The Disappointment Frontier

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I recently listened to Tim Ferris interviewing Claire Hughes Johnson, who, during her time at Stripe, wrote the excellent Scaling People: an actionable handbook for how to implement and run all of the administrative machinery that makes a company work. Check it out if you haven’t already.

During the interview she referenced a quote that I’d forgotten about until then, that: “leadership is disappointing people at a rate they can absorb“, which is typically attributed to Ronald Heifetz and Marty Linsky.

Well, that’s rather grim, isn’t it?

Yes. Is it true?


Disappointment is a fact of life. But maybe we can get better at managing it.

In the previous article we explored the Tarzan Method. It’s a way of adding more spontaneous play and surprise into your career journey. It’s relevant too: many of us are currently navigating our way through performance reviews and promotions as we hit the middle of the year, and career conversations in downturns can be tricky.

However, seasoned managers know that performance season is not all about progression and celebration. Instead, it is a time of the year rife with high expectations and consequently the potential for disappointment. It plays out in many ways. People don’t get the promotion they are after, or the pay increase they’ve been hoping for, or even the feedback or recognition that they feel they deserve.

Disappointment is the part of the performance process that leaves a lasting sour taste for managers and their staff, and it is particularly acute for top performers who can never quite get everything they desire, no matter how hard they work.

Sometimes you feel like you can’t win.

You Can’t Always Get What You Want

Managing a team of any size — from a handful of people to a whole company — is a continual balance between trying to empower people to achieve what they want (interesting projects, plentiful opportunities, a plethora of pay increases and promotions) whilst navigating a conflicting reality that doesn’t always want to give it to them.

As such, there is a lot of truth to the quote at the beginning of the article. Leadership is about disappointing people at a rate they can absorb.

In fact, I think that I’ve likely spent far more time on mitigation of disappointment or on managing expectations than I have on being motivational in my management career.

If you run a large team, there are so many zero-sum situations stemming from limited resources, strategic decisions, your customers, or the market that you can’t control.

For example:

  • You can’t always give someone the promotion they want because there isn’t a need for the role they want to move into. After all, there are only so many senior roles in a company. Not everyone can be a VP.
  • You can’t always give someone the pay increase they want because the company hasn’t made enough money to afford it, or it will make them a significant outlier compared to others. This has been especially true during the economic downturn of the last few years: cash is under close control.
  • You may not be able to prioritize new or innovative projects because you have to focus first on the less exciting but necessary ones. The reality of keeping your largest customers happy, or keeping the lights on, can be less exciting compared to the new and shiny things that your team wants to work on.
  • You may have to stop in-flight projects and reallocate staff because something more important has come up. With limited time and resources, a team (or many) may have to down tools on their current roadmap and pivot to something else. Of course, nobody likes this.

And the list goes on.

Working through each of these situations involves identifying, mitigating and managing disappointment. And you’ll already know that these situations happen all of the time.

Thus, it follows that managing disappointment is a core leadership skill, and it is typically overlooked when training new managers, despite them having to deal with it far more often than all of the more positive sides of leadership.

So how does disappointment get managed? And how can you get better at it?

Pop Goes The Frontier

Let’s think about how this disappointment grows and shrinks: introducing the disappointment frontier.

The disappointment frontier is the void formed from the mismatch between your team and reality. The larger the frontier, the more potential for disappointment when reality collides with it. Think of it like dynamite: the bigger the frontier, the bigger the explosion when it goes off.

The frontier can grow in size for a number of reasons:

  • You act as a buffer or protector of your team, shielding them from the reality of a situation. This can be because you don’t want to worry them, or because you don’t want to deal with the fallout of a difficult conversation.
  • You project an illusion of control over things that you can’t control in order to make your team trust you more, or even just to convince yourself things are more certain than they are. Good intentions, of course. However, this can lead to a rude awakening when reality hits.
  • You try to implement a team culture that is far removed from the rest of the company culture. This can be because you want to create a “safe space” for your team, or because you want to create a unique team identity. However, this can lead to a disconnect between how your team operates and how the rest of the company operates.
  • You overpromise on what you can deliver to your team. This can be because you want to motivate them, or because you want to keep them happy. However, this can lead to disappointment when you can’t deliver on your promises.

