The Ultimate Sales Checklist to Improve Performance

Modern media will have you believe sales motivation is best delivered in the form of an inspirational quote. But, while an inspirational quote can go a long way, it’s simply not going to fix any deep-rooted sales performance issues.

Unfortunately, there is no one-size-fits-all approach when it comes to diagnosing and fixing a performance issue on your sales team.

That’s why we’ve created this sales performance checklist. This sales checklist will help even the most seasoned sales leaders pinpoint and correct problems happening on their teams.

20 Questions Sales Leaders Must Ask Themselves When Reps Underperform

If you want to improve performance, the following checklist represents the questions you should ask yourself about your sales team and processes. Reflect honestly on your answers, and you’ll be able to identify the problems that are holding back your team’s performance.

1. Does your sales team trust you?

The foundation of any good relationship is trust, and relationships in sales are no exception. If your team doesn’t trust that you have their best interests in mind, they won’t respect your decisions or take your direction. Without trust, your team will feel they have to look out for themselves – because, in their minds, no one else is.

So how do you foster a culture of trust on your sales team? Unfortunately, there’s no quick fix that will help you build trust instantly. But, over time, if you stay true to your word, and act with transparency, your team will begin to trust you. Here are a few of our top tips for earning the trust of your team:

• Give the why. Always explain the ‘why’ behind your decisions. It helps your team feel included in big-picture sales strategy and demonstrates the fact that you want what’s best for your team.
• Have difficult conversations. Act with transparency even if it means saying the hard things. It’s never easy to discipline or call out someone’s poor performance, but doing so directly and without mincing words will help to build trust. Your team will know that you’re always shooting straight with them, without an ulterior motive or hidden agenda, even when it’s difficult.
• Assume the best in people. It’s easy to create stories in your head about how or why someone behaves the way they do, especially when their behaviour impacts you negatively. But the reality is that no one wants to be bad at their job and therefore there’s likely an innocent explanation for poor performance – lack of resources, misunderstanding, or miscommunication. Jumping to conclusions and acting out of frustration will prevent you from getting to the root of the problem.
• Seek out feedback. Asking your team for feedback shows you value their input and understand you’re not perfect. This creates less of a divide between manager and team.

Having a team that trusts you only makes your coaching and direction more impactful. In fact, research shows employees who trust their leaders are 260% more motivated to work.

2. How do you react to failure?

Whether an individual sales rep fumbles a deal or you miss your goals as an entire team, how you react sets the tone for how your team will behave moving forward. If your team interprets your reaction to failure as angry, defensive, or negative, you’ll have trouble rallying them around their next set of goals.

3. Do you trust your team?

Here’s where you need to be fully honest with yourself. Do you trust your sales team to execute on your direction, do the work needed to hit quota, and represent your organisation in a positive light? If you find yourself micromanaging or keeping close tabs on your team, it might be a sign that they don’t have your trust.

Of course, you may have a good reason to withhold trust. Perhaps your team isn’t performing, doesn’t listen, or messes up from time to time – it makes sense why your trust might be a bit shaky.

But when you don’t trust your team, it often becomes a self-fulfilling prophecy. You feel like you can’t trust them, so you start to tighten the reins and apply more pressure. As time goes on, this pressure only makes the situation worse, reps begin to crack, and they behave in ways that only decreases your trust in them further. After a while, it can spiral out of control.

So how do you build trust in your team? Here are a few recommendations:

• Lead by example. Follow through on your promises, act with integrity and transparency, and be open about your own struggles. When your team sees you doing these things, they might rise to the occasion and reciprocate – making it easier for you to trust them.
• Provide opportunities to succeed. How can your team prove themselves worthy of responsibility if you never give them any?
• Set the outcome but don’t dictate the path. Everyone approaches work differently. Two people might arrive at the same outcome but take two very different paths to get there. By micromanaging and dictating the path, you might actually be the factor hurting your team’s performance.

