The Limits of Planning Poker

As an exercise, planning poker can be quite useful in instances where no prior method or process existed for estimating levels of effort. Problems arise when organizations don’t modify the process to suite the project, the composition of the team, or the organization.

The most common team composition for these these types of sizing efforts have involved technical areas – developers and UX designers – with less influence from strategists, instructional designers, quality assurance, and content developers. With a high degree for functional overlap, consensus on an estimated level of effort is easier to achieve.

As the estimating team begins to include more functional groups, the overlap decreases. This tends to increase the frequency of  back-and-forth between functional groups pressing for a different size (usually larger) based on their domain of expertise. This is good for group awareness of overall project scope, however, it can extend the time needed for consensus as individuals may feel the need to press for a larger size so as not to paint themselves into a commitment corner.

Additionally, when a more diverse set of functional groups are included in the estimation exercise, it become important to captured the size votes from the individual functional domains while driving the overall exercise based on the group consensus. Doing so means the organization can collect a more granular set of data useful for future sizing estimates by more accurately matching and comparing, for example, the technical vs support material vs. media development efforts between projects. This may also minimize the desire by some participants to press harder for any estimates padded to allow for risks from doubt and uncertainty, knowing that it will be captured somewhere.

Finally, when communicating estimates to clients or after the project has moved into active development, product owners and project managers can better unpack why a particular estimate was determined to be a particular size. While the overall project (or a component of the project) may have been given a score of 95 on a scale of 100, for example, a manager can look back on the vote and see that the development effort dominated the vote whereas content editors may have voted a size estimate of 40. This might also influence how manager negotiate timelines for (internal and external) resource requirements.


Photo by Aditya Chinchure on Unsplash

Accidental Social Capital and Status

 

I was made aware recently that I have accidentally acquired some interesting social status: I’m not on Facebook. Apparently, it isn’t just that I’m not on Facebook, its that I’ve never had a Facebook account. I’ve also never had accounts with:

  •  MySpace
  • Twitter
  • Instagram
  • TikTok
  • Pinterest
  • Snapchat
  • Reddit
  • Parler
  • The list goes on and on.

I am fairly active on LinkedIn and for a brief time had a Gab account after it first launched. The latter looked like another cesspool in the making so I deleted the account and moved on.

Acquiring this status wasn’t entirely accidental, even if it wasn’t by design. It was clear early on that the only way to win the race to the bottom of the social-on-line game was to not play at all. I’d seen this movie before. I had some experience with this environment in the pre-world-wide-web days of USENET newsgroups so it was pretty easy to see where this was heading. Thought I’d seen some epic flame wars on USENET but USENET newsgroups are to 21st century social media as camp fires are to nuclear explosions, as head colds are to social diseases.

I’m not so naive to think just because I don’t participate in the vast majority of social media that others haven’t contributed data about me without my knowledge or consent nor that I’m immune to the effects of social media. It’s that nuclear explosion thing. I can’t help but be aware of the blast and getting caught in the blast zone, even being targeted for the epicenter are known risks. While zillions of people are blithely working to feed The Beast’s insatiable need for data in exchange for nano hits of dopamine, my efforts are focused on how to avoid the growing tar pit that oozes from The Beast. I study how others have inadvertently been lured into the hot mess and, even more valuable, those few who have successfully wrestled themselves free.

Neither do I think social media is devoid of value or purpose. This is where LinkedIn (so far) seems to rise above the base rabble. There is a modicum of professionalism and elevated expectation of how one behaves on LinkedIn. (Although, I see signs of this eroding at an accelerated pace.)

As I see it, there is no way I can reliably cash in on this newly acquired social capital and status. It’s value is dubious. A small-talk starter at parties. A novelty. A non-thing that’s interesting like not having purple hair, tattoos, and a pierced face is interesting. To really leverage it, I’d have to jump into the social media quagmire, thereby emptying the account or, more likely, go into serious debt. In the end, carefully curated piles of garbage are still garbage.

So there it sits. A helluva thing, maybe valuable only as a note on my headstone.

