EPISODE 475: Sales Professional Onboarding Strategies with Will Fuentes and Andres Peters from Maestro Group

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[EDITOR’S NOTE: This is a replay of the Creativity in Sales virtual learning session sponsored by the Institute for Excellence in Sales on January 9. 2022. It featured an interview with Will Fuentes and Andres Peters from Maestro Group.]

Find Will on LinkedIn. Find Andres on LinkedIn.

ANDRES’ TIP: “As you start reflecting on whether or not you want to make a change, ask yourself, “Am I running away from something or am I running towards something?” Because if you are running away from something, then really understanding what this next opportunity is, is it more of the same or is it really truly an opportunity? Am I running towards it? Really spend some time reflecting so that you don’t become that no-show, or you’re not that person that is constantly switching jobs because you haven’t figured out exactly what it is that you want to do with your career.

WILL’S TIP: “Get really good at asking great questions. It is, to me, the number one skill that I see out there that really makes a difference, and understanding the second, third, and fourth level questions. Do question trees. I would challenge everyone to do one a day. It is game-changing to be able to be prepared for the answers you’re going to get and be able to really facilitate a conversation to get to that impact, become a great question-asker, incredibly curious.”


Fred Diamond: We’re very excited, we have two people from Maestro. We have Will and we also have Andres Peters, he’s the Chief Learning Officer and Director of Delivery. We’re talking about onboarding, and there’s so many things going on right now with the need to properly get your salespeople integrated right into the company. We all know the term, The Great Resignation. Of course, 60 Minutes just did an episode where they call it The Big Quit. It’s really challenging right now for companies to show themselves as optimal places, not just for salespeople, but for employees. That’s what we’re going to be talking about today.

Will, it’s great seeing you. It’s even better to see your partner here, Andres, who’s the expert on onboarding and expert on getting people involved with your company and really optimizing teams. Good to see you both. Andres, let’s get started with you. Just give us the basic definition, what is onboarding and what are some of the trends that we’re seeing with onboarding right now?

Andres Peters: Onboarding for most companies usually has one definition. How do you get people started, operating, and performing? But really, from my perspective, onboarding is three really distinct processes. You’ve got something called pre-onboarding, which is what happens after someone has accepted a position at your company. Then what are the steps that they take in order to get to day one? Then you’ve got onboarding, which starts at day one. What are those experiences? What are those processes that they have to complete, the paperwork? That typical HR stuff that people do. Then there’s ongoing success. How do you take what they’ve learned through their onboarding experience and help them capitalize on that so that they can become more successful quickly? A lot of times companies focus on this onboarding aspect, this day one, and most companies actually only focus on that paperwork and those administrative processes.

In fact, there’s been a lot of studies out there where they’ve surveyed companies to see like, “What are your focus areas?” Actually, more than half, around 58% of companies say that their onboarding is just focused on process and paperwork. Think about it from your own perspective. Imagine starting this new job, being all excited, and then being told, “You’re actually going to only spend two days doing your compliance training and getting your payroll set up. Then you’re off and running.” That is not an ideal experience for anyone.

What I’ve been seeing a lot of companies doing with regards to onboarding is changing it from becoming just a process into more of an experience. When you translate it into an experience, then you’re thinking about all of not only the hard things that people have to do, which is the paperwork, the process, understanding the company, but then you get a little bit more in the warm and fuzzies. How are they feeling about the experience? How are you engaging them early? How are you getting them excited about the world that they’re about to start? They’ve taken a huge risk in going to your company. How do you make them feel comfortable with having taken that risk? By giving them an awesome experience at the start.

Fred Diamond: Will, let’s talk specifically about sales right now. You’ve worked with hundreds, if not thousands of organizations that bring on salespeople. You’re a tremendous sales trainer. What are some things that companies should be aware of to get sales professionals onboard right away? I remember when I worked at Apple computer a long time ago, we almost had like a year to get up to speed. Now you don’t have that anymore, and it hasn’t been that way for decades. But it takes some time to get people up and running. What are some of the things companies should be thinking about to ensure that they get their people off to a good start?

Will Fuentes: I think there’s a couple of things. Number one, that pre-onboarding period is absolutely critical in how you communicate and how you follow up. The expectations for a great sales professional is that they do great follow up. Imagine you’re at the final contracting stage and your sales professional decides not to reach out over the next week or two as the contract gets finalized. You wouldn’t accept that. Why do you accept it when you offer a salesperson? You want them to exhibit the behavior, so you want to start that very early.

