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So what can we do? Here are my key takeaways from the first six chapters of Nick Tune's excellent book "Architecture Modernization
Socio-technical alignment of software, strategy, and structure".

1. You don't modernize for the sake of modernization!

You need to express the true business narrative, the desired business outcomes and understand how architecture modernization can drive it.

Legacy architectures are usually providing some business value, but they are also slow and expensive to change, prone to unreliability and increasingly open to new security compromises. 

The costs of software decay become visible when the costs of repair are high.

2. A modern architecture is a socio-technical architecture!

How we organize people and their interactions will be mirrored in our architecture.

When you start modernizing, don't design the social structure (teams, organization, workspace) and the technical system architecture in isolation.

3. Surprise, there is no quick fix!

Moving from aging to modernized architecture is hard, and it's complex. If this was a quick fix, it wouldn’t be one of the biggest problems companies today face. 

That said, it shouldn’t take years for modernization to start delivering value. 

The architecture is never fixed and will continuously evolve as the context is changing. Don’t treat modernization as a traditional one-off project.

4. Modernization is touching every aspect of your operating model!

Will you modernize with the same operating model, mindset and way of working that caused the garden to overgrow in the first place? Bad idea.

You should embrace deep changes in how you empower cross-functional & value stream aligned product teams, involve the users, break down the business and IT barriers, adjust the funding models and invest in technical quality.

At least if you want to avoid yet another large and expensive modernization initiative in a few years.

5. Modernization is a social activity!

Modernization is a social activity where diverse groups come together and share their knowledge to make as much details and complexity visible.

You must get rid of the traditional mindset of treating “THE BUSINESS” (the customer giving orders) and “IT” (the vendor taking orders) as separate units. They are in fact two sides of the same coin. 

This is not just about rebuilding an old system, it’s also about modernizing the business domain and business processes. It's a joint effort.

What do you think companies must do to succeed with architecture modernizations?

There is still a place for your advice and answer as a leader, you should just try to slow down the rush to it as your default behavior.

A little more asking people questions and a little less telling people what to do. Here are the seven magic questions to ask.

What's on your mind?

An open question that invites people to get to the heart of the matter and share what's most important to them.

And what else?

A question that creates more wisdom, more insights, and more options because the first answer someone gives you is almost always never the only answer, and it's rarely the best answer. When someone says "there is nothing else" you have succeeded.

What's the real challenge here for you?

It's time to focus. When people start talking to you about the challenge at hand, what they are laying out for you is rarely the actual problem. The "for you" pins the question to the person you are talking to.

What do you want?

This one is difficult to answer. We often don't know what we actually want. The illusion that both parties to the conversation know what the other party wants is pervasive, and it sets the stage for plenty of frustrating exchanges.

How can I help?

This question is forcing your colleague to make a direct and clear request. That may be useful because she might not be sure why she started this conversation with you. 

Second, this question stops you from rushing into "rescuer" mode where you offer advice or start to take over responsibilities.

If you are saying yes to this, what are you saying no to?

This question is more complex than it sounds, which accounts for its potential. It puts the spotlight on how to create the space and focus, energy and resources that you'll need to truly do that 'Yes'. 

It's all too easy to shove another 'Yes' into the bag of our overcommitted lives.

What was most useful for you? / What did you find most valuable about this chat?

This one gives you feedback, it will give you guidance on what to do more of next time. It gives your colleague a chance to recall and reflect on key takeaways from the conversation. That's when we start learning.

Drop the "Why?" questions

In a coaching conversation, don't ask the 'Why' questions. You put them on the defensive. Rather than "Why did you do that?", try "What where you hoping for there?" or "What made you choose this course of action?".

And by the way, don't forget to ask the questions with genuine interest and curiosity and acknowledge the answers.

"The Coaching Habit" by Michael Bungay Stanier.

So what do you find in a great story?

• Identifiable characters. Someone we care about and connect to.

• Authentic emotion. Felt by the identifiable character. It is through that emotion that the receiver experiences empathy with the story. This is essential to make it more relatable, compelling, and sticky.

• A significant moment. A specific point in space, time or circumstance that sets the story aside from the rest. Instead of going big and broad, we need to go small and detailed. Don't stay too vague, too high level, too broad and too general.

• Specific details. Involve use of specific, descriptive, sometimes unexpected details and imagery that are relevant to the intended audience in an effort to create and draw the listeners into a world that sounds familiar to their own. The finer the detail, the better. This is how you tell the audience that you know them.

Why don't we tell more stories? The biggest barrier to not telling your story is assuming you don't have a story in the first place.

It isn't a lack of stories that keeps you from being able to find yours but rather the ineffective questions we use to get them. Getting better stories requires asking better questions. 

Our stories attach themselves to the nouns in our lives. The people, the places, the things, the events. A memory can be turned into a story.

Pick a story that fits your needs, your business and your audience. 

You are not telling a story for the story's sake. Who are you telling this story to? What do you want them to think, feel, know or do?

