Managing Up: Collaborating WITH Your Leadership - DeJuan Brown
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You're listening to the Sales Success Stories Podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve. To learn more, visit us at top1.fm. Here's your host, Scott Ingram.

This bonus episode of the Sales Success Stories podcast featuring DeJuan Brown's presentation titled Managing Up, Collaborating with Your Leadership from the 2021 Sales Success Summit is brought to you thanks to all of our summit sponsors. Thanks to Outreach, Vidyard, Revenue Grid, Quotapath, Scipio, and Gong, you can still get access to all of these video presentations on demand, as well as the slide decks at top

Our next speaker is DeJuan Brown. DeJuan is like the OG-est OG I think we have here. DeJuan was a star of episode six. So we're talking dang near five years ago. And he was the first speaker at the first sales success summit. So I'm thrilled to bring him back.

And this talk came from, DeJuan and I have become very good friends. And as we were catching up on some things and just watching him and the way that he has managed since that presentation, he has led teams and he's been on teams. And the way that he has managed both sides of that dynamic

is powerful and has gotten better over time as I've watched him. And so once again, I get to be very selfish. Like, just teach me what you're doing. And I figure when I need that, you all need that. This is going to be super valuable. DeJuan Brown. Thank you, man. Appreciate it. Mic check, one, two, one, two. Okay. All right. Hello, everybody. This is...

Hey, this is a little bit surreal because as Scott said, I've been a part of this community for a while. And so this is pretty much me having a conversation with family and friends. And obviously we're live streaming. So there's some people that we're inviting into the living room today. And I hope that this is a conversation that I can treat almost like a friend has just asked me, hey, like, how are you thinking about managing up? Which is what I'm going to be talking about today. Okay.

As with everything that I talk about, I hope it's more descriptive versus prescriptive. I'm not here to prescribe things to you and say this is the route to take in order to be successful in X, Y, or Z. These are just observations that I've come across over the years of my own career, a lot of them through failure.

like abject failure in some cases at accomplishing the end goal as it relates to the things that I'm talking about. And so this is another one of those things, right? When we think about it, I really love what Katie said around discovery as being a lifestyle and not a stage. I think that's going to be a really good pivot, to use that term again, into what I'm going to be talking about today. And so you can see the subtitle of today's talk is it's managing up, but it's actually collaborating with

your leadership, right? And that's critical in what I'm going to be talking about. And so when you think about managing up, I want to talk through definitions. First of all, does anyone know who this gentleman is? Socrates. And one of the things, what did Socrates say as it relates to definition? Does anyone know? You probably heard it quoted. Maybe you didn't know it was a Socratic quote. Maybe you did. Anyone want to gander?

I'll help. So Socrates said the beginning of wisdom is the definition of terms.

Right? And so you can't really have or we can't really have a good argument. We can't really have a good discussion around really anything unless we level set and recognize that we're talking about the same thing. Otherwise, we find ourselves in sort of an Inigo Montoya scenario where, you know, you keep saying managing up, DeJuan, but I don't think that means what you think it means. Right? My wife, who's probably watching, will love that because I haven't seen the movie, but they love it in my house.

Right. Unfair use of the of the of the example. And so when we think about the definitions of or how we think about managing up, there's such a variety that's out there. Like some people think of managing up as a way to almost control your leader. Right. Some people think of managing up as the best way to get to where you want to go in your career. The fastest. Some people look at managing up and say, when I when I manage up, it's me managing.

being able to help my manager to manage me better, right? And I, at some point or other in my career, have had all of these as my idea of what managing up meant, right? And sometimes to my detriment, sometimes it was helpful. But ultimately, what I'm trying to say is that there are a lot of ways to think about managing up. There are a lot of definitions that people have. And I want to level set and say, the working definition that I'll be working from involves some clear and I think important distinctions, right?

