Leadership beyond deliberate practice

For a long time, the gurus and popular science literature have told us that the best way to master anything is by engaging in deliberate practice. Unfortunately, as I explain in The Myth of Deliberate Practice and Mastery, it’s not that straightforward. As I summarise below, deliberate practice works well in ‘kind’ learning environments but isn’t particularly effective in ‘wicked’ learning environments.

Now I want to double down on the usefulness of deliberate practice specifically as it relates to business and leadership. Can deliberate practice help you master these disciplines? It turns out that whilst it can be very helpful in the earlier stages of your leadership journey, it becomes less helpful as you advance in your executive career. That’s because of the ‘wicked’ nature and complexity of the learning environments that senior leaders operate in.

The problem with deliberate practice

Deliberate practice involves repetitive practice of challenging tasks, continuous feedback, and a structured effort to go beyond current abilities.

The term was first coined by Swedish psychologist K. Anders Ericsson as far back as 1993. Ericsson later wrote up more accessible pieces like The Making of an Expert (2007) for the Harvard Business Review, and an overview of his life’s work in his book Peak: Secrets From the New Science of Success (2016).

For a long time, deliberate practice has been the Gold Standard for honing expertise and mastery, but it has increasingly come under scrutiny. That’s because it only works well in ‘kind’ learning environments, which includes most sports, disciplines like chess, and subjects like learning languages or maths. In these environments, the rules of the game are fixed, the outcomes of actions are evident and feedback is fast and clear.

Deliberate practice doesn’t work well in ‘wicked’ learning environments, which don’t lend themselves well to rote teaching and practice and where the rules of the game aren’t fixed and might not be decided by you, learning is more challenging due to the dynamic, complex nature of the environment, contextual influences, and feedback is delayed, inaccurate, or misleading, often leading to persistent errors and misconceptions and making it hard to learn from actions.

Business strategy, business models and capital allocation, anything involving interpersonal dynamics (e.g. organizational design and culture), externalities (e.g. competitors), trading and investing, economics and Central Banking are all examples of wicked learning environments. Effectively, any sociotechnical system in which judgements and decision are made in relation to things about which the outcome won’t be known until well into the future is a wicked learning environment.

Deliberate practice relies on rapid feedback

A defining difference between kind and wicked learning environments is feedback, or rather the rate at which we receive it, its accuracy, or whether we receive it all.

If a tennis player serves the ball into the net, they know instantly that there’s a problem with their serve. If it keeps happening, the player can try and work out what they need to do to correct their serve by themself, they can ask their coach to observe them and make suggestions, or they can watch video feedback to try and pinpoint the problem. They can quickly understand what they’re doing wrong and try to correct it, repeating the process if the problem remains.

Someone learning to play chess against an experienced opponent will know very quickly that they have made a bad move because their opponent will quickly exploit the error and put the learner in a disadvantageous position. In addition to this tactical feedback, the more experienced opponent can also help the learner analyze the sequence of moves leading to their mistake, helping then identify and understand their errors and think about what move they should have made instead.

If you’re learning a new language, then you know that is underpinned by clear, rule-driven, learnable structures, including phonology (sounds), morphology (word formation), syntax (sentence structure), semantics (meaning), and pragmatics (contextual use). You know that the language has basic word orders of elements, like subject, verb, and object, and similar basic grammatical categories such as nouns and verbs. As you practice the new language, it’s quickly obvious that you don’t have the right vocabulary or are mispronouncing words because the listener will express their inability to understand what you are communicating. This quick feedback tells you that you need to try a new approach. Or there’ll give you more directive, supportive feedback to educate you on what to say instead. All of which make learning a new language a perfect ‘kind’ environment’ in which to apply the methodology of deliberate practice.

So, how does this type of learning roll over into business and leadership?

Deliberate practice in business & leadership: where it works

For anyone in the business or professional world looking for an effective approach to improvement, my basic advice is to look for one that follows the principles of deliberate practice: Does it push people to get outside their comfort zones and attempt to do things that are not easy for them? Does it offer immediate feedback on the performance and on what can be done to improve it? Have those who developed the approach identified the best performers in that particular area and determined what sets them apart from everyone else? Is the practice designed to develop the particular skills that experts in the field possess.
Peak: Secrets From the New Science of Success, by K. Anders Ericsson

Ericsson gives a very specific example of you can use deliberate practice to improve presentation skills:

The speaker chooses a particular skill to focus on during the presentation – telling engaging stories, for example, or speaking more extemporaneously and relying less on the PowerPoint slides – and then tries to make that particular improvement during the presentation. Meanwhile, the audience takes notes on how the presenter’s performance went, and afterward they practice giving feedback. If done just once, the presenter may get some useful advice, but it’s not clear how much difference it will make, as any improvement from such a one-off session is likely to be minor. However, if the company makes it a regular practice in all staff meetings, employees can steadily improve on various skills.

Any effective executive needs to have great presentation skills, and deliberate practice is a great way to learn this skill. I remember attending a two day course on presenting and public speaking when I was a new manager at Deloitte. We were taught the basics of where to stand, how to move and convey our voice. We learnt about glossophobia (the fear of public speaking), how some people feared public speaking more than death, and how we could help ourselves overcome these fears!

We were videoed presenting to our peers which meant that, as well as taking us outside our comfort zone, we got immediate feedback about how well we presented and what we could do to improve from both our peers and experienced facilitators.

