Episode 487: Virtual Selling and Discovery Excellence: Humanizing the Hybrid Sales Experience with Karen Kelly

Karen Kelly 00:00
For me, it’s moving away from the traditional way we sold. When you think back to when I started, and maybe when you started, you had to be in front of a person in an office, in a boardroom.

Bob Woods 00:10
Welcome to the Making Sales Social podcast, featuring the top voices in sales, marketing, and business. Join Brynne Tillman, Stan Robinson Jr., and me, Bob Woods, as we each bring you the best tips and strategies our guests are teaching and using so you can leverage them for your own virtual and social selling. Welcome to the show.

Brynne Tillman 00:33
Welcome back to Making Sales Social. I’m Brynne Tillman, and I am super excited about my guest today, someone I know in real life, not just through Zoom. Karen Kelly is a keynote speaker, sales trainer, and fractional sales leader recognized as one of the 100 most powerful women in sales. She is the CEO and founder of K2 Performance Consulting and the creator of K2 Sales Academy, where she helps sales leaders transform their teams through proven, engaging training. Karen specializes in virtual selling, discovery excellence, and equipping core performers with the confidence and skill set to become top performers.

Karen, welcome to the show, my friend.

Karen Kelly
Thank you so much, Brynne. Delighted to be here.

Brynne Tillman
I am so excited to jump into your genius. But before we get started, we ask all of our guests the same first question, which is: What does making sales social mean to you?

Karen Kelly 01:31
When you think of the word social, for me, I think of a coffee shop. That means conversation, getting to know someone, building relationships. For me, it’s moving away from the traditional way we sold. When you think back to when I started, and maybe when you started, you had to be in front of a person in an office, in a boardroom. Then it moved to virtual selling. Now we know 73% of buyers would prefer a rep-free experience.

So how can we engage with people in a non-threatening way on a platform of their choice? For B2B, for me, that’s LinkedIn. It really is about getting to know the person, showing up as your true self so that as people are wondering, “Can this person help me? Should I connect with them?” what you’re putting out there is helpful. You’re delivering value. When they meet you, there’s alignment, a congruence between what you’re saying and your virtual presence.

I think it’s about building relationships, leading with curiosity, and trying to build a relationship where either you can help them, they can help you, or at the very least, you leave someone better off than when you first met them.

Brynne Tillman 02:44
I completely love that. I love the line, “You leave them better off than when you met them.” Just a little enhancement in their world is enough. You brought value. I really love that.

When I was doing some digging, I noticed that you work closely with teams selling in a hybrid environment. What shifts are you seeing happening? I know I say “shifts”—it’s been like five years already—but what are you seeing, and what shifts do leaders need to make in order to get the most out of teams when they don’t have the same control they had years ago?

Karen Kelly 03:32
When you think of hybrid, you’re referring to in-person and virtual. Is that correct?

Brynne Tillman
Yeah.

Karen Kelly
I feel like people are definitely Zoomed or “Teamed” out. To get the most out of them, this is what I do with my customers: If I have a meeting with them, I’ll send a quick video beforehand saying, “These are the expectations. This is what we’re going to discuss. Maybe read this—this third paragraph really talks about your team dynamics.”

Maybe you get that call down to 15 minutes and give people back time. A lot of meetings go on too long, and there’s a lack of engagement. Some people are dealing with a virtual environment the way they would in person, but there are different dynamics. People need to understand how they respond. Should they respond? Are we going into breakout rooms?

A lot of it is ensuring they’re applying best practices, even though we’ve been doing this for a while. Also, if you don’t need to do a Zoom call, don’t do one. Is it a phone call? An email? A text?

Even for me, if it is a Zoom call, can you get it down to 15 or 20 minutes and give someone content and context in advance so that when everyone joins, you’re ready to hit the ground running? Everyone knows the roles. They’re primed with the questions because you’ve set clear expectations about why you’re meeting and what results you should achieve by the end.

Brynne Tillman 05:00
I love that. We do that with clients, but we rarely do that internally, and I think that’s really powerful.

