Herding Cats: Revealing the Biggest Misconceptions Between Salespeople and their Manager

Want to read the other articles from our 3-part “Herding Cats” series? Now’s the perfect time to catch up! In Part 2 & Part 3, we dig into revealing the biggest misconceptions between salespeople and their managers.

For most restoration businesses, staffing is one of the largest pain points in achieving sustained profitable growth. Good employees are hard to find and nowhere in a business is this more noticeable than with the sales team. Statistically speaking, sales has the largest percentage of turnover for any position, even more than mitigation techs. So, what is the cause?  

Ask a sales rep, and they will likely tell you they receive very little to no properly executed training, coaching, or sales management. Without it, they eventually burn out. 

Ask a sales manager or owner, and they will tell you that most salespeople are all bark and no bite, terrible at being managed, and don’t put in enough consistent effort. 

Where does the truth lie? Let’s find out.

I’ve asked Tim Hull, my manager and the president of Violand Management Associates, to join me in this three-part series covering sales and sales management. To start off, I’ll share experiences many capable sales reps encounter while being managed, and Tim will provide insights into the challenges and frustrations of managing a sales rep.

Note: If you’re a sales manager and your sales rep is dramatically underperforming, that’s a different issue. Or if you’re not providing good coaching, that’s also a different issue. In either case, hard decisions may need to be made, and that’s separate from what we’re addressing here.

Tim and I have agreed to professionally pull no punches as we explore this arduous paradigm. What we have put together is a general discussion about the struggles between a proficient salesperson and a competent sales manager, not a personal one between us. (Trust me, I am a delight, and Tim is very lucky to be my manager!)

Together, we identified areas where salespeople and sales managers struggle to see eye-to-eye. In this first part of the series, I will lay out my side of the story. In the second part, Tim will offer his viewpoint toward managing sales reps. Then, in the third installment, we will combine our efforts to provide radical candor, challenge norms, and, hopefully, find common ground.

I have been professionally selling for 25 years, starting with a multi-billion-dollar floor covering manufacturer (big fish in a big pond), then a small family business (small fish in big pond), and now a boutique advisory services firm (small fish in a small pond). I have built a solid career with favorable results across the spectrum, and because of this, I have very strong opinions on sales and sales management. 

In my opinion, managers bear the brunt of responsibility when it comes to a capable and competent sales professional underperforming. Here are several reasons why.

1. Good Reps Want More Freedom and Autonomy and Less Big Brother

Like most sales reps, I do not like being managed. If I wanted to be held accountable, I would be an accountant. The less time I spend with a sales manager talking about what they think I did wrong yesterday instead of focusing on what I need to do today, the better! I know my sales process and it’s unpredictable. To make matters worse, I don’t always have the answer my manager wants to hear. 

Restoration business owners want in-the-box systems and processes, but I live—and thrive—in a world of gray. For me to succeed, my manager must let go. More freedom allows me the ability to make on-the-spot decisions, and agility is a competitive advantage.

If a sales rep is not making calls, they should be let go. They are unlikely to improve, and top salespeople have little patience for under-performers. 

For those who are making calls, they should not be micromanaged, and it should not be assumed that their lack of success is due to a lack of effort. Good reps thrive with a long rope and the opportunity to be creative in solving problems.

Tim’s Take: All top performers want freedom and autonomy in their jobs, regardless of position. The best sales reps have a chip on their shoulder and rightfully so, especially in small businesses. As managers, we strive to achieve a degree of consistency with how we manage employees, systems, and processes. We like order and predictability, not chaos, and we will go to great lengths to maintain this position, often to our own detriment. This is why the rope doesn’t seem to be as long as sales reps would like it to be.

2. Sales Reps Can’t All Be Managed the Same Way

I don’t care why a company wants to manage its entire staff with consistency. I’m telling you, in my sales world a rep can’t be forced to adapt their style and behavior to match the company’s expectation standards. People buy from people they trust, and trust comes from authenticity. As a salesperson, I have a healthy ego, and I want to win. This means, like Frank Sinatra, I do it my way. 

Most sales management systems are designed to manage everyone as though they are an average performing rep. They focus on basic activities and the frequency of connects. If everyone is treated like they are an average rep, they will perform as an average rep.

Tim’s Take: Sales managers don’t know any better. The best sales reps are all too often viewed as having the same persona as an NFL wide receiver. In the game, we want to feed them the ball as much as possible because they are the rainmakers, but there are a lot of other players on the field, and committing to a management standard is important. We’ve been burned too many times by reps who were given an inch and took a mile, so we are reluctant to extend preferential treatment to even our best employees.

3. Too Much Focus on Numbers and End-of-Month Sales, Not on Intangible Selling Skills

I understand that my primary job is to sell, not just to build relationships or scroll through social media. While I may naturally want to share details of the relationships I’m building during my calls and meetings (because it feels good to highlight my efforts), my sales manager may be more concerned with why I didn’t meet my sales goal last month. The challenge is that sales reps focus on leading KPIs, like conversations and prospecting, while sales managers prioritize lagging KPIs, such as monthly sales.

