Bessi Graham: Understanding Decision Cascade And Double-Sided Legacy | Ep. 188

COGE 186 | Decision Cascade

Business owners have a lot on their plate at all times, which is an overwhelming job. This task can become more manageable through the decision cascade method. Eric Anderton delves deeper into this concept with award-winning entrepreneur and podcast host, Bessi Graham. She explains how to navigate through unnecessary noise, gain clarity with your goals, and understand the context of every decision you make. Bessi also discusses how to create a legacy you can be genuinely proud of and without neglecting your core values.

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Bessi Graham: Understanding Decision Cascade And Double-Sided Legacy

Decision-making is a tremendous challenge, but it is a skill that you have to get very good at if you’re going to be successful in your business. How do you get better at making decisions? That is the topic of conversation with my guest, Bessi Graham. She is an award-winning entrepreneur with many years of experience working with business owners, governments, and large funding bodies to bring doing good and making money back together.

She’s had a very interesting career. From the grassroots of sitting in the dirt and working with business owners in the Pacific Islands to the United Nations headquarters in Geneva, Bessi has seen it all and brings an unparalleled perspective on what makes change happen. We have a tremendously interesting conversation about how to make good decisions and the importance of clarifying your vision and strategy, and how that clarity then helps you to sort through the noise of the various inputs that you’re getting on a daily basis to identify the key decision from which other decisions will then cascade.

Bessi gives a number of practical examples to help you to understand this concept and how you can apply it in your business. That’s the first half of our conversation. The second half of the conversation then pivots to your legacy and how you need to combine your time, talent and treasure with what you’re interested in to create a legacy that you can feel good about.

Bessi has experience working with companies on both the decision-making part of the discussion and the legacy part of the discussion. You’ll find content that will be very beneficial to you in both parts of our interview. Enjoy my conversation with Bessi. Feel free to share it with other people that you know would benefit from this interview. Thank you.

Bessi, welcome to the show.

Thank you so much.

Why is decision-making so difficult for business leaders?

The primary reason that it feels difficult and overwhelming is that it’s very hard to decipher or figure out which decisions are most important. We feel overwhelmed because there are so many moving parts. Often, the things that allowed us aren’t necessarily the most important. It is down to that complexity or complicatedness that is in the mix with all of the competing interests and voices that we have coming at us as a leader in business.

You’re saying something interesting there with the loud voices. How did the best leaders discern the difference between volume and importance?

You have to have that ability to pull back, look at the whole system and be able to see, “Is this something that by sorting it out, making this decision or listening to that noise, I will unlock a whole bunch of other things, or is it something that’s not a strong lever for us to pull?” The urgent things aren’t necessarily the most important. As a leader, making those judgment calls and being able to be confident enough to examine what’s in front of you, decide what is most important, where you will give your attention and what you will ignore is part of our job.

How long should I listen before I decide?


When you make a decision that is not central, it constrains all your decisions that follow. Share on X


In some ways, that depends on the level of understanding that you have of the context that you’re operating in. If we understand both the context we’re operating in and where we want to go as an organization, then you can pretty quickly hone in on whether this is actually something that is going to be able to help us get to where we want to go, and whether it’s something worth paying attention to. It comes down to having to have done the work. We need to be very clear on where we’re going and deeply have that mastery of the context and environment we’re operating in because that is where you can then make very quick, aligned, efficient decisions.

Where do leaders tend to miss the important aspects of the context in your experience?

The biggest challenge comes down to being caught up in our own perception, or projecting onto the context or onto other people what we think is important, or assuming that they have dealt with or have the level of mastery we have. In reading that context, the problem comes down to if you haven’t understood the audience, who you’re speaking with or who is speaking at you if it’s about that loud volume.

Tuning into and making sure that the way you engage is appropriate for that audience within your context is a critical aspect. It’s the level of empathy and being able to say, “This person thinks this is important for a reason. What is it that’s going on for them or within their particular level of the system?” Remember, as a leader, you have visibility over far more levels of that system than other people do.

Your mental capacity to drill down and go, “What are they seeing? Why does this seem so important? What are some of the context I could give them that doesn’t make them feel that I’ve written them off and ignored them but says, ‘Here’s why this is not something we’re going to focus on at the moment.’” That would be a critical piece of reading the audience and understanding what they can see off the system.

