Ep 139: The Leadership Pipeline — Part 3: Enrolling People In Possibility

Are you looking to reinvent leadership for yourself and the organization and go from an industrial era kind of managerial approach to a transformational leadership approach? Create something beyond the existing paradigm and what that allows for as Adam Quiney continues where we left off in the previous episode. Here, he talks about the third step, Enrolling People in Possibility, and discusses what possibility is – everything outside of what already is and everything outside of what is predictable from the current paradigm in the context of transformational leadership. Adam then touches on the three things about the leader and talks about the importance of enrolling the leader first and keeping an open mind to possibilities before enrolling others.

Listen to the Episode Here:

The Leadership Pipeline — Part 3: Enrolling People In Possibility

Picking up from where we left off in the previous episode, which is about the second step of Leadership Pipeline: Recreating Trust, Adam will talk about the third step, which is Enrolling People in Possibility.

Welcome to this episode. This is a conversation in service of causing, developing, creating leadership in the moment, rather than conversations where you have something to say about leadership that you can regurgitate. You can pair it back. What I mean when I distinguish between a conversation that causes leadership and a conversation that’s about leadership or parroting. It would be the difference with someone telling you, “You need to lean out over your edge.” We’ve heard that a million times. It’s easy to tell people to lean out over your fear or even to talk about leaning out over your fear, but that’s talking about it.

What we’re interested in here are conversations that actually have you, or cause you, or those you lead to step into that lead in the moment. That would be rather than saying you need to lean out over your fear, it would be me stepping into my fear in the moment so that I can also stand for you to step into your fear. If I’m afraid that saying this bold thing is going to have you get upset with me. I’m worried about that, but I’m committed to something beyond my fear and feeling safe. That would be a moment where I can step into that fear, I can say the bold thing and I can be with whatever mess that gets created and I can clean it up afterwards. The intention of these conversations is to support you to step into the ladder rather than being yet another person parroting the words, the sentences and the statements of leadership. There are no breakthroughs down that path.

Where we’re going is part three of our series on The Leadership Pipeline, Enrolling People in Possibility. Just a reminder, as part of an ongoing series on the pipeline that leaders move through when they want to basically create a reinvention of the leadership for themselves and their organization. They want to go from an industrial era managerial approach to a transformational leadership approach. An approach where they’re creating something beyond the existing paradigm and what that allows for. We’re going to talk about that third step. As a reminder, the six steps in this pipeline are, one, the leader taken on their own work, two, creating trust, three, enrolling people in possibility, four, structure to support creating that possibility, five, committed action towards that possibility and six, addressing breakdowns. It can be helpful to think of this a little bit like a circle that feeds in on itself like Ouroboros rather than a straight line. The straight line leaves us in the illusion that like, “I took on my own work and now it’s done.” That’s never going to be the case. It’s a cycle.

Creating possibility is about creating what is currently impossible. Share on X

We’ll take on our own work. We’ll move through this stuff and then we’re going to find yourselves once again, stuck. The reason for that is that you will always have new blind spots. There’s always going to be new edges for you in terms of your own expression and your own leadership. The belief and the stories peddled about people being like, “I used to be afraid to talk to people, but now I never am ever.” That’s mythical. Typically, it’s a reflection of someone not so much having created a permanent forever breakthrough to end all time, but rather they’ve created a breakthrough in one area, but now they have stopped expanding beyond that. It may be true for them that they’re no longer afraid to speak to people ever, but that’s because they’re no longer pushing into the edges of their possibility, their leadership.


A cycle, not a straight line. Let’s begin by talking about what possibility is, what do we mean when we say that? Possibility encompasses everything that could be. In the context of this podcast and leadership, as I support, create, and work with, it’s everything outside of what already is and everything outside of what is predictable from our current paradigm. When I worked as a software developer and a project manager, I was very committed to working hard. Putting in a lot of time, that was something I was already comfortable doing. In fact, you could say that was my well-worn strategy. If things got hard, I knew that what there was to do was to double down the effort to work harder to grind. I might not like it, but I was capable of doing that. It wasn’t an impossibility for me. From there, me going to law school where there’s a lot of hard work and even harder work, working harder and longer hours than I’d been doing previously. That was not something I was already doing, but it was entirely inside the realm of what was predictable. It didn’t require a complete breakthrough from me. It just required that I do what I was already able to do, better, harder, faster, stronger.