Here rests Gregory Engel.
@nothing, @nowhere
He lived in the real world.

Teams, Tribes, and Community – 0.1.0

Several months ago, I made bold decision: Take command of the helm for a brilliant tribe of diverse creative thinkers dedicated to helping each other succeed. This is the first of an on-going series of posts – maybe once or twice a month – describing this evolving effort.

For an extrovert, this might not have been a bold decision. But in my case, you should know I designed the card that card-carrying introverts carry. So this decision involved a more thorough application of my already robust decision-making process. On a professional level, this may be the most significant challenge I’ve taken on to date. Will my years of experience with forming and guiding teams help this tribe further their success? Will I be able to find the gravitational force that holds us together and the spark that keeps us inspired? These are open questions. They are also questions that occupy much of my thinking.

We are not dedicated to achieving a single goal or moving in a unified direction. We each have our areas of expertise and independent business goals. We are much more a tribe than a team. As such, I believe we will be guided more by tribal dynamics and models than team rules and policies. The path is not clear, but this much I know…

  • There is no leader of this tribe. Not in the sense of a single person who’s responsible for setting the direction and making all the decisions that impact the organization. There is no “Chief” or “Czar” of anything. I’ll fill the role of Launch Commander and Flight Commander in order to get us organized and moving forward. However, I have been clear from the start about my intention to structure our tribe on principles of self-organization.
  • The emphasis is on simple and accessible technology and easy ways to organize meetings based on Agile principles and practices – lean coffee, for example, has served us well for our initial meetings. What has emerged since then are more involved and interactive meeting formats, such as client role-plays and accountability exercises. Keeping things simple and remaining mindful of barriers to participation is vital. Too many tools with too many logins risks the creation of a Tower of Babel. For now, the weekly video call is the center-point around which we all meet. This in itself is enough of a challenge given the global participation. Other than this, email is the acknowledged primary channel for asynchronous communication.
  • We are not accepting new members. Whether or for how long this remains the case is undecided. We have discussed various ways of introducing new members, but have decided to decide on this issue later. The circumstances that brought each of us together created a unique bond of trust and familiarity with each other’s business interests that makes the introduction of new members a risk to maintaining these relationships. At the moment, we are tipped slightly toward being on the large size and everyone acknowledges if we grow much bigger the meetings may become unmanageable and the interactions less valuable. Since trust is foundational, none of the details related to who we are and what we discuss will be revealed in this space. My writing will be limited to the general case of what I discover from having participated in and helped guide our tribe. It is my hope this may help others with forming and guiding their own teams and tribes.

Whatever the outcome, it’s been more fun thus far than I’ve had in a loooooong time.


Image by Youssef Jheir from Pixabay

Behind the Curtain: The Delivery Team Role

Even with the formalization of Agile practices into numerous frameworks and methodologies, I have to say not much has changed for the software developer or engineer with respect to how they get work done. I’m not referring to technology. The changes in what software developers and engineers use to get work done has been seismic. The biggest shift in the “how,” in my experience, is that what were once underground practices are now openly accepted and encouraged.

When I was coding full time, in the pre-Agile days and under the burden of CMM, we followed all the practices for documenting use cases, hammering out technical and functional specs, and laboriously talking through requirements. (I smile when I hear developers today complain about the burden of meetings under Scrum.) And when it came time to actually code, I and my fellow developers set the multiple binders of documentation aside and engaged in many then unnamed Agile practices. We mixed and matched use cases in a way that allowed for more efficient coding of larger functional components. We “huddled” each morning in the passage way to cube pods to discuss dependencies and brainstorm solutions to technical challenges. Each of these became more efficiently organized in Agile as backlog refinement and daily stand-ups. We had numerous other loose practices that were not described in tomes such as CMM.

