shouldn’t be afraid of that. We went into our winter of wind down and we knew that we were not going to pursue new certain types of projects. We started going slow on those. We have to stop investing in certain partnerships that we were in, which we knew were ultimately going to seize up and stop. That was all okay and as those projects wound down, we did not replay stuff.

Did you call up any clients and half tell them, “We are not going to be able to continue.” Do you work through every project that you had until it came to that natural end?

Some clients will say, “We are not going to take on that work.” We say, “No, we are not going to do it or if we are going to do it, it’s going to cost an extra,” and prosper those out of pocket. This was the other thing that was happening at the same time. Some of the other clients had been saying to us, “We don’t want you to do some of that stuff but we want you and your team to be over what our business is doing in that area.”

That was interesting. I had clients that were down and said, “I want you and this person and that person working on our business. We were not doing that stuff but we want those people in your business who have been doing that stuff for other people to help us make sure that the people we hire to do that well.” That was a weird position to be in. What we found was a small number of our clients, 4 or 5 of our clients, were saying to me and some of the key leaders in our team, “We want your advisory, not your coaching or consulting.” That was a significant learning point.

You accepted and embraced during that transition or did you say no to those opportunities?

That was something we said yes to.

You went from doing hands-on consulting, implementation, support work to more advisory work. Would you say that is what helped you to bridge the gap between running a full-blown consulting services-based business and at the same time working events transitioning to working on the product business? Did that help with cashflow during that time?

CSP 229 Stuart Leo | Software CEO


It absolutely did because a number of clients said, “We want you to do this and this and we are going to pay you pretty much the same amount of money to bring the advisory and the oversight, as opposed to doing it as well.” We were like, “Come again?” That was probably the biggest learning insight in the consulting journey. This is very much the proposition we have with the software. When you start out in consulting, you do a broad range of things. The way you grow is to find your niche. Most consultants have this broad array of services that helps them capture lots of fish. They can eat and they can capture lots of those small fish and eat and get moving and get going.

Over time, they go, “I want to stop catching lots of small fish. I prefer to catch 1 or 2 big fish.” The way you do that is by starting to niche. You have a niche in and you could become an expert. You have got to move from that generalist at a good, into great, to that expert. That’s the journey most coaches and consultants go on but the problem with that is that you often end up in a gig to gig world.

There’s a third step to make and I did not know this. I don’t think most consultants know this. You have got to make the step from expert to advisor and when you make that step from expert to advisor, you are going back and drawing on all of those general skills. The broad cross-section of skills across the organization and moving those from good to great again but not in the doing but in the execution of. Does that make sense?

It totally does. It’s telling a lot of people might want to do earlier on but if you have not proven yourself, delivered enough value or have enough recognition, it can be challenging to get right to from start to advisory work. You have to put in some of the work and some of that experience and expertise to get to the point where clients are seeking your advice as opposed to you doing the implementation work for them.

It’s almost a keen in the corporate sense when a lot of graduates join corporates and tend not to do this so much anymore but the good organizations do this. They will take a graduate and they will say, “We want you to work with us for a decent amount of time, which means for the first year or two, you are going to work across sales, marketing, finance operations, product and R&D.” You are getting these general learning of the organization and then you might land in finance, strategy, ops, product, R&D or whatever it might be and you end up doing a series of stints in those specialist areas. You are moving through the organization because they are so big in different roles over the years, ultimately landing in some executive role.

You know the guys in finance because you ended up doing three years there. You know the guys in product because you had spent some time there. It’s the same journey. You have got to be able to move through the different parts of the organization and understand how the organization works, both from the leadership, strategy, technology, operations and the product and then you have to be able to bring those threads together and help leaders and leadership teams transform them. That was an interesting insight.

I want to ask a couple more questions before we wrap up here and be conscious of and respect your time. You have the experience now of running a full-blown consulting business. You have the experience of building out this productized software offering and business. When you look at the marketing of what you have seen work well in services, as opposed to marketing in the product world, are there a lot of similarities? Have you found big differences in terms of what works from a marketing perspective? You mentioned with the consulting, a lot was based on referrals and you being very active in reaching out to people and doing great work. As you are still in the relatively early stages of building out the software product, where’s your focus around marketing?

The principles are the same. What’s your value proposition, why different, what problem do you solve? All these principles are the same. You can’t get away from those. The execution of those principles are different. It comes down to how you answer those specific questions. In fact, I’m going to be a little bit self-promotion here because I’m going to talk a little bit about our product. Our product is a software platform that helps businesses diagnose, plan and deliver but it’s built off seven questions. Those seven questions came from a lesson we learned from the British Military. We started working on these questions in our consulting business several years ago because it’s the insight we gleaned from the British Military. I hope you give me the indulgence to go for two minutes into this.

When you start out in consulting, you do a broad range of things. The way you grow is to find your niche. Click To Tweet

When they were struggling to move from the Cold War to the Hot War from the 20th century to the 21st century, from a traditional world to a traditional world, their decision making, strategic planning and their leadership practices were not functioning correctly. Their old ways did not fit the new way. The way they solved that was by going back to core principles. The way they solved it was by saying, “The best way to build a battle plan is to ask and answer seven questions.”

