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REPLAY: Leading Through Compression – by Charlie Gilkey

REPLAY: Leading Through Compression - by Charlie Gilkey REPLAY: Leading Through Compression - by Charlie Gilkey
REPLAY: Leading Through Compression by Charlie Gilkey


🌟 While we no longer record the Q&A discussions during our Leadership Strategy , we continue to record the opening teaching. Enjoy a special preview of what I shared about navigating November's compression. If you want to see the complete teaching and take part in upcoming sessions, consider upgrading to join us live next .

November compresses everything. Time. Energy. Attention.

The calendar says eight weeks remain in the year, but with the holidays and events the reality is closer to four or five. The temptation is to harder, do more, every hour. But November isn't the time for heroics. It's the time for precision. Strategic choices about what finishes, what ships, and what seeds for next year.

During this month's session, we explored how you can help your team manage the tension that comes when trying to get everything done before the clock runs out while also enjoying the season.

Re-evaluate your strategic horizon. The year feels like a natural endpoint, but it's often too short to judge if a strategic initiative is actually working. Treat year-end as a checkpoint, not a finish line.

Give your team permission to release. Just because you committed to something in May doesn't mean it's still the highest-impact work. Without explicit permission, teams stay locked onto projects that drifted far from your key .

Shift from activity to outcomes. Your team's long list of completed tasks can mask a lack of strategic progress. Focus conversations on the metrics and results that your strategy.

your team to truly disconnect. When people are half-on and half-off, nobody wins. Plan now for coverage, grace on the backside, and gradual return-to-work transitions so people can actually rest instead of returning depleted.

This month's Q&A also covered:

  • Tension is not conflict: Growth requires discomfort, and awkward conversations are part of the work, not a signal to stop.

  • Short-term vs. long-term thinking: When pressure mounts, the instinct is to do the work yourself but in training creates capacity long-term.

  • Telling, teaching, and training: Recognize that training (transfer of skills) is the hardest and takes longest — factor this in when planning team capacity.

  • Values alignment: When team friction surfaces, check if different values are driving the disagreement.

Our next Leadership Strategy Session will be on Wednesday, December 3, 2025, at 11:00 a.m. PST: Closing with Integrity, Not Exhaustion.

Premium subscribers can the full opening teaching and access below 👇🏽 all related shared during the call.



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