Be more assertive with customers

Your customers called—they want you to take the reins and drive.

Jan 17, 2024

👋 Hey, it’s Wes. Welcome to my weekly newsletter where I share frameworks for becoming a sharper marketer, operator, and founder. If you’re not a subscriber yet, here’s what you missed:

Subscribe to get access to these posts, and all future posts.

In this week’s newsletter, we’ll dissect what it means to be assertive, the mental models holding you back, and how collaborative personality types can take control while respecting customers.

If you find this helpful, please share it to help others. Enjoy.

Read time: 10 minutes

I like working with self-aware people who aren’t overbearing or pushy. This is usually good. But there’s one downside. This kind of collaborative personality (a bucket I’d put myself in) can have one issue: we can feel sheepish, and therefore be too conservative when working with customers.

In an effort to avoid being perceived as pushy or salesy, we end up overcompensating. There is such a thing as respecting the customer’s agency too much.

Team members who are afraid to speak up with customers can cost companies millions in revenue from lost opportunities, lost upsells, lost partnerships, and lost contracts. Plus, it diminishes your hard work and morale if you’re constantly worried that you might upset your customer. This is why it’s important to feel empowered to push back with customers and learn the skills to do so effectively.

There are dozens of moments when you’re talking to prospects, customers, or partners, where you can choose to (a) be more assertive or (b) take a step back. In those moments, I hope you’ll decide to speak up, knowing this proactive posture will serve the customer and you.

When and where could you be more assertive? You might recognize these scenarios:

Customer questions: A customer asks a question. You answer it at face value without adding context or explaining why your suggestion benefits them. Your interests are aligned (you only win if they win), but they think they’re doing you a favor by continuing to buy from you.
Feature requests: A customer asks “Can your product do x?” You don’t have that feature, so you apologize and let them know it’s on the roadmap. You know the feature isn’t as critical as they think it is, but you say nothing.
Product/business context: You have a rare bird’s eye view from working with dozens of customers. But you don’t share your insights because you’re afraid of accidentally insinuating that your customer doesn’t know everything.
Unwarranted complaints: Your customer complains about an issue that wasn’t your team’s fault. Instead of helping them understand the situation, you accidentally admit fault. You didn’t realize the cost of this: Now, they are even more emboldened and demand that you correct the transgression.
Account management: Your important client doesn’t reply to email. If you had their cell phone number, you could text them and offer support in a way that might be easier for them. You have a good relationship, but you’re afraid to ask—they might see it as overreaching.

Moments like this happen every week, and they are all opportunities to add value by guiding your customer.

It’s your responsibility to drive the conversation

One of my biggest pet peeves is when you walk up to a sales associate in a store, and they wait for you to drive the conversation.

A few years ago, my husband and I went to the Bonobos store in Soho to get him some pants. We had looked at their clothes online and knew the store was a showroom, but we weren’t sure how it worked. We walked up to a salesperson.

“Hi,” he says. Then silence.

We wait, thinking he’s going to ask what we need. Nope. He stares at us, blinking.

This is annoying. If a customer walks up to you, they need something. You should ask, “Hi, what can I do for you?” or “Hi, welcome to Bonobos. Can I help you find anything?”

Customers are used to salespeople driving and at least asking what they need. So when you don’t ask, it creates a moment of confusion.

More importantly, it’s your job to help customers. When you just say “hi” then go silent, you’re acting like I walked up to you in a bar and you’re not pleased about it. No dude. Given the situation, there are dynamics and roles at play: You are not simply John. You are John, a representative of Bonobos. I am not simply Wes. I am Wes, a customer shopping at your store. You work here. It’s your job to lead.

By the way, I say all this as someone who has worked in multiple retail stores. When I worked at Sephora at the mall near my hometown, I wasn’t simply Wes. I was a representative of the company. That was my role, and that’s your role when you’re at work.

This seems like common sense, but it happens surprisingly often. And while it might seem like a minor example, it’s simply one example of how passivity expresses itself. Being passive expresses itself in other ways, and it reflects the underlying posture of how you see yourself and your role with customers.

