How to Go from Transactional to Strategic Sales Skills in 5 Months

May 8, 2018

Man in suit jumping

Who’s thinking about the best way to apply your talents in the months and years to come?

We’ve all seen to-do lists and good intentions set aside in the face of pressing matters and an overflowing inbox. And relying solely on your company for professional development may not always be the best option if your goal is to stay marketable.

The best way to ensure you’re ready for a new opportunity, whether elsewhere or at your current company, is to prepare for advanced situations yourself. That might seem like a daunting task given your current workload, but in this article, we offer tips for breaking down career development aspirations into manageable portions.

The Future of Sales

The sales process has gotten increasingly complex over the last decade. Buyers are armed with information and options, which reduces their reliance on sales reps. Sellers enter the buying process later than in decades past, limiting opportunities for personal consultation.

Recognizing the shift, some sales professionals are moving to a more collaborative approach, enabled by tighter sales and marketing alignment. According to LinkedIn’s recent survey, 58% of marketing and sales professionals reported increased customer retention as a result of collaboration.

A collaborative approach with marketing promotes buyer involvement earlier in the process, often in the vital needs assessment and consideration phases. This increased collaboration gives sellers access to timely data, which they can then use to earn the attention of key prospects.

How Success Will Be Determined

In our e-Book “The Power Couple: How Sales and Marketing Alignment Makes Your Business Unstoppable,” we revealed that of the businesses believing they are delivering a good customer experience, 66% have a clear understanding of their customer. Sixty-four percent collect feedback from customers, with a 57% implementation rate of the findings. Companies which evaluate and enhance the customer purchasing journey commit to putting what the customer needs at the center of what the company needs to do.

Salespeople who take on roles as personal consultants find that the positive contribution deepens the buyer-seller relationship in a way that maximizes the lifetime value of the customer.

Where to Find Help

Now we’ll explain what you can do to ensure you grow your skills accordingly.

1. Improve transparency: Good communication is the key to growing relationships, both internally and with customers. Technology can enable more timely and richer communication so that everyone operates from the same playbook. Sales pros who know how to extract key information from their CRM aren’t just doing themselves a favor in terms of lead gen, they become the go-to people in the department.

An intuitive CRM or lead management system can help salespeople keep track of contacts and relationships. It can document specifics about prospect budgets, needs, and concerns. Some systems also support marketing automation to assist with the nurturing process.

Gain technical skills in these products: LinkedIn Sales Navigator, HubSpot, Pardot, Salesforce, Insightly, Zoho, or other lead management systems. In addition to requesting demos or trial accounts from these or similar companies, you can also pick up knowledge for several of the software leaders at HubSpot Academy,, and Udemy.

2. Learn to produce and adjust more rapidly: As we covered earlier, the state of sales is rapidly changing. Forrester estimates that by the year 2020, 1 million B2B sales jobs will no longer be relevant. While some low-level sales positions may be eliminated, trusted advisors with strategic sales skills will continue to be in demand.

Learn these strategic operational skills:  Agile or scrum methodologies can turn the sales teams of yesteryear into nimble agile agents. Agile is particularly useful when adopted as part of the sales and marketing alignment effort. Good sources of information include LinkedIn LearningMcKinsey & Company, and Content Marketing Institute, and Agile Sherpas. Sales expert Jill Konrath’s book, “Agile Selling,” will also help salespeople adapt to change.

3. Become more self-aware: When sales professionals invest in learning about their identity (self-perception) and reputation (how others perceive them), they can begin to gain a more realistic view of their strengths and weaknesses. Those weaknesses can inhibit a salesperson from realizing their full potential as a collaborative sales professional.

A 2009 report published by the Keller Center of Baylor University found “...research shows that when a salesperson has the ability to accurately appraise the emotions of other people, it amplifies their skills for adaptive and customer-oriented selling. This means that salespeople with high emotional intelligence (EQ) should be able to read clients’ emotions better, use that emotional information to better adapt within the selling situation, help clients solve problems in a way that makes them feel valued, and as a result, improve their overall lead conversion rates.”

Cultivate these soft skills:  Empathy, active listening, humility, and adaptability are valuable skills for effective sales pros learning to identify with others. Training sessions on developing emotional intelligence and communicating with empathy are offered by as is another one, also by Other sources include Udemy, MindTools, and Psychology Today. Harvard Business Review also features a number of articles covering emotional intelligence and the role it plays in career development.

How to Make Development Happen

If it seems like we’re suggesting you go back to school for another few years, don’t worry. Beginning today, you can start a habit of active improvement that will put you in a much stronger position than you started out, with plenty of time to reap the benefits of your new knowledge. Here’s one schedule to try:

Month one: Subscribe to a few reputable blogs covering buyer-driven sales, agile methods, or EQ. Set aside at least 45 minutes each week to read the blogs and reflect on how the information can be applied in your job. The best way to make sure this happens is to block time on your calendar for it.

Month two: Secure a few product demos or register for trials with CRM software providers. If your employer has talked about trying one (or has a subscription you’ve never made use of), take steps to learn about program features and benefits. Experiment with setting up profiles and contacts, and grow your involvement from there. You don’t have to achieve expert-level status to make positive strides you can document on your LinkedIn profile or resume.

Month three: Complete one book. This should comprehensively cover whichever strategic sales skill you’ve set your sights upon.

Month four: Start and complete one or more of the virtual training programs referenced above. Be sure to add them to the Skills section of your LinkedIn profile. As you begin to exercise the new skills in your daily work, consider asking for endorsements to start establishing competency.

Month five: Complete a second book. The topic could be any you didn’t pick the first go-around. Are things starting to get interesting? Would it be beneficial to have a working lunch with your boss or peers to talk over the new material or concepts you’ve learned? Try publishing a post on LinkedIn to showcase your career development efforts.

Learn more ways to future-proof your sales career by checking out our latest e-Book, The Future of Sales: Rise of the Strategic Seller.