Can you give me an example from your experience of a leader who has done what you’re describing very well?

When we think about context and then vision, often people come to mind who are good at one of those pieces, not necessarily two. There are lots of visionary leaders who paint this picture and want to draw people on that journey but haven’t read the context well. The example that comes to my mind is the opposite. When I did my Master’s many years ago, I was focused on a whole bunch of interesting things around counter-terrorism, leadership, and how we draw people to that vision that we have.

I studied three leaders of a country in the Pacific where they had come into independence and come out of intense situations where they were guerrilla warfare type of leaders. They had this incredible vision of where they wanted their country to go but failed to read the context of that. What they were doing was using their preference for leadership. They were good at being that charismatic leaders that got people on board, and they did not read the context. Now they are in a country that had achieved independence that needed stability.

In a business context, we often have that same piece in different phases of our business. In the early stages, you might have needed to be that charismatic leader who told people what to do, and they would follow. The misreading that these leaders had was no longer being able to see, “The leadership style or approach I took that worked previously is not working now because we need to do the hard work of getting the systems and processes in place, having structure and management.” I’ve seen that connection over and over again in the last twenty in a business space.

As a leader, the importance of reading context is that your personal preferences of leadership style or any of those kinds of aspects are not the key driver of whether you will be successful or not. You need to adapt to the system and the setting that you’re in. That piece is where it becomes critical because otherwise, we keep doing what we’ve always done. We wonder why we feel frustrated and why people don’t understand what we’re doing. The downside of not reading context is a good lesson in a business context as well.

What is a method of decision-making that you found to be very helpful in these complex situations for a business owner?


COGE 186 | Decision Cascade
Decision Cascade: As a leader, you must make those judgment calls. Be confident enough to examine what’s in front of you, decide what is most important, and where you will give your attention.


The method that we use is called a decision cascade. What it’s about is starting to find ways to identify what is most important here. If we think of that aspect of searching for significance, we can see all of the moving parts. As a leader, one of the things you will be good at is spotting opportunities quickly and seeing what needs to happen. That sits in a first-level category.

If you think of the old, “What? So what? Now, what?” Seeing all the moving parts or the decisions that need to be made is sitting in the watch category. You can see those things. The decision cascade is about helping you to figure out, “What are those things? Where does significance sit? Where are my priorities? Which of these things are more central than others?” The reality is they are not all-important.

Let me role-play one for you. Let’s say I own a construction company and I have an opportunity to take on a project that is in different geography from the one that I’m currently in. Maybe it’s with a client that I like working with and a project type that I’m good at, but it’s in new geography. That means I’ve got to get new relationships with suppliers and subcontractors. The risk element has increased. How might I use the decision cascade to work through a scenario like that?

There are a few aspects. You want to look at both mapping out all of the decisions that you feel are part of coming to an action point with that. You then figure out both which pieces are aligned for you as a business to where you want to go and which pieces then are most conceptually higher up the system.

For example, the conceptual piece is saying, “If there are fifteen different decisions in whether or not we go into this new geography, are there some of those that by making that first, the other pieces dropout?” For example, if we can’t even get key partnerships in that new location, it’s irrelevant whether we want to operate on the ground. For me to start thinking about which of my team members I could send there doesn’t matter because we don’t have access to key partnerships.

It’s the teasing apart of conceptually which decision comes first. That can be a nice first way to level or structure importance. It can be, “Is there a decision here that other decisions can’t be made until that is made?” The sequence is important. On the level of a business, you want to also be pushing up, “Are there certain things that are central to us or important? Do we have a sense of culture or how we make decisions here that have to be taken into account in the prioritization of these decisions?”

As a company, if you’ve been under a lot of pressure for the last five years, and you have committed to your team that, “We are not going to be making you be traveling big distances or being away from your family for extended periods of time,” you might then say, “For this chapter that we’re in as a business, we already know that unless we can have the partnerships and hire a completely new team in that geography, it is not aligned with our business for us to take this work on.” Looking at the conceptual and the business alignment can help sort out that significant piece at your first level.

The idea then is to identify the decision, which will then affect another series of decisions and understanding of where to start. Not starting further down the chain, but going as far up as you can then, and then seeing how those structures cascade from there.