Keeping people and teams in a bubble of protection never ends well. It just delays the inevitable disappointment that will come when reality hits.

If you don’t proactively implement techniques that mitigate future disappointment, then the disappointment frontier will grow in size. Then, when an event happens that brings reality crashing down (for example, a promotion that can’t be given to your highest performer despite your full promise that it will), you’ll have a mess on your hands.

New leaders can sometimes make the disappointment frontier really big without realizing that they are doing it: in fact, they may think that they are doing a great job!

Here’s how they do it: they protect their team so they always work on what they want, they shield them from resourcing issues and discussions around their direction, and they promise them the world: pay, promotions, and never having to work on anything boring.

These leaders deliver roses upon roses, but they do so by hiding all of the poop under the carpet. This will always backfire in the end.

Reality will always meddle with your team’s desires and plans and you will have to coach them through it. But doing so with a small disappointment frontier is far easier than doing so with a large one.

Keeping The Frontier In Check

It turns out that by practicing the skills that you need to be a more effective manager, you can also reduce the size of the frontier. This is because managing disappointment is about increasing context adn managing expectations, and by doing so you bring reality closer to your team.


The first step is to overcommunicate everything that you can from your unique position at the top. You need to be transparent about what is going on in other teams, the wider company and with customers. This all forms context that helps the team make better decisions. There should be no surprises. Also, you also to be clear about what you can and can’t control amongst this, and what you can and can’t promise will happen.


Going back to our promotion example: if it is the case that promotions are reviewed by a committee and that committee has the final say (not you), then you have to make that clear to your team. It means you can’t promise anybody a promotion, but you can promise to advocate for them and to give them the best chance possible within the reality of the situation.

This behaviour shrinks the disappointment frontier because the member of staff is already aware that there is a chance that they won’t get the promotion, and they can subsequently prepare for that eventuality with your help.

Another example is when strategy changes call into question the direction of your team. Inexperienced managers may opt to shield their team from these discussions until they are finalized because they don’t want to worry them and distract them from their work.

However, this is a mistake: a skilled manager will be able to ensure that a team understands that priorities can change at any time, and that they always need to be ready to pivot within a context they already know about because you’re informing them.

This is a positive thing: being able to quickly change direction ensures that they are always spending their time on the most important work for the company.

Own It Or Be A Collaborator

This leads into the next key strategy: owning what you can control, and being a collaborator on what you can’t.

If you own a process or a decision, then be transparent that you do. Even if it might make you look like the bad guy. Don’t hide from it.

Even if people on your team disagree with your decision, they will appreciate that you are being honest and they can discuss it directly with you, which reduces disappointment quicker. (Compare the opposite: “the company has decided that…”)

For everything you don’t control, you can shrink the disappointment frontier by being a collaborator.

Going back to the promotion via committee example: you can’t control the committee’s decision, but you can collaborate with the candidate to put together the best promotion packet that you can, and vouch for them in the committee meeting. This way, there is no doubt that you are doing everything you can to help them get the promotion, and if they don’t get it, then you can continue this collaboration to help them understand why and what they can do to increase their chances next time around.

It allows you to be a partner rather than a barrier: disappointment won’t be directed at you, but at the situation instead. This is important, and keeps the disappointment frontier small: if it’s not in your control, then it’s not your fault.

Reality Check

If you lead a team, take a second to think about these questions:

  • What are the biggest recurring sources of disappointment for your team?
  • How big do you reckon their disappointment frontier is right now? What might you be shielding your team from or overpromising on?
  • How can you shrink the frontier? What can you do to manage expectations and bring reality closer to your team?
  • What can you do to be more of a collaborator on the things you can’t control?
  • Do you ever hide that you are the decision maker on something because you don’t want to be the bad guy? How can you be more transparent about this?
  • And, finally, what do you reckon the frontier size is between you and your own manager? How can you talk to them about it?

