Episode 137: Ask the Right Questions – Chick Herbert

Predictable Prospecting
Episode 137: Ask the Right Questions - Chick Herbert
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Can you get better performance from your team just by asking questions? Asking the right questions can build and strengthen your management coaching skills and allow your team to perform at their highest levels. Today’s guest will explain how the ability to ask the right questions can help you tap into the human potential of your team.

Chick Herbert is a Des Moines executive who’s come up with a process that he calls question-centric coaching. Listen in to hear what Chick has to say about pinpointing where people on your team are struggling, asking the right questions, and motivating your team.

Episode Highlights:

  • Chick’s background
  • Chick’s working relationship with Brad Williams
  • Pinpointing where people are struggling
  • Asking questions that get people to contemplate their own struggles and behavior
  • The frustration of witnessing ineffective leaders
  • What about Chick’s process motivates people
  • Tracking progress
  • Whether styles of coaching differ based on sales roles
  • Extending knowledge to other team members
  • What to do when you’re not used to asking questions
  • How to use silence
  • The value of preparation
  • Truth and ground truth


Chick Herbert

It Begs the Question

Chick on Twitter

Email Chick: Chick.Herbert2@gmail.com


Marylou: Hello there. It’s Marylou Tyler. This week’s guest is Chick Herbert. Chick is a local Des Moines executive. Many of you know, I part-time in Des Moine, Iowa. I wanted you to meet Chick. The reason for this podcast interview was for those folks who are in management positions who are always trying to eke out high-performance from their team. Chick has come up with a powerful process that taps into the human potential of your team and does so through the art of asking questions. 

We all know in sales and in sales process, I harp on the ability to ask good questions is going to allow us to advance prospects through the pipeline. Here, the ability to ask good questions allows you to build and strengthen your management coaching skills in your company and allows your team to perform at the highest potential. You’re really making a difference in lifting performance but also improving morale. Here he is folks, Chick Herbert.

Chick: I grew up on the south side of Des Moines and went to Iowa state. I actually did work in northern California. I worked for a semiconductor business. Technically, the manufacturing was in Singapore but Milpitas was the headquarters. I lived in Mountain View, then worked in Milpitas, then I worked for Motorola in Chicago, and got lured back here many years ago by a small boutique consulting firm. I never thought we’d live in Des Moine but absolutely so happy we’re here. I do love the city.

Marylou: Yeah. The first week we’ve got here, I thought, “Oh, no. This is not going to work,” because we were food-centric in San Francisco. When we first came here, I think we went to Court Avenue Brewery or something. I don’t remember where we were, but although the food was delicious, the presentation was not something that I was used to and the plates were so huge. I thought to myself, “This is not going to work.” But it all worked out. We’re definitely happy with all the choices around. Our […] exploding with great restaurants. I’m pretty happy.

Is the NCMIC Group, is that who wooed back? And is that where you’re still are? What’s the relationship there?

Chick: No. The woo back was about 25 years ago. Most recently, I was with Wells Fargo for 13½ years. I had three very different jobs. For the first four years, I ran a global sales team and worked across a fairly large-sized organization within Wells Fargo. I’ve always had a passion for developing people. I’m an engineer by degree, so I’m technical in nature but really enjoy people. The book blends both of those concepts together. 

Then, I was responsible for the leadership development and the executive succession planning or talent planning for a big chunk of organization of Wells—it was about 60,000 people—looking at who the next leaders were that we thought could be the CFO of the mortgage company or the next head of the credit card business, what do we need from a strategic move and experience perspective, from a skill development, all the way down to frontline managers of what do we need to do to better equip them to lead their teams. Loved it, but I’m not an HR guy. I’m a business guy with a penchant for people.

About six years ago, I moved back into the business on the executive team of one of our consumer lending businesses. I was responsible for strategy, customer experience, design thinking, sales, and sales relationship stuff. During all of that, I wrote the book. I had to get approval from the corporate council of Wells to do that. I’ve take vacation and I do speaking and consulting around the book and other things. 

NCMIC had hired my co-author to be the new CEO a couple of years ago. Mike had me in doing my work here, and then they approached me and said, “Why don’t you just come to work for us?” That’s not why I do in any of these. I’m just really passionate about it and loved it. It allows me to continue to do what I’m really good at. Also, have my day job which, most of the time are stuff I’m good at but not always. They just made a really unique offer. I came here six months ago and they created a role on their executive team. It’s a new position in the organization. I still do my speaking and consulting on the side. I have that.

Marylou: Interesting. That’s awesome. The relationship with Brad Williams just because Brad is Brad or have your work cross paths?