What are those distinctions? Anybody know who this is? What's that? Plato. Yeah. And Plato said a couple of things that I want to call out here as it relates to distinctions. He said he who is not a good servant will not be a good leader, essentially. Right. The other thing he says is there are two things that a person should never be angry with, that which they can change and that which they cannot change.

Right? Very interesting when we think about the idea of managing up, because to me, and the working definition that I have here of managing up is essentially the management of your relationship. I'm going to say with leadership, but actually this is like the management of life's relationships when we think about managing up, right? If we take what Katie said, which is discovery is a lifestyle, not a stage, right?

and we apply that to the way that we engage with all the relationships that we have in business, it doesn't stop because all of a sudden someone has the title of your manager, right? And so what I've sought to do over the course of my career, whenever I've spoken about anything, I mean, in fact, you know, talking about the first sales success summit, I think the title of my talk was sales success through service.

and taking this idea of servanthood and applying it and saying that this is a universal idea because we are humans and sales is a human to human contact sport, right? Or a human contact sport. There's not a lot of difference when I think about managing up because it's really managing your relationship with leadership or anybody such that your actions and behaviors are intentionally aligned with their known preferences for the benefit of all, right?

Now, that's a little bit different than some of the definitions I said I ascribed to earlier in my career. The definitions that I say I ascribed to earlier in my career were really self-centered. They were about D, the wand. Like, how do I get what I need? How do I get what I want? Right. And one of the things I said, again, back going back to, you know, to the first sales success summit is that the quickest and the shortest distance between what you want and getting there is helping as many people as you possibly can get what they want or need.

And I found over the course of 21 years or so that as a default, you also get what you want to need. And so managing up again is no different. And so what I'm trying to stress early from a definition perspective and from a distinction perspective is that there's very little distinction between helping your top customer or your top prospect get what they want or need through things like a lifestyle of discovery and through a servant-hearted, other-centric perspective

and Managing Up, right? Very, very little distinction there. And so I wanted to paint a little bit of a picture here to show

What I mean by that, right? And one of the other distinctions, of course, would be the fact that you're seeking to build relationship with your leadership. That's the first part of that definition. Managing the relationship such that you have a known understanding of the preferences of the person who leads you or the people who lead you, right? You've done this lifestyle discovery to understand, like, what are their proclivities?

Right. Are they a morning person? Are they rather are they better suited to have a conversation within the evening versus the morning? You know, is there a pre coffee your boss and a post coffee your boss?

Right. That's important to know. And if you're doing lifestyle discovery, it's something that you're going to pick up. And I hope that you're encouraged to do that after this or during this if you aren't already. Right. What are the what are the communication styles? Right. Are they are they you know, do they like asynchronous or they like something that's that's solid and set and stagnant on a calendar? Right. What are the things that they hope for? What are their objectives and goals?

Thinking about priorities, like priority one, priority two, priority three, are they in lockstep with the organizational mission that you know about? Their priorities, one, two, and three? Or has your boss determined that there's an alternate route through a variance of priorities to get to the goals that the company has? Like these are really important things to note, right? Do they like email? What are their communication preferences? How do they consume content?

Right. If you have a boss that hates email, but you don't know that and you consistently try to get on calendar, you consistently try to get on agenda through emails, then there's a disconnect there that you may not know about. Doesn't mean it's harmful to your career. It just means that it may not be as effective as you would like it to be in order for you to do what I said the definition, my working definition today of managing up is. Now, what's a clearer example of this inaction?

So here you have, this is the story of two people. One is named John, the other is named Jane, right? John and Jane work for the same leader,

right? This leader has said, hey, John, this is what I want you to do, right? We're thinking about bringing an ERP system into the organization. I need your help. Can you go out, do some research, compile some information, and get it to me? Now, this is Friday evening when she's asking this. Compile some information and get it back to me so that it'll help shape the decision that we make around ERP systems, right? There's John. You have Jane, who's

Given a similar charge, hey, Jane, we're actually looking for sales enablement platform. We'd love your help if you can go out and sort of figure out what's going on, what's the landscape, what enablement platform's out there for us to use and give me back some information so that I might be able to help shape the decision as to what sales enablement platform we use. Now, this is really, really benign, right? It's just an ask, right?

