EPISODE 406: Prospecting Strategies During Roller Coaster Times for Women in Sales with Kendra Lee

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[EDITOR’S NOTE: This is a replay of the Women in Sales Webinar sponsored by the Institute for Excellence in Sales on March 1, 2021. It featured sales expert Kendra Lee.]

Register for the IES Women in Sales Leadership Forum here.

Find Kendra Lee on LinkedIn here.

KENDRA LEE’S TIP FOR EMERGING SALES LEADERS: “One tip that I would give you today is it doesn’t matter that we are in these dynamic roller coaster times, there absolutely is business to be had and we’re seeing an uptick in people realizing they need to do things, they need to make changes. My one recommendation is as you are doing new business development, focus on problems that people have right now. Don’t try and get them to think more strategically about what they’ll need a year from now because they’re focused now. Focus on the issues and the problems that you’re seeing people have right now and that’s how you’ll get in the door.”


Gina Stracuzzi: For the few people in the audience who might not know who Kendra Lee is in the world of prospecting, please tell us a little bit about yourself.

Kendra Lee: Gina said I should tell something fun and I wanted to share that I am not a natural prospector, yet everything that we do in our business is related to new business generation. People are always surprised when I say, “I’m not a natural prospector” because they think I am and I’ve written two books about how you get more leads. When I started my career, I was in accounting and I decided based on the nudging of a couple of my coworkers who said, “You’d be really good in sales” I was going to try it. When I got into sales, I discovered I hated cold calling.

Gina Stracuzzi: You and everybody else [laughs].

Kendra Lee: I hated it but I wanted new business development, Gina. My manager offered me an account management position and I thought that sounded boring for me. Others love account management because they love building the relationships but for me, I wanted to talk to all new people, but I didn’t like cold calling. So I had to figure out how I was going to wrestle with this desire to be a new business development person and the fact that cold calling, to me, was just really difficult.

Gina Stracuzzi: Especially when you’re first getting started in sales, there’s nothing more terrifying than cold calling.

Kendra Lee: Exactly, and that’s where our whole business, KLA Group, stemmed from. It was how I figured out for myself, who didn’t like doing all these things but wanted to be in new business development how to do that. We’re going to talk a little bit about why women are successful today and why they aren’t and the whole fact that it’s a tough time to be doing new business development.

Gina Stracuzzi: It is. I just had a conversation like that with a network connection just the other day who said, “I’m struggling to try to do business development in this period.” It’s one thing to keep nurturing relationships you already have, that’s a little bit different in this time but starting new relationships, that’s difficult.

Kendra Lee: Yes, because none of our normal strategies that we’ve had that may be comfortable to us are available to us. We’re not going to conferences, we can’t go to networking events, we’re not meeting up with people in places where we might have referrals, you can’t really invite people out to lunch as easily, depends where you are. We have clients in Arizona and they’re all going out to lunch, but most of our clients don’t.

Gina Stracuzzi: The ones in the north anyway.

Kendra Lee: Exactly, so we can’t rely on what has made us comfortable and we’re all having to figure out, “How do I prospect differently?” What’s fun is we’ve actually had salespeople who love to do drop-by cold calling which, by the way, I’ve got stories about that one that petrified me. I started my sales career in DC and my manager took me into a building in downtown DC and said, “We’re going to do some cold calling.” Didn’t tell me how to do it, didn’t tell me anything, he just took me to the top floor, opened the door, pushed me and said go. That was awful, still all these years later I remember it and I remember him but I froze. We’ve had people who love doing that – I’m not one of them – who’ve come to us and said, “Now we can’t go do the thing we love most” because they can go in and develop relationships, get to know the receptionist and get past them and schmooze their way in. They’ve all come to us for training on, “What do I do if I can’t rely on my old way, my natural way of prospecting?” It’s very different.

Interestingly, it just struck me, all the people who have come to us who use that approach are men, not women. I’m thinking through all the different people we work with, the higher percentage of those who enjoy doing the drop-by cold calling are men.

Gina Stracuzzi: Kendra, tell us a little bit about how you view the differences between men and women and why women succeed in prospecting.

Kendra Lee: There are very distinct differences and one is not better than the other, it’s being aware of what the differences are. Women are very focused on building a relationship, on nurturing, on staying in touch with people until they are ready to engage. Men tend to be more focused on immediately qualifying what the opportunity is and quickly vetting out what that might be so that they can work it, they’re also more aggressive about getting to decision makers. They’re very different, women and men, in how they approach prospecting. For women, they listen as well because they’re focused on building that relationship. They’re also listening so that they can really hear what the person is telling them.

