When I became the leader of a sales team for the first time in the mid 90’s, I did not have the luxury of selling for many years and being mentored by someone who could teach me the ropes. Instead, I was a company founder who filled a need that we had at the time to build our sales team, and I kind of made things up as I went along. As I think back to those days, I realize how much I struggled to achieve my goals, and while I was successful, I can’t deny that it probably had as much to do with luck and timing as it did with my will and effort.
It was a time of great learning but there are a few lessons that would have served me well if I had known them in advance.
Here are the top things myself and 28 other sales leaders wish we had known before becoming a Sales Manager:
1. That it’s almost impossible to be a player-coach selling manager
Mike Weinberg – Principal of The New Business Sales Coach and bestselling author of Sales Management. Simplified. and New Sales. Simplified.
“I wish I knew how little most senior executives understand the true job of a Sales Manager and how much crap companies throw on the sales leader’s desk that has nothing to do with leading the sales team. I wish I knew that much of what makes people great as individual producers in sales does not translate to success as a manager. The jobs could not be more different. As a producer, you win on your own, but great leaders win through their people. Night and day difference. I wish I knew that it is almost impossible to be a player-coach selling-manager. To do that, well you have to be schizophrenic. The reason sports teams abandoned the player-coach model is because it’s stupid and produces sub-optimal results while creating a mess.”
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2. To teach my sales team to think differently
Jill Konrath – Sales Keynote Speaker and bestselling author of More Sales Less Time and SNAP Selling
“I wish I knew that not everyone thought as much about how to be successful as I did. After meetings/conversations with prospective buyers, very few sales reps took time to self assess. To help them develop, I needed to teach them how to think differently. I constantly asked: What do you think went well? Why did it work? How can you use it again? Where did you get stuck or run into trouble? What was your role in creating this situation? How could you do things differently next time? What else could you try? Doing this creates an upward spiral. Everyone gets better, driving increased revenue.”
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3. To recognize that I’m playing a long game
Mark Hunter “The Sales Hunter” – Principal of The Sales Hunter and author of High Profit Prospecting and High Profit Selling
“As a sales leader, you likely want to jump in and make every sale happen. It is vital you have wise discernment, though. You must recognize you’re playing a long-game, and as such you should focus on the development of the people you’re leading, not just on chasing short-term customer opportunities. As tempting as it is to close the sale, the bigger benefit is in coaching the salesperson to know how to close the sale when you’re not around. The mark of a sales leader is not what occurs when they’re present, but rather the success their team has when the leader is away.”
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4. The skills that made me a top performer are a small part of what would make me a great sales leader
Kelly Riggs – Founder and CSO of The Business LockerRoom
“I think a lot of sales leaders wish they knew how difficult it was going to be to transition from salesperson to sales leader. The skills that made them successful as an individual performer turn out to be only a small part of the toolbox they need to build a successful team. As a salesperson, they could easily and quickly respond to adversity, but as a sales leader, they often find it quite frustrating that people don’t do things the way they do.”
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5. It’s very difficult to coach and develop sales reps without a structured process in place
Eliot Burdett – CEO of Peak Sales Recruiting, Co-author of Sales Recruiting 2.0: How to Find Top Performing Salespeople, Fast, and Founder of Helping Heroes
“Without many years in sales myself and having to take over leadership of a sales group, I didn’t appreciate the value of a structured selling process. I told my sales reps to call-qualify-develop and close and left them to their own devices beyond this, which meant that each rep sold in their own unique way. Beyond ensuring that customers received different experiences from my sales team, it made it very difficult for me to coach and develop my reps. In short, without a structured process in place, some of the characteristics of a dysfunctional sales team were beginning to reveal themselves.”
6. To spend more time on the hiring than the selecting
Brent Thomson – CSO of Peak Sales Recruiting and Co-author of Sales Recruiting 2.0: How to Find Top Performing Salespeople, Fast
“I wish I had known that what people say and what they actually do are two different things. While your salespeople may tell you something that has transpired, they may not be telling you the whole story. It’s important to have full transparency as it helps them in their sales cycle. It’s important to understand that not everyone lives in the CRM and you need to look for that when recruiting, as that data’s so important. I also wish I had spent more time on the hiring process versus the selection process. It’s much easier to hire than it is to fire someone. Relying on the experts to find you the right people is much more beneficial than selecting someone and having to fire them later due to poor performance.”
