Leading Your Sales Team Through a Tough Year-End

This guest post was written by Alex Cook, Manager, Enterprise Sales at Klue

Year-end can be the most exciting time in sales. It can also be the hardest. As an AE, you may be blowing through your number, signing deals, and having the time of your life. You could also be well behind your quota, struggling to stay motivated and worried about job security. As a leader, it’s likely that your team has a mix of both.

I’ve been through plenty of year-ends as an AE. Been on Cloud Nine many times and have also struggled, falling short of where I needed to be. This was my first year going through a year-end managing a team.

For a lot of teams, this year was tough and filled with uncertainty. Next year may be even more so.

And when reps struggle to see the path to their number they may slowly give up, blaming things outside of their control. As a leader, your job is to motivate your teams, hold them accountable, ensure they’re performing at their absolute peak, and ultimately drive revenue.

Managing Through Adversity

A couple of weeks ago, I connected with a great group of like-minded, high-growth sales leaders as part of David Priemer’s Sales Leadership Labs program. We meet a couple of times each month to chat through all kinds of timely topics and on that day, we tackled strategies for motivating your team at year-end (something top of mind for everyone). Something that stood out to me was that regardless of industry, tenure, or leadership title, we were all going through the same thing.

If you’re a sales leader at year-end, whether it’s your first (like me) or your 100th, your team likely fits into one of three categories:

🚀 You’re overperforming on all fronts: Trending well above quota with most of the reps on your team hitting their number.

🔭 You have a hairy path to your number: You have a shot and likely some AEs who are doing very well, some that are within striking distance, and some underperformers.

😬 Your goal is nowhere in sight: It’s clear that you’re not going to get there and nobody on your team is either.

During our discussion, we bounced around ideas and tactics for all three scenarios. But since many leaders found themselves in one of the bottom two categories, here are four things you can do as a leader at year-end when things aren’t going your way.


1. Provide transparency into how decisions are made

When pipelines shrink, close rates decrease, and your team doesn’t see a clear path to the number, they lose motivation, worry sets in, and they start blaming things outside of their control. In fact, you might find yourself feeling the same.

At times like these it’s more important than ever to create as much certainty and transparency as you can by sharing (or perhaps reminding) the “Why” behind the decisions being made.

Why are targets what they are?
Why are territories carved the way they are?
Why are we hiring for the roles we are?

A good example of where it’s helpful to create this transparency is in the areas of quota and year-over-year (YoY) growth.

Picture a scenario where you have a full team of underperforming reps. Naturally, they are going to say that targets simply aren’t attainable. When they do, show them a graph of your company’s YoY growth since its inception. Let’s say every year you grew 30% YoY. This year, you doubled the team, but only grew 10% YoY.

Do the targets still seem too high?

By sharing your mistakes and spotlighting the data used to make key decisions, you’ve now gone beyond individual accountability and created a sense of ownership across the team by attaching them to the overall company’s success.

Take the data one step further and show them the income difference between 10% YoY growth and 30% YoY growth. If your company gives equity, show them the valuation difference five years from now if you continue to grow at 10% YoY vs 30% YoY. You’ve now changed the narrative from “my target is too high and I won’t hit my number” to “if we all hit our numbers, this company is going to the moon and that’s because of us!”


2. Drive accountability to your team target

One of the most common but fun places to be is where you have a chance at your number but it seems like a stretch.

In these cases, you likely have a mix of attainment on your team, with some reps hitting their quota, others with a chance, and some that won’t. That means that across your team, the levels of individual motivation and satisfaction is variable. But if you’re going to hit your team number in this scenario, you need everybody on your team to contribute, regardless of where they sit against their individual targets.

Top-performing reps may be inclined to “sandbag” or slow down if they’re already well past their number, and start planning for a strong Q1. Low performers may have given up on their number and feel a reduced sense of urgency and hustle at year-end.

If you want (or need) everyone on your team to contribute, make them feel attached not just to their individual success but to their team’s success as well. Make sure everybody knows what the team goal is and how you’re trending. Celebrate every win along the way, regardless of how big or small or who drove it. By doing that you’ll create a culture where everybody is doing their all to contribute because they all feel emotionally invested in the group’s success, not just their own.


3. Focus on the leading indicators of success

When I was at Salesforce, we used to talk a lot about the concept of “Doing it Right vs Getting it Done”. The dream state, a rep is getting it done and doing it right. What is your best alternative to that? Some may say getting done is more important than doing it right. Others may say the opposite. But the best, high-growth leaders will take doing it right over getting it done the wrong way ten times out of ten.

If you stay focused on doing the right things, building the right behaviors, and focusing on the inputs, the results will come.

One of the best ways to reframe the performance of somebody who may not be at their revenue goal is to assess whether or not they’re doing the things that will ultimately lead to success in their role. The leading indicators.

What type and quality of prospecting outreach is the rep doing?
How many of those type of actions does it take to build enough pipeline?
How much of that pipeline should come from inbound vs. outbound leads?
How much of that pipeline do I need to hit the revenue number?

David actually shares more about this in his simple formula for high-impact sales coaching. In short, activities lead to pipeline which leads to revenue (and renewal/upsell opportunities).

So if a rep has a high level of activity but a small pipeline, chances are their gap lies somewhere in their prospecting, messaging, or value definition motions. Alternatively, if they have a high level of activity, a lot of deals in their pipeline but are struggling to generate revenue, chances are that their challenges may sit further down the funnel; in issues like discovery quality, negotiation or creating a sense of urgency in the mind of the customer.

Assessing your team from this perspective does a couple of extra things when you’re struggling at year-end (in addition to the obvious of skill development – the purpose this serves regardless of where your team is at):

1. It gives you an area to focus that’s within your team’s control. Improving on a specific skill will then become the reachable target needed to keep your team motivated. If you identify areas to improve and continue to elevate every day, the results will come.

2. It empowers you to reward the right behaviors. Effort and focus should be celebrated, even in advance of the final outcome. While the result may be delayed due to skill gaps or market conditions, when you recognize winning behaviors, you’ll get more of them.

3. It helps you manage up the chain. Think about when your VP or CEO asks you why you’re not hitting your targets. How do you feel if your answer is “I don’t know?” By focusing on the leading indicators, you’re shifting that narrative from “I don’t know” to half my team is low on pipeline because they’re struggling with messaging and value definition. The other half is struggling with negotiation so while the pipeline is there, opportunities aren’t converting. We’re doing XYZ in order to fix these problems, which will ultimately lead to enough pipeline for everyone and a higher close rate to get us beyond our number”. Now that sounds more fun!


As leaders, we all want our teams to be top performers but the reality is, sales is never that easy, especially during periods of economic uncertainty. Regardless of your position or tenure in sales, it’s important to remind yourself and your team members that YOU ARE NOT YOUR QUOTA! So much talk and focus around revenue and quota attainment can lead people to believe that’s all that matters. And when attainment wavers, it can hit reps and leaders alike right in their ego. By creating more transparency into how decisions are made, driving team accountability for the number, and focusing on the right leading indicators, you’ll set yourself up for success in the year to come.


Looking to give your sales leadership game a boost? Learn more about the Sales Leadership Labs program by clicking the image below.

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