What Kind of Coach Am I?

What is your default setting as a coach? Do you lean on giving direct advice to change the teacher’s immediate behavior? Do you tend to ask more reflective questions to help the teacher look at the bigger picture?


As coaches we develop our own unique style in the way we ask questions, how we approach conversations, and how we gently push the people we coach. Whetstone wants to help you think about your coaching style and how you can adapt your style to the needs of your teachers. For this month’s post we are going to dive into 2 different kinds of coaching styles to give you a frame of reference for your coaching so you can begin thinking about where your strengths and growth areas are.

Here’s a short story about an experience I had as a coach that helped me identify where I was as a coach:

A few years ago, an intervention coordinator (who I’ll refer to as Andy) and I were coaching a math team. Both teachers were in their first year in the classroom and Andy and I were trying to focus on small changes they could implement to improve class culture. We took a largely facilitative approach through asking a lot of overarching questions about what they want their students to get out of the class, and helped them reach a few productive changes they could implement for the next day’s classes. Week after week Andy and I would meet and discuss the lackluster progress in the classroom and discuss what we should be doing as their coaches.

Not long after, our school brought on another instructional coach. After her first session with the math teachers we had been coaching, the teachers were excited for their classes the next day and had a great game plan. After just a few weeks of sessions with her, the teachers had achieved more progress than they had all year with Andy and me. After much reflection, Andy and I realized we were not meeting the teachers where they were. We were taking a facilitative, questioning approach, when they were two first year teachers in need of clear, direct coaching. Once the instructional coach came in and met their needs, they were relieved, motivated, and immediately started growing.

Now back to you! Let’s start the conversation about our coaching identities with 2 distinct styles as defined by Elena Aguilar:


”Focuses on changing a coachee’s behavior. The coach shows up as an expert in a content or strategy and shares their expertise. They might provide resources, make suggestions, model lessons, and teach someone how to do something”


“Supports coachees to learn new ways of thinking and being through reflection, analysis, observation, and experimentation; this awareness influences their behaviors. The coach does not share expert knowledge, they work to build on the coachee’s existing skills, knowledge, and beliefs, and help the coachee to construct new skills.”


These two styles are not mutually exclusive, and as coaches we will sometimes be directive and facilitative in the same conversation. The key is to give yourself the mental space and flexibility to do both, without having a coaching identity crisis. Knowing when to be directive and when to be facilitative is part of what makes coaching such challenging work. We must not only consider our own strengths and style as a coach, but where the teacher is and how to approach them in a way that will yield the most positive results.

Until next time, we hope you think about what kind of coach you are. For our next post we will dive into more coaching identities and feature some coaches from around the country. We want to know who you are as a coach, what kind of teachers you tend to breakthrough with, and which ones you have a tougher time with. If you’d like to contribute, please email spencer@whetstoneeducation.org.

Stay sharp!

The Whetstone Team

Coaching Questions 201: Advice from School Leaders

Last month we began exploring how to improve on different aspects of the questioning process in a coaching conversation. The Whetstone team wants to harness the knowledge of some of our brilliant partners in this work to give their first hand experience and advice when it comes to asking the right questions. The school leaders we polled for this month have great experience as coaches and are probably in a coaching conversation as you are reading this. We polled them on 4 simple questions so they can relay their insights and experiences to you to improve your coaching. Here’s our team of experts for today’s post:



Joshua Cella

Assistant Principal

Phillis Wheatley Community School

New Orleans, LA






Michelle Anderson

Director of Literacy

New Heights Academy

New York, NY






Brionne Stewart

Assistant School


Young Audiences Charter

New Orleans, LA





Michael Richard

Former Principal

Current Director of Sales at Whetstone

New Orleans, LA


What questions do you ask to facilitate self reflection for a teacher?