Then on the onboarding side of it, it’s absolutely right, the paperwork, all that stuff is important. But having them understand their role, their responsibility, their territories, who to go to, really giving them a good map of the organization and understanding, “When you’re working a deal, here’s how the flow of information happens. Here’s how you get the things that you need in order to be successful.” I’m hearing stories of individuals that were making $50,000 a year being offered positions at $105. Being constantly recruited, I’ve heard stories of individuals continuously being recruited after they’ve told someone, “I’ve accepted a job.” They say, “Well, go see what onboarding is like. If you don’t like the territory, if you don’t like what’s going on, give us a call. We think we’re a better match for you.” Imagine competing with that. You’re competing with that constantly. You want to set them up for success.

Fred Diamond: Andres, where do you see companies go wrong with the pre-onboarding stage specifically? Will makes a really good point there. There’s so much competition for great salespeople. There’s actually competition for good salespeople. Forget about The Great Resignation, just in general, getting good people on your sales team is… Will and I know. Actually, someone’s just chimed in here. Dennis actually says, “It’s still hard getting good people for great companies.” We work with some of the best companies in the world and they’re chimed in. Where are companies getting it wrong in the pre-onboarding stage?

Andres Peters: It’s interesting because most companies, they expect people to do a lot of their own due diligence before they start. What’s the company history or what’s their mission? What’s their vision? What are the values? People are either leaving another job or busy with other things. They’re not spoon-feeding, or at least creating an environment for them to get to learn and see themselves at this company, even after they’ve accepted a position. Where they get it wrong is that they aren’t giving them an experience beforehand to get them to see themselves at that company on day one.

In fact, Will was mentioning that some companies will continue to recruit, even after someone has started. Some companies continue to recruit even after someone has accepted a position. There’s been studies that have now shown that there’s a higher percentage of no-shows on day one. People have accepted an offer and just don’t show up because they’ve accepted a counter offer, but just didn’t tell their new employer, or their ex-new employer, if you will. How are you engaging with them beforehand to get them to really embed themselves and see themselves at that company so it makes it harder for them to want to leave before they’ve even started?

Fred Diamond: Will, we have a question for you here, a question which comes in. Rick says, “What does Will think about the strategy of not showing up?” Will, you’ve worked with salespeople, and a lot of times people ask me, “How do I have a great sales career?” Our friend Kristie Jones said, “Be at a company for five years,” because it takes you time to learn the company, learn the market, learn what you’re selling, if you will. Do you recommend this strategy, knowing that the great salespeople or any decent salesperson is going to have a long tail career? Is that approach going to bite you in the butt at some point by accepting an offer then not showing up? Does the word get around? This is more advice for the sales professional on how they need to be treating the employers that are bringing them onboard.

Will Fuentes: I had an interesting experience recently. I interviewed someone for a position and at the end of the interview he said, “Am I going to move forward?” I said, “No, and here’s why. Here are some things I think you need to work on.” A year passed, we went to another client, and who’s there? This person that I had given this advice to. He raised his hand and said, “Hey, what I did is I took your advice. That’s how I got this position. These are the things I’ve worked on.” That’s what a real sales professional does.

Very similarly, a real sales professional has the conversations that are difficult. If you’ve hired someone who doesn’t show up, be okay with that actually, to be quite honest with you, because you didn’t want them working for you. This person can’t have the professionalism to call you and say, “I got a better offer. I’ve decided to do that. It’s best for me, for my family,” whatever those reasons may be, but this wasn’t a great salesperson. You actually had a bad hire that you got saved from. For the best sales professionals out there, I’m telling you, if it crosses your mind to not show up, don’t do that. You’re already down the path of not being good enough.

Fred Diamond: One thing that we see a lot is when I bring on leaders to be on the Sales Game Changers Podcast, or as members of the Institute for Excellence in Sales, of course, we look at their LinkedIn and we see that the great ones, there’s always the outlier who might have been at the same place for 20, 30 years. But in most cases, they went from this company to this company after a number of years, not like every year, but the leaders, maybe five, six years, then they went to another place, or maybe the place was acquired. They’ll be around. The people get to those levels, the hiring levels, they have been around, and they will remember, and they will talk to your friends. You will be haunted if you do that type of behavior.

Andres, of course, we’re doing today’s show in January of 2020. Omicron is spiking. Most people are still in the virtual “hybrid” mode, in most cases, virtual still. I’m looking at both your backgrounds. It looks like you’re home, as am I. How has this shifted? We’re probably going to stay in virtual for a while. How has the hybrid model shifted?

