•   6 min read

How to train sales reps in the art of outbounding with Krysten Conner

BySamhita Suresh

Published July 2, 2023

Training reps in outbound sales

Ah outbounding - it’s a wild ride. It’s an incredible learning opportunity, a chance to connect and make an impact right from the frontline. It’s also super challenging and stressful. You can’t survive without it, but sometimes you just don’t know how to ace it. And that’s why we figured we bring the experts in to help you out. In Outplay’s Outbound for Dummies series, we unpeel every layer of the onion with sales leaders and mentors who know exactly what they’re talking about. This excerpt is from our session with Krysten Conner, strategist and SaaS sales guru at User Gems. We start from the very beginning with Krysten, by asking her the million dollar question -  how to train reps in the art of outbounding


Why is outbound sales so hard?

Before we dive in, let’s first look at what makes outbound sales the roller coaster that it is. And what exactly reps need to be prepared for and trained in.

Uncertain Responses: When making outbound sales calls or reaching out to potential clients, you never know how they will react. Some may be receptive and interested, while others might be uninterested, dismissive, or even hostile. This uncertainty can make each call or interaction unpredictable and challenging.

Rejection and Resilience: Outbound sales representatives often face rejection multiple times throughout the day. It takes a lot of resilience and perseverance to handle rejection and keep moving forward with a positive attitude.

Pressure to Meet Targets: You all about the quota. The pressure to meet these targets can be intense and stressful, especially when facing resistance from potential customers.

Handling Objections: Dealing with objections from prospects can be difficult. Sales representatives need to be skilled at addressing concerns, overcoming objections, and effectively communicating the value of the product or service they are selling.

Handling Gatekeepers: In the B2B sales context, getting past gatekeepers (receptionists, assistants) to reach decision-makers can be tricky and requires some major persistence and maybe some charm.

Time-Consuming: Outbound sales is super time-consuming as representatives. Not every call leads to a successful sale, which can make the process feel long and challenging.

Constant Learning and Adaptation: Sales techniques and strategies evolve constantly. Sales professionals must continuously learn, adapt, and improve their skills to stay competitive in the market.

Balancing Quantity and Quality: Finding the right balance between making a sufficient number of calls and maintaining the quality of interactions is a constant challenge in outbound sales. 

Success Uncertainty: Even with the best efforts, there's no guarantee of success in outbound sales. Factors beyond the sales representative's control, such as market conditions and customer preferences, can significantly impact the outcome.

Despite the challenges, outbound sales can also be a rewarding and exciting experience for sales professionals who enjoy the thrill of closing deals and building relationships with clients. It requires a strong work ethic, interpersonal skills, and the ability to handle rejection while remaining persistent and optimistic. And it needs managers and sales leaders to empower them with the training and resources to go out and get those meetings booked.

Now, over to Krysten. 


Why is outbound sales so hard

What should reps do before they make their first call?

Prioritize learning about the problems over the product

One thing reps need to know before making their first call is this. They need to understand the personas that they're calling and the problems that they can solve for them MORE than the product. They need to prioritize learning as much as possible about the business problems - and NOT the features and functions of the product they’re selling. You need to match the product to the problem, not the other way around. 


Learn about the specific account

The next thing they need to do is learn something about the account itself, right before the first cold call or email. These are general, but important things. Reps need to ask questions like - How do they make money? How old or new are they? How is their team structured? The answers to these questions will help you understand how fast or slow decisions are made. New companies that are scaling are going to be quick in their decision-making. For older legacy companies that have been around over 30 years with a long serving workforce, decisions are likely to be super slow moving. Knowing this will help you manage and meet your expectations from your sales efforts. 


Understand who you’ve spoken to before 

Another thing all reps should do as part of the account research is understand who they’ve talked to in that account before. Especially to find out what stage the conversation was left at. Was it a discovery call? Did the contact already receive a demo?This knowledge is so important to start with the right context and use the right language as you begin your cold outreach with the new contact.

Looking for some starter tips on building an outbound sales strategy?

Check out this blog for the scoop.

How can reps get the messaging right?

Learn about and target the right personas

There are two distinct types of personas in a prospect organization - those above the line and those below. Above the line personas are the decision makers - the ones with power to control the budget and sign the dotted line. This usually comprises of VP+ and C-level titles. Below the line folks are the end-users - managers and teams.

Priorities, targets and therefore the messaging for these will obviously have to be distinct and unique (more about this as you keep reading). Sales processes are likely to go through multiple departments and levels (sometimes as many as 7!) before they’re any close to a closure. And the messages to each one of those need to keep the interests of the specific persona in mind. 

