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The New New Business: Brian Riley with a Fresh Take on Confidence and Connection in Sales


Other Half Creative's VP of business and operations on the ability to sell yourself, finding the right fit and why it's all about the preparation

The New New Business: Brian Riley with a Fresh Take on Confidence and Connection in Sales

Having obtained degrees in fields ranging from Sustainable Development to International Education, Brian spent 15 years in the consulting industry on a wide range of projects. From large-scale tech implementations to managing operations to leading business development, Brian’s diverse experience and business savvy skills bring a fresh and unique lens to the creative industry. He currently serves as VP of business and operations for Other Half Creative.

LBB> What was your first sale or new business win? (Was it a big or small job? How difficult or scary was it? What do you remember about how you felt? What lessons did you learn?)

Brian> What comes to mind is 13-year-old me going door-to-door selling magazines for an 8th-grade fundraiser. As a fledgling youngster, I was motivated by none other than winning the coveted 1st place trip to a theme park called Cedar Point. Despite performing decently well, I didn’t win. However, the experience taught me volumes. There was no training provided and I certainly didn’t know much about the magazine industry. It was just me standing on a doorstep pitching to whoever might open the door...young, old, mean, nice, etc. After a few successes and failures, I began to realise that I was selling myself, or at least in part, and that thread has carried through to today.

LBB> What was the best piece of advice you got early on? 

Brian> Despite my urge to reference the ‘ABC’s’ of closing, I’d say the best advice is really an amalgamation of insights and experiences people have shared with me over time. Piecing those together and finding the nuggets of wisdom that resonate with you, is the way to go. However, I will share one piece of advice I’ve kept close. ‘Confidence and Connection.’ Being confident is a matter of being yourself. People want to trust the person they are considering doing business with, and there’s no better way to engender trust than confidently being yourself. As for ‘connection,’ you have to find the thread where your interests intersect with that of the company you’re selling to. When you marry confidence with connection, building relationships and growing business becomes much more seamless.

LBB> And the worst?

Brian> “You gotta be a hunter!” I get the perspective of keeping on the trail for opportunities, but the term ‘hunter’ doesn’t sit well. It’s not about finding prey, in fact, far from it. You find the best opportunities when you find the right fit. A ‘hunter’ mentality has the connotation of trapping someone. When it comes to new business and sales, neither you nor the client wants to be in an engagement that’s not mutually beneficial. So, I am always trying to assess the ‘fit.’ When you find that, you’ll find a lot more longevity and value in your business prospects and relationships. 

LBB> How has the business of ‘selling’ in the creative industry changed since you started?

Brian> I am not a veteran in this industry. Much of my experience comes from the consulting world where a commonly touted mantra is: Methodology > Creativity. Interestingly enough, the creative industry might argue the inverse is true. As someone representing the business and operations side of a company, I’d argue they aren’t mutually exclusive. Finding a way for methodology and creativity to co-exist through the life cycle of a project can lead to stellar results. We’ve all had projects lean more heavily in one direction or the other on this scale. However, I’ve seen an uptick in clients looking for an honest discussion of how your company can honour and uphold creativity while giving them a level of quality assurance through methodology. Agencies and clients have mounting external pressures of their own, so if you can demonstrate how your company can support creativity while delivering sound, reliable methodology, you’ll be better positioned to win.

LBB> Can anyone be taught to sell or do new business or do you think it suits a certain kind of personality?

Brian> While I do think the skills needed for sales and new business can be taught and honed over time, I would encourage any company to step back and assess the depth of training needed. A series of training calls and on-the-job shadowing is not going to cut it. Anyone can be taught a baseline set of ‘sales skills,’ but the hardest element (and I might argue the most important skill) is emotional intelligence. A salesperson needs to be in tune with the cadence and direction of a conversation. They need to listen to what’s not being said just as much as what is shared. They need to make snap judgement calls on whether to push or pull back, and they need to notice when the emotion of a conversation changes, even subtly. These nuances are hard to train. While someone can harness and develop these skills, I think sales-focused roles do take a certain kind of personality. 

LBB> How do you go about tailoring your selling approach according to the kind of person or business you’re approaching?

Brian> It is all about preparation. Unfortunately, time is something we all struggle to have enough of and most of us are left wanting more time to prepare for a sales opportunity. Focusing on a few key factors can help assuage the tension between time and preparation. First, it’s critical to get to know the person(s) you will be talking to. You can explore several channels to learn about who that person is. Whether it’s social media, LinkedIn, or Google, you can gain insight into that person’s professional experience, role within the company, personal aesthetic or values, etc. Second, it’s equally important to get to know the company, but not just surface-level research. Spend your time looking at the company’s recent blogs and social media posts. Look for any issues the company has taken a stance on recently, or challenges they’ve called out as areas of focus. When time is precious, these two tactics can quickly help you understand what’s important to the company and the people in it. This puts you in an advantageous position to articulate how you/your company either share those same values or can capture them adequately in the campaign or opportunity being discussed. 

LBB> New business and sales can often mean hearing ‘no’ a lot and quite a bit of rejection - how do you keep motivated?

Brian> Rejection can certainly be a motivation killer, but there are a few ways to turn a lost opportunity into something of value. First, not every opportunity is right for you/your company. Second, when you lose a big opportunity, it’s important to take a ‘step back.’ A well-timed step back can make a huge difference. Get all the folks involved in the process together to dissect what went well and what could have been improved. Push the team to come up with at least 2-3 things on both sides of that conversation. Keep these notes somewhere collectively accessible and refer to them the next time an opportunity comes up. But don’t stop there. Continue holding “step-backs” with regularity for a few months until you really hone in on what is working/not working. You are unlikely to get a deep level of insight or those ‘ah-ha moments’ the first time around. As they say, “anything good is worth waiting for.”

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OTHER HALF Creative, Fri, 02 Sep 2022 08:28:11 GMT