Seven Questions To Help Plan Your First Executive Sales Meeting

Steve Hall


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

If you ask yourself these seven questions they will help you make the meeting a resounding success:

1. Are you meeting the right person?

This is really 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 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.

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.

We called the CEO of Australia's largest telecommunications company, spoke to his PA and said we'd like to discuss generating 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 really cared about - and 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. And if you can't get to the final decision-makers your chances of winning a deal are significantly reduced - even if you do 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?

It's no longer enough to go into a meeting with a senior executive and say "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 and its business challenges - and how you can help them.

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, any articles they have written and so on.

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

3. What is your key objective?

It's important to know what your objectives for the meeting are - and not
to have too many.

If it's your first meeting it's too early to sell. They aren't interested in your company, your offering, your brochures, your presentations and your case studies. They are interested in themselves, their business issues and the
possibility you might be able to help them.

The objectives of a first meeting are usually:

  • To discuss the business issue you can help them solve, its implications and the impact of solving it (or failing to solve it)
  • To show you understand the issue and are an equal in this area
  • 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 (see below) 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.

4. What is their key objective?

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 in mind - so what is it?

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 the meeting.

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 to 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?

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? - to quote Dilbert).

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 all about that issue and its impact on them.

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 in the first place, you're just clarifying how they view of them.

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 like yours. 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?

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 insert 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."

7. 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.

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.

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


Like anything, implementing these ideas depends on many factors and circumstances. The main things to remember are:

  • Initial meetings are to develop credibility, not to sell
  • Make it about them first, you second
  • 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.


This article was also published in LinkedIn here. If you'd like to connect with me on LinkedIn please send me an invitation via LinkedIn here.

If you sell to senior executives, if you are a senior executive or if you help people who sell to senior executives please join my LinkedIn group, Executive Sales Coaching

Steve Hall is an executive coach and a sales coach. He helps his senior executive clients to be more productive, more focused and to have more time for the things that really matter.

And he helps sales executives to sell more and to build relationships at a higher level. 

He is a member of Sales Masterminds Australasia and this article is taken from the recent eBook published by the SMA. If you'd like a copy drop him a line.

He can be contacted on LinkedIn at onTwitter at @stevehallsydney,or by phone on 0410 481 960. He's based in Sydney, Australia.


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