Radical Candor for Sales Teams: How Authenticity and Transparency Close More Deals

It’s an understatement to say that salespeople don’t have the best track record regarding trust. For the average person, we’re sleazeballs who will say anything to close a sale.

But the best reps know that real, long-term success doesn’t come from pushy persuasion or verbal acrobatics but from the exact opposite: Candor, honesty, and vulnerability.

That’s because sales are all about change. When you ask someone to buy your product or service, you ask them to change their workflows, habits, and business.

Yet humans hate change. We’re skeptical and cynical when anything threatens our ‘normal’ way of doing things. But to succeed in sales, you must build trust and clear a path toward change in your prospects and teammates.

You need Radical Candor.

Radical Candor is a tool that helps you quickly build meaningful and trusting relationships with your team and prospects. With Radical Candor, you can break through the BS of sales stereotypes, empower your team to do their best work and turn first-time buyers into lifelong customers.

Whether you’re trying to get over the objections of a hesitant prospect or give honest guidance to a stubborn member of your sales team, Radical Candor is a superpower for sales teams.

So, how can you make Radical Candor a part of your sales strategies and team culture?

The Basics of Radical Candor for Sales Teams

The term “Radical Candor” comes from management consultant Kim Scott, who describes how the best managers build authentic relationships and lead their teams.

After working with leaders at companies like Google, Apple, Dropbox, and Twitter, Scott realized that the difference between high-performing teams and everyone else was their intense focus on guidance.

But these managers did more than just impart wisdom to their reports. They used specific techniques to build authentic relationships with their teams, where feedback—both praise and criticism—flowed freely and openly.

Think of the famous quote from Apple founder Steve Jobs:

It doesn’t make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do.

This sort of “Radical Candor” doesn’t happen by chance. Instead, it requires a culture where everyone on your team feels respected, heard, and empowered.

As Scott describes in her book Radical Candor: Be a Kickass Boss Without Losing Your Humanity, this requires two key elements:

1. Caring Personally. Scott calls this “giving a damn.” Instead of “keeping it professional,” Radical Candor means wholly investing in whomever you’re working with—your sales team, a new prospect, or a long-time customer. Caring personally isn’t about getting all up in someone’s business. It’s about making the time to build an authentic, real, and human relationship with them.
2. Challenging Directly. Scott calls this “being willing to piss some people off.” The best relationships are built on the understanding that you won’t always see eye-to-eye. But that you trust each other enough to tell the truth. Challenging directly isn’t about talking down to people, yelling, or thinking you’re always right, but being critical in good faith and not letting power dynamics get in the way of doing your best work. In the early days at Close, we had weekly co-founder dinners where we would explicitly ask each other, "Is there anything I did that pissed you off?". By creating space for voicing these things between us in the early days, we later scaled this culture of candidly asking for and sharing when someone on the team did something that made someone else feel bad.

When you combine these two elements, you end up with an approach that fast-tracks relationship-building, instills trust from the outset, and allows people to open up, be vulnerable, and make real, meaningful changes to their work.

(We told you it was a superpower!)

How Does Radical Candor Help Sales Teams?

You’re probably thinking, “Radical Candor sounds great for managers. But how does it help me in sales?”

Even though Radical Candor was developed for management, every member of your sales team can benefit from learning how to build stronger, more authentic relationships.

Let’s start with the most obvious use case: Sales managers.

As the leader of a high-performing sales team, the more open your team is to guidance—praise and criticism—the more they’ll trust what you’re saying and work to be the best they can be.

Even better, when your team knows they can be radically candid with you, they’ll be more open to giving feedback, suggesting new sales strategies, and questioning your long-held beliefs. You’ll never grow and learn as a team if you stick your head in the sand. Radical Candor ensures your eyes and ears are open to the critical feedback and guidance your team can offer.

Now, what about sales reps?

The same authentic relationships that supercharge your sales team can also help you better qualify, communicate with, and close prospects.