Gina Stracuzzi: I can see how that can be both a benefit and – as the title of this goes – a pitfall.

Kendra Lee: Exactly, because if they’re more focused on developing a relationship and they don’t get that entree, then women are going to hold back unless they’re very aggressive. We can all think of people who are exceptions to what I’m talking about, so I’m talking more generally but if they’re focused on building that relationship and the door to the relationship isn’t open, then they’re more reticent and that can hold them back from being successful. Let me share with you some of the things that really hold women back, unless you had a comment that you wanted to add.

Gina Stracuzzi: I was thinking about when you first make a call and you might get to the gatekeeper. I think women are not as aggressive or assertive when they’re busy or, “I’ll have them call you.” We’re more polite, we don’t want to offend anyone so I can see how that could get in our way.

Kendra Lee: Yes, and that whole stereotype that happens with women where if we’re too aggressive then that signifies something negative, whereas if men are aggressive it’s considered more positive. I think a lot of women do try to be more polite more naturally because they’ve experienced the negativity that comes when they are too aggressive.

Gina Stracuzzi: We have a question from Denise, she says, “My problem isn’t connecting or reaching out, it’s more what to say in the email or LinkedIn request to have a conversation. I don’t want to start with a salesy pitch, but how do you get them to accept a conversation?”

Kendra Lee: I would look differently between the LinkedIn message and the email. In the email it can be more like your voicemail and it can focus on the problem that you suspect they have. We don’t know for sure, we can have analyzed the target market, the microsegment and the issues that are going on in it related to the title, we don’t know for sure that’s what they have but we can be pretty certain. In your email message, focus on that trigger event that would cause them to need to talk to you or that problem that they might be experiencing, and then offer to share some ideas or some observations or some recommendations that you have from working with similar companies. Talk about the problem and unless this is a brand new industry or geography, however you’re defining your target market, you should be able to look at other clients or even prospects that you’ve spoken to where you’ve identified what the issues are that they’re having that are top priorities right now that you can help with.

Your email very succinctly, in one or two sentences, talks about that problem and the fact that you have some ideas or you have some recommendations or you have some observations from speaking with colleagues of theirs or peers or similar companies. Now that they’re more interested in talking to you because you’re going to share relevant information with them, they want to know what their peers are thinking. That works for email, voicemail and video, not many salespeople are using video but it’s a fabulous way to connect with people. You could make an email, put it in your email and send it.

On LinkedIn it’s more personal and we’re all seeing it. I guarantee, every one of you have seen this, you connect with somebody and instantly you get the automated response. Have you seen it, Gina?

Gina Stracuzzi: I hate it.

Kendra Lee: Yes, I do too. I used to accept anybody on LinkedIn, didn’t matter. There were only a few that I wouldn’t accept, but for the most part 98% of people who wanted to connect with me I would connect with. Now I scrutinize before I accept anybody because I’m afraid they’re going to try and do a sales pitch and I don’t have time for that, we’re busy. So I look very carefully now before I accept it. You don’t want to be one of those people who they accept and suddenly you’re sending something that says, “And here’s how we can help you, this is exactly what we do, this is what our service is and if you have this problem, we can help you. Do you want to have coffee?”

Gina Stracuzzi: I’ve started responding to those with, “Is this really working for you?”

Kendra Lee: I love it [laughs].

Gina Stracuzzi: That’s all I say, I don’t ever get anything back. Shocking, I know [laughs].

Kendra Lee: On LinkedIn, my suggestion is something much more personal. Go back to all th things we learned about LinkedIn, there’s all this data about people. I got one yesterday, he went to the same college that I went to and yes, in the end he said something about this is what he’s doing and his business but at least he was relating it to something about me. In LinkedIn, your connection invitation is about something personal, why you want to connect with them. I get people who say, “I heard you on a webinar, this point really resonated with me.” Or it could be, “I’ve looked at the blogs on your company’s website and I really liked this aspect.” Or, “I like how your company stands for…” whatever they stand for in the community. Something that makes it more personal like you actually attempted to know them instead of saying you were doing one of these automated LinkedIn things where you were going to try and connect with a hundred people. Start with the message and get your connection, then send some relevant information, maybe your company has done some blogs. Send some to them, “I thought this would interest you because…” and make it relevant to them. After you’ve done a few of those, then ask, “Could we have coffee?” but attempt to start a real conversation like you would if you were networking at the chamber or at a leads group or at a show together.

Gina Stracuzzi: Whatever those things are that we used to do, I don’t even remember anymore [laughs].

Kendra Lee: Right, because everybody is so quick to say, “I can connect with a whole bunch of people and I’m going to get lots of leads, I’m going to get a hundred connections a day if I do this on LinkedIn.” But it’s like you said, I don’t think it’s working.

