10 Coaching Questions That Work in Every Conversation.

My good friend and sales coaching expert Keith Rosen shared this on LinkedIn this morning also referrencing his new book on this topic.I like question no. 7 a lot, as it underpins the need for a safe learning space.Have a go and enjoy his clever insights her:

By Keith Rosen

When coaching, finding the right question at the most appropriate time is a skill, mindset and an art, which often makes the coaching process difficult. Even with daily pressures and tight schedules, when supporting others, there are always baseline facts you need to know in every situation to ensure the coaching and advice you offer is relevant and valuable. These 10 questions will easily guide you and your coachee on a clear conversational path to co-creating outstanding results.

Pre-order my new book,Sales Leadership and Receive $1,250 of additional resources free when you receive the book!

Regardless of the coaching framework you use, every framework consists of well-crafted, precision-based questions to facilitate the conversation, which empowers people to self-reflect and arrive at a solution or new insight on their own.

At the core of coaching, the theory is simple: To tap into each person’s individuality by starting every conversation with the intention to understand each person’s point of view, goals, motivation, skill set, priorities, strengths, behavior, and way of thinking through the strategic use of well timed, open-ended questions.

Powerful questions encourage people to develop their own problem-solving skills and amplify their self-awareness. And if they can’t see their own gap, limiting thinking, what they need to change, or create an effective solution, only then is the timing right for the coach to share an observation that the person would benefit from which they could not see on their own.

Great leaders lead every conversation with questions, rather than answers.

Conversely, once you attempt to solve someone’s problem, even with your good intentions, you’ve adopted their problem and made it your own, relinquishing ownership rights and accountability from the person who brought this gift to you, which you kindly accepted. Consequently, their daily challenges become the gift your direct reports keep on giving.

The real gift is ensuring your direct reports keep this gift for themselves to work through their challenges and goals on their own, as it will become their most cherished gift you give – the gift of personal growth, confidence, personal accountability and self-awareness.

With the right questions, the coachee creates the solution or solves their own problem. Now, it’s theirs, so they now have ownership of the outcome, not the coach. And if the coachee created the solution, they’re more apt to act on it, rather than being told what to do.

It doesn’t matter if you have the perfect answer. People often resist what they hear but they believe what they say. That’s why the question is always more powerful than the answer.

I have found that the 10 questions below, which are part of my L.E.A.D.S. Coaching Framework, apply in practically every conversation. I’ve also provided some insight around the intention of certain questions, and why they must be asked.

These questions are sure to make your coaching more efficient, effective and intentional, now that you have a path of chronological coaching questions that will guide the conversation and best support the development of your people, while challenging them to bring out their best.

When you give people the space to share ideas, be heard and acknowledged, it strengthens people’s confidence, along with the level of trust that’s essential for great coaching and collaboration to occur.

Of course, depending upon the conversation, you may not need to leverage every single question. However, as you use them throughout your coaching efforts, you’ll start recognizing the questions that work best for you.

Keep in mind, this is just one of many ways to facilitate an effective coaching conversation. And if you don’t have a great manager or a coach in your corner, you can also leverage some of these questions to do some self-coaching! (Just don’t argue with yourself over the responses you hear. ;- )

Tip from the Coach: Don’t over-engineer your coaching! If you keep digging, you’ll keep finding more. Coach one gap at a time through to completion.

10 Coaching Questions That Work In Every Conversation

1 What is the outcome you’re looking to achieve here?

2 Can you share the specifics of what’s going on?

3 What have you tried so far? (This avoids the closed-ended interrogation question: “Did you try A, B, C, D, etc.)

4 How have you handled something like this before? (What was the outcome?)

5 Why do you think this is happening? (What’s another way to look at this/respond? What else can also be possible/true? What assumptions could you be making here? (Stimulate critical thinking. Get to the root cause or the Gap. Uncover a new possibility or coaching moment.)

6 What’s your opinion on how to handle this? (While everyone may not have a solution or be comfortable sharing an answer in fear of being wrong, EVERYONE has an opinion. And opinions are never right or wrong, which is why you will avoid the, “I don’t know,” response. Now, you can always uncover their point of view first, before you share yours.) If I wasn’t here, what would you do to achieve/resolve this? If we were to switch roles, how would you handle this?

7 What’s the first thing you need to do to (resolve/achieve this)? (What would that conversationsound like when you talk with……? TIP FROM THE COACH: Coach activity AND the message! The Big Miss for managers is stepping over the myriad of opportunities to coach your people on their message, talk tracks and communication.)

8 What resources do you need? (Who else do you think needs to be involved in this? How else can I support you around your efforts to complete this? (Danger: Don’t ask, “How can I help?” In the coachee’s ear, this translates into, “What responsibilities and tasks do you want me to do for you?”)

9 What are you willing to commit to doing/trying/changing (by when)?

10 When would you like to reconnect to ensure you have achieved the result you want?

Many managers operate under the faulty belief that you only coach when solving a problem, dealing with underperformance, or jumping in to help close a sale. Coaching transcends beyond this. That’s why every conversation is a coaching conversation.

Leading with questions rather than with answers will stretch the coach and the coachee beyond the typical, superficial, result driven, firefighting conversations, which get stressful, redundant and frustrating. Now, you have the questions to create richer, more engaging conversations with superior outcomes.


Ten years in the making, thousands of hours coaching, and one million miles traveled, I’m ecstatic, humbled and grateful to announce the upcoming release of my new book, Sales Leadership.

Read Reviews from the World’s Top Companies & Thought Leaders, such as Marshall Goldsmith, Keith Ferrazzi and world-class organizations such as LinkedIn, Square, Salesforce, Microsoft, Twitter, Google, Gartner, SAP, Oracle and more!

Pre-order Sales Leadership, and get $1,250 of additional resources free when you receive the book!


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