We’re all constantly being sold to. And it’s probably safe to say that your prospect’s BS meters are fine-tuned to sniff out inauthentic sales pitches and persuasion techniques. Instead, you must create a safe space to turn a prospect into a customer where they feel trusted and heard.

This is where the elements of Radical Candor can be applied. Once you show a prospect that you care personally and understand their situation, it’s much easier to challenge them directly with your solution or product.

Instead of tricking or persuading them into saying yes, you’re building a relationship founded on trust and honesty.

The Simple Mistakes That Turn Radical Candor into Aggression, Manipulation, and Apathy

When you talk about it in high-level terms, Radical Candor sounds simple. Just be honest with your team or a prospect and challenge them head-on.

Unfortunately, this over-simplification can seriously backfire if you’re not careful.

Too many people use the guise of Radical Candor to be jerks, overly aggressive, and manipulative. (If you watch the HBO series Silicon Valley, there’s a whole episode where a character says he’s practicing Radical Candor to “tell inconvenient truths” when he’s just being an asshole).

Radical Candor exists at the perfect intersection of caring personally and challenging directly. However, even being slightly off can turn what was meant as positive and authentic feedback into something harmful.

According to Scott, a small shift in your approach can lead to several undesirable consequences:

• Manipulative insincerity: Challenging someone without caring about them personally is just manipulation. This is where those Houdini-like “persuasion hacks” come into play. Ultimately, it might help you close a sale or force your teammate to do what you want, but the relationship will inevitably sour. Who feels good when they’ve been lied to?
• Obnoxious aggression: When you push manipulation even further, you become the overbearing jerk who doesn’t care about anything but their own needs. Think of the salesperson who lashes out at objections or pushes hard for a sale even when it’s a bad fit. Or the manager who yells at their team for any minor problem in the name of “being honest.”
• Ruinous empathy: Finally, you can also fall too far in the other direction. It’s just as bad always to try to be “the nice guy.” You're letting everyone down when you only care about keeping people happy and not challenging them to be their best. For sales leaders, this means allowing a teammate fail on purpose. While for reps, it leads to fear of asking for the sale or pushing past objections. Instead, I always advocate for friendly strength.

It comes down to the fact that Radical Candor isn’t about sugar-coating criticism but rather about creating a relationship with your prospects and peers where honesty and authenticity are expected. Criticism is always taken in good faith.

If you want to reap the benefits of being radically candid, you must balance caring personally and challenging directly. So, let’s move away from the high-level theory and look at some practical ways sales managers and reps can build a culture of Radical Candor.

Sales Managers: How to Use Radical Candor to Empower Your Team and Build a Better Culture

As a sales leader, Radical Candor can help you manage and empower your team, build the right culture, and teach your reps to better communicate with prospects. So how can you create a sales culture based on Radical Candor?

According to Scott, a radically candid culture comes down to three factors:

1. Guidance: Creating a culture of open and honest two-way guidance.
2. Team-building: Understanding what motivates each individual on your team to do their best work and creating psychological safety.
3. Results: Driving collaborative results by teaching your team the elements of Radical Candor.

Let’s look at practical ways to apply each of these to your sales team.

Guidance: Better Manage Your Sales Team with Two-Way Guidance

Guidance is at the core of Radical Candor. But anyone who’s led a team knows it’s not always easy to give guidance to people who want to listen. As Scott writes:

It’s brutally hard to tell people when they are screwing up.

But guidance isn’t just about criticizing your team when they’ve missed a target. As NBA All-Star Andre Iguodala explains:

The secret to winning is to point out to great players what they could have done better, even when they have just won a game.

A culture of Radical Candor means always asking for guidance, giving it freely, and accepting it from everyone on your team. There’s no hierarchy. Instead, creating a two-way street of caring personally and challenging directly would be best.