7. How to understand the different personality types of people in sales
Tom Hopkins – Chairman at Tom Hopkins International Inc.
“When I first moved from sales into a sales management position, I was fortunate that my company sent me for some training. The most important lesson taught was about understanding the different personality types of people in sales. Previous to this, I thought everyone would handle their business the way I did. Upon taking over, I quickly learned that you cannot manage everyone the same way. Each person on the team had a different temperament, a different attitude, and was motivated by different things. Once I got a handle on each person’s wants, needs, and desires, I was able to take an office that was on the bottom of the revenue-generation pile and turn it into the first place office in the company.”
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8. A sales manager’s job is not to be the best seller on the team
Colleen Francis – Owner of Engage Selling Solutions and author of Nonstop Sales Boom
“I wish I knew before becoming a sales leader/manager that 1+1 = 3. When I became a sales leader I thought it was my job to be the best seller on the team. I would swoop in to save deals, and ride along with sellers to close deals. Always being the hero. We did well, but not exceptionally well. It was only after I learned that my job was to coach each individual to be better than me that our sales really accelerated! A sales manager’s job is not to be the best seller on the team. It’s to curate excellence and leverage it amongst the team members.”
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9. To offer one specific suggestion that would trigger all the other actions
Shari Levitin – CEO and Professional Speaker at Levitin Group and Author of Heart and Sell
“Three Rules for Giving Feedback:
Tell your salespeople what they did right. A Harvard Business review study confirms that individuals who receive at least a 6-1 ratio of positive-to-negative advice outperform those more often criticized. Focus on a maximum of three improvements at a time. The brain can’t possibly remember 36 new techniques to incorporate into a sales presentation. Like golf, a good swing coach offers just one suggestion that triggers all the other actions. Feedback must be specific. Avoid generic suggestions like, build more trust or tell better stories. Instead share the four components of building trust or five keys to a powerful story. “
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10. That there is a difference between being busy and being productive
Kelvin Shaw – Executive Sales recruiter at Peak Sales Recruiting and former President of Stimulus Strategies Networking
“If there is one thing that I know now that I didn’t know then, it’s the importance of time management and prioritizing tasks. As a young business owner or professional, you will have many moving parts and daily tasks which can easily keep you busy. However, there is a major difference between being busy and being productive! In my opinion, the “Eisenhower Principle” is a must have time management principle that should be learnt and adopted by every business owner and professional. In essence, it is understanding the difference between urgent and important activities to help you think and structure your business priorities correctly.”
11. The value of really getting to know each person on the team well
Aaron Ross – Author of From Impossible to Inevitable and Predictable Revenue, and Co-Founder of Predictable University and Predictable Revenue
“I wish I knew the value of really getting to know each person on the team well, especially personally. When I did, it made it much easier to help that person overcome a problem or set better goals – whether personal and professional – to keep them motivated. Especially once they ‘got good’ at their jobs, it’s easy to get comfortable and go on ‘autopilot’ as a manager.”
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12. To take the time to help my sales reps focus on high-value sales activities
Janice Mars – President and Founder of SalesLatitude
“Many salespeople spend their precious time on the wrong things. Sales Managers and leaders play a crucial role in helping their reps focus on high-value sales activities. Here are three tips: Guide them towards activities that benefit customers the most. The bigger the problems reps can solve, the more resources, time and money customers will commit. Ask reps what they need to do their jobs better. Knock down any obstacles that make it difficult for reps to sell and customers to buy. Limit business hours to high-value sales activities. Train reps to save travel and administrative work for “non-working” hours.”
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13. That there is a big difference between demanding results and putting the right people in the right roles
Paul Howard – Chief Revenue Officer at Nectar Desk
“This is easy for me …. firstly COACHING 2.0. As a 2.0 manager, learning that there is a big difference between demanding results and putting the right people in the right roles and conditions for success is crucial. Lastly DOGS versus STARS. If you spend 50% of your time with your ‘stars’ – who are often independent by nature – instead of the ‘dogs’, you will double your results. Apologies to ‘dogs’ but they always have an excuse, lots of personal issues, etc. Once they are past a reasonable training time they will vacuum up all your time and energy. Go with the stars who are building a joint path for their career development and success!”