Chick: Very good question. Crossed paths in the short time I’ve been at NCMIC. One of the things I’m helping lead the effort to get our sales, we have six different businesses within our walls. All very independent. All do things differently. No common language, no methodology from a sales strategy. We’re implementing Salesforce and I’m leading that effort as the executive sponsor. We’re also done a lot of sales development work. Concurrent to that, we created an enterprise selling strategy. That sounds more complex and glamorous than it is. This is all small business selling, not anything extremely complex. 

Brad’s company, Dextra, is who we hired to implement sales. They’re the outside consulting firm that we hired to be the Salesforce implementers with us. Brad, has a really talented young woman named  Christina Roeder and she is his business development person. Christina was a great partner and has a real passion for developing sales process. She was very involved early and we asked Brad if he wanted to come and sit in on a session that she and I co-facilitated. I just struck up a relationship with Brad and we’ve had a lunch a couple of times. He had approached me on my interest of joining the two of you and some of the other folks doing your workshop.

Marylou: Oh, okay. I was wondering how these all fit together. Brad is a connector, there’s no doubt. He said, “Marylou, you must get to know Chick,” and I said, “Okay.”

Chick: He oversold that.

Marylou: He’s really amazing and fun but we have yet to work together. We’ve gotten to know each other really well, we had a number of different meanings over the years, but we have not worked together on a client project, for sure. This was the first attempt after many many years of talking about it, of putting together a workshop and understanding from that point of view of how we can orchestrate it, who we should invite, who should be leading it. It was a first attempt for us to bring together our talents which actually worked really well. I do top of funnel to opportunities and need to opportunities to close in this particular workshop. It was really a fun time to get together, try it out, and see how it worked out.

Chick: You were happy with everything?

Marylou: Yes. I do these already. Just getting in the door part. His piece was something I heard him do before. It was nice to give the audience the entire picture because I literally stopped at opportunity. You know from your now dealing with Salesforce, it’s really an engine for opportunity to close. It’s not necessarily a business development engine. In fact, it’s horrible at it. I very seldom use or worry about Salesforce other than as a data repository to store the metrics, the sales conversations wrap-up, and all the things we need on top of funnel so we have our waterfalls in place. That’s the extent of my usage of Salesforce.

Chick: I’m excited. I have not ordered your book yet but I am going to do that. I really want to learn more about your work. Brad speaks very highly as do others and would just love to understand that a bit more because I spend a lot of time in that space as well. I don’t know if you even had a chance to look through the PDF that I sent you of the book. 

One of the interesting things that I think as an engineer, I was always taught that you need to understand where the constraint is in the process. If you’re not working on the constraint or the place that you’ve got the greatest difference between demand and capacity, then you’re not really making meaningful improvements.

My experience on the sales side is a lot of sales leaders, (1) they’re not very good. (2) They use a one-size-fits-all approach. They will go into a team and have everybody focus on improving at this stage in the sales pipeline, when not everybody needs help there. Other people may have a constraint in their pipeline in the next stage. By opening up the capacity or improving their skill on that one area, all you’re doing is causing a bigger backup on the pipeline at the next stage.

I love to get your feedback as you read through those chapters just to see if it aligns with how you think about things, if you disagree with it. I just love that in the conversation.

Marylou: I will definitely do that. I think, with me, it is all about relative position in the pipeline. We have intra within the stage and inter from stage to stage metrics that aligned with the wrap-up telephone conversation or email. Whatever conversation they’re having whether it’s email, social, direct mail, or whatever. It allows us to pinpoint the scorecard process where people are getting stuck. The roleplaying, huddles, and the daily day in the life of the business developer is modified based on where we’re seeing the data tell us that we’re struggling, or not working hard enough, or trying to cheat the system and gain the system a little bit.

Chick: […] exactly the same thing.

Marylou: Yeah. I love that you’re approaching it from the form of a question.

Chick: Yeah, because my experience is leaders will go in and tell people what to do. “This is how I did it because I was a gunslinger and the best salesperson that ever worked in the door of this company.” All of that is not digestible or meaningful or practical for somebody who has a completely different style. How do you ask questions to get people to contemplate what their struggles are with executing that particular stage? How do you get people to recognize some of their own behavior that’s getting in the way instead of just telling everybody how to fix it? By doing so, you’re not creating any capacity and buy-in from that person.

I’ve worked with Fortune 50 to small private firms, every different functions, and dozens of different industries from healthcare to financial services. One of the areas that I think are the worst coaches are the people on the sales world. It’s a lot of telling and not a lot of asking, not a lot of listening, and not a lot of diagnosis as to how they can help.

Marylou: Or it’s that sink or swim mentality. That’s the way I grew up in sales. I, like you, am a computer software engineer. My career started by walking in the office one day, noticing it’s a little bit quiet. Then, the phone rang. It was my boss up in Sunnyvale—I worked in LA—saying, “Hey, Marylou. We’ve had some issues, as you know, with selling this disruptive technology. We fired all the salespeople and now all you guys are sales. Good luck!” That was my introduction into sales. 

