NOTE: There was an issue with zoom screen share, so the slide animations are frozen from 12:05 until 15:19.
Therefore, you can also download the slides directly from here:
https://jessefewell.com/wp-content/uploads/2021/01/20th-Anniversary-lowres.pdf

SUMMARY: As we approach the 20th anniversary of the “Manifesto for Agile Software Development“, it’s time to ask some big questions: Are projects really any more successful these days? Have companies truly shed any of the bureaucracy? Are professionals actually feeling the empowerment we’ve been fighting for so long? And where are things headed in the next few years?

In this fun and illuminating talk, you will hear observations and patterns from Jesse Fewell, author, speaker, and agile champion since the late 90s. From certifications to org models to career tracks to technology advancements, Jesse will cover the full range of topics we hoped to impact, along with some alarming surprises along the way.

ABOUT THE SPEAKER: Jesse Fewell is an author, coach, and trainer who helps senior leaders from Boston to Beijing transform their organizations to achieve more innovation, collaboration, and business agility.

A management pioneer, he founded and grew the original Agile Community of Practice within the Project Management Institute (PMI), has served on leadership subcommittees for the Scrum Alliance, and written publications reaching over a half-million readers in eleven languages.

Jesse has taught, keynoted, or coached thousands of leaders and practitioners across thirteen countries on 5 continents. His industry contributions earned him a 2013 IEEE Computer Society Golden Core Award.

His book, Untapped Agility – 7 Leadership Moves to Transform your Transformation, was released in July 2020.

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Is a reorg leaving your team in chaos? Don’t wait—offer your boss a few ideas for the new structure. Is a new initiative too vague? Give your team five practical starting points. The people who get hired, promoted, and remembered are those who contribute, who show up with solutions rather than waiting for instructions.

Let me share a few examples of what this looks like in action.

Last spring, I met a project manager at a conference. She was frustrated because her leadership team wasn’t giving her direction on a major business transformation. I asked her, “What if they’re waiting for you to set the direction? What if the answers you’re looking for are the recommendations already in your head?” Two months later, she called me to say that perspective had changed everything. “I set a strategy, asked my leaders to back it publicly, and people rallied around it,” she said. Her initiative earned her a promotion to lead an entire transformation team.

Contrast that with another situation I encountered in the fall. I worked with a leadership team stuck in a toxic stalemate. Mid-managers were looking to their VP for guidance on restructuring, while the VP was convinced a “servant leader” should let her team find the answers themselves. But when no one stepped up, frustration brewed. The VP eventually left, and the mid-managers were left hoping her replacement would fill the void. The result? Wasted time, fractured trust, and lost opportunities.

More recently, I coached a Scrum Master struggling with a similar dilemma. Her team was floundering—juggling the ambiguity of a new project and the departure of their tech lead. She had ideas for how to move forward but felt constrained by the notion that good professionals “don’t step on toes” or “stay in their lane.” During our session, she realized what the VP I mentioned earlier could not: she was the leader the team needed. Sharing her ideas and collaborating with her manager wasn’t overstepping; it was exactly what the situation required.

Yes, the world has its share of good-idea fairies, Captain Obviouses, and chatty know-it-alls. But you know what? I’ll take them over people who bring nothing to the table. Bad ideas and bloated opinions can be refined; silence and inaction are far harder to fix.

It doesn’t matter if you’re a Product Owner, Scrum Master, Project Manager, Coach, or Consultant. Being proactive, offering ideas, and seeking solutions don’t make you rude or “command and control.” They make you helpful. And every one of us has the opportunity to be helpful.

My hope for 2025 is that more people choose to lean into the ambiguity that bothers them most. Be the one who offers clarity. Be the one who takes action. Because leadership isn’t a title—it’s what you do when it matters most.

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ROI Comes from Mass Adoption

Let’s face it: the true ROI of AI emerges when everyone’s on board. High-performing organizations don’t dabble—they adopt these tools widely, aiming to equip the whole team. A National Bureau of Economic Research published a paper finding generative AI boosted customer support productivity by 14% on average, with an even bigger impact on newer employees who saw productivity gains of 34%. Not only does AI make the average employee better, it can even turn lower-performing team members into stars.

The straightforward case for AI adoption goes beyond just broad use; it also involves job-specific AI tools. Project management platforms like Smartsheet, Asana, and Monday.com now use task data to power schedules and projections. Meanwhile, CRM systems like Salesforce and HubSpot offer sales reps insights into hidden prospects. In other words, companies that hold back on rolling out AI could soon be at a clear disadvantage, lagging behind competitors who are taking full advantage of the technology.

