Leadership Transformation: Signs You’re That Boss & How to Evolve

By Shelby Brennan
November 4, 2024

Tomorrow's Leader (Where You're Heading): Focuses on outcomes Sets clear boundaries Empowers decision-making Values results over presence

Let’s be real: If your team’s Sunday night ritual involves anxiety-checking Teams messages, you might be that boss. The one whose name in the notification center makes hearts sink. If your leadership style triggers more dread than drive, it’s time for a change. 😬

The Boss Behavior Reality Check

Quick quiz! Guilty of any these classic power moves?

  • Sending Teams messages at 10 PM with “when you have a minute…”
  • Turning “quick catch-ups” into hour-long status reports
  • Making every email HIGH PRIORITY (because everything is urgent, right?)
  • Responding with single letters to thoughtful updates

Sound familiar? You’re not alone – but you can do better. 🎯

Transform Your Leadership Style

The Micromanager’s Makeover

Old Boss Move: “I see you’re ‘Away’ on Teams. Where are you?”

Leader Move: “Let me know if you need any resources to hit your goals.”

The Credit Collector’s Transformation

Old Boss Move: “Thanks to my leadership, the project succeeded”

Leader Move: “Alex and Jordan’s innovative approach made this possible”

The Urgency Addict’s Recovery

Old Boss Move: “URGENT UPDATE NEEDED NOW!!!”

Leader Move: “Priority: Medium | Due: EOD Thursday | Context: Client meeting Friday”

Real Impact on Your Team

Under Bad Boss Energy:

  • Creativity dies (because who risks new ideas under constant pressure?)
  • Innovation stalls (fear and micromanagement kill experimentation)
  • Trust evaporates (constant monitoring breeds resentment)
  • Burnout rises (Sunday scaries become everyday scaries)

Under Real Leadership:

  • Solutions flourish (because people feel safe to experiment)
  • Teams collaborate naturally (trust breeds partnership)
  • Psychological safety soars (open dialogue becomes the norm)
  • Energy rises (work becomes energizing, not draining)

Your Leadership Upgrade

Today’s Boss (Time to Evolve):

  • Lives in Teams status updates
  • Expects instant replies 24/7
  • Makes every decision
  • Measures hours online

Tomorrow’s Leader (Where You’re Heading):

  • Focuses on outcomes
  • Sets clear boundaries
  • Empowers decision-making
  • Values results over presence

Quick-Win Leadership Experiments

  1. The 24-Hour Rule Challenge: No “urgent” tags for 24 hours Why: Learn true priorities versus perceived emergencies Win: Better time management for everyone
  2. The Power-Share Challenge: Next three team meetings? Your team leads them Why: Build confidence and showcase hidden talent Win: Fresh perspectives and engaged team members
  3. The Trust Test Challenge: No Teams status checking for one week Why: Focus on outcomes, not activity Win: Higher productivity through autonomy

The Stats That Matter (And Why)

Your Next Move: Pick Your Path

Ready to stop being that boss? Choose one action:

  1. Drop one controlling behavior this week (start with those late-night messages)
  2. Learn one new leadership skill (try active listening)
  3. Ask for honest team feedback (and actually listen)

Remember: Every Teams message, every meeting, every response shapes your leadership story. Make it one worth sharing. ✌️

Your turn: Which toxic boss habit gets cut first? Your team’s future (and Sunday evenings) depend on it.

What do you think?

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Shelby Brennan
Shelby Brennan is a program management guru with expertise in wellbeing. She is currently the program manager for alift: Thriving Through Change, where she oversees development of the alift program, client relations, staff, and executive leadership directives, to ensure alift Leaders succeed throughout their journey so they can thrive through change.
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