What we really need to discuss is skill development. To improve my performance, I need tools, training, and clear guidance. And while my ego shields me most of the time, it can sometimes get in the way of self-recognizing areas for growth. That’s where managers are needed. Don’t focus on what I am doing wrong. Help me to get better. If I miss a sales goal, trust me, I’m already aware.

Tim’s Take: Sales is viewed as a game of numbers. While we believe there is a direct correlation between efforts and results, sales managers may have a hard time quantifying prospecting efforts. There is no currency with sales “calls” or networking “touches.” We can’t make payroll with “proposals” or make payables with “leads.” These activities need to be converted to sales. We have egos, too, and if the rep missed their sales goal—leading, lagging, or anything in between—awareness is the least of our concerns. Our focus is getting things back on track.

4. Personal Drive vs. Company Goals

This one is tough. My personal drive is to hit the sales goal, but often company goals or objectives say I need to focus on another direction, often on things that don’t directly lead to sales and additional commissions. This happens in small businesses where all employees wear multiple hats. I’m held to a sales goal the manager created and then told to focus my time and energy on something that doesn’t directly help me meet it. 

I want to be a team player, but I also want to take my family to the beach this summer with my commission dollars. I am going to struggle with what is truly most important unless I’m given a real reason behind the “why” of what my manager is telling me they want.

Tim’s Take: Business owners and managers are generally lousy at communicating the strategic priorities of the business, especially in privately held entities. There is no room for individuals who only want to operate within the primary duties of their job description. At the same time, we understand that top performers are going to take the ball if we give it to them. The unintended consequence is that we pile on the most important, challenging, risky, and difficult assignments without telling them the truth … that they are the only ones we trust to get it done!

5. Excessive Time on Bad Reports and Unnecessary Administration 

My primary job is to sell, not spend hours writing reports or completing administrative tasks. The reports most sales managers require utilize the wrong tracking and are disconnected from what actually drives revenue. They offer insight but not into what matters. 

I can make 30 stops in a day if that’s what I’m told to do. But the result will be 30 crappy sales calls for the report, followed by hours of note-writing, which will be a lot of time and effort spent doing something other than trying to close another sale. And if I really am asked to spend an exorbitant amount of time filling out reports and writing notes, I won’t even be able to give you the 30 bad calls you are asking for. Quality will always beat quantity.

Do your company’s sales reports provide a real reflection of sales progress (quality) or do they just show a snapshot of numbers (quantity)? Is my sales manager spending as much time analyzing them as I do to create them? Reports need space to highlight what was learned from each call, the value provided to the prospect, and the recommended next steps. If reports don’t focus on these areas, a good rep has little patience for them.

Tim’s Take: Reporting is often the only way managers have to monitor results. Effort is a baseline expectation of any successful salesperson, so when we ask for reporting, we are less concerned about quantity or quality but about drawing a correlation between the type of effort and the result. Many owners and managers don’t know what it takes to turn a lead into a sale, and quite frankly, they really don’t care. What they do care about is finding what works so more of it can be done. This is only possible through reporting.

6. Lack of New Ideas

No other position in the company gets as many punches to the gut as a sales professional. We may hear no 10 times before we get a maybe. When this happens a couple of days in a row, it’s tough. And when you’re on a losing streak, it’s all too easy to lose focus, drive, and momentum. As a rep, I am in the proverbial line of fire and it’s not easy to take a breath and regroup. 

If my manager’s answer is to just go back out there and work harder, then what you’re telling me is that you want me to fail more. We are never going to agree that’s the best option. I need my manager to help pick me up. I am trying to make the company look good, and when I’m struggling, I need them to give me another way to do so, not just remind me that I am failing.

Tim’s Take: Most managers have a director personality, and empathy is not our strongest quality. We accept failure as a part of the learning process and the natural cycle of sales. As a result, we become calloused to the idea of striking out. If it takes 10 sales calls to get one sale, our mindset is: “How fast can we get to nine?” Where we fail in leadership is sharing the sense of pride we feel when we see a sale go through. We don’t celebrate the wins because we assume the failures don’t hurt, believing they are just part of the equation.

Is the sales manager fully to blame when things go wrong? Of course not. But the sales rep’s responsibility is extremely difficult. That’s why good reps get paid so well and are hard to find. Managing a sales rep is fundamentally different from managing a technician—and not in a good way. But that’s the requirement for the job of a sales manager. In restoration businesses, it’s common for the owner to fill this role, but how much time do they put into growing their skills as a sales manager? In my experience, not much, and this must change.

In the next part of this series, Tim will list general areas where sales managers struggle with their reps, and I will give my take on each.