You could think of this like a circle with a slice of pie. That slice of pie represents everything that’s inside your paradigm, everything that’s predictable, and then you can extend the edges of that pie out towards infinity and that would be like ever increasing stuff that you can do inside of what’s predictable. Everything outside of those edges is what we talk about when we talk about possibility. Everything outside of what already is and what already is predictable. Technically speaking, the broadest sense of possibility would include everything that you’re doing too, but we want to remove that so that we can move beyond that and have a different conversation.

If your organization is making $5 million in revenue annually, then the possibility would include everything beyond that, making $6 million, $10 million or $100 million by the end of the year. We’re going to contrast that here with predictability. Predictability for that company might be like, “We can increase our annual revenue by 10%.” They can edge out further or it might even be predictable for them to double their profits, but they would do so by doubling down the number of hours that their people make. This is why companies often don’t set goals like that because they’re like, “We don’t want to do crunch time.” That’s because they’re looking inside their pie slice, they’re looking inside of what’s already predictable. We could hit that goal, but then we would have to do this and we don’t want to do that. As opposed to the realm of possibility might include something like, “How could we double our profits without doubling the costs that we incur or the hours worked by our staff?” This would be entirely outside of their realm of predictability.

GL 139 | Enroll People In Possibility

Enroll People In Possibility: Getting people to lean out of what is known and into the realm of the seemingly impossible in the face of that incompletion can’t just happen.


Transformational Leadership

Bringing this back to leadership, Transformational Leadership is about breaking through the existing paradigms so as to create that which is outside of the predictable. So as to create that which is in the realm of possibility. A reminder here that there’s nothing wrong with staying inside the realm of the predictable. This tends to be more the realm of management and industrial age optimization. This is not a bad thing. If this is what you are aiming towards and you have buying an agreement on that from your leaders and those who you lead, then it’s perfectly fine. It’s nothing to say that transformation is better than optimization. Rather, what we’re doing here is distinguishing those two, allowing them both to be perfectly fine choices and then we have a conversation about transformation. We’re not making it wrong. If you’re like, “Look what we want to do here is not creating any breakdowns and just do this stuff better and faster, this conversation is probably going to be less interesting for you, but it doesn’t mean that it’s a better path.”

Ironically, creating possibility is about creating what is currently impossible. The work of transformational leadership is moving what is impossible into the realm of what you can now achieve. It’s impossible because the existing confines of the paradigm don’t allow for it, when I say your paradigm and all the collective beliefs, norms, etc. Here are few things that get in the way of this part of the leadership pipeline. We’ll lay these out here and speak to each of them and we’re going to talk about what there is to do. The three things we’re going talk about are first thing that gets in the way as the leader is not taken on the earlier steps. Indeed, this applies to every step along the pipeline, but it’s especially prevalent here. First, the leader has not taken on the earlier steps. Second, the leader does not have access to possibility themselves. They’re not able to hold or to stand in this possibility. Third, the leader expects their staff to accept what they’re putting in front of them simply. It’s like, “We’re going to do the impossible.” The staff were like, “What seems impossible?” The leader gets upset or frustrated because he’s like, “You should just accept this because I said so and I’m paying you.”

Without Earlier Steps

First, let’s look at that one where the leader is not taken on the earlier steps. When staff have had a breakdown in trust, they have very little capacity to look towards the future and even less capacity to look beyond the paradigm. The breakdowns in trust, they’re like hooks. They hook and keep those members of your staff stuck on the problems of the past. It’s a little bit like we could say, “Just let go of that, let’s go into the future.” That’s like imagining a child that’s fallen off his bike and really hurt himself and you say, “Just get back on the bike and don’t worry about it.” To a degree that would actually be cruel or even inhumane because the child has hurt themselves. A break down in trust might sound dramatic to talk about it like this, it has every bit of that same degree of impact.

For example, a leader who has said things in the past and not followed through on them or created breakdowns in trust some other way is not someone that people are going to be willing to buy into or even believe when they talk about creating the impossible. It’s hard enough to create the predictable on top of the problems of the past when they haven’t been cleaned up. Getting people to lean out of what is known, to lean out past that into the realm of the seemingly impossible in the face of that incompletion about the past, it just can’t happen.