Here’s how that looks in practice:

• Ask for feedback first: Once you’ve explained the process of Radical Candor, ask to get it before you dish it out. Guide your team on how they can give you guidance and feedback. Remember that culture starts at the top.
• Ensure praise has context and specificity: Everyone can smell fake praise. To build Radical Candor, you need to care about your team. Learn what motivates them, where they’re putting their efforts and their unique skills, and then focus your praise around those factors. Whenever you praise a teammate, ensure that you’re being specific and providing context to show that this is more than just a passing comment.
• Follow the HHIPP model when criticizing: Radical Candor isn’t just about being blunt. It’s about inspiring change. When you challenge someone on your team, you must ensure your feedback is HHIPP: Humble, helpful, immediate, in-person, and doesn’t personalize… In Scott’s words: “It’s not mean, it’s clear.”

Do: “Put your own oxygen mask on first.” To care personally about your team, you must be in the right mind. We’re all sick of hearing self-care advice, so do what works for you. If that means getting more sleep, hitting the gym before work, or binging on Netflix for a weekend, go for it.

Don’t: Treat errors as personality traits (instead of behaviors). Radical Candor is all about facilitating change. But that also means you must see that your team can change. When someone screws up, you’re not criticizing them personally but giving them guidance to get back on track.

Here's what our Director of Sales, Nick Persico, had to say on the subject:

Constant feedback is critical for helping good salespeople become great. You have to provide feedback on just as many BAD calls as GOOD calls.

Like most things in life, it’s about balance. Some calls will be brutal, and it’s important to go back and listen to those calls, but you should also listen to the good ones and share them with others.

Team-Building: Build a Better Team Culture by Creating Psychological Safety

Picture the last time you had a tense argument with your boss. Now, imagine telling them, “No, you’re wrong!”

Radical Candor means overcoming one's fear of speaking up in one's workplace and understanding that authentic relationships, not power, drive one's team forward.

Unfortunately, too many people were taught to kiss up to their superiors. To be radically candid, you need to help your team unlearn the idea that they need to sugarcoat what they’re saying or that being honest isn’t polite.

Psychologists call this “psychological safety”—the belief that you won’t be punished for making mistakes or criticizing people in power. As a sales leader, you can create a culture of psychological safety that spreads through your team by following a few steps:

• Bring your whole self to work: Your team needs to trust you to feel safe, and trust comes from opening up. Share your values with your team, and don’t just try to “keep it professional.”
• Adopt a learning mindset: The fastest way to kill the trust you’ve built is to threaten someone when they’ve screwed up. Remember that you don’t always have all the facts when you challenge directly. Instead of telling them what to do, try to learn why your teammates acted the way they did. Ask them for solutions and dig into their process.
• Ask for feedback on your own delivery: Encourage your team to criticize you and ask them directly how your guidance impacted them. The more open the lines of communication, the more vulnerable you allow yourself to be, and the more radically candid they’ll be.

Do: Make it more accessible to “speak truth to power.” You can’t say you’re practicing Radical Candor and cannot take it yourself. Give your sales team opportunities to criticize (or praise) you without fear of retribution.

Don’t: Let teammates backstab each other. Psychological safety isn’t just between managers and employees. If someone comes to you with an issue with another team member, don’t indulge in their venting. Instead, get them to try to hash it out themselves (radically candidly, of course). If they can’t find a solution, you’re there for support.

Results: Empower Your Sales Reps to Use Radical Candor to Communicate with Prospects

Once you start practicing Radical Candor as a team, the next logical step is to bring it into your sales process.

The honesty and openness that Radical Candor creates within your team can help your reps close more deals, overcome objections, and ensure they’re not wasting time on the wrong prospects.

While we’ll discuss each of these elements in the next section, it’s your responsibility to ensure that they don’t slip into obnoxious aggression or manipulative insincerity.

Here’s how you can do that:

• Start by explaining the basics of Radical Candor. If you haven’t already, dig deep into what it means to care personally and challenge directly. Show examples of how you’ve tried to bring these elements into the company culture and also explain the dangers of getting it wrong.
• Ask people to be radically candid with you. Think of this as “dogfooding” (when you use your product to test its benefits). Not only will this help develop your own radically candid culture, but you’ll also be able to guide your team on their approach.
• Stress the importance of authentic praise. The goal of Radical Candor is to create genuine relationships. Not surface-level ones built on superficial gestures. Use your CRM to keep detailed notes on prospects and customers, so your team can show they care personally about them and their business.
• Give them guidance on how to challenge prospects directly without pushing them away. Not every prospect will respond to being directly challenged, but if your team has done its job showing they care personally, it shouldn’t run away. Coach them on using the HHIPP model to keep criticism positive (without sugarcoating it).

