Humble. Helpful. Empathetic. Active listener. Customer-oriented. Flexible. Solutions-focused. Knowledgeable. Authentic.

When you hear these characteristics, who do you think of?

I think of a star salesperson.

You might disagree, and that's okay. Representations of salespeople in popular culture (and frankly, the personality profile we've been taught to associate with a "typical" salesperson) haven't always fit this mold.

It's time for a mental reset. The best salespeople have always been subject matter experts, put the customer first, and led with their authentic selves. But today, buyers put less trust in us than they ever have, market competition is fiercer than ever, and these traits no longer separate the best salespeople from merely good ones. These are the skills your sales team needs to survive.Watch Now: Experts Share How to Crush Sales in 2019

If you want to develop a more effective salesperson, start with how your organization coaches and trains them.

The Problem With Mini-Me's: Coaching Lessons From an Atypical Career

A unique tension exists in the transition from individual salesperson to sales manager that can lead to ineffective coaching. I often work with new sales managers who think, "If these tactics and scripts worked for me, they'll work for my team." In effect, the manager aims to create a team of mini-me's who will sell and act the way they do.

63% of reps have difficulty changing their methods once they find a system that works for them.

Sometimes, this works. But if this is your management philosophy, I'd bet your team is performing below their full potential.

I experienced this tension myself 10 years ago, when I first started working at HubSpot.

I didn't always want to go into sales. I enrolled at Harvard Business School after spending a few years in finance. On my third day, one of my professors said something that lit a fire: Most Harvard MBAs don't know how to sell. They might build a brilliant product, but they're clueless about how to promote it and demonstrate value to potential buyers.

That generalization included me. On top of not having sales experience, I'm also your typical introvert. I thought if I wanted to be successful in my career, I needed to change my personality to get closer to the extroverted ideal: outspoken and powerful. Part of that transformation meant learning how to sell.

I interviewed for an account executive position at HubSpot and bombed it. HubSpot told me it was a "no."

I emailed the VP of Sales and told him that I disagreed with his decision not to hire me. I even offered to work for commission only for three months to prove I could learn to sell well.

Later, I learned that the way I'd handled this objection demonstrated sales potential. Even though I didn't act or sound like the typical HubSpot salesperson in 2009, the management team thought I was smart, coachable, and could add value. Most importantly, they knew I was committed to learning. I was in. (And don't worry -- I was hired at full OTE.)

My excitement didn't last long. On Day 1, I was rejected more than I'd been in my entire life. I sounded terrified on the phone.

My first manager, a classic extrovert who'd spent decades in sales, tried giving me specific lines and soundbites to use on calls. He soon realized I wasn't seeing results by mimicking him, so he pivoted. He set me up with successful salespeople who were more like me than him, so I could shadow and observe them.

Eventually, I found a style all my own that used my strengths: empathy, listening, and problem-solving. All I had to do to be successful was guide prospects through how to improve their marketing efforts. I wove solution selling into my process starting with the first connect call.

It was a rough start, but within three years I'd been promoted to a sales manager. Today, I'm the vice president of our Global Agency Partner Program. What I assumed would be a six-month gig turned into a 10-year career.

My journey in sales was anything but typical, but I learned three crucial lessons along the way:

1. There's no such thing as a typical salesperson anymore.

A few decades ago, salespeople were gatekeepers of information. Prospects had to speak with you to learn about a product or service because there were no mechanisms for independent research. The options buyers considered were limited to whoever reached out first, broke down objections the fastest, and got them to sign on the dotted line. Personal relationships could make or break a deal.

Today, this couldn't be further from the truth. Buyers research their own problems and potential solutions independently. Products are more replicable than ever, and buyers typically have dozens, if not hundreds, of vendor options. Relationships and trust are as important as ever, but they're not built on shallow rapport. Buyers are looking for business advisors they can trust to craft unique solutions for their unique circumstances.

Salespeople aren't gatekeepers anymore — the sales process can largely happen without us and we need to add unique value along the way to ensure our prospects choose us, not our competitors.

The profile of a "good salesperson" has evolved. Changes in buying behavior have shifted the center of gravity in the sales process from personality to trust-building, opening the door for historically atypical personas (like me) to have amazing sales careers.

This doesn't mean people who do look like the historical sales persona can't be successful in 2019 — but they need to build new muscles and layer a customer-first mentality on top of their existing skill set. Nor does this mean we should start only hiring introverts or business school graduates.

However, it is time to acknowledge that the idea of a "typical salesperson" is dead.