Gina Stracuzzi: Denise said that was very helpful, and thank you. We have a couple of comments and a question from Ginette, one of them was in relationship to what you were just talking about. She said she wants to be transparent so she does want to signal her intent to connect, because they’re in business. She just doesn’t want to be duplicitous, which I get. Her question is, “Are women taking the subservient role and risk being perceived as the administrator?” Then she said, “Have you ever heard of Cunningham’s law? People like to be right, by offering something even if it’s wrong, they want to correct you.”

Kendra Lee: I would never do that, I don’t like the perception. I have to say that I am a strong woman, I have always been strong in my career so I have not struggled, even when I was at the bottom of the totem pole, with being perceived as being subservient. I would never say something I know is wrong so somebody could correct me, I feel like that’s already putting yourself down. I might say something that would get them thinking or that they might respond to, not necessarily controversial. I would be much more prone to share something that would be a new idea that would get them thinking or a recommendation that they may not have considered than to say something wrong and get them thinking. I would look at it coming from that point of strength. What would you do, Gina?

Gina Stracuzzi: If I was in front of somebody that always had to be right – and I have been and I really can’t help myself.

Kendra Lee: When they need to be right, let them. I do a lot of, “Yes, and…” with people like that. “Yes, and have you thought about this?” “Yes, and what about…?” Not putting them down, “A different perspective might be…” A lot of leading them into the next part of the conversation.

Gina Stracuzzi: That’s really great advice, Kendra, the “Yes, and…” because it gives them their due and then sets you up to show them the error of their ways or give them that new piece of information that you want them to have.

Kendra Lee: The new piece of information, I’m not going to try and correct them. It’s interesting because I was on a call with a client that we are coaching and hiring salespeople for. Many of our clients are business owners who started their business as technical experts, they’re the experts in what they do and they don’t know about sales and they’re getting ready to hire a salesperson. His opinion of salespeople is not high, the coach wasn’t going at it as hard as I wanted her to, to say, “You go in with that opinion and you’re going to fail.” When I jumped into the conversation it was a, “Yes, and have you thought about this?” or, “If you talk this way, this is how you’re going to be perceived and I know you’re really not this way.” The guy is just a wonderful person, he just wasn’t portraying himself really well at that moment. So not trying to put them down or put them in their place, just expanding the conversation for them, getting them to think another way.

Gina Stracuzzi: Does that help, Ginette? She said, “Like yes and.” Chel says, “Go to their bus stop, then walk them to a new idea.” I like that, that’s a great analogy.

Kendra Lee: That’s perfect.

Gina Stracuzzi: That’s it for the questions at the moment.

Kendra Lee: Shall I share with you more things that we had said we were going to talk about today?

Gina Stracuzzi: Absolutely.

Kendra Lee: I love all the questions, we can stand here and just talk the whole time.

Gina Stracuzzi: I think we could

Kendra Lee: One of the other things that you want to be aware of that can hold women back is that they often don’t want to interrupt when they’re prospecting. It’s funny, I told you how I hated cold calling and I’ve long since gotten over it because I’ve changed my perception that it’s an opportunity to talk with new people, to hear what they’re doing in their business, what they’re challenged with and see if we might be able to help them. I like having that conversation with them so my whole concern about picking up the phone went away. Often with women, what will hold them back from actually picking up the phone is that they’re thinking, “I’m going to interrupt someone.” This is the subservient thought, “I don’t know if this is going to be a good time.” It’s funny, anytime I speak on prospecting I’ll get the, “When is the best day to call and when is the best time to call?” Men are asking because they want to make sure they’re going to reach the person, they’re going to get through. Women are asking thinking, “I don’t want to interrupt them, I do want to reach them but when will they be most conducive to having a conversation?” Same question coming from a different angle.

By the way, I say just pick up the phone and call but best time is still early in the morning, lunch time and later in the afternoon, those are still the best times to potentially reach people. However, be aware that more and more people start their days really early, work really late and go through lunch. Schedule it on your calendar and just do it, just call but don’t worry that you’re going to interrupt people. If it makes you feel good to send an email first because it gives you something to talk about or send a video email first, do it. I don’t care what you start with, it doesn’t matter if you do the phone call or you do the email but I will tell you, you do want to call. When you do, they get to hear your voice, they get to hear how interested you are in talking with them, they hear your confidence and none of that can come through in an email. If you do a video email, it can. My recommendation is if you’re doing a video email, call and tell them, “Hey, I’m sending you a video in an email, watch for it, here’s what the subject line is.”