Joshua: For our experienced teachers whose classes have more nuanced next steps, I like to ask them what they want to work on in advance, so I can then reflect with them in our check-in after I observe their focus area. For teachers with more clear next steps, often management-centered, I find having them self-record and send me their areas of growth to be an effective method to start teaching self-reflection.

Michelle: Was your objective met? How do you know? What were students asked to do? Is this what you expected?

Brionne: What went really well in the lesson or what do you feel really good about and what would be your "even better ifs"? I then normally elaborate and build upon their responses or ask a targeted reflective question based on the target of the coaching session.  E.g. How does communication of the learning target impact student achievement?  What is your educational philosophy and how do you think they impact your everyday instructional strategies?  What instructional strategies most align with your educational philosophy and why?  How do you know that all learners are mastering the learning target of the day within the lesson?  

Michael: “How did it go?” And “How do you know?”  The second is so important because it should all be grounded in data.

What have you learned as a coach about how/how not to ask questions?

Joshua: I have learned to always strive to find a balance between being directive (when necessary) and inquisitive whenever possible--this balance is best for relationships, for students, and for teachers.

Michelle: Questions should be open ended and not sound leading by using words like "should" or phrases like "How come…?"

Brionne: I have learned that you should start with people's beliefs, build relationships and then guide them through reflection.  It is important to get to know your staff as an educator in order to effectively coach positive change.

What is a question you received as a teacher or leader that left an impact on you?

Joshua: One that forced me to reflect on positive teacher moves: What did students do well today? What was the teacher move that unlocked that?

Michelle: Does this product represent my best work?

Any other insights on questions?

Joshua: Don't forget to ask the person how they're feeling.

Brionne: Questions are tricky.  You have to be genuinely interested and invested in their success as a teacher and sometimes questions make teachers feel the opposite.  Coaches must let teachers take the reigns of their learning or TEACH the teachers how to do so with reflection within a coaching session.  Active listening is just as important as questioning in sessions.  

Michael: Very general questions promoting self inquiry also provide insight to the coach by highlighting what the teacher is focused on.  Coaches should follow up with questioning that guides inquiry elsewhere as needed.


The Whetstone team sincerely thanks Joshua, Michelle, Brionne, and Michael for the dedication to their students and staff and for sharing their wisdom with us. We sincerely hope you’ve picked up a few extra questions for your coaching toolbelt so you can try something new in your next coaching conversation. If you have any coaching areas you’d like for us to explore later down the road, please email spencer@whetstoneeducation.org.

Thanks for tuning in!

The Whetstone Team

Coaching Questions 101

You just finished teaching your toughest class of the day where the partner work you planned ended with pairs of students talking and goofing off instead of choosing the topic for their project. You sit down with your coach to talk about the tumultuous class and after a few minutes of catching up the coach asks “Should you re-think your seating arrangement in class since there was so much talking today?”

This is frustrating. When someone asks you a question where they are clearly looking for a specific answer, it feels more demeaning than supportive. If you’re a coach in any capacity you have more than likely fallen prey to this misstep. Learning what kinds of questions to ask and how to ask them is an integral part of any coach’s development and can drastically improve our coaching. So this month’s blog post is about asking THE RIGHT questions to drive development in your coaching conversations. Just as you want your teachers to grow and improve in the classroom, the Whetstone team wants to be a resource for you as you to develop as a coach.  


Why do we ask questions in a coaching conversation? Self-reflection is the spark for quality teacher development, and it takes thought provoking questions to begin the process of reflection. Expert coach, Elena Aguilar (The Art of Coaching), says that “coach-talk” should account for one third of the conversation at the very most. If the goal of a coaching meeting is that the teacher owns the thinking, we have to limit our talking as coaches just as we would expect a teacher to do in order to get their students to own the thinking of a lesson. If we commit to only talking for a third of the meeting, then we need to be able to ask genuine, thought-provoking questions that drive the teacher toward quality self-reflection. The paths and resources below were designed with the support and expertise of Leadership Coach, Kelsey McLachlan, from Leading Educators for you to pick up some extra tools and expand your coaching skillset.