Andres Peters: Well, I think first off, most companies are more open to hiring people that aren’t located or near their corporate location. They’re more open to virtual hires, meaning they can sit anywhere in the US. It’s opened them to a broader talent pool. But what the shift has been, especially in onboarding is that before, when we were doing it live, even if you had a bad onboarding, you could still create that connection, that culture, because you had people standing asking questions to other people that were near them. You had the opportunity to do a lot of that informal learning.

But now with virtual, most people only have set times in which they can ask questions because they either have a session for it, or they Slack someone and the person gets back to them two or three hours later. There isn’t that instant learning that happens. The shift has really been trying to create opportunities for people to connect in informal ways that are similar to what they were able to do in person. That’s actually one of the biggest challenges because most companies think that, “Let’s just do a quick happy hour,” where everyone’s just having a drink, and that’s culture building, but it’s not. It’s actually, how are you getting people to connect and get their questions answered as quickly as possible, especially when they’re starting? For salespeople in particular, you don’t want them to build bad habits. It becomes even that much more important to find opportunities for them to ask those questions and get them answered as quickly as possible.

Fred Diamond: Gina just sent me this note which says, “Research by Glassdoor found that organizations with a strong onboarding process improved new hire retention by 82% and productivity by over 70%.” I want to ask a little bit about who owns onboarding for sales professionals. This question is for you, Andres, and Will, I’m interested in your thoughts as Andres gives the answer here. Obviously it’s a role of, I guess, recruiting or HR, but I’ll let you answer that. I’m actually interested more in the pre-onboarding versus the onboarding, because it’s really intriguing for me, Andres, that you mentioned that there’s three distinct places. There is pre-onboarding, then onboarding, then of course once the person is live. Talk a little bit about the role of sales leadership.

Again, the reason I’m asking this question is the whole mission here is how do you retain and motivate top tier talent? The mission of the Institute for Excellence in Sales is helping sales leaders attract, retain, motivate, and elevate top tier talent. Give us some of your advice, then Will, I’m interested in your thoughts. What role should sales leadership play in the pre-onboarding phase?

Andres Peters: Just going back to what Gina said around the percentages. Gallup actually also did a study where if you have a good onboarding experience, your employees are 2.6 times more likely to be extremely satisfied in their role. That’s another data point to also think about.

I think that sales, the role that it plays in, especially in the pre-onboarding, it should be a collaborative approach. It shouldn’t just be HR owning all of the communications. HR should be working or partnering with sales because sales is going to be ultimately the group that will own that individual’s career or support that individual’s career. Having that messaging right, or having their point of view before that person joins, and understanding that, is really important.

Plus, when it comes to interviewing, they interviewed with all of the folks within sales before they got the role. Imagine getting one message from the people that you’ve interview with, and then you’ve accepted the role. Now all of the messaging is completely different, has nothing to do with what you had talked about. It’ll cause some level of cognitive dissonance in that person, like, “What did I just sign up for?” Having sales really partner with HR and what that language looks like and what gets communicated out is really important.

I would also add, working with HR to understand what can be communicated, as well as what can be sent to that individual. It doesn’t just have to be messaging. You can send that person swag, similar to what sales professionals do, give them articles, or give them case studies of the product so that they have a better understanding of the environment they’ll be operating in.

Fred Diamond: Will, to follow on to what Andres just talked about. What are some things you recommend to sales leaders to ensure that during the pre-onboarding stage that their people feel welcomed? I’m kind of curious as well. We hear a lot of information about what motivates salespeople, and we all know that it’s not really the money. How does all this play together? Because what we’re looking for isn’t really just performance, it’s actually long-term performance.

It’s cost so much to bring on someone new. We talked about the fact that you might do all this time and energy to find the right person, and then they don’t show up. Think about all the money that was just wasted, all the money, energy, effort, and other candidates that you didn’t go to because you didn’t properly bring this person on for however reason. Will, what is your advice for the sales leaders and what should they be knowing about to make sure that the people they bring on hit the ground running?

Will Fuentes: I think Andres hit the nail on the head. If there’s information that can be shared with them that isn’t necessarily proprietary, that isn’t something that can’t be shared outside the org until they’re officially on, I start doing that. I’m a big text person, so when I’m functioning as an interim VP and we’ve hired someone new, I start texting and just checking in on them, asking them how they’re doing, seeing what’s going on. Things that I do with my normal teams, I start to do with them so that they get comfortable with that and make them feel like they’re part of the team.

