Communicating Strategy Execution Updates To The Team

Most leaders over-communicate and under-inform. They send 47 Slack messages when they needed to send one structured update. They ping people throughout the week about things that could wait. They mistake activity for alignment. Here's what changed everything in my company: I stopped managing in real-time and started managing in rhythm. Every Sunday, I send one newsletter to my team. It's called "Slay the Week." And it contains everything my team needs to execute without me: • Active marketing campaigns (current + upcoming), so nobody's asking "wait, what are we launching?"    • Current client count vs. last week: Immediate data. Up or down. What needs to happen this week.    • Team scorecard link: Our data dashboard. Always accessible. Never lost in a thread.    • Wins from last week: What worked. What we're celebrating.    • Opportunities from last week: What the data revealed. Where we're pivoting.    • Important announcements: New hires. Policy changes. Decisions made.    • Team out of office. Who's unavailable, and when they're back.    • Leadership meeting agenda: What we're discussing. What needs to be prepped.    • Quick hits by department: Fast, tactical items that don't need a meeting or a Slack thread. One newsletter. One document. Every Sunday. My team starts Monday with clarity, not questions. They know what's happening, what's changing, and what they own. The result? Fewer meetings. Fewer interruptions. Faster execution. Because when you architect communication instead of scattering it, your team stops reacting and starts building. This is what operational sophistication looks like. Not more tools. Not more touchpoints. Just better structure. Check the comments for my video walkthrough of the entire system and download the template.

To become a great tech leader, you have to communicate meaning. Are you saying something meaningful or only providing data? While leaders love "data driven," it is critical to communicate why the metrics matter. All leaders give status updates; strong leaders connect them to the big picture. Here is how successful executives deliver status updates: As a busy leader, it’s easy to fall into the habit of sharing updates that focus on tasks and metrics, like: ▪️ “We’re 70% done” ▪️ “X feature is live.” But great executive communication isn’t just about what is being done, it’s about why it matters. Without that connection to purpose, your team will lose focus, motivation, and alignment. When we delivered streaming for the Paris 2024 Olympics at Warner Bros. Discovery, our deadlines were fixed and the stakes were global. We couldn’t just share milestones to keep everyone engaged and in sync; we had to make sure everyone understood WHY the milestones were important in the grand scheme of the project. This involves providing answers to questions like: ▪️ Why is X feature critical to the audience experience? ▪️ Why does it matter to the business? ▪️ Why are certain trade-offs necessary to meet deadlines? For the Olympics, communicating the “why” ensured that the engineers, product teams, and operations staff shared a common purpose: delivering an excellent experience for millions of viewers across 47 markets. When done right, creating a shared purpose makes the work your team does about more than just “getting it done.” To create that shared purpose for your team, here are three lessons tech leaders can use: 1) Frame communication around purpose and impact. Help your teams see how their work drives customer value and/or advances business goals. It’s not enough to tell them what to do, tell them why it matters. 2)Ensure alignment across cross-functional teams. Different teams bring different perspectives, so bridge those gaps and make sure everyone is moving in the same direction. 3) Use regular updates to reinforce the bigger vision. Status updates should provide objective benchmarks, but they should also anchor progress back to the larger goals. Many leaders mistake communication for a “soft skill.” In reality, it is a strategic advantage. Master telling the story of the broader initiative and your team will outperform anyone who simply follows orders. Leaders - How do you communicate broader purpose to your teams?

Framework Friday!  Keeping people in the loop. I had a great question recently from a coaching client about communicating things to the team. They had recently whiffed a bit on communicating something important to the team and were interested in helping themselves avoid this mistake in the future. I’ve found over the years that there are broadly four categories of things that require proactivity around how to communicate them.  Those four things are 1. Money - from big deals to new logos to financing and exit events. Money is never the purpose, but it is the oxygen. It’s what allows the business to operate, and people generally want to know what's up. 2. Initiatives - projects, new initiatives, or focused buckets of work that impact the company at large or big pieces of your organization. These efforts are usually spun up for a reason, and it’s critical to have a plan in place to help folks understand why and what we expect. 3. Products - new products, adjustments to products, product deprecation. Communicating when and why helps everyone feel fully a part of the team. 4. Leaders - new leaders or departures. These are probably the most likely to be speculated about and to fire up the rumor mill. The rumor mill absolutely sucks. Get out in front of these always. So now that our consciousness is raised about the kinds of things that will likely require us to communicate, what does a communication plan even look like?  A straightforward proposal: - What is the message - what are we actually going to say and why are we saying it? Generally speaking it’s best to make clear what’s changed, then to focus on the future - ie what will things look like as a result of this change, and to do your best to tell people why things are changing or happening. Be sure every word has a clear purpose. - Who needs to know - not everyone needs to know everything. Sometimes choosing to communicate more broadly represents a distraction for adjacent parties or groups. That said, always bias toward inclusion. Better to make the over-communication mistake than the under-communication one. Also, be conscious of the order of operations. For a C Level change, for example, first notify the C Level group, then notify that new C Level’s team, then perhaps an affected region or function, and then the whole company.  - What are the channels - in the above example, we probably want to notify the C level group and the new C Level’s team in person. After that, we can use more scalable communication channels like all-hands meetings, email, and internal message boards. Assume any email will be forwarded. Overall, the goal is to be conscious and intentional about choosing the message, the audience, and the channel. I've found that creating a shared document with relevant stakeholders in which each of these things is made explicit through documentation and collaboration, is probably the best way to bring this framework to life. What would you add, subtract, or change? #WTWYW

