The 34 best sales management articles of 2021 for startups & SMBs

The 34 best sales management articles of 2021 for startups & SMBs

The role of the sales manager has shifted and transformed at a faster pace in the past two years than ever before. At the same time, some fundamentals remain true: Like Peter Drucker's famous adage that management is doing things right, and leadership is doing the right things.


The best sales managers are great leaders, and what you'll find here is practical, actionable and honest management advice. The result of many years working on the frontlines of sales.

I personally don't consider myself a good sales manager. I'm a natural born sales person and leader. I've always had charisma—but it's those same qualities that also caused me to seriously struggle when I managed teams. I once had to fire half of my team. I knew all of these people, I cared for them, in fact for most of them, it was me who had brought them on board.

I've made more mistakes than I could blog about, and if you're reading this, you might now that I blogged a lot: I've published thousands of pieces of sales advice over the past 10 years, coached and advised more sales teams than I care to count, and spoken on sales at events all over the world.

All of this is just to say: I hope that my painful sales management mistakes will be of value to you. And that you'll do what smart people do: learn from them, without having to commit them yourself

New & aspiring sales managers: Advice for success

You've just been promoted to the role of sales manager. Or maybe you're not even there yet, but have your eyes set firmly on the goal. Here's some advice to help you get there, and start out strong.

7 key skills you’ll need to become a sales manager

Reading time: 20 minutes

This article breaks down the most important skills every sales manager should have to effectively lead their team.

  1. Identifying, recruiting and hiring talented sales reps
  2. Leadership
  3. Managing, motivating, incentivizing and empowering your sales team
  4. Ability to train, coach and mentor
  5. Defining, implementing (and innovating) sales plans
  6. Organizational skills
  7. Forecasting sales results (within a reasonable margin of error)

For each of these points, you'll find the most crucial high-level concepts, and references to more in-depth material if you want to deep dive on any of these subjects. Warning: This is a loong read.

10 most common mistakes new sales managers make

Reading time: 9 minutes

I've coached hundreds of new sales managers and identified common stumbling blocks to adopting to their new role. The most common one is "what got you here will get you there" kind of thinking—which makes total sense when you think about it. Most sales managers got promoted because they were able to deliver results. Becoming a successful sales manager requires a complete reorientation of focus and activities, and that's never easy, especially if you're not equipped with an already proven management playbook.

How to succeed in your new sales manager role

Reading time: 4 minutes

Whether you're a freshly minted or experienced sales manager—when you step into the role with a new team, the first few weeks are always crucial. In this quick read, you'll learn more about 4 key things you need to get right from the: Setting clear expectations, building trust and credibility, motivating your team, and keeping the big picture in mind.

How to lead a sales team without micromanaging everyone

Reading time: 5 minutes

Especially early on in your sales career, the urge to micromanage can be strong. You lack the experience and confidence in your own sales management skills, but you feel the full burden of responsibilities on your shoulders. Often, it's the sales managers that care the most that turn into obsessive control freaks. On the other hand, you don't want to just let your reps do their own thing either. This article will show you how to find the right balance, and recognize when you need to step in, and when you need to get out of the way.

3 sales team structures for building a high-performing sales organization

Reading time: 10 minutes

There are different ways of structuring your sales team, and it's worth experimenting with all of them to figure out which works best for you. Understand what the core DNA of your sales team is, and what you're trying to create.

Hiring, recruiting, and onboarding: Assembling the dream team

Getting the right sales talent to join your sales organization is an art in itself. What's more—it's constantly evolving. Top candidates expect a top hiring process. Realize that even if a candidate interviews for a job, it's a two-way street: It's not just them applying for a job. It's also you applying for them to dedicate their time and talent to the mission of your company. Both of you are mutually exploring whether this is the right fit, so having a solid sales hiring strategy in place is crucial.

The 4 key stages of sales hiring for startup founders

Reading time: 10 minutes

If you're building an early-stage sales team, there are four stages of sales hiring, and each of them requires you to adapt your sales hiring approach, and evolve your sales strategy. Find out when it's time to hire a senior sales leader, how much you yourself should be involved in the sales process, and advice on finding the right candidates.

Top 10 interview questions in sales hiring

Reading time: 7 minutes

How do you conduct an effective sales job interview? What questions do you ask? How do you evaluate the answers prospective employees give you? There's no magic question that'll with absolute certainty indicate whether an applicant would be a good fit for the role you're trying to fill or not, but knowing how to spot certain red flags and identify strong positive signals will help you hire more effectively.

