Crucial Tips for Improving Your Sales Team’s Performance: 2020 Version

Back in 2017 when we originally wrote this, these were meant to address and help clients tackle the biggest challenges and areas of opportunity. Since then many of these have been addressed as a collective sales culture, but some still persist. We believe that now is the right time to revisit this topic and update for 2020.

I should note that if you read the first version you might notice that it has been edited. This was to emphasize and clarify the original points, but also provide a 2020 point of view and add any additional points that we tend to see in sales teams.

As a business owner or sales manager, I’m sure you’ve picked up your fair share of sales tricks throughout your career. Along the way, you’ve probably passed those strategies along to your team.

But with that said, the landscape of the sales industry is constantly evolving. Tactics that you used to reach customers five or ten years ago may not work today.

It doesn’t matter how big your company is or what you’re selling—sales performance starts at the top.

This means that it’s up to you to give your sales team the tools they need to succeed.

As an expert in this in space, I’ve narrowed down the seven most important tips that every sales manager needs to know. Implementing these tactics will increase the performance of your sales team.


It may sound so obvious, but you’d be surprised how many often I consult with companies that haven’t created a sales plan.

Your sales plan will act as a roadmap for your sales team. This plan should outline all of the team’s roles, responsibilities, KPIs, process, and go to market strategy.

This same concept can be applied to your sales strategy. But if you define everyone’s role in the team and explain which tasks need to be prioritized the most, you’re setting them up for success.

Not only is it your job to create the sales plan, but it’s also your responsibility to make sure everyone follows it accordingly.

2020 Update:

We’ve learned over the last 5-6 years that most of the time leaders who are in high growth companies rarely have the time for something like this and that’s alright…until (dramatic pause). Until they’re ready to scale and then it makes scaling (an already difficult task, into a damn near herculean task). In our experience its a luxury to build this all at once with all of the resources at your fingertips. Most high performing companies tend to assemble these as they grow, instead of trying to do it all at once. Most of the clients we work with, hire us because they need help with the heavy lift of doing it all at once and it’s not a small or easy task.

It’s best to help yourself out and bite off chunks as you grow.

One tip would be to have one additional piece added with each additional rep you hire. That way they can act as a ‘trigger’ to remind you but also as a guinea pig to test it with and by a few reps in, you’ll have a team and a complete plan.


What gets measured, gets managed.

Without using specific metrics or analytics, you have no way to know if things are going well or if they need improvement.

If you monitor your sales metrics on a regular basis, you’ll also be able to identify your team’s strengths and weaknesses. This allows you to double-down on the strategies that work, and make adjustments in areas where your team needs improvement.

2020 Update:

Metrics driven sales was ‘all the rage’ from 2015 to 2018. The market was flooded with tools that could track almost every click or step your rep makes. The reason this data and analytics rose to such important stature was that there were nuggets of real gold in the data about how to be more effective when talking to reps and identifying the right times to have those conversations.

Then we hit a bit of a turning point when metrics started to overrule and became too powerful of a measure. Sales processes became too rigid and there was undue burden put on reps to constantly learn new software and comply with new procedures. It began to feel like we were trying to take humans out of sales and automate it.

Metrics in the wrong hands can be over analyzed and be too rigid, but on the other hand no metric insights is missing a ton of opportunity.

So in 2020, there is a balance to be struck. This is why a sales operations function in conjunction with an experienced sales leader tends to be the best combination of sales metrics managing for success. They will know the baseline or benchmarks are and when to correct or follow a trend.

3. Schedule Team Meetings on a Regular Basis

Most businesses have a weekly sales meeting, but how productive are those meetings?

All too often I consult with business owners and sales managers that hold these meetings without a real structure or takeaway value behind them. Most of the time, they just have all their sales reps sit around a table and read out their numbers and talk about why they did or didn’t hit their number.

Your sales meetings need to be laser focused around topics that motivate meaningful actions. These meetings should reinforce the focus, goals, and KPIs that have been outlined in your sales plan, broken down into weekly or daily achievements.

In addition to team meetings that focus progress towards the strategic achievements, it is also important to have meetings with each individual sales rep on a weekly basis.

These one-on-one meetings should be short 30min or less. But it’s a great way to evaluate and offer tailored advice and coaching to your team members.

But understand that there is a difference between pipeline meetings and coaching meetings.

2020 Update:

We’ve seen great effectiveness with meetings, but only ones that have a clear purpose. If you’re failing to have a clear purpose, you’ll have reps schedule over meeting times, be disengaged, and it’s ultimately a waste of time then. Its best to have a clear purpose, agenda, and outcome that everyone will have. Teams of sales reps are incredibly diverse and cannot be treated all the same. That is why you need meeting to address the main needs: team morale, motivation, culture, individual coaching/feedback, and qualitative revenue pipeline.

We have seen great success with clients who utilize 5 types of sales meetings to address those respective areas; Monday Morning Meetings, Friday Weekly Wrap Up Meetings,
Coaching or 1-on-1, Pipeline, and Daily Stand up.