What can often happen is if we make a decision, first up, that is not central. It constrains all of our following decisions. If we already say, “I’m going to hire someone to figure out and start breaking into that new market or that new geography,” the fact that I have committed a cost structure to that, that I’ve already hired someone that I’ve already spent money, means that I will start forcing myself into a certain way of making this decision.

Those pieces are important because they can limit the next decisions or they can shrink the way we look at a new opportunity. Also, it can mean that you end up doubling up and spending money or time more times over because you have to come back and revisit that decision later because the sequence wasn’t right.

I know we were talking before we got started about the decision you made in your personal life that you use the cascade method around. Can you explain that a little bit to give us context?


Having clarity means being brave enough to say no to good things and focus on a bigger end prize you are trying to get to. Share on X


The example I was talking about was when our kids were younger and we were thinking about, “Did we both try to have intense careers where we were traveling and where we were doing different things?” At a personal level for us, the priority came down to we didn’t have kids for someone else to raise. We wanted one of us to be a primary caregiver. We wanted to be present with the kids while they were young. That pushed off a whole bunch of decisions suddenly of which jobs we took. It meant we started at the point of saying that we want one of us to be with the kids while they’re young.

It pushed down to a secondary level a whole bunch of other things that could have driven our decisions. We could have said at the same time we are thinking about, “Where did we want to buy a house? What kind of cars did we want to have? What schools would we send our kids to?” By making that primary decision, it then made me realize, “If we commit to a house that requires us to have a mortgage where we’re both earning, we suddenly have flipped things to the wrong order. Let’s buy a house that we can afford with one of us having a salary. Let’s send our kids to the public schools so that we don’t have to have the salaries that require the level of both of us working.” We sold one of our cars.

We pushed to secondary-level decisions that if we had let them drive things, we would have suddenly been trapped in a situation where our focus was not able to drive our decisions. Instead, we had made secondary and tertiary decisions primary, and now we felt constrained. What you see in businesses all the time or in people’s personal lives is you suddenly have commitments that limit decisions which would have been more fulfilling and aligned with your strategy or your personal values.

It was pushing those things down the cascade and saying, “We are having as this primary decision being with the kids, and then everything else flows from there.” Our decision was the best person to be at home was my husband. We then had to have decisions below that on how do we make sure he’s not bored and that he’s engaged because he has a PhD. He’s a clever man. What is his intellectual stimulation? How does he have adventures?

You have to then flow down each decision to say, “How do we make this sustainable? How does this work?” Always coming back to asking the question, “Are we starting at the right place so that what is truly important, that decision gets made first and it will flow from there?” It’s the old piece of put the big rocks in first, don’t fill up with the sand and pebbles.

How do you ensure that the right pieces get attention? The decisions and the amount of decisions that we have as business owners are critical because otherwise, the busyness will take over. We’ll suddenly realize we’re not on track with our strategy or our revenue plans. We are in the right place, but we have made commitments and decisions that lock us into pieces that are not getting us where we want to go.

What I hear here is that if I’m going to get good at this decision-making from a business point of view, I need to be very clear about what my business strategy is and also the values that drive the way that I do business. Why do you think businesses sometimes struggle with that strategic direction? What are some of the sources of that struggle?

As leaders, it comes down to our strengths and our weaknesses. The piece that is deeply part of who we are is that we want to drive to action, that we’re good at making decisions, that we will take on board things that other people would be scared of doing, and our risk appetite is higher. Those aspects are great and a part of how we succeed and how we make things happen that others would not do.

At the same time, it can mean that we fall into that trap of mistaking movement for progress. We think by being busy and doing lots of things, we are making progress. I suppose the thing that you learn over time, and that comes with wisdom and experience, is to stop and get clarity upfront about who you are and want to be as an organization, what does that actually look like?

The aspects of that bigger picture strategy of like, “Where are we going? What would success look like for us as an organization?” To get clear on those things mean that when we flip into that action mode, that achiever mode and make it all happen, we can make very quick decisions but they will be aligned. It’s not about saying, “Let’s always have long-drawn-out conversations,” but it’s saying, “Clarity upfront allows you to be efficient and effective and move quickly,” rather than what I see very often is we’ll make a quick decision, but then we will have six months of stress after that because it wasn’t a very good decision. Now you’ve got the pressure of all of the consequences of a poorly made decision because you did not have clarity and you could not figure out among all of the moving pieces what was most important to focus on.

