23 Thought Leaders Answer: What’s Your #1 Tip for a Successful First Meeting with a Prospect?

You worked so hard to get the appointment. Constantly poring over documents, dealing with scheduling blunders, jumping hoops to get some airtime with a decision maker.

Finally, you got it.

You know you’re over the easy part. Here’s the real challenge.

How do you make the first meeting count? How do you take this prospect and add them to your pipeline?

Last week, we published a post about the do’s and don’t’s of first client meetings.

For this article, we went ahead asked business leaders, marketers, and entrepreneurs for their top tip for successful first prospect and client meetings.

Check out their answers below:

Mike Wittenstein Peter Shankman Jeanne Bliss Larry Kim David Worrell
 ♦Rieva Lesonsky ♦ Steve Curtin ♦ Shep Hyken Scott McKain Jordan Wan
Ann Handley ♦ Meredith Wood ♦ Tanveer Naseer Stephen Monaco Nancy Bleeke
Deirdre Breakenridge ♦ Ronn Torossian ♦ John Rampton ♦ Margaret Molloy
Gini Dietrich Martin Waxman ♦ Andy Williamson Walt Lapinsky


Mike Wittenstein


Focus maniacally on outcomes. Your client’s, their clients’, their employees’, their partners’, and yours.

Paying attention to others’ needs quickly identifies all the design or service constraints and it demonstrates that you care about results

Mike Wittenstein is the Founder and Managing Partner at Storyminers. He is a highly sought-after international speaker, experience designer, and strategist. Among his clients are IBM, SAP, CEO Ventures, and Alliance Partners.


Peter Shankman


Easy answer: Do your homework. Nothing drives me crazier than meeting with someone who knows little to nothing about me. It wastes everyone’s time.

Peter Shankman is the founder of ShankMinds: Business Masterminds, a series of small business entrepreneurial-style masterminds in over 25 cities worldwide. Peter is also the founder and CEO of The Geek Factory, Inc., a boutique Social Media, Marketing and PR Strategy firm located in New York City, with clients worldwide. He is best known as the founder of Help A Reporter Out (HARO), helping thousands of journalists on deadline to connect with experts and sources for their stories around the globe.


Jeanne Bliss


LISTEN don’t prescribe.

Understand your customers’ needs, priorities, and their life.  Learn what is important to them. Take the time to build the bond…then earn the right to further discussions.

Jeanne Bliss is the Founder and President of CustomerBliss, and the Co-Founder of The Customer Experience Professionals Association. She is one of the foremost experts on customer-centric leadership and the role of the Chief Customer Officer. Among her clients are the Industrial Supply Association, JD Powers, Loreal, and Southwest Airlines.


Larry Kim


Be flattering. Don’t tell them what they’re doing wrong (even if they’re doing everything wrong).

Focus on what you love about their efforts and how you could help them take their efforts to the next level.

Larry Kim is the Founder and CTO of WordStream, a Google Premier SMB Partner that develops online marketing software, provides managed PPC advertising services, and help marketers and entrepreneurs by giving them online marketing advice through the WordStream blog. He is also a sought-after speaker and advisor. He currently an advisor for several Boston area startups including Curata and ThriveHive.





David Worrell


Always have an agenda.

And on that agenda must be two points:  The first item on the agenda must be “Agree on Agenda”.  And the last point on the agenda must be “Next Steps / Other”.

The “Agree on Agenda” point reminds you to ask the client what would you like to accomplish in this meeting.  (Remember: Listen first, talk second!)  And the last point gives your guest the opportunity to have the last word — making his needs the exclamation mark on the meeting’s wrap up.

David Worrell is a part-time CFO for small businesses and a partner at Fuse Financial Partners. He is the author of The Entrepreneur’s Guide to Financial Statements (Praeger Press, 262pp, 2014)







Rieva Lesonsky


Do your homework.

It’s easier than ever to find information about prospective clients and their companies. Look at their social media accounts to see if there are some personal items you can “connect” on, such as favorite sports teams or travel destinations. Coming into that first meeting prepared gives prospects more confidence doing business with you would be the right decision.

And most important, when you get into that meeting, listen. Listening is an underrated skill.

Rieva Lesonsky is the President and Founder of GrowBiz Media, a content and consulting company specializing in covering small businesses and entrepreneurship. She is a small business & entrepreneurship advocate, journalist & thought leader.




Steve Curtin


Surprise them. Prepare for the meeting in a way that surprises the client/prospect and piques their interest to work with you.

Most will expect you to poke around their website and, perhaps, be aware of recent company news. But they may not expect you to invest the time required to gain insights that will allow you to offer them value they had not expected. Doing so is bound to set you apart by leaving a lasting positive impression on the client/prospect.

Steve Curtin is an acclaimed speaker, author, trainer, and a customer experience expert. Steve has 20 years of experience between hotel operations, sales and marketing, training and development, and customer service roles working for Marriott International, one of the premiere customer-focused companies in the world.




Shep Hyken


In the real estate industry, the three most important words are… location, location, location. In the sales industry, the three most important words are… preparation, preparation, preparation.  