If there’s someone that I’m targeting to become a leader within the organization, I might task them, “Hey, send a message or two out to them to make them feel welcome.” If you guys can do a virtual coffee beforehand about anything that they may be nervous about, see if you can book that into your calendar. It’s a twofer. Number one, I’m making someone part of the team. But number two, I’m giving someone that is looking to be a leader some quasi-leadership responsibilities, making the team feel welcome. I think there’s just very small things that can happen.

I’ve heard from candidates that we’ve placed before and say, “Hey, the experience was pretty good, except I found it odd. I signed and then gave my two weeks and I was going to start and didn’t hear from anyone until my start date.” It’s like, “Yeah, that is a little bit odd. I’m surprised you didn’t hear from anyone.” You just don’t want people to walk into that experience. There’s just a lot of nerves. Make them feel as well as possible so that those first couple of trainings or events that you have for them, they’re really dialed in. They’re not just worried about like, “Is this right? Is this the right fit?” They feel welcome already.

Fred Diamond: We have a couple of questions coming in here that are pretty much on the same topic, which is, “What should the sales professional do to ensure that they hit the ground running?” We have some questions here. A question comes from Mick, a question comes from Nina, and they’re very, very similar questions. Let’s talk about that for a little bit. It’s a two-way street. Whenever people ask me, “How do I have the best sales career? What should I be doing, Mr. Diamond?”

The first thing I always say is, “Get to know your customer’s market. Intimately know your customer’s market.” But the other thing I always say is that, “You’re the president of your career. You’re the CEO of your career. You may be going in to work for a great company as an account executive or whatever it might be, or SDR or something, but it is your life. You got to treat your career like your business.” Andres, you go first, give us some of your thoughts on what should the sales professional be doing to take responsibility to ensure that they get onboarded properly?

Andres Peters: I think one thing that’s really important is to reflect on what really motivates you as an individual, as a professional, and see how those motivations align with your new company. It’s really important. If you value certain aspects of the job that you had before, in order for you to be successful trying to see how you can mirror that in your new role, understand what your non-negotiables are within how you operate.

Then the other thing I will say is you were hired for that position for a reason. It’s your background and experience. Don’t neglect that when you’re joining and feel like, “I have no idea what’s going on,” because you do have experience that you can lean on and see how your past experience can be translated into this new role. That’s the only way that you’re going to be able to make those connections stronger. Because a lot of times the onboarding that you may receive is again, very processed, or if it’s a new industry that you have no background in, you can still lean on, “This is how I used to do it in the past. How is that different from now?” Then you just connect the dots from there and fill those gaps, rather than just starting from scratch.

Fred Diamond: I spoke to a young sales professional early this week who’s starting a new job next week. He’s worked for some great companies and he said, “What is your advice for me to hit the ground running?” I said, “You know what? You’re starting Monday morning. I would say, relax this weekend. Don’t go out. Don’t go party. Don’t get drunk. You want to be there 8:00 in the morning on Monday. You don’t want to miss a start for some reason,” and he’s starting virtually as well.

I said, “Take it seriously, the whole thing. Not just the 8:00 to 5:00 that you’re “on the clock”, but everything around you so that you are the best performer and athlete you can be. Again, it’s your career and you’re responsible for the company being successful.” Will, you’ve worked with thousands of sales professionals. Give us your thoughts on what should they be processing to hit the ground running day one.

Will Fuentes: I absolutely agree with you, make sure that you’re your best that first day and every day moving forward. I would take a couple of days to think about what has made me successful. “When was I most successful? When did I hit the most amount of quota? What was I doing then?” Start to write that down, memorialize, you got some time to think. Then think about the things that made you unsuccessful, how did you get distracted? Keep those as notes so that as you go through your career, you can recognize when those things are happening.

As you start a new job, what I would tell someone is the questions you should be asking of the most experienced, most successful sales rep is, “What websites are you reading to stay up on the industry? Who do you see as our biggest competitors?” Go visit those websites and learn from it. “What newsletters are you subscribing to?” Start to get that tools and those assets for you. Then I would also ask questions like, “What did you wish you had learned earlier about the company or about your job?” Start to really get that great information.

Then finally, go through the buyer’s journey. As you’re getting onboarded, go through the buyer’s journey, read the blogs, read the assets, and think about how your buyers experience it. When you’re ready to hit the ground running, you’ll have that perspective, which it’s really hard to get once you’re in the mix. It’s really hard to take yourself outside of it. That’s really my advice.

Fred Diamond: If you don’t mind, I want to bring on Gina Stracuzzi. Gina runs our Women in Sales program. Let me send her an unmute request. I think she’s going to have something interesting. Gina, are you there?

Gina Stracuzzi: I am.