But Agile delivery teams today are frequently composed of more than just technical functional domains. There may be non-technical expertise included as integral members of the team. Learning strategists, content editors, creative illustrators, and marketing experts may be part of the team, depending on the objectives of the project. Consequently, this represents a significant challenge to technical members of the team (i.e. software development and  tech QA) who are unused to working with non-technical team members. Twenty years ago a developer who might say “Leave me alone so I can code.” would have been viewed as a dedicated worker. Today, it’s a sign that the developer risks working in isolation and consequently delivering something that is mis-matched with the work being done by the rest of the team.

On an Agile delivery team, whether composed of a diverse set of functional domains or exclusively technical experts, individual team members need to be thinking of the larger picture and the impact of their work on that of their team mates and the overall work flow. They need to be much more attentive to market influences than in the past. The half-life of major versions, let along entire products, is such that most software products outside a special niche can’t survive without leveraging Agile principles and practices. Their knowledge must expand beyond just their functional domain. The extent to which they possess this knowledge is reflected in the day-to-day behaviors displayed by the team and it’s individuals.

  • Is everyone on the team sensitive and respectful of everyone else’s time? This means following through on commitments and promises, including agreed upon meeting start times. One person showing up five minutes late to a 15 minute stand-up has just missed out on a third of the meeting at least. If the team waits for everyone to show up before starting, the late individual has just squandered 5 minutes multiplied by the number of team mates. For a 6 member team, that’s a half hour. And if it happens every day, that’s 2.5 hours a week. It adds up quickly. Habitual late-comers are also signaling a lack of respect to other team members. They are implicitly saying “Me and my time is more important than anyone else on the team.” Unchecked, this quickly spills over into other areas of the team’s interactions. Enforcing an on-time rule like this is key to encouraging the personal discipline necessary to work effectively as a team. When a scrum master keeps the team in line with a few basic items like this, the larger discipline issues never seem to arise. As U.S. Army General Ann Dunwoody (ret.) succinctly points out in her book, never walk by a mistake. Doing so gives implicit acceptance for the transgression. Problems blossom from there, and it isn’t a pretty flower. (As a scrum master, I cannot “make” someone show up on time. But I can address the respect aspect of this issue by always starting on time. That way, late-comers stand out as late, not more important. Over time, this tends to correct the lateness issue as well.)
  • Everyone on the team must be capable of tracking a constantly evolving set of dependencies and knowing where their work fits within the flow. To whom will they be delivering work? From whom are they expecting completed work? The answer to these questions may not be a name on the immediate team. Scrum masters must periodically explicitly ask these questions if the connections aren’t coming out naturally during stand-ups. Developing this behavior is about coaching the team to look beyond the work on their desk and understand how they are connected to the larger effort. Software programmers seem to have a natural tendency to build walls around their work. Software engineers less so. And on teams with diverse functional groups it is important for both the scrum master and product owner to be watchful for when barriers appear for reasons that have more to due to lack of familiarity across functional domains than anything else.
  • Is the entire team actively and consistently engaged with identifying and writing stories?
  • Is the team capable and willing to cross domain boundaries and help? Are they interested in learning about other parts of the product and business?

Product owners and scrum masters need to be constantly scanning for these and other signs of disengagement as well as opportunities to connect cross functional needs.


Photo by Yu Hosoi on Unsplash

Achieving 10x

Crossed paths with an old but still relevant conversation thread on Slashdot asking “What practices impede developers’ productivity?” The conversation is in response to an excellent post by Steve McConnell addressing productivity variations among software developers and teams and the origin of “10x” – that is, the observation noted in the wild of “10-fold differences in productivity and quality between different programmers with the same levels of experience and also between different teams working within the same industries.”

The Slashdot conversation has two main themes, one focuses fundamentally on communication: “good” meetings, “bad” meetings, the time of day meetings are held, status reports by email – good, status reports by email – bad, interruptions for status reports, perceptions of productivity among non-technical coworkers and managers, unclear development goals, unclear development assignments, unclear deliverables, too much documentation, to little documentation, poor requirements.

A second theme in the conversation is reflected in what systems dynamics calls “shifting the burden”: individuals or departments that do not need to shoulder the financial burden of holding repetitively unproductive meetings involving developers, arrogant developers who believe they are beholding to none, the failure to run high quality meetings, code fast and leave thorough testing for QA, reliance on tools to track and enhance productivity (and then blaming them when they fail), and, again, poor requirements.

