booking the first meeting

The right meeting can be the event that takes your business to the next level. You gotta take a lot of them, and you often have to take the initiative yourself. Consequently, you need to approach your meeting prospect according to certain rules – depending on who they are compared to you. Use this mini-guide for determining how to approach the wooing process of the first business date.

What you have to keep in mind when you want to take a meeting with a person are the hierarchies that you both you as business person and your respective companies are in. As provocative as this may seem (tell-me-your-title-and-I-will-tell-you-your-worth and that kind of stuff) we are also aware that everybody is prioritising his time and can only take so many meetings.

To determine the relationship between you and your meeting prospect your can use our handy graph. A short introduction is in order:

You have two axis; your level in the hierarchy, which is a combination of you own role and the clout of your company, as well as your prospect’s hierarchical level.

Example: a VP of a large company can be higher in the combined hierarchy than a CEO of a small startup. Thus, you have to juggle these parameters when analysing where on the graph you arrive.

The Peer Line

As you can see on the graph, the graph gives us three possible combinations:

  • You want to meet with someone above you in the hierarchy (they are the rock star)
  • You want to meet with someone below you in the hierarchy (they are the rookie)
  • You want to meet with someone on the same level the hierarchy (you are peers)

Let’s dive into the three scenarios:


Meeting with the rock star


So you want to meet with somebody, who is above you – naturally, this is the toughest meeting to book. You know that they are in high demand, and that they are highly selective when it comes to the people that they choose to take a meeting with. You have to ‘sell’ to them that it’ll be worth their time.


Leverage your network

Many rock stars don’t respond to a meeting request from somebody they don’t know unless they have gotten an introduction from a trusted contact. Therefore you should always see if you have mutual connections and if this is the case you’ll have to ask the contact that makes the most sense – either because that person is trusted by the rock star, or because they are in a relevant industry making the introduction more business-related, rather than just a friend to another friend a favour. An obvious strategy you should keep in mind is to select a mutual contact, who perceives you as a rockstar in your respective relationship, increasing the odds that you get a killer intro. In general, introduction ensures that the rock star actually considers your request.


Explain the ‘why’

Since the rock star doesn’t know you, you need to explain briefly who you are, and why a meeting makes sense. Not to you, more importantly, why it’s relevant for them. Briefly write why your business is interesting to them, balancing between enough information to explain the main elements, and briefly enough to ensure that they in fact read the entire thing.

Just letting them know that you find them interesting and want to pick their brain is seldom enough, unless you have gotten hell of an introduction.


Make it worth their time

Rock stars are busy people, and you want to let them know that a meeting with you will not take too much of their time. At least if they don’t find meeting you that interesting after all – yes, that’s a possibility. Asking for a lunch meeting has a minimum duration of 60 minutes, potentially 45 minutes too long.

Use the word ‘quick’ when asking for the meeting. A quick coffee sounds less of a commitment and you are making it easy to say yes. Suggest the location to be their office, or the coffee bar next door to them, so their combined time is at a minimum. Remember, this is only the first date – even during the time it takes to consume a quick coffee you’ll be able to appear so interesting that you can book the second meeting much easier, and potentially take more of the rock star’s time next time.


Explain the process

We have all experienced not to get a response. And this is particularly frustrating when you genuinely want to meet the person you reach out to. Allow yourself to follow up with a phone call after 2 days with this simple trick: Write that you are going to do so. By having written it in your initial mail, you have simply made it alright to give a call, both for you and for your prospect. Anybody who has tried Tinder or one of the other dating apps knows how frustrating it is to be the one that writes two times in a row. Make sure you don’t end up in that situation in your business relations also.


Meeting with the rookie

rookie will smith

Booking a meeting with someone below you in the hierarchy is much more straightforward than the other way around – remember, now you are actually the rock star!

Of the different means of communication you have it’s still the email as the obvious choice – unless it’s urgent, in which case you’d just pick up your phone and call.


Just reach out

The introduction is less important in this scenario, since an inherent part of being the rock star entails that they know that they are the rookie. If this is not the case you may have analysed the relationship wrong, and you should consider one of the other three scenarios in this article.

But if you are in fact the rock star, your prospect will already have an idea about who you are, or what your company does, and they will be flattered that you reach out to them. In the platonic rock star/rookie relationship they will know that you possess great potential value, and a positive response to your meeting request should not be difficult to get.


The meeting terms

Depending on the degree to which you are a rock star (how much above in the hierarchy are you) you can dictate the terms of the meeting. Are they invited to come to your office? Should you meet on neutral ground? Do you go to their place? This is a case by case assessment that you have to make.

You don’t need to be as explicit about taking a short and efficient meeting, but keep in mind that nobody wants to waste their time, so emphasise that you’re interested in getting to know the other part (or whatever your objective of the meeting), then they also know what your agenda is.


Meeting with the peer

peers bill gates steve jobs

Getting meetings with your peers require that you both perceive yourself as peers. Not surprisingly this scenario is located between the two aforementioned, albeit closer to when a rock star wants to take a meeting with a rookie than the other. The reason being that the prospect’s perceived value of for the meeting is bigger, thus the yes is easier obtained.


Give the brief pitch

Just like approaching some attractive individual at the bar, the favour will inherently be in the hands of the ‘approached’, rather than with the ‘approacher’. You show the first piece of interest, which translates into power to the other one.

Consequently, you still need to briefly explain why you think you should take a meeting. And who you are. But since you are peers you will most likely have many things in common, which both of you acknowledge. Definitely a reason why these meetings are not difficult to get in your calendar, and quite contrary to the hit single ‘When you wasn’t famous’ by The Streets, which revolves around the concept of not being able to pick up famous girls as easily as not famous girls, when you are famous yourself. Luckily the business environment doesn’t face these tragic obstacles.


Social media

When making the first moves with your peers, feel free to exploit LinkedIn, the playground and display window of today’s ambitious and self conscious professionals. Your meeting prospect will quickly be able to scan your profile (title and company, remember), and their internal compass quickly settles on either a positive response, or totally ignoring you. Keep in mind that LinkedIn usage (and potential over-usage) varies as you maneuver in the hierarchical levels. People who are located high in the hierarchy tend to get a lot of LinkedIn messages, and your request could drown. People who are low in the hierarchy (or who just don’t use it much – a quick glance on the number of connections gives a good indication) may not reply in time soon.



As with all meeting requests, show good manners, and let the meeting be on your prospect’s terms. Alternatively, invite him over for a get-to-know-you-over-coffee meeting, but let him make that decision.