There are challenges with hybrid or remote teams—signs of disconnect and even performance decline. What do you recommend to get them more motivated and excited again? When a sales leader comes to you and says, “Karen, my team just isn’t into it,” what do you advise?

Karen Kelly 05:36
It’s funny—my newsletter going out tomorrow talks about this. Before the pipeline review and before the deal reviews, the first step is connection with the person. Especially at this time of year, people are stressed about year-end numbers. Just connect with them. Check in. Ask, “How are you doing?”

Understand what motivated them before. Is that still motivating them? Is anything going on? When you connect with a person and help them look inward, there’s usually an unmet need or something on an emotional level that’s not being met. They’re not being heard. That contributes to a KPI not being met.

A lot of leaders just slam the “more” button, but there’s a connection piece missing. They need to feel seen and heard, just like our buyers. Your team is no different. If you’re taking a fear-based or dictatorship approach, you’re going to do more damage. That’s the experience you can expect them to provide to your prospects.

You’re driving results through people. People are built on emotions and energy. At different times of the year, we fluctuate. Really connect with them and understand what’s going on. To do that as a leader, you have to know what’s going on with yourself. You have to do your own inner work and understand your bigger purpose so you’re in a position to help others.

Brynne Tillman 07:09
So you practice what you teach.

Karen Kelly 07:13
You have to model the behavior.

Brynne Tillman 07:17
I love that.

Let’s switch from the seller to the buyer. You spend a lot of time creating memorable buyer experiences. What does that look like, and how can sellers make that happen, even in the early stages of the sales process?

Karen Kelly 07:36
With AI, everyone is looking and sounding the same. The ability to break through and show humanity—being real and authentic, detaching from the outcome—is critical.

If you can do something for somebody, whether it’s an introduction, a genuine comment, or engagement on their post for visibility, and just be others-focused, it goes a long way.

When I connect with someone on LinkedIn, I’ll do a short video and reference something in their profile. “Congratulations on 20 years,” or mention a career switch or something unique. The number one response—an 80% response rate—is, “Wow, you took the time to do that for me.”

At the beginning of a relationship, that sets the tone. If she’s already putting this much effort and intention forward, imagine what she’ll be like if and when we work together. It’s small things, but it’s about being others-focused and stopping the constant “What’s in it for me?” and asking, “What’s in it for them?”

Brynne Tillman 08:44
I love that. One of our sayings is: Detach from what the prospect is worth to you and attach to what you are worth to the prospect.

I’m hearing from sales leaders that top of funnel is harder than ever. Cold calling has changed. People are on their cell phones. Calls show up as spam. Email inboxes are flooded. LinkedIn is often “connect and pitch,” which feels spammy.

What do you recommend reps do to start meaningful, value-driven conversations that earn the right to move forward?

Karen Kelly 10:19
I agree—it is more difficult than it’s been in the past. When we speak in absolutes—“This is dead, that is dead”—that’s incorrect. On its own, it might be dead, which is why we need a multichannel approach.

Find out their channel of choice. Also, what’s your point of view? Are you leading with curiosity? When you reach out, do you have a reason? Even if you’re starting with an assumption, is it timely? Is there urgency behind the problem, or are you just filling a quota and checking a box?

Leverage your network. Who do you want to get in front of? Who knows that person? Can they introduce you? I’m doing more warm approaches. If you’re connected to someone I want to meet, I’ll message you and say, “Brynne, this person is in my ICP. I’d love an introduction. I’ll draft a short note—would you be willing to forward it?”

That de-risks it. Definitely leverage your network. Know their channel. Post valuable content. What are your people talking about? What questions are they asking? Be the response to what they’re looking for. Develop a point of view. Slowly, they’ll start coming to you. It becomes more of a pull system than a push system.

Brynne Tillman 12:36
I love that. Don’t connect without context. If their profile came up in a search, that’s context for you, the seller—not for me, the buyer.

Let’s talk about building confidence on first calls. Discovery can feel overwhelming—don’t demo too soon, ask the right questions. When you work with a team, where do you begin in running that first call?

Karen Kelly 13:56
I back it up and start with mindset. Why are we here? What’s your goal? If it’s to be in service and help someone, that comes through in discovery because you’re leading with curiosity versus pitching because you have to close something.

