The story of Coaches:  Taking corporate mentoring from cute to crucial

The story of Coaches: Taking corporate mentoring from cute to crucial

Brett Hicks's Layout avatar

In late 2018, Flywheel was right in the middle of full-fledged scaling. We had 110 employees at the end of 2017, hired nearly 100 new employees in 2018, and just like that, we went from a small startup to a booming business practically overnight. We wanted to avoid as many growing pains as possible, so we began looking for ways to increase employee engagement, improve cross-company collaboration, and level up our managers (and therefore, our whole organization). Ah, piece of cake, right?

I know what you’re thinking: Flywheel offers free lunch, leisurely scooter rides, and office dogs at their disposal, how could our employees ask for anything else? While those are quite delightful perks, what we really care about is making sure our employees are constantly leveling up. We’re all about that We are hungry life, one of our core values that means we challenge the status quo and constantly push to be better.

Brett Hicks, Training & Development Manager, leading New Employee Onboarding (or NEO!)

As the manager of Training & Development at Flywheel, I was searching for solutions on the aforementioned challenges and then had a revelation.

We don’t have any formal mentorship here. Maybe that could help?

But, I immediately snapped out of it because we’re a tech startup after all,  and a mentor program smelled suspiciously corporate. But then the thought continued to linger:

Okay, but what if we did it with a ton of intentionality and made sure that 1) it didn’t feel like blind dating by choosing the pairs based on perceived compatibility. And 2) it didn’t feel aimless; we would set goals and have an established end date. Without them, both the mentee and mentor could be left wondering when they’ll be done.

So, I went with my gut and Coaches was born. (We branded the program just like we brand everything at Flywheel, hence the name!) Coaches has become a crucial part of leadership development at Flywheel and we feel so strongly about its impact that we want to share it with the world so other organizations might score big with it too!

How it works

Coaches is a mentorship program for managers and rising stars at Flywheel to be counseled by a more senior member of our leadership team on a specific area of focus. While that’s the elevator pitch, I promise it offers so much more! So, what makes it different from any other mentor program? Great question! 

  1. Focus: Flywheelers apply to be coached on a specific topic. While you could have mentor meetings feel more abstract and open-ended, we like that this focuses our Coaches pairs, allowing them to make progress specifically towards a set goal.
  1. Thoughtful matching: Mentees are paired up with an in-house leader based on that leader’s expertise with the topic applied for. Although we consider personality compatibility, we think that knowledge in the area someone wants to grow in is of greatest importance. A small team at Flywheel thoroughly dives into each application and determines who will “Coach” who.
Keegan Mahoney, Engineering Manager and Karen Borchert, COO
  1. Kickoffs: As the owner of the program, I facilitate “Coaches kickoffs” with every single pair to get them started a 30 minute guided conversation to set expectations, establish a goal, and document a go-forward plan for the participants. 
  1. Quarterly: We run the program quarterly so new applications are considered regularly, pairs have a clear end date, and they feel motivated to get shit done in a set timeframe.
  1. Deliverables: There’s a deliverable at the end of the quarter. Coaches pairs meet weekly to chip away at their established goal so they can showcase that sweet, sweet progress in a presentation at the Coaches Retro: a grand meeting with our Senior Leadership team and all other mentors and mentees from the quarter. 


In what world does the VP of Finance spend 12 weeks with an Engineering Manager to teach them about SaaS metrics, the in’s and out’s of the company budget, and how to relay this information with their team to make better financial decisions? In the world of Coaches, it does!

It’s not all talk, either. We’ve seen some seriously rad results: from our CPO coaching a Lead Copywriter on strategic messaging and value-selling product marketing to the VP of Sales working with our Product Design Manager on designing and implementing effective processes and improving cross-team and departmental collaboration. Our Director of People ran mock 1:1s with a Regional Support Manager to help him sharpen his emotional intelligence with his team. Another pair, working on improving written communication skills, ran timed writing exercises each week that were peer reviewed.

“Talking with someone outside of my usual area of influence got me thinking in different ways and helped me zero in objectively on my challenges.” – Ben Turner, Happiness Engineer Coached by our Director of Customer Success, Liz Maloley.

This is one of the best “re-recruiting” efforts we have at Flywheel. The mentees learn something of course, but the real magic happens because of the extended face-time and relationship building they get with senior leaders and decision makers at the company. 

“Coaches grew me professionally in so many ways that weren’t even tied to my quarter’s goal. Being able to get to know a leader in the company that I don’t interact with typically taught me tons of new ways to look at things.” – Ashley Lewin, Growth Marketing Lead Coached by our VP of Customer Experience, Kaitlin Grohmann.

Kaitlin Grohmann, VP of Customer Experience at Flywheel

Coaches doesn’t stop when the quarter is up, either. As of this spring, our Engineering leadership team launched the Engineering Mentor Program (EMP), a new department-specific program dedicated to advancing software engineers in their technical abilities. EMP was created based on Coaches, using all of its core pieces to maximize its success. See? You can make your mentor program your own while still using the key, transferable pieces of Coaches! 

Coaches takes the idea of a corporate mentorship program and totally flips it on its head. It’s not about the company’s bottom dollar or being more productive, it’s about striving to be a workplace of choice and truly caring about our employees’ professional growth goals. We’ve had 27 Flywheelers get Coached over the past year and a half, and we continue to see the needle move on both employee productivity and engagement. Try Coaches out at your company and watch your people thrive!

Flywheel’s Product and Engineering team

Have a question about Coaches? Leave it in the comments below!

Comments ( 3 )

  1. Carol Zuegner

    September 21, 2020

    I add my kudos to this. I think there are lessons for my students in their Entrepreneurial Capstone about being intentional with mentoring and advice. I do think mentoring is crucial -- I often use what I call reverse mentoring, which is similar to what you are doing. I ask my alums out in the workforce to help me figure out what I should be teaching and how to do it. I have generous alums, but it is so helpful to me.

  2. Megan Lane

    August 20, 2020

    Bravo! Professional development is an instrumental part of individual growth. What a fantastic idea!

  3. Keegan Lanier

    August 11, 2020

    This is incredible. I'm so intrigued by the specifics of the structure. I'm really intrigued by the startup meeting. Great job being super intentional and not allowing anyone to get into the professional growth rut that can happen.

    I'm a person who has to continually evolve and grow so I truly appreciate this!

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