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8 reasons that building new skills is so hard

Summary

In the corporate world we often reach for training as silver bullet solution to performance problems. But building and practicing new skills is hard and if we don’t recognise the real-world difficulties people face, it’s likely that many skill-building initiatives will fail. In this article I discuss eight challenges we face when introducing new skills to co-workers.

  1. A shallow analysis of problems. This leads to a knee-jerk training program, which has limited impact.

  2. Taking managers’ and leaders’ word for what the root causes of performance issues are. Often the bosses have blindspots, which learning designers must uncover.

  3. Too many learning programs focus on knowledge and not skill. This leads to bloated design and unsatisfactory workplace outcomes.

  4. Without motivation and the right level of challenge many learners don’t gain value from training. Personalising the challenge and addressing motivation are design and leadership concerns.

  5. It’s hard to practice new skills when the status quo is to behave in old ways. Without social proof, people lack the confidence to practice their new-found skills.

  6. Often, leaders and bosses don’t embody the behaviour people have learned recently. This creates cognitive dissonance amongst learners.

  7. On teams, people don’t get praise for their new behaviours. Such muted responses can disincentivise follow ups from training programs.

  8. And last, without a critical mass of people who’re already skilled, you don't have enough role models to learn from. This too can slow down capability development.

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Readers of this blog may not know that back in the day, I worked in the learning and knowledge management space. When I joined Thoughtworks, I experienced what I later learned was the “impostor syndrome”. Most people I met, were more confident and skillful at their work than I was at mine. Or so it felt. Over the years, however, I’ve enjoyed sharing my skills with my colleagues. The things I know how to do well though, are merely a proxy for the time I’ve spent on task. I’ve made several embarrassing mistakes and experienced more pitfalls than I’d like to admit. The scar tissue from all these experiences makes me seem like a grizzled old veteran. Of course, it’ll be rather inefficient if everyone has to learn that way. So, it makes sense if someone like me can shorten that learning cycle for others. 

When Covid hit, we suddenly became open to reconsidering several presuppositions about learning. For example, did all effective, high-quality learning have to happen face-to-face? Well, even if we conceded that face-to-face, instructor-led experiences were the paragon of learning events, how much better were they than the alternatives? And if you were to balance cost and value, were you getting the most mileage for your time and money? Asking those hard questions allowed some of us to scale ourselves in ways that we’d ignored in the pre-Covid era. In the last few years, I’ve been able to touch hundreds (maybe thousands) of people inside and outside Thoughtworks with several skill-building initiatives I’ve been part of.

And yet, if I just glance around, I feel like a failure. Regardless of how many people I’ve trained on facilitation, I don’t see a lot of great facilitators around. It doesn’t matter how many people I taught storytelling. I still don’t see people embody a similar passion for crafting impactful narratives. Yet, people’s feedback on my training interventions has been top-notch. People show the confidence to apply the skills I teach them. They profess they can indeed take these skills to the workplace. But then they face the chasm between enjoyable training and workplace performance. I’ve puzzled over what creates this chasm, and I’d like to share my eight-part hypothesis with you. You’ll agree with some of the things I’ll write, and I expect you’ll disagree with others. Either way, my goal is to insinuate you enough to discuss this topic with me or someone else.

1. We wade in the shallows

As leaders, we love solutions we can take off the shelf and apply at scale. Often, when we see a performance problem on the ground, we associate it with a training solution. Let’s send 200 people to that workshop and we’ll sort things out. Sure, it could be an issue with knowledge and skills. Training could help with that. Not always, but we’ll come to that later. But what about when the problem’s with the process you follow, the resources people have, motivation or the lack of it or a rotten work environment? You can train the heck out of people, but it won’t solve the problems.

Training can address some performance problems but not all

The trap, however, is that discovering these root causes will require you to avoid your snap judgments and wade into deeper problem-solving waters. Each time you think training solves a performance problem, spend some time thinking about it. Ask yourself the five whys, draw a fishbone and understand the problem. If it still feels like the problem is knowledge or skills, let me tell you we’re still not out of the woods.