Fred Diamond: Gina, again, thank you for all the work you’re doing for Women in Sales and the leadership that you’re doing. I know you have a comment or two for Andres and for Will. This is Gina Stracuzzi. She runs the IES Women in Sales Leadership Forum, and she’s doing some amazing things. By the way, Will, she’s also a big fan of yours. She enjoyed your podcast that you did for us a couple of years ago. Gina, why don’t you ask your question here or bring up your comment to Andres and Will?

Gina Stracuzzi: Thank you. This is such a fascinating conversation, because part of the forum, the women that go through the forum, they have to come up with a leadership project for their company to elevate them, give them visibility, and help show their strategic thinking. One of the things that comes up at least four or five times project-wise in each forum is better onboarding. These women are taking it upon themselves to help the company improve their onboarding process.

One of the things that they talk about is that there’s not a clear direction on how they move forward and move upward in the company. What professional development opportunities there will be. Will they get a mentor and how can they progress their careers within the company so that people can see their path? They’re not going to see it on day one, but six months in, if they’re still questioning, “What are my opportunities and how do I move forward?” This being addressed in onboarding seems like an aspect of it. I’d love to get your feedback on how often that comes up and what you all recommend to your clients for this.

Fred Diamond: Thanks, Gina. Andres, this will be our final question before we get to the final action steps. We talked before about long tail career. Give us your thoughts on how can companies retain people by proving and showing to them that, “We’re here for your success. Not just for your immediate onboard, but for the next 5, 7, 10 years”?

Andres Peters: To answer Gina’s question, I think it’s both on the new hire and the company to really work together to determine what that path can look like. On the new hire, it’s really being grounded in what their purpose is, what drives them to work. Then for the company it’s working and understanding how their mission and values really align to that purpose. By having that understanding that individuals can then set goals that align to that purpose, and then also meet the strategic objectives of that company. It’s also incumbent on the company itself to really set up those that will be managing the performance or those that will be mentoring the new hires up for success. How are they being trained to have these coaching conversations? How are they being trained to manage performance?

A lot of times a lot of these leaders are folks that have either been hired and/or promoted based on their deep technical expertise or their deep expertise in sales, but not necessarily in their ability to manage people. Investing in people’s ability to manage others and humanizing their roles a little bit more is what’s going to help that onboarding experience be that much better. Because you’re having those conversations early on and the people that are having them are equipped to have those conversations.

Fred Diamond: Gentlemen, thank you so much. I want to acknowledge you both for the great work that Maestro has done. We’re based here in Northern Virginia, the DC area, as are you, and I’ll meet tons of people. I’ll ask, “Who have you used for sales training?” Maestro comes up not infrequently. Will, you’ve made great penetration out there with the company and the work that you’re doing, so good for you. I’m really glad that you brought on Andres, because it looks like it’s a critical part of helping companies be successful. Not just from the sales side, but in all aspects of their business. As we like to do with the Sales Game Changers Podcast, I’d like to ask for your final action step. Will, why don’t you go first? Something that the sales leaders and sales professionals listening today should do to take their sales career to the next level.

Will Fuentes: I think I always give the same advice, which is you got to get really good at asking great questions. It is, to me, the number one skill that I see out there that really makes a difference, and understanding the second, third, and fourth level questions. There’s a tool that you can use. It’s called Tensai. Go to gotensai.com. You can do question trees there. I would challenge everyone to do one a day. It is game-changing to be able to be prepared for the answers you’re going to get and be able to really facilitate a conversation to get to that impact, become a great question-asker, incredibly curious. That’s the way to do it.

Fred Diamond: Andres, bring us home. Give us your final action step for the sales professionals listening today.

Andres Peters: I think this is less around onboarding and more so for those that may be considering making a transition in their job, because of the amount of recruiting that’s happening. As you start reflecting on whether or not you want to make a change, ask yourself, “Am I running away from something or am I running towards something?” Because if you are running away from something, then really understanding what this next opportunity is, is it more of the same or is it really truly an opportunity? Am I running towards it? Really spend some time reflecting so that you don’t become that no-show, or you’re not that person that is constantly switching jobs because you haven’t figured out exactly what it is that you want to do with your career.

Fred Diamond: Thank you both. That’s a really good point there, Andres. Are you running away from something or running to something? If you’re based perhaps in Nashville, you should be asking that question as well. Once again, I want to thank Will and I want to thank Andres for being on today’s Sales Game Changers Podcast. My name is Fred Diamond, wishing everybody a great day.

Transcribed by Mariana Badillo

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