Luckily, I had some good fortune of working at Xerox first. They were heavy on training, especially if college grads, even though I was a computer science major. They put me through their sales training program. The Xerox sales training program at the time was topnotch. Probably, it’s still is if they have something. I got training in an area that I was a little bit puzzled as to why they would want an engineer to be taking to sales training. They explained it as, “Look, your clients are the employees at Xerox. You work in the data center, they’re your clients, and there are certain techniques and certain questioning habits that we want you to internalize so that you have a better relationship with clients. They’ll use the data center more and they won’t outsource to others.” “All right.” 

Remembering that helped me rise above this feeling of dread and driving home thinking, “My life is over. How can they do that?” It allowed me to think, “All right. I’m a process expert, I’m an engineer, I build operating systems, so I should be able to figure out at least step one.” That’s how I got started. As I leverage the knowledge I had with process, I look at things, relative position, I looked at things, “What do I need to pass go? What materials? What data do I need to collect?”

Then I, being a student and an engineer, we’re always studying, trying to better ourselves. I read everything I could from everybody I could on the subject and knew I didn’t need to necessarily work on the process side of things because I had that. What I needed was the skillset and the mindset. The mindset was the hardest thing for me to grasp. We solve problems as they come in. We don’t necessarily have a habitual way or reaching out to people. We’re more reactive than proactive in some cases.

That was a big aha moment of how to turn on our proactive engine inside of my head so that not unlike brushing my teeth, I would make those 40 calls. We didn’t have email at the time, there was no internet. Or send those direct mail letters or sit in the parking lot at six in the morning when you […] CEO to come in so you can have a conversation, stuff like that.

I really want to understand what drove you from being an engineer in process, then attacking it from question side of things knowing that there is not a one-size-fits-all? When you’re dealing with people, you’re dealing with a myriad of things that can go wrong. Tell me what was that moment where you said, “I need to get this information down on paper”?

Chick: It’s a great question. I think it was the frustration of witnessing so many ineffective leaders in all functions but sales included, that talked a good game but didn’t have any method of their madness, and would just go around and be the cheerleader and get people fired up. In one of my roles, I talked about being responsible that helped create a defined sales strategy and approach.

Probably similar to a lot of things that you’ve done, my approach was not to go tell them what they’re doing wrong and tell them this is how they need to do it right, it was to ask questions. It was very consultative in nature and it would be a simple question of, “All right, Marylou, you’ve got this territory in Northern California. Tell me about who do you call on? What kind of prospects fit into your sweet spot? What’s your strategy of covering this territory?” I was continually shocked at the responses that would be, “Well, I do a swing up to Sacramento once a month. Then, I always go over and I hit this area, and then I like to go down to this area. I just do that cycle on a monthly basis.” That was about as deep as the strategy went.

Over the course of the engagement, I would ask them a lot of questions. As I ask them, I’d ask followup questions, and they would come with the conclusions themselves that that’s probably not a very effective strategy. I’ll say, “Would it be helpful if you thought about opportunities this way?”

One of my stories I talked about if you’re going fishing, what’s the most important thing? People say the bait, the rod, the strength of the line, the reel, the time of day. I respond that all of these are really important but the most important thing when you go fishing is you go fishing where there are fish. Are you taking the time to think about where you’re going to fish and have the highest likelihood to get some bites?

Through the whole process, we developed a common sales strategy that we would define and agree to. When we go to implement that, some leaders were much better than others at coaching and leading people around the new process. The ones that were effective were the ones that invoke that same strategy. It was, how do we get people to take a different approach, recognize their job as not to just tell people, “Here’s your unattainable goal. Go get it and swim,” but to understand the metrics, understand the process, understand where people—my terminology— one-size-fits-one, not one-size-fits-all.

Marylou: I love that.

Chick: What does Marylou need? What does Chick needs? Is it skill? Is it knowledge? Is it at that? How do I use questions to develop those different needs? It was an evolution, I guess, which would have been a shorter answer for you, sorry. 

Marylou: No, this is great. I’m sitting here thinking, I know when I go work with clients. We’re all gung-ho to put in something new, we go through the training, and we start working on the new thing, improving it. Then, I leave. And then, it just falls apart. What in your process motivates them to continue on? This is not a set it and forget it thing especially with people. People are so variable that you just can’t set it and go. You have to monitor it and nuance it. How does this part of your process when you’re working with clients with managers, with leaders, how do you instill that sense of honor to continue on with this so that the whole person is growing as a result of it?