How to offboard a sales rep the right way

Reading time: 8 minutes

You will part ways with some of your salespeople. Some of them will be great people that you wish would stay, but they simply have better opportunities or their priorities shifted. Some of them will be people that just didn't perform or caused problems, and you're the one firing them. Either way, offboarding a rep well is an under-appreciated skill.

The scrappy startup way to design a first sales commission structure

Reading time: 4 minutes

I share a very simple, basic framework for designing an initial sales compensation plan for your early-stage sales team. Most sales managers overthink this and spend too much time trying to come up with the perfect plan, when the key at this point really is to move fast, learn, and iterate.

Sales meetings: Make them count

There's nothing that kills a sales team's buzz more than time-wasting meetings. On the other hand, there's nothing as impactful to motivate and align your team. I've always had a very no-nonsense approach to meetings: Fewer meetings, higher impact.

Should you really have this sales meeting? 5 questions to ask yourself

Reading time: 6 minutes

47% of employees think meetings are the biggest waste of time in their business. And if there's one thing sales reps in particular have very low tolerance for, it's time wasting. Because they could be making calls, reaching out, following up, and bringing it in. Don't make them sit through pointless meetings. Most sales managers can radically cut down the amount of meeting hours.

3 questions that’ll help you conduct more effective sales meetings

Reading time: 6 minutes

Once you've determined that a meeting is actually worth having, it's time to be very deliberate about designing it well. What's the purpose of this meeting? Is it a general sync-up to get everyone on the same page? Is it a strategic session to make sure everyone understands the direction of your team? Is it about motivating your salespeople? Are you trying to resolve a specific issue or address a particular challenge? Are you going to review your metrics?

How to run the perfect sales pipeline review meeting

Reading time: 7 minutes

This collection of sales management articles wouldn't be complete without an article on effective pipeline reviews. I've screwed them up myself often enough, and I've witnessed too many bad ones. And it's a shame, because when done right, they'll help your team close more deals.

The winning sales huddle: 10 ways to amp up your team

Reading time: 13 minutes

Many sales managers conflate sales huddles with sales meetings. Don't do that. Remember the golden rule of the sales huddle: Keep it short and sweet. Find out how to conduct impactful sales huddles that your reps actually want to join, and that'll boost sales performance.

12 sales kickoff meeting strategies and best practices for bringing your team together

Reading time: 15 minutes

A sales kickoff is typically a multi-day event where you bring your entire sales team together, share best practices, and talk about your sales goals and strategy. During a sales kickoff, your reps don't actually do any selling, aren't handling any of their usual day-to-day tasks. It's all about focusing intensely on getting everyone in the right mindset for the months laying ahead.

Training and coaching: Upgrade your reps

If your reps feel like they're learning, professionally progressing and growing, and consistently acquiring new skills, they'll not just create bigger wins for you, but also stay with you longer.

Top sales talent is constantly being headhunted, and no matter what you pay—eventually there will be an employer with deeper pockets than yours that can afford a much higher salary than you can. If the only reason they're staying with you is a paycheck and EOY bonus, you'll see your best reps leave. But as long as they feel they're progressing professionally, they'll often stay with you, despite financially better offers they might receive otherwise.

In this session, you'll find advice on high-impact sales coaching and effective training frameworks for your team.

Ultimate guide to sales coaching: strategies, tips & tools to win

Reading time: 13 minutes

60% of sales reps are more likely to quit if their manager is a bad coach. (And that number is probably even higher in the current climate of 2021, when the competition for top talent is at an all-time-high.) Companies that have a formal coaching program increase win rates by 28%. If you don't yet have effective sales coaching in place, start here.

25 expert sales coaching tips and techniques to amplify close rates

Reading time: 17 minutes

Looking for actionable and specific tips to include in your sales coaching repertoire? You'll find advice on allocating your sales coaching resources, using pipeline data to spot high-impact coaching opportunities, tie team objective to individual mission goals, impart a sense of ownership to your salespeople, positioning negative feedback effectively, and much more.

Top 15 sales coaching platforms to develop a high-performing team

Reading time: 10 minutes

If you really want to level up your sales coaching game, you'll have to invest in some tools. Learn more about some of the best tools for call coaching, conversation intelligence, and coaching strategy.

Quota-boosting sales coaching template

Reading time: 15 minutes

Implementing an effective sales coaching program isn't easy—that's why we've created a ready-to-use sales coaching template for you, and shared 5 more sales coaching models for you to model your own efforts after. In no time, you'll have an action plan to get your teams hitting consistent home runs!