Sometimes it’s the language: “I have to” versus “I get to guide a decision.” That shift impacts how you show up.

From a discovery standpoint, understand the purpose. “I’m here to understand if you’re facing this challenge, if it’s big enough, if it’s a priority, and if you’re looking to solve it. By the end of this 30 minutes, I should have enough information to determine whether we have another call.”

When you know the bookends—the beginning and the end—it removes nervousness. Your questions are pointed toward a true north. At the end, you can say, “At the beginning, we said we were meeting for this reason. Based on our conversation, are we there?”

They expect that question. Maybe you book another meeting. Maybe you bring someone else in. Or maybe you realize it’s not a big enough problem right now.

Discovery is about the person and the challenge—not pitching. You need the structure of the science, but also the art to dance in the moment, go off script, notice pauses or body language, and dig deeper. If there’s an elephant in the room, address it.

Brynne Tillman 16:21
That’s great. I want to emphasize something you said because it’s so important. You set the agenda at the beginning, and at the end, you ask if it’s been achieved. The reason I want to make sure folks hear that is when they say yes, they’re agreeing to move forward. You’re not asking for the sale. You’re not even specifically asking for next steps. By saying, “Here was the agenda. Did we meet it?” and getting a yes, it launches you forward. I didn’t want to glaze over that because it was such a critical piece of advice. Thank you for that.

Karen Kelly 17:09
Yeah. And they know what’s coming because you’re training them to start thinking, “Okay, I have to get authorization from Bob. What questions would Bob ask?” You’re almost bringing two or three meetings into one because you’re showing them where we’re going and what needs to happen to get there. We need to answer these questions and talk about these things so I can bring this forward internally from the prospect’s standpoint.

When you don’t do that and instead say, “Are we ready to move forward?” they’re thinking, “I have so many questions. I didn’t know this was the next step.” As Brené Brown says, “Clear is kind.” We have to be clear about where we are and where we want to go.

Brynne Tillman 17:46
I have that quote! That’s so funny. We need to talk more. It’s amazing.

One thing you do that I don’t talk about at all is the fractional sales leader piece. Talk about going in as a fractional sales leader. Whether it’s five hours a week or more, how are you setting up KPIs and scorecards? How do you manage a team from a fractional perspective?

Karen Kelly 18:27
You’re still doing all the day-to-day activities of a sales leader. Remove the word “fractional.” When I go in, I’m an observer. I look at what’s already in place—what’s working and what’s not. I work with the team to understand their challenges and concerns because often whoever was in the position before, or whoever is bringing me in, is too far removed from the problem. They’re usually describing symptoms.

I talk to the team, look at the data, listen to calls, and establish a strong baseline. Then I start making recommendations, bring them to fruition, and track the metrics and KPIs we’ve created. I monitor them to ensure they’re moving in the right direction.

I also coach the team. From the start, I focus on connection. You don’t want to be seen as a consultant who comes in one day a week and clocks in and out. You have to be part of the culture. They need to see—and more importantly, feel—that you’re genuinely there to support and develop them.

Having worked in corporate for 20 years, I know what it feels like to have someone who has your back, and I know what it feels like to have someone who simply delivers messages from the top down. To drive results—and why I have a great track record—I connect with the individual and make sure the foundation is solid. That gives me the bandwidth to truly connect because all the measurables are in place. Now we move the people.

Brynne Tillman 20:08
That’s great. When you go into a company, I know the LinkedIn KPIs that matter and the ones that don’t. What mistakes do you see sales leaders making around the wrong KPIs? And what are the right ones throughout the sales process?

Karen Kelly 20:32
Most of them aren’t measuring anything. They don’t have KPIs in place, which is even worse. It’s not redefining—it’s defining for the first time.

For those who are measuring, there’s often no strategy behind the metrics. Maybe someone else did it that way, so they’ve always tracked it that way. Then the question becomes: What are you doing with the data?

Take the BDR role. They may be measured on number of activities or meetings booked. But what about the quality of those meetings? Is the company and contact within your ICP? Did they show up? That’s a big one.