Do: Walk the walk. A culture of Radical Candor should naturally move from the workplace into your team’s sales process. But that doesn’t mean this is a set-it-and-forget-it system. You must constantly give and ask for guidance and practice Radical Candor internally to make it an ingrained part of your culture.

Don’t: Ignore workplace biases or cultural influences. Radical Candor is for everyone. However, you need to be keenly aware of some factors when applying it. Gender biases, diversity issues, and cultural differences can make how you show you care personally and challenge directly more difficult. Address these issues head-on and let your team know they can come to you if they need help.

Sales Reps: How to Build Better Relationships and Close Customers for Life

Alright, let’s get into the fun stuff.

It’s hopefully clear by now just how powerful Radical Candor is for creating better workplace relationships. But how can you use it to sell more?

The best sales reps find a balance between being pushy and being a total pushover. They care about their prospects and clients as well as the bottom line. And they understand that the best deals are the ones where everyone comes out feeling like they’ve won.

This is Radical Candor in a nutshell.

As a sales rep, with a few tweaks, you can use Radical Candor to ensure you’re going after the right deals, get other common objections, and even close more deals by building authentic relationships with your prospects. (Not to mention, it’s a powerful way to become a better teammate and employee!)

So many of the core issues we deal with on the Close blog can be made easier by using Radical Candor, from better qualifying and communicating with prospects to overcoming common objections and asking for the close.

Tell Your Prospects NO

Yes is every salesperson's favorite word. There's no sweeter sound than a prospect telling you:

• Yes, that sounds interesting.
• Yes, I want to buy that.
• Yes, let's sign that contract now.

And we, as sales professionals, also like to tell our prospects yes:

• Yes, our solution can do that.
• Yes, we have that feature.
• Yes, this is a great fit.

Saying yes is easy and feels good, but the best sales reps say no to their prospects when it's the right thing to do.

When a prospect is not a good fit for what you're buying, tell them. We do it all the time. People try our sales CRM, talk with us, and then want to become customers. However, during the qualification stage, we sometimes find that our software is not the best choice for them.

People often want to buy our software, and we tell them: "No, you shouldn't buy Close. We're not a good fit for you because you need a solution that [accomplishes one thing specific to their sales process that Close doesn't do well]. I suggest you look at [competing vendor] instead."

This takes people aback. How many times have you spoken with a sales rep, told them you want to buy, and the sales rep then told you, "You shouldn't. Check out this other vendor instead."

Not often, probably.

Here's why we're doing it:

• It's the right thing to do.
• Selling to prospects just because you can, even though they shouldn't, will ultimately hurt your business.
• It makes a lasting impression and often marks the beginning of a long-term professional relationship.
• These prospects often recommend you to others who might be a good fit. So, by saying no to that one customer, you often get a lot more (and better) business in the future.
• These prospects might one day work in a company where Close would be a perfect fit, and they'll remember the integrity we treated them with and become customers. It has happened so many times!
• And yeah, again, it's the right thing to do.

Surface Issues Upfront

Sometimes, as a sales rep, you get a sense that there's potentially an issue this prospect wouldn't be happy about. But since they don't bring it up explicitly, you kind of skip over it as well and hope it's not a big deal.

I get it. It's the easy thing to do.

But don't give in to that temptation. As so often in life, doing the opposite of what's easy is exactly what you should be doing.

Here's an example:

Prospect: "I need a CRM that a) helps my sales reps be product and make more calls. b) I also want easy reporting to know how the overall team is performing, how individual team members are performing, and which area I should focus on when coaching them. And I want c) a full-featured mobile app."

