I recently received a message congratulating me on growing Big Reputation while also leading my US softball team to success.
Which was flattering, except for one fairly important detail. I have never led a US softball team.
I am Chelsea Spencer, Founder and Managing Director of Big Reputation, a UK marketing agency. I am not Chelsea Spencer, the American former professional softball player and coach. Somewhere along the way, an outreach tool had clearly pulled information from both of us, blended it together and sent me a message as though I’d been spending my time balancing client strategy with elite American sport.
It was funny, but it was also a perfect example of why so much outreach falls flat. The business sending the message had tried to personalise it, but instead of making me feel understood, it made it obvious that nobody had properly checked who they were contacting. A message that was probably intended to feel relevant and thoughtful ended up feeling lazy.
That is the problem with a lot of outreach now. It has never been easier to send, so more people are sending more messages with less thought behind them. Decision-makers are being hit with cold emails, LinkedIn messages, connection requests, sales pitches, automated follow-ups and “just circling back” messages every single week. Some are polite enough, some are painfully pushy and some are so obviously automated that you can almost hear the CRM running in the background.
The uncomfortable truth is that most outreach doesn’t fail because the offer is terrible. It fails because the message gives the person receiving it no real reason to care. It might be technically personalised, but it doesn’t feel considered. It might mention a name, a company or a recent achievement, but if the context is wrong or the message still feels generic, the trust disappears before the conversation has even started.
We trialled it ourselves and got exactly what we expected
Recently, I decided to test this kind of outreach again at Big Reputation as I’d done nothing like this since my early days in sales. Before you say anything, I didn’t know any better at 21!
I receive so many cold messages myself and I never reply to them. Most of them feel like they’ve been sent with very little thought behind them and even when the service could be relevant, the message itself gives me no real reason to engage.
So, partly out of curiosity, we decided to run a small trial. The thinking was essentially, “We get so many of these messages, we don’t reply to them, so let’s see what happens if we send some from my EA and test whether anyone responds.”
We weren’t expecting much and that’s exactly what happened. We received absolutely no replies.
That result didn’t surprise me, but it did confirm something important… The problem isn’t always that the audience is wrong or that there’s no potential opportunity there. Sometimes the channel has simply become so saturated with generic outreach that people have trained themselves to ignore it. If the message doesn’t feel highly relevant, genuinely considered or worth their time, it gets deleted, archived or left unread with everything else.
That’s why we’re now trialling a very different approach through highly personalised, handwritten physical outreach. Instead of trying to reach more people with less effort, we’re choosing fewer people and putting more thought into each interaction. The aim is to make the recipient feel like they have genuinely been chosen because there is a real reason we would like to start a conversation with them. I’ll keep you updated on how that approach works for us.
But for now, here’s my thoughts on outreach as a sales person / marketeer.
Bad personalisation is worse than no personalisation
There is a lot of pressure now to personalise outreach. People are told to use the recipient’s name, mention their company, reference a recent post, pull something from their website and prove they’ve done their research. In theory, that all makes sense. Nobody wants to receive a message that feels like it could have been sent to anyone, in any sector, at any level, in any business.
The issue is that personalisation only works when it is accurate, relevant and connected to the reason for getting in touch. When it is wrong, it does the opposite of what it was supposed to do.
If you congratulate someone on an achievement that belongs to someone else, reference a project they had nothing to do with or pull in a random fact that has no bearing on their business, you look careless. It shows you’ve relied on a tool to do the research, skipped the human judgement and hoped the recipient wouldn’t notice.
That’s where badly used AI and automation become risky. The technology might be able to gather information quickly, but it doesn’t always understand context. It doesn’t always know whether the person it has found is the right one or know whether the detail it has pulled is current, accurate or relevant. If nobody checks it properly before pressing send, the mistake becomes part of the first impression.
And first impressions matter, especially in B2B. Your outreach is often one of the earliest experiences someone has with your brand. Before they have spoken to you, seen your proposal or understood your service properly, they have already formed an opinion based on the way you approached them.
Personalisation and consideration are not the same thing
There is a difference between personalising a message and making someone feel like the message was actually meant for them.
Personalisation is using someone’s name, mentioning their company or referencing something they have posted online. Consideration is understanding why the conversation would matter to them in the first place.
A lot of outreach gets this wrong because it tries to sound personal on the surface, while the actual message underneath is still generic. It opens with a line that looks like research, then quickly turns into the same pitch that has been sent to hundreds of other people. The recipient can usually feel that straight away.
Good outreach doesn’t need to prove you’ve spent twenty minutes scrolling through someone’s LinkedIn profile. It needs to show that you understand something commercially relevant about their world. That might be the sector they operate in, the pressure their role carries, the stage their business is at, the type of growth they are trying to achieve or the problem they are likely to recognise.
Relevance isn’t adding a personal detail for the sake of it, it’s making the person feel that there is a genuine reason you have chosen to contact them.
Too many businesses are speaking to a list, not a person
People can tell when they have been added to a database, dropped into a sequence and sent a message that could have gone to 500 other people before lunch. Even when the message includes their name or company, there is a particular emptiness to outreach that has no real thought behind it.