Know your client, their company, their industry and anything else you can learn before your meeting. Come prepared to talk about them and their needs before talking about what you can offer. And, when they ask, “Tell me what you do?” they are really asking, “What can you do to make us more successful?”

Always be amazing!

Shep Hyken, CSP, CPAE is the Chief Amazement Officer of Shepard Presentations. As a hall of fame speaker and NYTimes and WSJ bestselling author, Shep works with companies and organizations who want to build loyal relationships with their customers and employees.


Scott McKain


The fundamental challenge for every entrepreneur, marketing leader, and sales professional is to create distinction for your product or service.

Mindshare always precedes marketshare. While you naturally want to probe for my wants and needs, it’s absolutely critical that you provide some compelling insight for me.

Provide a perspective that challenges my current thinking; deliver a piece of new research that can help me improve my sales; or, enhance my understanding of how we can partner to further our mutual success.

If you can get me thinking at our first meeting…instead of the traditional regurgitation of facts and figures about your product…you have an infinitely greater chance of getting my business.

Scott McKain is a global authority on creating business distinction, a Hall of Fame keynote speaker, a “Top 10 Business Books of Year” author. He is an internationally known authority who helps organizations create distinction in every phase of business and teaches the “Ultimate Customer Experience.” Among his clients are Apple, SAP, BMW, Merrill Lynch, Dow, and Cisco.


Jordan Wan


Don’t pitch, don’t demo.

Your main focus on the first meeting is to learn and listen. Ask questions to get to know the buyer and their pain points. Once you know what you’re solving for, propose a solution and connect it back to the pain points.

Jordan Wan is the Founder and CEO of CloserIQ. CloserIQ connects top sales talent to innovative companies.




Ann Handley


My answer is super simple and very short: Listen more than you talk.

“Nobody learned anything by hearing themselves speak.” That’s not’s mine. That’s Richard Branson’s quote. But I subscribe to it.

Ann Handley is the Chief Content Officer of MarketingProfs; a LinkedIn Influencer; a keynote speaker, mom, and writer. She is a veteran of creating and managing digital content to build relationships for organizations and individuals. Ann is the author of the Wall Street Journal bestseller  Everybody Writes: Your Go-To Guide to Creating Ridiculously Good Content (September 2014, Wiley) and co-author of the best-selling book on content marketing, Content Rules: How to Create Killer Blogs, Podcasts, Videos, Ebooks, Webinars (and More) That Engage Customers and Ignite Your Business (2011, Wiley).




Meredith Wood


Set an agenda at the start of the conversation and strictly follow it.

You want your client to know what’s coming, but also appreciate that you are respectable of their time and aim to have purposeful conversations. In today’s world, when time really is our most valuable assets, people want to work with other people who make sure their time is well spent.

Meredith Wood is the Head of Content and Editor-in-Chief at Fundera, a company that helps small business owners secure loans the easy way.




Tanveer Naseer


In my experience, what has been a key factor to having a successful outcome in your first client meeting (or even a meeting with a prospective client) is to keep the focus on better understanding their needs.  

And by this, I mean having an outward focus to learn about what are their true pain points – what are the real reasons why they’ve sought you out and your expertise.

In many of these first-encounters, what clients first suggest to be the issue they need help with turns out to be only part of a larger issue, something that becomes clear to both of us because I spend most of that first meeting asking questions that revolve not around what they need from me, but what are the challenges they are dealing with that are getting in the way of their team/organization moving forward with their goals.

By focusing on asking questions to learn about the real issues/challenges this client faces, it becomes easier to shape a plan of action that not only addresses their pain points but gives them a clear idea of what the end goal we’re both going to work to achieve going forward.

Tanveer Naseer is an award-winning and internationally-acclaimed leadership writer and keynote speaker. He is also the Principal and Founder of Tanveer Naseer Leadership, a leadership coaching firm that works with executives and managers to help them develop practical leadership and team-building competencies to guide organizational growth and development.




Stephen Monaco


Research the company thoroughly prior to the first meeting but don’t go in with preconceived notions about how you’re going to provide solutions based on your findings about the company – doing so is a big mistake.

Other than asking some open-ended questions to get a dialogue rolling with the prospective client, you shouldn’t do very much talking – at all.

The most important thing you can do is listen.  Don’t politely feign listening while waiting to talk.  Listen carefully to learn and understand.

Stephen Monaco is an IBM Futurist, forward-thinking marketing strategist, and consultant with a remarkable track record of success and over twenty-five years of senior-level executive experience. Monaco is internationally recognized as a digital marketing pioneer for being one of the first to engage consumers directly via online communities — six years before the web browser was invented. Stephen is a best-selling author and the founder of Evolve Adaptive Marketing and the Future Marketing Institute, Inc.




Nancy Bleeke


Be prepared to focus on them.

Use your sources to find out the basic information so you don’t waste precious time covering that information. Arm yourself with relevant questions that others aren’t asking beyond their “needs” or “paint points.” Ask about problems, opportunities, risks, and rewards. Stop the product pitch and instead focus on connecting with them at the level they prefer…this might be personal, business, or a combination. Ask for the second meeting. If you learn about them in the first meeting, they’ll grant you a second meeting to learn more about you.

