Adapting to the unexpected: Lessons learned from 2023

Illustration by Robert Askew for Kate Leto

Earlier this year I was in a coaching supervision session and the topic of “flow vs. structure” came up. Just in case you’re not familiar with what a supervision session is, it’s when a few coaches come together with a certified supervisor to talk about challenges we’re having with our work—be it questions of ethics, our own emotional responses to the work, how we’re handling a certain client situation, or just general frustrations.

The topic came from a comment someone in the group had made about the amount of preparation he was putting into a group coaching session and wondering if he was being so meticulous in planning that he was making it impossible for there to be any moments of spontaneity or flow in the session. 

We all jumped onto the topic and found different ways we could relate as well, be it in planning for workshops,1:1 coaching sessions, new business conversations, or even public speaking opportunities. 

We talked about the idea of play and creating space for the unexpected in our work. There was no real outcome from the conversation, but I left feeling that my fundamental approach to work was the polar opposite of flow and spontaneity.   

But then frequency illusion kicked in—a cognitive bias where people who notice something new, like a word or object, begin to encounter it frequently—and I felt like I started to be confronted with the unexpected at every turn. 

Don’t get me wrong—I have stayed true to a lot of what I said I would do this year. I’ve kept the focus on leadership development in the product and digital transformation space and have spent a lot of time in coaching sessions with amazing people from around the world. I’ve loved every minute of that. 

But there were a few unexpected opportunities that came my way this year that have made all the difference. 

Being open to feedback

The first was that I had a 360 review of me done this year. The idea came up, unexpectedly, over lunch with a friend and colleague early in the year. I had mentioned that as a solo entrepreneur for over 12 years, it had been more than a decade since I’d had any structured feedback and that I was so curious what that might be like now.  I was offering 360 reviews for my clients, so surely I should have one done for myself … right?

My colleague picked up the comment and offered to help me make that happen. She spoke to a handful of peers and clients about my strengths and areas of improvement.

Honestly, I was pretty nervous about the outcome. What if everyone told me I was really no good at what I do and I had to start all over… somehow!? That was certainly not part of the plan for 2023.

But luckily, that’s not what happened at all. The feedback was good, including lots of positives and areas to think about that I never would’ve picked up on my own. 

Giving new and unexpected ideas a chance

From the 360 feedback came ideas that were nowhere on my radar this year—most notably my Essential Coaching Skills for Product Leaders short course that I launched as a beta in Q4. This idea came up when talking through my feedback, and it just felt right. It would combine my background in training with an area of focus that I love—leadership coaching —in a very unique offering. It was unexpected, but I was suddenly convinced that it made sense to move in this direction.

The feedback also stoked another idea: my desire to have some honest, open conversations with other product people about their own experiences as “leaders.” I wanted to explore the challenges they’ve faced and how they’ve impacted them as people and leaders now. So, from that came a first few Leadership Lessons conversations with Jonny Schneider and Randy Silver.  

While many may not know this about me, I’m a bit of an introvert.  The idea of actually reaching out to colleagues that I respect to have this conversation and share it publicly is a pretty big thing for me, and I’m happy to say, an unexpected pleasure. 

I'm sharing these stories in the hopes that they might inspire your curiosity into what 2024 might hold for you. Do you see an area where you might be too rigid and closed off to the unexpected? How could you invite feedback or cultivate a more playful and open environment where new ideas get the chance to grow?

What’s up for 2024?

While I’ll continue my core offerings of 1:1 Leadership Coaching, Leadership Team Coaching, and Corporate Executive Coaching Engagements, I’m going to build on my two unexpected gems and offer Coaching Skills for Product Leaders again in 2024. I’ll be announcing dates for Q1 in January.  Sign up to the waitlist here to be the first notified. 

I’m also going to continue to play with my Leadership Lessons interviews as a format. Will it be a webinar? Podcast? I’m really not sure yet, but I’m eager to explore it more.

The highlight of this experience is that every aspect of it - from the discussions during supervision to the impromptu 360 lunch conversation, the valuable feedback and everything that has resulted - is attributed to the presence of an amazing network of colleagues, peers, clients, coaches and supporters. 

So what about you? How can you make space in your life for the unexpected in 2024?