Three Ways to Boost your Sales Effectiveness

In 2014, I made a drastic career change and transitioned from owning a marketing company to freelancing full time. I quickly went from leading sales teams to being the salesperson and delivering on what I sold. I became the jack of all trades.

Gratefully, I’ve leveraged my experience owning a marketing agency, in order to help me master the art of effectively prospecting and establishing ongoing client relationships. Like a small business owner, freelancers also have to fulfill and serve customers. When a freelancer is working, he’s earning. When a freelancer is resting, he’s not.

The goal for us is to package our offerings, cultivate a consistent stream of paying clients, and maximize existing client engagements.

So how do we do this while delivering the solutions we’ve sold? While the delivery may not be a top priority for those in sales, it is the most difficult juggle freelancers and solopreneurs face. But, this struggle helped me discover three core insights for effectively prospecting and selling services.

The first insight is having a solid understanding of what value you offer and how to package your solution. The second is knowing & targeting the low hanging fruit first, and the third is embracing your selling style.

Let’s start by exploring what it means to get clear on our offering.

1 - Get Clear On Your Offerings As Early As Possible

When I initially started freelancing, my packaged offerings were simply a list of activities derived from what my previous company offered, but trimmed down to what I could effectively deliver.

Eight months in, I evaluated the projects and people I worked with to realize I was simply working with business owners to help them overcome their communication challenges. Once I discovered this, I was able to organize the strategic and tactical solutions into external communication (Marketing) and internal communication (Vision Casting). Under each of these two sub-categories, I listed four specific services. I was now prepared to precisely communicate with prospects.

Once this was discovered and published on my website, it made sales efforts much easier and less time-consuming. I could now quickly communicate with a prospect in a short call, and have a page to send them as a follow-up.

The more complete our published offerings, the more happy and effective our sales teams become. In fact, I had seasons in my business where good sales people floundered as a result of not prioritizing sales process clarity.

While I’ve made a few small tweaks to my freelance offerings, I’ve kept it intact. This has made it much easier to grow a book of business that financially sustains me. It also allows your sales team the opportunity to provide ideas for iterative fine-tuning.

Are you able to quickly and precisely communicate what challenge your company solves? Is your offering organized and published? Is there a resource available for following up on prospective calls and meetings?

If your answer is yes, jumping to the next insight about understanding your lowest hanging fruit, is a natural next step.

2 - Target High Impact Low Effort Opportunities First

With my marketing company, I heavily relied on outbound sales activities. I was networking, calling and reaching out to others. I was seeking sales from strangers. What I came to realize over the years was this was the hardest road to traverse. As a result of this revelation, I recently flipped my approach upside down and became more tactical when prospecting.

The order in which we target our prospects is critical to effectively and efficiently generate new business. Strangers should usually be the last category we reach out to, not the first (unless that is your specific role). The graphic above communicates how active clients are the easiest source to get new paying projects.

These are people and companies who are comfortable spending money with us and who we’re actively in a relationship with. It’s in our best interest to have a mechanism for discovering pain points and challenges we can help them overcome while we’re working together. The harmony between project management and sales initiatives in your company will determine how effective you are at upselling your existing client base.

I’ve organized my prospects in a way that allows me to see them in the order indicated in the above graphic. As a project manager and doer, I work on active client projects and when their projects are complete, I shift my focus to reaching out to recently active clients.

Here I’m checking the pulse and sharing resources for their benefit. From there, I work on activating inactive clients, closing lead opportunities, and building connections. It’s at the point where I’ve maximized my pipeline opportunities that I’ll begin reaching out to strangers.

As you build out a network of raving fans and loyal advocates, you’ll end up receiving a stream of referrals and leads. Do this well and you’ll find you won’t have to talk much with strangers for drumming up new business.

The critical point here is first to understand how to prioritize our opportunities and second on how we go about creating sources (raving fans & loyal advocates) of the most likely to close opportunities.

How are you prioritizing your sales opportunities? Are you operating from easiest to hardest or the other way around?

If you’ve got this one nailed down, continue onto the last insight revolving around the two types of salespeople.

3 - Embrace Your Selling Style, But Learn To Use Both

In the graphic above, you’ll notice two categories of salespeople, the grill & the crockpot. Another metaphor to help us understand these two approaches is the hunter/gatherer way versus the farming approach. Both the grill and crockpot have their advantages and disadvantages and usually sync with the season we and the company currently reside.

Historically with my outbound sales efforts, I usually leveraged the grill methodology. I was finding the need and pushing the prospect to act on resolving the problem quickly. This led to cold calling, attending hundreds of networking events and meeting with people regularly. While it led to an abundance of new paying work, I was meeting too many people to properly sustain. It also was stressful and required a lot more energy.

When I transitioned to freelancing, I switched to primarily using the crockpot approach. I began blogging, engaging on social media and regularly meeting with people without an agenda. It was a consistent, slow and steady approach to building up relationships that would eventually lead to friendships, referrals, and paid projects. It was highly effective and created a pace of new business that easily aligned with my capacity as a freelancer.

Both styles are necessary for different seasons, and it’s helpful to know how to leverage either approach based on the context we’re currently in. We’ll likely be inclined to use one tactic on a regular basis based on our personality and age. So, embrace that tactic and keep the other option in your back pocket for when you need it.

Depending on the resources you have available within your company, explore how you can better tap into them so you can properly cultivate the contacts and prospects in your pipeline. Where your company does not facilitate this, take the initiative and build your own system for maintaining and growing your network.

Which salesperson type do you relate with? How can you learn to better leverage the other approach?

In Conclusion

As a freelancer, we’re limited on time to move a deal forward and get it closed, so we’ve learned to adapt to this pressure. As you learn to tap into the freelancer’s approach, you’ll have the benefit of solely focusing on the sale. Take this framework to a high level of success beyond what we freelancers could do.

As freelancers and salespeople, our ultimate goal is to build a steady stream of paying clients by leveraging a team of advocates and customers who work with us in an extensive and ongoing way. Getting organized with our offering, targeting low hanging fruit and embracing our selling style are three ways we make it happen.

What do you need to do to make it happen?


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Now a full-time freelancer, Jason Montoya originally moved to Atlanta in 2005 with his wife. He attempted to make an animated feature film, launched a political news website, graduated in 2008 from the Art Institute Of Atlanta, and owned a marketing agency for seven years. Jason lives in Atlanta with his wife and four children and is dedicated to helping freelancers flourish.