Chick: The linchpin is the leader or leaders. You just have to have somebody at the appropriate level in the organization that is going to work at the right altitude—not too high, not too low—to ensure that it doesn’t go by the wayside. Quite frankly, I think we give people way too much leeway to self opt-out of things. To me, it’s not a full democracy. There’s always the, “Well, what about your top producer if they don’t want to do it?” You have to decide if you’re willing to held hostage by them and the damage of them not participating. If you’re okay with that, then so be it.

You can let people openly and upwardly do everything to sabotage the process. That to me is not acceptable. Part of that is from accountability. “You can stay. If you don’t like it you can leave but there’s not a door number three that you can stay and ditch. That’s not optional path. What do we need to do to get you on board?” What I found is, the thing that motivates most people to continue is, it works. If people are making money and being successful, that’s the best way to create that accountability and desire to continue moving forward.

Marylou: But you also, in the book, indicated ways to track progress, so there’s some visual components to this so that it’s not all theory. Whenever I hear management and getting the people side of things, my head goes a little woo woo sometimes because how do you process or codify people, their behaviors, and their attitudes? You’ve really shown here and demonstrated that a little bit of process, a pinch of process, a little bit of management training, and questioning go a long way coming together to create a process, a system, and a method you can maintain. 

Chick: Yeah. In a lot of companies I’ve done work with and I’m sure this is true for you, you become a bit of the company bartender or people will confide in you. One of the things that I believe causes a lot of unrest and organizations is that people don’t know what’s expected of them. They also don’t know how their manager is going to show up and which person is going to be there today. Is it going to be nice Chick who’s really happy and giddy? Or is it going to be angry Chick who tells me I’m doing everything wrong and I’ve got to do better? It would appear that neither of those reactions are predicted based on me, it’s really Chick’s mood. 

A lot of this does come down to the discipline and the predictability of the managers. For example, I sat in hundreds of meetings across the country where a manager would be meeting with an employee doing their one-on-one. The employee would simply be sitting there as a passenger in this conversation. The manager would just do a verbal download of all of their wisdom. No questions, no confirmation of understanding, no questions around how they’re going to apply with their hearing, none of that. 

A little thing that I always incorporate is at the end of a one-on-one, I encourage managers to say, “All right, Marylou. Can you give me a quick summary of a recap of what we talked about and what we agreed to?” Just by doing that, I’m shifting it from my agenda to, “Now, it’s your stuff.” When we come back together, the first thing I’m going to do is, “Hey, Marylou, can you please provide a quick recap of what we’ve talked about last week and what we decided.” Just to get the discipline where we’re not going to talk about at once, then it’s on the next fire the next week. A lot of it comes down to getting people to apply.

I’m not a big believer that we need a lot more training. I believe we need a lot more coaching. Training is acquisition of new knowledge which is great and very important but if I don’t apply it, which is where the coaching comes in, it’s not going to happen. 

If I’m working with a salesperson to improve their ability to close deals and they’re not an aggressive personality, they’d have a hard time asking for the business. We’re going to talk about how they can overcome that, how can they close in a way that they’re comfortable, and then, they’re going to go off and do it. If I can observe them do it, that’s great. Then, we’re going to debrief and talk about how that went, what worked, did you get the deal or did you not get the deal. It really comes down to how that is applied. All of that to me, goes back to the manager and asking questions to get people to think at that level. 

Marylou: The sales roles in many companies could be split amongst business development team. There could be account executives who close the business, account managers, et cetera. Are there different styles of coaching that you recommend based on what types of sales role they’re in?

The reason why I asked that is I’m finding, from a business developer point of view, where they’re not necessarily working smaller number of deals because they’re trying to find people to qualify and get to an opportunity. We’re talking to a lot more people. There’s a little bit more habit involved.

Does that require a different type of manager than say, someone who’s going to be working with account executives and getting to close. Or can one person, with your training or with this particular method, do well in all facets of sales?

Chick: That’s a really good question. I’ll do my best to answer it. From my experience, what excites me about what we wrote about and what I talked to people about, is it’s universal and applies whether it’s a relationship management role, a business development role, a CFO role, a product management role, a healthcare administrator role. The questions applies everywhere. It can be done by the same person.

I do think, the aptitude and the natural strengths of a person are going to influence their interest. If somebody is really technical and likes to have a lot of things coming through the pipeline quickly and the sales cycle is quick, that’s very different than an enterprise strategic selling model that is going to take 18–24 months to close. I think natural attributes of the leader and their interest in that product has a bigger impact on the success or failure versus their ability to use this approach in question-centric coaching. The types of questions it would be asked, the pace, and the number of the batch people had in those different stages, that certainly is going to vary, but the underlined premise would be consistent.

