The Why of Coaching
Success, Failure, and the Path Between
I was running my first startup when the COVID pandemic began.
In 2019, we’d had a banner year - 112% year-over-year growth, new faces in every department, multiple enterprise clients coming on board, negative net churn. We had raised a meaningful Series A, and then made room for a bit more in a follow-on A1. We opened our first real office, designed from the floor plate up to accommodate our growing team, and the future felt bright. In many ways, I thought we’d "made it” - after 5 years of struggle, so many late nights, even buying a cot where my co-founder could sleep when work kept him in the office for weeks at a time, I believed things were going well and getting easier.
But, the founder journey is unpredictable. There are so many variables that impact us - competitors arise, markets change, investors lead in or out, employees leave or manage themselves out. And for most of us, our companies are tightly woven into our identities - when business goes well we feel good, and when it’s challenging, we internalize it.
I have lived this experience; 2020 saw my first company drop to 1% growth. With incredibly hard work from our team, we retained our customers, but as the foundations shifted beneath our feet, we pivoted the business, rebuilt our sales organization, and did our first (and hopefully only) ever round of layoffs. We eventually hired an investment banker, ran a comprehensive process, and sold the business.
During that time, I was fortunate enough to have an astounding CEO coach - and it opened my eyes to what coaching meant.
My time working with my coach was primarily an exercise in him asking questions, and asking if I’d noticed certain things, and then discussed what I might have missed. At critical junctures - such as preparing for that round of layoffs - we talked through not only the business implications, but how I was internalizing it, and how that came across to the people directly impacted by our decisions. We worked through my guilt, shame, and fear in detail - and over the course of our sessions, I found my footing. I was able to more authentically and fully show up for our employees, my leadership team, and our investors — and help balance the needs of the business and of the humans we had to part ways with without my emotions getting in the way, but also without pushing them down.
That, I believe, is the “why” of coaching. It sits at the intersection of the internal experience we’re having, and the work we’re doing - and done well, it allows us to be more present, to make decisions and trust in them, and to meet the moment in front of us.
It’s also the why behind FounderTack, and the approach taken when coaching. If you’re interested, intrigued, or ready, reach out. Let’s talk.
