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The managers of development teams are in serious trouble! Since they are responsible for the people maintaining and enhancing an existing set of products and services, and possibly creating and developing new ones, enough people with the right skills are needed to get all these jobs done. Anything less will cause the team to collapse from being under-skilled or overworked. And they’re being squeezed hard to do more with less.

Management’s primary job is maintaining balance. It’s a business Zen thing, balancing the team getting tasks finished with low risk and low cost, while being organizationally accountable both upward and downward. Controlling this risk and trying to reduce it over time while positioning a team to keep moving forward despite the organization is a huge challenge, a serious and difficult task.

So just how can current and new work be completed with only the existing members of a team? A smart manager will grow the proficiency of the team members to get the work that needs doing done. The best way to make this happen is by enhancing the abilities of the members through a good skills acquisition process. Over a period of weeks a team can go from adequate to proficient, ready to face new challenges head on. And with a good plan for acquiring new skills, the team will become confident that anything can be accomplished.

In this first post of a multipart series, I discuss the ways that skills are acquired and how they can be used effectively.

How Skills are Acquired

A skill is an ability that may be acquired by a person. Skills are generally unknown until learned, though some level of proficiency may have been attained previously when learning a related or similar skill.

A smart manager must try to anticipate the skills a team needs to deliver assigned and anticipated projects. If there is a skill-gap — when there is a need for a person with a particular skill that is not available on the team — projects could be delayed, deadlines could be missed, good opportunities could be lost, and heads might even roll. Critical skill-gaps can stop a team or even a business in its tracks. Team members should have a high level of proficiency in as many required or anticipated skills as is reasonable.

It is hard work to ensure that team members acquire required skills. The principal ways to raise a member’s proficiency in a skill are through play, by listening to stories, through mentoring or apprenticeship, by taking classes or attending lectures, by pairing team members together, and by learning from external experts.


The most natural way to acquire and enhance skills is through play. It is one of the first self-initiated activities humans engage in after pure instinct, and from it the first skills are learned. In childhood, after socialization begins, play becomes more complex leading to the growth of other, more difficult skills. As people age, play feeds upon itself and the skill acquisition cycle keeps repeating with more and more complexity being mastered.

Play usually turns inward very early in life. Senses constantly pass in stimuli, and as it is absorbed by the sponges of the mind, the voices in our heads are constantly trying to rationalize the world. Play is what puts things in their mental places. Right and left brains play with each other as they develop, sometimes working together to reach common goals and sometimes at odds, roughhousing with each other.

Why are people’s personalities different? I conjecture that at the root it is because as people grow, their thinking assembles itself in different ways according to what gets into their heads and how well their two hemispheres play together. As play is at the root of learning, it is also at the root of how we become ourselves.

Play does not stop with childhood. It covers a very wide spectrum of human experience throughout a person’s life. Often the way a person first encounters a completely new concept is through hands-on experimentation or some kind of wordplay like a metaphor or an allegory, creating a small foothold where an upward climb can be started. Young or old, a little play can go a long way to ascend to very great heights of proficiency. And for some, acquiring skills through play is very rapid.

People who acquire skills by playing have their own learning biases. Some people need to physically do a thing to learn it and enhance their skills, playing outwardly. Others attain mastery inwardly by just thinking about how something is done, playing with things in their head. Play is an absolutely reasonable way to learn and acquire skills, just as valid as any formal learning technique.

But play is only one way. We all have experienced methods that transcend it.


One of these transcending methods is listening. The mind seems well-adapted to integrate knowledge by listening to a storyteller - the better the story and the teller, the more focussed is the listener, the more complete is the integration of information. And discussion of the stories? That is a mashup of listening and play.

Listening is not just about words. Parents often teach their young children life lessons by telling them stories with strong emphasis and emotion, sometimes acting out dialog in different voices, sometimes even accompanied by song when the learning must be deeply ingrained.