And remember: nobody is immune. Even CEOs can’t control and decide everything: they have to manage their own disappointment frontier with their board and their investors.

Overcommunication, transparency, and a clear delineation between what you can and can’t control will help you navigate the disappointment frontier bridging your team’s world and the external reality. It’s not your job to create a perfect utopia for your team. Instead, it’s your job to help them successfully navigate reality with you as their guide.

The Tarzan Method

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Performance review season always gets people thinking: where am I going? Where do I want to be next year? Why haven’t I managed to get that promotion this time around? What’s the point of all of this anyway?

How do we find answers? I am not an expert in your career. But I’ve been around enough to begin to see patterns, and sometimes being transfixed on a single goal can do more harm than good. Let’s dig into this a little bit.

The Fallacy of the Straight Line

Something that often throws people off is the idea that they need to doggedly progress in a straight line. For example, if someone had gotten to the point in their career where they were leading a team for the first time, they might look upwards and think that their ultimate goal is to find the shortest path to the top. See the diagram below:

This hypothetical person may believe that the game they are playing is about going from engineering manager to director to VP to CTO as quickly as possible, else they have failed in their quest. However, careers are long. A narrow focus on getting everything yesterday can be incredibly damaging to both their mental health and their ultimate destination.

A quest for self-actualization through becoming CTO before the age of 35 can lead to burnout, disillusionment, and a sense of failure. It may also lead to a lack of focus on the things that actually matter, such as building a portfolio of skills and experiences that will make them a better and wiser leader in the long run.

And get this: the path to increasingly senior roles is not something that you have complete control over. The upper echelons of leadership, which includes senior individual contributor roles also, are a function of the skills of the person that is doing them, combined with, most importantly, the fact that the given company needs someone to do that role at that time.

Sometimes companies just don’t need someone in that position. This can pan out in a number of ways. For example:

  • If you work for a small creative agency, it will likely never get to the scale where it will need middle management, let alone a CTO or dedicated principal engineer.
  • If you work for a large enterprise, it may have a rigid internal structure that doesn’t allow for the kind of lateral moves that you need to make to get the experience required to get to the top. You could wait your whole life for a promotion there.
  • If you work for a company that is in decline, it may not have the resources to promote you, even if you are the best person for the job; in fact, they may be trying to flatten the organization due to this period of austerity.

So, it’s often not you, it’s them. And that’s OK.

It is why it is so important to focus on what you can control, and let go of what you can’t. And it is also important to loosen your expectations of where exactly your career may end up, and instead focus on the journey that you are on right now, with a mindful eye on your general direction toward a future that makes you happy whilst developing a portfolio of skills and experiences that make you a better leader.

And it just turns out that there is an analogy that we can use to help us think about this: the Tarzan method.

Vine Swinging

New York City–based filmmaker Casey Neistat once answered a question about the nature of his own career progression with a neat analogy. It fits in well with having a more exploratory, playful, and joyful approach to your own career. In the video, to answer the question, he pulls out a big roll of paper from the wall and lays it across his table, and then proceeds to draw something similar to the diagram below:

On the left-hand side of the diagram is where you are right now in your career. On the right-hand side of the diagram are your current goals and aspirations, whatever they may be. The dotted line that is connecting the two is an idealized optimal shortest path that you could take to get from where you are to where you want to be.

However, the problem is that this direct path may not be possible, and it may not even exist. If your dream is to be the CTO of the biggest technology company in the world in twenty years time, which is a grand, respectable dream, then how do you even plan for that? It’s highly likely that this company doesn’t even exist yet, and the skills that you need to get there may be in a field that hasn’t even been invented.

Instead, you should think about your career like Tarzan swinging through the jungle. Tarzan starts at one tree and knows that he has an ultimate destination, but the path to get there isn’t immediately clear: there are hundreds of different trees that he could swing to. He doesn’t know which one is the right one at any given time. He just has to trust his instincts and his general sense of direction and then progress to the next vine, and then the next, and then the next. In the diagram, these vine swings are represented by the up and down line that eventually connects you to your goals.

