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.


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