If I have clarity on my strategy, my values, and those types of things, that will help me to go through the complexity or filter the complex inputs that I’m getting over all the time through different business situations or the loud voices, and focusing on what’s most important for my company. In your experience, what are some of the best ways to do strategy or to figure out that strategy? What are some of the best questions? What are some of the best methods that you’ve used with your clients or that you’ve seen other companies use over the years?

COGE 186 | Decision Cascade
Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork

I am a big fan of the old strategy saying, “No to good things.” It’s the piece of just because something sounds like a good idea or could have a great outcome doesn’t mean that you should do it because there are plenty of great opportunities out there. The first piece around strategy for me is that aspect of having such clarity that you will be brave enough to say no to good things and focus on that end prize of where you are trying to get to. The next piece is around some of these aspects of as we focus on where we want to get to, you need to be able to reverse engineer back from that and figure out whether you took what you’re doing now to its logical end.

Often we’re so busy that we don’t run it through and go, “I’m spending all the money in the business here. I’ve hired these roles. We’re focusing on these projects.” Run scenarios. Strategy for me, and part of your job as a leader, is you should be thinking multiple steps and multiple timeframes ahead of other people.

You need to look at what’s happening, look at the activity in the business, run that through to its logical end, play the scenario out and say, “Is what we’re doing now going to get us where we want to go?” I like a strategy that dances between running scenarios forward, running them to their logical end, and then reverse-engineering them back from a goal. In different situations, I’ve found with clients and myself that one of those will be more effective and give you insights in a better way. Being able to do both is useful.

Have the vision, reverse engineer it to what you should do now, or look at what you’re already doing and what you’re committed to, run it forward and check if it gets you where you want to go. Those are some of the pieces that I love using from a strategy point of view because it grounds us to not see strategy on paper as disconnected, “Let’s think about great things we could do.” It deeply connects it back to the actual activity of the work we have to do, “What does this look like in action and how do we ensure that the strategy makes sense?”

Let’s look at the run-it-forward perspective because it’s correct to say that leaders need to see 2, 3, and 4 steps ahead. Perhaps as a leader, that’s not one of my strengths. I might be able to do the vision part very well, but I may not necessarily be able to do the ramification part. What are some methods or strategies I could use to help get better at that running it forward perspective?

There are two pieces that come to mind. One is there’s a great book called Who Not How. As a leader, you need to figure out those components where rather than always going, “How do I do this?” You think, “Who is the best place to do this?” It’s okay if, as a leader, you’re not very good at that detailed planning or the mapping out of how are we going to get there, but who is best placed to do that?

It may be that you have a two or someone who’s very operational, whose brain operates like that. Part of what you do is work together on those types of projects, and for you to set the vision and say, “I’ve got a rough sense of how we’re going to get there, but I need your help to flesh this out from a scenario point of view, and be able to see what am I missing and how do we do this better?”

As a leader, our job is not always to be the answer but to be able to identify where we find that answer or who can help us figure that out. That’s an important shift as a leader to not see that you have to be the answer to everything because the more complex, the bigger the business, and the bigger the projects, you can’t possibly have that breadth of experience. I would start with that and think, “Who do I need to bring in?” The second point would be around if we go back to why it’s important to know yourself, your values and your vision. When you know yourself well as a leader, you can communicate those aspects to your team.

For example, for me, I love strategy and painting that big picture vision, but I think in chapters or horizons. I don’t go into the level of detail in each of those horizons or chapters about the exact step-by-step of what will happen, but I can tell you the heading of that chapter or the naming of that horizon, “There are going to be four steps. These are the chunks of what’s going to happen to get us there.” I know that about myself, so I don’t try and be something.

I’m not focused on weaknesses. I’m very much a strengths-based person. I figure out what you’re good at and then bring people into your team who complement that. Those would be the two pieces I would recommend leaders to think about who, not how, know yourself and own where you’re good. Lay out what you can of that scenario and then get others on your team to flesh it out and work with you to make sure you’ve thought it through.

Let’s say I’ve found myself in a situation where I’ve made an important decision in the business, and I’ve seen it begin to run out and play out. I discovered that I had made the wrong decision. What do I do then?


Leaders are not always the answer. They are the ones to identify where to find the answer or help figure out the problem. Share on X


This is such an important thing because the reality is it’s going to happen. You will make decisions that don’t play out the way you think they will. We are living in such a fast-moving environment. The last few years have shown us that all the scenarios you played would never have anticipated what was coming. The challenge here is not to see any of these tools, frameworks or strategies if you think about those aspects, even in the way you talk about your work of that 1% of inspiration.