Every leader faces discouragement and periods of losing sight of their own inspiration. Share on X

Often what happens is leaders aren’t really willing to fully own their impact. Often, when we reserved the right or stayed justified in ourselves like, “I did this because of how you were showing up.” Rather than taking full responsibility. It takes away the ability for that person over there to take complete responsibility because we are unwilling to do so, and then those hooks stay in place. From there, what ends up happening along this particular path is that the leaders were like, “We can do it, just let go of the past.” People will go along with that leader in words. They’ll say, “Let’s do it,” but they’re still holding onto the past.

They’re like, “This guy is so obnoxious, and if I agree, then he’s going to shut up and get out of my face and things aren’t going to change anyhow, so at least then I can get back to doing what I’m here to do, which is the job that I’m paid for.” What happens is you have the leader unable or unwilling to take responsibility and then you have the staff colluding with that in a way. They’re telling the leader what they need to know. You end up with this leader being like a desperate cheerleader. They’re trying to cheerlead over top of what’s actually happening and then get frustrated with their staff and resentful because things aren’t going the way they’re meant to. That’s the first barrier.

Don’t Have Practice

The second is that many leaders simply don’t have any practice or facility with standing in possibility themselves. They might get inspired about a vision, but then very quickly run into the wall that is created by their existing paradigm. If we’re going for doubling our profits, but not doubling our staff’s overhead, not doubling the number of hours our staff’s working, that’s great to be inspired about, but then there’s going to be this point where you start to like, “Okay, great. How do we make this happen?” And then very quickly, the leader runs into the wall of, “This is how it’s always been done. Here’s how we think about these problems,” smack.

If a leader doesn’t have much facility or ability to stand impossibility, meaning they can’t hold onto that vision for very long. As soon as they come up against a roadblock, it falls from their hands, then there’s absolutely no way that their team will be able to do so. If you, as leader can’t stay present to this possibility, if you can’t hold that it’s still possible, if you can’t find a way to believe in its possibility and you lose sight of that, then your staff have no hope. You are the one with the flashlight in front as you guys navigate this dark cave you’re in as you push into the unknown. To be clear, this doesn’t mean that it’s not okay for you to fall out of possibility. Meaning it’s okay for you as leader to lose sight of the fact that this could be created. Every leader face discouragement and periods of losing sight of their own inspiration.

GL 139 | Enroll People In Possibility

Enroll People In Possibility: As a leader, if you can’t stay present to this possibility and lose sight of that, then your staff have no hope.


Imagine Gandhi or Martin Luther King or Nelson Mandela, there were points where these people lost sight of the possibility that they were standing for. Possibilities that seemed absolutely impossible inside of the existing paradigm. As they sought to move forward and to actually create what they were seeking to create, they would have bumped up against the walls created by that paradigm. The leader’s job is to find their way back to possibility. In order to find your way back to possibility when you lose it, you first have to admit that’s happened. If you dogmatically insist, “I have not lost possibility. It’s still there.” Simultaneously, totally having lost access to that possibility, you’re screwed because you can’t see what’s happening to address that, and then you end up being a desperate cheerleader. “No, no, it’s all possible.”

Instead, the work here is to distinguish when you arrive here, “I can’t see this as possible anymore. I can’t stand in that possibility and invite my people to come over there and stand with me and then to build from that place.” What there is to do is to distinguish when you’re here and then get supported to recreate your vision for what is possible. Get supported by a coach, by a leader, someone who’s not on the court with you, who doesn’t stand inside your existing paradigm and can stand outside of it. As a side note, this is probably part of the limitations of groups like Vistage or EO, or other such groups where it’s like a group of CEOs or entrepreneurs come together and they’ve got this peer group, which feels good because you’re around your fellow peers. The trouble is they all exist inside the same paradigm that you do, which we could call life as CEO. What happens is, there’ll be like, “Oh my God, I’m trying to do this thing.” You know how it is like people are this way, and then the other people would be like, “I totally know how it is. Here’s how I solved that.”

