Using Calendly to Run Remote Coaching Sessions

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A little while back, as part of a client assignment, I ran some remote one-on-one DevOps coaching sessions for a group of about 30 people. This was newer territory for me and I didn’t have a go-to “toolbox” for maintaining these sessions. However, I had a great experience with Calendly 1

I figured I would jot down how I used the tool in case anyone finds themselves in a similar situation.

Create a Form for Feedback

Feedback is essential in any coaching engagement. I prefer to ensure I’m receiving feedback in person, but sometimes folks aren’t 100% comfortable and an anonymous feedback form can be helpful.

I recommend creating a form wherever is comfortable for you (Google Drive, Office Forms, etc.) where you can aggregate the responses. I used Office Forms as it was my employer’s preference. Make sure that you can generate a link to the form that can be visited anonymously.

I kept my feedback form simple so that folks would use it, asking the following:

  • On a scale of 1-5, this was a good use of my time.
  • What did you like best about the session?
  • What could I do to improve or better prepare for future sessions?
  • Anything else I should know?
  • Would you like me to follow up on this feedback? If so, contact info.

Sync Your Calendars

At the time, I had both my employer’s calendar and my client’s calendar that needed to be taken into account for those who wanted to schedule meetings. I synced both calendars with Calendly.

Set up a Slot for Others to Schedule Coaching Sessions

I set up meetings slots for various time lengths (15, 30, 45, 60, 90 minutes) so that coachees could choose the session style to best suit their needs.

For each meeting type, I set it up as follows:

  • I set a time range of when people could book the meeting (through the end of my coaching assignment, as many meetings as they’d like.)
  • I set the meeting increments in 15-minute chunks to ensure that someone didn’t schedule meetings at 2:03 pm.
  • I set that there should be a break between meetings of 15 minutes. This allowed me time for notes, bathroom breaks, etc. which is important if you’re going to be doing video meetings all day.
  • On the invitation form, I ask for their name and e-mail – to ensure I know who I’ll be talking to.
  • I set an e-mail to follow-up 1 hour after the meeting – this is where the feedback form comes into play. I used the template below:

Hi {{invitee_first_name}},

Thank you for attending {{event_name}} at {{event_time}} on {{event_date}}.

I’d love your feedback! Please see [TODO: the link] for a brief, anonymous feedback survey. You can also respond to this e-mail and provide me your feedback directly.

Also, don’t forget to schedule your next sessions at You can schedule several sessions in advance before dates fill up. Be sure to use up our allotted time by [Date]!



PS sorry that this is automated; I normally prefer to do these in a more personal way but the volume of meetings prohibits that at this time.

I could also use the Calendly invite prompts to ask the coachee to provide a number of topics, but we did that within the space of the meeting.

What Were the Benefits?

  • Coachees scheduled 70+ coaching sessions using the tool, and we rarely had an issue or conflict.
  • My calendars, and thus availability, were always up to date. I could add calendar events or meetings and know I didn’t have to update coaching sessions.
  • I got 20+ pieces of anonymous feedback from the automated link that was sent out, without needing to do additional work between sessions, because the form was automated.
  • I generally had nice gaps between coaching sessions where I could take a breath and gather notes before the next call.

What are Your Favorite Tools / Processes?

Are you doing any one on one coaching? What are your favorite setups these days?

Happy coaching!

  1. No affiliate link, promotions or kickbacks; just a happy customer. 

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