“Always be closing.”
In the film “Glengarry Glen Ross,” Alec Baldwin unleashes a fiery sales speech for the ages, and likens customer acquisition to a simple act of willpower. Absent of both strategy and tactics, Baldwin’s pep talk demands results powered only by a relentless, bulldozer-like attitude. In reality, while willpower is an important ingredient for success, sales is an art form in which a wide palette of skills come into play. Many situations require the finesse of a paintbrush rather than the doggedness of an earthmover.
What’s the secret? We sat down with the sales teams of four Colorado tech companies to discuss which sales skills are most valuable, which are the most unheralded and how they can best be developed and strengthened. We learned that deeply understanding the customer’s pain points, developing an organized methodology for success and acquiring a jazz-like ability to improvise are critical components for high achievement. These skills aren’t as simple as A-B-C, but they are just as important for exceeding sales goals.
At TrackVia, a user-friendly app-building platform, Director of Account Management Drew Thompson knows that asking questions and understanding the customer are essential skills in becoming a successful salesperson. By personally understanding the pain points of each client, it becomes not only easier to create specific solutions that close the deal, but to understand when to push — and when to move on to the next opportunity.
What skill do you consider to be the most essential for your success as a salesperson, and why?
When it comes to essential skills, asking great questions is paramount to your success as a salesperson. In a sales situation, it’s easy (and fun!) to speak to all the amazing features and benefits of your solution — and rightly so! You should be passionate and believe in your offering. But don’t get too carried away!
Asking thought-provoking and open-ended questions early and often is much more important than the pitch itself. It’s all about being naturally curious and demonstrating an interest in solving a customer’s problem. Ultimately, without this skill, you’ll never understand the buyer’s pain or problem or know the impact of your solution (and worse, risk losing the deal).
Asking thought-provoking and open-ended questions early and often is much more important than the pitch itself. ”
What’s another skill that is less obvious or less appreciated that you also consider critical for sales success?
Another critical skill that is under-appreciated is the ability to ‘lose quickly.’ Hear me out. There’s a subtle difference between knowing when to walk away from an opportunity and when to really dig in and compete (and hopefully it’s the latter the majority of the time!).
In enterprise sales, you have to sell to multiple buyers with multiple personalities, needs and agendas. You’re also trying to control things that are really out of your control in the first place (budgets, timelines, competitors, unexpected pandemics, etc.). Over time you should become great at pattern recognition for all these factors and begin to develop a framework if you are in the right deal or not.
There’s an opportunity cost for every deal you work and when you compete, compete to win. The more you develop this skill, the more time you can commit to successful sales and not waste time or resources on the wrong deals.
Throughout your sales career, what specific steps have you taken to strengthen these skills?
In order to develop and strengthen these skills, I believe it takes focus and repetition. You’ll learn things from your sales managers, read the latest sales strategies books or blogs, and hopefully have some learning moments from deals you've lost. But all that information can be distracting and overwhelming.
As a salesperson, you’ll have a shot at many opportunities over the course of your career. My advice is to focus on developing a few skills at a time and implement them in your sales process over and over until it becomes second nature. Oh and for all those up-and-coming sales pros out there, remember to give yourself some grace, have fun and learn something every step of the way.
Caitlin Safchik is an account executive at Brandfolder, a cloud-based digital asset management platform. She is a firm believer in the power of thorough organization to fast-track efficiency, prevent errors and improve the understanding of each account. She also believes in the importance of asking questions in order to gain a three-dimensional understanding of the customer, which unlocks the best avenues to a successful sale.
What skill do you consider to be the most essential for your success as a salesperson, and why?
The skill I consider to be the most essential for my success as a salesperson is organization. It’s really important to stay organized throughout the entire sales process so you never skip a beat. As a sales rep we are involved in almost every aspect of the sales process, so if you’re not organized, things will fall through the cracks. I realized early on that keeping my Salesforce up to date and organized has led me to not only become better at forecasting but also to have a better grip on where each deal stands. Additionally, being organized helps my team be informed especially when bringing a solutions engineer into the conversation.
Keeping my Salesforce up to date and organized has led me to not only become better at forecasting but also to have a better grip on where each deal stands.”
What’s another skill that is less obvious or less appreciated that you also consider critical for sales success?