Hot tip - It is well worth your time to talk to end users within the account to understand the politics of the organization. And to understand the pain that the end users are feeling that their managers or directors or VPS may not know about or understand the impact of. It’s also a great way to learn the vocabulary of the organization. So when you’re having a conversation with a decision-maker, you bring in the familiarity - a great ‘in’

Differentiate between the persona and the person

Managers always educate their teams about personas. But it’s equally important to understand the person behind the persona. Reps should be finding out answers to questions that cover the human aspect - How ambitions are they? Do they want to advance faster in their career? Are they more altruistic? Can you see that pattern on LinkedIn? Do they want a product that saves time? Do they want something that helps save them money? The answers to these questions are deciding factors in your reps messaging.


Optimize the content for mobile

We know that the messaging has to be right. And it has to be short. Stats show that over 80% of people read an email for the first time on their phone. So if your reps are sending them an email that’s too long and involves scrolling, you’ve probably lost them.


What should managers do to empower reps?


Outsource the basic, dedicate time for the details

Ok this one blew our mind. Managers don't have to be the ones directly doing the basic training. 

There are incredible sales trainers and specialist organizations that do this at very budget-friendly prices. Infact, it makes a lot more sense to go this route than to take managers away from their day job to develop content and impart coaching. While outsourced coaching can take care of buyer psychology, communication and more, here’s what managers should do - create a persona matrix. Managers should be handing over a matrix of the personas the business has - A,B,C,D and the top three problems solved for each of them. This really is the secret weapon. Any time a rep is getting ready to write an email or get on a call, all they have to do is look at the matrix and go (for example) today I'm talking with the VP of Marketing, they care about pipeline generation, they care about accountability for where the money is coming from, how can they show return on investment clearly, and voila - ready to go in two minutes. Think of how much more contextual conversations can be. And with all that time saved. 


Transfer insights from customer conversations

In an ongoing extension of the above, there’s one thing managers have the unique power to do to help teams get ahead. Gather and transfer customer insights straight from the horse’s mouth. Managers are in so many more customer conversations, because they have so many reps that they're working with. Using these varied interactions, managers could tell their reps what the common thread is easily. All they’ll need to do is say here are what we’re hearing from customers as their top three pain points over the last 6 -18 months. And that would allow reps to templatize cold email or call scripts without having to reinvent the wheel.


Train them how to have executive conversation

One thing very few companies train reps for is coaching them on how to talk to executives. The difference before and after training can be night and day. Because burning the bridge with a bad first impression, a disastrous demo or discovery - that’s worse than not making a contact. 

It is vital that managers train their reps on how their buyers think, what’s important to them and what’s not, and how they can sound like a peer. For example conversations with a VP or CFO would be all about risks, market share, things that are time bound and have imminent or forward-looking impact. In contrast, reps are generally talking about things more relevant to end-users - and that’s not going to go in their favor.


What should reps be doing to empower themselves?

Block time to practice

This is so simple, it's frequently overlooked. Reps should be blocking time on their calendars to practice. Noone - not even the greatest - would go to perform in a concert or play in a sports tournament without practice. In the same vein, having that time blocked on the calendar and being accountable the one skill you want to get better at can really up everyone’s game. Krysten’s own tip? Put down key talking points of challenges or differentiators on flash cards and practice them every morning till they become like muscle memory. 

Leverage customer stories

Everyone listens to a well told story. Customer stories are the most powerful ways of learning as well as convincing. Another nugget of killer advice from Krysten is this - even if you marketing team doesn’t have access to customer stories, contact the reps of your closed deals and interview them. Ask them everything about the customer problem and the arguments that clinched the deal. 


How can reps be supported by the right tools?

Robust automation and CRM are a must

What a company spends money on is what they value. So if they are spending money to give reps the best-in-class tools that will save them time, that tells you that sales is a priority. If they are struggling with excel sheets and cheaper/unproven tools - reps aren’t going to be able to perform. They need a robust CRM and tools that can automate the easy things, help with scheduling, provide task reminders, and in general - make things easier. 


Walk in the reps’ shoes

Having tools are one thing. But helping reps adopt them is a whole other. Note to managers, If reps aren’t using something, it means they don’t see value in it. The best thing managers can do is to sit down with a couple of their reps and do a ‘day in the life’. If they see the reps bouncing between tools and systems, spending 30% of their time doing anything but sales, there lies the case for tool consolidation or finding a better way of doing things.


How can everyone deal with pipeline anxiety?


Managing expectations from actions

Sales is super stressful at times. We saw that right at the start. Even for the best. And often, managers themselves aren’t trained in helping teams deal with it. The first thing managers should do is pivot their measure of success. And help reps celebrate taking the right actions rather than the outcome. Noone can control outcomes completely. Managers need to account for effort-based numbers. And if something isn’t working, figuring it out is a team effort.


Managing emotions 

This is the most important and underrated one of them all - managers need to teach reps how to manage themselves from an emotional perspective. Navigating the ups and downs, the pressure of targets, the impact of rejection, can all take a toll. Managers need to help reps release the tension they hold on to. Whatever that looks like - meditation, team days off or a one-on-one. 

Phew, that was a good one wasn’t it? Check out the complete session to benefit from Krysten’s expertise. You can find and connect with Krysten here.


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