Close sales rep: "We can do A and B. These are some of the features our customers love about us, and I'm happy to demonstrate them to you. But we do not have a full-featured mobile app. What do you think? Which of these three things you mentioned matters the most to you?"

When you bring it up on your own, instead of trying to downplay the issue, you earn a prospect's trust. They recognize that you're the kind of sales rep who really has their best interest at heart, not just their commission.

What do most sales reps do?

They try to glance over the issue. But then, when the prospect later discovers it on their own, do you know what happens?

It often collapses the deal the sales rep has spent much time working towards. Trust is lost. Time is wasted on both sides, and your reputation takes a hit.

If, on the other hand, you point out issues proactively and work with them to resolve them, it happens so often that the prospect says: "You know what? I think we can live with that. There's no perfect solution, and I can see that your CRM will help our reps close more deals. A mobile app would be great, but it's not a dealbreaker."

Ask for Help

Sometimes, you reach a difficult point in a sales conversation. Do you know what I do? I ask the prospect for help.

Here's an example:

Prospect: "The most important thing for us is speed. We need this implemented real fast, basically it should have been done yesterday. And what matters to us is quality, security, and safety. We can't tolerate any errors or mistakes with this."

If you've been selling SaaS for any time, you've probably heard prospects say something along these lines. But you also know that this doesn't work. If speed is your religion, quality can't be. If speed is your north star, you have to be ok with breaking things.

Whenever there’s an example of conflicting or puzzling information from the prospect, don’t just rush by that.

Often, the prospect can help you sell to them if you just ask for it.

"Help me out here" also works when:

• A prospect keeps bringing up new objections
• They go quite
• When you're ready to close the deal, they suddenly bring up a budget as a dealbreaker
• Most scenarios where a sales conversation reached an impasse

Curious to learn more? Check out 4 simple words that unlock difficult sales conversations.

Cancel Proof Your Prospects

This is a very old sales tactic, but if you apply it with the right intent and have your prospect's best interest at heart, it can be highly effective.

Once the prospect seems ready to buy, you ask them: "It seems like this would be a perfect fit—but what could prevent you from signing the contract? What could be potential dealbreakers?"

Surface these things and discuss them (rather than hoping they don’t come up).

In the early days of my sales career, I told clients who wanted to buy from me, "I can't let you buy from me just yet." I'd then proceed to essentially give them homework and prepare for an "exam" they'd have to pass to qualify. You can read more about this here.

It's a powerful way to ensure that prospects only buy if they're really sure your solution is the right fit, to pre-empt buyers' remorse, and to ensure that they'll actually implement and benefit from your solution.

Challenge the Prospect

Some of the best salespeople I know love opportunities to challenge a prospect candidly. There's something immensely satisfying when you see a prospect you care for act incongruously and can help them arrive at a more coherent course of action.

One of the members of our sales team once challenged a prospect to import their leads into Close on the same day and helped them set up a sales workflow that allowed them to work their sales pipeline more productively and faster than ever before. You can read the full story here, but be warned, there was some explicit language in that challenge.

Let’s now examine some of the other areas where sales reps can use Radical Candor to their advantage.

Qualifying the Right Prospects

How often have you spent hours chasing a prospect only to realize you were in the wrong race from the start?

Without qualifying your leads, you’re wasting everyone’s time and missing out on potentially better opportunities. Remember, selling to the wrong customer is often worse than losing a sale.

The key to qualifying your leads is to listen to them. You need to understand their wants, needs, and fears deeply. In other words, you need them to open up and be vulnerable with you. With Radical Candor, you get a mental toolkit for quickly building relationships with new prospects and understanding if they fit your offer well.

Take the time to show you care personally by asking meaningful questions and using active listening techniques. For example, don’t just jump into your pitch. Instead, a radically candid conversation follows a specific path that you can modify for sales calls and emails:

• Listen to what they say about their current situation, needs, wants, and dreams.
• Clarify that you understand by asking follow-up questions and repeating what they’ve said to them (this is called active listening).
• Decide your best approach to challenge them directly based on what you’ve learned.
• Continue to challenge them directly and listen to their responses to persuade them that your offer is the best option for them.
• Learn from the results and work them into your next pitch.