These are all legitimate problems. And considered as a whole, they defy strategic interventions to resolve. The better resolutions are more tactical in nature and rely on the quality of leadership experience in the management ranks. How good are they at 1) assessing the various levels of skill among their developers and 2) combining those skills to achieve a particular outcome? There is a strong tendency, particularly among managers with little or no development experience, to consider developers as a single complete package. That is, every developer should be able to write new code, maintain existing code (theirs and others), debug any code, test, and document. And as a consequence, developers should be interchangeable.

This is rarely the case. I can recall an instance where a developer, I’ll call him Dan, was transferred into a group for which I was the technical lead. The principle product for this group had reached maturity and as a consequence was beginning to become the dumping ground for developers who were not performing well on projects requiring new code solutions. Dan was one of these. He could barely write new code that ran consistently and reliably on his own development box. But what I discovered is that he had a tenacity and technical acuity for debugging existing code.

Dan excelled at this and thrived when this became the sole area of his involvement in the project. His confidence and respect among his peers grew as he developed a reputation for being able to ferret out particularly nasty bugs. Then management moved him back into code development where he began to slide backward. I don’t know what happened to him after that.

Most developers I’ve known have had the experience of working with a 10x developer, someone with a level of technical expertise and productivity that is undeniable, a complete package. I certainly have. I’ve also had the pleasure of managing several. Yet how many 10x specialists have gone underutilized because management was unable to correctly assess their skills and assign them tasks that match their skills?

Most of the communication issues and shifting the burden behaviors identified in the Slashdot conversation are symptomatic of management’s unrealistic expectations of relative skill levels among developers and their inability to assess and leverage the skills that exist within their teams.


Image by alan9187 from Pixabay

Agile Team Composition: Generalists versus Specialists

Estimating levels of effort for a set of tasks by a group of individuals well qualified to complete those tasks can efficiently and reliable be determined with a collaborative estimation process like planning poker. Such teams have a good measure of skill overlap. In the context of the problem set, each of the team members are generalist in the sense  it’s possible for any one team member to work on a variety of cross functional tasks during a sprint. Differences in preferred coding language among team members, for example, is less an issue when everyone understands advanced coding practices and the underlying architecture for the solution.

With a set of complimentary technical skills it’s is easier agree on work estimates. There are other benefits that flow from well-matched teams. A stable sprint velocity emerges much sooner. There is greater cross functional participation. And re-balancing the work load when “disruptors” occur – like vacations, illness, uncommon feature requests, etc. – is easier to coordinate.

Once the set of tasks starts to include items that fall outside the expertise of the group and the group begins to include cross functional team members, a process like planning poker becomes increasingly less reliable. The issue is the mismatch between relative scales of expertise. A content editor is likely to have very little insight into the effort required to modify a production database schema. Their estimation may be little more than a guess based on what they think it “should” be. Similarly for a coder faced with estimating the effort needed to translate 5,000 words of text from English to Latvian. Unless, of course, you have an English speaking coder on your team who speaks fluent Latvian.

These distinctions are easy to spot in project work. When knowledge and solution domains have a great deal of overlap, generalization allows for a lot of high quality collaboration. However, when an Agile team is formed to solve problems that do not have a purely technical solution, specialization rather than generalization has a greater influence on overall success. The risk is that with very little overlap specialized team expertise can result in either shallow solutions or wasteful speculation – waste that isn’t discovered until much later. Moreover, re-balancing the team becomes problematic and most often results in delays and missed commitments due to the limited ability for cross functional participation among team mates.

The challenge for teams where knowledge and solution domains have minimal overlap is to manage the specialized expertise domains in a way that is optimally useful, That is, reliable, predictable, and actionable. Success becomes increasingly dependent on how good an organization is at estimating levels of effort when the team is composed of specialists.

