Most of us don’t wake up thinking, “Today I’m going to be skilling up!”
Similarly, skilling up probably seems too vague to be written out as an item on a to-do list.
Even our managers — the people who tend to be most concerned with our professional development — are unlikely to ask, “How’s your skilling up going?”
Whether you refer to it as skilling up or upskilling, however, the meaning is the same: this is the deliberate practice of deepening your competence in an area like sales, or acquiring new expertise that will help you sell better.
It might be easier to conceptualize skilling up by thinking about the consequences when it doesn’t happen. Reps start to lose out on important ways to connect with customers and prospects, fail to nurture relationships effectively and, eventually, begin to see their win rate plummet and fail to meet their quota.
On the other hand, skilling up might provoke a pretty natural question: “Skilling up to what?” If you’re an experienced sales rep, for instance, do you really need more training about selling, or using the basic skills associated with selling?
The best sales reps will tell you the answer is yes. Rather than settle into complacency or risk falling behind their competitors, they recognize that skilling up is something you’ll never fully complete, because there’s always more to learn.
If you approach it with the right attitude, though, it can also be something that keeps the job fun and interesting. Let’s get started:
1. Get ahead of a performance review with a self-assessment preview
The areas where you need to skill up will often come during that annual time of year where you sit down with your manager and go over what’s happened over the previous 12 months. Sometimes this can be an uncomfortable exercise for both parties, but less so when a rep proactively takes ownership of the process.
Even if your performance reviews at work don’t mandate a step involving self-evaluation, take the time to do one before the meeting with your manager takes place. On a quarterly basis, for example, rate yourself on areas such as:
- Cross-selling or upselling versus closing standard deals
- Demonstrating empathy with customers and prospects
- Negotiating terms and conditions on complex or difficult deals
- Working to shorten the sales cycle
- Driving repeat or loyal customers
The good thing is that none of this has to be subjective. The numbers should all be there in your CRM to help make your self-assessment not only accurate, but actionable.
2. Explore a variety of sources and approaches to skilling up
Depending on where you work, there may be an entire library of resources to help you get to know your company’s products better, refresh your existing sales skills or even take time off for courses that could help you towards earning a promotion.
Companies often provide bursaries or funding to support continuing education, organize lunch n’ learns and carve out office hours with senior leaders for coaching. It’s surprising how often these kinds of opportunities go unused, or at least are under-used by many employees.
You don’t have to rely on your employer to skill up, however. Think about ways you can integrate continuous learning as part of your workday, using all the content and channels available.
You might subscribe to an email newsletter with sales coaching tips you can read during a coffee break or on your lunch hour. Many webinars are deliberately scheduled over lunch hour time periods too, and are available via replay afterwards when you’re at the airport or between meetings. Learn via podcast while driving in your car.
There are all kinds of e-learning opportunities on social media platforms like LinkedIn as well as third-party sites. Don’t overlook anything (including Trailhead!) that might work for you.
3. Unleash anyone’s inner coach with some powerful questions
We would all probably be skilling up more regularly if we had a wise, experienced guru who would take us under their wing and benevolently impart everything they know about selling. Sadly, such coaches and mentors often remain elusive.
Taking the initiative to find coaches and mentors tends to work a lot better. This can be as simple as asking your manager for a few extra minutes each week to go over your goals, or the weak spots you’re attempting to improve upon.
Keep a few questions at the ready whenever you’re talking to someone else who seems like a potential coach or mentor. Some good ones include, “What’s the best buying experience you’ve ever had?” or “What’s the best way for a sales rep to earn your trust?” Another might be, “What do you wish more sales people understood about (fill in the blank)?”
When you show genuine curiosity and desire to learn, people tend to be ready to help. Use these kinds of questions with the next great speaker you hear at an industry event after they’ve wrapped up their keynote. Use them on a friend who works in an industry similar to yours. And don’t forget those buying: your best customers could become de facto coaches in some cases.
The best coaching and mentoring relationships are rarely one-way streets. When you’re looking for insight and advice to skill up in sales, think first about their needs and problems you might be able to help them solve. Bring something to the table in exchange for their time, and you’re likely to get just as much (or more) value back.
Final thoughts
The obvious goal for skilling up in sales is to sell more, but one thing to keep in mind is how you can do that by educating yourself about areas outside sales.
Ensure that part of your plan includes skilling up in the art of marketing, for example, or how customer service teams work today. This is easier than ever because, like sales, these are all areas that are being completely transformed by technology.
The better you can think and work cross-functionally, the more likely everyone in the company will become successful. That’s how real leaders think about skilling up, and why continuously learning becomes the foundation of everything they do.