Nancy Bleeke is the Founder and Chief Sales Officer for Training, Consulting, and Customer Relations at Sales Pro Insider, a firm that provides companies the tools, training, and processes they need to succeed in growing their sales and customer loyalties. She is also the author of Conversations That Sell.




Deirdre Breakenridge


Do your homework on the client/prospect and be well prepared.

Preparation goes a long way. The more effort you put into your prep work, the greater the outcome.  If you can really dig below the surface to uncover your prospective client’s pain points, then you’re sending a signal that you’re a partner who takes the time to understand their industry pressures. Your level of knowledge also demonstrates you’re ready to help the client tackle existing and new challenges.

Deirdre Breakenridge is the CEO of Pure Performance Communications, a company that fuses strategic communications with innovative technology to impact business communications from consumer interest to brand loyalty and advocacy She is the author of four Financial Times/Prentice Hall business books: Putting the Public Back in Public Relations, PR 2.0: New Media, New Tools, New Audiences, The New PR Toolkit, and Cyber Branding.


Ronn Torossian

My top tip for a successful first client/prospect meeting is to be confident, not only in your demeanor but in conveying the results you can produce for the client.

A positive first impression is critical when building a relationship, and coming across as trustworthy is a key way to do so. A client is placing their brand, reputation and capital in your hands, so upon first impression, you should come off as confident and trustworthy.

Ronn Torossian is the founder of NYC based Public Relations Agency, 5W PR. 5W Public Relations is headquartered in New York, with offices in Los Angeles and Denver.


John Rampton


Start your meeting by finding out exactly what the client wants and needs and more importantly how they define success.

When you know what success is for someone, and you complete that, you’ll have much happier clients. You’ll also know what’s expected of you and your team.

John Rampton is a serial entrepreneur. He is the Founder and CEO of Due.com, and is presently the VP for Marketing at Adogy. He was recently named #2 on Top 50 Online Influencers in the World by Entrepreneur Magazine as well as a blogging expert by Forbes. Time Magazine recognized John as a motivational speaker that helps people find a “Sense of Meaning” in their lives. He currently advises several companies in the bay area.


Margaret Molloy


Do your homework, but never assume you are smarter than the client in every way. You can learn a lot about a client’s priorities and business context from external sources, an understanding of client culture and decision-making dynamics requires more internal perspectives.

Margaret Molloy is the Global Chief Marketing Officer and Head of Business Development at Siegel+Gale. She has more than 20 years of experience as a Business-to-Business (B2B) marketing and business development leader at top technology, professional services firms, and marketing agencies. She is consistently listed as a Top CMO on Twitter.






Gini Dietrich


You should go into every new business meeting with the idea that you are going to disqualify them. Look for red flags. Ask the difficult questions that will help you determine whether or not they’re a good fit for your company. Have a list of pass/fail questions. If they make it through all of that, they’re likely going to be a very good client and will save you lots of time, money, and angst later.

Gini Dietrich is the founder and CEO of Arment Dietrich, a Chicago-based integrated marketing communications firm. She is the Author of Spin Sucks. She is the lead blogger at the PR and marketing blog, Spin Sucks, is co-author of Marketing In the Round, and is co-host of Inside PR, a weekly podcast about communications and social media.




Martin Waxman


Before a client/prospect meeting, do your research by reviewing their website/blog and conducting a number of strategic searches. You can start with company and client’s name, the sector, competitors, clients, Google news about the organization and its social feeds. Get a handle on the company’s culture and personality, its goals and vision and what some of their opportunities and challenges may be. Then in the meeting, listen first and ask informed questions.

Martin Waxman is the President of Martin Waxman Communications, a consulting firm that helps businesses with digital, social media and communications training, strategy, content marketing, writing, and social PR.






Andy Williamson


The key to a successful first meeting is doing your research on the prospect – review their website, LinkedIn profiles, and articles about their company and industry. Seek to understand their current challenges and begin formulating possible solutions. Try to anticipate their questions and have responses prepared (with supporting materials if at all possible). Focus the conversation on THEM instead of on YOU; if they feel that you understand their business and their pain points, they’ll be sold on you already.

Andy Williamson is the Managing Partner at Kaizen Analytix where he guides end-to-end solution visioning, business process redesign, and change management activities for clients spanning multiple industries.


Walt Lapinsky


Listen.  You are not there to sell your product or service; you are there to solve their problem.  If you don’t understand their problem and present a solution to it, you will rarely be successful.

Walt Lapinsky is a marketing and tech expert that helps companies take new software products from prototype to profit. I have proven expertise and varied experience in software development, product management and business-to-business marketing of software products and related services.



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Dan Sincavage

Dan Sincavage

Dan is a Co-Founder of Tenfold and currently serves as the Chief Strategy Officer. Dan oversees the Tenfold sales organization, manages strategic partner relationships and works with key enterprise accounts to ensure their success with the Tenfold platform.

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