Cascading communication is one of the most underrated leadership skills in Enablement - and while it's not particularly challenging to do, common sense isn't always common practice. One of the things I love most about being in enablement is how we are one of the most collaborative functions and help connect the dots for seemingly random insights from different business units. 🤔 Over the past few months, I’ve been focused on strengthening how we translate leadership insights into clarity, alignment, and momentum for our teams. And the more I practice it, the more I see this truth: Cascading isn’t forwarding information. It’s sense-making. It’s leadership. Here are a few principles that keep rising to the top for me: 🔹 Cascade when the message impacts priorities, clarity, or performance — especially when new frameworks, strategy shifts, or language emerge at the leadership level. 🔹 Don’t cascade when information is directional, confidential, or likely to create confusion without actionability. There is such a thing as "too much". A leader's job is to filter, translate, contextualize and amplify. 🔹 Leaders must make judgment calls that protect psychological safety. Your team doesn’t just need to know what was said — they need to understand the why and the so what. 🔹 Context is the accelerant. Build cascade moments into your operating rhythm. Create space in your team meeting or recurring communication strategy. 🔹 Bring people along the journey. I’ve found huge value in consistently sharing insights from exec forums, cross-functional discussions, and 1:1s with senior leaders back with my team. But I find even more value in crowd-sourcing from my team to cascade UP. Inviting teams to submit questions before senior leader roundtables — and then sharing back implications — has meaningfully increased alignment and trust. And the data backs this up: 📊 86% of business leaders agree that greater transparency leads to higher trust within the workforce (Deloitte Global Human Capital Trends, 2024) Transparency → Trust → Engagement → Performance. In Enablement, where clarity fuels execution, this becomes even more important. I'll share the visual model Curious to hear from other Enablement people leaders: 👉 How do you cascade information to your teams today? 👉 Where have you seen it accelerate alignment or clarity? 👉 What’s one insight you wish more leaders would cascade intentionally? 👇Drop your thoughts below — I’d love to learn from your playbook too. #enablemententhusiast #cascadingcommunications #clarity #leadership

Here’s a lesson I had to learn the hard way…and something I find myself repeating regularly to my team: If you’re not actively communicating progress, people assume there isn’t any. Even if you’re deep in the work. Even if things are actually moving forward. Even if you’re heads-down solving real problems. Silence creates a vacuum—and in that vacuum, people rarely assume the best. They assume you’re stuck. Or stalled. Or overwhelmed. Or….worst of all, not doing anything. They start asking: “What’s going on with that?” And you’re suddenly on the back foot, defending instead of leading. I’ve had moments where I thought, “Why are they micromanaging me and checking in so much? Don’t they trust me?” But looking back, I wasn’t giving them anything to reassure them or provide confidence that “I’ve got this”. So now, I default to visibility: • A quick update in a Teams chat • A weekly email with what’s changed, what’s blocked, what’s next • One slide that tells the story clearly and simply It’s not performative and it doesn’t take long. It’s strategic. Because communicating progress—especially when you’re doing the leg work behind the scenes, a tricky phase, or a quiet stretch—builds confidence, keeps those relying on you aligned, and clears the path for you to move faster. I learnt that, if you want to be seen as a strategic operator, don’t just do the work. Create a drum beat.

A founder I work with recently told me something that hit hard: "I feel like I'm either micromanaging... or completely in the dark." We dug into how she was delegating projects to her team. The handoffs weren’t the problem, it was the follow-through. She’d assign a task, wait, and then wonder: Are they working on it? Are we on track? Do they need support? Her only feedback loop was silence… until something went wrong. So I showed her a system I often share with clients; one that replaces chasing updates with predictable communication. Here’s the core of it: ↳ Start by clearly explaining the update process. ↳ Ask for weekly updates; nothing fancy, just a consistent rhythm. ↳ When you get the update, respond with a quick thank-you and real feedback. That’s it. Simple. Repeatable. And most importantly, proactive. She implemented it that week and within days: ✅ Her team was updating her without being asked. ✅ No tension. No guesswork. Just momentum. If you’ve ever felt like you’re managing in the dark, maybe it’s not your team... Maybe it’s the system behind how you communicate. Want the framework I shared with her? Drop a “SYSTEM” in the comments, and I’ll send it your way. This is exactly what I help small business owners do; build simple, repeatable communication systems so you don’t have to micromanage or operate in the dark. #systems #leadership #business #strategy #ProcessImprovement