[OTL Newsletter 🎯] You're not bad at your job. You're just stuck in firefighter mode.

Observation 🧐

Earlier in my leadership career, I would finish the work day exhausted.

👎Back-to-back calls.

👎Random Slack pings.

👎A rep asking for help on a deal they should’ve prepped for three days ago.

👎Another late forecast update.

👎And the QBR deck? Still blank.

I was working hard, there was no doubt about that. .

But I felt stuck on the hamster wheel and I wasn’t making progress.

Over time, I came to the realization:

My job as a leader wasn’t to solve the fires.

My job was to enable and empower the team to extinguish the fires without me.

That’s where systems come in. 

A system is any repeatable way of doing things that creates consistency, saves time, and reduces stress.

It doesn’t need to be fancy.

It just needs to work without you being the bottleneck.

They protect your time.

They build trust and independence in your team.

They create the space you need to actually lead.

What does this look like in practice?

🔥 Common Fire: Reps updating the pipeline late

You’re constantly chasing reps to update their deals before forecast meetings.

You end up doing last-minute cleanup every Friday or scrambling Monday morning.

Your forecast slides are always almost right… but not quite.

And you’re spending more time updating Salesforce than your reps are.

🛠️ System Solution: Pipeline Hygiene Workflow

Let’s build a simple, 3-step system to solve this:

1. Weekly pipeline update deadline

Set a non-negotiable time for reps to update all deals.

→ Example: Every Friday by 3PM.

Make it clear what “updated” means:

• Next steps are accurate
• Close dates are realistic
• Deal stages match the customer’s intent
• Notes are logged for key opportunities >$amount

Put this deadline in calendars and reinforce it weekly.

2. Automated reminder

Use Slack, email, or your CRM to automate the nudge.

→ Example: A Slack reminder every Friday at 1PM (T-Minus 2 hours!)

Include a checklist:

Pipeline Hygiene Reminder

✅ Update all notes 

✅ Remove dead deals

✅ Review next steps + close dates

Let your system do the reminding

3. Visibility + accountability

Build a dashboard or report that shows:

• Who updated on time
• Which deals are missing key fields
• Which reps need follow-up

Celebrate consistency. Coach where needed.

Consider gamifying it if you have a competitive team.

📈 Why this works:

• You’re no longer chasing reps manually
• Forecast meetings are faster and more productive
• You gain time back for coaching
• Reps take more ownership of their deals
• You start building a culture of self-management

And most importantly—this frees up your mental load.

You're not worried about the pipeline every Sunday night.

You're not cleaning up messes every Monday morning.

You’re leading, not reacting.

Repeat this process for other recurring fires:

• 1:1s that feel scattered → Create a coaching agenda template
• Deal strategy requests → Build a Deal Review framework
• Hiring churn → Standardize your interview scorecard
• Onboarding inconsistencies → Build a 30-60-90 playbook

Start small. Stay consistent.

You don’t need to fix everything overnight.

Pick one fire.

Build one system.

Test it. Tweak it.

Then move to the next.

Thought Starter  🤔

Read more on LinkedIn

Love 🥰

I can’t possibly have a newsletter about systems without mentioning the best book on the topic - Atomic Habits by James Clear. 

If you want to go to the gym in the morning, pick out your exercise clothes the night before. Set yourself up for success. 

“Your goal is your desired outcome. Your system is the collection of daily habits that will get you there”

Magic.