2. Inverse 80:20

Often middle managers or leaders trigger the conversation about a training intervention. Now these leaders have a bird’s eye view of most problems but they can’t always diagnose the issues at hand. On one hand, they may operate at a level of abstraction where they can’t relate to an average employee’s work. On the other hand, the root causes for some problems could lie with the leadership themselves. It’s only human to externalise problems and too often, leaders point out all the problems in the world except the ones they are accountable for. What if leadership contributes to 80% of the root causes? 

A wrong diagnosis of root causes can lead to failed skill-building efforts

What if, when we learn about performance problems, we can open up conversations with employees too? Not only does this help you build empathy with the potential consumers of any learning interventions you may introduce; but it also allows you to build a complete understanding of all the root causes of the problem at hand. Who knows — if you apply the 80:20 rule after such conversations, you may not need any learning interventions!

3. The curse of knowledge

For most of us, the most memorable experience of learning we have is from university. But in the academic world, the focus isn’t always on skills. It’s about building broad awareness and knowledge. And hey, that’s a good thing when learning calculus, but in the real world, people need to get things done. So yeah, it’s all nice and dandy to teach people about the Agile Manifesto, The Mythical Man-Month, and Alistair Cockburn’s paper on pair programming. When the rubber hits the road, though, people need to pair-program. They must learn “how-to” test drive their code in a red-green-refactor cycle. Of course, they need to be “aware” of the value of these methods, but that value becomes clear when it’s part of real-world, whole-task practice.

When working with learning designers, we must avoid telling them what people “need to know” and focus on what they “need to do”. Avoid the “how about that resource” and “what about that nice document” discussions. Stay focussed on the evidence - what will you observe in the real world that tells you that the training worked? Not only does that help you keep your learning partners accountable, but you’ll also have a lean program design that’s outcome-focused and not content-focused.

4. Motivation and autonomy

At the tail end of the book Atomic Habits, James Clear mentions the Goldilocks rule. He says, and I quote, 

“The Goldilocks Rule states that humans experience peak motivation when working on tasks that are right on the edge of their current abilities. Not too hard. Not too easy. Just right.”

Learning challenges should be “just right” - in the Goldilocks zone

Clear didn’t make up this theory. He borrows this concept from psychology research - the Yerkes-Dodson law says the same thing. Combine this with the now popular motivation theory from Dan Pink, where he calls out “autonomy, mastery and purpose” as the ingredients for motivation. Both theories raise a few questions about the people who we target with skill-building interventions.

  • Are we teaching people skills that fall within their “Goldilocks zones”? Anyone who finds these skills too easy or too difficult will disengage soon in the learning process.

  • Are people choosing to learn something because they want to achieve mastery of some skills? Or did someone just nominate them to learn?

  • Does this intervention solve a problem at hand and have a greater purpose? Or is it just academic from the learners’ perspective?

My questions are rhetorical enough that you know which side of the fence I’m sitting on. Where are you at?

5. Social proof comes in the way 

“We view an action as correct in a given situation, to the degree that we see others performing it.” - Robert Cialdini; Influence: The Psychology of Persuasion

Speaking of James Clear, he mentions a very interesting study called “Costly culture”, by Lunz, Sirianni, Mundry & Boesch. The study revealed that when a chimpanzee learns an effective way to crack nuts open as part of a certain group; if you switch that ape to a new group; it avoids using the superior nut-breaking technique only to conform to the new group. Isn’t that incredible? Think about the implications for your workplace. 

A bunch of people; let’s just assume from the pure passion of it; learn a set of new skills in an intervention you’ve rolled out. So far, so good. Now they go back to their workplace, where their close colleagues and the entire tribe are following the old, antiquated methods. How likely are they to stick out like sore thumbs? Especially when the skill is new to them. As Cavett Robert said, “95% of people are imitators and only 5% are initiators…”. Unless you’ve targeted the initiators, you are swimming against the tide. 

