The conversation
We’d been talking for a while. Really good business, making money, decent team, but stuck. Running hard and going nowhere. Every day felt like wading through treacle, and the frustration of not being able to see a way out was written all over him.
Then, almost as an aside. Not a grand revelation, more like something he’d been carrying for a while and finally put into words:
“What I really need is a number two.”
He already knew. I already knew. He just didn’t know that’s what it was called, or that it existed as something you could actually go and get.
Every decision was still going through him, when all he really wanted to do was get out there and grow the business, not be stuck in it.
I’ve heard this before
Not from a client. From my father.
In 2007, he called me with a version of the same problem. He’d started RWA, a solid associate-led compliance consultancy serving insurance brokers, from the ground up. Good business, good clients, but his attention was needed elsewhere, and he could see it wasn’t going to grow beyond a certain point without someone alongside him who could see what he couldn’t.
He didn’t frame it as needing a number two. He framed it as needing someone to build an e-learning platform. To take a great entrepreneurial idea and turn it into a new innovative product. But that’s exactly what it was. He needed complementary capability. Someone whose strengths balanced his. Someone who could carry the commercial and operational weight while he focused on what he did best.
So I joined. And what followed was thirteen years of building something neither of us could have built alone, taking the business from a small boutique consultancy into a market leader.
The platform was almost incidental. What actually drove the growth was the dynamic. Two people, different skills, same direction, supported by a great team, each one making the other more effective.
When I stepped up into the leader role at RWA, I myself benefited from having several number twos beside me. All with different skills, people I could trust to deliver, tell me the hard truths, and who would free me up to work on the business without getting stuck in it.
Why founders end up here
The treacle feeling isn’t a sign of failure. It’s almost always a sign of success.
You built something that works. Clients value what you do, the business is making money, but somewhere along the way, gradually and invisibly, the business outgrew the solo decision-maker at the centre of it. And because it happened slowly, you didn’t notice until you were exhausted and going nowhere.
Every decision still lands on your desk. Every problem still needs you in the room. Every direction change still requires you to carry it. And the harder you work, the more the ceiling stays exactly where it is.
That’s not a motivation problem. It’s not a strategy problem. It’s a structural one. The business needs something you can’t provide alone, not because you’re not good enough, but because no single person can be excellent across every dimension a growing business requires.
Getting there is a great achievement. But staying there too long can be exhausting.
What a number two actually does
It’s not a junior, or a founders’ associate who executes your instructions. It’s not a consultant who writes a report and disappears.
- Someone who thinks alongside you.
- Someone who sees what you can’t see because they’re not inside it the same way you are.
- Someone who challenges your thinking, not to undermine it, but because unchallenged thinking is how good businesses make bad decisions.
- Someone who carries the commercial function: the systems, the positioning, the pipeline thinking, so you can get back to what you’re actually good at.
The merger I worked on later in my career was the same model in a different context. The MD brought technical excellence, a team who had her back, and a huge amount of client trust. I brought commercial operations, integration, and cultural alignment. We clicked immediately, not because we were technically similar, but because we weren’t. Complementary strengths, a shared direction, and neither of us trying to do the other’s job.
People couldn’t believe we’d been each other’s biggest competitors for the preceding ten years. It didn’t matter, because we both wanted the best outcomes for our common stakeholders. That’s what the number two model looks like in practice. Win-win.
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The path forward
He knew before he said it. Most founders do.
The question isn’t whether you need a number two. If you’re wading through treacle and can’t see the ceiling you’re hitting, you almost certainly do.
The question is: what are you going to do about it?
If this resonates, I’d be happy to have a straight-talking conversation. No agenda, just an hour to work out what’s actually going on and whether there’s a path through it.
Sometimes that’s enough on its own. Just knowing that what you’re feeling isn’t unique to you, that every founder at this stage feels it, can be the thing that lets you breathe again. Sometimes I can point you in the right direction, or signpost you to someone better placed to help. And sometimes we’re a good fit to work together.
But it starts with a conversation. My door is open.
If you want to assess your own commercial situation, I now have 4 free diagnostic tools to help every founder. Try them out here: https://addoli.com/diagnostics
