Communicate Up with Executive Teams
Key takeaways from NextGen Center’s leadership panel
Communicating with executives can feel intimidating. Many emerging leaders struggle with questions like: How much detail is too much? When should you push back? And how do you raise concerns without creating tension?
These questions were the focus of a recent leadership breakfast hosted by NextGen Center titled “Communicating Effectively with Executive Teams.” The conversation featured Brian Alvo, Founder & CEO of NextGen Center; Maari Casey, CEO of Uncompany; Paul Jaglowski, partner at Relias; and moderator Jordan Cain.
The panel shared practical insights drawn from their experience as executives, founders and leaders who regularly navigate complex decisions. The discussion reinforced a core theme behind NextGen Center’s professional development programs: strong leadership is about the ability to communicate clearly, build trust, and navigate relationships inside organizations.
Here are several key takeaways for professionals looking to communicate more effectively with executives and decision-makers.
Communicating up requires clarity and preparation
One of the most consistent themes throughout the discussion was the importance of preparation. Executives operate in environments with constant decisions, competing priorities and limited time.
That means vague messages or incomplete context can slow progress.
Instead, leaders should come prepared with a clear understanding of the situation and a recommendation for how to move forward.
“Urgency should come with a recommendation,” one panelist explained. “Don’t ever send a message that just says, ‘Hey, we have a problem.’ Be clear about what’s happening and what decision needs to be made.”
The difference between urgency and panic matters. Panic spreads anxiety and confusion. Urgency signals that an issue requires attention but is still manageable.
Effective communication might look like this:
Explain the situation clearly
Identify what decision needs to be made
Share what work has already been done
Offer a recommendation
This approach helps executives quickly understand the issue and focus on the decision rather than sorting through incomplete information.
Context matters as much as the data
Data is important, but numbers alone rarely tell the full story.
Paul Jaglowski shared that earlier in his career he often brought too much detail into executive conversations. Over time, he learned that leaders typically need the key points first, followed by context that explains why the numbers matter.
“When you have to tell the whole backstory, it usually means you don’t understand it well enough yourself,” he said. “If I’m getting bored after two or three sentences, it’s probably being delivered ineffectively.”
For emerging leaders, this can be a helpful guideline. Instead of presenting every detail, start with the outcome you need.
For example:
What decision is required?
Why does it matter now?
What information supports that decision?
Providing concise context helps executives quickly evaluate the situation and respond.
Understand the pressure executives operate under
Another important reminder from the panel: executives are dealing with pressures that may not be visible to others in the organization. As responsibility grows, so does the weight of decisions that affect teams, customers, and the future of the company.
“Each level gets more overwhelming,” one speaker noted. “You have more responsibility, more people reporting to you and more accountability.”
Recognizing that pressure can change how emerging leaders approach communication. Instead of assuming leaders are ignoring a problem, it may be that they’re managing several priorities at once.
Approaching conversations with empathy and preparation can make those discussions far more productive.
That includes:
Being respectful of time
Bringing clear information
Focusing on decisions rather than problems alone
When both sides understand the context each person is operating in, communication improves.
Ask tough questions and speak up
Many professionals hesitate to challenge executives or raise concerns. But the panel emphasized that thoughtful questions and honest feedback are essential for healthy organizations.
There is often a natural power dynamic between leaders and the people who report to them. That dynamic can make it difficult to speak openly.
But avoiding hard conversations can create bigger problems later.
“We need you to ask the tough question, to say the hard thing,” one speaker said. “There are a lot of layers in organizations, and those questions help leaders make better decisions.”
For emerging leaders, the goal is not to challenge authority for its own sake. Instead, it’s about helping the organization see risks, opportunities, or missing information.
Effective ways to raise concerns include:
Asking questions rather than making accusations
Sharing your reasoning
Focusing on the business impact
When done respectfully, these conversations can strengthen trust rather than damage it.
Know how leaders prefer to communicate
Another key lesson from the discussion was the importance of understanding communication styles. Not every executive processes information the same way. Some want direct debate. Others prefer time to reflect before making a decision.
One panelist shared an experience working with a board chair who welcomed strong disagreement and direct feedback. Once the team realized that approach was intentional, their conversations became far more productive.
“She was very direct in saying, ‘I’m not afraid to challenge you, and I want you to challenge me,’” the speaker recalled.
For professionals working with senior leaders, it helps to observe and adapt to those preferences.
Consider:
Do they prefer written updates or quick conversations?
Do they respond well to data or narrative context?
Are they comfortable with debate or more reserved?
Adapting communication to fit leadership styles can make collaboration smoother and more effective.
Transparency builds trust
Trust is one of the most important elements in executive communication.
Leaders rely on accurate information to make decisions. That means transparency, even when the news isn’t positive, can strengthen credibility.
When discussing difficult situations, one panelist encouraged leaders to approach the conversation from an ownership mindset.
“I’m looking out for the company’s best interests here,” they explained. “There’s nothing personal about this, but I wanted to be transparent about what’s going on.”
Taking that approach demonstrates professionalism and accountability. It also reinforces that the goal is to help the organization succeed.
Transparency may involve:
Sharing bad news early
Clarifying misunderstandings
Correcting inaccurate information
While these conversations can be uncomfortable, they often lead to stronger relationships with leadership teams.
Communication should flow both ways
While much of the conversation focused on communicating up, the panel also highlighted the importance of information flowing throughout the organization.
One practical example involved sharing insights from board meetings with employees. By explaining the reasoning behind major decisions, leaders can create alignment and reduce confusion across teams.
“After a board meeting, we would walk the team through the key points,” one speaker said. “That visibility built a ton of trust and helped everyone understand the why behind the decisions.”
When leaders communicate clearly at every level, teams can focus on execution rather than guessing what leadership expects.
Leadership communication is a skill that develops over time
The biggest message from the leadership panel was simple: communicating with executives is a skill that can be learned.
It requires practice, awareness, and a willingness to adjust your approach.
Emerging leaders can start by focusing on a few core habits:
Prepare before important conversations
Communicate clearly and concisely
Bring recommendations, not just problems
Ask thoughtful questions
Build trust through transparency
These are the types of “people skills” that NextGen Center focuses on in its leadership development programs. While technical knowledge and strategy matter, strong communication often determines whether great ideas actually move forward.
Continuing the conversation
NextGen Center was created to help professionals develop the skills that make leadership effective: communication, self-awareness, relationship building, and thoughtful decision-making.
Events like this leadership panel bring together executives and emerging leaders to share experiences and practical advice that professionals can apply in their own organizations.
To stay connected with future insights and events, follow NextGen Center on LinkedIn or sign up for the NextGen newsletter for updates on upcoming programs, workshops, and conversations focused on the people side of business.
