On trying, and failing...

Feedback, flaws and the discomfort of change

Hello Wayfinders,

I hope your week is more encouraging than mine, but if you, too, are dwelling in disappointment or frustration, read on. You’ll feel less alone. Maybe you’ll discover something.

I did.

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Several months ago I was pondering how we might build our city’s women leaders' social, human and community capital. I’d worked in leadership development in our community for a few years and was increasingly aware that women face more complex challenges in career progression than men. No news there. I’ve seen this in every city where I’ve lived and worked, but somehow, it felt more pronounced in our regional community. Intractable, perhaps.

I got talking to other women in town. Women in positions of leadership. They saw it too. They felt it. They knew it.

Buoyed by these discussions and drawing on my experience designing development and capacity-building initiatives, I devised a forum for learning, support and exploration called Trail Blazers: a small group coaching and peer learning program for local women leaders.

Trail Blazers was designed for women who:

• Are grappling with complexity and change (disruptive tech, hybrid work modes, staff wellbeing, diversity and politics, not to mention families)

• Are keen to build their network of purpose-driven local women leaders for ideas, insights, exploration, connection and support.

• Are responsible for others - organisations, teams and families - and feel that responsibility acutely.

• Love to learn and the challenge of thinking differently.

We’d meet either online or face-to-face once a fortnight over two months. As a launching point for conversation, exploration, and problem-solving, I would provide insights and updates on contemporary leadership topics. Participants would bring their day-to-day challenges, experiences and ideas and share and workshop these in a supportive, ‘we’re all in this together’ manner.

The goal was to work collectively and face today’s challenges to smooth the path for the women who follow tomorrow.

So far, so good.

I did ‘all of things you’re supposed to do’ to design and promote a new learning initiative. I sense-checked the idea with prospective participants, hosted an online webinar to co-design and engage, and used email and my social media channels (with sizeable followings) to promote it. This is not my first rodeo.

The idea was well received. Conversational feedback was positive and supportive. The algorithm liked my posts—lots of ❤️s and comments. People who don’t live locally said they wished they could join in.

‘I might be on to something here,’ I thought, and pressed on with a website and registration portal.

I figured I’d keep it small. This would be a pilot with the potential to grow in size and scale. I was happy to experiment and collaborate with my participants to build something valuable and workable. Ultimately, it would connect women in our city to create a scaffold of support, ideas, initiatives and collaboration to create positive change. This was a systems change* initiative, after all.

I launched registrations, giving myself plenty of time for further promotion. Web site visits were up. People were curious.

‘I only need a small group to go ahead,’ I said, setting a deadline of this week to hit my target of six paid participants.

I didn’t get six.

I got one.

Oh dear.

As excellent as that one woman is, and as thankful as I am for her support and trust, I couldn’t proceed with one participant. The model just wouldn’t work. I canned the idea.

Today, I sit in disappointment, tinged with despondency.

It’s uncomfortable.

But this is not a pity post. Nor is it forced positivity. I’m not here to tell you that I ‘believe in myself’ and I’ll try again, aiming for a different outcome. Reflecting on the experience, I can see the flaws in my strategy, marketing and promotion. I didn’t build a big enough audience at the outset. My copy didn’t convert. I didn’t know my audience and their barriers to participation well enough. My offer wasn’t valuable enough to push through those barriers.

If this were a genuine experiment, I would revisit each element of my program design, marketing and promotion, adjusting each variable individually while controlling the others. I would establish exactly where I failed and then try again.

I’ve discovered two flaws in this plan, however.

#1 This is not a simple linear input-output model. As I shared in this LinkedIn post three weeks ago (but promptly forgot and thus ignored my own advice), we've been taught that when creating something new, we need a well-articulated plan, and the path to success is executing that plan. Or, when it comes to revising the plan, we review, revisit, control what we can and test again, just as I’ve described above.

A linear input-output model like this works if you are:
🔨 Constructing a building
🚀 Launching an already tested product or delivering an event
📝 Executing a financial plan

It doesn't work if you are:
🌱 Designing a new product
👩‍💼 Developing a new idea
🎯 Creating change

Why?

Because you can’t control every variable in new ideas and initiatives that seek to create change in complex scenarios, like people’s work, life and communities.

You may not even be able to identify them.

We’re all immersed in a context of ever-shifting variables, including economic conditions, workload, others’ needs and expectations, budgets, mood, mindset, and readiness to change, which influence our decisions almost moment by moment. How do you prepare or control for that?

Developing new product or program ideas - or any initiative - designed to create change, requires a different approach. Something that looks a little more like this:

This 👆 is an excellent reminder that to create change, it’s imperative to ‘zoom out’ and remind ourselves of the greater goal we’re working towards. My goal was not to run Trail Blazers, the coaching program. It wasn’t to raise revenue (although that always helps). My goal was to use my skills and experience in a way that felt meaningful to me, to enhance the capacity and capability of our community.

My launch of Trail Blazers was intended as an idea - an input I was inserting into the world to gain feedback in pursuit of that greater goal. If it was a roaring success, fantastic. The fact that it wasn’t, prompts me not to rejig and promote and try again with the same program but to step back and consider alternate routes to my goal. Many roads lead to Rome.

#2 My second fatal flaw: I fell into the trap of moving too quickly to a ‘solution’ rather than exploring and understanding the problem and considering how it might be addressed differently. (A trap I teach others to avoid. Oops!) In Design Thinking terms, I jumped to Prototyping before fully Empathising, Defining and Ideating.

Perhaps, I’m a little hard on myself. Maybe this is less ‘fatal flaw’ than a reminder of the messiness of being human. We all jump to quick decisions and action in favour of sitting with the discomfort of contradictions, ambiguity and uncertainty. Who wants to muddle through that when we could have a clearly defined ‘eight simple steps to success’? Isn’t that the promise of every silver-bullet scheme?

What’s next?

I’m not returning to the drawing board. I’m assessing the progress I’ve made, the allies I have, the support I need, the learning I’ve uncovered and the story I’m telling. I’ll reframe uncertainty as curiosity, remind myself of my purpose and continue to experiment, taking small steps.

Maybe Trail Blazers will return, renewed. Worthy ideas find their way.

Maybe it won’t.

Time will tell.

In the meantime, I’ll happily muddle through the messiness, using every experience as an opportunity to reflect and grow because that’s the path to transformation and positive change - and if we’re not here to do that, then why are we here?

Onwards and upwards,

*Systems change aims to bring about lasting change by altering underlying structures and supporting mechanisms that make the system operate in a particular way. These can include policies, routines, relationships, resources, power structures and values - New Philanthropy Capital’s 2015 handbook.

The Fun Stuff:

I’m watching: Will and Harper - or at least I will be this weekend.

I’m reading: Construction drawings. We’re seven months into the construction of our new home and it’s surreal making decisions about the orientation of light switches and what colour the door handles should be.

I’m working on: Course content as I prepare to teach units in the ‘Leadership and Place’ subject of the University of Tasmania’s Executive MBA program. It’s exciting to be part of this innovative program.