• Toby Sinclair

Curated Insights | Organisational Change

Updated: Jan 14

Curated Insights for Organisational Change

Start here to learn more about these Curated Insights.

This collection of insights is focused on how to change organisations.

Over the last decade, I've worked as a coach in organisations big and small. During this time there have been several 'ah-ha' moments, insights that have shifted my perspective and led to breakthroughs. The insights are described in my words with attribution to the thinker who helped inspire it.

People who inspired these organisational change insights include:

and many more....

Where a person has influenced an insight their name is referenced [Name]. An emoji also indicates the medium where you can source the relevant knowledge.


55 insights are grouped into the following sections:

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Organisational Design

I have come to learn that:

#1 - Organisations cannot be "designed" up-front. Instead, you should focus on the conditions that enable a new design to emerge

[Dave Snowden] 📝

#2 - Organizations are implicitly optimized to avoid changing the status quo middle- and first-level manager and “specialist” positions & power structures. Therefore, don't be surprised when the system pushes back to any changes that threaten the status quo. Also, don't be surprised despite your best efforts if the system ends back up where it started

[Craig Larman] 📝

#3 Organisations are complex, adaptive organisms, rather than mechanistic and linear systems. This means you should change through rapid experimentation rather than big up-front designs. And any attempt to change the organisation may lead to surprising results.

[Naomi Stanford (via Team Topologies)] 📚

#4 Organisations are 'Sociotechnical Systems'. The interaction of social and technical factors creates the conditions for successful (or unsuccessful) organizational performance. As such, when exploring change explore the relationships between the technical and social system. - [Nick Tune] 🎬

#5 The purpose of a system is what it does (POSIWID). Therefore, if the system is working in what you think are ineffective ways, it's likely that is by design. The system will be meeting the needs of some people. Don't ignore this fact and trace what needs the existing system is meeting before trying to change it.

[Stanford Beer] 📝

#6 You need to be Situationally Aware. Parts of your organisation may be at different stages of evolution. As such, components should be optimised based upon context. "Agile" may not be suitable for everything and everyone across the organisation.

[Simon Wardley] 🎬

#7 If you are optimising for the flow of value there are only 4 team topologies required. [Matthew Skelton and Manuel Pais Team Topologies] 📚

#8 When you have defined products in a customer-centric manner, with a long view in mind, and as broadly as possible, structure follows the product. As such, if you want an effective Product-Centric Organisational Structure, define the Product first

[Ellen Gottesdiener] 📝

#9 To create great teams focus on these 6 conditions: Real Team, Compelling Purpose, Right People, Sound Structure, Supportive Context, Team Coaching.

[Leading Teams by Richard Hackman] 📚

#10 You can only manage five things in a complex system: Constraints, Identity, Affordances, Assemblages, Attractors.

[Dave Snowden] 📝

#11 The three things organisations should have a deep understanding of: Knowledge of customer demand, Appreciation of what constitutes value, how to measure the system’s achievement of purpose in customer terms.

[Beyond Command and Control by John Seddon] 📚

#12 You cannot "optimise" a complex adaptive system. Instead, explore through experimentation how the system is currently disposed and then 'nudge' it towards a new direction understanding the system may respond in unexpected ways.

[Toby Sinclair]

#13 Systems Thinking, whilst helpful, can lead to thinking traps that don't embrace the complex nature of organisations. As such, when doing Systems Modelling, acknowledge that things are more complex than they seem.

[Toby Sinclair]

#14 Any organization that designs a system will produce a design whose structure is a copy of the organization's communication structure. As such, implement the Reverse Conway's Manoeuvre.

[Matthew Skelton and Manuel Pais Team Topologies] 📚

Behaviour Change

I have come to learn that:

#1 When the behaviour of the individual and the organisation are at odds. The behaviour of the organisation wins.

[Atomic Habits by James Clear] 📚

#2 People don't resist change, they resist coercion. So instead of forcing people to change, take time to listen to their concerns and co-create change with them.

