The Interpreter's Dilemma

How to take abrupt and/or vague senior-level directives and turn it into team action

Apr 17, 2025

👋 Howdy! Claire here, Founder & CEO of Canopy. I've spent the last decade studying 50+ years worth of leadership research and training 30,000+ leaders. Each week, I distill all my learnings in this weekly newsletter.

Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

This email lands in your inbox at 9:43AM on Monday:

After some consideration, we need to implement a cross-functional AI-augmented human connection initiative across all departments immediately. Can you incorporate this into your team's OKRs for Q2 and pull together a plan by Thursday, for us to review?

-Your CEO

You stare blankly at the screen. The coffee next to you grows cold. The quarterly roadmap was just finalized last week. Your team is already stretched thin on three different priorities. Everyone’s already a bit paranoid of their jobs getting replaced by AI… And honestly, what does a “cross-functional AI-augmented human connection initiative” even mean?

Your eyes dart to the clock on your screen: In less than three hours, you have your team’s weekly sync meeting, and twelve team members will be looking to you for clear direction on what this means for their daily work. You've become the interpreter — responsible for translating this abstract vision into concrete action steps without revealing your own uncertainty.

Sound familiar?

As a CEO myself who has also trained thousands of managers who’ve found themselves in similar situations, necks sore from the proverbial whiplash, I feel deeply for everyone involved. These strategic pivots coming from upper leadership usually emerge from a prudent place: The CEO has seen genuine signals about market changes or competitive pressures that haven’t yet filtered throughout the organization…

But these seemingly out-of-nowhere directives wreck havoc on the frontline leaders who have to find a way to share them with the rest of the team — and implement them.

Your CEO’s good intentions doesn't make your job as the interpreter any easier. You still face the challenge of interpreting abstract vision into concrete action while maintaining your team's trust and momentum.

Let's talk about exactly how to do this effectively.

Beyond parroting

The temptation after receiving a directive like “implement a cross-functional AI-augmented human connection initiative” is to simply repeat those exact words to your team. (That is what they told you, after all!)

But as you've likely discovered, simply parroting executive language rarely leads to meaningful action.

For your team to perform at a high level, they need to somehow internalize what needs to get done. You want folks to act with a sense of ownership, accountability, and proactivity.

After all, the best teams don't just follow directives from the top — they understand the underlying purpose and apply their own expertise to bring the vision to life.

Resonating with a directive, not just replicating it, is an approach that benefits everyone. The senior leader doesn't need to micromanage every detail. Instead, they can focus on demonstrating the shape of what “good” looks like and reinforcing why the work matters. Your team can also feel more freedom to try new ideas, push limits, and in fact come up with even better outcomes that the original directive dictated.

Then, something even more remarkable, and dare I say beautiful, emerges: Work becomes less externally dictated and more internally motivated. Intrinsic motivation arises, which is in fact the strongest source of motivation for anyone.

This is what we aspire to cultivating in our team, as leaders.

The question is, though of course, how do we do that amidst a handed-down senior-level directive?

Here are 5 steps for turning an abrupt and/or vague executive-level directive into team action:

1. Unpack the underlying intent

When executives issue broad directives, there's almost always a deeper strategic reasoning behind them. We must identify that underlying intent, if want any hope of our team internalizing that intent as well.

For example, when your CEO mentions an “AI-augmented human connection initiative,” they're likely responding to industry trends about balancing technological advancement with meaningful customer relationships. Perhaps they've spotted competitors leveraging AI while losing the human touch that differentiates your company.

But it’s hard to know exactly without asking :-)

As a result, instead of accepting the directive at face value, schedule a follow-up conversation with questions like:

“Just so I can align on supporting the outcomes we want, what would things would look like if we were successful at this?”
“To make sure we execute well on this, may I ask what market insights you noticed that prompted this new direction?"
“To understand how we want this to fit together, how do you view the prioritization and alignment of this with our other current priorities?”

These questions help you understand not just what needs to be done, but why it matters. You’ll then get the context you need to make implementation decisions that align with the true intent of the directive.

You’ll also notice that I suggest a opening to these questions, such as “Just so I can align...” and “To make sure we execute well on this…” This preface gives your CEO context as to why you’re asking the question. You’re not trying to question their judgment or authority — you’re merely trying to gain the information you need to make things happen.

2. Breakdown the abstract, ground in the concrete

Once you understand the underlying intent, your next challenge is to turn the abstract concepts into concrete steps your team can execute.

You may want to start by breaking down the initiative into its component parts. In the case of the example above:

What does “cross-functional” mean in practical terms? Which departments need to collaborate, and how?
What specific AI capabilities are we leveraging, and for what purpose?
How do we define and measure improved “human connection”?

Then, you can begin to create some structure that connects high-level goals to specific actions. This might be the flavor of your company’s specific goal framework, such as OKRs. But just to illustrate a more framework-agnostic example:

Goal: Improve customer sales and renewal through AI-human partnership
- Action: Implement AI systems to handle routine inquiries and data collection
- Action: Develop customer stewardship training program for support team members
- Action: Create customer journey maps identifying key moments for human guidance
- Action: Establish metrics that measure relationship depth, not just resolution time

Again, this is merely an example. The key thing here is to breakdown the abstract into components — and then find ways to ground those components into actions.

3. Connect to what’s compelling and relevant

It's one thing to share the actions and distribute the to-dos, but it's another for those tasks to actually matter and connect with your team. You need to find a way to make this initiative personally relevant and compelling to them — and non-threatening.