This cycle of radically candid conversations is a rapid-fire approach to building relationships with prospects that are authentic, built on listening, and more likely to end up with you targeting the right people.

Getting over Objections

Sales are all about change. And it’s inevitable that when you ask someone to change, they will come back with objections. They don’t want to change. But it’s your job to show them why they need to.

When you practice Radical Candor, you’re already set up to predict and pre-empt any objections your prospects might have. Here’s how:

• Caring personally means you already know what objections your prospect might bring up. One of the Seven Deadly Closing Sins is asking for the close selfishly. This is when you try to close a sale before knowing why they will benefit from your product or solution. Caring personally and building an authentic relationship means you listen to their feedback and understand your prospect’s fears and current situation to the point where you can predict where they might have objections or concerns.
• Challenging directly creates a safe space to break down objections. Instead of waffling around an answer, challenge the objection directly in real time and be clear and to the point. You already know what they’re concerned about, and you’ve shown that you care enough to speak the truth to them. You’re not being mean. You’re being clear.

Many of the most common sales objections fall into the same buckets: price, fit, too busy, competitors, etc.… With Radical Candor, however, you build an authentic relationship that squashes many of these potential objections before they arise and gives you the power to speak freely and openly about the rest.

How a Close Sales Rep Used Radical Candor to Handle an Objection

James Urie, Senior Account Manager at Close, shared this story with us:

This story illustrates that practicing radical candor is not easy. But, as often happens, doing the hard thing is ultimately what will deliver sustainable success.

Dealing with Rejection

Like objections, rejection is just a part of sales. But you can’t go into a sale afraid of hearing no.

Here’s some hard truth: 92 percent of salespeople report giving up on a prospect after hearing "no” four times. Meanwhile, 80 percent of prospects report saying “no” four times before finally saying “yes.” In other words, most salespeople give up before a prospect can say yes!

Radical Candor is about embracing conflict and change and not fearing them. Instead of avoiding hard conversations, you build authentic relationships where they thrive and everyone feels they can speak honestly. This might result in rejection during your sale process, but it also means you’re set up to deal with and counter their rejection emotionally.

When you hear a rejection, think of it as your prospect guiding you. Rather than a “no,” this is just another place for you to work on your relationship with them. It’s a slight shift in thinking, but it stops you from giving up prematurely.

Besides, according to Shark Tank investor Barbara Corcoran, dealing with rejection emotionally can be the difference between salespeople making $40,000 and $8 million per year.

Getting Over Your “Failure to Close”

Radical Candor turns asking for the close into a non-event if done right.

The best salespeople guide their prospects through the sale. They create a sense of psychological safety. They build personal connections. And they address issues directly. But most of all, they’re not afraid of asking for the close.

Rather than stressing over what your prospect will say, practicing Radical Candor means you’ve built a personal connection where you can push back against objections, emotionally handle rejection, and challenge them directly to say yes to the offer.

You’ve put in the work, so why wouldn’t they trust you enough to buy from you?

Turning One-Time Sales into Customers for Life

Lastly, all this relationship-building isn’t just to get you close a deal. As a sales rep, Radical Candor builds connections beyond sales cycles or companies. You feel comfortable following up with these people when you have a new offer or reach out to them when you switch roles or companies.

Radical Candor creates recurring income and job security by turning one-time sales into lifelong customers.

Swap the Sales Stereotypes for Something More Positive by Practicing Radical Candor

One of the pieces of advice that Scott repeats throughout her book is that relationships don’t scale, but culture does. The more you practice Radical Candor as a sales manager or sales rep, the more it will become a part of your personal and company’s ethos.

By caring personally and challenging directly, you’ll become a better teammate, a more influential communicator, and a more robust sales professional. But all those benefits don’t come without hard work.

There’s no shortcut to building an authentic relationship. But with Radical Candor, you know you’re always on the right path.

Get more tips and strategies for developing a strong relationship with your buyers, turning them into life-long customers. Download my book Talk to Your Customers free!