14. To trust myself and not suffer from “Impostor Syndrome”
Jane Gentry – Principal of Jane Gentry & Company
“I wish I had known to trust myself. Many of the leaders I coach now have the same syndrome that I had – Imposter Syndrome – the fear that the world will find out that I really don’t know anything. The truth is that I did/do know a lot and you do too. It’s those who think they know everything who are circumspect. It is OK to be authentic and a little vulnerable; it engenders trust. And, a team who trusts you will follow you into the unknown where you’ll likely create great things together.”
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15. People don’t care what you know until they know you care
Steven Rosen – Executive Coach at STAR Results and Author of 52 Sales Management Tips
“The one thing I wish I knew before becoming a Sales Manager was that when it comes to managing people, people don’t care what you know until they know you care. I have coached many new sales leaders to get to know their salespeople before they begin talking business or trying to tell them what they would do.”
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16. How to find simplicity in leading a sales force
Jason Jordan – Partner at Vantage Point Performance
“I perceived that sales leadership was a very complex task, so I tried to explore and navigate every possible course of action. In reality, leading a sales force is all about finding simplicity. Identify the few things that really drive sales performance, and then hammer those things hard from every possible angle. If you wade into the complexities of sales leadership, you’ll drown.”
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17. To understand that the separation between the ideology of church and state is a real thing as a manager
Morgan Ingram – Manager of Sales Development at Terminus and Host of The SDR Chronicles
“I wish I knew that I had to understand that the separation between the ideology of church and state is a real thing as a manager. When I was an SDR, I developed friendships with people on the SDR team and when I became a manager everything had to change. You have to realize as a manager that once you come into work, it’s like you putting on your jersey during a game and your reps cannot be seen as your friends when you have to put your manager hat on.”
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18. To design an informative and actionable sales process
George Brontén – Founder and CEO of Membrain
“The first time I built a sales team I made 3 faulty assumptions that almost cost me my company: 1) I assumed that salespeople knew how to sell because they had sold something for someone else. 2) I assumed that salespeople have discipline and are disciplined. 3) I assumed that a CRM system would help us sell better as a team. My conclusion and advice: design an informative and actionable sales process that is easy for salespeople to learn and execute. Make it the vehicle for sales methodology, enablement content, performance tracking and coaching. Then improve it!”
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19. How to motivate salespeople on a deeper and more sustainable level
Steven Benson – Founder and CEO of Badger Maps Inc. and former Regional Sales Manager at Google
“Many Sales Managers make a mistake in assuming sales reps are coin operated, and that therefore the most important parts of motivating a sales team are the compensation plan’s size and structure. Although those are important, salespeople are much more complex, and there are things you can do to motivate them on a deeper and more sustainable level. Help your team understand the big picture. A sales rep should be able to connect the dollar they earn to the company’s ability to produce a better version of the product they’re selling. This can be more motivating than just the cash in their pocket alone.”
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20. How to be involved with my sales team without the fear of becoming a micro-manager
Kevin F. Davis – President & Founder of TopLine Leadership Inc. and author of The Sales Manager’s Guide to Greatness: 10 Essential Strategies for Leading Your Team to the Top.
“When I was a sales rep, I once worked for a micro-manager—and hated it! I resolved never to be that way myself if became a sales manager. Years later, as a Sales Manager, I got confidential feedback from my sales team about my management style. Sure enough, the overwhelming perception was “Hey, Kevin’s not involved enough in our opportunities and our coaching. I realized then that I had over-corrected. And because I did little coaching, I wasn’t helping my team develop. Though I’d had the job title “Sales Manager” for over three years at that point, that was the moment I truly became a Sales Manager.”
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21. How to manage my time and prioritize my tasks
Bridget Gleason – Vice President of Sales at Logz.io
“Your time is not your own! I’m not sure what I was expecting when I first moved from an individual contributor to a Sales Manager, but I was surprised at how much time was required to manage and lead a team. My calendar was suddenly full of meetings, 1:1’s, customer calls and coaching sessions. And for a while I felt a bit out of control. One skill I had to work on was time management and prioritization. Sometimes I miss the days when my time was truly my own, but I wouldn’t trade the privilege of working with a team for any amount of hours back in my day.”
22. To understand the uniqueness of each person on my team
Sam Capra – VP Sales at flexReceipts
“One Size Does NOT Fit All. You need to understand the uniqueness of each individual on your team. It sounds obvious, but as a young leader you try and apply a one size fits all approach. The key is to take the time to know what motivates each member of your sales team and what demotivates them. Having this understanding means you can play to their strengths. This allows you to adapt your coaching, training and feedback in a manner that gets results.”