Marylou: Interesting. The book is broken out into four or five sections?

Chick: Four sections.

Marylou: Four sections. The first section is all about the fundamentals of coaching. Is this for the person who has already coached or is already in a management role? Could it be for aspiring coaches and managers? For example, I have a lot of folks right now; my clients. They have done really well in the sales development role. The next progression for them, growth within the company is go to a lead role. I start freaking out when I hear that because they don’t have any type of any management training. Would this be applicable to someone like that who’s thinking about? They’re naturally starting to ask good questions of their clients, of their prospects. I’m curious if this is something that people who are not really yet in the coaching or leadership role to take in and be able to apply.

Chick: Great question and yes. The one thing that I’ve never seen is any data that correlates leadership or coaching effectiveness based on level or tenure. In fact, I think organizations put too much credence in the number of years of doing something. Is it that I’ve done this job for 20 years and every year, I continue to grow and learn—you talked about that curiosity and that learning desire as an engineer—so that I continue to evolve? Or am I doing things the first year and I’ve repeated them for 20 years? Those are two different people. I find a lot of folks would fall in that category. There’s the percentage of the tail of the distribution better than growers and the learners.

I think that whether it’s somebody who’s been leading for a while, quite frankly, I don’t equate them as being an effective leaders just because they’ve done it for a long time. I think this is really good for everybody. I consider myself successful. I consider myself the level that I worked at my day job is in the executive level, but I still follow the same principles. I’ve seen enough of peers or similar level people that are really bad at this stuff. I’ve seen enough trainwrecks to know that it’s not universally done.

Marylou: And we don’t help, either, because here I am telling you that I’m worried about high producing sales executive going in the management. I have nothing to base on. I just have a fear of it.

Chick: But you’re right. You’re absolutely right. I think the attributes that make someone a great producer are not always the same attributes that are going to make them a great leader. If you’re a great producer, it may just be tenacity. It may be, you’re going to hold on through. It could be a number of things. Now, you’re shifting where you need to be responsible for not managing other people but developing other people. That can often be in conflict of how they’ve been successful. I share the same concerns and I’ve seen plenty of failures were the top producer becomes the leader. What I see is one of the things we talked about in the book, is working on the system versus working in the system.

Marylou: Yeah, I saw that in chapter three in the book. It’s a great section to learn about, especially for me, alleviating my fears. I just don’t have a lot of insight into what to look for, for a good producer, as you say—excellent producer—who wants to grow within the company. The natural progression is going to be, at some point, into management. They have it down, at least in my world, because they’ve proven over and over again the routine is habitual in nature and that they’re consistent and bordering unpredictable. For the most part, very consistent. To take that and then plump them in to a role where now they’re responsible for team performance and stragglers, how is that going to work with a personality who’s so driven and so disciplined to be able to pinpoint the areas of lead in the rest of the team?

This first section of the book is really great. Essentially, […] to be okay with. You can definitely get there but there are some warning signs. There are some key things that you really need to consider first before you make that leap. 

Chick: Absolutely, and will they fundamentally enjoy the activities associated with that role? I think people do aspire to move into a different role. My personal opinion is, organizations sometimes undervalue an individual contributor role. Not everybody needs to aspire to be a leader of people.

What I think happens is most people that are in that mindset or the organization just promotes them because they were the best at whatever they were leading person. They spent a lot of years crafting their ability to underwrite or to run technology independently. Now, they move into this role and they continue to spend time. In fact, they’re working on versus in. Those people, I think, it’s really natural for them to dive back into the system. Instead of helping, “You and I used to be peers, I’ve got promoted, now you work for me.” What’s really easy for me to dive back in and rescue a deal that may go bad that you’re involved in, but not bring you along from a development perspective simultaneously. I saved the deal but I don’t build any capacity in you.

It’s easy for me to do that because that’s where I spent my career. I wasn’t the best deal maker that there was. That’s not the sole responsibility. It’s also to develop people and doing it or telling them how you did it is not going to build capacity in other people. It just doesn’t work. These people can reject it. It’s like if you’re selling, you don’t just go in and tell somebody about all the great things your product does. You start with questions. You start by diagnosing what’s going on in their world and how might you be able to help them. But that’s not where you begin. 

Marylou: Looking for those gaps to see if there’s a good fit there. Truly, a diagnostic process. You’re right. I’ve seen it over and over again in my 30 years of working with sales people as coming in, saving the day, yet there is no instruction of what happens after that. How did that happen? What just transpired? Yes, you saved me but how can I do this on my own going forward? What’s the teaching moment or moments here?