That doesn’t mean every message has to be written from scratch. There’s nothing wrong with having templates, systems and processes, particularly if outreach is a serious part of your business development strategy. In fact, a good outreach process should have structure because consistency matters.
The problem starts when the process removes too much of the human thinking. A template should help you communicate clearly, not make every recipient feel interchangeable. A system should make outreach more efficient, not strip out the judgement that makes the message worth reading.
A strong outreach message should make the recipient feel like there is a reason they have been chosen specifically. It should show that you understand something about their business, their sector, their role or the challenge they are likely to be facing. It needs to feel as though there was a person involved before the message landed in their inbox – which leads me onto…
Attention is not the same as trust
The worst outreach mistakes usually happen when businesses become obsessed with getting attention at any cost. They focus on the open rate, the reply rate or the hook, without thinking enough about how the message makes the recipient feel once they realise why they’ve been contacted.
There was the recent example of a US tech consultancy that reportedly sent a cold email with the subject line “Saw your name in the Epstein Files”. It was called out publicly by a Manchester founder, criticised online and the company later issued an apology. It might have achieved the first objective of outreach, which is getting someone’s attention, but it did so in a way that damaged trust immediately. That is the danger with treating outreach like a game of open rates. Attention is not the same as credibility and if your subject line makes someone feel misled, disgusted or manipulated, it doesn’t matter how clever you thought it was. You may have earned the open, but you’ve lost the person.
That is where a lot of sales advice goes wrong. People are told to “pattern interrupt”, “stand out” or “cut through the noise”, but there has to be a line between being noticeable and being reckless. In B2B, you are trying to start a relationship that involves trust, judgement and professional confidence. If the first impression you create is that you’re willing to use shock, fear or misleading references to get attention, you have told the recipient something about your standards before you’ve even explained what you do.
The message is usually too focused on the seller
On a slightly less dramatic note, one of the most common reasons outreach fails is that it starts in the wrong place. Businesses often lead with who they are, what they do and how good their service is, assuming that if they explain the offer clearly enough, the person reading it will want to know more.
The problem is that the person receiving the message is not sitting there waiting to learn about your service list, they are thinking about their own priorities. They are thinking about targets, margins, workload, growth plans, internal pressure, customer expectations, retention, recruitment, delivery problems or the fact their current approach is no longer working as well as it used to.
This is why so many messages can be technically accurate and still completely ineffective. They explain the service, but they don’t create any commercial relevance. There is a huge difference between saying you offer marketing support and showing a business owner that they may have outgrown inconsistent content, reactive campaigns and relying too heavily on referrals.
One describes what you sell. The other names a problem they might already feel.
That distinction matters because people are more likely to respond when they feel understood. They need to see themselves in the message, recognise the issue you are describing and understand why speaking to you could help them move forward.
Weak follow-ups make the original message worse
Following up is an important part of outreach, but a poor follow-up can make the whole approach feel even less considered. Most people have received messages that say “just checking in”, “bumping this to the top of your inbox”, “did you see my last message?” or “any thoughts?” without adding anything new to the conversation.
The problem with these follow-ups is that they ask for attention without giving the person a stronger reason to respond. They don’t add context, they don’t make the case clearer and they don’t show any deeper understanding of the person’s situation. They simply chase.
Chasing is not the same as building a reason to reply.
A better follow-up should move the conversation forward, even if the person hasn’t responded yet. It might share a useful observation, reference a common challenge in their sector, clarify the commercial reason for the conversation or offer a more specific angle that makes the message easier to understand.
The aim should never be to wear someone down until they finally give in. The aim is to make the potential value of the conversation clearer each time you make contact.
Your brand needs to support your outreach
Outreach doesn’t happen in isolation. Before someone replies, there is a good chance they will look you up. They might visit your website, check your LinkedIn profile, look at your company page, read your content, review your case studies or glance at the people behind the business.
This is where a lot of outreach quietly falls apart.
You might have sent a reasonably strong message, but if the rest of your brand doesn’t back it up, trust starts to fade. If your website is vague, your LinkedIn presence is inconsistent, your content doesn’t show a clear understanding of their world and your case studies don’t support the type of results you are talking about, you are asking one outreach message to carry too much weight.
People want reassurance before they respond, particularly in B2B where decisions are considered and budgets need to be justified. They want to feel confident that you understand their sector, that you have done this kind of work before and that giving you their time won’t be a waste.
That confidence is built through the wider brand experience, not through one message alone.
More outreach will not fix a weak approach
If your outreach isn’t working, the answer is not to send more messages. The smarter move is to pause and look properly at the foundations.
- Are you clear on who you want to work with?
- Are you contacting the right people?
- Does your message connect to something they genuinely care about?
- Is your personalisation accurate and relevant?
- Does your follow-up add value?
- Does your wider brand presence support the promise you are making?
If those things are not in place, increasing the volume will only get a weak message ignored by more people.
Strong outreach should feel focused, relevant and considered. It should show that you understand the person you are speaking to, the sector they operate in and the reason your business could be useful to them. It doesn’t need to be overcomplicated, full of gimmicks or written as though you are best friends with someone you have never met.
It does need to feel like there was thought behind it though.
People can feel the difference between being prospected and being understood, and that difference is often the reason they reply.
If you’re struggling with generating leads online, we can help with your marketing conversation strategy.