One approach I experimented with was to add a second dimension to the estimation: a weight factor to the estimator’s level of expertise relative to the nature of the card being considered. The idea is that with a weighted expertise factor calibrated to the problem and solution contexts, a more reliable velocity emerges over time. In practice, was difficult to implement. Teams spent valuable time challenging what the weighted factor should be and less experienced team members felt their opinion had been, quite literally, discounted.

The approach I’ve had the most success with on teams with diverse expertise is to have story cards sized by the individual assigned to complete the work. This still happens in a collaborative refinement or planning session so that other team members can contribute information that is often outside the perspective of the work assignee. Dependencies, past experience with similar work on other projects, missing acceptance criteria, or a refinement to the story card’s minimum viable product (MVP) definition are all examples of the kind of information team members have contributed. This invariably results in an adjustment to the overall level of effort estimate on the story card. It also has made details about the story card more explicit to the team in a way that a conversation focused on story point values doesn’t seem to achieve. The conversation shifts from “What are the points?” to “What’s the work needed to complete this story card?”

I’ve also observed that by focusing ownership of the estimate on the work assignee, accountability and transparency tend to increase. Potential blockers are surfaced sooner and team members communicate issues and dependencies more freely with each other. Of course, this isn’t always the case and in a future post I’ll explore aspects of team composition and dynamics that facilitate or prevent quality collaboration.


Image by Gerd Altmann from Pixabay

Relative Team Expertise and Story Sizing

In Parkinson’s Law of Triviality and Story Sizing, I touched on the issue of relative expertise among team members during collaborative efforts to size story cards. I’d like to expand on that idea by considering several types of team compositions.

Team 1 is a tight knit band of four software developers represented in Figure 1.

Figure 1 - Team 1
Figure 1 – Team 1

Their preferred domain and depth of experience is represented by the color and area of their respective circles. While they each have their own area of expertise, there is a significant overlap in common knowledge. All four of them understand the underlying architecture, common coding practices, and fundamental coding principles. Furthermore, there is a robust amount of inter-domain expertise. When needed, the HTML5/CSS developer can probably help out with JavaScript issues, for example. The probability of this team successfully working together to size the stories in the product backlog is high.

Team 1 represents a near-ideal team composition for a typical software related project. However, the real world isn’t so generous in it’s allocation of near-ideal, let alone ideal, teams. A typical team for a software related project is more likely to resemble Team 2, as represented in Figure 2.

Figure 2 - Team 2
Figure 2 – Team 2

In Team 2, the JavaScript developer is fresh out of college,  new to the company and new to the business. His real-world experience is limited so his circle of expertise is smaller relative to his teammates. The HTML5/CSS developer has been working for the company for 10 years and knows the business like the back of her hand. So she has a much wider view of how her work impacts the company and product development. As a team, there is much less overlap and options for helping each other through a sprint is diminished.  As for collaborative story sizing efforts, the HTML5/CSS and C# developers are likely to dominate the conversation while the JavaScript developer agrees with just about anything not JavaScript related.

As Agile practices become more ubiquitous in the business world, team composition beings to resemble Team 3, as shown in Figure 3.

Figure 3 - Team 3
Figure 3 – Team 3

The mix now includes non-technical people – content developers and editors, strategists, and designers. Even assuming an equal level of experience in their respective domains, the company, and the business environment, there is very little overlap. Arriving at a consensus during a story sizing exercise now becomes a significant challenge. But again, the real world isn’t even so kind as this. We are increasingly more likely to encounter teams that resemble Team 4 as shown in Figure 4.

Figure 4 - Team 4
Figure 4 – Team 4

As before, the relative circle of expertise among team members can vary quite a bit. When a team resembles the composition of Team 4, the software developers (HTML5/CSS and C#) will have trouble understanding what the Learning Strategist is asking for while the Learning Strategist may not understand why what he wants the software developers to deliver isn’t possible.

When I’ve attempted to facilitate story sizing sessions with teams that resemble Team 4 they either become quite contentious (and therefore time consuming) or team members that don’t have the expertise to understand a particular card simply accept the opinion of the stronger voices. Neither one of these situations is desirable.

