Most major announcements fail not because of poor messaging, but because leadership never aligned on what they were communicating. Leadership decides on a major change. They work out the logistics and timing. Communications gets brought in to develop materials and determine audiences. Rounds of review and revision happen. The announcement goes out. Then the confusion begins.
I see this pattern constantly. Communications produces draft materials that go through multiple rounds of leadership review and sign-off. Leadership debates word choice and phrasing. What they rarely do is step back and discuss the fundamental questions that determine whether the communication will succeed or fail. They debate wording and phrasing without ever discussing what the message needs to accomplish or how it will land.
The following five questions uncover the misalignments that create communication failures. When leadership can answer these clearly and consistently, the actual drafting becomes straightforward. When they can't, no amount of wordsmithing will fix the underlying problem.
I learned the importance of alignment while working on a seven-year data migration that impacted thousands of employees and clients. With that scale and timeline, keeping leadership aligned on what we were communicating at each phase was critical to success. I've seen the same dynamic play out in nonprofits navigating leadership transitions and social organizations announcing program changes. The scale varies. The underlying challenge doesn't.
1. What do you want people to understand from this?
This sounds simple. It is not. I ask this question in almost every engagement, and the answers around the table are rarely the same. One executive thinks the announcement signals growth. Another thinks it signals stability. A third believes it's about efficiency. They've all agreed to the decision itself, but they haven't discussed what that decision means.
The problem compounds when you ask them to explain it without corporate language. Strip away terms like "strategic realignment" or "optimizing our portfolio," and ask what's changing. This is where the real disagreements show up. If leadership can't explain the decision in plain language to each other, employees will interpret it in a dozen different ways.
I see this happen in almost every initial conversation. I'll ask the leadership team to explain the decision without using any corporate terms. There's usually a pause. Then someone starts, realizes they're slipping back into corporate language, and tries again. It becomes clear they haven't had this specific conversation with each other yet, even though they've spent hours discussing the decision itself.
This question forces specificity. Not what you hope people might understand, or what you'd like them to focus on. What do you need them to understand? What's the one thing that, if they walk away with nothing else, means the communication succeeded?
2. What will people assume this means that you don't intend?
Every significant decision lands in a context. Employees remember the last restructuring and know which competitors just had layoffs. They've heard rumors and are worried about the economy, their job security, or whether leadership knows what they're doing.
Leadership often operates from their own context. They know this decision is different from the last one. They know the strategic reasoning. They know what's not changing. Employees don't have that context, so they fill in the gaps with their own assumptions.
I've seen this gap across different contexts. In large-scale technical initiatives, leadership understands the improvements while clients hear 'data migration' and assume disruption. In nonprofits, a 'strategic refocus' signals growth to the board, but sounds like budget cuts to program staff. The interpretation gap exists regardless of organization size.
The question I always ask is not just what people will assume, but who will assume the worst-case scenario and why. Usually someone at the table knows exactly who that group is. They just haven't said it out loud yet.
This question identifies the gap between what you mean and what people will hear. The goal is not to control interpretation. The goal is to anticipate misinterpretation and decide whether you need to address it directly in the communication or accept it as an inevitable cost of the decision.
3. Who needs to hear this first, and in what order?
Sequence matters more than most leadership teams acknowledge. Announcing simultaneously to everyone feels fair and transparent. In practice, it often creates more problems than it solves.
Certain groups have legitimate reasons to hear first. The people most affected by the decision need time to process before they're expected to explain it to others. The people responsible for implementation need to prepare. Key stakeholders whose support you need should not learn about major changes the same moment everyone else does.
Sequencing matters whether you're coordinating across thousands of employees or a staff of twenty. The teams implementing changes need different information than the people affected by those changes. In a nonprofit, that might mean telling program directors before announcing to funders. In a larger organization, it might mean regional rollouts. The principle is the same.
I ran communications for a social justice organization working to hold judges accountable. We had to coordinate messaging across grassroots organizations, attorney groups, and the public. The attorneys faced real professional risk. Sequencing wasn't theoretical. We had to think through several different angles. Who needs to hear our analysis first? Who needs time to prepare for questions? Who faces consequences if they're caught off guard? Getting the sequence wrong meant either losing attorney support or letting judges get ahead of the narrative.