12 sales training techniques to build an unstoppable sales team

Reading time: 19 minutes

Sales leaders are responsible for giving their reps the knowhow and skills they need to excel in their role. You'll have to asses your team's strengths and weaknesses accurately and choose the right format for your training: Should you conduct workshops? Offer self-study courses? Hire outside sales training consultants? Have your reps attend conferences?

Crisis management: Dealing with hard things

Sometimes, things get tough. Maybe a competing vendor is eating into your market share with an aggressive offer. Maybe your potential customers are affected by the pandemic and just aren't buying. Maybe that new marketing strategy your company bet on last quarter is not working out as planned.

Whatever the reason: Your sales team is not hitting their numbers, your reps are doubting your approach, and the CXOs are putting pressure on you to produce. Managing in a crisis

How to turn a struggling sales team around

Reading time: 15 minutes

Managing a high-flying team is a fun challenge. But if your team is struggling? Ugh. Completely different story. In this in-depth guide, I share what it takes to lift a failing sales team to success. From identifying the causes of failure, to building a plan for turning it around, and keys to executing and adapting that plan when all those inevitable Bambi meets Godzilla moments will occur.

How to inspire change from within

Reading time: 7 minutes

Your team's numbers are down, as is their morale. You came up with a new sales strategy, but as you announce it, you're met with blank stares. Your team isn't on board with the plan. In this article, I share how he transparently communicated the how and why of a new plan, how he led by example, and relentlessly measured and iterated his approach.

Toxic sales culture? Here’s what happened and what to do about it

Reading time: 7 minutes

I'm a big believer in fostering friendly competition among sales reps. But if things become antagonistic, it's time for you to step in and own the problem. Identify what led to the current situation, and assess your current team. You might find that you have to fire some of your team members—if that's the case, the sooner you do it, the better. The worst thing you can do is to keep bad-fit employees, hoping that eventually things will get better and resolve themselves.

CRM best practices: Make your reps (actually) want to use the CRM

There's a clear shift in the CRM software: More user-friendly CRMs that actually empower sales reps to do their jobs better, versus older customer relationship management legacy systems that mostly added to the workload of reps.

Because old systems were cumbersome to use, and build first and foremost to cater to the needs of VPs, directors and CXOs who wanted to have data and reports at their fingertips, sales managers had to come up with all kinds of measure to encourage CRM compliance.

Modern CRMs instead do it differently: They replace manual data entry with automatic logging of sales activities. They provide a unified workspace for sales reps, so they don't have to switch between different apps for their sales activities: calling, emailing, reporting, follow ups and more all in one. This streamlines workflows and improves rep productivity.

CRM best practices: Your implementation strategy for 2021 and beyond

Reading time: 6 minutes

Sometimes the best way to improve your CRM workflows is to just implement a new one. It's key that you do this well from the get-go. I see too many teams rush into a new CRM implementation with bad data. They could have spent 3 hours cleaning up their data before moving to a new CRM. Instead, they'll later spend 2 weeks trying to remedy the bad data from within the CRM after they've already implemented it.

What’s the best Salesforce alternative? Why (most) startups should NOT use Salesforce

Reading time: 12 minutes

Salesforce is the de facto leader in the CRM space, and one of the most common questions I get is: "What do you think, should we use Salesforce?" The short answer to this question is hell no and this article dives deep into the "why".

Sales operations: A smooth running machine

Choosing the right tools, keeping track of the numbers, preparing effective sales reports, and giving your team the sales automation tools that allow them to better leverage their time are all part of the sales ops role. If your sales reps are James Bond, your sales ops team is Q.

The only kick-ass guide to sales operations you'll ever need

Reading time: 25 minutes

How do you structure a sales ops team, and define a strategy? In this guide, you'll get a practical guide for getting started with sales ops, learn about best practices, and find out which framework and processes are best suited for you. In addition to that, you'll learn about different tools you can choose for your ops stack.

The founder’s guide to sales operations

Reading time: 5 minutes

If you're not ready to hire a full-time sales ops person yet, this guide is for you. It lays out a practical approach to building out a basic sales ops function that you can run yourself, even by just allocating a bit of time each week. The key is to start with simple experimentation, and a clear-eyed reading of the results.

What is sales tracking? 5 steps to track sales + templates & tools

Reading time: 15 minutes

Too many sales teams track their sales numbers with a "the more the merrier" mindset. But sales tracking is not about capturing as much data as possible. It's about capturing right right data accurately. Find out about the 6 types of sales tracking, and learn more about the 5-step process to track your sales numbers effectively, using the right tools for your team.