This potential has some leaders leaning toward a permissive approach. Harvard’s Paola Cecchi-Dimeglio  advocates for a culture of open experimentation, arguing that leaders should “encourage employees to experiment with AI and share their experiences. This can demystify AI and highlight its practical benefits across different roles and functions.”

But while leaders may want to empower employees to explore, there’s a big gap in employee confidence.

In a recent survey by Skillsoft, 74% of employees  said they don’t trust their company’s training for AI, and only 40% of IT leaders  say they even have formal programs to support AI adoption. The “innovation fog” that clouds employee confidence is just as frustrating for managers, who face questions like, “Which training programs make the most sense? Which vendors are reliable? And how will we measure success?”

The good news is that tried-and-true strategies can help cut through the fog. Here are a few ways leaders can accelerate meaningful change and help AI adoption get off the ground:

• Offer Domain-Specific Training: Those PM tracking tools are fundamentally different than those sales platforms. We should train people accordingly. As Cecchi-Dimeglio suggests, tailor programs and guidelines to specific roles.
• Collect & Celebrate Wins: Once you’ve got training programs going, market them. Highlight early adopters’ success stories in a regular newsletter to spark broader interest.
• Nurture a Community of Champions: One forward-thinking leader holds a weekly “GenAI & Citizen Developer” webinar, where employees share tips on tools they’ve tried. For most, just listening in is enough to get them inspired to experiment. 

Safety Without Slamming the Brakes

With all this momentum, there’s a reality check: more users and more tools bring more risks. These risks range from data privacy breaches to empowering bias and even criminals. Leaders are responding in various ways to ensure they capture AI’s benefits without compromising safety.

For example, President Biden’s “Executive Order on AI” led to the NIST AI Risk Management Framework, a hefty playbook that defines 72 (!!) controls to “govern, map, measure, and manage” AI. Meanwhile trade associations are also weighing in, such as the ISO which offers three global standards totaling over 100 pages (!!) on AI governance. Then, there are the tech company alliances and individual vendors offering their own frameworks. 

With the onslaught of so much governance guidance, it can be hard to know where to begin. Fortunately, we can start with a few common-sense fundamentals:

• Partner with AI Vendors: Whether you go with OpenAI or Google Gemini, vendors offer solid guidance on data security and governance. Most will throw in enterprise governance features—and even bulk discounts for larger companies.
• Publish Simple Usage Guidelines: People want to do their jobs well. Give them straightforward guidelines so they can experiment safely. Many public resources are available, but often they’re overly technical. A clear, company-specific guide can go a long way.
• Inform, Don’t Enforce: Often, teams don’t realize they’re taking risks. Security teams can run scans, then notify managers with a risk assessment and safer alternatives. For bigger projects, offer governance specialists as advisors. With “Governance as a Service” (GAAS), you enable safety without clamping down on innovation.
• Offer Budget Incentives: If teams are using unauthorized versions of tools on their own budgets, offer discounts on safer, vetted alternatives through centralized procurement. Imagine the response when governance teams make safer options both cheaper and easier to use.

You Can Have It Both Ways

AI brings unprecedented opportunities—and equally unprecedented risks. The typical reaction is to either charge full steam ahead or hold back in caution. But transformational leaders know the real power comes from a creative balance: fostering innovation with safety firmly in the mix. When leaders can pull this off, they unlock AI’s potential without compromising their enterprise’s integrity.

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A balanced guide to Agile transformation that gets past all the hype and jargon to help leaders tailor Agile to their unique organizational setting.

Agile transformations are supposed to make organizations modern, competitive, and relevant. But in the rush to jump on this latest bandwagon, many leaders make the mistake of adapting superficial versions of agile techniques, only to find that their organizations are only marginally better versions of their previous selves. My new book cuts through the “quick fix” hype of agile theory and uses decades of agile coaching experience to unpack the mistakes that hold organizations back. In it, I identify the seven common leadership moves that can be used to unblock stalled agile transformations.

Once you understand these moves, you’ll be able to do the hard work of building a wholeheartedly agile organization: your transformation will go more than skin-deep. Based on case studies from the field, this book unapologetically engages with the messiness of organizational culture and process change, and will help you navigate those challenges in a way that works for your own people.

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We’ve been told that to achieve more innovation, more collaboration, or more agility, we need to adopt modern practices. Unfortunately, many of those practices seem fundamentally incompatible a team’s reality on the ground. If the experts say we have to use stable teams, product-based funding, but our current state won’t allow for it, what do we do? Short answer: We adapt. The path forward is to be agile with your agile, to transform your transformation.