Chick: Exactly, right. I would profess that, that teaching moment doesn’t serve with the person you saved the deal going into a two-hour dissertation about what they did. I profess that it would be good to say, “Marylou, what did you observed? Let’s take a step back and reflect on how we got into this position in the first place. When I came in, where were we? What are some of the things you observed that I did that were beneficial.” It’s being very deliberative about that debrief process so that learning take place. Not just jumping in the car or an airplane and parachuting into the next crisis.

Marylou: Right. The other thing I liked about this whole process is that we can also chronicle these dialogues, these exchanges in the form of a playbook or something that can help the rest of the folks coming up through the ranks, to look at certain situations or to listen to certain situations that happened, how that was overcome, what the teaching points where, and what are the next steps were as we march people down that pipeline.

I think that’s another area that this is beautiful for is extending that knowledge out to other team members who may be struggling, not right now, but will be someday. I think with all the tools we have now, shame on us if we’re not doing essentially those interviews or debriefings, like you’ve said. After the fact, who understand what went well, what we can improve on, what we have done differently, how did you feel about that, what would you do differently, what do you think the next stage or step is, et cetera.

Chick: That’s exactly right. I was an industrial engineer. I was taught plan, do, review. You talked about the debrief and that’s exactly the mindset. The same thing, ideally, let’s plan this. I’m going to go on a call with you. Let’s talk about our roles. Let’s talk about how we’re going to approach this. Again, if I’m the manager traveling with someone on my team, I’m going to be asking questions about, “Tell me about what you’ve identified as why we might be a good fit. Tell me about how they’re currently managing, whatever it is, our product does. Tell me about what research you’ve done about the organization and whether they’re doing well.” It’s getting people to think about that preparation, not just telling someone you need to be prepared. I think, we make far too many assumptions that if we just tell people something, they automatically know what needs to be done. In some cases that’s true, but not always. 

Marylou: This goes to our prospects, too. This is so correlated to our prospects. We don’t assume that they’re going to understand which option is the best for them, that they’re going to somehow feed through these three different things and figure it out. We have to demonstrate for them and start helping them understand which of these three options best fits them.

Chick: Exactly right. You’re absolutely right. One other point you talked about where you said you can document it in a playbook which is what I spent a good part of my career doing. We’ve done things with sales leaders, bringing in divisional sales managers or regional sales managers and talking about understanding where each person on their team, their sales producers, where they struggle in their pipeline—similar to what you get them to do using the data and the metrics—but then, talk about how have you coached people around a constraint at this stage? At the close stage? What have you done? What kind of questions do you ask?

Not only do we build sales playbooks, but we build sales coaching playbooks so that they’re not all having to reinvent the wheel. There are only so many different things you can encounter. Let’s capture those, understand those, and identify the types of questions we want to use to help build people’s knowledge and skills in those particular areas.

Marylou: I think the biggest aha moment for the listeners, I’m hoping, is this is not a passive process. This is a very proactive, very engaged process. It requires you to get out of that command and control mode, and more in we’re a team, we all have valuable input, we’re all coming from different areas of knowledge, different experiences.

I got a message today from one of my clients. They wanted to have a document that explains some type of hardware configurations. It was asked by the sales executive. “Where is this document?” I naturally said, “You know what? Great. This is a perfect opportunity for you to research what all of the different hardware options are and let’s present it in our next huddle so that we can talk about the strengths and weaknesses of each. We can talk about whether it makes sense to do a campaign around this because if we’re getting this question a lot, it’s something that we want to hit as we go into a conversation or maybe create should ask questions document.”

It’s taking that spin of, “I’m going to do this for you,” and putting it rather, “Great question, great need, let’s have you managed that, collecting the data, and present to us—you’re a salesperson—the why behind which one over the other.” They’re glad to do that but it’s just so not natural for people to take that and run with it.

Chick: I agree. What a great way to engage your team, engage a person, and give them a stretch assignment so they can develop some additional skills. If you’re going to present something, you know as well as anybody, you become a master of it. I’m not sure what the negative or the reason you wouldn’t do that other than it’s just isn’t how we normally do things.

Marylou: Sometimes even I as a consultant, it’s faster for me to do something, but I’m realizing—this is before, now I’ve had this great book to actually reinforce that—it’s helping me really understand that yes, it may be 70% of what we want, but it’s 70% that I’m not doing either. It’s basically 70% done, we’re going to find tune and finesse, and make beautiful the other 30%.

By the way, we have a conversation around it. We talked about experiences we’ve had with clients. We talked about all these things that help us understand the story behind the need for this. It’s just opens up the ability for the reps to have deeper conversations, more meaningful conversations; it’s just a winwin. Taking that mindset and saying, “Yup, this is great. You’re in charge. Go figure it out. Here’s the stuff that you need to do. We’ll put it together as a team and make it a production document, in this case, that we can use to run our sales process.”

