Effective Questions

December 4th, 2023 | Coaching Managing
Effective Questions

“Excerpted” With Permission from the 11th Chapter of   “Coaching Essentials for Managers: The Tools You Need to Ignite Greatness in Each Employee” by Sara Canaday

Great questions are the key to successful coaching. This chapter includes a range of themes you can incorporate into your own coaching conversations and modify as needed. You’ll find a variety of approaches for both Performance and Developmental Coaching. Think about which questions feel most natural for you, based on your personal communication style, and start to weave them into your next coaching session.


A simple way to think about the questions you use in coaching conversations is to link them directly to the five-step framework in Chapter 2. This will keep you on track to cover all of the critical components needed for an efficient, effective discussion. With that in mind, let’s walk through the framework steps so you can determine which questions work best at different points in a coaching session.

Step 1: Assess the Situation

In Step 1, you’ll work to help identify specific problems that need attention, pinpoint performance challenges, uncover career aspirations, or overcome hurdles to advancement.

The following questions can be used in your coaching sessions to achieve those goals in assessing the situation:

• What can you tell me about ______________________________?

• What do you think about ________________________________?

• What do you make of ____________________________________?

• How do you feel about __________________________________?

• What concerns you the most about _______________________?

•  What impact is this having on you now?

•  What impact is this having on the team/company/customers?

• What seems to be your main obstacle?

• What do you mean by ___________________________________?

•   What else can you tell me about __________________________?

• What is holding you back from ___________________________?

•  What would make an ideal work situation for you?

• What special interests do you have?

• What activities inspire you the most?

• What is your ideal outcome?

•  How do you want _____________________________ to turn out?

Step 2: Generate Ideas

In Step 2, you’ll guide coachees to analyze potential solutions for the challenges they have identified.

The following questions may help as you work with them to generate ideas:

•  What choices/actions would be most likely to help you meet your goal?

•  Is there an obvious solution, or does this require something more creative?

• What solutions have you tried?

• What has worked for you already?

• How could you do more of that?

• What hasn’t worked so far?

• What did you learn from trying ___________________________?

• What do you think is stopping you from trying ______________?

• What could you change about your approach to get a better result?

• What could you have done differently?

• How might you handle it next time?

• What skills/experiences do you think might make you more effective/promotable?

• How could you demonstrate your leadership ability, even if you’re not technically a leader?

•  Are there ways to gain some of the experiences you need outside of your current role (industry organization involvement, community service, committee leadership)?

Step 3: Develop an Action Plan

In Step 3, you’ll prompt coachees to strategically filter through the ideas generated, determine the best solution, gain clarity on the specific steps needed to implement that solution, and prepare for any hurdles along the way. By guiding them to link their action items to results, you strengthen their decision-making skills and improve their confidence.

The following questions can support your goals in these conversations:

• What solution do you propose? And why?

• What are the downsides, if any?

•  What obstacles could get in the way of success?

• How can you overcome those obstacles?

•  If you do this, how will it affect ___________________________?

•  What is the cost of not doing this?

• What else do you need to consider?

•  What is your overall plan to implement this solution?

• What are your next steps?

•  How will you know when you have succeeded?

Step 4: Provide Support

In Step 4, you’ll keep the accountability for outcomes fully on the people you are coaching while offering to use your knowledge, network, and clout to expedite their success.

The following questions can provide the structure for those pivotal discussions:

•  How can I support you in making this happen?

•  What do you need to begin the process?

•  What else might be helpful to know as you pursue this?

•  Who else can support you as you take on this project?

•  Are there any connections I can facilitate to speed up the process?

•  Are there any obstacles you anticipate that I might be able to remove?

•  What would make you more comfortable with taking this on?

•  Would you like me to look at the report/presentation before you submit it?

Step 5: Follow Up

In Step 5, you’ll work to stay connected and assess the progress of the people you’re coaching, evaluate their strategic thinking, determine whether they are implementing the action plan you’ve developed together, and identify any bumps in the road.

These follow-up questions may be helpful in making your analysis:

• How are things going with your project/experiment?

•  What did you take away from the book/podcast I recommended?

•  What was the best thing you learned in the training class?

• How did the informational interview go?

•  How do you feel about the progress you are making so far toward your goal?

•  What shifts have you seen in how you are handling __________?

•  What reactions have you noticed from your colleagues/clients since you changed _______________________________________?

• Have any of the original variables shifted?

•  Have you uncovered anything that might make you rethink your goal or strategy?

It’s impossible to overstate the value of great questions in a coaching conversation. On the surface, those questions gather important information. But the real genius behind them is how they can prompt your coachees to think about situations in a whole new way: shifting into strategic mode, stretching their creative muscles, looking for the not-so-obvious options, and solving problems on their own. If you can learn to ask brilliant questions at the right times, you can become the coach within your organization that employees are clamoring to work with.


•  Great questions are the key to successful coaching.

•  When you align your questions with each step in your coaching framework, you can stay on track to cover all of the critical components needed for an efficient, effective discussion.

•  By guiding coachees to link their action items to results, you help them strengthen their decision-making skills and improve their confidence.

Note from Bob:  Click HERE to purchase your “Coaching Essentials for Managers: The Tools You Need to Ignite Greatness in Each Employee”  book today!


Sara Canaday


Sara Canaday  is a recognized expert and author in leadership and career management who helps arm professionals with the strategies and practices they need to succeed in today’s complex and competitive business climate.  She partners with Fortune 500 companies who are committed to helping their employees strengthen their leadership skills, improve business relationships, and enhance their performance.  You can connect with Sara @SaraCanaday.com


“8 Questions for Helping Others Develop a Vision Statement”

Guest Post by Dr. K. Shelette Stewart              Then the Lord answered me and said: “Write...

For Valentines how about giving each other the Gift of a Great Conversation?  

The best remedy for marriage conflict is marriage...

What Would Happen If…?

Note from Bob:  What would happen if you could double or triple or 10X your response rates from you...

7 Reasons Why You Should Ask Your Team Questions

Excerpted with Permission from the 18th Chapter of  “Blue-Collar Leadership & Supervision” by Mack...

Most Sales Advice Is Wrong

Guest Post by Josh Braun You are told: 1. You need unbridled enthusiasm. Unbridled enthusiasm is akin to a...

Leveling Up – Book Review

I just finished reading “Leveling Up – 12 Questions to Elevate Your Personal and Professional...

Why Great Leaders Don’t Always Answer Questions

Guest Post by Mark Fritz Inexperienced leaders try to answer all the questions – they view it as an...

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.