How to Prepare

We have to look deeply at what our teachers are experiencing if we want to come prepared with quality questions for a coaching session. For questions to drive introspection and development, we have to consider what purpose the question serves, how it will drive development, and how we deliver that question -- our tone and our word choice. For those of you who love planning templates and want to improve your planning process, The Road to Learning’s template on Learning Focused Conversations is an excellent tool that will ensure productive planning.

Shift to Questioning

It can be hard to stay quiet in a coaching conversation. Sometimes we think of the perfect anecdote from when we were teaching or we want to jump in with advice or talk about an awesome blog post we just read! Learning to place the emphasis on the teacher is challenging and Elena Aguilar gives the how and why this shift is necessary in her article, Learning to Improve Your Coaching with One Move: Stop Talking.


Questioning Missteps

Questions are not suggestions. When we ask a question like, “Should you re-think your seating arrangement?”, we are really giving advice and dressing it up like a question. This can sometimes come off as condescending and hinder the coaching conversation. If we want to give a suggestion we should be forward with it. Or in this instance if we want to have a discussion around class culture and seating arrangements we should start with more general questions about class culture. For a deeper look into the mistakes that we can make here, we recommend this brief article from Tony Stoltzfus (author of Coaching Questions). He dives into everything from the dangers of interrupting to the dangers of asking ‘why’ in questions.

We sincerely hope these resources help you to find the right questions for your teachers. Tune in for next month’s post to hear from school leaders and other experts on what questions they find impactful both as coaches and coachees.


The Whetstone Team (pictured below dining at Middendorf’s)

Image uploaded from iOS (1).jpg

The Foundation for Coaching

While Whetstone has your back when it comes to organizing your coaching notes and providing analytics to help you run data-driven professional development, we can’t make you form a strong relationship with someone else. (We leave that for Match.com.)

Seriously though, you are the one responsible for forming a powerful bond between yourself and the teachers you coach. That’s what good coaching is all about. As coaches we must be able to develop trust with coachees so that we can help them grow as educators and transform the lives of our students. So we’re kicking off our 17-18 school year blog series with a post on how to build and maintain trust in a coaching relationship.

As a company built around the belief that coaching can transform schools, we hold trust in high regard--it’s a necessary foundation for any coaching relationship. It requires constant care and support so we want to help you with both building trust during your initial meeting with a coachee and maintaining and improving that trust throughout the year. Here are some helpful tips and strategies from some of our brilliant partners in the New Orleans education community to help you have a successful school year.

Build trust at first meeting

This sets the foundation and expectations for the relationship.

1. Let the teacher guide the conversation. Vice Principal of Academics at Joseph S. Clark High School, Lindsey Cross:

“Ask the teacher about their strengths, goals and experiences - particularly if it's the first time you two have worked together. It's important that the teacher feel they have a voice and a say in steering the direction of your conversations and their work toward their own professional goals.”

Joseph S. Clark High School in New Orleans’ Treme Neighborhood

Joseph S. Clark High School in New Orleans’ Treme Neighborhood

2. Ask them how they learn best. Instructional Coach for Teach For America, Alicia Dagostino says:

“I begin by asking how they learn best and how they like to receive feedback.”

3. Set expectations together. Chief Academic Officer of Arise Schools in New Orleans, Cari Killian says:

“During the meeting I share what the debrief structure for our observation and feedback meetings will entail...When setting expectations it’s not just about the expectations for the teacher or leader I am working with, it’s also about expectations for me as the coach.”

Maintain and improve trust throughout the year

Our teachers will face stress, failure, and fatigue which can make the coaching relationship more challenging so make sure your relationship is equipped to handle it.

1. Ask for feedback. Cari Killian says:

“In one on one debriefs I ask questions like, “What can I do to support you better?” or “How could I have better supported you in that situation?” I have learned a lot from just asking these questions on ways I could improve my coaching.”

