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It’s fair to say that most of us don’t have a DeLorean to time travel and deliver everything that top stakeholders want before they ask for it.
But, we can work to improve our skillset around executive communication to deliver the best experience in onboarding.
C suite are a type of stakeholder that measure success in specific metrics and they don’t want to have to work for the information.
If you work on this skill, you’ll feel more confident and in turn, so will your top level executives.
Want to know how to manage up? Read down here. ↓
🧪 The Project: Top Stakeholder Communication
You may not be able to provide everything yesterday for C suite but you can stay a few steps ahead by having a plan of action for the best communication.
Step 1: Decode how they operate
Executives are busy people. They're also a unique part of the customer subset.
They process information, make decisions, and communicate in patterns you need to understand.
This is not the time to make assumptions!
Things to think about:
Have a look at their public communication style - LinkedIn posts, company announcements, interview clips.
Ask your main contact: "How do they prefer to receive updates when things are going well vs. when there are issues?"
Research their current priorities - What's keeping them up at night according to recent discussions or industry news?
Understand their decision-making timeline - Do they decide in meetings or need time to process?
You can't manage what you don't understand.
Five minutes of research beats five meetings of misalignment, frustration, and embarrassment.
Step 2: Master 30sec updates
This level of stakeholder wants the headline, the implications, and what they need to do about it.
Make your statements valuable and concise, try something like this:
Current status in one sentence - "We're 40% through onboarding and on track for the March deadline"
Key decision needed - "We need your input on the data migration approach by Friday otherwise the timeline will be delayed by X"
Risk/opportunity flag - "Early user feedback suggests we could expand to the West Coast team ahead of schedule, would you like to green light that today?"
Next milestone - "Our next update will be when integration testing completes on X"
Practice this until you can deliver it smoothly under pressure.
Executives can smell unprepared and “fluffed out” updates a mile away.
Step 3: Stay a few moves ahead
The difference between reactive support and executive management is anticipation.
Aim to have answers ready for the questions they haven't asked yet.
Top concerns - List the three questions they're most likely to ask & prepare data-backed responses.
Proactive milestone updates - Reach out at various completion stages, not just when problems arise.
Options, not problems - When issues emerge, present 2-3 solutions with your recommendation.
Timeline reality checks - Always have backup scenarios ready: "If X happens, here's how we adjust".
When executives see that you're thinking ahead, they stop checking in every five minutes.
It builds a level of trust in your competence as a strong partner during onboarding.
🤓 The Analysis
Demanding executives shouldn’t make you panic.
The executives who seem "scary" are usually just operating with incomplete information, unrealistic timelines, or past vendor trauma!
When you communicate in their language and anticipate their needs from day one, most transform from demanding stakeholders into your biggest advocates.
What to expect by making these changes:
Fewer surprise escalations
Faster decision making
Higher project visibility across the organisation
More expansion opportunities
