The Test Comes First
What a board failure, a botched software rollout, and too many awkward emails taught me about learning the hard way.
I had a really difficult professional setback 3 years ago. It was one of those experiences that I still think about and haven’t been able to let go of completely; it comes up unbidden at random times, and I grimace like I am back in that painful time. In short: a company for which I served on the Board of Directors went out of business.
A close family friend who knew what I was going through back then gave me encouragement and support. He said, “Experience is the hardest teacher, because you get the test first and the lesson after.”
At the time, I just felt comforted by his words. I was someone who prided himself too much on always getting things right. Now I had to incorporate this failure into my story, and my friend’s advice gave me a way to fit it in without completely tearing down my identity.
Over time, I’ve thought more about that line — you get the test first and the lesson after — and the other ways it applies. It got me wondering how many experiences I had avoided out of the fear of not passing the test, and therefore how many lessons I never learned.
We have a few big pieces coming up soon here on the Chorus Consultant Community and in the Strategic Agility Series, so the article today is shorter than usual. I want to share some of the tests I failed and the lessons I learned after. Hopefully it can be a small nudge to everyone to embrace the experience knowing full well you might not pass.
Thinking I could persist through a leadership transition
I had a longtime client with whom I had a deep and trusting relationship, including with the Executive Director and other senior leadership. I provided value and went above and beyond many times over the years. Then, they had a leadership transition. I thought for sure my contributions were unimpeachable, and the new ED (who had been on the senior leadership team) would want to retain my services ongoing.
Well, that didn’t happen.
But I learned something. I went into the new relationship trying to just port over the previous arrangement and thinking we’d continue as before. I should have treated it like an audition for a new contract. Maybe I had my foot in the door, but this was a new prospect whose business I had to win. If I could do it all over again, I would have done a discovery meeting, submitted a proposal and SOW, and negotiated brand new terms. I still might not have converted the contract, but I would have improved my chances.
Saying yes to a project I didn’t know how to scope
I had one engagement that started off with general strategic advising on financial planning and Board engagement and communications. Then the client asked me to manage deployment of a large-scale new software solution.
I was excited to take this on and said “yes.” But I had never overseen a project like this before. My time expectations proved unrealistic, and the project went several months beyond my original plan. The problem was that I was due to start my parental leave after Labor Day, but the project wasn’t finished. I didn’t give myself many good options, so I just had to tie things up and transition them to a staffer as well as I could. I am not proud of my work on this.
Next time, I would get some advice from an expert before taking on a big new project. Then, I could do accurate scoping of time and resources needed before committing to the work.
Being too transactional and not having a real plan to stay in touch with people
Raise your hand if I’ve ever sent you an email out of the blue after more than 5 years of no contact asking you for something…
So many hands up. Ack, the shame!
I’ve done this so many times, I can’t keep track anymore. Lately, I made the mistake of assuming as long as I offered something useful in return, folks would want to take me up on it. Wrong. Again.
What I’ve learned is people want to help each other if they have a good relationship. That doesn’t mean we talk on the phone once a week. We don’t really have to be in frequent, regular contact. But we do need to have a basis for our relationship rooted in personal connection, not transaction.
So, I’m trying to be better about this. My barrier isn’t interest or caring, either. It’s just time. Cultivating flourishing relationships (or at least healthy ones) takes time, and that’s always short. However, in a business that’s all about relationships, it has to be a top priority.
There’s a thread running through all three of these. In each case, the version of me who showed up believed he already knew enough. I knew my client relationship was solid. I knew I could figure out a software deployment. I knew that offering value in an email was sufficient to rekindle a dormant connection. The confidence wasn’t arrogance, exactly; it was more like a refusal to feel the discomfort of not knowing. And that refusal is what made the test so much harder than it needed to be.
My friend’s line has lodged itself somewhere permanent in me now, the way the best advice does. I catch myself applying it in real time. When something feels uncertain or exposing, when I notice that familiar tightening in my chest that says you might not be good enough for this, I try to hear it differently. That feeling is the test arriving before the lesson.
I still haven’t fully let go of the board failure, but I no longer try to fit it into a tidy narrative about resilience or growth. It just sits there, a little jagged, reminding me that I learned something I couldn’t have learned any other way.