6. Leading by (lack of) example

Bosses often do their jobs with little or no training (© Scott Adams)

People derive influence from:

  • the close;

  • the majority;

  • and the “powerful”. 

In a company, leaders represent power. People model the behaviours of leaders at various levels. Often when you roll out programs to address performance issues, leaders become the blind spot. Ironically, they are also the most influential with behaviour change. 

Think about it this way. Let’s say you want to help people improve something simple - like doing meetings better. Sure, they’ll learn that they should have agendas, they should keep time in meetings, make visible notes and reconfirm actions before they close. Brilliant! So far, so good. What happens when they see their leaders set up meetings without agendas and ramble about whichever topic they fancy? How about when meetings end with no real clarity? How will your learners react when they see leaders normalise anti-patterns each day? I’ll leave you to estimate the impact of such influence. The point I’m trying to make, is that influencers and leaders matter if you want to change behaviour in the workplace. Otherwise brace yourselves for a long, uphill battle.

7. Muted success

If ineffective behaviours are the status quo, then anyone who’s learned new behaviour will most likely swim against the tide when they practise in the real world. Doing this off one’s motivation is difficult and often a short-lived adventure. Some years back, one of my recent client engagements, I noticed a Slack channel called #rockstars. Almost daily, someone praised a colleague for something incredible they were doing in their teams, for customers or the company. The engagement on this channel was also quite something. Not only did people at all levels appreciate their coworkers but the 🙌, 👍, 🏆, 🎊, and 🎉 emoji reactions were aplenty for every appreciation. It was a tiny acknowledgement, but I’m sure it went a long way for the people in question. I found this kind of open praise so effective, that I implemented it in every future team that I was part of.

Easy as it might be, we’re quicker to identify problems than we are to acknowledge positive contributions. When people face muted reactions for practising what they’ve learned recently, it reduces their motivation to stay consistent. Behaviour change is hard already. As I mentioned with “social proof”, most people tend to conform to the status quo. If someone sticks out like a sore thumb to do the right thing, they deserve some recognition, don’t they? If not, what’s the incentive? 

8. The need to seed practitioners

Continuing on the theme of social proof, there are two ways to make change. This’ll depend on the complexity of the skills you want to introduce. If it’s basic security awareness, you can expect that in a reasonable time frame, you can get most people to follow a certain set of guidelines. If it’s about learning complex skills though - for example facilitation, influence, solution selling - it can take years before you have a cohort of people that are skilled enough to be influencers in the workforce. 

As a corollary, it’s also likely that behavioural anti-patterns are so common in the workplace that they act as an opposing force to any skill-building initiative you launch. The complementary way of building critical mass is to hire people who already practice the skills you’re trying to teach. These are the people like Steve Martin above, who’ve perfected their craft day after day, for years on end. The sweet spot when building skills that take a long time to gain is to have the right mix of existing people who’ve been through a learning intervention and new people who already are skilled. Between the two, you can engineer enough social proof for the rest of the organisation to follow along. This won’t happen by accident. It must be part of a plan.


Those my friends, are the eight reasons (amongst many) I suppose, that come in the way of large-scale behaviour change in an organisation. We’ve been through the pandemic. Covid seems like a distant memory. Inevitably, many organisations have a “back-to-normal” approach to doing things and skill-building is no exception. But I hope we don’t discard the experiments and lessons from the pandemic in this rush for “normalcy”. A better world of work may indeed be possible.

We live in exceptional times. The current recessionary environment, coupled with the AI gold rush must be teaching companies how fast they must adopt new skills. After all, companies that won’t learn, won’t grow. So I hope this article provokes you to think about the shifts you may have to make, to drive a learning culture in your organisation. If you’d like to exchange ideas, let’s talk!