[Esther Derby] 📝

#3 There are only two ways to influence human behaviour: you can manipulate it or you can inspire it. Therefore find the internal "why" that people can connect with.

[Start with Why by Simon Sinek] 🎬

#4 Behaviour Changes in 3 Ways. You can have an epiphany, change the environment or change behaviour in tiny ways. The most successful, if done consistently over time, is to change behaviour in tiny ways. It's something anyone can do.

[Tiny Habits by BJ Fogg] 📚

#5 Behaviour happens when motivation & ability & prompt converge at the same moment (B = MAP). It's important to understand that motivation is fickle and prompts only work when the behaviour is easy enough to do. Therefore first focus on making the behaviour as easy as possible to do initially.

[Tiny Habits by BJ Fogg] 📚

#6 A good strategy is to add new habits one at a time but break habits by stopping several at the same time.

[Tim Ferris Podcast #97 with Naval Ravikant] 🎧

#7 Every habit you have follows the same 3–step pattern: Reminder (the trigger that initiates the behavior), routine (the behavior itself; the action you take), and reward (the benefit you gain from doing the behavior)

[Atomic Habits by James Clear] 📚

#8 Behaviour will not change if it is not crystal clear what Behaviours are expected. To make behaviours crystal clear leverage Cultural Architects within the organisation to act as role models.

[Barcelona Way by Damian Hughes] 📚

#9 You need to make old behaviours impossible to do. Otherwise, in times of crisis, fear or uncertainty people will revert back to their old, default behaviour

[Knowing Doing Gap by Jeffrey Pfeffer and Robert I. Sutton] 📚

#10 When psychological safety is low, people will be afraid to take the risk. When adopting a new, uncertain behaviour the fear of failure is always higher. If there the environment is not safe people will default to their existing, automatic behaviour. Don't expect people to change if they don't.

[The Fearless Organisation by Amy Edomondson] 📚

#11 Behaviour change takes much longer than you appreciate. It's not months but years of consistency. This can easily be demotivating so instead of focusing on the outcome focus on consistency. Make consistency the goal

[Toby Sinclair]

Change Management

I have come to learn that:

#1 The Obstacle is the Way. The key success indicator of any change effort is how many obstacles (aka impediments) have been overcome. If you ignore the obstacles they will continue to slow down progress. It's like taking a 100mile detour rather than tackling the problem in front of you.

[The Obstacle is the Way by Ryan Holiday] 📚

#2 Focus energy on the Early Adopters. Limit energy expenditure with Laggards

[Crossing the Chasm by Geoffrey Moore] 📚

#3 Don't be fooled by the "workshop trap". When people leave workshops they'll likely be motivated to change the world. This kind of Motivation is fickle and will likely run dry when Monday morning arrives. Instead, focus on small changes and make the change as easy as possible to do.

[Tiny Habits by BJ Fogg] 📚

#4 Don't do large "Transformation Programs". Instead, focus on meaningful outcomes for the business, start small, make the desired behaviours easy to do and keep consistent over time. [Toby Sinclair]

#5 We must become better at asking and do less telling in a culture that overvalues telling. Therefore spend time asking questions rather than telling your team what to do.

[Humble Inquiry by Edgar Schein] 📚

#6 You cannot force another person or a system to change. We sow seeds, some fall on fertile ground, others on impenetrable soil, and yet others sprout but get overgrown by weeds. Our responsibility is to keep sowing the seeds, that is all we have control over.

[Sonja Blignaut in The Cynefin Book] 📚

#7 Gap Thinking, the gap between current and target state, can lead to you to get more stuck. It's like quicksand, the more you try to move towards the target the more you are stuck in the current state. Another way is to get a grasp of your current conditions and what would be a more ideal current state. This raises awareness of what's going on now and as such a better appreciation of what needs to change.

[Jabe Bloom on Twitter]

#8 Change cannot be managed. Change is a complex process that emerges in often strange and novel ways. Therefore instead of managing change create conditions for it to emerge.

[Toby Sinclair]

#9 There are three reasons why people conflict: Lack of shared information, Disagreement about values and experiences, Personality, past history or other outside factors. When helping people navigate change help them be aware of the level the conflict. Use appropriate approaches at each level.