Gina Stracuzzi: That’s a very good thing, especially when people have to be so careful about links because you do get those emails from people you supposedly know and you find out they’ve been hacked or whatever the case is. That’s a very good idea and it gets that double touch.

Kendra Lee: I know there are people that will read their emails on their phone or they have voice-to-text but that’s still a very low percentage. If you’re calling someone on their cell phone, you have a higher probability. If you’re calling them on an office phone line, the chances are they’re actually listening to your voicemail. I still like calling for all the reasons that I just mentioned, but don’t worry about interrupting.

Gina Stracuzzi: They’ll send you a voicemail if they don’t want to talk to you which raises a good question. What do you suggest people put in a cold call voicemail?

Kendra Lee: Similar to the email, and it’s fun because when we do our Coffee with Kendra webinars and we talk about prospecting, sometimes I have our senior sales consultant do it with me because she trains our prospecting and she and I have very different approaches. For me, I talk to their voicemail as if I were talking to them, it’s very conversational. I still focus on what I said about the email, it’s going to be what the problem that I suspect they may have is, and the fact that I have an idea or recommendations or something to share. But I’ll also talk to the voicemail, if this is the fifth time I’ve called, “You must really be busy, we have not been able to connect. However, I still would like to talk with you” and my voicemail will sound just like that.

Gina Stracuzzi: I think don’t ramble, be short, direct, upbeat. That way people might be more likely to take your call than if you go into a long diatribe about what you want.

Kendra Lee: Right, you sound fun, you sound interesting, you sound confident. When they hear all that, are they going to call you back? Maybe not. They may more likely respond to the email that you send or they will take your call the next time. If you send them a calendar invitation for a 20 minute meeting, they may accept the calendar invitation as well.

Gina Stracuzzi: Julie wants to know how you send a video message.

Kendra Lee: Video messages I’ve started to do a lot more of and they’re very effective, you can use them throughout the sales process. There are some free apps that you can go get and they’re all on your PC, the one I use is Vidyard and then there’s also Loom, both of them have free versions. They’re a piece of cake, you sign up and it’s basically going to say new video, create it, go. You can connect it to your Outlook or you can copy and paste the link into an email. I will create the video and then send it off to them. Keep it short because you know when you go watch a video, you don’t want it to be even a minute and it really depends on where you are in the sales process.

Last week I did a video for a supplemental proposal to a client, just something short but I didn’t want to just send it – I have a rule where you don’t send a proposal without talking to them. He needed it fast so I did a video where I took him through the key elements, it was five minutes, and sent the video with the short proposal so he could see what I was thinking.

Gina Stracuzzi: That’s different, though because it’s an explanatory video.

Kendra Lee: That’s different than a prospecting one. A prospecting one is similar to your voicemail on why you want to talk, same idea.

Gina Stracuzzi: Julie says, “Amazing, thank you.”

Kendra Lee: You’re welcome. If you want to go to our website, Julie, last week I did a whole webinar on using video in the sales process and that’s in the event section of our website if you want to go listen more.

Gina Stracuzzi: Are those the Coffee with Kendra?

Kendra Lee: Yes, they’re the Coffee with Kendra webinars that we do.

Gina Stracuzzi: Is there a day of the week and time of day that you do those or are they just on-demand?

Kendra Lee: We do them on Fridays at 1:00 o’clock Eastern and we run them about every three weeks. Our next one is March 12th, we did one just last week on using video emails in the sales process.

Gina Stracuzzi: Mark that down, March 12th so you get more Kendra.

Kendra Lee: Thank you, Gina. Can I show the four ways? I’ll just show this really fast, I want you guys to know the four ways that we tend to sabotage ourselves in prospecting.

The first one is that we will acquiesce to whatever the gate keeper tells us rather than try and gather more information. I don’t really want to say push back. Men will push back but just ask more questions, get more information, try and break past the gate keeper, don’t just take what the gate keeper says.

The other is tone. You’ll notice Gina and I are talking with you with a very confident tone at a pace that fits what we’re talking about, we’re not rushing. Women tend to have a softer, more sing-song voice and you’ve all heard the women that do that uptick on the end of a sentence where it’s actually supposed to be a statement. They’ll go up at the end and it ends up being like a question instead of a statement. Women do that all the time, men do not.

Gina Stracuzzi: I was just thinking about a guest we had on about a month ago, she has a product that she developed called VoiceVibes and it will analyze your voice. You would do your sales pitch into it and it picks up on the tone, the speed and the uptick, it’s an amazing tool and it’s really eye-opening.

Kendra Lee: That would be interesting to try. If you’ve got somebody who has a problem with tone, that may be something to look at.