To counteract these possibilities, I’ve found it much more effective to have the card assignee determine the card size (points and time estimate) and work to have the other team members ask questions about the work described on the card such that the assignee and the team better understand the context in which the card is positioned. The team members that lack domain expertise, it turns out, are in a good position to help craft good acceptance criteria.

  • Who will consume the work product that results from the card? (dependencies)
  • What cards need to be completed before a particular card can be worked on? (dependencies)
  • Is everything known about what a particular card needs before it can be completed? (dependencies, discovery, exploration)

At the end of a brief conversation where the entire team is working to evaluate the card for anything other than level of effort (time) and complexity (points), it is not uncommon for the assignee to reconsider their sizing, break the card into multiple cards, or determine the card shouldn’t be included in the sprint backlog. In short, it ends up being a much more productive conversation if teammates aren’t haggling over point distinctions or passively accepting what more experienced teammates are advocating. The benefit to the product owner is that they now have additional information that will undoubtedly influence the product backlog prioritization.

False Barriers to Implementing Scrum – II

In a previous post, I described several barriers to implementing scrum. Recently, an additional example came to light similar to the mistake of elevating scrum or Agile to a philosophy.

In a conversation with a colleague, we were exploring ways on how we might drive interest for browsing the growing wealth of Agile related information being added to the company wiki.  It’s an impressive collection of experiences of how other teams have solved a wide array of interesting problems using Agile principles and practices. Knowing that we cannot personally attend to every need on every project team, we were talking through various ways to develop the capacity for exploration and self-education. I think I must have used the phrase “the information is out there and readily available” a couple of times to many because my colleague reacted to where I put the bar by comparing learning Agile to surgery.

Using the surgery metaphor, she pressed the comparison that all the information she needs about surgery is “out there and readily available” but even if she knew all that information she likely wouldn’t be a good surgeon. Fair point that experience and practice are important. And if that is the case, then everyone should be taking every opportunity they can to practice good agile rather than regressing to old habits.

More importantly, perhaps, is the misapplied metaphor. Practicing agile isn’t as complicated as surgery or rocket science or any other such endeavor that requires years of deep study and practice. Comparing it to something like that places the prospects of doing well in a short amount of time mentally beyond the reach of any potential practitioners.

Perhaps a better metaphor is the opening of a new rail line in the city. A good measure of effort needs to be expended to educate the public on the line’s availability, the schedules, how to purchase fares, where the connections are, what are the safety features, etc. Having done that, having “put the information out there where it is generally available,” it is a reasonable expectation that the public will make the effort to find it when they need it. It is unreasonable, and unscaleable, to build such a system and then expect that every passenger will be personally escorted from their front door to their seat on the train.

It is also interesting to consider what this does to the “empathy scale” when such an overextended metaphor is applied to efforts such as learning to practice Agile. If we frame learning Agile as similar to surgery then as people work to implement Agile are we more inclined to have an excessive amount of empathy for their struggles and be more accepting or accommodating of their short comings?

“Not to worry that you still don’t have a well formed product backlog. This is like surgery, after all.”

Are we as an organization and each of our employees better served by the application of a more appropriate metaphor, one that matches the skill and expectations of the task?

“We’ve provided instruction as to what a product backlog is and how to create one. We’ve guided you as you’ve practiced refining a product backlog. You know where to find suggestions for improving your skills for product backlog stewardship (wiki, books, colleagues, etc). Now role up your sleeves and do the work.”

Successful coaching for developing the ability in team members for actively seeking answers requires skillfully letting them struggle and fail in recoverable ways. It is possible to hold their hand too long. To use another metaphor, provide whatever guidance and instruction you need to so they know how to fish, then let them alone to practice casting their own line.


Photo credit: langll

Friends, Guides, Coaches, and Mentors

The “conscious competence” model for learning is fairly well known. If not explicitly, than at least implicitly. Most people can recognize when someone is operating at a level of unconscious incompetence even if they can’t quite put their finger on why it is such a person makes the decisions they do. Recognizing when we ourselves are at the level of unconscious incompetence is a bit more problematic.