Sales dashboard templates, examples & KPIs for high-performing teams

Reading time: 29 minutes

How do you build out dashboards for your team? What tools do you use? Which KPIs make sense to track on a dashboard? All of these questions, and more, are answered in this article. In addition to that, you'll also see real-life sales dashboard examples, find downloadable templates, and learn about best practices for designing dashboards that drive learnings, insights, and ultimately revenue.

Sales metrics: Being on top of the numbers

Sales is a numbers game. To quote Peter Drucker for the second and final time in this piece, you can't manage what you can't measure. If you're in charge of measuring your team's performance, you'll have to not just acquire a deep understanding of the numbers, but also constantly keep your finger on the pulse of the metrics. There's no point in indiscriminately amassing data—instead, understand the story your numbers tell.

Which metrics should you track? A super simple framework

Reading time: 2 minutes

If you're "not a numbers person" then start here with your journey into the wonderful land of sales metrics. You'll find a very simple and pragmatic, yet effective framework for keeping track of your key sales metrics. In fact, if you're running a very early-stage sales team this is all you need to know about sales metrics.

18 essential sales KPIs: What to measure and how to track everything

Reading time: 33 minutes

You want to schedule some time in your calendar before you sit down and read this guide. You not only get a very in-depth guide covering all kinds of sales metrics for different kinds of sales organizations. You'll also get an actionable framework for deciding which metrics to track, how to measure them, and templates you can use to quickstart your sales tracking efforts.

Why sales pipeline metrics are meaningless—when numbers mislead salespeople

Reading time: 8 minutes

I've spoken to thousands of sales leaders from all kinds of companies, and one thing I learned is this: There's a lot of BS. People talk their numbers nice. The most dangerous kind of number BS is the one that you believe to be true yourself. It's better to face truth, even when it hurts. Keep your feet firmly planted on solid ground. It's not enough to look at metrics—it's important to understand the context of data, and be able to intelligently interpret what these numbers actually mean. That's what drives effective decision-making.

5 steps to setting sales goals that help you grow (quickly)

Reading time: 15 minutes

Make sure that your sales goals are challenging, but realistic. This will mean that you set a goal that a certain percentage of your reps will meet, a certain percentage will significantly exceed, and a certain percentage will miss. It's not a good thing if all your reps achieve their sales goals. That just means that you didn't set ambitious enough goals. In addition to that, you want to tie your team's goals to the larger companies goals, and reverse engineer from what they're trying to accomplish. You want to come up with a model that allows you to reverse engineer all the way to individual activity metrics.

Salespeople: Nothing else matters

Last but not least—it's all about the people on your team. It takes so much effort to recruit, hire, train and onboard the right people. Even from a purely financial point of view, it makes sense to invest into keeping your people happy and optimizing for employee retention. But more important than that: be a Mensch. Treat your people well. Go the extra-mile for them. Overdeliver, be a giver.

Managing startup teams: Parenthood, death, and other personal issues

Reading time: 5 minutes

The best sales leaders understand that their reps aren't just employees. They're human beings, people with a personal life. And sometimes events in their person lives can impact their work performance. The death of a loved one, sickness, becoming a parent—all of these and more will shake up your reps. Don't expect them to switch that part of their life off completely during the 8 hours a day they're working for you. Don't ask them to just robot through it—at least not if they're usually solid performers.

Radical candor for sales teams: How authenticity and transparency close more deals

Reading time: 23 minutes

Most sales professionals understand that authentic communication is key to building trust with their prospects. But candor matters even more in the context of team communication. Learn how to create a culture that allows everyone to openly speak their mind, share their concerns, and create internal bonds that withstand even the most challenging conversations.

Wrapping up

All of these sales management articles are only of value if you actually take action. Information in itself has no value unless you act on it. So ask yourself:

  • How can I apply this to my situation? What action can I take based on this?
  • How is this relevant to my challenges and opportunities?
  • How can I test whether this is true for me and my team?

Developing sales leadership is not an easy task. You will find that the hardest part is not the mental aspect. What makes managing sales teams hard is not tracking the metrics, mapping out the sales funnel, it's the emotional aspect. It's dealing the feelings within yourself and your reps when you miss quotas, when you underperform, when things don't seem to work.

If you don't just want to jump through all of these articles, and prefer a more structured experience, get your copy of my book The Sales Hiring Playbook. It's packed with actionable advice on hiring and managing top sales talent.

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