If you’re running coaching sessions—whether for sales teams, onboarding, or just keeping your people sharp—you know that getting everyone to show up, on time, every time, is harder than herding caffeinated cats. This guide is for managers, coaches, and admins who want less “Wait, when is this?” and more actual coaching. We’ll walk through how to set up recurring coaching sessions in Wonderway, keep them running smoothly, and avoid the usual time-sucking pitfalls.
Let’s get into it.
Step 1: Decide What “Recurring” Actually Means for You
Before you even touch Wonderway, get clear on what you need:
- How often do you want sessions? Weekly, biweekly, monthly? Don’t overcomplicate it—default to the lowest frequency that keeps things moving.
- Who needs to be there? Is this a one-on-one, small group, or everyone-and-their-cousin type deal?
- Do you need the same agenda each time, or will it change? If you’re always reinventing the wheel, recurring won’t save you much time.
Pro tip: Most teams overschedule. Start with less frequent sessions, then increase if people are actually getting value.
Step 2: Set Up Your Coaching Program in Wonderway
Assuming you’ve already got a Wonderway account and access to coaching features, here’s your play-by-play:
- Go to the “Coaching” module. You’ll usually find this in the main menu. If you don’t see it, you might need different permissions—check with your admin.
- Create a new coaching program. Hit “Create,” “Add Program,” or whatever your version calls it. Name your program something obvious, like “Weekly Sales Coaching.”
- Choose your session format:
- 1:1 Coaching: For manager-to-rep sessions.
- Group Coaching: For team or pod sessions.
- Don’t get fancy unless you have a real reason. The simpler, the better.
- Define your participants. Add people by name, team, or role. Double-check your list—removing or adding people later is possible, but messy if you do it mid-series.
- Set the recurrence.
- Look for the “Repeat” or “Recurrence” option.
- Set your frequency (weekly, biweekly, etc.), day, and time.
- Decide on start and (optionally) end dates.
- Set your agenda or coaching template.
- Wonderway lets you set a default agenda or checklist for each session.
- If your agenda changes a lot, keep it flexible or use a simple template. Don’t try to automate what needs a human touch.
Watch out: If your org uses multiple time zones, double-check what time zone Wonderway thinks you’re in. Nothing derails a coaching culture faster than calendar confusion.
Step 3: Send Invites and Get Buy-In
Here’s where most recurring meetings die: people ignore the invites, and before you know it, half your team “didn’t see it on their calendar.”
- Send invites directly through Wonderway. The platform should handle calendar integration for Google or Outlook, but always do a test run first.
- Add a note explaining why these sessions exist. If it feels like another pointless meeting, expect drop-off.
- Get explicit RSVP or commitment. A quick “Reply if you can make it” in your note goes a long way.
What to ignore: Sending a massive email blast. No one reads those. Keep it personal and direct.
Step 4: Prepare for Your First Session (and All Future Ones)
Recurring doesn’t mean “set it and forget it.” Here’s how to actually get value:
- Review the agenda/template before each session. Don’t just regurgitate last week’s talking points.
- Leave room for feedback. Wonderway usually lets you collect feedback after each session—use it to improve, not just to tick a box.
- Set expectations: Remind people (in the first session, and periodically) what these sessions are for and how to get the most out of them.
Pro tip: Block off 10 minutes after each session to jot down what worked and what didn’t. You’ll thank yourself later.
Step 5: Make Recurring Adjustments (Because Life Happens)
No recurring schedule survives contact with reality. People get busy, priorities shift, and sometimes the group just doesn’t gel.
- Reschedule as needed. Wonderway lets you adjust the series or individual sessions. When in doubt, favor consistency over squeezing everyone in.
- Add/remove participants. Do this sparingly. Too much churn and nobody knows what’s going on.
- Cancel sessions when there’s no real need. Don’t just meet to meet—if there’s nothing urgent or valuable, skip it. People will appreciate your respect for their time.
What doesn’t work: Trying to force everyone to attend every session, especially in busy seasons. Flexibility beats rigidity every time.
Step 6: Track Progress and Outcomes (Without Drowning in Admin Work)
Recurring sessions are only useful if you (and your team) are actually improving.
- Use Wonderway’s built-in tracking. You can usually see attendance, participation, and any goals or outcomes from each session.
- Set clear, measurable goals. “Improve sales calls” is vague. “Increase demo-to-close rate by 10%” is actionable.
- Review progress monthly or quarterly. Look for trends—are people getting better, or just going through the motions?
- Don’t overdo the paperwork. Use Wonderway’s notes and checklists, but don’t create more admin work than value.
Pro tip: If you’re spending more time updating the platform than coaching, something’s off. Simplify.
Common Pitfalls (And How to Dodge Them)
Let’s be honest: most recurring meetings fail for the same reasons. Here’s what to watch for:
- People stop showing up. Usually means the sessions aren’t useful. Ask for feedback, adjust, or cut back.
- Sessions feel repetitive or aimless. Refresh your agenda, bring in new topics, or switch up the format.
- Coaches burn out on prep. Use templates, but don’t script everything—leave room for real conversation.
- Calendar chaos. Always double-check time zones and calendar integrations. Just because it’s on your calendar doesn’t mean it’s on theirs.
Wrapping Up: Keep It Simple, Iterate Often
Recurring coaching in Wonderway can be a game-changer, but only if you keep it practical. Don’t get bogged down in automation or fancy features—focus on what actually helps your team improve. Start simple, gather feedback, and tweak as you go. When in doubt, less is more.
You don’t need another meeting on your calendar—you need coaching sessions that actually move the needle. Stick with it, keep it real, and you’ll get there.