It may seem curious that dialog and music have such a large additional impact on learning for children, but at some time in their lives nearly everyone has experienced its power. It comes very naturally to most of us. Consider the game of telephone — transferring only words down a chain of people is quite difficult. Words can quickly become miscommunicated when translated through many sets of mouths and ears. Telling stories with dialog and singing stories to music expands learning into multiple mental channels, reinforcing lessons and more deeply embedding the communication.

As children age, learning through simple storytelling is augmented by learning to read and write. But the advent of reading and writing is relatively recent history. Before writing, knowledge was transferred by storytelling, and often the rules which governed practicing skills were set down in rhymes or songs that could be repeated while working. After writing, skills could be described and taught through reading - if the learner knew how to read. Up to just a few centuries ago, most people couldn’t. People learned about the world from those who could, and learned complex skills through apprenticeship.


Before reading became ubiquitous, almost all professions that required a high level of expertise were learned through apprenticeship. Typically over the course of many years, a master would raise up an apprentice, teaching skills only when the apprentice was ready (or worthy). Only when the master decided the apprentice was fully trained would mastery be acknowledged. It was a long-term, high-stakes game for both the master and the apprentice.

A master had work to deliver and a reputation to uphold, and could not afford a poor apprentice that could easily compromise the business. If the master were lucky, an unworthy apprentice would fail fast and a new one could be chosen to start the training. If the master weren’t so lucky, an apprentice might train for years before failure, and a lot of time would have been wasted. Some masters took on several apprentices at a time to try to insure some would be trainable without putting business at risk.

An apprentice had worries as well. A poor master might not pass along the skills needed to become competent in the profession. Years of training might be useless, and the apprentice might then be too old to pursue the same path under another master. There was also a possibility that the master might become unable to teach during the course of an apprenticeship because of old age, injury or death.

When a willing and able apprentice and a competent and well-skilled master found each other, both could become better and their skills could grow beyond what either could have done individually. This is the best that could be hoped for. But a master could only teach so many apprentices, and an apprentice could only learn so much from one master. Getting a well-rounded education was not possible through apprenticeship.


So being apprenticed to one master for many years was fundamentally flawed, especially as the number of new skills to learn began to grow more and more quickly. A master might be able to keep up with this growth in a small domain, but the tree of knowledge tends to cross-pollinate, and new skills were becoming needed that apprenticeship alone could not provide.

The solution to this problem was the basis for creating classes and schools. With classes, a master could expound on a subject to many apprentices at once, and an apprentice could learn from many different masters. Masters became professors or instructors or teachers and apprentices became scholars or pupils or students. People could choose the skills they wished to learn from acknowledged experts - the high stakes of apprenticeship were significantly reduced.

What’s more, since different professions required similar skills, the general skills for a whole set of professions could be taught incrementally by different teachers. Specialized skills could be taught to students by experts focused on a particular target. As new skills evolved, they could be added to a school’s curriculum. By taking classes, students targeting a profession could get all the skills they needed…


…up to a point.

Apprenticeship turns out new masters, but classes turn out partially-skilled graduates. Unless the graduate has interned with other professionals, it’s unlikely the classroom-acquired skills will be sufficient. It’s not that these graduates aren’t good; it’s just that they’re missing the seasoning they would have gotten through apprenticeship. They’re missing the tricks of the trade. To become masters, students need to gain real-world experience.

The solution for this problem is a kind of ad hoc apprenticeship. Professionals and graduates are placed into small groups - usually pairs - that work together and learn from each other. It’s not just the less-skilled gaining proficiency; the masters can keep their skills current through exposure to what the apprentices are bringing in.

In pairing, everyone is a teacher and everyone is a student.

Pairing has significant benefits for its members (and the team) when doing work, such as each keeping the other focused, the generation of ideas that neither would have thought of on their own, and the reduction of the thought-fatigue that comes so easily when a problem becomes frustrating. For these reasons, fortuitously, two people pairing produce more work than two people each working alone.

