James Ski

Performance management: finding and managing tomorrow’s sales leaders

Business ops
September 19, 2019

Sales techniques are changing, sales prospects are changing - and salespeople are changing too. Do we need to adjust our management techniques to get the most out of tomorrow’s sales leaders?

This is a chapter from our eBook, 'Scaling B2B sales: how to build a revenue rocket ship', featuring sales leaders from some of the fastest-growing companies around.

We all know what the perception is of sales. Salespeople are commission-obsessed, only driven by money, and only as good as the last quarter’s numbers. And to a degree, that’s fair: an individual’s reason for getting into sales is often money-motivated at first. Typically, as a salesperson, you’ll out-earn your functional peers. But in reality, there’s a point on the axes where joy and happiness in sales doesn’t come from the additional material gain of more money.

As time goes on, people get used to being high-earners and that buzz fades. The value of forming very strong relationships increases in importance. Over time, the individual finesses their style and approach when it comes to engaging with buyers. Before too long, regardless of money, people start genuinely caring about the job culture and environment. The focus shifts over time from dollar signs towards a desire to develop genuine skills and gain recognition from the business.

The actual close on the sale is something that’s slightly different for everyone, but over time, the satisfaction from it doesn’t necessarily depend on the deal value, and what it might mean in terms of commission. Particularly in B2B SaaS with high contract values, a rep might only be closing two or three deals a month. The close as the end of a successful contract can be much more meaningful than the money they’ll make from it - it represents the end of a successful project.

There’s a strong culture of instant gratification that’s creating serious challenges in the sales organisation

With that success comes a new level of comfort. Salespeople accept that throughout their career, they’ll have good months and bad months, good quarters and bad quarters. The importance of that never fades, but as time goes on, again and again I see that it’s the experience of coming to work, and the recognition that salespeople garner in the business as a team member that’s leading from the front, that gives them the greater buzz.

Identifying high performers

During the four years I spent selling at LinkedIn, I was for a time the number one seller in the company, globally. This success allowed me to establish my own network, which in turn set me on a path to create my own business and end up where I am today. Through my experiences before and after starting my business, I’ve encountered huge numbers of sales professionals and candidates, and there are some fundamental traits that salespeople often possess.

In my experience, people who have overcome some form of hardship or significant life challenge - be it personal, familial or professional - often have a drive to perform at their best and prove themselves to others. Similarly, people with a sports background are used to working under pressure, being target-driven, motivated, passionate and energetic - all incredibly useful traits as a salesperson.

But you don’t need to be an athlete to be curious about sales. You don’t need to have a tumultuous past to be successful in sales. It’s nothing to do with academics, either - you can be a first-class Oxbridge graduate, or someone on the complete opposite end of the spectrum, and be equally likely to excel in sales.

You can succeed by being a linear learner who digests things quickly and easily repeats them verbatim, but those individuals often fail to scale the heights, falling down in sales when it comes to joining the dots and thinking on their feet. Ultimately, curiosity is key and non- negotiable: if you’re curious in wanting to understand your buyers, their companies, and how your product or service fits into their routine, you have the most important attribute to becoming a successful salesperson. Self-awareness, drive, passion and energy are also must-have traits in successful young salespeople.

Generation Z: the future sales gurus

Younger candidates have a different outlook to sales than previous generations. This can lead to conflict. The accusation that Generation Z want it all has a lot of truth to it, and expectations are often skewed nowadays. New joiners to the sales workforce want the good money, the great culture, the latest MacBook, the merchandise, and the promotions within six months. This desire for instant gratification creates serious challenges in the sales organisation, or any part of the business that features a stressful, high-pressure, target-driven environment.

If the gap between expectations and reality persists, then colleagues become unhappy, and while mental health concerns are discussed more broadly now than perhaps ever before, the misalignment of expectations can create even more unnecessary stress and exacerbate the situation. A big shift in the last ten years has seen new recruits to the sales workforce join for the money, but also ask about the work-life balance.

This almost never happened when I was starting out - particularly in tech or SaaS businesses. Similarly, recruits weren’t expecting a beer tap in a WeWork and several office dogs to be part of their first week. Managing these changes in expectations is key to cultivating a happy, productive salesforce.

In order to achieve this, you need to create a collaborative, dynamic environment that appeals to Generation Z candidates. Firstly, it’s crucial to communicate everything as clearly as possible. You need to be clear about where the given individual is in their career right now, and how their career progression will realistically map out.

This is about much more than target attainment: if you give people the impression that numbers are all that matter, they’ll quickly start a job, find a way to hit the number and expect a promotion. It’s important to look deeper and see whether they demonstrate the right cultural behaviours to progress towards management roles, and find out whether they support their peers in pursuing their goals.

Beyond the numbers game, you need to establish their depth of understanding: do they genuinely understand the individual buyer’s problems? For example, if they’re targeting a decision-maker at a FTSE100 company, have they learned how to read annual reports and leverage relevant information for sales? That’s just one example, but for enterprise sales there’s a whole layer of key skills that need to be continually developed, in order to genuinely progress. That’s how, as a manager, you push back on career progression - recent graduates can be dazzlingly bright and relentlessly enthusiastic, but even if they develop quickly, you need to make sure there’s more to their development than just numbers.

There are specific tools you can use to track an individual employee’s progress through their career development - indeed there are whole software categories dedicated to it - but if you’re moving quickly and scaling, this might just be a spreadsheet. The important thing is that you make the effort to put in place a process to track their development - whatever that process is - and that you make sure they progress on your terms. Aligning with candidates on this will let them develop and improve their skills at a rate that gives them validation and encouragement, without compromising on what you and the business need from them.