These total only 3.5hrs per week on average, so it’s not a large time commitment when they are organized and prepared for properly. When executed properly, it covers all the necessary needs to feed and maintain a highly productive sales organization.

Monday Morning Meetings (aka Weekly Sales Team Meetings) are the typical weekly sales meetings that set the tone and direction for the week. They are typically an hour long and focus on what needs to be accomplished that week and raising the emotional motivation of the reps for the week ahead.

Friday Weekly Wrap Up Meetings, are a weekly wrap up meeting that is a short 30min recap of the week and is mostly meant to highlight the achievements of the team.

Coaching or 1-on-1 meetings typically focused around calls that have occurred and are a blow-by-blow of prepared analysis and tailored advice for each rep. These are an hour long and occur every other week typically because they take a lot of time to prep for.

Pipeline Meetings are a 30min meeting that happen every other week. They focus not just on what deals the reps have in the pipeline but it is a critical examination of each deal and what could go wrong. It should result in a path to close plan for each deal after the meeting that should be updated in the next meeting.

Daily Stand-ups occur daily first thing in the morning and set the tone for the day. Its a way for reps to get in the right headspace, to warm up, and to hit the floor laser focused on what they need to accomplish. These typically do take place standing and move very quickly around the room. Less than 15min typically. Each rep takes turns talking about what went well the previous day, what they are committing to for today, and identifying any challenges/blockers that would prevent that from happening. Many times the sales leader will present a warm up exercise for the team as well to get their brains and voices warmed up.


The best way to manage your leads is with Customer Relationship Management software, better known as “CRM” for short.

Manually tracking your leads with spreadsheets, whiteboards, or pen and paper are all outdated strategies. But CRM software makes it easy for you to track your current and prospective customers as they move throughout the sales cycle.

Tools like this ensure that all of your leads get followed up within a timely manner and that nobody gets lost in the shuffle.

CRM software can also help you monitor your sales metrics, which we talked about earlier. These platforms can generate reports with analytics that show you how well your team is performing.

You can also use CRM software to help you create forecasts for sales and revenue.

2020 Update:

Back in 2017 when we wrote this, CRMs were the ‘hot ticket’ and were in the mass market adoption phase. Everyone was scrambling to get one. Now in 2020, they are the foregone conclusion and expectation for all organizations. Reps have experience with 2 or 3 nowadays. There are even more choices than ever before.

An emerging trend that will become much more important in the next 2-3 years is that niche industry specific ones have emerged and there are ones that fit the need and growth trajectory for new companies as well.

It’s a widely known secret inside Sales Operations communities that 1% of Salesforce’s install base, is $1B market. That is leaving a large room for niche players to pick off very specific markets.

That is why in 2020, the most important thing is adoption/usability and accuracy at this point rather than just having ‘any old CRM’. The best CRM is the one that your team uses.

At this point there are two major approaches to CRMs, and that is investing in an ecosystem like Salesforce from the beginning and growing into it or scaling your CRM with your business. This can be expensive and complicated, to start, but easier and less painful to scale. The other is to pick the right solution for your current size and needs. For that strategy you’ll end up moving through 2 or 3 different systems throughout the growth of your business. This will be easy to start, because you dont have too much data or customizations to migrate to a new system. As you grow, you’ll likely have to make a hard choice between investing in a new system that is a complicated and extended migration or sticking to a limiting and expensive current system that isnt serving your business very well anymore.

At this point, in 2020, most CRM work and are effective. So just pick the right ones for you and your business, the one that people will undoubtedly use correctly.


As long as we’re on the topic of using technology to improve sales productivity, I figured it would be a good time to talk about email marketing software.

Use automation to your advantage.

Your sales reps can only make one phone call at a time. But email software makes it possible for them to contact hundreds or even thousands of leads simultaneously.

Plus, these tools will give your team added insight and information about your leads and customers. You’ll know specifically which recipients opened the message, and if they clicked on any links inside. You can this data segment your subscribers based on their position in the sales funnel.

Set up automated drip campaigns. These are a series of messages that automatically get sent to new subscribers or customers before, during, and after they make a purchase.

2020 Update:

This is more true than ever, but not from a marketing standpoint, but from a sales efficiency standpoint. Investing in a sales automation/communication software like a Salesloft,, Yesware, Klenty, and many others, you’re able to automate follow up accountability at scale. This not only maximises your rep’s time and efforts, but also gives clients a consistent experience.

For those who aren’t up on these trends yet, these solutions can automate email follow up, calls, voicemails, and even can remind reps when to follow up on deals already in the pipeline, not just prospecting. They can connect and send messages through Linkedin and send text messages as well. They’re incredible powerful software solutions to engage potential clients.

As they say with great power comes great responsibility and these tools have the ability to be incredibly annoying for potential clients when abused. At its’ worst, reps can use them to spam and harass prospects with untargeted and generally poor outreach. At its best, these act as built in playbooks or outreach cadences that demand reps take action instead of managers and leaders needing to make sure they’re doing it, they can know when they do not, which is much more valuable. Think of it as less prodding and more coaching.

If you have yet to invest in a sales automation platform/solution, it’s about time. You’d likely see a 5-10x return on your sales efforts.