In almost every pairing situation, less- and more-skilled people are learning and getting better. Overall, this skill of the team is rising when pairs work together…

External Expertise

…up to a point.

Pairing is not enough. Even on a team whose members share skills freely with each other, even when new skills are introduced by the members, there will be skill-gaps. It’s unavoidable. The ever-growing world changes too quickly to keep up with every improvement, and some important, relevant ideas are bound to be missed.

Sometimes an expert from the outside must be brought in to help the team reach a raised bar. Specialists today are much as the masters from older days, highly-skilled and able to solve certain problems that nobody else on the team could handle as quickly or effectively. While these experts are often paid to come in and do a particular job, they should always be paired with team members so that their skills can be added to the team’s repertoire.

Leveraging the Ways of Skill Acquisition

While much of the previous discussion is a somewhat historically-based portrayal of learning skills, all of these methods of acquisition are still used today. A smart manager will recognize that not all people become proficient in the same way. Each may use different combinations and variations of these methods to acquire a particular skill. All acquisition methods should be available to whatever degree is appropriate to maximize the team’s skills.

In the modern development workplace, there are general do’s and don’ts with respect to acquiring skills.

Method How to use it effectively When not to use it
Play A percentage of regular worktime should be allotted each week and team members should be encouraged to use it to explore new areas of interest. They should be able to do this alone or with others. Recognition should be given for useful efforts. During hard deadlines or emergencies, play should be reduced or suspended. If the entire worklife is nothing but hard deadlines or critical emergencies, there are serious problems in the workplace, and they should be addressed quickly before burning out the team.
Listening Reading to keep aware of changes in the field should be mandatory. Lunch-and-learn sessions should be held regularly to share knowledge. Blogging is recommended for those who enjoy writing. Attending and possibly presenting at meetups and conferences should be encouraged. Spreading knowledge in the spirit of the storyteller helps both the listener and the presenter, or reader and author. It can lead to conversation, but it must be coherent. Controversial subjects or those that are not-safe-for-work must be avoided. Confidential topics need to stay in-house.
Apprenticeship Formal mentoring programs can be useful for fresh team members without much experience. Informal mentoring between any master and apprentice should be welcomed. Members who spend more than a small amount of their time mentoring clearly have a lot to give back to the team and should be recognized. An apprentice needs to be given an opportunity to use learned skills. Sometimes a master may just take over rather than allow an apprentice to fail and learn from mistakes. Care must be taken to keep the master and apprentice working together as a team, or neither will fully benefit. Balance is very important.
Classes Team members who benefit from learning in a physical or virtual classroom should take advantage of these opportunities. In some cases, a prescribed course of education may be required to hasten learning and mastery in specialized areas. Recognition should be given for all classes passed. Mandatory attendance at formal classes should never be the only option; there should always be coverage of a class available from notes or through a self-paced program. Some team members will push away from a classroom but go to every lecture on new topics that they can. Different Folks and strokes are the rule.
Pairing Pairing should be used whenever it is helpful (which in most situations is always.) However, it can be quite jarring for individuals who have not experienced pairing before. It all depends on how well team members communicate. Even if all else fails but the pair communicates well, some learning will happen by accident. Pairing is not a panacea, but it does help level-set the team. Some of the best pair-ers I’ve known tended to work most effectively by themselves, but they were experts with years of working alone behind them. A mix of some pairing and some individual effort often gives good results. Also switching pairs frequently can keep things fresh.
External Expertise Experts should be used when specialized skills are needed in a hurry, and there isn’t time for team members to acquire them. An expert should not be brought in without well-defined work and mutually agreed upon details of what is required for the work to be done. A team member should always pair with the expert to capture new skills. Experts have different agendas than the rest of the team. They are there to get the work done for the money, not to become part of the team. They should not be expected to act with the same interests as a team member does. If educating team members is desired, they should pair with the experts until a target level of proficiency is reached.

In today’s professional climate, no one can afford to stand still. Unless a job is simply getting work done without improving a team, acquiring and enhancing the skills of its members is a requirement, not an option.