Another example: Last week, I had a call with a vendor. I called her and said, “Hi Jane, this is Wes Kao.” She says, “Hi!” Then silence. More silence. I thought, “Is she going to say anything?” Nope. She put the burden on me to drive this call forward. She was the founder, so for what it’s worth, this is a problem that can happen at all levels.

Before: Hi! [Silence. Waiting for the customer to drive the call.]
After: “Hi, how are you? I’ve been looking forward to our call. [Insert small talk, like asking where the person is based.] If it’s alright with you, I’m thinking today we can start by hearing a bit more about what you’re looking for, then I can share a bit about our company, how we’ve helped folks like you, answer any questions, and go from there. How does that sound?”

As the company representative, you have talked to way more customers than I have to vendors. You are trying to sell me. Don’t make me do the work of thinking of how to run this call. It is YOUR responsibility to run this call.

Running a call doesn’t mean monopolizing the conversation. It means setting the agenda and the scaffolding, including making sure the other party has room to share.

If you take your hands completely off the wheel, it’s shirking your responsibility. Never put the burden on your customer to drive the conversation. Run the call.

You’re not “bothering the customer”

If you are a founder/account manager/salesperson/marketer, you may often feel like you’re pestering your customers, especially in dynamics where you’re constantly following up. It’s important to remind yourself that you are serving your customers, not bothering them. You are not asking them for a personal favor. And they are not doing you a personal favor when they comply with your requests.

Ask yourself:

How does my suggestion benefit the customer?
How does this help me help them?
How is what I’m doing in service of them?

When you hold back, you’re harming your customer

Where does this self-consciousness about being too salesy come from? This is worth unpacking because there are lots of tactics on how to be assertive, but I believe we need to acknowledge the root cause:

You’ve probably dealt with salespeople who were overbearing, and said to yourself, “I never want to be like this.”
You’ve probably been blamed in the past when things went wrong with a customer. You learned that it’s safer to be more conservative than to lose a customer because you were too aggressive. You don’t want a customer to call your manager and complain that you were out of line.
Conflict feels scary and risky, even if it’s productive conflict you know you should embrace. Many of us were raised in environments that prioritized cooperation.

I check off all three boxes above, so if you do too, I know how you feel. Here’s the thing: if you’re the kind of person who worries about any of this, you are probably not going to be too aggressive, even if you tried.

The kind of people who should be more self-aware are too busy being domineering. You, on the other hand, are likely the kind of person who has room to dial it up a notch. It will feel uncomfortable at first, and you’ll need to figure out where your edges are. The upside is worth it: You will feel more empowered, you will be better at influencing others, and you will improve your ability to get things done.

It takes courage to engage in productive conflict

Being collaborative is a strength—it’s gotten you to where you are and is a reason people enjoy working with you. But when strengths are applied in the wrong way or in the wrong situations, they become a liability.

It’s possible that a part of what you call “being collaborative” is actually a fear of conflict:

Avoiding conflict isn’t collaborative if it’s doing your customers a disservice.
Staying silent isn’t collaborative if you withhold information your customer would find relevant and valuable.
A reactive posture isn’t collaborative if your customer is waiting for you to lead.

It takes courage to engage in productive conflict. Your customer benefits when you are brave enough to speak up, respectfully disagree, and share information that may be at odds with their current knowledge. It’s uncomfortable for you in the short run, but when you do this emotional labor, it benefits your professional growth, your company’s revenue, and your customer’s business in the long run.

Here’s a story of how pushing back respectfully led to increasing profitability, from Bruce Clark, Associate Professor of Marketing at Northeastern University:

…An industrial products manufacturer did a thorough customer profitability analysis for the first time in a long time. They found that some of their very high volume accounts—and ones on which the sales force made a lot of money—were deeply unprofitable for the firm. The first instinct was to start weaning off the unprofitable customers, easing them towards the exit.
But instead, the finding provoked conversations with these accounts, many of whom had assumed (as the salespeople had) that they were a great account!
Could they identify the behaviors that were leading these accounts to cost the firm so much money? In many cases they could. Some accounts were indeed let go, but others changed, and the conversation ended up deepening the understanding of each others’ businesses.