It’s not about the product. It’s not about the sales pitch. It’s not about the brand name.

Everything is about the customer.

You need to make your sales team understand this. Have them focus more on who the customer is, what they need, and what they want. Then you can position yourself in a way that solves their problems.

If you’re taking the exact same approach when you’re selling to three different customers then you’re doing it wrong. The “stick to the script” approach is outdated.

Today, customers want a personalized touch, and it’s your responsibility to give that to them.

2020 Update:

By and large this advice still stands, “customers want a personalized touch, and it’s your responsibility to give that to them.”

That is true. Unless you’re in a truly remarkable position and are pioneering a new product category or niche, and even then you have a whole other host of challenges to get your message through. Otherwise in most cases your potential clients are overwhelmed with solutions, choices, and challenges.

They don’t know which is the best solution for them. They are bombarded with information, content, and PTSD from bad salespeople. They are skeptical and distrustful because it’s so easy for new software or service to pop-up and be almost indistinguishable from established ones. That is why now more than ever, clients are learning towards social proof, peer reviews, and referrals.

In 2020, if you want to set yourself apart and connect with people, you want to provide a client centric and personalized approach, make sure to connect them to these sources of information.

7. Motivate Your Sales Team

Driving your sales team goes far and beyond monetary bonuses, prizes, and a fully stocked refrigerator in the break room.

As a business owner, company leader, or sales manager, you need to inspire your staff. Get them excited about making sales.

If you show up to the office looking like you just rolled out of bed and don’t say “good morning” to anyone, that is the tone and expectation you’re setting for the day.

You’ve got to learn how to create a company sales culture that brings your team together and ultimately motives them to perform better.

2020 Update:

This is just as true as ever and will never change. Culture trumps talent.

There is no way that a few good/talented reps can outperform a high performing culture in the long run. You may think of a few times that strong reps have carried a team or company, but you’re probably only selectively remembering the time they did and forgetting about the times they didn’t. Or even if they did it all the time, it didn’t last forever, because it’s unsustainable for one reason or another (ie bankrupting the company or the rep goes somewhere else to make more money).

The point is that, strong cultures raise the bar for the entire team and everyone gives their all. Its been proven over and over again that it’s better to have a team of reps hitting 80% of their quota than just a few reps at 120%.

If you’re a sales leader and you know people could be trying harder and are not the first place you better look, is at your culture.

It starts from the top down.

Sales Leaders set the tone for their team, consciously and subconsciously. Reps are picking up on the small things whether you like it or not, so if you’re a sales leader and unable to handle that level of scrutiny being the leader of a sales team might not be for use. They see when you make excuses, give others a pass, and favoritism. They see if you let failing reps or underperforming reps get second and third chances.

The point is, culture is the rising tide that floats all boats, but it’s easier said than done.


These tips are not difficult to implement. Although some of them may sound simple, you’d be surprised by how effective the results can be.

So keep this list handy and use it to boost the performance of your sales team.

What’s different in 2020.. (besides everything).

Sales agility is the key to winning

In 2020 it’s more important than ever to stay flexible and agile. These are changing times and the sales environment is different now that it was 2 months ago and will be different in 3 months from now. Some of these tips are evergreen and some are timely, but these are where we see most teams have opportunity to grow.

It’s important to have a review process that looks at what is working and why, that is both qualitative and quantitative is fundamental to being a market leader in this new sales environment. Marry the data and analytics to the feedback from reps and clients with and observations of experienced leaders for the best insights and strategies.

Data + Tech are a double edged sword.

In the current environment data and technology is a great advantage but in the wrong hands data can be used as a crutch and it’s too easy to over analyze sales and funnel data, creating a rigid awkward process. There are software solutions for every thing you can imagine and that tech stack can easily become a very expensive burden to a rep.

Sales must be allowed to flow, it cannot be entirely regimented. Structure is important and creates consistency, but as long as humans are involved in buying there must be flexibility in selling.

It’s best to create loose frameworks for reps to work in, templates and guidelines are best. This allows reps to operate at maximum efficiency and efficacy, not just checking boxes to checkboxes.

Humanity is a winning strategy

Whether you want to call it ABM, ABS, or personalization, hyper targeted and personally relevant information is what is going to create successful sales interactions. We already touched on this in the topic about customer centric experience above, but this is important to take it a step further. Mostly because the topic of Account Based Selling, ABM or Account Based Marketing has been such a buzzword for the last 4-5 years.

We are seeing a rise in things like physical mailings, gifts, and 1-to-1 messages resonate deeply with the market these days. People need to be reminded that there is another human on the other end of this computer and that they genuinely care about helping them solve their problems. Taking the time to do that, makes a difference.

So take the time and personalize and be thoughtful. You might be surprised at how when you’re honest and human, how well that resonates with another human being and you might just end up winning a deal from it.

If you’re curious about how to approach or execute on any of these topics the Rose Garden team is here to help. We’ve helped dozens of companies over the past 2 years make meaningful changes to their sales process to achieve new revenue heights. Little changes can go a long way.

Let us show you how. Book time to talk with us here.

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