Look at behaviors and why you’re tracking what you’re tracking. I bring the group together and say, “These are the KPIs. What would you add?” When you advance a deal, what actually matters? Is it number of calls? Conversions? I know the big levers, but I also engage the team. When they have ownership and accountability, they’re more likely to adopt it.

Sometimes they’ve tracked something forever, but it’s no longer relevant. The business and customers have changed. You have to assess: Do we still need this? What should we be tracking to ensure we’re hitting our monthly and quarterly targets?

Brynne Tillman 22:20
That’s so important. What about scorecards? What are you looking at when you build those?

Karen Kelly 22:29
I create scorecards starting with leadership coaching because those leaders have to hold their teams accountable. The biggest mistake is either not having a scorecard or painting everyone with the same brush.

I identify four pillars to improve and hold them accountable to. When we meet, the conversation centers on those pillars—communication, leadership, confidence, whatever they may be. I ask for examples and scenarios because I want to see application. I measure progress from where they started.

It’s not just an hourly check-in. It’s, “This pillar is still a gap. What’s happening?” If confidence isn’t improving, I need to understand why. Is it with me? With their team? You start seeing patterns.

When the pillars align with the individual, they feel it. They begin unlocking a new version of themselves. There’s no resistance. You’re helping them become who they want to be.

What motivates one person isn’t the same for another. A 15-year veteran and a three-month rep have different needs and motivations. Why treat them the same?

Brynne Tillman 24:34
I love that. Most sales trainers say, “Get out of your comfort zone.” But most salespeople already have a pretty big comfort zone. I think we should fill the box first before going outside it. That builds confidence, and then growth becomes overflow. What I’m hearing is that everyone has different elements inside their box that motivate them and convert. I love that the scorecard aligns with that.

Karen Kelly 25:16
Absolutely. Sometimes they don’t even realize it. I like adding stretch goals, too. When you stack wins in a couple of pillars, it gives you confidence to lean into discomfort elsewhere.

If you pick the wrong metrics or ones that don’t align, they won’t try anything new. You’re not helping them, and it doesn’t represent who they are or where they want to go.

Brynne Tillman 26:11
Exactly. When you fill one area, it spills over into others.

Karen Kelly 26:19
It spills over and helps you. I love that.

Brynne Tillman 26:22
Karen, this has been so fun. Is there a question I didn’t ask that I should have?

Karen Kelly 26:31
One area people don’t talk about enough—especially for leaders—is being comfortable sharing your misses, failures, and mishaps. It normalizes them.

There’s often an illusion of perfectionism. People hesitate to step outside the box because they fear judgment or missing metrics. Let the walls come down. Share your failures—not necessarily in the moment, but after reflection and lessons learned.

It makes you relatable and human. It gives your team permission to try new things. Failure is part of growth. The worst thing isn’t failure—it’s not trying.

Early in my career, I played it safe because I was getting results. I stayed in my sweet spot. As an entrepreneur, there’s no safety net. I’m out there every day. Sales leaders should embrace vulnerability and model the behavior so their teams feel safe trying new things, knowing failure is an option.

Brynne Tillman 28:04
I love that—failure is an option. That’s powerful. Karen, thank you so much. I’m sure there are sales leaders thinking they need to talk to you. How can they reach you?

Karen Kelly 28:23
They can find me on LinkedIn—Karen Kelly. They can visit my website at k2perform.com and sign up for the newsletter, or email me at karen@k2perform.com.

Brynne Tillman 28:35
Thank you so much. You’re awesome.

Karen Kelly
Thank you. Great questions.

Brynne Tillman
And to all our listeners, when you’re out and about, don’t forget to make your sales social.

Bob Woods 28:46
Thanks for watching. Join us again for more special guests sharing marketing, sales training, and social selling strategies that will set you apart. Hit the subscribe button below to get the latest episodes of the Making Sales Social podcast. Give this video a thumbs up and comment below to let us know what you’d like to hear next. You can also listen on Apple Podcasts, Spotify, Amazon Music, and other platforms. Visit our website, socialsaleslink.com, for more information.