Our team spent 3 days with an executive coach working on Groove. Here’s how it went.
Last month, much of the world was winding down for the holidays.
We were all getting ready to take some time off, get together with our families and friends, and do anything but work for a few days.
But before the Groove team celebrated the holidays, we had one thing left to do.
In the second week of December, the leadership team—me plus the three people in charge of each of our core functions (marketing, development and customer support)—traveled to New York for an experience that would change the way we looked at our business.
Over three days, we took a hard, top-down look at Groove, at where we are, where we’re headed, and where we want to be.
We questioned everything.
We learned new things about ourselves, about each other, and about how we can work better together.
And we had some very valuable help.
Why We Hired A Business Coach
As I said in the announcement, David’s cash wasn’t what we were after. It was the value he could add as an advisor.
At the time, we had three primary expectations from the relationship:
And while David began delivering very quickly on these—his feedback on our very first monthly update caused us to make important changes to our strategy—he also brought a fourth benefit when he introduced the idea of working with a business coach to help us grow.
To be honest, this wasn’t something that I had thought about much before.
I had gotten a lot of value from connecting with mentors and other advisors, but hadn’t considered actually paying someone to coach us.
But as soon as David suggested it, it made perfect sense.
It would be an investment—good business coaches run anywhere from $1,000 to $10,000 per month or much, much more—but if it worked, the value could be tremendous.
I saw two specific reasons why the business coach ended up being a good coach, he could be really valuable for us:
- Accountability: At the end of the day, our team had been accountable to nobody but ourselves for the growth of the company. Particularly at the top, nobody is holding our feet to the first and regularly asking us: “did you accomplish what you set out to accomplish?” It sounds simple, but having someone whom you’re accountable to can be a big motivator to push yourself. The fact that we’re paying for that accountability gives us even more skin in the game and reason to follow through.
- Process: He is an expert at process. We aren’t. We might be very good at building help desk software and selling it, but that’s not enough to grow to where we want to be. As much as we’re proud of how far we’ve come, we’ve grown through being scrappy, moving fast and breaking things along the way. While we’ll continue to keep those values, he could show us (and keep us accountable for) the systems and processes that would help us truly scale the business in a predictable and repeatable way.
In every single sport, the competitors at the very top of the game got there, at least in large part, because they have a great coach.
In an interview, Darya Klishina, one of the top long jumpers in the world, was asked what the key to her success was.
“I trust and believe in my coach.”
Coaches give athletes accountability and process, and my hope was that ours could do the same for us.
What We Did For Three Days
Before the retreat, the entire team fill out lengthy questionnaires about how we each see the company and our roles here.
We were asked about our strengths, weaknesses, strategies, vision.
How we all felt about the direction of the company, and whether or not we’re headed the right way.
We also completed DISC assessments, a personality test of sorts.
We didn’t really know what we were going to do with this information.
I wasn’t quite sure what to expect, but I was excited.
We kicked the retreat off with a team dinner.
(Clockwise from left: Jordan, Len, David, Alex and Lesley)
And that was when our coach pulled out the first surprise he had in store for us: Cards Against Humanity.
Not your typical business meeting activity.
We played for an hour or so, and it’s fair to say that the ice broke very quickly. If you’ve never played CaH before, a quick Google should clear things up.
After a few more drinks, we went back to the apartment and watched some TV before calling it a night.
*Note: If you’re planning a retreat for your distributed team, *****try to rent a shared living space as opposed to hotel rooms****. The bonding that happens in those moments—the evenings sitting on the couch watching TV, the shared breakfasts, etc.—was among the most valuable parts of the entire retreat.
The next day is when the real work started.
We set up the living room and plastered the walls with the team’s responses from our surveys.
He took us through a 30,000 foot view of the company and helped us all better understand the pulse of the team. As a team, we assessed how the company was doing on each of the ten Rockefeller habits.
He had us share our own ideas for what we should be focusing on, and how we could do better.
And most importantly, he forced us to look at the deeper meaning of Groove, and why we’re doing what we’re doing; a question we never really have much time to think about in the trenches.
To understand what I mean, I highly recommend taking a few minutes to watch this incredible talk by Simon Sinek:
We spent much of the time on big questions like that, rather than the tactical decisions we typically make on a day-to-day basis.
Things got a bit messy:
And we set new goals for the first quarter of 2016 that we’d be accountable to our coach for accomplishing, and that we’d evaluate at our next quarterly retreat in April.
In the end, we came away with more clarity and determination than we’ve had since we started Groove.
I can say, without hesitation, that I’ve never been more excited about what lies ahead.
The Team-Building Benefit Of Coaching
As a remote team, we don’t get the chance to get together that often.
And for a couple of us, this would be the first time that we met in person.
Getting that time together was so, so important. We gelled more in just a few days together than we’ve been able to in years on Slack.
For a team-building exercise, we booked an “Escape The Room” session that had us solve problems and look for clues to get out of a locked room.
And we visited the top of the new One World Trade observatory, which was incredible.
As great as being remote is, there truly is no substitute for in-person meetings, and this retreat reinforced that for me. In addition to these quarterly leadership retreats, I plan to prioritize getting the entire team together a lot more in the next year.
How To Apply This To Your Business
I’ll admit that I was skeptical about hiring a business coach at first, mostly because I didn’t know what to expect.
I pictured Alec Baldwin from Glengarry Glen Ross subjecting us to hours of sports cliches and motivational quotes, and I was nervous.
But what we got was hugely valuable. It helped us look at our business in a way that we had never done before.
And it gave us direction and accountability for our future growth.
If you’re on the fence about hiring a business coach, I’d urge you to give it a try.
You can find coaches at all price ranges.
Some are better than others, but focus on finding someone who can hold you accountable (not hard) and help you develop a playbook for success (harder).
If your experience is like ours, you’ll be glad you did.