Looking back to look forward

Kate Leto
4 min readJan 8, 2023

How a retro of past work helped me shape my new year

Illustration by artinker.com for Kate Leto

After closing the workshop outline from 2018, I opened a document from last summer that was a retro for my first six months of 2022, capturing insights and patterns from client session along with my own personal reflections and client feedback.

I found that the essence of the four points listed in 2018 were still very much present in my work. My coaching practice is built on the idea that leadership — be it in product, design, engineering or beyond — isn’t easy to understand, define or embody. That leadership skills can be developed, and that the foundation of the learning comes from a strong understanding of yourself.

From my summer retro, I also found that what was helping to create change and building confidence for my clientswas offering a safe space for them to really discover what leadership means to them. Not what leadership means to me or a leadership guru or even super successful business person, but what it means to them. Then to help them build a way of working, behaving and leading that reflects their own authentic style of leadership.

How were we getting there? My 2022 retro showed that there wasn’t a specific framework or approach that was resonating more than another. Instead, our work was based on building awareness and understanding of actual day-to-day experiences at work; learning moments in the every day. These are “trigger points” or “moments that matter.” They might include things like working on OKRs, doing a presentation, giving/receiving feedback, hiring, figuring out priorities, building strategy, handling tension and conflict, having 1:1s, speaking with stakeholders … the list goes on. Identifying your authentic approach to leadership lives in all of these moments and in my coaching sessions we dug into them by asking questions, challenging beliefs and going deep on experiences, emotions and actions.

Outcomes of client work then and now vary greatly by client. In feedback, clients said they were able to create new confidence and clarity in leadership, grow relationships with team members and stakeholders and in some cases, even became more clear on the type of leadership roles that felt right and those that didn’t.

There was also some very helpful growth feedback for me, in that some clients at times felt the need to have more of a directive approach with feedback based on my experience vs. coaching. This is always a tricky one for coaches — as I default to coaching vs. advising and directing. But I also appreciate at times there is a need to strike a balance and that’s something I want to experiment more with in the new year.

So what does this mean for 2023?

Looking forward to 2023

First of all, I’m really excited to carry this work and learning into 2023. Leadership coaching for product people energises and challenges me. I truly, truly love the work I do and seeing people evolve and grow before my eyes.

For that reason, the core of my offerings in 2023 will continue to focus on working with Product leaders and executives — that includes those in product management, design and engineering.

I’ll continue to offer 1:1 coaching through my personal coaching practice as well as working with individuals and teams in organisation-wide engagements. I have limited availability for individual coaching in Q1, so please get in touch if you’d like to learn more.

I’m also leaving space in my practice to explore and try out a few new things. Top of my list this year includes:

  • Group leadership coaching offering — This is something I’ve been asked about for quite some time. I’m exploring different options, partners and formats for a group coaching offering. If you’d like to be the first to hear about my offering, please send me a note here.
  • CPO Coaching offering: Focusing on the unique leadership challenges and opportunities that Chief Product Officers face in different phases of a company’s maturity. I’m at an early discovery phase with this concept, so again, if you’d like to hear more about the offering as it comes together, please get in touch.

To round out my year, I’m also prioritising learning about supporting Neurodivergent clients, and of course, working with my own coach to continue to explore how I can grow as a leader, coach and business owner.

Thank you for strolling down memory/retro lane with me. Looking back and writing about it has helped me to draw a line between where I’ve been and where I want to go. To my surprise and delight, it’s a more consistent and aligned path than I expected. I hope you’ll take time to do something similar and share your findings with me.

Here’s to a healthy and well new year for all!


Originally published at https://www.kateleto.com on January 8, 2023.

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Kate Leto

Product Leadership and Executive Coach. Learning to love tea.