Sales management training and coaching programs.
One of the biggest frustrations I hear from managers sounds like this:
“I sit down for a coaching session with one of my reps and we just… wander.”
“We talk about a few deals.”
“We update pipeline.”
“45 minutes later, and we aren’t really sure what we accomplished. And then, my team doesn’t feel coaching is valuable.”
Without structure, the conversation meanders. Since most managers act as Chief Problem Solvers, you end up searching for something to fix. The employee waits for direction. Consequently, you both default to status updates and pipeline reviews instead of growth.
Now, the conversation becomes more about the manager’s objectives than the coachee’s.
Why Your Opening Coaching Questions Fail
A powerful coaching conversation does not start with you and the coachee scrambling to find a topic. And it definitely doesn’t start with the manager bringing their agenda.
It starts with clarity. And that clarity comes from the person setting the agenda before they show up to the coaching session that the manager can now focus on and honor, rather than the manager’s agenda.
The Prep Form: 3 Questions to Answer Before Every Coaching Session
Here are three questions every employee needs to respond to, or better yet, have them send their responses to you prior to the coaching session that structure the session and provide purpose, value, and focus.
- What are your wins since our last session?
- What are your challenges?
- What are your expectations of our session that would deliver the value you expect.
If there’s no agenda developed by the coachee, then it quickly shifts the focus to the manager’s agenda.
Management’s agenda never has a place in a coaching conversation. If you have something you want to discuss or there was something you’ve observed and need to bring to their attention, don’t call it a “coaching session.” That’s a separate meeting.
Otherwise, coaching gets diluted, and your people won’t know what to expect when they walk into a coaching session, which creates fear, distrust and coaching failure.
When your people choose the focus during coaching, they own the outcome.
Creating Winning Coaching Sessions
If you’re always in search of new and innovative ways to open up a coaching conversation in a way that would move it forward and get the person to comfortably open up and focus on their agenda, here are 14 unique questions I use to open up a new coaching session. Ask them with intention. Then listen.
- What are your expectations of our coaching session today?
- What do you need most from me today?
- How would you like me to coach you today?
- Is there anything you would like me to do more of or less of during our meeting?
- So, let’s start by hearing what is wonderful in your world.
- What do you want to leave with today?
- What do you want to learn today?
- What have you learned this week?
- What have you done this week to become more of who you want to be? (Or to achieve your goals.)
- How do you want to feel at the end of our coaching session?
- If there was one thing that would be worthwhile for you to achieve today, what would it be?
- What is one thing we could work on together that would be incredibly valuable for you?
- Before we jump in to what you want to discuss today, how about we begin by reviewing the fieldwork/activities we identified during our last meeting that you committed to completing by our meeting today.
- What’s the single focus for our coaching that will help you reach multiple goals?
Most managers begin coaching sessions in a reactionary way, focused solely on results. Strong coaches open sessions through open ended-powerful questions that honors the coachee’s agenda, priorities and goals, not yours.
When you start a coaching conversation with questions, it creates intention. Then, the conversation stops drifting and starts creating new opportunities that accelerate better results.
When the coachee sets the agenda, defines the outcome, and identifies what success looks like before the conversation even begins, you shift ownership.
You move from reporting to reflecting. From updating to improving. From managing activity to developing capability. Coaching is not a meeting you attend. It is a collaborative, developmental process you co-create together.
Let them choose the focus. Let them define the win. Your role is to kick-start the conversation with a thought-provoking, innovative question that will guide them there.
That’s how mundane conversations turn into meaningful ones.
The post How to Kick-Start a Coaching Session: 14 Questions That Turn Mundane Management Conversations into Meaningful Coaching Sessions first appeared on Keith Rosen.

