BL&T No. 118: How to Speed Date (with Prospective Clients)

Borrowed & Learned

I've been leading more early-stage new business calls lately to help fill in for Dan, our Director of Business Development, while he is on paternity leave. Jumping on and off 30-minute calls throughout the week feels like how I'd imagine speed dating. You show up, you both know why you're there, you haven't met yet, and now, you have to figure out if it’s a good fit.

While I've never experienced speed dating, I like the analogy because most people can picture an ideal date. Through the “date mindset,” some obvious tips probably come to mind, like what your potential future partner might think if you spend the whole date trying to tell them how great of a partner you are. You walk away learning nothing about them; they walk away feeling exhausted from hearing your non-stop talking. Well, the same goes for potential clients — no one wants to hear you sell yourself to them.

I initially planned to write this week's newsletter about the tips I keep top of mind when leading new business conversations. However, after I made the connection to speed dating, I decided to lean into the analogy and see how far my expected similarities would go. It turns out they go pretty far.

In this post, I'll transform wikiHow's "How to Speed Date” article into "How to Speed Date with Prospective Clients" by adding my commentary on top of every step.

1) Smile and make eye contact.

I once got feedback from a co-worker that when I leaned my chin on my hand during calls, it seemed like I was disinterested. Once this person pointed it out, I could see what they meant. I’ve since made a conscious effort to stand up straight and show I’m engaged, especially if I’m not leading the call.

Smiling and making eye contact is a simple way to show clients you’re engaged without ever saying a word. This tip might seem obvious but it’s an easy one to violate — even more so on video calls where the allure of multi-tasking is real and “eye contact” is looking at faces in boxes on a screen.

Overall, approaching new business interactions with a positive outlook and attitude goes a long way. This means leaving all preconceived notions at the door and instead, coming with curiosity.

As wikiHow points out, this is a chance to “appear confident” and make a good first impression. Having never met the client, they will weigh these early interactions more heavily. Confidence doesn’t mean convincing the client you can help them with their needs. Confidence means being unafraid to uncover what you can’t.

"What we want to attain is confident humility: having faith in our capability while appreciating that we may not have the right solution or even be addressing the right problem. That gives us enough doubt to reexamine our old knowledge and enough confidence to pursue new insights." (Adam Grant, Think Again: The Power of Knowing What You Don't Know)

2) Break the ice with introductions.

I’ve attended calls where we get caught up talking about topics like the weather, where we grew up, or current events, losing precious time to learn about the client. These conversations might feel lively, but anything uncovered here is rarely of value to the client.

While some small talk can feel necessary to “break the ice,” I prefer to use introductions to get the room warmed up before diving into the purpose of the call. Making time for introductions is also helpful for getting a sense of the client stakeholder’s experience which can (and should) change how you approach the rest of the call.

Similar to wikiHow’s approach to speed-dating, I’ve been starting recent calls by suggesting Barrel begins with intros then we turn it over to the client to introduce themselves and give us a brief overview of the brand. This approach has worked well in covering a lot of ground in under 5 minutes.

3) Ask questions to get to know your client.

If I had to choose the most valuable tip on the list, it would be this one. WikiHow’s advice is pretty spot-on.

For every new business call, I come prepared with the same list of bullet points in my notes to make sure I cover enough ground and touch on what matters most. I prefer this over scripted questions which can make calls feel like an interview and as wikiHow points out, the goal is to have a natural conversation. Coming prepared with high-level topics gives me the freedom to jump around and go deeper with follow-up questions when it feels like there’s more to uncover.

Some examples of topics on my list are founding story, sales channels, and experience working with agencies. I also conduct upfront research ahead of the call to get to know the brand and identify other brand-specific topics to discuss. Podcasts are a great tool for getting new insight into brand directly from key stakeholders, like the CEO or founder.

You might be thinking: what if the client insists on learning about your agency first? Side-stepping this question can make it look like you’re hiding something, so I don’t suggest that. Instead, be prepared with a 30-second overview and end with a question that turns the conversation back to them. If you know the client doesn't know much about your agency (referrals, for example), you might include this overview during introductions to get it out of the way early.

Questions can be valuable in surfacing insights that will help form a proposal, but they also show clients that you want to understand their business before jumping into work together. They might also learn something in the process. The other day I asked a client about their target audience and within a few minutes, learned about their recent success internationally and their roadmap to expand in 2023. This led to me sharing a few insights on our experience working with Shopify Markets. At the end of the call, the client cited the questions they were asked as the reason they were excited to continue the process with us.

"Most people trying to win others to their way of thinking do too much talking themselves. Let the other people talk themselves out. They know more about their business and problems than you do. So ask them questions. Let them tell you a few things." (Dale Carnegie, How to win friends and Influence People)

4) Give honest answers.

"Honesty saves you a lot of time." (Dusan Djukich, Straight-Line Leadership: Tools for Living with Velocity and Power in Turbulent Times)

This topic might be the one people struggle with the most, but is critical for any lasting collaboration, especially during these early conversations. Why is it so tough? Maybe the client’s brand is a perfect fit and we want to win them over. Maybe we’re desperately in need of new work. Maybe we just want to look good.

I love wikiHow’s example of someone afraid of heights saying that they love mountain climbing just to impress their date. Imagine these two people start dating, what happens when the mountain climber surprises the other with a trip to Pikes Peak?