John is a guy who just doesn't believe in managing up like he thinks that it's a farce. Right. John believes that the way that you excel in your career is to simply put your head down, knock out the work, be consistent and your results will speak for themselves.

The outcomes will show. John has for 30 years been the first one in, the last one out, has worked extremely hard. There's nothing wrong with the work that John does. And so John takes this directive and John goes and does research, finds price points. John finds all of the functionality differences, the ways that these ERP platforms will work.

Puts together a report and emails it to the boss almost right away. So this is Friday evening. The boss gets that Monday evening. No problem.

Jane, on the other hand, takes the same request and Jane says, OK, it's Friday evening. I already know because I know my boss. Right. I've been doing discovery as a lifestyle. I know my boss. I know that Friday evening is not a good time for me to start asking the questions I need to know in order to actually be effective at finding out what we actually need. So Jane, in turn, says, hey, great. I'd love to do it. Real quick question. Can I set time on our calendars Monday morning to ask a couple of questions about the ask? And that's fine.

Boss says, "Absolutely. Do that." Jane gets into the meeting on Monday and says, "Hey, really want to understand what it is I'm looking for specifically. Why are we looking for a sales enablement platform? What problems are you hoping to solve? Where is this coming from? What are the pains that we have today in an organization that leads to this search? Are things like security important? What are some other things that are important?" Jane gathers this information. Does this sound familiar?

What's it sound like?

Yeah. So Jane Jane gathers this information. Granted, it's Monday morning because right. Her boss is not an evening person. She's recognized that she didn't send an email. So instead, Jane says, because she knows her boss hates email. She found that out by doing this lifestyle discovery. She says, hey, great. I have what I need to do the research. Is it OK if Wednesday morning we schedule another meeting and I'll walk you through whatever it is that I find? And the boss has said, of course, OK.

Right. And so Jane comes in and she walks her through it. In addition to just finding out the information based on the discovery that she did and asking more questions. Jane also said, well, let me go a step further, because what I want to do is I want to make sure that I present some potential options and thought for my boss around ways that are non-technological to help bridge the gap based on what she told me the problems were and what she was trying to go for and the objectives short, mid and long term.

Just for your review. And Jane presents that at a morning time, which is a beautiful time for her boss, and she knows that, in a way that she knows her boss loves to consume content, right? And without a lot of fluff and data because her boss is an advancer versus an analyzer. And she knows that as well. All the details will get lost anyway in the case of her boss. And so what is happening here is that both John and Jane accomplished a task, both were

Probably got a thumbs up, but there's something about the way that Jane accomplished the task that took into account who her actual boss was in that given moment that likely has a deeper, greater, and more impactful outcome. Would anyone disagree with that? Right. Now, would you say that John was trash at his job? Because John did exactly what?

John did exactly what he was asked. John kept his head down, got the work done, delivered the work and kept it moving. And John said, yes, my work will speak for itself. And I say, potentially John's boss says, your work does speak for itself. But apart from you accomplishing that work with who leads you in mind, it's probably whispering, right? Your work speaks for itself, but it could be whispering if it's not taking into account who it is that you know.

Now, I've heard some people say, as it relates to this, that sounds like, you know, sucking up.

It sounds like, you know, in this age where we're really about and high on extraordinary authenticity, especially in the workplace, bringing your full authentic self to the workplace, there's some kickback and pushback at times that says, look, if I am adjusting who I am and the way I behave and the actions that I take based on who my particular leader is at a given time, that's non-authentic.

to which I hope that what I'm going to say now offers you some liberation. Right. Because if you feel that way, then I want you to be freed from that, as I have recently, not that long ago, been freed from the same sort of thought. Right. Two things. Number one, your authenticity does not take a ding because you magnify or amplify certain aspects of who you are.