2. The best sales coaching is individualized.

Sales managers who try to create teams of mini-me's will be successful … to a certain extent. Some guidance is better than none, and playbooks are a crucial part of any effective sales process. But it's not enough.

"Sales managers are like professional sports coaches," says Andrew Quinn, HubSpot's VP of Sales Enablement and Productivity. "They may not have been the best players or even played professional sports, yet they excel at coaching professional athletes. The best sales managers might not have been the best reps, but they know how to coach their team to get results."

Truly effective management is about individualized attention, helping someone find their voice, and teaching them how to think about the business problems your company addresses.

There is no effective one-size-fits-all coaching model that accomplishes these goals — I'm living proof of that.

It's worth pointing out that this mini-me mindset has likely contributed to the negative perception consumers have of salespeople. Only 5% of prospects consider salespeople to be trustworthy, and many buyers find it difficult to form a personal connection with reps. Why? I'd bet it's because a lot of us are trying to act like someone we're not, and buyers see right through it.


Source: HubSpot Research

We need to take a cue from our buyers. Every sales process looks different — buyers vary in sophistication, where they are in the sales lifecycle, the goals they're trying to achieve, and problems they're trying to overcome. With so many variables at play, it's difficult to be effective through rote memorization and following sales scripts. Instead, managers should tailor their advice to the selling motions a salesperson is struggling with, in a way that leans into the salesperson's strengths.

3. When building trust, authenticity matters far more than extroversion.

The best salespeople lead with their authentic selves. When I started out in sales, I got fairly basic advice for building rapport — identify commonalities, mirror a prospect's tone and language, and create familiarity through small talk.

If this is genuinely how you connect with people, these tactics can be effective. But if they don't come naturally to you, it will be obvious. Today's buyers are savvy, and the moment they feel you're presenting yourself inauthentically, they'll start doubting the rest of your advice. More importantly, they'll be less willing to disclose their problems, pain points, and goals to a partner they don't find genuine.

How to Develop a Coaching Strategy

At a high level, there are two ways for managers to teach their teams: training by example and by inquiry.

Training by example is the classic coaching technique. Managers show reps successful recordings, scripts, and techniques for them to apply to their work. It's effective so long as the manager provides examples that are authentic to the rep's selling style.

Training by inquiry is more personal. Managers recognize that reps are able to independently solve a problem, so instead of concrete examples, they provide guidance based on the rep's selling style.

Content-wise, sales organization should invest in three types of training: Systems and operations, process, and solution.

1. Systems and Operations

Systems and operations training is typically covered in new hire training and onboarding. Is the salesperson set up on their CRM? Do they have access to the right lead views and reporting dashboards? Do they understand how the different parts of your sales stack work together and what function each tool serves? Do they understand what type of context each tool provides, how to access it, and how to leverage it on calls?

This type of training builds the minimum standard of competence salespeople need to do their jobs. Think of operations training as everything that needs to happen before a new hire can go to their desk, open their laptop, and understand how to navigate through their day.

2. Process

Salespeople need two types of process training: a qualification process to determine who's worth moving through the sales process and an array of sales methodologies to apply to calls in real time.


Qualification training teaches salespeople how to prospect and qualify good-fit buyers. Who are your most successful customers, and what do they have in common? What problems are they typically trying to solve? Just as important — what red flags should salespeople be on the lookout for? Who is your anti-persona?

This process is unique to each business and typically can't be replicated from company to company. Root this training in real data and results, keeping an eye on churn, retention, and customer success. Work with your customer support and service teams to understand where customers stumble and succeed and how to control for this in the buying process.

Sales Methodologies

Sales methodologies are frameworks that enable salespeople to build skills and improve their effectiveness at different parts of the sales process. They're product-agnostic and applicable to a wide range of sales scenarios. Typically, they're branded and sold as training packages, books, and so on.

You're likely already familiar with many well-known and widely-used methodologies, including SPIN, Challenger, and Sandler — you can read more about the most common sales methodologies here.

3. Solution

Just as good-fit training teaches salespeople how to identify good-fit buyers, solution training focuses on how to handle different types of buyer problems they'll face on calls. Solution training has two parts: Product training and solution training.

Product training gets your team up to speed on what they're actually selling. Salespeople should be soup-to-nuts experts in their company's products and services — this is the bare minimum.

Solution training takes this product knowledge a step further. What common problems do your buyers face? How do you work with your buyer to craft a strategy to achieve their goals? Solution training can be as specific as providing your team with battle cards for competitive deals or as broad as teaching business acumen and active listening skills so salespeople have the tools they need to have effective conversations.