For instance, your customer support team might understandably worry that an “AI-augmented human connection initiative” signals the beginning of the end for their roles. Instead of brushing past these concerns, address them directly: “This initiative isn't about replacing you — it's about elevating your role from handling repetitive tickets to becoming true customer stewards and guides, especially during critical moments like onboarding.”

Connecting these dots won't happen automatically — not because your team isn't smart, but because there are so many signals in a company that if something isn't explicitly stated, it gets lost in the noise. You need to make these connections clear, relevant, and compelling.

Relevant means how this applies to their job and connects to what motivates them. For your support team, emphasize how AI handling routine inquiries creates space for them to develop deeper customer relationships and more strategic skills.

Compelling means it feels like it matters and is interesting. Something has to be at stake. People don't change their behavior unless there's a clear upside. The best way to make something compelling is to share concrete examples, numbers, and a vision of the future.

For example: “Once we implement this initiative, three months from now our support team will transition to spending 70% on personalized onboarding experiences and proactive customer success. A year from now, we'll have transformed our support team into a strategic consultative function with advanced skills in customer relationships for both new sales and retention — making your roles both more secure and more valuable.”

4. Anticipate and preview how things will feel

As leaders, we sometimes focus so much on the strategic benefits that we forget to address how changes will actually feel day-to-day for our teams. All change includes natural friction.

With this in mind, anticipate what those friction points might be, and be transparent about what the journey will look like:

The transition period: “For the first few months, you'll be doing double-duty — both handling some routine support tickets while also developing your customer stewardship skills. This might feel overwhelming at times, but we'll adjust workloads to make this manageable.”
The learning curve: “Becoming true customer guides requires new skills in consultative communication, product expertise, and relationship building. We're investing in training programs specifically designed for this transition.”
The changing metrics: “We'll be shifting from measuring ticket resolution times to tracking customer success metrics like adoption rates and expansion opportunities. This means your performance will be evaluated differently.”
The emotional journey: “It's natural to feel unsure about giving up tasks you've mastered for new responsibilities that might feel unfamiliar. We'll celebrate small wins along the way and create opportunities for you to share your experiences.”

This level of honesty about the transition builds trust and resilience. Instead of glossing over challenges with vague promises about a better future, you're acknowledging that change is difficult while still maintaining confidence in the direction.

You might even explicitly project how their role might be impacted: “Here's what your typical customer interaction looks like today... and here's what it might look like six months from now as a customer steward.” This concrete visualization helps team members picture themselves in their evolved roles.

By anticipating and acknowledging the full range of experiences — from discomfort with new tools to excitement about more meaningful customer relationships — you demonstrate empathy while keeping the team focused on the journey ahead.

5. Consider your communication format

Remember that your team is bombarded with information from all directions. For any transition to resonate, you'll need to communicate consistently across multiple channels, each serving a different purpose.

For your AI-augmented human connection initiative:

Team meetings: Use these for dialogue, not just announcements. Present a customer journey map showing where AI will handle routine inquiries and where human stewardship becomes critical. Leave time for questions and collaborative problem-solving.
Visual roadmap: Create a simple timeline showing the gradual shift from traditional support to stewardship roles, with key milestones and training opportunities clearly marked.
One-on-ones: These are crucial for addressing individual concerns. Some team members might worry about their technical abilities to work with AI, while others might question if they have the consultative skills for deeper customer relationships. Tailor your message to each person's specific situation.
Peer learning circles: Establish small groups where team members can discuss their experiences during the transition, share tips for working with the AI system, and practice their new stewardship skills.
Success spotlights: Use your team chat or email updates to regularly highlight examples of effective customer stewardship, creating visible models of what “good” looks like in this new paradigm.

Different team members will connect with different aspects of the message. Technical people might want to understand the AI's capabilities and limitations. Customer-focused folks might need examples of what meaningful stewardship conversations look like in practice.

The key is consistency in your core message: “We're augmenting your capabilities with AI so you can evolve into true customer guides, especially during critical moments like onboarding.” This should be the thread running through all communication channels, repeated often enough to stick, but varied enough to stay fresh and relevant.

The most important aspect: Enrollment

The most important thing when translating senior leadership directives is remembering that for people to take action in a lasting way, they have to choose it themselves. They have to enroll.

As Peter Senge discusses in his work, shared vision isn't imposed — it's something people actively choose. Your job as a leader isn't to force compliance but to create conditions for meaningful commitment.

Let's return to that Monday morning email about the “cross-functional AI-augmented human connection initiative.” After following the steps above, imagine this conversation with a senior support team member:

Before interpretation: “So... we're implementing AI. Does this mean half our team is getting replaced?”
After interpretation: “Believe it or not, I'm actually excited about building our customer stewardship program. Having AI handle the basic troubleshooting and billing queries means I can finally develop those onboarding workshops I've been talking about for months.”

That's the power of effective interpretation. You've transformed a threatening directive into an opportunity that team members willingly embrace. You haven't just clarified what needs to be done — you've created a context that allows your team to see themselves as active participants in an exciting evolution, not passive recipients of an imposed change.

The next time you receive a vague directive from above, remember: Your role isn't just to repeat the message from above, or simply assign the to-dos. It's to create the context for your team to operate at their highest level.

And perhaps most importantly, be sure give yourself grace during this process. Even the most skilled interpreters need time to process sudden changes. Do take a moment to absorb the directive yourself before attempting to translate it for others.

I look forward to hearing how it goes for you.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics that help leaders with communicating clearly, including “Effective Communication,” “Operationalizing Vision,” “Setting & Implementing Goals” and “Managing Up.”
🚂 Partner with me to roll-out a leadership training program for your managers to help them coach and keep their top performers.
🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.
🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