A robust suite of cognitive biases that normally help us navigate an increasingly complex world seem to conspire against us and keep us in the dark about our own shortcomings and weaknesses. Confirmation bias, selective perception, the observer bias, the availability heuristic, the Ostrich effect, the spotlight effect and many others all help us zero in on the shiny objects that confirm and support our existing memories and beliefs. Each of these tissue-thin cognitive biases layer up to form a dense curtain, perhaps even an impenetrable wall, between the feedback the world is sending and our ability to receive the information.

There is a direct relationship between the density of the barrier and the amount of energy needed to drive the feedback through the barrier. People who are introspective as well as receptive to external feedback generally do quite well when seeking to improve their competencies. For those with a dense barrier it may require an intense experience to deliver the message that there are things about themselves that need to change. For some a poorly received business presentation may be enough to send them on their way to finding out how to do better next time. For others it may take being passed over for a promotion. Still others may not get the message until they’ve been fired from their job.

However it happens, if you’ve received the message that there are some changes you’d like to make in your life and it’s time to do the work, an important question to ask yourself is “Am I searching for something or am I lost?”

If you are searching for something, the answer may be found in a conversation over coffee with a friend or peer who has demonstrated they know what you want to know. It may be that what you’re looking for – improve your presentation skills, for example – requires a deeper dive into a set of skills and it makes sense to find a guide to help you. Perhaps this involves taking a class or hiring a tutor.

If you are lost you’ll want to find someone with a much deeper set of skills, experience, and wisdom. A first time promotion into a management position is a frequent event that either exposes someone’s unconscious incompetence (i.e. the Peter Principle) or challenges someone to double their efforts at acquiring the skills to successfully manage people. Finding a coach or a mentor is the better approach to developing the necessary competencies for success when the stakes are higher and the consequences when failing are greater.

A couple of examples may help.

When I was first learning to program PCs I read many programming books cover to cover. It was a new world for me and I had very little sense of the terrain or what I was really interested in doing. So I studied everything. Over time I became more selective of the books I bought or read. Eventually, I stopped buying books altogether because there was often just a single chapter of interest. By the time I concluded my software development career, it had been many years since I last picked up a software development book. This was a progression from being lost at the start – when I needed coaches and mentors in the form of books and experienced software developers – to needing simple guidance from articles and peers and eventually to needing little more than a hint or two for the majority of my software development career.

A more recent example is an emergent need to learn photography – something I don’t particular enjoy. Yet for pragmatic reasons, it’s become worth my time to learn how to take a particular kind of photograph. I needed a coach or a mentor because this was entirely new territory for me. So I hired a professional photographer with an established reputation for taking the type of photograph I’m interesting in. My photography coach is teaching me what I need to know. (He is teaching me how to fish, in other words, rather then me paying him for a fish every time I need one.)

Unlike the experience of learning how to program – where I really didn’t know what I wanted to do – my goal with photography is very specific. The difference had a significant influence on who I choose as guides and mentors. For software development, I sought out everyone and anyone who knew more than I. For photography, I sought a very specific set of skills. I didn’t want to sit through hours of classes learning how to take pictures of barn owls 1,000 meters away in the dark. I didn’t want to suffer through a droning lecture on the history of camera shutters. Except in a very roundabout way, none of this serves my goal for learning how to use a camera for a very specific purpose.

Depending on what type of learner you are, working with a mentor who really, really knows their craft about a specific subject you want to learn can be immensely more satisfying and enjoyable. Also, less expensive and time consuming. If it expands into something more, than great. With this approach you will have the opportunity to discover a greater interest without a lot of upfront investment in time and money.

Layoffs

I’ve never been fired, but have been laid off three times over the course of four distinct careers. I’m also three-for-three for having landed in a much better place after having been laid off. So with three data points, maybe there is some truth to the street wisdom that a little adversity is a good thing.