Over time, I pushed myself to present to larger audiences and increasingly senior people. I incrementally shortened slides and speaking notes (until I had none). By continually nudging myself beyond my curent level of ability I became an increasingly confident and effective presenter and public speaker, just like the CEOs and leaders I admired.

Other examples of how deliberate practice can improve business & leadership skills

Giving feedback: proven feedback frameworks can be taught. Experienced trainers, facilitators and coaches can support learners as they roleplay and practice how to use the frameworks, providing immediate feedback on how to improve. Learners can commit to using the frameworks in weekly one-on-ones and feedback conversations.
Holding effective meetings: in the same way, established principles for holding effective meetings can be taught, rolepayed and later consistently practised. Learners can get feedback and suggestions about how to improve from colleagues who have been in meetings with them.
Decision-Making: like RAPID and RACI, there’s many decision-making frameworks that can be used to process important decisions. Experienced managers and mentors can provide quick feedback on how you choose and use any given framework. You’ll receive live feedback on the outcomes generated by the decisions the frameworks guided you towards. Consistent use of these frameworks for increasingly important decisions will help you hone your decision-making ability.
Financial Analysis: the principles of accounting are well defined and can be taught, supprted by professional qualifications. Regularly working on financial modeling and analysis, with guided reviews and corrections, will improve your ability to interpret financial data and make informed business decisions.
Programming – the integrated development environment or compiler will quickly flag errors if a programmer mistakenly writes an incorrect piece of code, often specifying the exact line and nature of the mistake. Automated testing frameworks and debugging tools will provide immediate feedback by running test cases and highlighting failures. The developer can ask experienced colleagues for advice if stillunsure. Feedback is swift and corrective, allowing the programmer to quickly identify and correct mistakes, and learn.

Deliberate practice in business & leadership: where it doesn’t work

“Generally speaking, no matter what you’re trying to do, you need feedback to identify exactly where and how you are falling short. Without feedback – either from yourself or from outside observers – you cannot figure out what you need to improve on or how close you are to achieving your goals”.
Peak: Secrets From the New Science of Success, by K. Anders Ericsson

The theme is clear: deliberate practice is contingent upon rapid feedback.

But what if you’re a senior leader navigating challenges that are devoid of rapid, plentiful feedback? Or, any feedback at all? Now you’re in a very different environment from the tennis or chess player, the person learning a new language, or to code, the employee wanting to improve their presentation skills, financial analysis or learning to hone their decision-making through frameworks. Now you’re in a wicked learning environment.

The world does not play fair. Instead of providing us with clear information that would enable us to ‘know’ better, it presents us with messy data that are random, incomplete, unrepresentative, ambiguous, inconsistent, unpalatable, or secondhand.
How We Know What Isn’t So, by Thomas Gilovich

Consider these examples from real client coaching conversations (names and some circumstances adjusted for anonymity):

Setting strategy

Nilash was the Executive Vice President of a business unit within a major financial services company. Reporting into the CEO and CPO, he was setting the strategy for the next year, and looking out towards the next five years. He literally had a PhD in Business Strategy, but now he was on the sharpend, both responsible and accountable for the strategy. His leadership position and reputation were at stake.

Yet he couldn’t begin to know whether the strategy for the next year was successful until at least after the year has passed. That’s a very long feedback loop. Even then, in such complex scenarios it’s often impossible to untangle the relationships between cause and effect. What’s more, one small input can lead to outsized outputs – you probably know this as the butterfly effect. So, even in hindsight, he would never be able to be completely sure whether it was his strategy that led to a successful outcome, or whether it was something else outside of his control (perhaps a main competitor went out of business?)

Add to this the global macroeconomic environment, with its complex interest rate movements, pricing and labour fluctuations, competitor dynamics etc, and you have a very different operating and prediction environment from the kind of stable, well-structured environments in which we’ve established deliberate practice works well.

Organisational restructuring & Culture

Although she had over 10 years working in scaling technology buisnesses, Suzanne was relatively new to the COO role. But the CEO was very confident in her ability, so had tasked her to lead the restructuring of the business. Product Management, Design and Engineering all used to report into the CTO. Now a new Chief Product Officer position had been created and a senior hire made. Product Management and Design would report into them and Engineering continue to report into the CTO.

Where should she start? Who needed to be moved where? What would the impact on the staff be? How would it impact the culture and how could she and the business manage that? Some people strongly oppose the restructure. How should she manage them? How would this impact other parts of the business? Who else did she need to involve? What’s the messaging? How long would the restructure take?

All these questions and more. It would be a long time until Suzanne knew the answer to these questions and much of it would be ambiguous and messy. How will she know if it has been a success? Can she even measure the impact on culture? With information coming in at her from all directions, in different forms and according to different timelines, it’s hard to see how deliberate practice was going to help her here.

Deciding whether to let a senior member of your team go

Alex was the cofounder of a 100 person VC-backed SaaS business. They had a gut feeling that they should fire their VP Engineering. Alex explained to me that the person was good at what they did but their approach was often too ‘corporate’. Sometimes their adherence to ‘best practice’ was beneficial in bringing order and process. Other times, it stifled the fast pace that the business needed to move at. Their personality was tricky, too. Half of their team really respect and value them. The other half don’t enjoy working with them. A couple of people have threatened to leave.

Already an effective communicator and good at giving radically candid feedback, Alex had sat down with the individual numerous times to explain the situation and the changes they would like to see, but was yet to see any real change in behaviour. What could Alex do? It wasn’t apparent how deliberate practice could help them crack this conundrum.