🚩 Tactical Memo 012: Getting Others to Realize the Importance of Proactivity

Read time: 6 minutes

Welcome to Tactical Memo, my newsletter where I share frameworks, strategies, and hard-earned lessons for leaders navigating complex environments.

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The Briefing: Today’s Focus

• Why Proactivity Rarely Happens in Organizations

• The Rule: Proactivity Must Be Seen as Survival, Not Extra Credit

• A Tactical Playbook: Building a Culture of Anticipation

• What’s Happening: General Updates

• A Reader’s Question: Unlocking Proactivity in a Team Stuck in Firefighting Mode

🙇 AI-Powered Project Management Cohort 4 → Fast Action Incentive ends 9/19! Our next cohort begins on October 6th, but if you register before September 19th, you will get a fast action incentive of 15% off + an advanced copy of the Project Execution Framework to get started early.

Leaders are learning how to fuse project execution + AI, with exact playbooks to stay indispensable. Ranked #1 Project Management course on Maven Learning with a 4.8/5 student rating.

Fast Action Incentive for Cohort 4 closes September 19th, and this will be the best incentive offered for this cohort. Don’t miss it.

Why Proactivity Rarely Happens in Organizations

Most leaders complain their teams are too reactive. But look closely and you’ll see the culture itself trains people to wait for fires:

• Fire drills are celebrated. Prevention is invisible.

• People who run into problems get praised. People who quietly prevent problems get ignored.

• Leaders say “be proactive” but punish people for moving without permission.

The result: everyone is busy, but nobody is ahead.

The Rule: Proactivity Must Be Seen as Survival, Not Extra Credit

“Be proactive” sounds like a motivational slogan. The truth is that in most organizations, proactivity is treated as optional. Something you do when the inbox is clear and the projects are stable, which means it never happens.

The only way to make it stick is to treat proactivity as core survival. The system must reward anticipation the same way it currently rewards firefighting.

A Tactical Playbook: Building a Culture of Anticipation

Here’s a system you can install to shift your team from reactive to proactive within weeks.

Step 1. Redefine Success Metrics

Reactive teams measure success by output: “Did we ship it? Did we respond fast?”
Proactive teams measure success by foresight: “Did we prevent it? Did we see it coming?”

How to implement right now:

• Add a line to performance reviews: Examples of risks prevented or opportunities identified.

• Start team meetings by asking: What didn’t happen this week because of our preparation?

• Praise early flagging in front of senior leaders so it becomes visibly career-advancing.

When people see anticipation as part of how they are measured, they shift behavior immediately.

Step 2. Install the “Second-Order Thinking” Habit

At the end of every decision, force this simple question:

How to implement right now:

• Add this as the last agenda item in every project meeting.

• Rotate who has to answer it, so the whole team develops the muscle.

• Capture answers in a “second-order log” so risks and opportunities are visible across projects.

This creates a lightweight habit of looking around corners.

Step 3. Create a Weekly “Look Ahead” Ritual

Proactivity dies when people feel there’s no time for it. Protect a recurring window to scan the horizon.

How to implement right now:

• Block 15 minutes every Friday. Agenda: “What could blindside us next week?”

• Capture answers in one shared doc or whiteboard.

• Assign owners for follow-up.

This ritual normalizes anticipation instead of leaving it to chance.

Step 4. Model Proactive Communication

Leaders set the tone. If you only ever speak in reaction, your team will copy you.

How to implement right now:

• Start sending “anticipation notes.” Example: “Not urgent yet, but in 90 days our budget cycle hits. We should prep now.”

• Share risks in outcome language, not panic. Example: “If we ignore X now, it will delay Y in October.”

• Show how you take small preemptive actions (meeting early, prepping data, aligning stakeholders).

Your team will mirror how you operate.

Step 5. Protect People Who Stick Their Necks Out

Proactivity requires courage. The fastest way to kill it is to punish someone for being wrong.

How to implement right now:

• When someone raises a risk that never materializes, thank them anyway. Say: “Catching this early saved us the stress of being blindsided.”

• Publicly celebrate the act of raising the issue, not just the outcome.

• Build a “safe-to-warn” norm: no negative consequences for early flags.

This shifts the culture from silent hesitation to active anticipation.

What’s Happening – General Updates

🙇 September 19th marks the end of the Fast Action Incentive Registration for Cohort 4 of the AI-Powered Project Management cohort. This course shows leaders how to combine project execution with AI, and equips you with the exact playbooks you need to stay indispensable. It’s ranked the #1 Project Management course on Maven Learning and carries a 4.8/5 student rating.

⚡Back by popular demand! Join me for a free lightning lesson on Thursday, Sept 25th at 11:00 AM EST, where I will cover How AI Can 10x Your Project Delivery Speed. Learn how top leaders are using AI to cut timelines, reduce chaos, and deliver faster without micromanaging. You’ll walk away with a clear understanding of how project leaders are using AI right now to lead smarter, not harder.

The Briefing: Reader’s Question

Q: “I lead a team of mid-level managers who are excellent at responding to issues but terrible at thinking ahead. They only ever act when something is already on fire. I feel like I am constantly nagging them to look further down the road, but they either give me blank stares or wait for me to spell out exactly what to do. I don’t want to micromanage, but I also can’t carry the burden of anticipating everything myself. How do I get them to internalize the value of being proactive, not just when I push them?”

A: This is a real leadership choke point. If you are the only one looking around corners, you eventually burn out and your team becomes dependent on your foresight. The solution is not more reminders. It is a system that forces anticipation into the way the team operates.

Here’s what I would do:

1. Flip the Meeting Agenda. Start every meeting not with “what’s happening now” but “what’s coming that could derail us?” Make foresight the default first question.

2. Create a Proactivity Scoreboard. Put a visible tracker on the wall or in the team dashboard with two columns: fires prevented and fires fought. The goal is to get the left column consistently higher.

3. Gamify It. Assign one rotating “look-ahead officer” each week. Their job is to surface one risk and one opportunity. No exceptions. Teams quickly adapt when it is a rotating responsibility, not just a vague expectation.

4. Tie It to Relief. Show them how proactivity buys them less stress. When a fire is prevented, connect the dots: “Because we flagged that early, you avoided three nights of overtime.” Make the personal benefit obvious.

5. Use the Red Team Exercise. Once a month, run a quick “red team” drill: one group invents ways the project could fail, the other group builds preemptive moves. This builds anticipation muscles far faster than lectures.

You don’t need your team to suddenly turn into futurists. You just need them to start seeing proactivity as part of their job, not a hobby. If you install visible rituals, rotate ownership, and make prevention personally rewarding, they will shift from reacting to anticipating.

Cheat Sheet Vault

p.s… As promised, click below for my free cheat sheet and infographic vault

👉 Access the Vault Here

Until next time,
Justin

✍️ From the Desk of Justin Bateh, PhD
Real-world tactics. No fluff. Just what works.