Deltas to the Global Maxima: Better Career Conversations

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As you likely already know, a key part of our role as engineering managers and leaders is to invest in the long term growth of our teams. In a previous article, we looked at how you should expect to push the improvement of your organization over time: you all learn, gain skills, and level up, both individually and collectively.

The resulting effect is a rising tide of organizational capability, or to borrow the name of a videogame mechanic, a power curve that should always be trending upwards: this year’s organization should be far more capable than last year’s. Everyone should be getting better as an expected part of their job. Staying the same is not good performance, it is stagnation.

Career Tracks: The Best of Intentions

As people follow the organization’s power curve, they progress in their roles and responsibilities. In order to bring order, fairness and uniformity to this progression, good organizations provide their staff with career tracks and progression paths. These are a matrix of expectations and capabilities that a member of staff maps to at a given moment in time. By looking at the matrix, they can see where they are, where they are going, and what they need to do to get there. Going up the career track is a sign of growth and development and typically comes with increased compensation and responsibility.

If you don’t have career tracks at your organization, then you can find lots of examples for inspiration on Legend says that the ones that I wrote for my previous company are still on there.

Career tracks are a great compass for people to navigate their progression. For example, it should be clear at which level of seniority a staff member gains the option to choose whether or not they want to make the transition to management. Typically this happens somewhere around the Senior Engineer or Staff Engineer level depending on the organization. It should also be clear when they should be expected to be the technical lead of complex projects, or to work across multiple teams, or to be the technical authority in a given domain.

However, career tracks are tools and not prescriptions. Not everyone’s progression is the same nor can that progression be distilled into linear checkboxes. And like many tools, they can be misused. In the hands of an inexperienced manager, they can become a crutch, encourage shortcuts and box-checking, and discourage long term thinking.

At best, career help staff know where they can go at a given company and provide some indicators of how they might get there. They help start a conversation. But, at worst, they can oversimplify and overgamify true growth and development, and contribute to increasing the disappointment frontier between staff and their managers.

Oversimplifications and Random Walks

So why is it that career tracks can be misused? The issue is that they are a simplification of a complex, multi-dimensional problem space. People’s careers can go in limitless directions, and career tracks are just one possible path at one possible company. They are represent a local maxima, not the global maxima.

People are different. One person may seek to run increasingly larger teams and organizations, continually pushing themselves outside their comfort zone, whilst another may thrive by running one team whilst still contributing technically, enabling them to continue to hone their craft.

Another person may want to stay at a certain level of technical contribution (e.g. Senior Engineer), but experience many different companies and problem domains over the years. Variety is important for them. Another may want to become a specialist and work on a single problem for their entire career; perhaps even at the same company. Here, depth is key.

Our final hypothetical person may just want to just make enough money, in whatever means possible, so they can stop working full time and concentrate more on their true hobbies and passions. Here, the end goal is not even career progression, but maximizing their gains toward financial independence.

Each of these people will want to walk different paths, and each of these paths will be unique to them.

Given that career tracks represent a local maxima of a single company and not the enumeration of the possibilities of an entire career, the problem hampering many manager-report relationships is that all coaching and personal development focus is limited to the next step on the ladder at the current company, and nothing beyond that.

Now, there is some good that can be attributed to a limited focus:

  • The next step on the career track is the most immediate and tangible goal, which means it is the easiest to make an actionable plan for.
  • No manager wants to lose a good report, so they will naturally gain by overindexing on pushing the next step at the current company.
  • Coaching people toward the bigger picture is hard, and requires a great deal of skill, time, and acceptance that their future may be in a different team or company altogether.

However, it can also lead to a number of problems:

  • If the next step is not available (e.g. there are no new teams for a budding manager to manage) then the report can become disillusioned. Despite increasing their skills and capabilities, they are not able to progress.
  • If the a company’s career ladder does not reflect an individual’s personal career goals, or does not present compelling nonlinear options, then the report may feel like they will limit their career growth regardless by staying at the company.
  • If career track levels directly map to compensation, then some companies may penalize those that rather wish to go deep or wide in their careers, rather than up. See the previous article on the Tarzan method for more on this.