To be clear, being assertive does not mean saying what you usually say, but more forcefully. It’s not about your tone. It’s about leading your customer to where they want to go.

In order to take the reins, you need both strategy and confidence: You need to know where you want to take them (strategy) and realize you’re the best person to take them (confidence). If you only have the strategy of where to take them, but no confidence, you won’t speak up. If you only have confidence but no place to take them, you have nothing to speak up about.

The customer doesn’t know what’s best. You might.

Does reading that sentence make you uncomfortable? Sure, the customer knows themselves. Fine. But reread that header sentence and consider how it might be true. When might the customer think they know best, but actually, you know best?

Customers don’t always know what others in their category are doing. They don’t always know what’s working for other teams. They don’t always know what they need. They don’t always have context about whether a data point is “good” or “bad” relative to the market.

For example, at my company Maven, my team and I have spoken with hundreds of instructors 1:1 and have more knowledge on how to grow a successful live course than most individual instructors do. Each instructor only sees their own course—their context is super limited. But Maven employees see 100x more cohorts, over time, in varying stages, from all types of instructors, etc. We have thousands of data points on both instructor and student behavior, and we have seen the inner workings of courses of all sizes from $10k/year to $3M run rate. This is where our expertise stems from. It would be irresponsible of my team—and more importantly, it lets the instructor down long-term—if we simply let them do what they think is best.

Educate your customer: If they knew what you knew, would they come to this conclusion too? You might have information, data points, and insights your customers don’t have. If you have a hunch that something is better for them, but you’re not sure how to say it, don’t stifle that hunch.
Sell why your ideas benefit them: Have you given them reasons to say yes? Many times, we accidentally focus on why an idea benefits us and our goals, but forget to appeal to the customer. Yes, it benefits you, but you don’t need to say those reasons because subconsciously the person knows you’d only bring this up if it benefits you. Focus 90% on why the idea benefits them.
Address the question behind the question: Customers might believe they need help with a specific solution instead of articulating their problem. And even when they articulate their problem, they might not be able to explain it well for a variety of reasons. As the product builder, it’s your job to dig deeper and tease out the QBQ. More on the question behind the question.
Help them interpret the information you’re sharing: Don’t just drop a fact or piece of news. It’s shocking how often I’ve shared a data point where I thought the implication was obvious, and the person’s reaction is “Wait, is this good or bad news?” It’s not as obvious as you think.
Maximize every customer interaction. You don’t have that many interactions with customers/partners for you to treat interactions as throwaway. Every touchpoint is an opportunity to reinforce the value you bring, teach them something they don’t already know, and make them think it was a good decision to work with you. This requires a default active posture.

For this to work, psychological safety is paramount. If you’re in a position of leadership, reward your team for pushing and occasionally missing the mark, vs being too conservative as their default. It doesn’t take many wrist slaps for a high performer to think, “Yeah this isn’t worth it. I had good intentions trying to convince the customer, and it was 50/50 on whether it could have worked. I’m just going to err on the side of being safe from now on.”

This is a failure state if your people think this. When team members learn a new skill, they’re like a baby giraffe learning what legs are. It’s going to be wobbly at first. If you want to see more boldness, you need to reward attempts to be assertive, not only the outcomes of being assertive.

To recap: Being collaborative and being assertive aren’t at odds—they work in tandem to allow you to better serve your customers. The next time you have a chance to be more assertive with a customer, in that split second, I hope you’ll choose to be generous by sharing what you know and taking the lead. Try it, and I’d love to hear how it goes.

I’d love to get your help growing our community of thoughtful, rigorous operators. If you found this valuable, consider subscribing or taking a moment to refer a friend.

Thanks for being here,

Wes Kao

PS See you next Wednesday at 8am ET.

PPS If you’re loving this and want to binge-read, check out these other essays on ways to be assertive with finesse.