Unleashing the social media natives

It’s beyond question that there’s a generational difference in aptitude for social selling. People joining the workforce now have grown up on social networks, and are much more comfortable than their predecessors where self-promotion is concerned. Conversely, more experienced salespeople can be reluctant to spend time on social selling, filming themselves and leveraging LinkedIn to grow their networks.

The reason behind this is obvious: their own success came without the use of social selling. They became sales leaders and made plenty of money without spending all day on LinkedIn - so why start now? We can often be dismissive of people in this category who seem social-illiterate, but to an extent they’re right - they managed to build and leverage networks to sell successfully all the same.

More senior sales leaders can be dismissive of how much time young salespeople spend building their networks, commenting and sharing content on LinkedIn. But when considering how much time sales hires should spend on social media, it’s important to understand that much of the sales journey is completed before you even pick up the phone. By being socially active, even if it’s not directed at a prospect or a live opportunity, you are preemptively contributing to the success of the company and its salesforce.

Generation Z candidates’ instinctive understanding of social media is one of their biggest advantages to your business. Social selling is only set to increase, and a team of digital natives with the ability to create viral content, drive Twitter engagement or spark LinkedIn conversation could be the edge you need to improve your lead volumes in a crowded market.

Over the years I’ve seen a lot of people progress too early and fail to find enjoyment and success in their new job

Social skills let your salesforce engage creatively with current events - even when it comes to celebrating things like International Women’s Day or Pride month, younger people tend to be much more socially engaged with the subject matter - and more likely to grow their business network because of it. The selfie generation is also much more comfortable filming themselves, and using organic video content to spark discussion and engage prospects. Although video is a hot topic in sales at the moment, it’s rare to meet someone who finds universal success with it. It’s still a delicate balance to find a way to self-promote without being egocentric, whilst at the same time providing value and discussing real customer issues.

Do salespeople make good managers?

Most sales managers have trodden a similar path - working their way up through a career as a salesperson. But it’s hard to gauge whether someone is ready for a managerial position, and for the responsibility that comes with leading a team. A salesperson starts out only being responsible for their own thoughts and behaviours, managing their own stress and the pressure of their job. This changes completely when they become managers, suddenly finding themselves responsible for the behaviours, stress and pressures of their team.

Early-career sales professionals often live with a head-down mentality, trying to establish themselves and understand the goals that will help them succeed as an individual. It’s a different skill entirely to step above that personal focus and look at how the team strives towards success.

The success of a salesperson as a manager is often therefore a matter of timing. The point of promotion needs to be just right; not only for them, but also for the company. Over the years I’ve seen a lot of people progress too early, and as a result, fail to find enjoyment and success in their new job. That can damage their individual motivation, as well as team morale, which is a dangerous outcome for the business.

Creating the right atmosphere

Once an individual has been promoted to management, their hard work isn’t over - far from it, especially in sales. It’s a naturally competitive environment, with people chasing numbers and trying to exceed the expectations set by themselves and the company. The pressure only continues, and it’s easy to become disconnected from the team culture, values and learnings.

For leaders, this can be a huge challenge to overcome - especially for recently-promoted managers. A Hubspot sales survey found that 53% of salespeople new to a role (working at the company for two years or less) rely on their manager for advice and support. As a manager, this means you must foster the instinct to regularly support each other, and understand that true collaboration has to be driven from the top down, through successful leadership.

Above all, make sure there’s a clear structure in place to encourage sharing, learning and being open with each other. The successful people in sales might not be the ones smashing the huge numbers month after month, but rather those that are strong enough to create the right environment and culture for the team to flourish together and achieve company-level goals. These people must be allowed to thrive too.

A scalable approach to mental health

The focus on scaling means that growing fast and adding lots of headcount are inevitable. While exciting, this brings its own performance management challenges - some of which are easier to mitigate than others. In my experience, the majority of solutions revolve around coaching and ensuring you have invested time in continuous development.

In a small team, when everyone is starting out and bouncing ideas off each other, it’s easy to navigate through the team and help each individual hone in on their strengths and weaknesses. As soon as that salesforce broadens out, however, the time available to achieve this naturally diminishes. At the outset, it’s critical to organise yourself and your team efficiently so you can still commit a high quantity of time to coaching - no matter how dramatically you scale.

The truth is that high-pressure sales environments are rife with mental health problems, which must be confronted and addressed in detail on an ongoing basis

And this comes right back to the common misconceptions of salespeople that we need to dispel. We often assume salespeople are confident extroverts, full of charm and bravado, not easily swayed by the struggles of their job. The truth is that high-pressure sales environments are rife with mental health problems, which must be confronted and addressed in detail on an ongoing basis. By committing to their jobs, employees truly invest in the company - by committing to reciprocate, and to invest in them, you not only improve their mentality and approach to their work, but the overall success of the business too.

Taking the time to learn about and understand each member of the team, and to spend sufficient time addressing mental health concerns, should be a cornerstone of performance management. Get it wrong and you risk low morale, disengaged employees and real consequences for individual health. Get it right, and you’ll create a scalable culture of engaged high- performers that will drive business success - and stay happy while they do it.

This is a chapter from our eBook, 'Scaling B2B sales: how to build a revenue rocket ship', featuring sales leaders from some of the fastest-growing companies around.

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James Ski is the CEO and founder of Sales Confidence

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