The question is not who deserves to know first. The question is who needs to know first for the communication to succeed. That's a strategic decision, not a political one. If you can't articulate why a particular sequence serves the outcome you need, you probably haven't thought through the communication carefully enough.
4. What questions will this announcement create that you need to be ready to answer?
Most announcements generate predictable questions. What does this mean for my role? What happens to the people affected? When does this take effect? Why now? Why this approach instead of alternatives?
The failure happens when leadership doesn't prepare answers before the announcement goes out. They assume they can address questions as they arise. Then the announcement goes out, questions flood in, and different leaders give different answers because they never aligned on what to say.
I ask leadership teams to list every question they can imagine employees asking. Then I ask which questions they can answer now and which they genuinely can't. The ones they can answer need to be documented and distributed to everyone who will field questions. The ones they can't answer need a consistent explanation of why not and when more information will be available.
I learned this while working on campaigns and advocacy work. When you're asking people to vote out a sitting judge, the questions are predictable, but you still have to prepare answers. What did this judge do? Why now? Who decided this? We had to prepare consistent answers for every stakeholder group, or risk people improvising responses that undermined the strategy.
This preparation sounds basic, but it rarely happens. Leadership assumes their managers will figure it out. Managers assume they'll get guidance. Nobody gets clear answers, so everyone improvises. The result is inconsistent messaging that erodes trust faster than the original decision ever could.
The most common pushback I get is "we can't answer that yet." My response is always the same. Say that. Say you don't know and when you'll have more information. What you can't do is pretend the question won't come up. Employees appreciate the honesty far more than they appreciate a non-answer disguised as corporate speak.
5. What will you do if this announcement lands poorly?
Leadership teams resist this question. They've spent weeks making a decision and preparing to communicate it. Nobody wants to plan for failure. The question feels pessimistic or like it invites problems that wouldn't otherwise occur.
However, every significant announcement carries risk. Employees might react more negatively than anticipated, or key people might leave. Stakeholders might push back. The media might frame it in ways you didn't expect. These aren't hypothetical concerns. They're predictable possibilities.
Planning for a poor reception doesn't mean you expect failure. It means you've identified the early warning signs that something is going wrong, and you've decided in advance how you'll respond. Will you hold follow-up sessions? Will you adjust the timeline? Will you issue clarifications? Who makes those calls, and how quickly? Without this planning, organizations spend days trying to coordinate a response while confusion spreads and trust erodes.
This question is about preparation, not pessimism. You're not planning to fail. You're planning to respond quickly if the communication doesn't land as intended.
When These Questions Go Unasked
The pattern is always the same. Leadership makes a decision. Communications drafts an announcement. It goes through review and revision. The announcement goes out. Then leadership spends the next two weeks cleaning up the mess. They manage confusion. They answer predictable questions. They clarify what they should have said in the first place.
The cost is not just time. Every round of clarification erodes credibility. Every inconsistent answer damages trust. Every day that people operate with incomplete or incorrect information affects performance and morale.
These five questions take time to answer well. They require actual discussion, not quick agreement. They reveal disagreements that leadership would often prefer to avoid. This is precisely why they're valuable. The disagreements exist whether you discuss them or not. Better to reveal them before the announcement than discover them when employees are confused, and you're scrambling to respond.
How to Use These Questions
These questions work best when asked early, before any drafting begins. Gather the leadership team. Work through each question. Document the answers. Ensure everyone can articulate the same core points.
If you find yourself struggling to answer any of these questions clearly, that struggle is information. It tells you where the misalignment exists. That's not a problem with the questions. That's the problem you need to solve before you communicate anything.
Once you have clear, consistent answers, the actual communication becomes simpler. Your messaging can be direct because you know what you're trying to say. Your timing can be strategic because you've thought through sequencing. Your response plan can be swift because you've anticipated what might go wrong.
This is the work that happens before the work. It's not about wordsmithing. It's not about perfect messaging. It's about ensuring leadership is aligned on what they're communicating before anyone starts drafting how to say it. Get this right, and everything else becomes easier. If you skip it, no amount of good writing will save you from the confusion that follows.
If you're facing a major announcement and need someone to help you work through these questions before drafting begins, that's exactly the work I do.