Don’t think of these tools as being something you do once, and then you’ve got the answer. In this work, we always talk about whether it’s business modeling, business planning or any of those strategies. There’s always an “ing” at the end of it. We’re not doing a business model once, laminating it, putting it on the wall, and that is our business model.

We’re not doing business planning once. It’s planning. We’re learning the tool, the strategy and the way to think. That equips us to not have a fear of, “What if I make the wrong decision? I use that framework now when it plays out that I get a few months in and I thought that was the most important thing, but the whole market has shifted, or I misread how my team would deliver on this project.” Go back to the same framework. Use the components of the culture or the values of the business. Use the conceptual leveling of saying which decision needs to come first and revisit it.

When it changes, your decisions and behavior should change. As a leader, we need to be able to make decisions quickly, which is where having alignment and clarity upfront is important. We also need to have the level of humility to say, “It did not play out how I thought it would. Let’s shift and change.” Digging your heels in just sticking to a decision is the worst thing you can do as a leader. It will cost you money and time. You’re only going to have to revisit it down the track. Use the framework and the skill to pick that up quickly and go through the process again.

You make a very important point there about we are learning a way of thinking and approaching our businesses. I want to make sure I’ve got the order right here. You begin with your vision or culture, which then helps you to figure out which are the most important decisions. That cascade of decisions then leads to a series of actions, which then gives you feedback.

You can then decide which ways you may need to realign, whether you double down on a decision or put up your hands and say, “We were wrong on this.” Because you’ve learned that way of thinking, then you can keep going and iterating through the process with confidence that you’ll eventually get to where you want to go to.

It allows you to respond when things don’t feel comfortable or they’re not quite working because you’ve laid out that sequence of decisions. It allows you to come back, even with the person who might be struggling with it. I’ll use the personal example I gave before when our kids were young. At moments in those last years where my husband would say, “I’m bored out of my brain. I don’t want to do this anymore,” we would go, “We acknowledge that. Let’s look back at the decision. Do we still want one of us to be with the kids?” We’d say, “Yeah, we do.” “Are you still the right person to be there?” “Yes, I am.”

“Something at that third level down is not working in terms of how we make this sustainable for you. What do we need to do for you to not feel so bored and overwhelmed here?” We’ve got to fix it, but it doesn’t mean we have to go back and change the first decision. We don’t suddenly have to go. “We’re both going to be on a plane constantly and never at home with the kids.”

Don’t jump back to the first decision. Ask the questions to check, “Are we still in the alignment around the first decision?” Fix it at the level of the system it exists. Often, when we feel stressed or under pressure, we throw everything out and we go right back to square one. By using that strategy, you can see where the problem lies, fix it at that level, and don’t escalate it.

I want to reiterate this because what you said there was very important. You have the big picture decision that you’ve made, “This is what we want,” and then the cascades come down from there, as you said. They’re secondary decisions and then tertiary decisions. You need to pinpoint the place of pain in your current situation so that you don’t throw the baby out with the bath water.

That’s what we do under pressure. We go, “This is not working.” It’s like, “At which level is it not working?”


COGE 186 | Decision Cascade
Decision Cascade: Whether it is business modeling or planning, these strategies always have an ING at the end. These are not only done once.


For instance, if I’m running my business and I’m struggling on a project, I’m building a project and it sucks, I might think, “I’m never going to do that project again.” What about if you’ve got the wrong people involved in the project and you need to switch the people out, and that will fix the issue, or perhaps you have processes in place that are not working?

Instead of saying, “I’m never going to do that project again. I’m never going to work with those people again,” perhaps it’s a matter of process or the people that I’ve put on the project that will help to fix the issue. That’s very helpful. Bessi, to shift the interview here a little bit. What have you achieved that’s unusual for your peer group?

The most unusual thing for me is that I love to operate at two extremes of the system. I’ve been in the impact investment space, building the capacity of organizations and small and medium enterprises to help them figure out how they can integrate doing good in their business. I’m very passionate about business has an incredible role to play in the world. What I found is people tend to either be a big picture person. They work on huge projects or with government and big funders in my world or they work down at the level of an individual business and work on the strategy at that level.