Another skill that is maybe less obvious that I consider critical for sales success is curiosity. There are two parts to this; one is being curious about the company you work for and two is being curious about the prospect’s pain points and how one can actually help them. As a sales rep, it’s really important to ask questions and not just any questions, but the right questions. This will ultimately allow you to get a better understanding if it makes sense to continue conversations vs. wasting time.
Throughout your sales career, what specific steps have you taken to strengthen these skills?
I am always learning from other successful reps and asking questions along the way. I learned quickly that you can’t be afraid to ask questions and it’s OK to not know something. One thing that is critical is being open to feedback and always looking to improve.
Branden Miller is vice president of sales and account management at Choozle, a digital advertising software platform. He views successful sales skills from the perspective of a professional athlete and a jazz musician, specifically the coachability of the athlete and the improvisation and creativity of the musician.
What skill do you consider to be the most essential for your success as a salesperson, and why?
While there are many skills that are essential to be a good salesperson, coachability (with execution) is paramount. When you are a sales professional it’s important to remind yourself that you are a “professional.” Just like a professional athlete, salespeople need guidance daily, weekly and monthly in order to execute well and achieve desired outcomes. If you can’t take feedback, adapt and execute on new directives then it will be much harder to succeed.
Several skills are a very close second: initiative, resilience and consistency.
What’s another skill that is less obvious or less appreciated that you also consider critical for sales success?
Creativity. It’s important to understand that sometimes the process or strategies that have helped you to succeed in the past don’t always work or continue to work. Having a standard process helps drive consistency, but understanding when to be creative is always important. In many conversations, I have related this to jazz. Jazz music has a time signature, key signature and standard riffs that you always play, but there are also places in the music that the player has to improvise (while keeping the structure of the piece in mind). Sales is similar. You have activity KPI, go-to-market strategy and a sales process that all help you create consistent sales, but there are times in prospecting, pitching or closing that you have to be creative and go off-script. Understanding when it’s time to do this often means the difference between a closed deal and a “no.”
There are times in prospecting, pitching or closing that you have to be creative and go off-script.”
Throughout your sales career, what specific steps have you taken to strengthen these skills?
The most important step is to have a standard process. Without having the ideal system outlined and set up, it is nearly impossible to optimize and make things better. In my current position, I set our go-to-market, sales process and accountabilities and then ensure that each of our team members has clarity on these areas. The whole team needs to understand the system and be aligned with expectations to ensure accountability. The next step is to optimize. Systems need to adapt to stay relevant and drive accelerated outcomes. Personally, I schedule a professional “think day” one time per quarter to evaluate how we need to rethink and adapt our strategy and process to improve and then make those changes to start the next quarter.
Get clarity on your process and don’t be so married to it that you cannot make it better. Just like a professional athlete studies their craft and trains hard to get better, sales professionals need to do the same. If you don’t learn, adapt and evolve, you won’t reach your highest potential.
Prep work, alignment and allies are the key tools for sales success at PlayerLync, a mobile workforce enablement platform. Brad Gray, an enterprise account executive, believes in the importance of strategic alignment with every level of the organization. Crucially, he believes in the importance of listening carefully and asking the right questions, which creates new opportunities at critical moments.
What skill do you consider to be the most essential for your success as a salesperson, and why?
Listening and aligning to business goals and strategic objectives of the organization. If not aligned at multiple business levels, IT and other stakeholders, you will not get funded. Also, ask the right questions to help facilitate the qualification of an opportunity, but in a consultative manner.
What’s another skill that is less obvious or less appreciated that you also consider critical for sales success?
Prepping folks for specific calls during the buyer’s journey is key. Understanding which topics are crucial to move the opportunity forward and prepping your team (and their team) so each side is prepared to speak to those topics is important. Also, having a key contact (champion) on the buyer's side to understand priorities and specific areas of concern is a huge benefit throughout the process.
Prepping folks for specific calls during the buyer’s journey is key.”
Throughout your sales career, what specific steps have you taken to strengthen these skills?
Welcome feedback and apply it to create your style and adapt by studying current processes and procedures needed to help the buyer’s journey. Facilitate rep lunches or meetings where you can share best practices and recent learnings.