Women tend to say “um” a lot. I don’t care if you put a post it with “um” with a hash mark through it but whatever you do, get rid of the “ums”. It destroys your confidence. Then the pace, I know of one of the salespeople that one of our consultants is coaching who talks at such a rapid pace, repeats herself and just keeps going. There’s never a pause for someone to say anything. Watch your pacing. In her case, she also apologizes as she’s going, women will do all of those things and it hurts us, so don’t do that.

Gina Stracuzzi: When we get nervous, it happens.

Kendra Lee: We shared what the things are that women tend to do. If you have women on your team or you are a team lead, even if you have someone you’re mentoring, there are four steps you can do to coaching them to be more successful at their prospecting. The first one is to have the woman put herself in her prospect’s shoes and really think about who that prospect is. I will always say, “Picture your prospect sitting across the desk from you and envision either a client or a prospect that you’re working with” – and now because of video that’s really easy to do – “Then Identify what their problems and feelings are” like we were talking about at the start. What problems do they have? How do they feel about that?

Gina Stracuzzi: That’s where women really excel.

Kendra Lee: Exactly, and women listen really well so they can hear the problems. Once you’ve done that, now have a roadmap of a strategy that you’re going to use to follow up, and I have a free resource that I’m going to tell you about that will give you a roadmap. Having a roadmap instills confidence that it’s okay to call with a certain level of frequency or it’s okay to send an email or a video email, it’s okay to send a calendar invitation because women tend to need permission, unfortunately. Provide a roadmap and then – this is the most important one – have your woman salesperson or yourself envision a powerful woman, someone they really respect and model that woman making those calls. You could role play together, you could put together a bullet and script but be that woman and make your calls as if you’re that person that you really respect. What’s interesting is when you think of that person, your whole demeanor changes.

Gina Stracuzzi: It dawned on me, there’s coaching strategies and we’re looking at coaching women. Briefly, if you’re coaching men, do a lot of these still work as well? I’m just going to throw this in now: if you could think of one piece of advice to leave our audience with that they could implement today, that would be great.

Kendra Lee: Yes, these will absolutely work with men. They have different challenges that you’re going to address but these same steps 1 through 3 fit. Envisioning the prospect, knowing what the problems are and how that impacts them from a feeling perspective, then having a strategy. This part I would be careful of, having them envision a man they really respect, because they could get too aggressive. Steps 1 through 3 are the ones I would use and step 4 would be to have you role play it with them to practice to make sure they’re not getting too arrogant.

I have some free resources. This is a strategy you all can use, these are all on our website but the Bloodhound Prospecting Strategy gives you that cadence and then I just love our 60 Ways to Prospect Remotely, it’s a blast. Read it, pick a few and use it.

One tip that I would give you today is it doesn’t matter that we are in these dynamic roller coaster times, there absolutely is business to be had and we’re seeing an uptick in people realizing they need to do things, they need to make changes. My one recommendation is as you are doing new business development, focus on problems that people have right now. Don’t try and get them to think more strategically about what they’ll need a year from now because they’re focused now. Focus on the issues and the problems that you’re seeing people have right now and that’s how you’ll get in the door.

Gina Stracuzzi: We do often get men who sit in on our webinars. Bill today said in regard to step #4, “How about envisioning yourself as a respected and accepted colleague?”

Kendra Lee: Yes, and choose a colleague who is respectful of others and not arrogant. You know what I mean because you can see it in some people that get – and women do as well – very proud and full of themselves, we don’t want that. We want someone who’s respectful of others and relates well with others. Bill, I like that, choose someone who has strong relationships with their colleagues and their clients.

Gina Stracuzzi: Respected for the right reasons. Sometimes people get respected because they do big numbers and it doesn’t matter how they get there. Maybe not everything should be emulated. For everybody that’s here today and importantly, those that are listening, the best way to reach you would be LinkedIn?

Kendra Lee: The very best way is email, definitely connect on LinkedIn and put a message in. Remember, I told you I’m screening more carefully now than I ever had before [laughs] so put in that you attended this so that I know, but you can absolutely reach out through email or pick up the phone and call. I will tell you this is our main number and a man answers, so don’t be put off [laughs].

Gina Stracuzzi: For the people listening, it’s kendra.lee@klagroup.com and the telephone number is 303-741-6636. Thank you, Kendra, this has been amazing.

Kendra Lee: Thank you, Gina, it has been a lot of fun and I have really appreciate all the questions that everybody shared.

Gina Stracuzzi: This has been great. I hope you’ll come back again because I know you have more to share.

Kendra Lee: Thank you, I’d be happy to come back.

Transcribed by Mariana Badillo

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