This week I’ve been reflecting on a client workshop from last summer that I still remember to this day. My immediate post-meeting notes have been sitting in my Todoist for too long and really deserved knocking into shape for a Build article.
The workshop in question has to go down as one of the most memorable I’ve had since I started working with in founders in 2014.
It’s a story of being stuck in the middle.
Sitting in a glass-sided meeting room in a London co-working space, I was literally positioned between two high energy founders.
And they completely fitted the classic visionary and integrator pairing.
One founder kept jumping up to sketch their grand ambitions on the whiteboard whilst the other was often deep in their laptop, pulling up spreadsheets showing why we couldn’t afford to do this or that.
And there I was as in coach and facilitator mode, caught in the middle and once again mediating between misaligned leadership.
Re-reading the notes from that day got me thinking about something I’ve noticed after working with dozens of founder-led growth businesses since.
When companies stall – bumping around at the same revenue for years – it’s rarely really about market conditions, the threat of AI or the competition.
It’s about this fundamental tension at the top table.
The pattern is almost always the same.
You’ve got one camp that’s completely future-focused. They’re the visionaries, energised by potential and painting pictures of what could be. But they’re often so zoomed out they can’t see what’s actually holding the business back day-to-day.
They get frustrated when you explain that before you can grow, you need to reset. You need to build the platform that makes growth possible. (I’m usually the person doing that explaining when I’m in fractional COO mode btw).
Then there’s the other camp. Rooted firmly in the here and now.
These are your operators, focused on how things actually work, on team performance and creating some operational stability. The people who know exactly why that brilliant new initiative will break three existing processes.
Having reflected on my own leadership and sitting in this seat, I recognise that people here can sometimes be too cautious to see what could happen ahead. They want to perfect the current business model before moving forward – which in the real world means never moving forward at all.
And here’s where it gets properly difficult.
Both perspectives are valid. Neither’s right or wrong. Both are necessary. The visionary without the operator builds castles in the air. The operator without the visionary builds increasingly perfect CD players whilst the world moves to streaming audio (I fear I may be showing my age with that analogy).
But when these two world views clash? That’s when businesses get stuck.
You start seeing it in meetings. Different priorities start surfacing in every discussion. Parallel tracks develop where there should be a single plan.
The strategy gradually erodes as actions become reactive, disconnected from any coherent direction.
Over time progress will slow to a crawl. Founder relationships simmer and frustration grows on all sides.
In my work I’ve watched versions of this dynamic destroy founding teams that should have thrived.
The really frustrating part is that most of the time, there is alignment on the big stuff.
There’s usually a shared purpose and a set of values that everyone believes in. Often there’s even agreement on the vision – where we actually want to shoot for in the bigger picture.
The breakdown seems to happen when we get to the messy questions: how do we actually get there? What needs to change? What do we do first?
That’s when the fault lines appear.
Jim Collins talks about the Stockdale Paradox in Good to Great: maintaining unwavering faith that you’ll prevail while confronting the brutal facts of your current reality.
But what happens when different leaders see different brutal facts? What happens when one sees opportunity whilst another sees risk?
This is where mediation becomes essential. Not to pick sides, but to build bridges.
In my work I’ve been building a toolbox of interventions that I use to help founding teams overcome these divides:
Creating a shared language around constraints: Helping the visionaries understand operational realities without extinguishing their ambitions. Helping the operators see possibility without their abandoning prudence. This works when both are willing to engage and listen.
Making the implicit explicit: Tensions mostly simmer over into being unhelpful when assumptions aren’t surfaced. What does “moving fast” actually mean? What does “being ready” really look like?
Focusing on sequencing, not choosing: It’s rarely either/or but too often these discussions seem to get to that point. It’s usually about what comes first and what creates the conditions for what comes next. Don’t end up in cul-de-sacs of binary choices unless you absolutely have to.
Building in regular reality checks: Monthly sessions where both camps present their perspectives on progress can help. It sounds obvious but it helps eliminate surprises and prevents festering disagreements.
Documenting decisions religiously: People are busy and forget things. Sometimes that’s wilful, but nothing breeds mistrust like forgotten agreements or remembered conversations that differ. A decision log or a simple voicenote after a meeting to capture what’s been agreed (or the outstanding points of disagreement) really helps.
The fundamental truth is that tension will always exist in leadership teams.
And that’s healthy as you want robust debate on direction, strategy and priorities. Groupthink and consensus aren’t helpful in growing businesses.
But at some point alignment becomes critical.
Without it the competing tensions between founders become the primary drag on the business.
The businesses that break through this are the ones that find a way to harness both perspectives. They can be ambitious whilst being realistic and get good at pushing forward whilst building foundations.
It’s hard work and I still find the mediation mentally exhausting but immensely rewarding. When I’m working with founders or leadership teams and get that moment where both camps suddenly see how their perspectives fit together, when the plan clicks into place and everyone’s pulling in the same direction – that’s the biggest buzz for me.
So here are three questions for you to reflect on:
- Where are the fault lines in your leadership team?
- What conversations are you avoiding because they’re too difficult?
- And perhaps more importantly… what’s the cost to your business of not having them?
best regards,
sw
From the Build archive
Build #80 –
Why we’ve got decision-making backwards
Taking a fresh perspective on how we make the big calls as businesses grow.
Build #75 –
Tension is the work: leading without easy answers
Too often they’re seen as negatives but in reality tensions are a healthy feature of every organisation.