My approach has been that I love both ends of that spectrum. Part of what I bring is I can understand the whole system. I work with governments and huge international funders around building environments for businesses to flourish. I still do the work of traveling across the Pacific islands and sitting in the dirt with a coconut farmer and understanding how their business works at that grassroots level. I’m an advisor to governments. When I’m having those conversations, I’m not someone who’s just academic and disconnected from reality.

I’m able to tie it right back down to how an individual business owner operates. To me, that uniqueness of bridging both ends of that system is where the power comes up. I can see things in a different way than someone who sits in an office all day. It doesn’t understand business, but when I’m working with a business, I can be pragmatic and say, “Here’s how you need to play the system because this is how it works.” That would be the unique angle I bring.

What’s the most courageous thing you’ve ever done?

It probably is the aspects of where I go. I’ve spent a lot of time in places like Papua New Guinea by myself out in the middle of the Highlands, very remote, obviously with security in a place like that, but it’s the aspect of, “I’m a practitioner.” I never want to be someone who’s giving academic advice on things I don’t understand. I’ve built multiple businesses. I know what that feels like. I’ve been out with communities that are struggling to operate. I don’t just have an opinion about that. I know what it looks like on the ground. It’s the practitioner in me, being willing to go where the action is and speak from a place of understanding, not just opinion.

What’s what is one mainstream or consensus view that you wholeheartedly agree with?

Probably, the aspect of the broad concept of, “It takes a village to raise a child.” I take that into not just raising children but every aspect of life. It’s the view that says, “No one person is the answer to any big thing.”

What is one thing that you believe to be true that other people you know think is crazy?

The deep belief that you can do good and make money at the same time. You do not have to choose, “Am I going to contribute, so therefore, I have to work for a nonprofit. I have to go and give all my money away,” or if I’m running a business, it’s purely about making a profit. I don’t believe that I’m very much someone who loves bringing contradictions back together and saying, “Who says you can’t do both those things?” I love proving that you can.


You can do good and make money at the same time. You do not have to choose. Share on X


When someone says something like that, some of the thought that pops into my head is the entrepreneur who makes a bunch of money in a relatively selfish manner, who then gives back as a way of a swaging their guilt.

There are plenty of those. I would put that in the category. There are three misconceptions we can have about something like a legacy. It’s that idea of giving back and contributing. The common misconceptions I see, one, usually, I put it as the third example, but it’s the one you gave. It’s people who have taken advantage of other people to succeed.

They’ve trodden on people’s faces, acted without integrity, and then at some point, they get that sense of like, “I’ll use the power and money I have to atone for my sins and pretend I’m a good person.” That category, I’m not a fan of. There are also two other categories that people can accidentally fall into with legacy. One of them is around that aspect of they work hard to be a good person, but it’s based on what other people, society or others project onto them of what that looks like.

It’s not deeply informed by what they fulfilled to do or what they care about. It’s purely an outside-in approach to legacy, which is a tricky kind of place to be. The second category that people can fall into is a little bit like what I hinted at before with the doing good and making money. It’s this idea that they’ve swallowed without questioning the thought that legacy or contribution has to be completely about the other.

It has to just be generous and selfless, “I just give, and none of it is about me.” That leads to people falling into a bit of martyrdom and burnout because they end up feeling guilty. For example, they might have built a business, have a stack of cash because they’ve sold it and suddenly you see them talking about, “I’m going to give it all away. It has to be selfless.” There’s a discomfort with money and legacy. I see those three downsides of legacy all the time with people. That’s not what I’m talking about when I talk about legacy.

What is in your mind the ideal way for someone to be someone to make money and do good?

T comes back for it to be sustainable over time because the reality is that to create real change, you need to play a long game. If you think about the types of people who are running businesses, who have this kind of approach to life, they also are not going to just be sitting around. They don’t want to work for five years, earn a bunch of money and then sit around and do nothing. We’re going to have a long period that we are at work in the world.

The idea of a double-sided legacy where you say it needs to honor and respect you as an individual. We have to do the work to figure out what would be fulfilling for you. What does success look like for you as an individual? Not what others tell you it looks like because chances are, you’ve probably already ticked all those boxes and people think you’re successful, but you don’t necessarily feel fulfilled.

