Connection over Transaction: How to stop wasting their time
That’s me- Sally - looking through a Side Door
The biggest Side Door lever is making a connection with another human, further along the journey than you are. But it feels so hard.
Technically, there have never been more routes to reach someone you don’t know. So, what’s the real issue here?
It could be fear of failure… but you’ve already been rejected from jobs without even speaking to a person.
I think it’s a worry about wasting someone’s time. So let’s talk about that.
The Two Traps
When you’re approaching someone you don’t know, there are two traps it’s easy to fall into:
Over-explaining
This shows as long paragraphs about who you are and why you’re interested in a particular career.
💣 Truth bomb: They don’t know you yet, so they don’t care. You’re wasting their time with your email waffle - and it’s going straight in the bin.
Hard selling
Specifically: selling yourself.
💣 Truth bomb: If they don’t have an open role (likely), they have zero interest in hearing how great you are. When you’re focused on you, you miss the chance to learn what’s important to them.
Both of these are problems of directness: the first isn’t direct enough, the second is too direct. Here’s how to get it right.
Keep it brief
Here’s a cold message format that really works:
Hi [name],
I’m a recent [subject] graduate, looking for my first role in [industry]. This month, I’m on a mission to have coffee with [number] people in the sector, to understand more about their career path and insights into how things are changing.
Your profile caught my eye on LinkedIn, because of your experience at [company] / in [role]. Given we’re both based in [area], could I buy you a coffee to learn more about your career and the industry more broadly?
Thanks for your time,
[Name]
It works because:
it’s easy to scan
there’s a clear ask, and
a low stakes way to say yes (or no).
If I agree, I know it’ll take the length of time of a coffee, I can talk about my own experience, and I’ll help you achieve your mission.
I can do good without feeling obliged to get you a job, recommend you to someone, or spend the whole day with you.
Bonus: if you discover a shared passion, or shared connection, during your research into this person - mention it! It shows you’ve done your research and most people respond well to a shared experience.
Focus on them - not you
The biggest pushback I get on this approach is this: “But I want a job. Shouldn’t I find out if they have one?”
The answer is yes… but not yet.
An estimated 70-80% of jobs are never advertised.
Often people just search their own networks to fill the gap.
Equally often, jobs are created for a person, because they show there’s a gap they can fill.
That means the best way to access those jobs - and there are a lot of them - is to become part of the network and seek opportunities to demonstrate your strengths over time.
When you’re starting out, the best route is this:
Offer something generously
This might be buying a coffee, offering a thoughtful idea about their business, delivering a creative gift… something that suggests warmth and confidence.
Build rapport
Once you’ve secured their time, honour it by being prepared. Come with a topic you really want to learn about their business, the industry, or recent trends. Not whether they have a job opening or not. Listen and respond.
Show appreciation
Thank them for their time, ideally in writing. This is rare and it makes you memorable. The thank you email is the time to recap what was valuable about the conversation - and it’s where you can make another easy ask: Would you be open to having me for work experience? Is there someone in your network I should speak to, as I consider my next steps? The worst they can say is no.
Stay in touch
Note down your new contacts and what you learned from them. That way, it makes staying in touch easy. You’ll have plenty of opportunities to email a month or so later - sharing an article that reminds you of the conversation, offering to connect them with someone else you met recently who they might like… This is also an opportunity to share your updates and let them know what you’re looking for right now.
This is not a quick process. It’s relationship-building 101 and it takes time and intention. But the results are well worth the investment.
You’ll get countless insights into different industries and career paths.
You’ll build a support group of people willing to help.
You’ll get first dibs on any jobs going - before they’re advertised.
And you’ll develop some of the most valuable professional skills there is: building and maintaining relationships.
One of the best descriptions of a job I’ve seen is that it’s just a list of problems that need to be solved.
The more you talk to someone, the more you discover what problems they’re facing - and how you might be well-placed to solve them.
Does that sound like wasting someone’s time? Absolutely not.
So next time you’re nervous about reaching out to someone new, remember this: getting to know each other might just be the best thing for both of you.
Did this resonate? Reach out to me on LinkedIn to share your stories, recommendations and questions. I love hearing from you!