Tailoring is management common sense

Much has been written in the project and product worlds about “tailoring” processes and practices, based on the work being done. Let’s pause for a moment to take a look at some key points. The idea of The PMBOK Guide Sixth Edition officially defines tailoring as follows:

“Determining the appropriate combination of processes, inputs, tools, techniques, outputs, and the life cycle phases to manage a project is referred to as “tailoring” the application of the knowledge [of project management].”

That’s a fancy way of saying that each organization should customize its approach to delivering work based on the specific dynamics and demands of the environment.

Moreover, these adjustments are not optional. The guide goes on to say:

“Tailoring is necessary because each project is unique; not every process, tool, input, or output identified is necessary.”

Ironically, if your PMO, Center of Excellence, or other standards group has defined their process playbook by merely copy-pasting a textbook approach from PMI, from Google, or from Spotify… they are violating the ASNI standard for project management.

Tailoring was always core to Agility

Now if you think that point is only for traditional project management and has nothing to do with Agility, then you would be mistaken. The original Agile Manifesto closes out its declaration of values and principles with this very topic, saying:

“At regular intervals, the team reflects on how to become more effective, then tunes and adjusts its behavior accordingly.”

That’s the conclusion, the climax, the final word. Kind of important.

So whether you come from a formal standards perspective (project management) or a more informal values-based perspective (Agile Manifesto), the expectation is the same: modify how you do your work, based on the situation at hand.

Put another way, if you believe in continuous improvement, then by definition whatever practices you are using are not optimal. If you are still using that fancy new devops method strictly out of the box, then you are simultaneously neither compliant with international standards nor consistent with the spirit of agility. Not adjusting your practices is a double-fail.

Okay, but HOW do we Adjust?

Unfortunately, there is almost zero guidance on how to go about tailoring effectively. Much of the literature in place today strongly advises that you do it but offers no filters, guardrails, or tips for doing so. That’s a problem, because if we don’t make the right adjustments we can get some very unwelcome side effects, such as:

• If we don’t adjust enough, we still struggle unnecessarily.

• If we adjust it too much, we lose all the benefit we’re trying to get.

How do we customize our practices without diluting their potency or even making things worse? We need to offer people a viable alternative beyond all-or-nothing.

The 3P Tailoring Technique

To do that, we can walk through a simple set of questions to figure out some degree of doing things better:

1. Listen to their PAIN. Ask the team what is the specific frustration, difficulty, challenge they would face if we were to use a given technique.

2. Explain the PURPOSE. Share the underlying principle of why we recommend that technique. What is the in- tended benefit?

3. Design a PIVOT. Ask the team how might we adjust the technique so that we could get at least some of that benefit.

Here is how the process works in real life.

Tailoring Example for Documentation

Let’s say Maria the Manager wrestles with the excessive documentation generated in regulated, life-critical environments. Here’s how her team might approach that topic in their transformation.

1. Maria’s Pain. “Experts say documents are wasteful. But we build medical devices. Those documents are how we pass compliance audits, never mind the rigor they foster to prevent tragic mistakes. ”

2. A colleague explains the Purpose. “Remember, the emphasis of ‘working product over comprehensive documentation’ is to avoid distractions that waste time. I’m sure you can think of how to adjust your documentation practices to save time, without compromising the safety of the work you do.”

3. Maria’s Pivot. “Well, much of our time is spent using our specifications to convey designs to the builders. But talking is faster than typing. We could accelerate knowledge sharing by including the designers and auditors in our meetings more frequently. Then writing the compliance documents will be more focused on the final product, rather than directing intermediate work. That might improve quality and speed, without losing any of the documentation the government requires. Let’s try this as an experiment for one subset of the overall product.”

That’s how it works. When moving on a journey towards new ways of working, leaders often get confused on how to adopt things like automation, stable teams, or prototyping. By making appropriate adjustments to established practices, you can help your transformation move forward, rather than getting stuck in the false choice of all-or-nothing.

[To learn more on this topic, click here to register for IIL’s Agile Scrum 2020 Online Conference]

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I’m not happy with a lot of negativity out there. I hear people talking about their transformation saying, “this transformation is a failure because this leader doesn’t get it”. Or, “we’re doing a scrummerfall”, or “you know that PMO is in the way, or that group over there is fighting us harder, and so we’re still doing legacy funding and all of our projects are running at the same time and it’s just a failed transformation.” Hang on there. I’m here to say that there’s no such thing as failure when you’re talking about change. There’s only a question of degree of progress.