There’s the personal work around success and fulfillment and what a legacy is that’s uniquely yours, but we can’t just stop there or else we can fall into the category of thinking good intentions are good enough and it’s all about us. That’s not the case. The second part of that double-sided legacy is figuring out, from an impact point of view, what do you want to contribute to the world?

If your passion is about education or young people having opportunities from difficult backgrounds, how do we use that and have it as a common theme amongst all of the work that you’re doing and bring all those pieces together, but do that in a way that we have taken that approach I talked about before of running it to its logical end, reverse engineering, figuring out other things I’m contributing to, whether that’s in how I spend my time, my talent or versions of the old treasure piece whether it’s how I invest money or give money?

Is there a logical connection between all of those things that give me confidence that I am making a difference in the areas I care about? If we don’t know what that success point looks like, how we would know if we’d got there or whether we’re trending in the direction of that impact in the world, we can fall into that trap of, we hear a friend is doing a charity raising for this kind of topic. We go, “I’ve got some cash. I’ll give them cash.” That may not be aligned with what you’re trying to be part of. They would be the ways that I’d think about a double-sided legacy.


COGE 186 | Decision Cascade
Decision Cascade: Go back to the same framework. Use the conceptual leveling of saying which decision needs to come first and revisit it. When it changes, your decisions and behavior should change.


You would identify those three areas of time, talent, and treasure and then align those with an area that you have some interest in and that you have a passion for. If you are aligning your passion or your area of interest with your time, talent and treasure, you’re saying that’s where you’ll find that fulfillment that people are looking for. Thank you for that. How can people get in touch with you?

The two best ways to do that are to either go to my website, or if people want to listen a bit more and assess it out, I also have a podcast called Both/And with Bessi Graham.

Tell us a little bit more about what you do with businesses, so people know that in a little more clarity.

I’ve built a number of different businesses, but the main focus for me is around the coaching work I’m doing one-on-one and in group programs with high net worth individuals, ultra-high net worth individuals and established leaders, business owners who are at that crossroad where they’re saying, “I tick all the boxes. I look successful. I made it, but I’m not feeling that fulfillment.” My coaching work is to help people bring those different aspects of their life and work together and channel them effectively so that legacy is uniquely theirs and feels fulfilling.

If people want to get in touch with you regarding that, they can go to your Bessi Graham website.

Connect with me there.

I appreciate your time. You’ve been very generous. Thank you for the insights that you shared with us.

Thank you for reading my interview with Bessi. Before you jet off, I have a quick request. Please give the show a rating and reviews. This helps us to be seen across the interwebs. We have a 4.9 out of 5-star rating on Apple. Go over there. If you think we’ve earned a five-star, click that rating and then write a short review. If you don’t have Apple, but you have Spotify or Google, that’s fine as well. Take a couple of minutes. Give us that rating or review and share the show with other people. I appreciate your time. I look forward to catching you on the next episode.


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About Bessi Graham

COGE 186 | Decision Cascade

Bessi is tenacious and optimistic, a truth explorer who combines logical analysis with the courage to follow her intuition. Creating something from nothing and driving concept to delivery is her speciality. Identifying a person or organisation’s brilliance and helping draw it out brings her the greatest sense of satisfaction.

Bessi is the co-founder of Benefit Capital and The Difference Incubator (TDi).

As an investor, entrepreneur, business owner, company director, speaker and writer, Bessi’s passion for using business as an agent for change is internationally recognised.

For the past 20 years she has focused on unlocking capital to deliver positive social and environmental outcomes in Australia and the Pacific.

Recognised by the Australian Government with a ministerial appointment to the Committee for the Accelerating Commercialisation and Incubator Support Initiatives (Department of Industry, Innovation and Science); and advisory roles to the Department of Foreign Affairs and Trade (DFAT) for the Emerging Markets Impact Investment Fund (EMIIF) and Pacific RISE. Bessi was also the architect of the first investment readiness fund for the impact investment space in Australia – now run by Impact Investment Australia (IIA) as the Growth Grant.

Bessi has a background in management consulting and training, was a Teaching Fellow at the University of Melbourne, is a graduate of the Harvard Kennedy School and the Australian Institute of Company Directors. Bessi was a finalist in the 2017 Telstra Business Women’s Awards.

Where others shy away from difficult decisions, hard conversations and stepping into the unknown; Bessi is in her element when the stakes are high and her back is against the wall. When there’s a dragon to slay you want her on your team!