How to Manage Up: Communication Strategies for Director-Level Roles
Designed for Director-level leaders in technology organizations who recently stepped into managing cross-functional senior teams and need to influence C-suite or Board stakeholders. to spark real collaboration and high-energy learning.
A 90-minute virtual interactive workshop for directors in mid-to-large tech firms. Participants manage multiple managers and must balance advocating for their teams with aligning to rapidly shifting executive priorities. Their pain points include not being heard when raising critical issues, feeling uncomfortable pushing back, and uncertainty about how to tailor messages for execs pressed for time.
Inbox Mystery: C-Suite Editions
Open with a ‘mystery email’ exercise: Flash a real anonymized email sent to a CTO or CEO on screen (with permission). Ask, 'What do you notice about the subject line? The tone? How do you think the exec will react?' Invite quick popcorn reactions in chat or aloud.
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Why this works
Real examples spark curiosity and lower anxiety. Executives rarely share their true inbox contents, so this peek builds authentic interest and sets up the need for skill shifts.
Assumption Autopsy: Upward Feedback
Use a live poll to reveal a common misconception: 'True or False—Executives don’t want to hear problems, only solutions.' Show instant poll results, then share research/statistics that debunk this myth. Invite a brief group chat on why this belief persists.
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Why this works
Surfacing and challenging misconceptions re-frames learning targets and gets everyone on the same page—essential for adult learners who bring lots of prior experience.
Safe Starts: Executive Preferences Bingo
Hand out a quick, fun ‘Executive Preferences Bingo’ sheet with items like ‘Prefers Slack over Email’, ‘Wants data up front’, ‘Hates attachments’, ‘Asks for the bottom line first’. Invite everyone to mark what they’ve actually observed from their execs. Small prizes for first bingo.
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Why this works
A playful, low-risk way to surface participants’ real-world observations and normalize the diversity of exec communication styles. Bingo format keeps it light and accessible.
Full-Contact Update Pitch
Split the group into breakout trios. Each director gets 90 seconds to deliver an urgent update to a mock ‘CFO’ and ‘COO’, who role-play executives with challenging personalities (‘impatient’, ‘asks for ROI immediately’). Rotate roles and cheer on the best pivots and succinct messaging.
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Why this works
Practice under playful time pressure ramps up energy, reveals real communication gaps, and gives immediate peer feedback—perfect for kinesthetic learning.
Leadership Dilemma: When to Push Back
Present a real-world dilemma: ‘You know a new product launch is risky, but your CEO is pushing for speed. Do you raise concerns now, later, or not at all?’ Poll the group on their instinct, then reveal 2-3 real director approaches—successes and failures.
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Why this works
Anchoring in a genuine dilemma shows there’s no one right answer, builds psychological safety, and encourages nuanced thinking.
My Executive, My Strategy
Invite each director to jot down (privately) the name of one specific executive they find hard to influence. Prompt them to outline one new approach—based on today’s session—they could use in their next interaction. Pair up and share strategies for 2-minute peer coaching.
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Why this works
Active reflection and personal application ensures transfer; peer coaching deepens accountability without putting anyone on the spot.
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