When you trust your team to do the job you hired them for, not only does it free you up to do other work, but it also promotes confidence and motivation among your reps. Think about it – when someone trusts you to do quality work, don’t you feel more inclined to live up to that expectation?

4. Do you keep your promises?

Before you answer yes, think about it from the perspective of your team. How often do you follow through on the things you say? Do you ever mention you’ll look into something or follow up with someone, and then months later realise you never did it?

Moving forward, think about what you say you’ll do and what it may mean to the person you’re talking to. Will it save them time, provide clarity, or move some kind of an obstacle or blocker? If so, you should make an effort to keep your word. If, for some reason, you can’t keep your promise, make sure you follow up and close the communication loop.

Small gestures like this can drastically improve the trust between you and your team and, as a result, improve sales performance.

5. Do you have established paths toward growth and career progression?

Employees in the modern workforce understand their value and they want to commit their working hours to companies who also understand their value. So if you don’t provide your sales employees with a clear path to advance their career, you’re setting yourself up for failure.

If you don’t have a career progression strategy in place, you’ll risk losing your best talent to an organisation that does have one.

6. Have you taken the time to get to know each of the individual contributors on your team?

Do you really know each member of your team? Think beyond surface-level details and ask yourself if you know what motivates each rep, what their preferred work style is, what type of feedback they prefer, what their home life is like, etc.

The more you know a person, the easier it is to tailor your management style to their wants and needs. No two people are exactly the same, and therefore, a one-size-fits-all approach to management will never be the most effective sales management tactic.

7. What does your team’s work-life balance look like?

Although it may seem counterintuitive, spending time away from work and prioritising work-life balance can dramatically improve a person or team’s performance. Check in with your team and see if they’re experiencing burnout. Stress the importance of balance and make sure they’re taking care of themselves. 

Also, make sure you lead by example. If you tell your team not to work unreasonable hours, you shouldn’t be working unreasonable hours. Take mid-day breaks to show your team it’s okay for them to do so as well. It’s one thing to hear a boss deliver empty platitudes about work-life balance – but it’s another thing to see them practice what they preach.

8. Have you set S.M.A.R.T. goals for your team?

Every sales team has goals, which typically come in the form of a sales quota. But, if you’re struggling to hit your goals or notice your team’s performance dip, it might be time to revisit these goals just to confirm nothing’s amiss. Using the S.M.A.R.T. goal framework, here’s what we recommend you look at:

• Are your goals specific enough? If the only goal you give your team is a quota, maybe you need to get more specific and set goals around the sales activities you want to drive. Consider setting goals for number of calls made, number of meetings set, number of emails sent, etc.
• Are your goals measurable? Attaching a number to a goal and making sure it’s something you can easily track plays a huge role in motivating a team.
• Are your goals attainable? Is your team struggling to hit their numbers because of their own actions or is it that your goals are just unrealistic? As a leader, it can be tempting to constantly set stretch goals in an effort to motivate your team. But as a team member, it can be demoralizing to constantly feel like you’re underperforming.
• Are your goals relevant? Do your goals correlate with the organization’s overarching goals? Or are your team’s goals created in a silo, separate from the organization’s priorities? If your team’s goals aren’t aligned with the major goals coming from the very top, their impact won’t be optimal. 
• Are your goals tied to a specific time period? And is that time period appropriate for the goal at hand? Sales reps will be set up for success if they not only have goals, but also know the amount of time it should take them to achieve those goals.

9. How often do you talk to your team as a group?

As a sales leader, it’s important to dedicate an hour or so each week to meeting with your team as a group. Come up with an agenda and allow your team to weigh in on the items included. Then, use the time to go over numbers, offer sales training, swap anecdotes, and allow your team to interact with each other.

Team meetings also give you the opportunity to address your reps all at once. Not only is this helpful logistically when making important announcements, but it also helps with consistency. Your reps will hear the same information delivered at the same time and in the same exact way.

10. How often do you talk to your team as individuals?

Meeting with your reps one-on-one is just as important as meeting with them as a group. The group setting is all about camaraderie and consistency, but when you’re meeting with an individual, you have the opportunity to dig a little deeper and personalise your management approach.

