Cold outreach: what actually works in 2026 (and what doesn't)

This is the fifth in my series on five ways to find clients, and it’s about the one most people think of first: cold outreach. I ran it properly, for five businesses, to find out whether it works. Here’s the honest answer.

For the past few months I did something I’d never done before. I ran outreach on behalf of five businesses inside IMMA. By now, over two thousand people.

Here is what I learned.

The five businesses joined a pilot with one promise: aligned clients, more consistently. An end to the feast-and-famine cycle most independents know too well, where you’re either buried in delivery or staring at an empty pipeline.

One thing became obvious fast.

Reaching out as a collective changes that. You arrive not as one narrow service, but as access to a trusted circle of senior people who can solve whatever the problem turns out to be.

Here’s the thing I wish someone had told me when I first started working for myself.

When you reach out to potential clients, only a small fraction are ready to buy now. Research from the Ehrenberg-Bass Institute puts it bluntly: at any moment, roughly 95% of potential buyers are out of market. Only about 5% are actively looking.

The other 95% aren’t uninterested. They aren’t ready yet.
They may become clients over the next six, twelve, eighteen months, when their budget turns over, when a leadership change happens, when the timing lines up. In trust-based work especially, people buy when the moment is right, not when they first come across you.

So if you reach out once and hear nothing back, the most likely reason isn’t that your message was weak, or that you’re bad at this. It’s that you reached ninety-five people out of a hundred at the wrong moment. Single outreach isn’t failed outreach. It’s mistimed outreach.

Which means the whole game is staying in touch over time without it consuming you. Daniel Priestley’s well-known rule of thumb is that people need around seven hours of cumulative contact before they trust a business enough to buy from it. You don’t reach seven hours with one cold message.

This is why we built the things I wrote about earlier in this series. The opportunities roundup. The funding digest for organisations. A reason to stay in touch every month that’s useful, rather than another “just checking in.”
That groundwork isn’t a nice extra. It’s the only thing that makes outreach pay off over the timeline it actually takes.

I have a love-hate relationship with this experiment.

I was, in a way, forced into it. I’d made the promise to the five businesses, and keeping it pushed me right to the edge of what I can carry. It became the most time-intensive thing we have ever done at IMMA Collective. I brought in help, from people and from tools, to keep it moving. And before we could even reach out properly, we had to build all those lead magnets first, so each person had something to give rather than ask for. That alone took weeks.

So here is the first honest thing. I won’t run it in this format again. Measured against what the members paid for the pilot and the hours it has taken me, the maths doesn’t work. Not even close. I’ll finish it for this cohort because I made a promise I want to keep. But running outreach for people, one by one, is not something I’d take on again.

And here is the second, which took me longer to admit. I took too much responsibility over the result. I put enormous pressure on myself to make this “absolutely successful” in the obvious way. Signed contracts, visible wins, a tidy ROI story by a date I had set. That date was mine, not the market’s.

Experiments take time to run, and longer to read. Some bombed. Others are performing well. What I can already see is that the messages land and people reply. What won’t bend to my will is the clock, and no amount of effort on my side compresses that.

What the pilot did do was force me to be more creative, more resourceful, more adaptive than I have ever been in this business. Adjusting what we sent. Rebuilding lists. Reframing offers. Learning from each batch and changing course faster than I thought possible.

That’s the thing I’m proudest of. Not the contracts. The resilience. The proof, again, that what I can rely on isn’t a plan working perfectly. It’s my ability to keep figuring it out when it doesn’t.

It’s working. Just not in the shape I imagined. In a stronger one.

And I have to be honest about timing. We’re only a couple of months in, and the effect of this kind of work shows up late. I don’t yet know how it will pay off, and it might not pay off while these particular people are still in the pilot. That’s the uncomfortable truth about relationship-building. You plant now and harvest much later, sometimes after the season you planted in has ended.

What I can see, even halfway through, is where the value gathers. Less in the cold messages. More in the relationships between the people already here.

Last week someone in the collective sent me a small message. She’d noticed members mentioning her, recommending her, when they came across something that fit her work. She was delighted. She hadn’t pitched anyone. Her name got tagged in places she wasn’t in.

That is the thing. If I had to build the whole of IMMA around one idea, it would be that one. Not getting better at cold outreach. Becoming the kind of person others think of, and say out loud, when the right moment lands in front of them.

The small cross-pollination gatherings we run, which are not networking events but rooms where people get to know each other’s work, built more of that than two thousand cold connections did.

In a world where AI can personalise outreach endlessly, every inbox fills with plausible, tailored, slightly hollow messages. What gets through that isn’t a cleverer cold email. It’s a person who already trusts you, or trusts someone who trusts you.

As AI floods every channel, the future of finding work is relational. The cold outreach experiment taught me that by showing me its edges.

There’s a more uncomfortable truth in here, and it’s worth saying.

For some of the people we reached out for, there are fewer opportunities than a year ago, because AI is absorbing parts of what they used to be hired to do. You feel that fast when you’re doing outreach. Some offers need reframing to stay attractive. The organisations that used to want a service delivered now want to know how to use AI to do it themselves, or how to do it differently.

Almost all of us need to rethink what we’re offering right now. And the only way to discover what’s still relevant is to be in conversation. The payoff of outreach often isn’t the sale. It’s the market insight, the signal about what people actually need now, which you only get by talking to them.

Pick one person you’d love to work with. Someone who isn’t ready to buy now, and might not be for a year.

Don’t pitch them. Do one small, useful thing with no ask attached. Send a funding opportunity that fits them. Share something relevant to a problem they’re wrestling with. Make an introduction that helps them.

Then put a note in your calendar to do it again next month. A different useful thing. Still no ask.

That’s how you turn one cold contact into the start of a warm, slow relationship. The kind that’s there when the 5% moment arrives. Do it with five people and you’ve built more pipeline than most cold campaigns ever manage.

This was the fifth of five ways to find clients in this series. (Earlier: 1. intro, 2. referrals, 3. opportunities, 4. peer promotion aka. getting clients without talking about yourself.)

Next week is the last one, and it’s different. It’s the system we’re building right now, together. The one I’m most excited about. And the most honest look yet at where IMMA is going.

Take care,
Lilli

P. S. That room, where your name comes up when you're not in it, is what IMMA is for. A circle of senior people who get to know your work well enough to think of you, and say your name, when the right opportunity appears. We've opened the waitlist, twenty new members joining in June. If you'd like your next aligned opportunity to find you through a relationship rather than a cold message, add your name to the waitlist.