How to Start a Persuasive Conversation with an Investor

By Sam Onigbanjo

When it comes to securing investment for your business, the first few minutes of your conversation with an investor are crucial. As an entrepreneur, you’ve likely poured countless hours into your product, service, or startup, but all of that effort can be undermined if you fail to capture an investor’s attention from the get-go.

Investors are bombarded with pitches, often hearing dozens of proposals a week, and their time is highly valuable. That’s why starting a persuasive conversation is not just important—it’s essential. In this blog, I’ll break down how you can make an impactful first impression, build trust quickly, and set the stage for a successful pitch.

1. Know Your Investor

The first step to starting a persuasive conversation with an investor happens before you even meet. Research is key. Investors are people too, and just like your product isn’t a one-size-fits-all solution, neither is your approach to investors.

Spend time learning about their background, previous investments, and areas of interest. What companies have they funded? What stage of business do they prefer to invest in? Are they focused on tech, sustainability, or healthcare? The more you know about their investing preferences, the more you can tailor your conversation to appeal directly to their interests.

Pro Tip: Mention a recent investment they made or a notable achievement in your introduction. This shows that you’ve done your homework and you respect their track record.

2. Open with the Why

In the first 30 seconds, you must answer the question every investor is silently asking: Why should I care? Investors don’t just want to hear about what you do; they want to understand why it matters. Start by framing the problem your business solves.

For example, instead of diving straight into a lengthy product description, say something like:
“Did you know that 60% of small businesses fail within their first three years because they struggle to find affordable financing? We’ve developed a solution that reduces this risk by offering a decentralized lending platform designed to support SMEs.”

This hooks the investor by immediately positioning your business as a solution to a pressing problem.

3. Keep It Simple, Yet Powerful

When speaking to an investor, especially at the start of the conversation, simplicity is your best friend. You might have a deep, intricate knowledge of your product, but the investor needs to grasp it quickly and easily. This doesn’t mean dumbing it down; it means boiling your pitch down to its essential components.

Focus on what makes your business unique in the market, what traction you’ve already gained, and how your solution directly addresses a market need. Use clear, concise language to articulate your vision. Investors don’t want to sift through jargon—they want to understand how you’re going to turn your idea into a successful, scalable business.

Example:
“We’ve developed an AI-powered chatbot that cuts customer service costs by 50% while increasing response times by 30%. In just six months, we’ve onboarded over 200 paying customers.”

This communicates what your company does, the value it brings, and the early traction you’ve achieved—all in two sentences.

4. Inject a Story

People remember stories far better than they remember facts and figures. A persuasive conversation isn’t just about data; it’s about making the investor feel something. Stories help humanize your business and can create an emotional connection with your listener.

Share a short but impactful story that highlights why you’re passionate about what you do, how your business idea came to life, or a pivotal moment that underscores the potential of your solution.

Example:
“We started this company after watching my mother’s small business struggle to get a loan. She had a great product but couldn’t find the financial support to grow. That experience motivated me to find a way to help entrepreneurs like her access the capital they need to thrive.”

A well-placed personal anecdote makes your pitch more relatable and memorable.

5. Ask Engaging Questions Early

Many entrepreneurs make the mistake of talking too much and not engaging enough. A good conversation is a two-way street. After introducing your business and laying the groundwork, ask questions that involve the investor in the discussion.

For instance, after explaining your solution, you might ask:
“I know you’ve invested in companies that focus on financial technology—how do you see the market evolving in the next few years?”
This not only shows that you value the investor’s insights but also creates an opportunity for dialogue, making the interaction feel more conversational than transactional.

6. Present Your “Hook”

Every successful pitch needs a hook—something that grabs the investor’s attention and keeps them intrigued. This could be a standout piece of data, a recent success, or a unique aspect of your business model that differentiates you from competitors.

For example, if your business is already generating significant revenue or has a strong customer base, let the investor know right away:
“We’ve already generated £500,000 in revenue this year and secured partnerships with three major retail chains.”

This immediately signals to the investor that you’re not just in the idea phase—you’re executing and achieving results.

7. Be Ready for the Next Step

As you wrap up the initial conversation, set the stage for what comes next. Whether that’s scheduling a follow-up meeting, sending over additional information, or arranging a formal pitch presentation, be clear about the next steps.

You could say:
“I’d love to share our full deck with you and dive deeper into our financials. Would you be available for a follow-up meeting next week?”

This not only shows that you’re serious and organized but also encourages the investor to commit to continuing the conversation.

Final Thoughts

Starting a persuasive conversation with an investor is about more than just delivering a well-rehearsed pitch. It’s about creating a meaningful dialogue, building trust, and positioning yourself as someone who understands both the market and the investor’s needs.

By doing your homework, opening with impact, keeping things simple yet powerful, and engaging in a two-way conversation, you can increase your chances of not just capturing an investor’s interest, but securing their commitment.

Ready to Dive Deeper? Join Our 8-Week Coaching Program!
If you found this article insightful, imagine how much more you’ll gain from a comprehensive coaching program designed to take your pitching skills to the next level.