This is where you have the opportunity to get to know your team members as individuals and coach them in ways that aren’t possible in the group setting. To ensure your one-on-ones are effective, be sure to always set an agenda or framework and let your reps know ahead of time what you expect them to bring to the table.

11. Does your team have a hand in choosing their own incentives?

Traditionally, most organisations use their compensation plan to motivate employees. As a sales leader, you already know that not all sales incentives are created equal. Nor are they all financial – you might also offer non-monetary incentives like a President’s Club, travel vouchers, awards, gift cards, flexible schedule privileges, etc.

While you might think you know what your team finds most motivating, do you actually? We recommend giving your team the opportunity to weigh in on what types of incentives they can earn. Their answers might surprise you!

12. As a leader, have you established a shared sense of purpose?

While competition can drive performance, it’s important not to forget the value of camaraderie and how powerful it can be to win as a team. This is why it’s important as a sales leader to establish a shared sense of purpose.

Your team might know their goals and how to achieve them – but do they truly have a reason to come to work each day? Something they can lean on in tough times, or use as their compass to guide difficult decisions? If your answer is no, your sales team might be lacking a shared purpose.

Let’s look at a few vision statements some of the top B2B companies use to establish a sense of shared purpose:

• LinkedIn: To create economic opportunities for every member of the global workforce.
• ADP: To be the world’s authority on helping organizations focus on what matters.
• Zoom: Video communications empowering people to accomplish more.

As a sales leader, it may not be your job to create a vision statement. But, it is your responsibility to make sure team members understand the organization’s vision in a way that is meaningful and motivating to them.

Other ways to facilitate a team-oriented mindset on your sales team include:

• Team incentives: Include an accelerator within your sales commission structure that can only be met when the entire team achieves a goal.
• Randomised coffee calls: Create an ongoing rotation of randomised coffee meetings for different members of your team. As important as it is for you to get to know your reps as individuals, it’s just as important that they also get to know each other.
• Team metrics: Make it a habit to look at reports and metrics that show your team where their group stands within the context of the entire sales organisation. When the rest of the organisation views your team as one entity, it’s easier for your reps to see things the same way.

13. Do you foster a culture of transparency on your sales team?

The phrase “transparency in the workplace” typically refers to the idea that freely sharing information across teams, seniority levels, and peers will ultimately make for a better work environment. But it’s important to foster a transparent culture in the right way.

So what does good transparency look like in sales? Here are a few ways you can bake transparency into your sales processes:

• Real-time access to performance insights. Each rep on your team should know where they stand at all times – whether their performance is above or below expectations.
• Visibility into big picture strategy. Although your reps may not need the nitty gritty details about how a leadership team makes decisions, high-level insight into the process is necessary to contextualise the asks you have for your team.
• Sharing both wins and losses. Normalise sharing both wins and losses. This will help your team learn what strategies to adopt and which to avoid. It will also help your reps feel more comfortable and safe talking about failures – giving them space to accept feedback and improve performance.

If you’re not sure where to start when it comes to creating a more transparent sales culture, ask your team what information they wish they had access to or what information might help them sell better.

14. Are your decisions based on data? And do you share that data with your team?

Having sales data to support your decisions makes you much more credible as a leader. It tells your team that you’re rational and rely on facts to do your job. Moreover, it’s important to share the data that drives decisions with your team. Otherwise, it’s easy for reps to make assumptions about how and when you make decisions.

A transparent, data-driven sales decision-making process takes away the guesswork and leaves no room for assumptions or judgment.

15. What does your alignment with other teams look like?

Successful sales teams have strong partnerships with many other teams within a typical organisation – marketing, finance, sales enablement, customer support, implementation, and onboarding just to name a few. These partnerships are important to the company’s success and ensure a smooth experience across the entire customer lifecycle.

But, alignment with other teams doesn’t happen by accident – it takes a coordinated, strategic effort and ongoing maintenance. It’s your responsibility as a sales leader to make sure you are aligned with the other teams in your organisation to give your team the best possible chance to be successful.