There are three perspectives on this that I want to share with you and I’m feeling pretty convicted about them. Time, energy, and impact.

So, when it comes to time, one of the questions you want to ask yourself is, where am I in the stage of the change. Are you merely sowing seeds? Are you the first person to mention words like digital or devops, or the product mindset? And, if you are, then you need to be prepared to wait for those seeds to take root and before you see any kind of momentum, or promise, or growth. And, then it’s going to take even longer for there to be the kind of beautiful fruit blossoming in your organization. That’s going to take time. In fact, you may not be around to see the harvest. He who does the harvest may not be he who sowed the seeds. Instead, it might be more like she who is doing what she can right now to push the ball forward. Time matters. And, just because you’re frustrated about doesn’t mean it’s not going to get done.

What about energy? You know, we set out on change initiatives. And, we’ve got point A, point B, let’s go, and we forget that it’s a roller coaster. There’s some up and downs. And, you might be a fast buggy in the beginning. Let’s go, let’s get some pilot projects, let’s do some people processing some tools, let’s roll out some training, and then whoa! Look at all the blow back, the pushback. And then look at all the people that are just resisting and they’re not really getting it, and they’re doing it wrong. And, then I’m going to go topsy-turvy, loop-to-loop, and now I’m guy who’s going back into phase two of this transformation, a little bit worse for the wear. Because, change is hard. Change is messy. It’s one of these things where it doesn’t go according to plan. And, isn’t that what adaptive, modern leadership is all about? Things don’t go to plan as often as they used to in a more complex, dynamic world.

And, then finally, impact. Because, when we’re talking about enterprise transformation, we’re going to transform all of our portfolios from project-based to product-based. And, we’re going to go fully digital in the entire organization. I’m an enterprise transformation coach. That’s what I do. And then we all get laid-off. I’ve been there. A couple times. Communications, manufacturing, couple of different organizations, and it sucks. I’ll be honest. And, you see all of your transformation efforts just kind of blow up in one move, one swoop. But you know what? There might be a team that survives that. And all of the work that we did is going to stick with them and they’re going to keep thriving and moving forward. And, there might be a grumpy bug still around but then the team as a whole, they’re thriving. You had impact and it stuck around. But, what about that person that didn’t survive the layoff? They didn’t have any benefit of the transformation. Not so fast! They are now going to be sharing those thoughts and ideas out to their new gig and the new place where they’re working. So, you may have had an impact on not just on the team that stays, but on the people, who are moving forward.

There’s no such thing as failed agile transformation. Forget the negativity. Get some perspective on time, energy, and impact.

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I believe, at the end of the day, agile is a moral imperative.

You get people wrapped around the axle that if you’re not agile, then you’re not cool. And we’re going to have our agile transformation … Why?

Well, you have to be more agile. Why? The more you dig deeper into this you find that it’s a belief system. What we’re talking about here are three key components. I’m going to share with you three things, three things that people talk about, and it’s going to help you understand where all of this passion and all of this energy and all of these dogmatic fights come from, and the first one is ultimately, at the end of the day, when we talk about agile, it’s deliver early, deliver often. Deliver early, and deliver often. That’s the point.

The point is to get more value into the system. Unfortunately, that’s really hard to do, so we need to empower self-organizing teams, tap into the talent, harness unleveraged, unutilized, awesomeness. By delegating more and giving your people more support to get the jobs done. Unfortunately, they’re not ready. They are not ready for new degrees of discretion and new degrees of initiative and control, and so you’ve got to start with where you are, with what you’ve got, and just inspect and adapt and get better.

That’s how I like to articulate the three key pillars of what this agile thing is. But when you take a second pass through, it starts to take a different color when you think about deeper principles. So when we talk about deliver early and often, delivering early and often is about getting people what they paid for. It’s overcoming that contract negotiation to customer collaboration and getting value out the door in today’s modern competitive world where things can’t wait.

And so you hear a lot of businesses talk about business agility. This is what they’re talking about. They’re talking about getting what they paid for. And empowering teams, this is another depending on who you ask, agile’s all about teams. Why? Because empowering self-organizing teams is about treating our people with respect. You know, in order to work here, you’ve got to have a masters degree, 5 industry certifications, 10 years of experience, pass a gauntlet of 10 interviews, be the best out of 100 person… so it makes sense that as soon as you get here, we’re going to give you a babysitter micromanaging your every move?