[Michael Wilkinson] 🎧

Measuring Change

I have come to learn that:

#1 You will achieve better organisational outcomes if you Minimize Output, Maximize Outcome and Impact.

[Jeff Patton] 📝

#2 The easiest thing to measure often gets measured. As such the easiest thing to measure is often activity instead of outcomes. Outcomes are usually hard to measure. To shift the focus to measuring outcomes you have to shift the balance. Make outcomes easy to measure and activity hard to measure.

[Toby Sinclair]

#3 You are incentivized to believe the things that you want to be true. As such, if you have invested time and energy in the change you'll want to believe that change has happened. As such, whatever you do, in most cases you'll declare success.

[Charlie Munger] 📝

#4 When a measure becomes a target, it ceases to be a good measure. Therefore don't use measures as targets.

[Goodharts Law] 📝

#5 You can categorise the outcomes organisations need to work towards for success into Better Value, Sooner, Safer, Happier

[Sooner Safer Happier by Jon Smart] 📚

#6 There are two measures that help organisational effectiveness: Capacity - The volume of demands we can service. Capability - How well we do them in eyes of the customer.

[Beyond Command and Control by John Seddon] 📚

#7 If you optimise a system for efficiency, effectiveness will reduce. If you optimise a system for effectiveness, efficiency will increase.

[Efficiency Paradox by Niklas Modig] 🎬

Culture Change

I have come to learn that:

#1 You don't think your way into a new kind of living. You live your way into a new kind of thinking. Culture only changes when behaviour changes.

[Henri J.M. Nouwen] 📝

#2 We are what we repeatedly do. Excellence, then, is not an act, but a habit. Culture is the product of the habits of people within the organisation

[Not Aristotle] 📝

#3 Change Behaviour to Change Thinking. Therefore for culture to change, you must enable behaviours to change. To enable behaviours to change make it easy to do.

[John Shook] 📝

#4 Every action you take is a vote for the type of person you wish to become. No single instance will transform your beliefs, but as the votes build up, so does the evidence of your new identity. As such, focus on the consistent behaviours over time that will slowly change your organisational culture.

[Atomic Habits by James Clear] 📚

#5 Culture is the product of the rules, policies, procedures within the organisational environment. You might call these constraints. These influences the employee's assumptions and beliefs about "How things get done around here". These beliefs drive the employee's behaviour. To change the culture change the environment, the rules, policies etc. and make it easy for people to adopt new behaviours

[Toby Sinclair]

#7 A bad system will beat a good person every time. As such if you hire great people they may not succeed if the environment does not enable them to do so.

[W. Edwards Deming] 📝


I have come to learn that:

#1 The first follower transforms a lone nut into a leader. As such to build a movement you need to encourage followership as a leadership act.

[Derek Sivers] 🎬

#2 The difference between successful people and really successful people is that really successful people say no to almost everything. The best leaders say no often.

[Lead at Speed by Sophie Devonshire] 📚

#3 Leadership is a focus on creating the right conditions in the environment for people to succeed.

[Unlocking Leadership Mindtraps by Jennifer Garvey Berger] 📚

#4 The temptation for leaders is to lead as a chess master, controlling each move of the organization. The best leaders act as gardeners, enabling rather than directing, creating a healthy ecosystem.

[Team of Teams by Stanley McChrystal] 📚

#5 Many people have a strong Fundamental Attribution Bias. The tendency for people to under-emphasize situational explanations for an individual's observed behaviour while over-emphasizing dispositional and personality-based explanations for their behaviour.

[Wikipedia] 📝

#6 We are drawn to leaders and organizations that are good at communicating what they believe. Their ability to make us feel like we belong, to make us feel special, safe and not alone is part of what gives them the ability to inspire us.

[Start with Why by Simon Sinek] 📚

#7 Leadership is communicating to people their worth and potential so clearly that they are inspired to see it in themselves.

[Turn the Ship Around by David Marquett] 📚

These insights are not static and will always be evolving.

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