Seven questions to help you plan your first executive meeting

You’ve finally scheduled that meeting you’ve been trying to get with a high level executive in one of your biggest target accounts.

You know first impressions are critical and you want to make sure you get it right and don’t fall at the first hurdle.

Ask yourself these seven questions to help make the meeting a resounding success:

1. Are you meeting the right person?

Source — Giphy

This is a question you should be asking before you schedule the meeting. If it’s your first meeting in the account you should be aiming for the highest level executive you can reach — assuming the solution you’re selling affects them.

The best way to do that is to define your business value proposition for that specific company and, depending on the company you’re targeting, approach the CEO or other senior executive.

Tell them you’d like to discuss how you can help them to achieve a specific business goal that they really care about. If they do really care about it they will either see you or refer you to the person who has responsibility for that area.


A very small South African software developer was trying to get in to Australian telcos to discuss their complex billing software. They had no offices, customers or staff in Australia. They didn’t even have a web site

But if we had approached the IT Department, the CIO or procurement they would have been knocked out of the ballpark on day one due to their lack of presence in Australia.

After discussing their solution we decided they had the capability to allow large telcos to generate new revenue streams from their customers by offering more flexible pricing.

So we called the CEO of Australia’s largest telecommunications company, spoke to his PA and said we’d like to discuss helping to generate new revenue streams for them. We were referred to his second in command who in turn organised meetings with several Executive General Managers and the CTO — purely because we’d identified a business issue that they cared about that our client could help them with.

It’s critical to enter a major account at the right level. If you start at the top and you’re referred down, you go to a meeting with the imprimatur of the person who referred you.

If you enter via the bowels of the ICT department or through a middle manager it can be difficult, if not impossible, to climb to the level of the people who make the final buying decision. If you can’t get to the final decision-makers your chances of winning a deal are significantly reduced — and even if you finally reach them you’re seen as someone who operates on a lower level rather than a valued business partner.

For the purpose of this article, let’s assume you’re meeting with someone at the right level to discuss helping them with a business issue they care about.

2. What do you know about the company and person you’re meeting?

Source — Giphy

It’s no longer enough to go into a meeting with a senior executive and ask “tell me about your business” or “what keeps you awake at night?” Senior executives expect you to have done your research before they meet you.

You need to understand what the company does, who its key customers are, its offerings, its history, sales challenges and its business challenges.

You also need to know as much about the person you’re meeting as possible — what other positions they have held, what they care about in their current role and so on.

By doing effective research using the company web site, annual report, newspaper articles, industry research, LinkedIn profiles and articles the executive has published you should be able to get a good picture of the company and executive you’re meeting with.

3. What is your key objective?

Source — Giphy

It’s important to know what your objectives for the meeting are — and not to have too many. One is ideal.

If it’s your first meeting it’s too early to sell. They aren’t interested in your company, your offering, your brochures, presentations and case studies.

They are interested in themselves and their business issues and the possibility you might be able to help them.

It varies depending on the circumstances, but usually the objectives of a first meeting are:

  • To discuss the business issue you can help them solve, its implications and consequences
  • To show you understand the issue
  • To develop credibility as a person and an organisation that can help them
  • To agree there’s potential for you to help them
  • To agree on the next step

The first meeting should be almost all about them and very little about you. You should encourage them to do the talking by asking intelligent questions then listening to (and taking notes of) the answers.

You shouldn’t take presentations, brochures and other marketing aids to the meeting and under no circumstances should you even consider demonstrations during a first exploratory meeting.

My strong recommendation is that the only props you should take to a first meeting are your brain, your research and either a pen and paper or a laptop/table for taking notes. Personally I prefer a pen and paper — it removes the temptation to use the laptop and looks more elegant (and confident) when you walk in unarmed with technology.

Oh, and this may seem bleeding obvious, but TURN YOUR MOBILE OFF.

4. What is their key objective?

Source — wiseGEEK

You know what you want from the meeting. But what do they want?

Senior executives are very busy and they have many demands on their time. They rarely meet anyone without a specific objective — so what’s their specific objective for their meeting with you?

You should be able to make an intelligent assumption about their objective based on the reason they accepted the meeting and what was said to get them to agree to it.

However, the best way to validate your assumption is — to ask them. Two questions you can ask are;

I know you’re very busy — what was your motivation in accepting this meeting?” or “What objective do you want to get out of this meeting?”

Then make sure you address those objectives as a priority — and at the end of the meeting ask them if you’ve done so to their satisfaction.

5. What intelligent questions can you ask?

Source — Giphy

The quality of the questions you ask will determine how they view you.

The statement “there’s no such thing as a stupid question” is in fact a stupid statement (if there’s no such thing as stupid question, what sorts of questions do stupid people ask?).

Generic questions such as “Tell me about your business” or “What are the top three business issues you’re facing?” simply show you haven’t done your research. If you’re talking to an important target account and you believe you can help them with a key business issue you need to know a lot about that issue, its effects and how to fix it.

By asking intelligent questions you not only get the detailed responses that allow you to understand more but you show that you understand their issues.

If you’re meeting to discuss a specific business issue then the questions should be related to that issue and should demonstrate your familiarity with the issues and its impact.


I know you recently bought another company. In our experience there are many logistical and cultural issues when you’re trying to integrate two companies. How are you handling the issue of merging your sales teams?”

That shows you know about them, it shows you know about the kinds of issues they face and it gets more information on the area you’re interested in (assuming you’re interested in helping people with their sales processes).

6. What questions are they likely to ask?

Source — Giphy

At some stage, they are going to ask you a question. The better you’ve prepared the better your answer will be and the more professional you’ll look.

Ask yourself: “What questions are they likely to ask and how will I respond?” — remembering you want them to do most of the talking. So prepare answers that are accurate, honest — and ideally fairly short.

If they ask: “What do you do?” resist the temptation to launch into your company or product pitch. They don’t really want to know what you do. They want to know what you can do for them. The correct answer is: “We help companies like you to <solve the business problem you’re there to discuss>”.

And if they ask a question you can’t answer, rather than prevaricating it’s best to say: “I don’t know but I’ll find out.”

What is the next step?

You should have a next step clearly in mind. It may be to get a referral to another executive, it may be to organise an investigation, arrange a presentation or schedule a demonstration.

(In fact I prefer to leave demonstrations until much later and avoid them altogether if possible. In my mind demonstrations often cause people to focus on the minute rather than look at the big picture. If you’re trying to sell and ERP you don’t want people obsessing over the colour of the screen or the number of digits in the part number field)..

Whatever it is, know where you want to go, understand where they want to go and agree on the next step at the end of the meeting.

Once the meeting is over you should send the executive a summary of what you discussed, what you agreed and what the next step is.

Tell them it’s your recollection of what was said and could they check it and make sure you didn’t miss anything.

Use what they told you in their own words as much as possible. This a) makes you listen carefully; b) makes you take detailed notes, which stops you talking too much; c) impresses them with how much you listened and understood; and d) gets their agreement on what was said, or clarification if you got things wrong.


Like anything, implementing these ideas depends on many factors and circumstances. The key issues are:

  • Initial meetings are to develop credibility and learn, not to sell
  • Make it about them first, them second, you third
  • Listen as much as possible. Talk as little as possible
  • Understand what they are trying to achieve
  • Understand them and their business issues
  • If you’ve gone to a lot of trouble to get a meeting at the right level, you need to prepare and research thoroughly
  • Your objective isn’t to qualify an opportunity — this should be a by-product of the meeting, not the rationale for having it
  • Know where you want to go and where they want to go after the meeting
  • Prepare, think then prepare again
Source — Giphy


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