Here are a few quick tips to help you encourage and facilitate alignment between your team and other departments:

• Attitude: No matter how tempting it may be, never badmouth or place blame on another department in front of your reps. Your team will follow your lead and this attitude will ruin the chances of having a productive, working relationship with other teams.
• Encourage idea sharing: Maybe your team members get requests for a specific type of marketing content. Or maybe there’s a feature missing from the products and services you sell that prospects constantly ask for. These are valuable insights to share with the other teams in your organisation, particularly teams that aren’t directly customer-facing.
• Return favours: Sales reps are notorious for having packed calendars and little time to focus on things outside of selling. But returning favours and helping other teams out can go a long way toward building relationships. So, next time you or someone on your team is asked to participate in a marketing program, speak on a webinar, post something on social media, or hop on a customer call – lead by example and encourage your team to do the same.

Although alignment alone might not be the source of poor sales performance, it’s often a contributing factor that can fly under the radar.

16. Do you take the time to recognize both big and small accomplishments?

It’s easy to celebrate big wins – closing a big deal, exceeding quota, etc. Smaller wins aren’t always celebrated as often. But here’s the thing: it takes a string of small accomplishments to ultimately hit those bigger targets you’re aiming for.

Therefore, in order to reinforce the right behaviours in sales, it’s important to celebrate small wins on the path to bigger ones. Pay attention to small improvements and recognise growth on your team. Make sure your team knows you’re paying attention and recognising those successes – even if they seem insignificant in the grand scheme of things.

17. How accessible are you on a normal day?

Does your team know how to reach you on any given day? Do they feel comfortable reaching out when they’re stuck or blocked? If the answer to either of these questions is no, consider making yourself more available to your team. This means making it known that you’re a resource and should be utilised whenever and however your team needs you.

18. Do you make it a point to address bad behavior and remove detractors?

Nothing kills morale or sales motivation like a bad apple: someone who’s constantly negative, hard to work with, or gets away with bad behaviour. This person isn’t necessarily bad at their job. In fact, they might actually be great at their job. But good performance doesn’t mitigate the impact of a rotten attitude.

As a sales leader, it’s your job to recognise detractors and address the negative impact they’re having on the team – and in serious cases, remove them from the equation before they start to infect those around them. Not only does this prevent others from developing bad habits, but it also shows your team you have their back and are willing to deal with tough situations to keep them happy and engaged at work.

19. How does compensation compare to industry standards?

We know money isn’t everything, but it’s an important piece of the puzzle. Sales compensation and commission planning are much more complex than simply paying your sales reps a “good” salary. It’s much more strategic than that.

Ask yourself, what kind of behaviours is this commission structure enforcing? Is it motivating the right behaviours? Or does it promote bad behaviour? Are you missing your targets because the compensation structure isn’t aligned with the overarching business strategy?

Look closely at your commission plans and identify areas for improvement that can directly impact sales performance in a continuously positive way.

20. Can your reps easily track their own sales performance and progress?

Can your sales team pull up a dashboard in a few clicks and see how their progress is measuring up against their short term and long term goals? Or does your team have to manually build and maintain their own reports just to have a vague idea of whether they’ll hit quota?

Too often, the latter scenario is the case. Data lives in too many places, there’s no single source of truth, and sales reps end up with no choice but to maintain their own commission spreadsheets. This eats into reps’ selling time and dramatically impacts productivity.

As the person responsible for removing barriers, confirm that  your team has what they need to be successful –  including transparent reporting, accurate commission data, and tools that automate unnecessary admin work.

Ask the right questions in order to course correct your team’s sales performance

No sales team or sales leader is perfect. There will come a time when you miss a number or come up short. Understanding the reasons behind poor sales performance isn’t easy, but it’s important to diagnose issues as they happen so you can continue to steer your team back on track. Failing doesn’t define a team. But bouncing back and learning from those failures absolutely can.