Arise Academy in the 9th Ward of New Orleans

Arise Academy in the 9th Ward of New Orleans

2. Practice with your teacher.

“Practicing techniques or strategies shows trust, it shows investment in the teacher and that we are in this together,” says Allie Rust, former math teacher and current Customer Success Manager at Whetstone.

3. Embrace the tough conversations. Leading Educators’ Leadership Coach, Kelsey Mclachlan says:

“If I don't have the tough conversations with the people I coach, I actually lose trust instead of gaining it. I think if you don't challenge thinking or give adjusting feedback that might be hard, people wonder what else you aren't being honest about.”

4. Follow through. Both Lindsey and Cari stressed the importance of making sure your actions match your words:

Lindsey Cross: “Your visibility in their classroom and in their sphere of work is vital to establishing and maintaining trust. And always give them a glow and a grow... Don't leave the classroom until you have both key ingredients.”

Cari Killian: “My goal is to meet the expectations I set with the teacher/leader in the first meeting and follow through on all the next steps I say I will do as time goes on. If I say I will be observing him/her twice a week, then I work to keep that commitment...I also think that it’s important that when a next step does fall through the cracks and goes unfulfilled, I apologize.”

Start using these strategies to build transformational coaching relationships this year. For more detailed coaching tips, we highly recommend Elena Aguilar’s The Art of Coaching as a resource. Thank you for tuning in to our first blog post of the year.

Have a happy and successful school year.


The Whetstone Team

Whetstone Selected to DA Magazine's "Readers' Choice Top Products for 2016"

Whetstone Education has been recognized again for making a positive difference in education by K12 leaders who named it to District Administration magazine’s “Readers’ Choice Top Products for 2016.” The winners were compiled from 2,100-plus nominations from the magazine’s readers over the past year. District Administration’s Readers’ Choice Top Products awards program informs superintendents and other senior school district leaders about products their colleagues around the country are using to help their districts excel in a variety of areas.

“It was inspiring to learn about the products being used in today’s schools and classrooms that are helping districts succeed,” says JD Solomon, District Administration’s editorial director. “All of our 2016 honorees should be very proud of this achievement.”

“Whetstone's users -- teachers, principals, district leaders -- have played an integral role in shaping our technology,” says Libby Fischer, CEO of Whetstone Education “Being nominated for this award again underscores the success of these thought partnerships and the incredible work being done by users at Whetstone schools every day.”

To learn more about how Whetstone Education supports teacher growth email sales@whetstoneeducation.org or visit www.whetstoneeducation.com.

About District Administration District Administration provides K12 leaders with critical news and information for school district management through its monthly magazine, website, e-newsletters and the District Administration Leadership Institute Superintendent Summits. For more information, visitwww.DistrictAdministration.com.

About Whetstone Education Whetstone Education was founded in New Orleans in 2011 by educators looking for an efficient, streamlined way to manage teacher evaluation data and feedback. The platform allows school leaders to capture, organize, analyze, and share teacher data in an intuitive interface, making it easy to identify teacher trends, and take action to help teachers grow. www.whetstoneeducation.com

Digital Readiness Checklist

Many of our partners join Whetstone because they are tired of using multiple tools in their observation and coaching process, and want one place to do it all. It’s hard to know if your district is ready to make the transition to an online system. We have created a five question checklist that will help you identify if now is the right time to transition to a digital solution.

Click here to download the Digital Readiness Checklist!

Want to learn more about Whetstone but are short on time?

Want to learn more about Whetstone but you’re short on time? Let us make it easy!

  • Check out our website - It’s a short intro to who we are and why leading schools like Uncommon Schools, YES Prep, KIPP, and Relay GSE all use Whetstone.
  • Request a video demo - We’ll send you a short video tour of Whetstone. No phone call required!
  • Schedule a 30 minute demo - Take a tour of Whetstone to see how the platform can help streamline your observation and coaching process.  
  • Try it for yourself - Like what you see? We will send you a link to the platform so you can see how easy and intuitive it is, and have your co-workers give their input.
  • Ready to say YES to Whetstone? Great! We’ll send you a contract and you’ll be on your way to using the platform this school year!

