Sales Leadership Unscripted Ep 1: Hey Sales Leaders, Show Me You Know Me

This interview has been edited for clarity and length.

Chris Turner:Sam, super excited to have this conversation. We're going to dive right in. We've talked a lot about you setting records throughout your career, and now you've even started your own business, Sam Sales—a rather fitting title, by the way.

So, Show Me You Know Me—talk to me a little bit about what that is, what the framework looks like, and how it came about. How did you develop it?

Samantha McKenna:This is something I've been talking about for over a decade at this point. Show Me You Know Me is really about demonstrating to the people around us that we understand them—whether that’s our leaders, the people who report to us, or our clients. It applies to every stage of leadership and sales, and honestly, it’s a great principle for personal relationships too.

So what does it mean? Especially for our clients, it means we truly understand them—we know what’s going on in their vertical, in their accounts, and the challenges they’re facing. How many times have we gotten on a call where someone asks, "Tell me about what you do there. How long have you been there? How did you get promoted?"—things we should already know.

Now, let’s think about this from a leadership perspective. How do we use this to attract and retain talent? It’s about showing the people who dedicate their time to us that we care about them. As leaders, we’ve been entrusted with something incredibly important: people. It’s our job to develop them and help them succeed.

How do we do that? We have to understand who they are, what motivates them, and what makes them tick. It’s not just about their 9-to-5 but also their 5-to-9. Do they have kids? Are they passionate about something outside of work? Get to know your people. Show them you know them.

Chris Turner:I love it—especially because not everyone is driven purely by financial incentives. Yes, we’re in sales, and money is obviously a factor, but people have families, aspirations, and personal goals. The better you understand those, the more effective and motivating you can be as a leader.

Samantha McKenna:And it seems so obvious, right? Of course we should get to know our people. Of course we should understand what motivates them.

But I’ll never forget working for a manager for 18 months—we closed one of the biggest deals the company had ever seen, in a tough vertical. I got a lovely bottle of champagne as a thank-you, and the note said, "Something for you to drink with your significant other." And I remember thinking, He has a name.

It’s the simple things. Even if you don’t remember something or you never knew it in the first place—ask. Take the time to do your research. Your team members' peers probably know. Just make sure you show up prepared, even if you're missing some details that you should already know.

Chris Turner:Yeah, I love that approach. And I want to take it a step further—something I know you’re passionate about is radical candor. Bringing that level of honesty into every conversation, stripping away corporate formalities, and just being real with each other is incredibly impactful.

You’re talking about soft skills, and it seems like they’re at the heart of Show Me You Know Me. One example: leaders who use humor and are willing to break character are actually 27% more likely to retain their top talent. Talk to me about soft skills—why are they so important?

Samantha McKenna:One big issue is that leaders don’t spend enough time really getting to know the people who report to them.

For example, let’s say you ask, "How was your weekend?" and your team member says, "It was great—really busy. We took the kids to the park." Instead of moving on, dig deeper: "Tell me more about that. Do you go there often? Is it a family tradition?"

As leaders, we should be teaching our reps to be active listeners with their clients. The best way to do that? Lead by example. Listen actively to them. Not everyone wants to engage in small talk, but by showing genuine curiosity, you build stronger relationships.

Now, humor—it’s a bit harder to teach. You’re either funny or you’re not. I think I’m hilarious. But humor is powerful. It builds connection. It shows vulnerability. On my LinkedIn, I call myself an expert in self-deprecating humor because I will make fun of myself to get a laugh.

Here’s a fun example. Our head of marketing, Paige, has a great sense of humor. She accidentally sent out a webinar link with her dog’s name embedded in the URL. So when 400 people joined, they all appeared as Dakota Tills. I had a graphic artist put her dog’s face on all the Zoom windows, framed it, and mailed it to her. It’s little things like that—it keeps things fun, it builds trust.

Chris Turner:One thing I see a lot—managers want their reps to improve, but they’re not actually telling them how to get better. Can you talk about that?

Samantha McKenna:We’re at an inflection point in sales. A lot of people are struggling to succeed in this market. Leaders are telling their teams, "Go prospect. Dig into buyer pain." And reps are responding, "Okay, but... how?"

And too often, the answer is: "I don’t know either—figure it out."

We have to get tactical. We can’t expect reps to follow a 78-step process over 19 weeks. Start small. What’s the first question they ask in a discovery call? Can we tweak that to uncover buyer pain faster? If emails aren’t getting replies, why? Is the formatting off? Is it too long? Give them practical, tangible feedback.

And leaders need to be brave enough to admit when they don’t have the answers. A lot of them feel like they can’t say, "I don’t know," because their culture doesn’t support that kind of vulnerability. But things have changed—technology, sales tactics—everything is different. We need to acknowledge that, bring in outside experts, and learn together.

Chris Turner:I love that. That level of vulnerability builds trust—the foundational element of a high-performing team.

Samantha McKenna:And when you build that trust, it allows you to have hard conversations. It lets you give radical candor, tough feedback—because you’ve already shown your team that you care about their success.

Chris Turner:Sales is so time-driven—quarterly targets, monthly quotas. How do you balance high performance with genuine care for individuals?

Samantha McKenna:We need to change the way we measure success. Too many teams focus on volume because their conversion rates are so low. If we focus more on quality, we’d see better results.

Some leaders panic when I say, "Your reps should send 50 high-quality emails per week." They immediately go, "A 6% open rate and 1% response rate won’t cut it!" But that’s not what happens when you focus on quality.

We also need to rethink outreach. Instead of emailing a director, email their EVP or CRO. Their inboxes are messier, so your message stands out. And even if they forward you down to their team, you’ve now multi-threaded into the account.

We also need to modernize our approach. Cold calling alone isn’t enough anymore. We need a multi-channel strategy—LinkedIn, DMs, social selling. Smart, quality-driven work is the future.