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23. To coach each salesperson in the way they learn, process, speak and execute actions
Alice Kemper – President of Sales Training Werks
“It was one thing to be 100% responsible for achieving my numbers as a rep and totally foreign to achieve my new numbers through 20 people as the manager. My first biggest “ah-ha” was they didn’t sell how I did, think like I did, have the same goals or methodologies and they were certainly not interested in hearing how I did it. Because of my teaching background I immediately realized I needed to coach each person to be the best that they could be in the way they learn, process, speak and execute actions. A few months of building a great team could have been shaved off if I had known coaching was the key before day one.”
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24. To treat my sales team like I treat my customers
Nancy Bleeke – President and CSO at Sales Pro Insider
“To lead your sales team to perform, treat them like you treat your customers! For customers – you make the time when they need it, lead them to the best outcome, explain everything relevant to them, offer information, solutions, tools, and resources relevant for THEM, and make it easy for them to work with you. It’s the same for your team. Get them what they need to succeed (it’s not just leads and software), make the time to coach, and make everything you say, do, ask, and expect focused on what makes it important to them. You’ll be an effective leader with a performing team.”
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25. How I need to make sales reps lives easier
Michael Seymour – Senior Director, Sales Enablement/PMO at Oracle
“What I wish I learned earlier in my career is how you need to make a sales rep’s life simpler. Selling, especially in B2B, is a tough job. Navigating byzantine internal bureaucracies while at the same time maneuvering complex customer buying processes is challenging. If you absorb as much of that complexity as possible, it makes it much easier for sales reps to close business. Whenever possible simplify processes, products, messaging and asset distribution to enable a rep to focus on selling.”
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26. That sales comp plans must align with the results the company wants to achieve
Ann Davis – VP of Sales at Journey Sales
“Anyone with a career in sales has heard the stereotypes that salespeople are coin operated and competitive. Understanding that there is definitely truth to these, I have always paid close attention to how sales people are being paid because it is directly tied to what they will actually do. Therefore, sales comp plans MUST be aligned to the results the company wants to achieve. As an old boss/mentor of mine once told me, they must be simple enough to pass the spouse test. So any spouse that looked at it would instantly understand how their spouse is being paid. In regards to competition, mostly all sales reps use it appropriately as a little bit of healthy competition, which never hurt anyone and can be just added driver to achieve greater results.”
27. To be involved in the recruiting process
Nick van der Kolk – Head of Enterprise HubSpot & Founder of HubSterdam
“Recruiting is hard, not only because it is a totally different skill set and process than sales. It also requires an even bigger focus on a long term mindset. On top of that, your legacy as a manager won’t be the number you hit but who and how you developed the team. I would have spent far more time being involved in the recruiting process prior to being a hiring manager myself.”
28. To use programs to set up sales contests and broadcast sales results frequently
Emily LaRusch – Founder and CEO at Back Office Betties
“One of the things I wish I’d done earlier is use a program like Zoho Motivator. It plugs into our CRM so it’s always up to date and makes it easy to give the sales team daily contest results and tie 1st place to a prize. I have always communicated targets but never publically broadcast results with regularity or frequency. With Zoho Motivator, I set up the contest in the beginning of the month and it runs on autopilot. I think good sales people tend to be competitive and seeing team member results regularly will either light a fire under someone driven or highlight the duds on the team.”
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29. There’s a difference between being updated on a project and hovering over your employees
Vladimir Gendelman — Founder and CEO of CompanyFolders
“Of course you want to stay on top of everything, but there’s a different between being updated on a project and hovering over your employees. When you micromanage, your sales team feels smothered and unappreciated. Instead, give your employees ownership of their work to let their talents shine. Productivity will improve dramatically.”
Put these 28 tips to use and visit the Peak Sales Career Blog for the latest actionable insights on how to advance your sales career.
Eliot received his B. Comm. from Carleton University and has been honored as a Top 40 Under 40 Award winner.
He co-authored Sales Recruiting 2.0, How to Find Top Performing Sales People, Fast and provides regular insights on sales team management and hiring on the Peak Sales Recruiting Blog.
Latest posts by Eliot Burdett (see all)
- How To Make Progress On Your Sales Goal Without A Sales Leader - September 15, 2021
- Augment Your Recruiting Strategy During “The Great Resignation” - July 26, 2021
- London Sales Recruiters: 3 Recruitment Insights & Trends - August 5, 2020