8 Sales Lessons from Michael Scott

May 17, 2021

Daniel Blaser

You can learn a lot from success, but you can learn even more from failure. No one embodies this truth like Michael Scott—the king of paper merchantry, the greatest manager Dunder Mifflin ever saw (or so he’d like to have you think).

“The Office” is one of the most beloved television comedies of the past 30 years, and its heroically bumbling hero Michael Scott, played by Steve Carell, is one of the most beloved sitcom characters in the same period. Buried among the laughs, dogged, hapless Michael actually has some tried-and-true sales wisdom to impart that can get your company purring like the Scranton branch. Analyzing his failures (and occasional successes) can improve your team’s approach to problem-solving, employee wellness, and organizational structure.

1. Embrace the Unorthodox Sales Script #

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Image Source: The Office

A great sales script is fundamental for any sales team, but there’s more to the art of selling than following the beats. Michael Scott knows this well. From landing deals via impersonations to using Pretzel Day as a sales opportunity, Michael is a master of unconventional selling.

One of the best examples of Michael’s commitment to unorthodox selling is from the episode “The Client.” In it, Michael and Jan meet with Christian. Christian is a key prospect—getting him on board will not only be a great win for the team, but it will also potentially save jobs at Dunder Mifflin. Having originally arranged to meet in a hotel room, Michael astonishes Jan by taking Christian to Chili’s. Jan then watches while Michael completely ignores the sales pitch she wrote. But, this breach of protocol ends up landing them the deal.

The takeaway #

Your reps shouldn’t be married to your sales script. Your sales script is primarily there to give your rep the best opportunity to showcase two skills: storytelling and empathy. It’s these qualities that really win deals.

That’s because storytelling and empathy put your prospect center stage. Successful sales can tell your prospect’s story through your product. Sometimes going off-road with your storytelling can work wonders to this end. Your script may call for plenty of well-deployed statistics, case studies, or social proof of your product’s worth. But if your reps’ intuition tells them that the deal might be better served by telling that great story about how your product helped save a cat in a tree/helped your colleagues get married, let them follow that hunch.

That warmth, familiarity, and narrative flair might just be the deal-making factor.

2. Build Rapport #

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Image Source: The Office

When it comes to solid (if unusually packaged) sales wisdom, “The Client” is an episode that keeps on giving. It shows us that the secret to Michael’s success as a salesperson is the emphasis he puts on the “relationship” component of “business relationship.”

It’s a simple fact that people work with people they like—and while brilliant statistics and client testimonials make you credible, they can’t make your prospect like you. There’s no better way to build the foundations for a successful business relationship than by establishing a personal connection that establishes your rep’s own likeability.

The takeaway #

Your reps should always look to ease into a call with a few minutes of small talk. The subject is hardly important. It could be a previous company or a co-worker they and the prospect have in common, or a current event everyone’s talking about.

Once that initial “Hello” has been taken care of, your reps should focus on listening to what your prospect needs and mirroring that need back to them. These subtle cues show that your rep is listening and cares about helping your prospect solve their issues through your product.

3. Do Not Follow the Chart #

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Image Source: The Office

We said earlier on that sometimes you have to learn from people’s mistakes—and Michael Scott makes a whole lot of them. He makes a lot of slip-ups just so you and your sales team don’t have to.

In fact, if we’re feeling uncharitable, we could say that Michael Scott’s whole management style is something of a mistake. Think back to Jim Halpert’s chart of Michael’s priorities in management: 80% distracting others, 19% procrastinating. That leaves just a solitary 1% for critical thinking (and even that might be generous).

Nevertheless, there are truisms in the chart that will resonate with a lot of sales managers. It can be tempting to micromanage a team’s activities, even though this can end up being more distracting than constructive. Faced with tough calls, it can be just as tempting to procrastinate. So, take measures to prevent your managerial chart from looking like Michael’s.

The Takeaway #

Create structured time for both concerted work and rest—the clear separation will reduce the temptation to procrastinate. This is especially important in the era of remote working, as distributed teams often work longer days.