So the question is: what do we do as managers in order to help our reports grow in a way that is meaningful to them, and not just to the company?

The Global Maxima

When we talk about career progression with our staff, we need to look beyond the career track and understand their unique longterm goals, desires, and motivations.

We need to stop obsessing over dangling the next step on the career track as a carrot. Doing so almost always leads to disappointment. Long term conversations become short term: why can’t I have that role now? When can I get that role? What’s the fastest way to get there? These are all questions that are focused on shortcuts and checking boxes, and not on doing impactful work for customers or increasing their skills.

Instead, we need to help our reports consider the bigger picture: what is the global maxima of their career?

This global maxima is the point at which we are at our most skilled, our most impactful, and the most satisfied. The global maxima may not even be a role, but a state of being where everything comes together: life, work, compensation, contribution, and happiness.

Try restarting your career conversations with your direct reports by asking them what this global maxima is for them.

Here are some primer questions. Try to get them to answer them in as much detail as possible, even down to where they’re waking up in the morning, what they’re looking at out of the window, and maybe what they’re eating for breakfast (toast is good):

  • If you think of yourself in the future as your most successful, happy or impactful, what exactly are you doing day to day?
  • Where are you doing it?
  • What are the skills that you have that make you so successful?
  • What are the problems that you are solving that make you so impactful?
  • What are the conditions that you are working in that make you so happy?
  • What are you doing outside of work that makes you fulfilled?

There are plenty of other questions that you could add to this: feel free to riff on them.

Now, it can be hard to answer these questions on the spot, so maybe you could give these questions as homework at the end of a one-on-one to think about before the next one.

In order to wrap some structure around this vision of the future, you’ll need to use a model. One potential model to use when doing this is of scope and impact which we previously covered.

  • 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, and the effectiveness of the decisions that you make. It is the quality of the sandcastles that you build.

Working backward from the global maxima, start defining scope and impact for each of the steps that you defined, and then calculate the delta between each of them. This should form a rough path that they may need to follow, which may be at the current company, or it may require future journeys at many others.

For example, if they want to be a VP Engineering at a top 5 technology company, what is the scope and impact of that role (e.g. organization size, projects, domain, budget, number of reports, etc.) and then what is the difference between the scope and impact of their current role? Subtract one from the other to see the gap.

It may be that the delta is vast (e.g. they want to run a 1000-person organization, but are currently running a 10-person team). If so, that initial delta will need breaking into incremental steps of career progression until they have a series of hypothetical roles that they could take that would get them to the global maxima.

For example, imagine you and your report are at a Series A company that is fundraising. This journey might involve:

  • Continuing to ride the wave of growth at your current company, and coaching them so they can take on their first manager of managers role after the next round of funding opens up a significant number of new teams.
  • Working with them to push them as far as you can within this new role, ensuring that they are able to experience as much of the scope and impact of future roles as possible.
  • If growth stagnates, helping them to use this experience as a springboard to work at a top technology even if it means taking a step back in terms of title and team size.
  • Performing well and seeking out opportunities to increase their scope and impact at the new company. Then, repeating these final two steps until they reach their global maxima.

With the delta defined between their current state and the next hypothetical step, you can get to work on identifying possible projects, roles, and skills that can be developed to close that gap.

  • What is possible in the current team, role and company?
  • What is impossible and must be achieved elsewhere?
  • How can you help them at least achieve what is maximally possible at your current company (think of defining a tour of duty, for example)?
  • How can you help them identify where the next vine swing in the Tarzan method might lie for them? This will also help with identifying and coaching their successors.

If you can work with your staff on decreasing the delta between where they are and where they want to go, then you are going far beyond the myopic focus on the next step on the career ladder. You are helping your staff to grow into the person that they want to be, and to develop the skills that they need to get there. It builds more trust, makes career conversations more meaningful and interesting for both of you, and whether your staff stay with you in the long term or not, they will be grateful for the time that you spent with them.

You are no longer the controller of a single step; you are a guide to a whole new world of possibilities.

Have a think about it. What’s your global career maxima? What are you doing this year to ensure you get there?

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.