Chick: I think it’s a great opportunity for that leader. Even through the development of this document and the discussion with the sales team, as a leader, I’m going to stay engaged with that person. I’m going to coach them through that process as well to the extent that it’s going to depend on the person.

Rather than saying, “You know what, here’s what you need to do first,” which is what most commanding control leaders would do, my approach would be, “Walk me through what you see in the four steps of this process entailing. How are you going to start?” Not because I don’t trust them, but because by asking that question, it helps me assess their critical thinking skills in an environment or in a process that’s different than what they do everyday. 

The whole point of the book is how do you develop the critical thinking skills of your team? How do you improve your position of leverage as a leader? Your team is better equipped to solve problems on their own and they don’t need to be coming to you in a panic. This is a great opportunity to do that outside of the traditional pipeline or whatever it is that they’re doing.

You’re right. It’s a different habit that has to be formed. You have to get in the habit of asking questions. Quite frankly, I think you need to prepare for those conversations differently. Most managers just wing it because their conversations were pretty surfacy. If you’re not used to asking questions, write down a few questions that you can ask just to get the conversation started. You’re not dictating it and you silences your friend or ally and not the enemy.

I think leaders that do try and ask questions, if the other person doesn’t respond immediately, they feel compelled to fill the dead air and give them the answer. I think asking a good question, silence is the evidence of a good question because it means that they’re contemplating. Let them contemplate. Ask the question and let them think about it.

Marylou: Your section two of the book really helps us understand the fundamentals of questions. The basics, but also the strategic use of them which is very helpful. I think because we’re all kind of like, “How do I ask a good question?” or “What’s a good question?” we now have to do these. We should know how to do these or at least work on doing these to that implication question process that we learned with the spin-selling methodology that helps us help people think outside the box, challenge us a bit, and pokes them a little bit. We know how to do that pretty well, but we’re dealing with our own people, so there’s a way to approach that and I think you’re right. Listing them all down, getting an understanding of what the outcomes that you’re looking for, and then backing it up into what types of questions you could ask to understand how they view that outcome is really important.

Chick: I agree. Some people are very inquisitive and just naturally ask questions. There is a strategy of using questions. It’s learnable. You can repeat it. I always tell leaders that it isn’t their natural habit. You don’t need to have 50 questions in your toolbelt. I ask the same questions often. Back to being predictable, by doing that, if I asked a question every time we meet, over time, you’re going to come in prepared to answer that question. I’m changing behavior by me asking questions.

Marylou: I love that. Actually, this section of the book, for those of you, is great to hone your skills for asking questions of your prospects, for business developers, and the AEs alike. This is really great section of the book that helps you think about the complexity of the questions, how to approach them from a relationship and trust point of view. Really valuable information regardless whether you’re doing this type of coaching or managing, but also if you’re dealing with working with people you don’t really know very well and you’re trying to get some engagement out of that conversation.

We move to that section three now, where we’re actually implementing. This is where we’ve really start seeing the value of preparation as you said. You prepare, you execute, you review. That’s so great to see that. This is the actual execution. Are there certain areas there that you wanted to point out to people that you think really differentiate what you’re trying to do in this book versus some of the other management books that may be out there for sales management? Are there certain things within the section that you want to highlight for us?

Chick: Yeah, a couple of things. One would be, you have to get to know your team. In most cases, at a deeper level than you know your team today. You may know them because you worked with them for 10 years. You know about their family. But, for example, have you ever asked them a question of, “What motivates you? What part of your role do you think you do the very best and why?” So, trying to get underneath the skin and have more meaningful conversations.

Interestingly enough, I’m doing a session with some leaders in healthcare. There was a survey or pre-assessment of their skills in different areas. I think people have the tendency to overrate the level of trust with their team, their ability to communicate effectively, and their overall leadership skills. Part of this is getting to know people and having a high trust relationship where they’re willing to speak the truth to you. I found in a lot of places, that does not happen. 

I’ve got two sons that served in the military and one’s still in. He’s an intelligence analyst. I love the term “truth” and “ground truth.” Truth is the truth that you hear from your command and control station. Ground truth is what’s going on in the real world. There is often a very big difference between these two. Talk to a leader like, “Oh no. In my team, everybody’s engaged. They’re doing a great job. I’ve got a really high trust team, great communication, we get to talk to people.” I’m like, “Absolutely not.” I’m afraid to say anything. How do you get to know the team and get to that one-size-fits-one so that you really know how you can help people improve?