In these days of Zoom fatigue, every sales manager should avoid scheduling too many meetings. Michael’s endless parade of meetings and micromanaged decision-making is more distracting than it is constructive for his team. Instead, post-meeting agendas ahead of time so that all concerned know what a meeting will cover. If context switching is becoming a bugbear for your team, help your team shape their calendars to minimize it.

Be disciplined with your timings—if you’re consistently running overtime, amend your scheduling. Create tracking plans and use well-integrated CRMs to centralize your team’s access to resources, to reduce the amount of time you need to spend fetching data for your team.

4. Focus on Team Development and Wellness #

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Image Source: The Office

One of Michael’s more endearing qualities is his determination to make Dunder Mifflin feel like one big family. In fact, he often seems more concerned with throwing birthday parties and building a friendly, zany atmosphere among his team than he is with getting them selling to their potential. As ever, though, there’s a method somewhere in the madness.

As a manager, having friendly relationships with your team is key to securing wellness. More and more professionals expect employee wellness to be one of their employer’s priorities, and the best foundation of wellness is strong manager/team-member bonds. Building wellness can be as simple as taking an interest in your team members’ interests. Remember when Pam Beesly held her gallery opening and Michael was her only colleague to attend? And the only one to express his sincere appreciation? You can bet it’s a show of empathy and support Pam never forgot.

And Pam is not the exception. At one time or another, Michael came through for them all: Jim, Dwight, Holly, Oscar, Kelly, Angela, Ryan Howard, Meredith, Erin, basically everyone except Toby Flenderson (and maybe Phyllis; oh, and Stanley). That is, when he wasn’t offending them with problematic language or, in Meredith’s case, hitting them with his car.

The Takeaway #

All successful sales managers welcome personal dimensions within the professional relationships they have with their reports. The same rapport-building logic that top sales reps use can be put to use in building relationships with your team members. You don’t have to be a best friend—just a human being. Between the deal reviews and coaching one-on-ones, always make time to just shoot the breeze and chat. This builds trust, and employees are more likely to be candid in expressing themselves and their wellness needs to managers they trust.

Building relationships with your team is also vital for understanding what motivates your team members. Sure, you can motivate your team with a bump in their commission or added paid time off or a free pretzel. But let’s say you have a sales rep who takes care of an ailing parent and has a 100-mile round trip to visit them three times per week. A more obliging schedule, a family health insurance plan amendment, even a restructured four-day work week, might give them a bigger motivational lift than all the bonuses in the world.

You’ll only find out about these kinds of personal wellness and motivational needs if you get to know your team members. And if you manage to avoid hitting any of them with your car.

5. Make Learning a Priority #

Michael probably likes to think of himself as a bit of a Renaissance man—scriptwriter, parody songwriter, basketball player. His interests can be a little eccentric, but his curiosity and willingness to learn are actually his greatest assets.

We have it on record from some of the industry’s top sales leads that curiosity and willingness to learn are common traits of all successful salespeople. Avid learning helps salespeople stay abreast of developments in their industry. A wide range of interests gives a salesperson a greater variety of means to form a rapport with prospects from different walks of life. It even equips a salesperson with more approaches to problem-solving.

The Takeaway #

Create activities that encourage your team members to immerse themselves in mind-enriching pursuits. Invite one rep per week to present a show-and-tell on a subject they’re passionate about at your weekly meeting. Combine the same activity with your sales coaching problem by having your reps “sell” their subject. Incentivize your reps to spend a portion of their time at work just reading and posting interesting facts they come across in group Slack channels. Encourage every Oscar in your office—there’s no such thing as a know-it-all!

We learn best when we are relaxed. Factoring that time into your reps’ schedules is great for breaking up busy days—and your team will come out of it not just refreshed but having learned something, too.

6. Accept Responsibility #

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Image Source: The Office

Michael is famed in Dunder Mifflin for scapegoating his teammates when things go wrong. Outside the confines of an NBC sitcom, this is no laughing matter. Not only does that lack of accountability create problems for his team members, but it stops Michael from growing.

People avoid responsibility when they’re afraid that mistakes will bring punishment—that they’ll lose their job, their commission, or their reputation on the team. It’s this kind of fear that brings your whole team culture down.