Start with a story next time! It eases the natural tension that sometimes exists between audience and speaker. Starting with a story helps to break down barriers and makes you a person just like them instead of the expert in front of the room they are forced to listen to.

"Stories that Stick" by Kindra Hall

In the Age of Digital, don't use methods from two technological revolutions ago on unique, knowledge-based work that is emergent and full of unknown-unknowns.

Start with the "Why"

Start with why if the why is not already clearly understood, and communicate it three more times than you think you need. You cannot over-communicate the why.

What happens if the status quo is maintained? What’s the “so what”? Why do people need to go through the discomfort of change and lack of mastery? What appeals to the selfish gene? 

There should be a compelling why unique to your context and organization, which is the call to action. “We want to be more agile”, “We want to be more lean”, “We want to be more product-oriented” are insufficient calls to action.

A useful exercise is doing a “five whys”. Break into pairs with the starting question of “Why change?” and take turns asking why five times with each answer forming the basis of the next question.

Desired outcomes

Next, articulate and agree on your desired outcomes. Agile, DevOps, Lean and Design Thinking are the means to an end, they are not the end. They are bodies of knowledge, wisdom, principles, and practices to be applied in context to achieve desired outcomes.

Outcomes should be measured and visualized. Focus on the trend over time and relative ranking on improvement rather than on absolutes, as everyone has a different starting point. The goal is to improve over time.

Business outcomes are hypotheses and they are nested with a lineage up to longer-term, organization-wide strategic outcome hypotheses. Outcomes are not passed down, unchanged, in a traditional order-giver, order-taker manner. Instead they align. They are written and “owned” by the people at each level in the nested value streams.

Leaders go first

The leadership team is number one. If a leadership team is not willing to role model desired behaviors, why shall other teams do it?

People in senior roles have a disproportionate impact on behavioral norms. Trust and role modeling are essential.

Ways of Working Center of Enablement

In order to be successful, there is a need for people who are dedicated full time in a servant leader capacity to orchestrate the improvement of the system of work across an organization. 

For a large organization, the success patterns is to have federated Ways of Working Centers of Enablement, with one for each business unit or value stream and a central one providing the team-of-teams coordination.

The Center of Enablement deal with impediments to achieve the outcomes that bubble up, with a goal of solving them at the lowest possible level. They are not a department of improvement where improvement actions are lobbed over the fence.

There should be an impediment backlog, with the Center of Enablement orchestrating the right people in the organization to help alleviate the top-priority impediments where this is beyond the sphere of influence of a team.

This is leadership in ways of working, being coaches, guiding people on the journey, sharing learning internally and externally, communicating, creating community, rewarding and recognizing desired behavior and outcomes.

Achieve big through small. 

Achieve big through small instead of big through big. Minimize time to learning. 

Change is hardest at the beginning. There is no one size fits all. Context matters. Every environment is unique. Starting small makes it safe to learn, keeps change within risk appetite, and generates social proof unique to your context.

People have a limited velocity to unlearn and relearn. You cannot force pace of change. If you do, you will only get new labels on existing behavior. Start small and within the risk appetite. 

Amplify the experiments that work well, and quickly dampen the ones that don’t. Experiments are then amplified or dampened.

Let the natural champions go first

Allow people to satisfy their psychological need for agency and control, the need to feel in control of one’s own destiny. Allow the Innovators, the natural champions, to identify themselves. They are motivated by the buzz of being first, and have probably been working this way formally or informally for some time. 

Invite participation and get behind the champions. Give the champions the coaching and the support they need in order to deliver business outcomes. As the benefits are seen, recognized and communicate via every mechanism available, the early adopters will want to join in. They can see that it’s safe to put a toe in the water. Gradually invite them in too, within the pace of unlearning and relearning and within risk appetite.

Invite everyone from top to bottom

Invite everyone from top to bottom (a vertical slice), don't leave the pressurized middle behind. They have to deliver, come what may, and are now being asked to change ways of working as well as continuing to deliver. It’s a difficult role and is often missed during a change that is sponsored from the top table and implemented at grass roots. 

Everyone learns together, and no one is left behind. It's not easy, as the most enthusiastic group of people is at the team level. 

Communicate, communicate and communicate

Communicate three more times than you think you need. Use every communication channel at your disposal and add some more.

Use the channels to reinforce the why, the values and principles, the outcomes, to recognize desired behavior and to do story-telling. Have senior leaders recognize the great work of teams in improving outcomes and have teams share their stories.

Stick at it

It requires commitment and resilience. It takes years for sustainable, lasting culture change, for genuine agility. 

For a large organization with a tailwind, it’s three to five years, longer with headwind. There are no shortcuts. 

In organizations with traditional ways of working, change is staccato. In evolutionary biology terms it is "Punctuated Equilibrium" rather than "Punctuated Gradualism". There are long periods of stasis, then a burst of disruptive change. There is lack of ongoing continuous improvement.

Become the best at being better.