The Difference Between Skill and Talent

Talent is a quality or ability that is inborn, rather than acquired. It can’t be taught. Though skills may be acquired by study, practice or training, generally a person without talent will never achieve the same level of ability as a person with it. You either have it or you don’t.

Talented people should consider themselves very fortunate. In their own particular way, they have a leg up on the rest of the world. But they should be careful they aren’t fooling themselves. Some talents require constant practice or else they peter out, and others have a limited lifetime no matter how much attention they are given. This is not saying that talent is not good; but a learned skill can be counted on while talent is less reliable. Acquiring a skill requires effort, even for a talented individual. They should serve themselves by acquiring skills rather than just counting on what they have to last forever.

If a person is not especially talented and must work harder to acquire a skill, they should not dismay. They’re in the majority, and they get to choose what to learn rather than be tied only to the skills that align with a talent. At the end of the day, if they’re investing the effort to acquire skills, they won’t have to worry. They are the ones that will be relied upon. People have more faith in a hard-earned skill than a special talent. Projects are accomplished by people with acquired skills.

To effectively execute a portfolio of projects, a smart manager must understand the difference between talent and skill. If the plan to deliver a project requires a talented individual rather than a skilled one, the manager had better have an ace up their sleeve. Talent is hard to find, harder to keep, and may not deliver. A manager should always try to plan for helping the team acquire skills. If talent is available, so much the better, but that bet shouldn’t be counted on without some hedging. Invariably, more skill is available than talent - and skill is what is needed to get jobs done.

Working Wisely

Sometimes the acquisition of skills should take a back seat to the work a team has been charged with. It isn’t always about learning, sometimes it’s more about finishing.

When given a job to do that has a short life, something that a less-skilled member would struggle with while someone skilled could finish quickly, there may not be a lot of impetus to focus on skill acquisition. This is especially true if the work is unlikely to be revisited in the near future. In this case, it’s probably better to just go ahead and have the skilled member do the work.

For a longer job, or one that will frequently recur, it is probably time to pair up team members and let them acquire skills. The member that is new to the system will benefit from the knowledge of the old hand, while the questions asked will typically give them both cause to dig into the work, with tricks and secrets being revealed and discussed, learning and reinforcement going hand-in-hand.

When two skilled members of a team are paired to work together, there won’t be a lot of subject-learning going on. Instead subtlety and nuance will be enhanced — skills related to getting work done generally. For skilled members, acquiring these broader skills is probably more important than task-oriented skills since they can be applied to completely new types of work.

When two lesser-skilled members are paired, it can become a real problem. Though they may reinforce each other, it can quickly degenerate into the blind leading the blind. If the subject is foreign to both, the work will proceed slowly. It may involve false starts, goose chases and rabbit holes, and in the end will have to be reviewed closely by skilled workers who may wonder which town these rubes rolled in from.

When experts are brought in, they should always be paired with team members, never isolated or permitted to be paired with each other — because if that happens, the skills that could have been acquired walk out the door when they’re done. It makes sense to pair an expert with a team member who already has skills in the subject being targeted so they can guide the expert through the way-we-do-things-here labyrinth. They can keep the focus on the real work that required someone from outside the group to come in and help with. The member will then have some new enhanced skills to share with the rest of the team and keep everyone’s skill sets growing.

A smart manager will pair members of the team carefully, according to these guidelines, trying to mix up the pairings to keep things fresh and grow camaraderie, while maximizing the speed of skill acquisition without compromising the quality of the work or its delivery to customers. The trick is in figuring out the pairing. I will discuss this in the next post of this series.


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Callibrity is a software consultancy specializing in software engineering, digital transformation, cloud strategy, and data-driven insights. Our national reach serves clients on their digital journey to solve complex problems and create innovative solutions for ever-changing business models. Our technology experience covers a diverse set of industries with a focus on middle-market and enterprise companies.