The Takeaway #

The key to avoiding a scapegoating culture is creating an environment where sales reps are encouraged to try and fail. Removing the stigma around making mistakes will empower your reps and foster a culture of accountability.

When a rep does make a mistake, review it together without judgment and, if necessary, add to their coaching plan. If you as a sales manager have made a mistake—neglecting a team member’s needs, making the wrong call when approaching a key prospect—then own it, and publicly. This will help retain the trust of your team. Mistakes can often be fixed easily enough, but once trust has been damaged, it can take a long time for it to recover.

Accepting responsibility is not just about taking the rap for mistakes, either. As a sales manager, you have a certain responsibility for helping your reports achieve their professional development goals. Michael is no good at this—he even sabotages Jim’s bid for manager because he thought it would jeopardize Michael’s own job. But the likelihood is that had Michael encouraged Jim in his ambitions, the whole department would’ve benefitted. Remember that your team members’ ambitions are yours, too, and when you help them reach their goals everyone wins.

7. Do Not Skip Dundies Night #

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Image Source: The Office

Michael decided to hold an awards ceremony for his office, “The Dundies”—it was one of the best managerial decisions he ever made. Do not let the objections of Michael’s fusty superiors in New York convince you otherwise.

Why was Dundies such a great idea? Because it provided an opportunity to celebrate great work by the team. It’s easy for key sales work to be taken for granted or forgotten in favor of a focus on what’s next. But there’s no greater motivator than recognition.

The Takeaway #

In this case, the takeaway is simple: Be like Michael (no, really). Take the time to hold your own sales team awards ceremony aimed at honoring your team members’ efforts.

Awards are great for reinforcing great sales behavior and offering public recognition for your reps’ effort and sacrifice.

Create a little statuette and hand out yearly performance bonuses to reward reps for achievements like:

  • Most New Business
  • Most Resurrections
  • Most Upsells
  • Most Enterprise Customers
  • Most Improved Rep

Don’t just hand out awards from on high, either. Encourage your team to nominate their co-workers for prizes. Who has displayed the best team spirit? Who was willing to take the time to coach younger reps and guide them through those stressful early weeks? Who spotted an issue plaguing your whole pipeline and got your pipeline velocity back up again? The more diverse an array of behaviors you reward, the more good behaviors your team will begin to model.

8. Know Your Strengths #

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Image Source: The Office

One truth about Michael Scott remains buried underneath the gags: He’s not incompetent—he’s just in the wrong place.

Even longtime viewers of the series might scoff at the idea, but look closer and you’ll see it’s true. Michael is demonstrably a fantastic salesperson. He’s creative, empathetic, and able to coax closed-won deals out of unlikely situations. However, the skills that make him a great salesperson do not necessarily make him a great manager. The same things that make him great at selling—his measuredness, his empathy, and his desire to be liked—get in the way when he’s trying to manage.

The Takeaway #

Management roles often seem like a natural pathway to reward excellence, but the key to success is knowing where you (or, for sales managers, your salespeople) can best make an impact. Use your personal connections as a manager to determine if your rep is right for a management role. Do they have the ability to juggle a wide variety of reports as well as their personal work? Are they empathetic? Can they do the work of motivating and looking after the wellness of your reports? Are they self-aware?

In other words, are they NOT like Dwight Schrute?

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Image Source: The Office

If you determine that your star rep is doing a great job, but not suited to management (or that they’re too important to the sales team to let go just now), then get creative. Develop novel compensation and motivation plans for reps who want to stay on in frontline sales. Make sure their pay rises competitively with what they could be making in management, or offer them a pick of the perks (company car? More PTO?).

Michael Scott: Not the Regional Manager We Deserve, But the One We Need #

Michael Scott’s sales and sales management approaches are to scorn convention and treat his staff like family. Follow his example to the letter and much hilarity will ensue. But it probably will spell curtains for your sales department (even if you do get a “World’s Best Boss” mug for your trouble).

Instead, look to emulate Michael’s quirky style in a disciplined manner. When done right, Michael’s style can be great for bringing more empathy to your sales process while increasing team spirit and wellness, whether you’re running a paper company or a fintech startup.

Just don’t say, “That’s what she said.”

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