10 Steps Sales Leaders Can Take to Prepare for 2020

2019 is almost over. Before you head off for a well-deserved vacation, you need to set the groundwork for a successful 2020. Here are ten things sales leaders can do now to prepare for 2020:

1) Be transparent about your plans for 2020 and communicate it across all team members

Use this year’s performance as a baseline for setting sales goals. As a general practice, sales targets should increase every year. Higher expectations will motivate your team. Even so, you want to make sure that targets are within reach.

To help your team prepare for 2020, try to give them their goals for next year before 2019 ends. This enables them to understand expectations ahead of time and plan accordingly. At the very latest, they should be informed of their targets when arriving back at the office after New Year’s. You want your team to feel motivated, focused, and ready to take on their new goals.

2) Establish recruitment goals for the new year

January is an active month for recruitment, so it’s good to get a head start on ramping up your recruitment efforts. Determine your recruitment goals for the next year and create a timetable for what you will need to do and when.

Although the end of December might not be the best time to post jobs, it’s good to have job descriptions ready to go. Remind your team members that you’re interested in new talent so they can get the word out to friends and family they’ll be meeting over the holidays.

3) Clean up your sales pipeline 

Having a robust pipeline at the beginning of the year is essential for getting off to a strong start in Q1. Closing as many deals as possible should be your ultimate goal as a team but it is better to focus your efforts on more qualified leads than spending too much time nurturing prospects that are not as likely to end in a sale.

The first few weeks of December can be a very productive time for pipeline-building activities. Take advantage of that and encourage your team members to do the same. Use different methods to motivate team members. You might, for example, hold a contest to see who can schedule the most demos during December. This kind of activity can provide a boost in the midst of December weariness. 

4) Create strategies for growing existing accounts in 2020

Chasing new business may be exciting, but don’t neglect the customers you already have. Many of them will be embarking on new goals and initiatives in 2020 as well. You and your reps can brainstorm strategies for growing existing accounts next year and be prepared to execute them. It’s great if you can be prepared to reach out to them early before they’re inundated with work in the new year.

5) Determine areas of improvement for your sales process and formulate a plan for 2020

Even if your team is already doing well, you want to improve your performance in 2020. To that end, it’s worth reviewing your sales process in detail to determine whether there are any weak spots. Review your data in detail. In your one-on-one meetings with sales reps, ask, “What do you think the weakest parts of our process are? Why is this a problem?”

Once you’ve identified the areas that need optimization, formulate a plan and get ready to implement it in the new year.

6) Evaluate how well your strategy for assigning territories and quotas is working

When reviewing your team’s performance for the year, it’s worth considering whether your current system for assigning territories and quotas is enabling everyone to achieve their full potential. Although a rep who consistently underperforms may simply not be up to the job, there might be a larger issue at work.

Ask about this in your meetings with sales reps with questions like “how satisfied are you with your current opportunities?” You might also try to gauge whether any reps are itching to switch territories or verticals.

7) Recalibrate your sales strategy and check its alignment with your company’s goals

Take time to catch up with your company’s leadership and people outside of sales. Use these conversations as an opportunity to learn more about what they’re doing and their goals for 2020. This information can help inform your strategy so that your team is aligned with the larger strategy.

8) Reduce your backlogs and complete all administrative responsibilities

Paperwork might not be the most exciting part of the job, but if you can use December to catch up on administrative work you will be grateful in January. Take an audit of what still needs to be completed and do your best to get it out of the way before leaving for the holiday.

9) Generate more creative ways to inspire your team in 2020

Motivating your team is one of the perennial challenges that sales managers face. As 2019 winds down, take stock of what worked and what didn’t work so well. You’ll want to do more of what worked in 2020, but the new year is an opportunity to try new things.

Motivation looks different for every person, so it’s important to consider individual preferences when brainstorming ideas. Monetary rewards aren’t the only potential carrots. Many members of your team may be motivated by the opportunity to work remotely, or simply receiving public recognition for their accomplishments.

10) Recognize your team’s efforts for 2019 and check in on their personal goals for 2020

Your last one-one-one meetings of the year are great opportunities to check in with team members. Review their major accomplishments during 2019 and express your appreciation for their work. Sales representatives oftentimes appreciate hearing this outside the context of a performance review. Being reminded of early-year accomplishments can be motivating going into the new year.

The end of the year is also a good opportunity to ask team members about new skills they’d like to learn in the coming year. This can help you make decisions about project assignments and give you ideas on training opportunities that you can prepare for 2020.

By using the last month of 2019 to take care of these critical tasks, you can put yourself in a great position once January 1 comes around. You’ll have better chances of reaching your goals if you plan ahead and prepare for 2020. 

James Meincke

James is the Head of Marketing @ Demodesk, the intelligent meeting platform for remote sales. Previously he was the Director of Marketing at CloserIQ.