Everyone is inside the same fishbowl. You’ve got people that aren’t inside your head, but they’re in the same fishbowl, which is why it’s quite beautiful to have a coach who, when you say, “You know how it is when you do this.” A powerful coach is going to begin that conversation by saying, “I don’t know how it is. Tell me why is it that way?” Begin to explore that with you and explore the limitations of the paradigm you’ve surrounded yourself in. That’s our second one, which is the leader can’t stand in possibility themselves.

Simply Buying Into Their Vision

Third, many leaders simply expect their team to buy into their own vision for what is possible and expect their teams not to fall out of a possibility themselves. This is most common when a leader is unable or unwilling to distinguish and see for themselves when they fallen out of possibility. The leader can’t accept that they themselves, have lost their inspiration. They’re back in the realm of what’s predictable and as a consequence, they’re unable to accept and thus to support their team when the same thing happens there. If you haven’t distinguished it and worked through it over here, you cannot help someone with it over there. Instead, what we have is a leader that will doggedly insists that their team, “Get back into that positive state of mind,” like a despairing cheerleader. The writing’s long been on the wall, the game is over, but they are unable and unwilling to stop their desperate cheers. This just doesn’t work. It ends up nagging their employees rather than inspiring them towards a new possibility.

In order to find your way back to possibility when you lose it, you first have to admit that that's happened. Share on X

The final piece of this would be leaders that are like, “They should go along with me because I’m paying them to.” That’s not how enrollment works. That’s how getting people to do something because you paid them works. Through payment, you can affect people’s actions, but not their state of mind. You could try to like, “I’m going to give you $1 million if you can change your state of mind and believe it’s possible to jump from here to the moon.” People will try to convince you of that, but money alone is not sufficient to create that shift. That requires getting connected, getting with your people, hearing their grievances and all of the reasons and supporting them through this. That’s all missing here.

Breakthrough Goal

Those are the three big things. One, the leader is not doing their work. Two, the leader has no facility to stay in possibility themselves or has fallen out of it and is unaware, or third that they expect their teams not to have any kind of breakdowns or to be able to do this cause I’m paying you. We’re not going to go too deep into how you enroll here. The long and skinny of it is that your job as a transformational leader at this point in the pipeline, is to enroll your people in possibility. What that means is first, you get enrolled yourself. You get present to what would be available if you were to create this result. You get present to how things would be different, to what would be possible from this place and then you enroll your team and what is possible in this. Remember that possibility exists in the land of breakthrough results. It’s outside of any predictable sets of results inside your existing paradigm. A breakthrough goal we’re setting is something that’s going to call our team forward and is not that it’s physically impossible, it’s that it’s impossible inside of the way that we view the world.

Once you are present to what could be possible, they’re like, “Oh my God, imagine this company.” You might need to share some of that with your employees. Like, “Here’s what I see as possible for us. This is the vision I have for us.” It requires some real vulnerability at this point. Like, “Look, I don’t know how to create this, but I know that we can do it. I believe in that possibility. I want to work with all of you and bring you on board to be the team that creates that as well. To do so, I need to know like what’s in the way for you. How do we make that happen?” These are the kinds of conversations that we’re having as opposed to. This is the goal, go and make that goal happen. Where the leaders are just bestowing something upon high. At this stage of the game, we’re about creating, enrolling ourselves and others impossibility. Not figuring out how to get there. That’s the next stage. The how comes on the other side of enrolling people in this work.

What people often do is declare their goal based on what they already know how they can achieve, which ensures that you will never achieve a goal outside of what you already know or know how to know. That means your goal is going to be limited when you look at “how” as the first thing within the paradigm. Possibility exists when we put ourselves in the what first, and then figure out the how on the backside of that. The “how” comes on the other side of enrolling people in this work. Are you enrolled in it? As a leader, are you clear in what you see would be possible if you, as a company and you, as a leader were able to create this kind of result? What would this provide you? What would this call forward from you? What would be different by virtue of having created this result? What would then be possible? These are the kinds of questions that get us present to possibility. Truly present to what could be hours for claiming and creating this kind of result even when we don’t know how to do it yet.

GL 139 | Enroll People In Possibility

Enroll People In Possibility: If you are not present to possibility, then it becomes very easy to fall out of it once you come up against the roadblocks in life.


