Today, we are going to dive deeper into what is my first audience requested topic for this newsletter which is on how to effectively engage with senior stakeholders.

So who are those stakeholders? More often than not they are those busy executives with calendars more complex than tetris, who can make or break your transformation with a single head shake or facial expression. The ones who might use words like "Agile" and "Scrum" in a conversation but sometimes seem to have a different definition or interpretation than you do.

I like to think of engaging senior stakeholders as "dancing with elephants". They are powerful, graceful, commanding respect, and can either be your greatest allies or accidentally squish your carefully garden of Agile practices without even noticing. Learning to dance with them, to move in harmony rather than get trampled, is an art that can make the difference between a transformation that thrives and one that merely survives.

So let's go into some practical approaches that have worked for me and many teams I've worked over the years.

Imagine you've just moved to a new country. You are excited, full of ideas, and ready to contribute, but you don't speak the local language fluently. This person was me when I first moved to Spain in 2008 barely able to say “Hola!” and that's often how it feels when we try to communicate with senior leadership. We are speaking "Agile", they are speaking "Executive." The miscommunication isn't because one of us is wrong; it's because we're using different dialects.

One of the most powerful tools I've used is what I call a "Value Translation Table", I didn’t call this name at that time but I had to name now for the sake of making it easier to reference. It's simple but incredibly effective. Take a piece of paper or whiteboard and draw two columns:

Left column: What you and the team you work values and measures
Right column: How this translates to business value that executives care about

For example:

I once worked with a development team that was incredibly proud of achieving a "zero bug" rate in their sprints. They presented this metric in the first Sprint review where they invited senior stakeholders to join where they responded with blank stares and quickly made signal to move on to the next topic. The team was in very low spirits and wondering what had gone wrong.

Bringing up that topic for the retrospective and as an action item out of it, we created a value translation table, and realized that what the executives really cared about was customer satisfaction and reduced support costs. We then re-framed the achievement: "By eliminating our bug backlog, we've reduced customer reported issues by xx% and decreased support requests by yy%, resulting in approximately $X savings per quarter while improving our App Store rating from 3.2 to 4.6 stars."

Over time, the executives were more and more interested. Same achievement, different language.

My first memory of always presenting something in threes came from my first consulting work and It’s funny how this made up rule applies into so many contexts including in how to translate value. Senior stakeholders are drowning in information. Their attention is the scarcest thing in your organization. That's why it’s important to follow the "Rule of Three" when communicating with them:

Think of it like packing for a weekend trip versus a month-long expedition. With executives, you are always packing light, only the essentials, nothing they won't use, everything with a clear intent and purpose.

See what I did there? 3 points too 🙂

While data matters, stories stick longer than numbers. I learned this lesson the hard way when presenting a detailed metrics chart to a business sponsor of one team I was coaching, proudly showing how the team had improved their predictability over six sprints due to using automation frameworks for testing. I could sense his eyes glazing over and that’s when I switched tactics:

"Remember that production issue with customer Y last quarter? The one you personally made an apology call? That problem could have been caught by our new automated testing framework. In fact, last week, it prevented a similar issue that would have affected most of our customers."

Suddenly, he was engaged. The data supported the point but it was the story that made him care.

Senior stakeholders deal with numbers all day. What they often lack are the stories that give those numbers meaning. When you can provide both we create a compelling case that speaks to both heart and mind.

Another powerful technique is what I call the "Stakeholder Value Contract." It's not a formal document, but rather an explicit conversation about:

I remember facilitating this conversation with a skeptical CFO who had been avoiding the regular transformation update meetings. When asked directly what value he hoped to see, he immediately said, "I need to know the company isn’t wasting money on things nobody uses." This was a revelation! The team had been focusing on velocity and technical metrics in their updates, completely missing what mattered to him.

We agreed that quarterly, we would provide data on feature usage and an estimated cost of developed features, with a specific ROI focus. Additionally, he shared that he preferred summarized information via email rather than joining meetings in person.

The result? He felt at peace, knowing his presence wasn’t required in every meeting because we were giving him what he needed in the format he preferred.

Remember: watch out when you overdo this approach as you might end up in reporting hell, creating custom reports for every stakeholder. Tailor to specific stakeholders according to what you might have mapped on your stakeholder mapping exercise

All the techniques and frameworks in the world can't replace the power of building genuine, trust based relationships with your stakeholders. This isn't about manipulation or politics, it's about connecting human to human.

Some approaches that help build authentic relationships:

Take time to understand what matters to your stakeholders beyond the immediate project or transformation. What are their career goals? What keeps them up at night? What are they measured on?

Make it a practice to have at least one coffee or lunch with key stakeholders outside of regular meetings, with no agenda other than getting to know them better. These conversations often reveal motivations and concerns that would never surface in formal settings.

Trust is built when people are willing to be vulnerable with each other. As coaches or transformation leaders, we can initiate this by being honest about challenges, admitting when we don't have all the answers, and asking for help when needed.

I remember admitting to a client sponsor that a particular aspect of their Agile implementation wasn't working as expected and I shared examples of similar situations I faced before. Rather than becoming more doubtful, he actually opened up about similar challenges he faced at a previous job. That honest exchange kick started a foundation of trust that helped us navigate much more difficult conversations later.

Make sure stakeholders are included in celebrations of success and explicitly acknowledge their contributions. This isn't just about being polite, it reinforces the value of their engagement.

One technique that I love, which to be honest, it’s been a while I don’t use it, is the "ripple effect" acknowledgment: "Your decision to fund the DevOps tooling has enabled the team to deploy 3x more frequently, which allowed us to respond quickly to customer feedback, which has resulted in a xx% increase in DAU."

Engaging with senior stakeholders is indeed like dancing with elephants, it requires respect for their power, awareness of your surroundings, and graceful movements that create harmony rather than conflict. It's not about manipulation or politics; it's about creating genuine alignment between what your teams are doing and what the organization needs.

Remember:

When done well, senior stakeholder engagement doesn't feel like a burden on your transformation, it becomes one of its greatest accelerators. Those elephants that might have accidentally trampled our Agile garden can instead become its most powerful protectors and champions.

What stakeholder engagement techniques have worked for you? What challenges are you still facing? I'd love to hear your stories and questions in the comments!

Keep the elephants dancing! Just be mindful of your toes 😏