If you ask and answer these seven questions, you will develop the highest and best course of action to meet the objective. It does not matter what battle you are in. It does not matter whether you are air, sea, land, intelligence or special forces. These are the seven questions to ask. That was something that I learned about in 2009, 2010, 2011 and 2012. I spent ten years saying, “If the military can only ask seven questions in any battle anywhere in the world, geography, warfare or any part of the Army, why can’t a business ask seven questions? What would those seven questions be or a small set of questions at the time?”

How do we take that out of the British Military and put it inside the boardroom of a small business or even a big business? This is a long way of answering your question. I believe that there are only seven questions you need to ask and answer and that’s what we did with our clients. That’s what helped us move from good and expert to advisor. It was the process of asking these questions.

For ten years, I’ve been on a team refining these questions and until such time, as we got to the point where, like the British Military when we were asking to answer these questions, when the military answered, they also have a piece of software in their hand. It was helping them answer hard questions effectively with great intelligence.

The reason why we built a product business was that we built that software where you went. If you are going to ask and answer these seven questions in the heat of battle to figure out where to go, what to do and build the most valuable course of action, you need some software in your hands. We were doing that manually for years.

We turned around and we are going to build that software. You asked me the question, “What are you doing? What’s different?” When we were running a services business and generating millions of dollars a year, we were asking the same questions. When we were advising a publicly listed organization generating billions of dollars of revenue a year, we were asking the same seven questions. When we were working with a startup and helping them get their first revenue, we were asking the same set of questions.

Have you changed? There is a lot of writing about the seven questions online. What is the situation? How does it affect me? What have I been told to do and why? What effects do I need to achieve? What direction my stay I give to? I’m seeing these online. Have you altered or changed these questions?

Absolutely. British Military, your seven questions are amazing. If you want to blow something up then answer the British Military’s questions. If you want to build something up and build an organization, you need a different set of questions. All we took from the British Military was the principle of asking the questions and got a small number of questions, creating the transformation required if asked and answered on a continuous basis so we rewrote those seven questions.

There's no one size fits all answer, but there are some core questions that every organization should ask. Click To Tweet

Here’s the shameless self-promotion. Go to the Learn tab and look at Waymaker’s leadership curve. It’s got seven questions on it. Those seven questions take you around seven areas of the organization. Clarity of vision, market focus, strategy, business model, customer experience, which includes sales and marketing service. Clarity of the employee experience. The question of action, clarity of goals. What are the 1, 2 or 3 things that have delivered, shifted the needle on the organization?

What sits behind that is a piece of software that when you ask and answer those seven questions, we have mapped about 250 odd data points of an organization and tell your team to answer that diagnostic in 5 to 15 minutes. It is going to tell you where the weaknesses and strengths are and where the gaps are. When you answer the questions, your answers are unique to your situation, your customer, marketplace or business. This might mean that if you are a product business, you need to be doing X, Y and Z. If you are a consultant specializing in business sustainability, you need to be doing A, B, C. If you are a consultant advising on creative marketing then do E, F, G. There’s no one size fits all answer but I believe there are some core questions that every organization should ask.

I want to make sure people are not hanging. Before we wrap up, when you look at the marketing that you are doing, what would you say is working most effectively for you with the productized software business?

The most effective marketing we are doing uses a combination of clear value proposition, direct outreach using some smart AI some smart customer journey management that does all the heavy lifting for us and surfaces leads into our inbox of people going, “I’m interested. I need this. I have the problem that you are solving. Help me use the product.”

Is this done through email or through LinkedIn? How are you contacting these people?

It’s a combination of all the above. There’s no one platform that does everything but it’s a combination of LinkedIn, retargeting, database outreach. It’s about identifying who you serve, being clear around the problem they face and then having simple messaging and we are still junior young at this game. I’m not pretending to be a genius.

For context for readers, we are months into our product journey. We are still a startup in this space but our second quarter compared to our first quarter, was about 10,000% approved. We went from doing maybe 1 or 2 business diagnostics a week to over 60 or 70. It was starting to ramp up and we now have partners in the UK and Australia and talking to our first in North America. We are in that starting world.

It’s a combination of knowing who, where they are, what problem they face, presenting a clear value proposition and then using smart technology and customer journey management to take them on a journey and say, “Talk to me.” I don’t know if I can be more explicit than that. Does that answer your question?

That’s good and we are going to wrap up here. There’s so much more that we could dive into and explore but again, I want to respect the time that we have., where you can learn more and those seven questions highly recommend that people check those out. Stuart, thanks again so much for coming on.

It’s a pleasure and I wish you all the best and great success to you and your consulting community.

Thank you.

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About Stuart Leo

CSP 229 Stuart Leo | Software CEOI lead the team at Waymaker is the intelligent business strategy software that helps you dynamically manage business growth and goals in the 21st century.

Like a smart watch listens, diagnoses, tracks and empowers a user to set goals for a healthy life; Waymaker listens, diagnoses, tracks and empowers users to set goals for dynamic business growth.

Feel free to connect, reach out or message. If I can help you I will.

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