What We Thought vs What We’ve Learned

Founder ReflectionsProfessional ServicesEarly-Stage ConsultingAI in Practice

4 July

Welcome to our Friday Founder Reflections, a weekly check-in from the inside of building We Lead Out. We’re a few weeks into the journey now, and this one’s a look at the gap between what we expected… and what’s actually happening. If you’re building too (or thinking about it), this one’s for you.

Spoiler: It’s not the work we expected. It’s better, messier, and way more real.

We kicked off We Lead Out with a clear view in mind. Clean strategy slides. Big-picture operating model decisions. Leading-edge AI design. The kind of work founders and execs carve out time to do because it’s smart, not urgent.

We’ve done some of that.

But what’s surprised us most is where the real traction has come from, and what clients are actually asking for.

What we thought we’d be doing

Let’s be honest. We imagined:

Strategy workshops with execs about how AI will reshape their operating model
C-suite sessions mapping out Agentforce-driven roadmaps
Senior teams calling us in to rethink how they scale smart, not just fast

There’s a version of this that’s still true. But the actual entry points? Not so neat.

What we’re actually doing

The doors are opening in much more specific, often messier places:

Helping AEs and sales teams shape first conversations in enterprise deals
Supporting proposal teams to clarify offers that feel half-built
Showing clients the real, usable version of “AI-first” in the context of Salesforce

It’s not just strategy decks. It’s craft. It’s co-writing. It’s sitting in Google Docs at 11pm, tightening language and shaping value.

And that’s been the unlock.

The reception? More human, more immediate.

When we get close to the actual work (the pitch, the presentation, the delivery), trust builds faster. There’s no need to sell transformation when you're already delivering value inside it.

Clients open up more when you’re not on a pedestal. You’re just next to them, sleeves up, helping.

What held up from the original idea?

The demand for practical AI strategy is real. People want to move, but need someone to walk it with them
The combo of delivery and design thinking still sets us apart
Our tone, helpful, smart, no fluff, is resonating

What didn’t?

No one’s asking for “agentic operating models” in those exact words
Most early-stage advisory work starts further down the org chart than we expected
Strategy is easier to earn after you’ve delivered something practical, not before

The takeaway

Assumptions are a great way to get started. But what you actually build will be shaped by how close you’re willing to get to the work.

Early-stage consulting isn’t about leading from the front. It’s about standing beside people, mid-sprint, and helping them make the next right move.

If you’re building something, or rebuilding how you deliver your work, let’s chat. We’d love to hear what’s holding and what’s shifting in your world.