This is about respect, and that is a moral mandate. And unfortunately, people, they’re just not ready for all of the sudden being treated like adults. Or all of the sudden, being given more initiative and control over the work they’re doing, so you’re just going to have to start where you are and inspect and adapt. You’re never done growing and getting better. You know, if you’ve ever read The Innovator’s Dilemma, it’s a fantastic book. Here’s the dilemma. Well, everything that we believe to be good management and good management practices fundamentally gets in the way of those good companies surviving disruption.

So whatever you think you’re good at today, it’s not good enough for tomorrow. Inspect and adapt and get better. And so, you start to see this, this isn’t about a methodology, about you know, sprints and back velocity. It’s not about a mindset of being growth-oriented. No! This is about morals. This is a moral imperative, and that’s why you see a lot of people getting passionate about it. That’s why I’ve chosen it to be my career, is helping people achieve what they paid for, respect and autonomy at the workplace so you can be fulfilled in what you do, and to fulfill your ultimate potential by inspecting and adapting and getting better.

So hopefully that was interesting to you. Hopefully that helps you give you some talking points and you can articulate this agile business out in the workplace. Agile is not a mindset. It’s certainly not a methodology, nor a specific method. It is a moral imperative.

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That’s right Command and Control is a good thing!

Command and Control – that’s what I want to talk about today. This term that agile people or anybody floating around in management circles these days about command and control is a negative leadership style. Well, isn’t that lovely? That’s not what it’s meant to mean. Not what it was meant to mean. Command and control refers to an organizational capability, an organizational competency. Comes out of the military term, the military in space, the military sector. And it’s intended to describe some very important things. So first, let me give you the positive example.

This is a leadership book that you’ve got to checkout. Talks about a navy submarine commander Dave Marquet, who turned around his submarine from worst in the fleet to best in the fleet in the matter of just a couple of years because he was the commander. We need a leader. We need a visionary. We need somebody who’s got a definition of what success looks like. Who’s our Steve Jobs, who’s our Jeff Bezos, who’s going to be the one that moves us forward. Now in scrum, that’s called the product owner, in extreme programming we call it the on-site customer. And so in an agile conversation that’s well accepted. In fact, it’s agreed upon that it’s necessary to have a commander, a visionary, someone who takes us where we’re going. Furthermore, in the book, he describes shifting the old style of leadership to a new style of leadership, he doesn’t call it command control.

He calls it the leader-follower model that he wants to replace with the leader-leader model where we tap into the talent of our people, our teams and delegate more control and initiative to where it is. And in that book he said that the key to giving teams more control in their work was in approving vacation time. That’s fascinating how that one little thing turned into a pivot, an inflection point in the organization, the submarine, about 100 people to make it all go right.

Now, the reason this drives me crazy is because it’s become a sloppy term to describe negative leadership. Agile people like to make up words. Well, the word agile didn’t exist before 2001 until all of these lightweight process advocates came together and came up with some core principles. Also fun fact – word waterfall didn’t exist – certainly not in the waterfall paper by Winston Wright, until agile came along and needed to give a name to the enemy. So “you do work I don’t like it” – that’s waterfall. Likewise, command and control people are using this term, this military competency, organizational competency of who’s our commander and how is our organization under control. Modern organizations, progressive organizations are controlled based on self-organization principles, marching towards a commander’s intent.

If you really want to talk about bad leadership, I recommend that you use better language.

I recommend something like The Leadership Circle Profile, which describes specific competencies that we need from our leaders as well as reactive tendencies. And so here’s what the leadership circle looks like. And if you were to take a 360, it would plot how people perceive your effectiveness because leadership perceived is leadership achieved and versus how you tend to view yourself.

And so you might wanted to have a conversation about not command and control, but:

Are you arrogant? How does that play out?

Are you too ambitious and driven and people can’t keep up with you? And it’s never good enough? Are you a perfectionist?

Are you task oriented or maybe on the relational side you don’t score very well at all? You’re not very much a selfless leader. You’re not very much in balance and keeping composure under stress.

And so these are much better terms to describe positive leadership styles and behaviors as opposed to negative leadership styles and behaviors. And Dave Marquette in his book, he uses the contrasting term leader followers – the old way – I’m the center of gravity and every one orbits around me – versus the leader leader model where we are an ecosystem and network of competent, capable decision makers towards the commander’s vision, the leader’s intent.

Hopefully you can start using more precise terminology to describe what you want out of your leaders so that you don’t just go waving a hand with blanket judgment statements like “you’re a Command and control leader, you’re obviously old school”. Okay, that’s not helpful. If you’re going to have a crucial conversation, use better terminology. I like this, I use it, you might try it.

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