Find out how you can make the most of your coaching time!

Life Hacks for School Leaders: #5 - Stop Waiting in Line at the Airport

Leave policies at schools can be tough for people who live far from family and friends. Principal Ron Gubitz said that another time it’s tough to be a school leader is when “your friend is getting married and you want to travel on a Friday.” While you may not be able to change your district’s vacation leave policy, there are lots of ways to be more efficient in airports, which translates to more time for you to do literally anything you want.

Step 1: Get TSA Pre-Check. You can save yourself 30-45 minutes (or more) spent in line at the airport by signing up for TSA Pre-Check, putting you on an earlier flight out that may not have been possible otherwise. It costs $85 and is good for 5 years. If you fly 5 times a year, you’ve just given yourself 750 more minutes to play with your kids, plan professional development, talk with students’ parents, or just take a little time to do some reading for pleasure.

Step 2: Check in for your flight online. If you’re not checking a bag, there is absolutely no reason to stand in line to check in at the airline counter. Almost every airline has an app where you can not only check in for your flight, but also get a digital ticket that doesn’t require you to print a paper copy.

Step 3: Gate-check your bags. This other airport hack may sound strange, but it has made the difference in whether or not I’ve caught a plane in time. If you are checking a bag for your flight, you don’t necessarily have to check it before you go through the TSA line. As long as nothing in your bag is prohibited in carry-ons, you can take that big bag through security and then check it at the gate. The gate agent might look at you funny, but you’re far less likely to miss your flight this way, and you’ve successfully avoided standing in a 100-person check-in line.

Connect with Whetstone at the Ed-Fi Summit

Whetstone will be attending the Ed-Fi Summit from Wednesday, Oct. 12 to Friday, Oct. 14 in Austin, TX. As a licensee of Ed-Fi Technology, Whetstone supports the push to “empower educators with the information they need to make better choices for their students.” The Ed-Fi summit is a gathering of companies, organizations, and state and district leaders with an interest in making it easier to share data to give school leaders a complete picture of performance. Organizations that license the Ed-Fi technology can also integrate their data with the Ed-Fi dashboard which helps schools see all their data in one place.

If you are attending the Ed-Fi summit and would like to schedule a meeting with our CEO, please email allison@whetstoneeducation.com  

Life Hacks for School Leaders: #4 - Hire Someone to do a Low-leverage Task

Just because you can assemble furniture, doesn’t mean you have to. As a school leader or teacher, your time is much better spent on high-leverage tasks like analyzing student work to identify misconceptions than on putting together your latest purchase from IKEA. IMAGINE: you’re seated comfortably at your couch, re-writing lesson plans to incorporate new questions to push students to think analytically. Across the room, someone else deftly assembles your new kitchen table.

It’s not a dream! There are a bunch of services and apps out there that solve this problem for you. Taskrabbit is one service available in many cities that gives you your own personal assistant and handyman/woman. Here are the six categories of help they offer:

  1. General Cleaning
  2. General Handyman
  3. Moving Help
  4. Delivery & Shopping
  5. Furniture Assembly
  6. Lift & Shift Furniture

Taskrabbit is competitively priced, so if you have the means, consider it. Don’t want to use Taskrabbit, here are a bunch of alternatives.

