5 Conversations I’ve Had With Headteachers That Will Help You

by | 20 Nov 23

Back in the good old days of the early 2000s when I was just starting out in the world of schools and technology. I was working for a council and, back then, getting a headteacher’s ear wasn’t quite the Herculean task it is today. Even when I took the plunge and launched my first EdTech venture in 2005, headteachers were pretty easy to get a conversation with.

But how things have changed! Today, reaching out to the right person in a school feels like trying to find an actual Unicorn 🦄. And believe me, that’s true even if they’re using and appreciating your product or service. It’s tough!

I’ve written a blog with my thoughts on this before, shared my opinions, and offered tips and tricks that helped me navigate these choppy waters. These techniques aren’t just theories, they’ve been tried and tested by teams I’ve worked in over the years. But recently, I found myself wondering – what could be useful for folks in Education Services and EdTech businesses? How could I share insights that might help you reposition yourself as someone a headteacher would want to sit down with?

So, I did what any curious mind would do. I got on the phone with a headteacher friend of mine (hats off to him for the brilliant idea!) and decided to have 5 heart-to-heart conversations with headteachers, asking them straight up – what could sales and customer success people do to help ‘cut through the noise’? What could make them stand out from the crowd and increase their chances of getting a meeting with you?
From these chats, I got three main takeaways. I’m excited to share with you in this blog.

Here goes…

Table of Contents

Use these links to jump straight to the part of the article that interests you most.

> “Give Me Relevant Information”
> “Make Me Trust You”
> “If I Don’t Know You, Do Your Research”
> Three Other Points

“Give Me Relevant Information”

Let’s start with the first conversation I had.

Here’s what happened. This headteacher confessed that she usually ignores emails or social media messages from vendors. But, there were a few times when she actually sat down and read the messages. When I probed a bit about why those messages caught her eye, she spilled the beans. It was because those messages weren’t just trying to shove a product on her. Instead, they showed a genuine interest in understanding how they could help schools improve.

In fact, this conversation sparked an idea for a different blog where I zeroed in on this very point. I took one of the not-so-great emails she received and gave it a makeover into something she agreed was much more likely to make her stop and read.

This notion aligns perfectly with a study I came across on ResearchGate. The study suggests that successful salespeople are often more like detectives, gathering info about their customers’ needs and then tailoring their approach accordingly. And that can be a big thing if you need headteachers to sit up and take notice you.

Now this headteacher was the only one who mentioned this point. Just because it was brought up by only one person doesn’t make it any less significant – at least not to me. I think this is crucial! And after chatting with the other four headteachers, I thought I’d throw this point their way to get their reactions. And, none of them had considered it before, but they all agreed it would definitely help grab their attention.

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“Make Me Trust You”

From the five chats I had, all five headteachers alluded to this one. They all said that they’re much more open to taking a call or meeting with someone they’ve heard of before. Not necessarily someone they know (although that also helps, obviously), but someone they’ve heard of.

When this was brought up I asked, “Where do you ‘get to know’ these people?” One mentioned local meetings and trade shows like BETT. But – they all mentioned Twitter (or X)! Yes, every one of them.

Now, if you follow my posts on LinkedIn and X, you’ll know I’m quite intrigued by the use of social platforms. So, naturally, this piqued my interest.

All five headteachers were active on X. They all admitted they’d be more inclined to take a meeting with someone they “recognised from Twitter”. Four of them even added, “… and I like what they post” or “… and I’m involved in the same conversations on there.”

As for LinkedIn – well, four out of five said they would take a meeting from someone they knew from there. One of the headteachers wasn’t on LinkedIn.

And Facebook? They all said they’re part of one or more ‘headteacher groups’, but ruled out any salespeople approaching them there – those are private groups.

So, what’s the summary? If you want a headteacher to take a meeting with you, get yourself known on social media. Get involved in the conversation. It’s as simple as that!

“If I Don’t Know You, Do Your Research”

Now, here’s something that caught me off guard. When I asked the question, “Have you ever had a meeting with a company purely from their out-of-the-blue email campaigns?”, I was expecting a resounding “No way!” or something along those lines from all five. But I was in for a surprise! Two of them actually said they’ve arranged meetings as a result of cold email outreach.

Before you get too excited, let me tell you – this doesn’t happen often. One of these two headteachers last had such a meeting booked pre-COVID, while the other recalled one from this academic year. Despite their inboxes being flooded with hundreds of emails that typically end up in the bin, every now and then, an email manages to stand out and grab their attention.

So, what’s the secret for these emails that get a meeting? Well, from my chats, I gathered a few common factors:

  • “Persistence is key.” Don’t just send one email and call it a day. You need to follow up, and you need to do it multiple times.
  • “Keep it simple.” Plain text works best.
  • “Make it personal.” This is the real deal-breaker (see below).

Now, when I say ‘personal’, I don’t mean just plugging in their name or school’s name. It goes way beyond that. Addressing the headteacher by their correct name is a must. As one headteacher put it, “I get tons of emails addressed to the previous head. I never read them. If they can’t be bothered to do their homework, how can I trust them to deliver a great service?”

But the personal touch that really makes a difference is when you mention something highly relevant to their school.

Perhaps it’s about their recent KS2 results, something from their latest Ofsted report, or a news item that directly impacts them. The bottom line is, you need to show in your very first paragraph that you’ve done your homework and you understand their school.

That’s how you turn a cold email campaign into a warm conversation.

As I’ve mentioned before, I’m not keen (at all) on cold email and cold call strategies. But, I guess, if you’re going to do them, at least do them well. And hopefully, the insights from these headteachers will help you.

Three Other Points

Alright, so to finish off, here are a few other points that were brought up in these five conversations. Now, they did say that these were nice-to-haves, not necessarily must-haves. Or, it was just one headteacher who mentioned it. But I thought I’d include these because every insight is valuable I reckon.

  1. “Be Transparent and Honest.” If your product can’t do something, own up to it. I totally agree with this. But I think this is a bit of advice that only applies once you’ve already had the face-time with the headteacher. Nonetheless, it’s something you should do.
  2. “Communicate Regularly.” This one’s mostly about email campaigns. Graphically designed emails may not end up in the bin, but they don’t exactly get you a meeting either. Two headteachers did say though, that these types of emails at least keep the brand on their radar. The other three? They didn’t touch on this at all.
  3. “Ask for Feedback.” This one’s got an interesting twist. One head said they’d be open to a sales demo meeting with a company they’re already doing business with. They’d simply say “yes” to see what the new update or product is all about. But here’s the catch – this would only work if the business is known to actively seek feedback from their customers and actually do something about it.

Well, that’s all! I hope this round-up of my conversations offers some fresh insights into how you can rise above the noise. Give these tips a shot. According to these five headteachers, they could significantly boost your chances of securing a meeting.

Now, here’s a funny thing – when I offered an option to be named in this blog or not, each headteacher took the option to not be named or even have their school mentioned.

They thought it would add to the avalanche of phone calls and emails they receive every week! It just goes to show – they’re not looking for more communication, they’re looking for better communication.

Something to think about!

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