“I judge you unfortunate because you have never lived through misfortune. You have passed through life without an opponent- no one can ever know what you are capable of, not even you.” – Seneca, On Providence, 4.3

I have also survived 17 layoffs. And I remember them all.

Paradoxically, many of the layoffs I survived were more painful than the layoffs in which I was included. I have clear memories of people I enjoyed working with that one day were simply gone from the place I was spending more than one third of my life. The resulting crash of morale at the workplace simply added to the sense of dread and “why bother” attitude. Their absence became a reminder that we were all living under someone else’s Sword of Damocles, that we would pay the price of poor decisions made by someone else. In some instances, the nauseatingly smug expression of schadenfreude by a few well-connected corporate parasites and toxic individuals cruising the corridors just added to the sting. It doesn’t seem this is easier to deal with by those that remain after a layoff in a distributed work environment.

To say I’ve “survived” all the layoffs that occurred throughout my multiple careers, whether I was culled or not, is more than a little melodramatic. I have truly survived much, much greater losses. Layoffs are not lethal events and living according to several key Stoic principles has helped me to persevere and gain strength from the brief storms of finding work.

“To bear trials with a calm mind robs misfortune of its strength and burden.” – Seneca, Hercules Oetaeus, 231232

Reflecting on work transition experiences, I wondered what is it about having been laid off that made the next place so much better.

I have always worked hard to add value to my employer’s business. If that value was either not appreciated or the business shifted away from needing the value I was capable and willing to provide, it was a clear sign that it’s time to move on. By making this a choice, I could leave with no hard feelings and no burned bridges. Psychologically, this is more intimidating but much healthier.

Seeing the positive side of being laid off can be a little more difficult, particularly if one has been blind to the signs that every company and manager broadcasts when a layoff is eminent and is surprised when they happen. For starters, layoffs erased all the baggage I was carrying that belonged to the employer and made it much easier to strike out in a direction that suited my interests, skills, talents, and goals. Each of the three layoffs launched new, more lucrative and rewarding careers.

“Today I escaped from the crush of circumstances, or better put, I threw them out, for the crush wasn’t from outside me but in my own assumptions.” – Marcus Aurelius, Meditations, 9.13

Switching employers, even careers, more frequently than previous generations is a good career development strategy. In the dot com era, it was the only effective way to find meaningful raises and career advancement. Why toil away for a decade under Management-by-Taylorism to scratch out incremental pay increases when a salary could be increased by 10%-20% just by switching employers? Twenty-five years on, staying with the same employer for more than five years actually looks odd to many recruiters I’ve been talking to.

A friend of mine has a personal policy to commit to an employer for 1,000 days. At that point, she decides if the workplace it meeting her goals and expectations. Doesn’t matter if it’s a shortcoming of her employer or if her goals and interests have changed – a mismatch is a mismatch so it’s time to leave. I think it’s a good policy, particularly in the Age of Information and Knowledge and distributed workforces.

A policy like this builds resilience in several ways.

1. It’s important to know what it takes to persevere with the crap work that goes with just about any job. Flitting from job to job doesn’t develop this. A 1,000 day commitment is enough to show that you made it past the “honeymoon” period every job has, have worked more than a few significant problems into solutions, and generally paid your dues and demonstrated – if only to yourself – you have the chops to do the work.
2. Deciding to leave a job and doing so multiple times throughout your life builds confidence in your abilities to create your future.
3. It adds a valuable layer to your talent stack, as Scott Adams has described it.

If it was generally known that employees had this policy, employers might expand their efforts to foster cultures that allow employees who are creative and collaborative to thrive and grow. Instead of what’s more common: Cube farms propped up by career leaches that brag about having worked at the company for 25 years when in fact all they’ve done is worked one mediocre year and repeated it 24 times.

I’m done with that. Forever.

“There are those too who suffer not from moral steadfastness but from inertia, and so lack the fickleness to live as they wish, and just live as they have begun.” – Seneca, On Tranquility of Mind


Photo by Benmar Schmidhuber on Unsplash