In our exclusive 8-week coaching program, we’ll go beyond the basics and dive deep into:

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How to Start a Persuasive Conversation with a Work Collegue

By Sam Onigbanjo

Whether you’re trying to gain support for a new idea, ask for help on a project, or resolve a difference of opinion, having persuasive conversations with colleagues is an essential skill in any workplace. The key to influencing others at work is to build trust, communicate effectively, and align your goals with theirs.

In this blog, I’ll guide you through the steps to starting a persuasive conversation with a work colleague, allowing you to foster collaboration and achieve your professional objectives.

1. Understand Their Perspective

Before diving into any conversation, take time to put yourself in your colleague’s shoes. What are their goals, challenges, and priorities? The more you know about their perspective, the better you’ll be able to tailor your approach in a way that resonates with them.

For instance, if your colleague is focused on efficiency and deadlines, framing your conversation around how your idea will save time or streamline processes will capture their attention more effectively.

Pro Tip: Start by acknowledging their current workload or challenges. For example, you could say, “I know you’re focused on delivering this project on time, and I have a suggestion that might help us meet the deadline more efficiently.”

2. Frame the Conversation with a Shared Goal

One of the most effective ways to start a persuasive conversation is by aligning your proposal with a shared objective. When people feel that your goals align with theirs or with the overall goals of the team, they are more likely to listen and support your ideas.

Instead of positioning the conversation as something that benefits just you, frame it as something that benefits the team, the company, or your colleague directly.

Example:
“I’ve been thinking about ways we can improve our client response times, which is something I know we’re both working towards. I’d love to discuss an idea I have that could help us reach that goal faster.”

By doing this, you immediately create common ground and foster a collaborative mindset.

3. Be Clear and Concise

When persuading a colleague, especially in a busy work environment, clarity is key. Don’t beat around the bush or overcomplicate your message. Instead, get straight to the point while ensuring you communicate the benefits clearly and concisely.

For example, if you need your colleague to adopt a new process, explain the benefits in a straightforward way: “By switching to this new tool, we’ll be able to cut our reporting time in half and reduce the chances of errors, which will ultimately make our work easier and more efficient.”

This keeps the conversation focused on the outcome and shows that you’ve thought about how your idea will make a positive impact.

4. Use Data and Examples

People tend to be persuaded by facts and evidence, so incorporating data or examples to back up your claims can strengthen your argument. Whether it’s a past success, statistics, or case studies, using real-world proof makes your case more compelling.

For instance, you could say:
“I’ve seen other teams implement this strategy, and they reported a 20% increase in productivity within the first month. I believe we can achieve similar results.”

By providing evidence, you’re giving your colleague tangible reasons to consider your proposal seriously.

5. Involve Them in the Solution

A persuasive conversation is a dialogue, not a monologue. Instead of dictating what should be done, invite your colleague to contribute to the solution. This not only makes them feel valued but also increases the likelihood that they’ll buy into the idea because they were part of the decision-making process.

For example, after presenting your idea, ask:
“What do you think about this approach? Do you see any ways we could tweak it to make it work even better for the team?”

This turns the conversation into a collaboration, which boosts your colleague’s sense of ownership and commitment to the idea.

6. Appeal to Their Interests

Everyone has their own set of motivations at work, whether it’s career growth, recognition, or a desire for a better work-life balance. When persuading a colleague, think about how your proposal aligns with their personal interests and how it can help them achieve their goals.

For example, if you know your colleague is keen to take on more leadership roles, you might frame your conversation like this:
“I think this project could be a great opportunity for you to showcase your leadership skills. Would you be interested in co-leading it with me?”

By showing how your idea supports their personal objectives, you make it more likely that they will be on board.

7. Be Open to Feedback

Remember, even a persuasive conversation should leave room for discussion and feedback. If your colleague has concerns or objections, listen carefully and address them thoughtfully. This shows that you respect their viewpoint and are open to collaboration rather than just pushing your own agenda.

Example:
“I see where you’re coming from, and that’s a valid concern. Let’s talk through how we could address that to make this work for both of us.”

Being receptive to feedback not only builds trust but also increases the likelihood that your colleague will engage with your proposal constructively.

Final Thoughts

Starting a persuasive conversation with a colleague is about more than just convincing them to see things your way. It’s about fostering a collaborative spirit, building trust, and aligning your goals with theirs to create a win-win scenario. By doing your research, focusing on shared goals, being clear and concise, and staying open to dialogue, you’ll be well on your way to creating productive and persuasive conversations at work.

Ready to Improve Your Workplace Communication Skills?
If you want to dive deeper into mastering workplace persuasion, collaboration, and leadership, I invite you to join my 8-week coaching program. This program is designed to help you develop advanced communication skills that will not only make you more persuasive but also enhance your ability to build strong, productive relationships at work.

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Advanced Persuasion Techniques: Learn the art of influencing your colleagues and managers effectively.

Conflict Resolution: Discover how to turn disagreements into opportunities for collaboration.

Building Strong Work Relationships: Understand how to foster trust and mutual respect within your team.

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Are you ready to take your pitch to the next level and secure the investment your business deserves?

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