A lot of us resist this because “We’re afraid I’m going to get excited and then I’m going to be let down, I’m going to get afraid and I’m going to make a declaration. I’m going to fail.” You have to fail if you want to succeed, there is no other way. Otherwise, you’re just repeating what you’ve already done. There are no breakthroughs in that. There is money for a time, but you will eventually go the way of Xerox or Kodak or these companies that weren’t able to innovate. If you are not present to possibility, then it becomes very easy to fall out of it once you come up against the roadblocks that will be in your way and it will become very difficult to enroll your other people in it.

Getting Enrolled

An absent, your own access to possibility is challenging to hold that space for people. The final step at this stage, first, you have to look on your side and get yourself enrolled. The final step is that you must enroll your people in possibility. Invite them to get present to the goal you’re setting in front of them. Initially, people will get blindsided and blocked by their inability to see how to create this. That’s okay, that comes afterwards. We’re never going to do it. We’re just addressing the order in which we approach these things. What comes next is inviting them to get present to what would be available to them if this goal were created.

What would be possible for you if we increased your revenue without increasing our hours? How would you feel? What might that call you forward into? You ask the same questions of them that you asked of yourself. Are people enrolled? Is there something in the way? If so, what? It’s important to recognize that enrolling people into possibility is asking them to trust you and themselves beyond their knowing. It’s also important to recognize that, unlike, “People should do this because I pay them.” Enrollment is co-created. You can’t force enrollment onto people, which is why so many leaders that try to, fail.

Enrollment is something that we create together. I have to sit down with you and say, “Look, there’s this bold vision I have for this company and I want to enroll you in it. Are you open to a conversation about that?” That with a conversation I have to say, “Look, there’s probably some stuff that we can see in the way, but here’s the vision I have for this company. What do you see for yourself in that? Are you willing to look with me? Can I support you in taking a look?” That’s how we enroll people in something. Enrolment in possibility is about moving outside of the range of what we already know so as to create something new.

You have to fail if you want to succeed. Otherwise, you're just repeating what you've already done. Share on X

The first thing is that there’s a lot to enrolling people in the possibility that we can’t cover here. This is about laying a pipeline for creating breakthrough results, rather than going into the nitty gritty of each step. I want to give you the general overview, the idea, but these conversations should not be a substitute for a coach or a leader who can support you with the actual details, the moments of this. The reason a podcast shouldn’t be a substitute for that is because leadership only exists in the moment. Anything I say is great if it applies perfectly to the moment that you’re in, but coaching and leadership meet you exactly where you are, right where you are. I want to be clear, you may be left with questions but how? I invite you to email those to me so that we can create episodes around them. That’s Pr@AdamQuiney.com. To acknowledge, that’s the limitations of this format.

The other thing I’ll say is that notice where you get stuck in this process of enrolling. If you want to become masterful at enrolling people in possibility, consider hiring a coach. The single greatest benefit that will provide you is to help you see the places where you are blocking possibility. Most people hire coaches and the coach is like, “Great. What do you want?” Their answers are so limited by what is possible inside their worldview. Right at the start of a coaching conversation of a coaching agreement, you’re going to start to break through those walls. Right at the beginning, you’re going to develop muscles and possibility and it might occur as challenging.

That’s everything we’ve got for you. That’s Step 3, enrolling people in possibility. Step 1, do your work. Step 2, recreating trust, airing your grievances. Step 3, enrolling people in possibility. Up next, we’ve got Step 4, which is creating a structure to support, creating that possibility. It’s important. It’s valuable this next step. All of these steps are valuable. I hope you’re enjoying this series. If you are, I would love to hear from you. It’s helpful to know whether this stuff’s having an impact because a lot of this conversation is one way. It’s one of the things that’s appealing to me about clubhouse as we get to be in an audio format as well, but it can be interactive. Anyhow, that’s everything that we’ve got for you. I hope you enjoyed this episode. We’ll talk to you next episode. Bye for now.

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About Adam Quiney

I’m an obsessive perfectionist, high-performer, former lawyer, and now an Executive Mentor. I know what it’s like to succeed easily and quickly. To blindly put my happiness in the hands of achievement.

All the success, money and possessions in the world couldn’t cure my boredom. Couldn’t produce a loving, intimate relationship with my wife…and definitely couldn’t fulfill me.