8 Questions That Entrepreneurs Should Ask in a Pitch Meeting

Pitching a new client or investor can be one of the most rewarding and nerve-wracking aspects of being an entrepreneur. When a pitch is going well and you're humming on all cylinders, it can be incredibly energizing and give you renewed faith in your abilities and ideas.
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Pitching a new client or investor can be one of the most rewarding and nerve-wracking aspects of being an entrepreneur. When a pitch is going well and you're humming on all cylinders, it can be incredibly energizing and give you renewed faith in your abilities and ideas.

On the other hand, there's nothing more uniquely painful or awkward than a pitch meeting that goes sour. The following questions can help you avoid those situations and have more successful and productive pitch meetings going forward.

1.What current projects are you working on? How are they going?

Understanding your potential partner, investor, or client's other projects is a crucial element of your relationship going forward. While they may have reached out to you in order to handle one particular phase or piece of their business, there may be other ways you can work together or add value - and build a more lasting and solid partnership.

When you're listening to the answer to this question, pay close attention to the prospective needs that your client might have; whether their issues involve software, marketing tactics, or other types of services, their answer to this question can be telling for future marketing opportunities.

2.What did you reach out to me/my company and invite me to this meeting?

Knowing why your audience chose to meet with you and your team is perhaps the most valuable insight you can get with regard to their needs, desires, and unique pain points. Not only will this help you tailor your pitch and related materials (case studies, examples, etc.) specifically to each particular potential client, it'll help you understand their overall needs and potentially inform any future pitches.

Are they looking for someone with your unique skill set? Do they need the type of expertise that you or members of your team have? Is there a unique connection - such as being alumni of the same school, or have you worked for the same company - that gave them a reason to reach out to you?

3.What's the one most important aspect you're looking for in a partner?

The answer to this question can be incredibly valuable when assessing whether or not you want to work with a certain company or partner. What you're looking for in a client/partner and what they're looking for should be aligned. A philosophical connection is just as important as ensuring that your skillset or service offerings match their needs, otherwise the relationship may never be as fruitful as you both hope.

Most importantly, try your best to get the real answer to this question; not the "politically correct" answer. Rather, what and who they are actually looking for?

4.What do you personally hope to gain out of this relationship? What does success look like to you?

Understanding the goals of your potential client or investor is one of the most important elements of developing a strong, positive relationship. Even if you already have a basic idea from your initial contact or interview, it's key to hear what they have to say about their goals in their own words.

Seeing an example of how your prospect defines success is a valuable learning experience, since then you can see what they value the most from a partner in general and with regard to your partnership in particular.

5.What are some examples of successful campaigns/companies/business models that you respect?

Knowing who and which brands your client or potential client looks up to can inform your strategies. Whether it's learning from competitors or understanding how their competition has been effective, knowing who they look to for direction and why is an important way to ensure that you'll be successful going forward.

In addition, seeing examples of what your client or potential client considers to be successful will give you and your team valuable direction both during the pitch and throughout the future relationship you are building.

6.Who is the key decision maker on the project?

Always keep in mind that you need to cater (at least little bit) to the person signing the checks. In addition, try to find out whatever you can about the decision-maker(s) in advance. Just knowing some key info can go a long way towards building a successful relationship.

Also, remember whoever you talk to (including receptionists, etc.) may be reporting back to decision-makers as well, so always represent your company with professionalism.

7.Who should I follow-up with after the meeting?

No matter how well the pitch went, you'll want to be able to contact the appropriate person with a quick thank-you for their time. Keep this follow-up brief but respectful.

8.Why should we/I work with your company?

Give them a chance to sell you on the partnership. If they can't offer satisfying reasons about what you and your business have to gain (besides the monetary aspect), this may not be the right partnership for you.

Keep in mind that a pitch meeting is just as much a chance for your potential client to sell themselves to you as you are to them.


Pitching new clients or finding investors doesn't have to be stressful, especially if you ask the right questions and maintain your understanding of your company's value. Also, keep in mind that anyone you are pitching wouldn't have invited you for a meeting if they didn't think you had a strong potential to offer them significant value. Be confident and you'll impart that confidence to your prospect.

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