My Weekly Leadership Cadence
Use my simple, repeatable weekly calendar cadence to coach the team, build culture, and drive deals forward
What does your weekly cadence look like?
Over the years, I’ve tested a lot of rhythms for sales leadership and often make it a point to learn what and how others run their week - and added the things that seem to resonate.
What follows is the cadence I seem to come back to. It’s simple, repeatable, and helps me stay focused on the three things that matter most: coaching the team, building culture, and driving deals forward.
Take a look and let me know in the comments what you like, or what you’d add…
THANKS for reading!!
-Grant
And lastly - as always, if you find this newsletter valuable- subscribe or share it with someone who might as well 👊.
My Weekly Leadership Calendar Cadence
Monday: Team Meeting (60 min)
We kick off the week with a structured team meeting:
KPIs: Review topline numbers: closed business, pipeline coverage, and pacing to quota
WFTW: Celebrate WFTW (wins from the week)
Announcement: Share key announcements from marketing, product, or ops
Success & Stumbles: Review 1 success and 1 stumble from real calls (Gong/other)
Open Mic: Turn to the team for insights, field feedback, and shared learning
Monday–Wednesday: 1:1s (45 min)
We alternate 1:1 formats each week:
Week A: Zoom-based pipeline reviews, top deals, areas for coaching
Week B: “Walk and Talks” via phone—focused on personal development, team culture, and life outside the forecast (check out my recent post on the Walk & Talk HERE)
Monday–Friday: Deal Reviews (30 min per deal)
Each week, I select 1–2 deals to dig into more deeply. Some are rep-only; others include SEs, CS, or cross-functional leaders. These sessions help us unblock stuck deals, map the strategy, and build strong mutual plans of action.
Thursday: Forecast + Training Block (60 min)
In one combined session, we:
Run a scripted forecast review (total pipe, commit, best case, most likely)
Follow it with 30 minutes of tactical training: discovery, objection handling, competitive strategy, or product updates, all based on where the team needs sharpening
If you're a revenue leader trying to create structure without bureaucracy - or a founder still figuring out what sales leadership should feel like - this cadence is a good place to start.
Want to see the full calendar cadence in detail?
I’ve published the full Stretch VP Leadership Calendar Cadence in a public Notion doc- complete with structure, deal review frameworks, and coaching prompts.
Reply with “Stretch Calendar Cadence” and I’ll send you the link.
🧠 Mindset
“Own your inner game to win the outer game”
Thanks for reading!
My hope is if you find this valuable, consider sharing it with friends (or signing up if you haven’t already).
— Grant 👋
About stretch vp: confessions, learnings, and insights from sales leaders in SaaS
Compiled and aggregated from a network of sales leaders in SaaS, Stretch VP showcases learnings, insights, and experiences as well as best practices to overcome common hurdles, obstacles, and setbacks in your quest for excellence as a sales leader in SaaS.
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