Life Hacks for School Leaders: #3 - Get Toilet Paper Delivered to Your Door

I asked principal Ron Gubitz for a list of errands that are hard to get done when you’re a school leader. His first reply to me was “EVERYTHING.” When he finally made a list, I was struck by this one: “Buying ANYTHING from a store ever.” This item struck me because there is such a simple answer: online shopping. You can find ANYTHING online and have it shipped to you in a matter of days. At the Whetstone office, we’ve set up monthly Amazon shipments for staples like printer paper, toilet paper, and La Croix. If you can do it for the office, why not at home? Set up monthly Amazon deliveries for pantry staples like paper towels, aluminum foil, band-aids, and kleenex. Beyond the ease of having these items come right to your door (in two days if you have Amazon Prime!), keeping your cupboards stocked with auto-deliveries will shorten the length of your trips to the store when you absolutely have to go.

Life Hacks for School Leaders: #2 - Your Phone is also a Bank

If you haven’t yet switched to online banking, now is the time. If you are a school leader or teacher, your time is far too valuable to go out of your way to get to the bank and sit in your car waiting for the ATM. And, in 2016, there is almost no reason to go to an ATM! Most major banks now have phone apps that allow you to do pretty much anything you would do at an ATM -- including depositing checks -- from anywhere. Need cash? Get cash back the next time you’re at the grocery store or pharmacy and combine two errands into one. In addition to replacing the ATM with your phone, save yourself even more time by setting up your recurring payments. Just do it. Sending a check to your landlord or mortgage company each month may not seem like a huge lift, but beyond writing the check, it requires you to keep checks, envelopes, and stamps stocked, and remember to send it. Teachers and school leaders have better things to do. If you set up recurring payments through your bank’s online platform (and almost all banks have one), you can pay every bill -- rent, health care, electric, water, etc. -- without even thinking about it. If you estimate that it takes about 5 minutes per bill to read the bill, write the check, address the envelope, and put it in the mail box , then you can give yourself back 20-30 minutes a month (add 30 minutes if you have to go to the store to get envelopes or stamps) to spend with your family or tie up loose ends at work. Why wouldn’t you give yourself this time back?

Whetstone to Attend the Utah Digital Teaching & Learning Bootcamps

Whetstone will be attending the Utah Digital Teaching & Learning Bootcamps from Monday, September 26 to Thursday, September 29. This event supports the Utah Digital Teaching & Learning Grant Program and the goal of leveraging education technology to its full potential in the state. Attending the event are district leaders from across Utah supporting their schools by providing them with digital tools and resources to support their student and teacher-based performance goals. We look forward to meeting these leaders and discussing how Whetstone can support their digital initiatives. If you are attending the bootcamp and want more information, please contact allison@whetstoneeducation.com.

Life Hacks for School Leaders: #1 - Dry Clean at Your Desk

School leaders and teachers are the busiest people I know. They get to school before most businesses open and leave after most close. Rarely do they get to leave campus to run errands on their lunch break, so it’s nearly impossible to make it to the dry cleaners, the bank, the dentist, or even let in the cable guy. Whetstone’s mission is to build technology that makes life easier for instructional leaders. While we haven’t yet created a dry cleaning app (maybe someday!), we’re starting a series of weekly time-saving life hacks for school leaders and teachers to help redirect their time to what matters most: their students and families.


Most dry cleaners are only open 9am-5pm and rarely on weekends (so convenient!). And, as far as I know, iPhones still can’t do our dry cleaning for us, sadly. But, if you can’t get to the cleaners before it closes, a handheld steamer can get the job done in a pinch. I keep a steamer at the office and use it to dewrinkle when necessary. They’re cheap, portable, and can get you an additional one to two wears out of a suit, which is a lot of time (and money!) saved at the dry cleaners.

CEO, Libby Fischer to Attend the Forbes 30 Under 30 Summit

A member of the Forbes 30 under 30 in Education class of 2016, our CEO, Libby Fischer will be representing Whetstone at the 3rd Annual Forbes 30 Under 30 Summit in Boston, Oct. 16 to 19. Recognized as the "greatest gathering ever of young entrepreneurs and game-changers," this event brings together alumni of the Forbes 30 under 30 recognition with over 5,000 of the brightest in Science and Technology, Finance and Investing, Media and Creativity, and Policy and Social Good.