Coaching Mechanisms

Finally, a word on how this training gets delivered.

Just as training is not a one-size-fits-all process, the medium you choose for training will deeply affect the outcome. Use a blend of one-to-one, one-to-many, and peer-to-peer coaching depending on what the scenario requires.

One-to-one coaching typically occurs between managers and their direct reports, and it falls into two buckets: pipeline reviews and individualized coaching. One-to-many coaching is best for baseline training (such as a quarterly update on product features) or for exercises like call reviews where a team comes together to provide feedback and advice for one salesperson. Finally, peer-to-peer coaching is an invaluable, often informal, channel for salespeople to get help from other people on the ground.

Source: HubSpot Research

How HubSpot Trains Better

At HubSpot, coaching begins with determining incoming reps' knowledge, skill gaps, and creating growth plans.

Quinn sorts new sales reps' raw skills into three buckets: knowledge, skill, and will.

"Every individual has a mix of those three things, and that's going to shape the way I engage with them based on where those levels are from empty to full," says Quinn.

Our customers feel the same way.

Pamela Firestone, Head of Sales at Skift, says, "The purpose of coaching is to develop sales talent to meet their goals, but also develop them into independent thinkers who can continue to grow and take on more responsibility."

Internally, we invest in a wide array of sales training that fall into the three buckets above. This training is part mandatory, part informal, and partially driven by the individual salesperson (versus mandated by HubSpot). We believe in allowing people to learn in the way that works best for them, so we also use many different mechanisms to deliver this coaching.

1. Operations

All sales hires go through two weeks of standard onboarding that all new HubSpotters attend. Then, we provide an additional two to four weeks of sales-specific sessions depending on role and segment. These trainings cover how to navigate the HubSpot CRM, access leads, create templates and sequences, and more. Periodically, as we update our sales stack, we'll run new team-wide trainings, but for the most part, operations training is covered during onboarding.

2. Process

Process training is done continually at HubSpot and certain portions are used as criteria for promotion as hires progress from business development reps to quota-carrying salespeople.

In new hire training, we require all sales hires to play the role of their buyer and use the HubSpot product to create and grow a business's online presence. This work is presented formally and graded via scorecard. Sales hires are also given extensive training on HubSpot's qualification framework, personas, and so on.

To be promoted from BDR to salesperson, candidates go through multiple one-to-one certifications with a hiring manager. They must demonstrate mastery of their day-to-day process, provide recorded connect calls for review, and role play a mock discovery call. To standardize the process, we use scorecards to evaluate each of these conversations.

3. Solution

Solution training is a combination of formal and informal training.

During the first two weeks of new hire training, salespeople learn to use HubSpot. Then, new sales hires are required to pass methodology and product-specific certifications on HubSpot Academy. Our sales enablement and training teams regularly produce team-wide certifications or trainings as we add to the HubSpot product.

Informally, managers deepen training on specific selling motions, like crafting effective emails, active listening, and negotiation. Some of our segments run this training at a formal cadence, while others use team meetings or call reviews to do so.

Creating a Collaborative Culture

Culture is one of those vague concepts that has concrete implications for how well your sales team operates.

Creating an open culture where knowledge sharing is the norm is one of the best investments you can make in creating a virtuous cycle of continuous learning.

One way we do this is providing mentors for anyone new to their role, even if they're not new to HubSpot. Typically top performers, sales mentors join a new rep's calls and act as a safety net to help answer specific questions. Mentors step back over time as mentees become more independent, but this is an effective way to build peer relationships and encourage knowledge sharing.


Source: HubSpot Research

We also employ "ding notes": emails that are sent to the entire sales team for every deal that gets closed. The email includes information on the buyer and the process of closing the deal. Not only is this a great way to celebrate wins — the dozens of replies you get after "dinging" your first deal are a treasured HubSpot rite of passage — it's also a source of invaluable information the entire team can learn from.

Michael Swope, Chief Business Officer at HomeSmart, also encourages his reps to openly share their success. "Our reps have weekly phone calls where they share best practices, tools, and successes they've had over the last week," says Swope.

Managers who fail to treat reps like individuals and nurture their unique talents create teams that are unlikely to perform. Guiding reps to sell authentically will lead them to listen more, build better relationships, and focus on the customer's needs.

While coaching, you may discover that there's a gap between who your sales team is and who your prospects are. Next week, we'll be talking about bridging this divide through hiring in sales.

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Originally published Mar 4, 2019 8:30:00 AM, updated December 03 2019


Sales Coaching