In the new business world, this is equivalent to an agency claiming they have the experience they don’t have or saying their process covers a client’s request when it doesn't. What happens when the client asks to see relevant work as a follow-up? What happens when you start working with a client who expects you to address their earlier request later in the project? That request was never accounted for and will now put the project over budget.

Having the confidence to be transparent is key but there’s an art to framing your honesty. For example, a person who is afraid of heights won’t want their fear to be the reason they lose their chances with the mountain climber. Instead of saying they’re terrified of heights and could never go mountain climbing, they might explain when they learned were afraid of heights, why mountain climbing freaks them out, then talk about other outdoor activities they enjoy.

That said, being honest can open up the doors for topics that are deal-breakers. Getting these out of the way early is better than getting too far along when uncovering them will have a potentially major impact on the relationship. In some cases, it could mean the end. Is looking good to a client worth ruining your reputation with them later on?

Having a network of agencies to refer clients has been a major help here. Rather than taking on work that isn’t within our capabilities, we’re happy to be upfront about what we can and can’t do and then recommend another agency that can help. Clients are often taken aback by this but value our transparency.

"Most of us in sales lead with expertise and a “closing energy” rather than a mindset of curiosity. We know our company’s products and services inside and out, and we’re masterful at quickly linking a client’s needs to our solutions. This is the wellspring of our credibility." (Ashley Welch, Justin Jones, Naked Sales: How Design Thinking Reveals Customer Motives and Drives Revenue)

5) Give positive feedback.

The only piece I’ll add to wikiHow’s suggestions is that giving positive feedback does not mean replying with “mhm” or “yes” to everything the client says. Doing this can have an adverse effect, making the client feel like you’re rushing them or trying to get a word in. Provide feedback like you would a friend or family member to show the client you’re listening and engaged. If you don’t understand something they’re saying, remember tip #4 – be honest!

"Isaac F. Marcosson, a journalist who interviewed hundreds of celebrities, declared that many people fail to make a favorable impression because they don’t listen attentively. ‘They have been so much concerned with what they are going to say next that they do not keep their ears open. ... Very important people have told me that they prefer good listeners to good talkers, but the ability to listen seems rarer than almost any other good trait.’" (Dale Carnegie, How to win friends and Influence People)

6) Respect the meeting's time constraints.

New business calls that run past their allotted time are a pet peeve of mine unless everyone on the call, the client included, decides to stay on longer. In a speed-dating setting, everyone would see who is holding up the entire operation and the downstream impact of doing so. We don’t have that advantage on calls.

Going beyond the allotted time shows a lack of respect for the attendees and even worse, can leave clients with the impression that you are unorganized — a great way to get off on the wrong foot with the client. I try to sense if a call might go over about 10 minutes before it's end. If it seems like it might, I’ll pause the meeting and ask if we should switch gears to make sure we cover any questions the client has or if everyone can stay on for 5-10 minutes longer. Sometimes, you learn that the client has an important meeting with a major retailer. Imagine if you made them late for that! This step is helpful to make the most of the time you have but also avoids the meeting ending abruptly when the client has to go.

7) Close new business calls appropriately.

Another reason to keep your eye on the time is to make space to end the call appropriately. As I’m chatting with the client, I typically start a section in my notes called “next steps.” During the call, I’ll jot down potential ways to move forward after the call. This could be as simple as sending a deck of relevant work or sharing recommendations with agencies in our network.

Before ending the call, I also like to ask what other stakeholders will take part in selecting an agency partner, the timeline for making a decision, and how many other agencies the client is talking with. All of these points are helpful in managing expectations and determining next steps.

When speed-dating, wikiHow suggests that you don’t ask the person out when the date is over. In new business, I’d equate this to not jumping to a proposal after the first call. Unfortunately, there’s no match card to look at after the call, but there should be follow-up discussions to go deeper into the client’s needs and see how you might be able to add value.

Every Conversation is An Opportunity

When I was living in New York, I used to meet new people almost weekly. Sometimes I reached out to folks I admired or found interesting; other times, they were in similar roles at other companies. Either way, I’d often invite them to a nearby cafe called Two Hands for coffee.

On my way to meet them, I’d realize I forgot what they looked like and would start searching LinkedIn. I’d laugh when I’d open my email and find a message that read: “I’m inside in the back with a blue shirt on.”

No, I haven’t done speed-dating but these early morning conversations were great practice for sitting down with someone I've never met and having a fruitful conversation. (I’m also pretty sure the Two Hands staff thought I was speed-dating, especially when I had Tuesday and Wednesday morning meetings. The Wednesday person was late, and the waitress kept asking me if they were coming. She looked so upset — as if I got stood up.) I'm still in touch with many of the folks I met for morning coffee — some have even worked with us on projects.

Since I left New York, I’ve continued this practice via Zoom with people, but now they can be anywhere! These conversations are a great way to deepen relationships and grow my network, but they're also a low-stakes way to continue practicing many of the tips outlined above.

Whether on a date, speaking with a prospective client, or simply meeting someone new, it’s our nature to remember the conversations we enjoyed or learned something new. While it’s important to be prepared, entering these interactions with curiosity and an open mind is a sure way to leave a positive impression and gain something valuable in return.

"Listening is a way of offering others our scarcest, most precious gift: our attention. Once we’ve demonstrated that we care about them and their goals, they’re more willing to listen to us." (Adam Grant, Think Again: The Power of Knowing What You Don't Know)

Thought Starter

Where am I too focused on closing the deal and missing an opportunity to learn more about my prospective client? 

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