Continuously improve with Agile coach Kimbaly St. Matthew-Daniel

Illustrated by Matt Peet

You likely know when your car is struggling—even if you know nothing about cars and cannot articulate what is wrong, you feel it in the steering wheel, hear it in the stutter of the engine or smell it through the vents. Struggles in development organizations often go the same way. People know when things aren’t working cohesively, productively or at all. Teams aren’t hitting deadlines. They’re working in different directions, or with different methodologies. Tech debt is piling up.

But it’s not always apparent that a process or a strategy is to blame. That’s when an organization is ready for what Agile coach Kimbaly St. Matthew-Daniel calls their transformation journey.

“If those things are happening, they're telltale signs that the process needs to change and things need to be refined,” she says.

Kimbaly started her career as a project manager and business analyst before joining 3M when they were starting conversations about a natural transformation. They leveraged her, as a product analyst, to take on a product ownership role and helm the change from Waterfall to Scrum. From there, she has taken on positions as a Scrum master and an Agile coach.

“I have tapped into something that I love,” she says. “I love coaching. I love helping, and not just at the development team level, but across the enterprise. I don’t like to get hung up on process, but I do like to focus on the people I’m working with and ultimately for. I want to coach them to be effective. I want to make sure they have what they need in order to be successful.”

In this interview, Kimbaly draws out her guiding philosophy about shifting organizational mindsets before digging into the how-to of creating change in a company through asking questions, targeting coaching efforts according to knowledge and expertise, and communicating through messes head on. She also explains how change as a constant creates stability, and how the greatest transformations are guided by the people who invest themselves in the movement.

Change the mindset, change the organization

Kimbaly offers one high-altitude principle for anyone looking to transform a company or a team: If you want to change the organization, you need to change the mindset.

And in most organizations, you can accomplish that by refocusing on products more than projects.

“You want to focus on products,” Kimbaly says. “Most teams, when they work on a project, they think it’s just a feature. But we don’t have to work at such a granular level, focused on small subsets of feature work.”

You can think of a typical hypothetical button problem. Many development teams think they’re working on a series of single problems: when you click this button, we need X to happen. But that’s a siloed mindset, even if the teams are integrated. The mindset shift Kimbaly means is to recognize (and take ownership in) a team’s participation in the entirety of an app.

“A lot of companies are saying that they want to become more product-focused because that's where the value is, and that's where the longevity is,” she says. “That keeps them competitive. When you're project-focused, you're not really worried about those types of things. And you're not having those vital conversations with marketing, and with the customers to get them ramped up and bought into the idea.”

Leadership within an organization needs to instigate these conversations at every scale. And it’s up to tech leaders to make the changes to old patterns that can actually facilitate these changes in mindsets.

Ask the right questions when things aren’t working

Because leaders and their teams may not be able to articulate why their current processes aren’t humming along, Kimbaly first assesses what they know and how they see their way out of the trouble.

She wants to know: What’s the knowledge across individuals? (For example: who knows what Scrum is, or who can explain what Agile looks like?) How effective do they think different directions would be? And what outcomes would they expect from those directions?

These answers are much more helpful for shaping a change strategy than assessing everything that is not working. “You don’t want to come in and tell everybody that what they’re doing is completely wrong,” Kimbaly says. “You want to get buy-in from those people who have been doing it.”

In this way, change becomes a movement motivated from within, not a mandate set down by herself or by a leader in the org. Assessing existing skills and discussing ways forward sets an expectation of growth toward a new methodology, rather than criticism of the old one.

Establish baselines and coach to target audiences

Once you understand the level of expertise across individuals and across teams, you’re set up to coach more effectively. People who demonstrate a familiarity with Agile, for instance, might become subject matter experts—they may be interested in being certified, or you may wish to establish select roles and responsibilities according to their existing skills and knowledge.

“You have your product owners, your scrum masters and the managers who understand what those are, what the expected outcomes are and can ensure that people are accountable,” Kimbaly explains.

Then after identifying roles, you can identify events—Kanban boards, standups, scrums and so on. More than that, you can identify who is involved and what they can expect. “What kinds of conversations should you have?” she offers. “What are some of the things you should look out for? How should you escalate impediments? What does that look like?”

One of the impediments of a stagnant workflow is that people don’t always have a clear sense of expectations. Establishing expectations clearly gets your team invested and excited in the new program. “They’re rallying around what their roles are,” Kimbaly says. “They’re rallying around who’s responsible, who’s accountable. And then they're spinning up these events and they're putting them on their calendar and they're identifying a person who's going to help facilitate those conversations.”

Whether people are certified or not, they’re interested in the game plan because they are now part of something different—a different movement.

“They see the autonomy that they have,” she says, “because again, you're not coming in and telling them that what they're doing is wrong or that all of these things have to change. You're allowing them to feed you so that they have an idea of the direction they can go in. They’re not being led. They're actually a part of that process. That's really important whenever you're taking a company through a transformation journey, because you want to make sure that they understand where you're taking them and that they are part of that journey as well. They contribute to that journey until they know exactly where they want to go and how they see themselves better going there. All I'm doing is helping set up the pieces.”