As you swing from vine to vine, those leaps will take you along a path that is unique to you. Your first swing may take you off-course when you measure yourself against the dotted straight line, but it may also take you to a place that you never even knew existed. The same is true for the next swing, and the next swing. These new and unknown places are marked on the diagram as circles at the peaks and troughs of the swings. They may even be the most important places that you visit on your journey.

And here’s the neat thing: it’s likely at these most outward swings of each vine that you discover what really matters to you. You may find that you love a particular type of work, or a particular type of company, or a particular technology. You may find yourself trying a role that you hadn’t originally considered, or trying out working remotely, or moving to a different country. You may find that you love smaller start-ups rather than big enterprises, or perhaps the other way around. Who knows what you might find? That’s the beauty of the Tarzan method.

The Trajectory of Your Swing

The Tarzan method is a great way to think about your career progression metaphorically, but it doesn’t give you a lot of practical advice on how to actually get from one vine to the next. For that, we need to think about the trajectory of your swing. A heuristic can help here: scope and impact.

  • Scope is the breadth of your responsibility. It covers the size of the team that you manage, the size of the budget that you control, the number of projects that you are responsible for, and the number of people that you influence. It is the size of the sandbox that you play in.
  • Impact is the depth of your responsibility. It covers the result of the work that you produce, the output of your team, the effectiveness of the decisions that you make. It is the quality of the sandcastles that you build.

If you are thinking about your leadership career as a series of vine swings, then you can think about each swing as a progression in either scope or impact, or both. Ideally, when you zoom out at any point in your career, you can step back and observe that both have been trending upward over time.

In fact, we can plot the interplay between scope and impact as a quadrant, as shown below:

On the x-axis, we have impact, and on the y-axis, we have scope. Given your own internal measurement of your current scope and impact, you can work out which quadrant applies to you in your current situation and then think about which of them should guide you in your next vine swing.

Each part of the quadrant begins with the letter S, and they are, starting at the bottom left and progressing clockwise:

  • Stagnating: You have low impact and low scope compared to where you want to be. You are likely in a role that is not challenging you or satisfying you, and you are not making the impact that you want to make. Staying in this zone is not good in the long run. For you, it means that you are going to grow continually more dissatisfied with your work. It also becomes a vicious cycle: the less satisfied you are, the less you are likely to do good work, and the less opportunities that you are likely to get. You need to move out of this zone as soon as possible.
  • Stepping up: You are in a period where you are primarily focused on increasing your scope so that it can lead to a larger impact in the future. The ways that this can typically happen are by taking on more responsibility, such as by getting promoted, or by taking a vine swing to a different, often smaller, company that is offering a bigger role than you currently have. You can commonly see this happen when someone moves from a bigger company to a smaller company for a more senior role, such as a director of engineering at a public company moving to smaller private company as a VP of engineering.
  • Skyrocketing: This is where you are in a role that is both offering you a continued increase in both scope and impact. For example, you may be in a leadership role in a start-up that is growing extremely fast around you. When you’re in this position, the best move is to stay where you are and continue to grow with the company. This is the most desirable position to be in, but it is also the most rare.
  • Skilling up: This typically follows a stepping up period where you are primarily working on improving your performance and impact through learning new skills. This can be done by doubling-down where you are and investing in your own personal development, or by taking a smaller role at a bigger or more challenging company that will push you to learn new things.

The key to progressing in your career is to continually move around this quadrant between the top left and the bottom right, hoping that you get periods of time in the top right. The more that you can do this, the more that you will grow in your career. And, it goes without saying, you don’t want to be in the bottom left for too long.

So the question isn’t “how do I get to the top as quickly as possible?” but instead it should be “how do I maximize my chance of skyrocketing in the future?” Sometimes the answer to this question isn’t to take the most direct path, but instead to take the most interesting path. You never know what you might find.

Think about it over the next six months. What vine are you going to swing to next?