The other thing would be, especially in the sales world which I know a lot of your listeners are in, understanding where people have a constraint in their sales process and using your tools to identify that so that you’re applying a one-size-fits-one instead of a one-size-fits-all. Really, that diagnosis of where to coach, if you’ve got metrics which a lot of organizations do, that’s great. I found even with those metrics, they don’t really use them from a coaching perspective. You use them from a managing perspective saying, “We’ve got to get more deals through the pipe,” but they’re not doing anything to help figure out how to accomplish that. Telling somebody they need to increase their production and asking some questions what’s getting in the way are very different conversations.

Marylou: Right. Like you said, they do have data but maybe not specific to location in the pipeline, necessarily, where things are getting gunky and stuck. That’s what I found. Like you’ve said, they’re looking at global overall type numbers, summaries, instead of detail, inter- and intra-stage metrics that helps us understand where the conversations are failing.

Chick: Yeah, that’s a great point. I see so many leaders working in the wrong altitude. They’re working so high. The analogy that I was using in another meeting today, I was driving in my car this weekend and I was in an area that I didn’t know. My GPS and my car was zoomed in really close, maybe a quarter mile around my car. I was panic-stricken because I didn’t know what direction I was going. I didn’t know how to proceed. I zoomed out, went up, and got context to some big landmarks. “Okay, I got it. Now I know where I’m going.”

If I’m zoomed way out, it doesn’t help me because I can’t even see the road I’m on. If I’m zoomed in too far, I see way too much detail of the road and everything right around me. I’ve got to figure out that altitude is a leader that I need to work at to effectively transform my team and my organization.

Marylou: That’s a great analogy. I love that.

Chick: Thank you.

Marylou: It really focuses on the fact that it’s a variable. This whole thing is variable in nature from the standpoint of people variable. There’s a lot of areas where you can stockpile knowledge and assistance because we’ve been down that road before in some other capacity with some other person and are able to now create a library of, “Here’s the things where we’ve been. Here’s the obstacles we’re able to overcome. Here’s some of the new challenges we’re working on now. Isn’t this fun?”

Chick: You have to look at it.

Marylou: Yeah, exactly.

Chick: It’s all changing. That attitude is different for every person on the team because of what they need. To me, that’s what makes all of these fun. You really have to be in the game to understand what people need, at what time, and that is always evolving. People are growing and changing,

Marylou: The book is It Begs the Question, Chick Herbert, Learn how the best managers drive performance through Question-Centric Coaching. Now, is that your terminology? Question-Centric Coaching? QCC?

Chick: Yes, it is. 

Marylou: Great. What’s the best way that we can continue. We’ll get the book, of course, on Amazon. Are there other ways that we can get to know you, your process, your training, what’s available for us to learn more. Where will we go do that?

Chick: I do have a website. It’s not a super robust website but it does have quite a bit of the information on it. The website is questioncentriccoaching.com. It’s a long URL but questioncentriccoaching.com and you can also purchase the book there. It talks about the premise in some of the other services and the work that we do.

Thank you for the opportunity to spend time with you today and talk about it. I’m very passionate about it. I didn’t write the book because I aspire to write a book. I wanted to write the book because a lot of people said, “You should write a book to help more people do this because it works.” It’s not something I turn on and turn off. It really is in my DNA. I’m passionate about it. My goal is to try and eradicate bad leadership. There’s unfortunately too much of it around.

Marylou: I was also going to say that’s lifelong work that you’re talking about now.

Chick: It definitely a little too aspirational. 

Marylou: I’m great at process, I’m a little bit not too sure about people, but obviously for me, I’m the coach. I’m a consultant. I’m dealing with people all the time. Having those tools in your tool chest of how to get people to engage, how to get them to do the work that needs to be done at hand, have fun doing it, and enjoy it. Why don’t you come back later if you’re a consultant like me for that next project? It’s really great to have this side of the knowledge, understood, practice, apply, and really this is a planning, execution, and review process. It’s never ending. 

I love the way that the book is laid out because you can really consume it and start applying it. It’s like a manual or a reference book which is a nice way to write a book. Go back to it. I’m sure you have a lot of readers who’ve earmarked sections of the book where they go back and review all the time. That’s it. That’s the mark of a good book, for sure.

Chick: That is nice of a compliment one could get, so thanks. And that was the intent. It wasn’t to have it be a big theoretical book that you didn’t know what to do. I’m a pretty simple person. It’s a pretty simple book with some icons and graphics to convey points. The intent was to give people that they can literally use tools in their very next conversation. It’s as simple as that.

Marylou: Wonderful. Chick, thank you so much for your time. I very much appreciate it. I’ll be sure to put all the links and things on Chick’s page everybody. For those of you who are driving and don’t have time to write something down, don’t worry, it’ll all be all up there. The book is, again, It Begs the Question-Learn how the best managers drive performance through Question-Centric Coaching. Thank you, Chick, so much for your time.

Chick: Thank you, Marylou. I really enjoyed it and appreciated the opportunity.