Understand needs in order to fulfill them

That idea of targeted coaching deserves more clarification. Kimbaly understands that learning is not one-size-fits-all, and even something like Agile looks wildly different in different contexts. “I want to make sure I’m coaching to the organization,” she says. “What are the goals we are trying to hit? How are we going to best hit those? What do you need? All to better understand how we’re going to deliver, and how to provide different tools to better meet those needs.”

The needs she considers are not only individual or team needs, though those are of course critical. She makes sure everyone is focused on the bottom line, as well—essentially, the company’s most basic need is a successful bottom line.

“Whether we’re talking about scope creep or the burn-up, they need to feel like they’re contributing to the bottom line while also making it very visible what the bottom line is,” she says. “Having those conversations is important. You want to still push the needle toward change, while also bringing value to the company. You want to help them tie that together.”

Kimbaly finds those conversations particularly rewarding when she helps teams bridge the gap between what change looks like from their perspectives and what it means for their company, as well.

Address messes head on

It’s simple but it’s true: communication makes the business world go ‘round. And it’s also true that tough conversations are difficult to have. Change is inherently challenging, so Kimbaly aims to ensure that people keep talking.

“I make adults talk,” she says. “I encourage adults to connect with professional conversations. That’s a large part of what I do: When things get messy, I’m going to encourage adults to have adult conversations.”

Kimbaly puts it another way, too: Let’s speak to the mess.

“Address the mess,” she reiterates. “Let’s focus on change. Let’s change the process.”

Just because a team is using a well-tested process doesn’t mean it’s the right process for them. Regular ol’ vanilla scrum might not facilitate the right conversations to identify impediments for a given team. If so, switch it up.

Meetings, naturally, are natural targets for reinvention. Starting off straight-up with organizing them better makes powerful differences. “I’ve had a lot of success with having well-organized meetings,” she says. “They’re scheduled appropriately, you have the right people there. You're not stepping on a lot of people's calendars, and you are having really important, effective conversation. You come in with an agenda. And then you're walking away with some really good action items, and you’re accountable to them.”

She also believes in making meetings fun—or at least interesting. She has started meetings with jokes. She also aims to break up long or necessary-but-boring meetings to avoid burnout and keep good conversation coming. After all, changing the process isn’t only about big methodological strategies, but switching up attitudes and practices to keep people involved and invested in the long term.

Create stability through change

It’s one thing to get team members’ buy-in and enthusiasm for change up front, when the newness and the potential for growth are so high. Kimbaly works with most clients for the first three months of the transition and sees the excitement first-hand. It’s another thing to maintain that investment over longer timeframes.

Importantly, and perhaps counterintuitively, she points to how change itself creates stability over time.

“You’ve been at it for a year and they are a well-oiled machine, doing all the right things, but feeling stale,” Kimbaly explains. “The numbers are good, but are they happy? Are they really producing to their max capacity? And how do you tap into that? You change things up.”

After the initial wholesale changes of a transition journey, the changes don’t need to stay that extreme. You don’t have to change your tools every three months. (Truth is, that’s usually not a good idea.) But you can change up how meetings are structured, the order in which they’re held or the types of conversations on their agendas.

A lot of those small alterations can contribute to overall success and stability. After all, the longevity of a product in the market is often correlated to its ability to iterate, adapt and change. Why should development teams be any different?

Kimbaly offers an example she experienced during the Covid pandemic: dress-up Mondays. “It was a typical stand-up,” she says, “but everybody showed up on camera dressed up. A typical stand-up, but in cowboy hats and prom dresses. Anything you can’t wear, that’s been in your closet for years, bring it on your Monday call.”

And the best part—because it ties together her entire philosophy of teams driving their own transformations—is that the idea came from the team. And it worked so well because what they were saying without saying it was that they missed people, and they wanted to connect with each other.

“It’s just that little bit of difference, that little bit of connection where we just laugh because it’s not the norm,” Kimbaly says. “That reenergizes them and provides this extra boost.”

Final thoughts: Listen instead of prescribing

Every organization is going to have different problems and different goals. Different preferences and dislikes. That’s why Kimbaly doesn’t recommend the same strategies for each company she coaches. Her advice for tailoring her approach is simple: Listen.

“My advice is to listen to them and just be open to change,” she says. “Don’t be prescriptive. Listen to the team, listen to the business, listen to the way they move. Interview as many people as you can, sit in on meetings. Because you find people who are silently screaming for attention. They need the coaching, they need the guidance and the mentorship.”

And then remember your role as the leader of the revolution, whether you’re a tech lead or a transformation coach, is not about enforcing new structure. Instead, it’s about responding to the needs you hear from the organization and guiding the discovery process for growth.

“You may be the person to help start or continue those conversations,” Kimbaly says, “but don't be surprised if valuable input comes in from a different direction. In your servant leadership role, listen to the people who you’re helping, listen to the organization and you'll be in a really good place.”