At certain times and you pull back on certain aspects of who you are at other times. Right. So that should be freeing. Right. I want that. That is the truth. Right. You are no less you, your authentic self, when you are being thoughtful about who it is you're engaging with, then you feel less of yourself when you're being thoughtful about who you're engaging on a sales call.

What if we were to draw the paradigm to say, hey, your boss is your biggest customer. Your boss is your biggest prospect. How then would you treat that?

your boss, how then would you look to do discovery as a lifestyle in your engagement? What would you want to learn about the way that your boss operates, the way that your boss thinks, the things that are pet peeves of your boss, right? And to customize, if you will, your response, behavior and actions on the basis of this knowledge is not an indictment against your selfhood. It's not an indictment against your authenticity.

Right. It's actually establishing your ability to take your authentic self and leverage who you are in light of who your boss is in order to get the best outcomes for yourself, your boss and your organization. Is that helpful? Good. So let's look at this gentleman here. Anybody know who that is? Y'all are two for two. Come on. Keep the streak alive. Not Pharaoh. Not King Tut. These are great guesses. This gentleman, his name is Tahotep.

He's the writer. He's the writer of something called The 11th Maxim. It is rumored to be, and it quite possibly is, the earliest recorded philosophy of all time. And one of the things he says here is, follow your desire as long as you live and do not perform more than is ordered. Right? And I have a story there. This is a good friend of mine. I hope he's watching because this story will throw him back. But

Do not lessen the time of the following desire for the wasting of time is an abomination to the spirit. Two things I want to talk about from this quote. Follow your desire as long as you live and do not perform more than is ordered. That seems to fly in the face of what I just said Jane did. Right. I said, Jane, in order. And in addition to just getting the research done, Jane also took some time to think through solutions to problems that had not yet been had not yet come up.

And to say, hey, here's some ways that we might be able to solve the problems that you say are P1, P2, P3, priority one, two and three outside of the technology that I've researched just for your review. That sounds like the opposite of what Tahoe TEP is telling us to do here by saying do not perform more than is ordered. Let me give you a quick story about what I actually mean and I actually take from this quote.

So there's a gentleman who, I won't name him, he knows who he is, we're still friends to this day, like really good friends. But we've been working together since 2002-ish, right? And we worked together from 2002 all the way to like 2014. And there was a point in my career where I was really, really vying for a leadership role. And here's my basis. I don't think I had finished under 225, 250% for several years in a row, right? And I've told this story on various places and various places.

And I had done a lot of extra work, right? Like I had actually gone out and created content. I had delivered trainings that I thought impacted the org really well. I was an open book as it related to best practices. How was I getting this stuff done? I never hit a thing. And so I just felt like I was a shoe in for the role. And then here comes my friend,

who was not really, he was never top of the pile as it relates to stack ranking on the sales side, you know, definitely share best practices, et cetera, et cetera. But there was this mismatch, I thought, but I didn't understand a key principle. And that key principle, I think, is called out here. Don't perform more than is ordered, right? That doesn't mean just wait until, like John, like, hey, here are the instructions, go do that. Yup, done, did it.

But it's something different, right? This is the confusion and then sometimes the conflation of activity with impact, right? Where I thought that, man, all of this stuff that I'm doing, right? I'm doing a hundred things. My friend and colleague is doing seven. Guess what though?

The seven that my friend and colleague was doing came from an understanding of the top seven priorities of leadership and what needed to get done in order to help them do their job more effectively. So in a lot of cases, the work that I was doing actually was putting work on the plates of my manager. I didn't realize that because they were self, they were self, you know, almost self projects, right? These are projects. I'm like, I can help here and I can do this and I can do that.

And in order for that to be facilitated, then my manager had to do some things to make it happen. So I was actually putting work on the plate of my manager. And one great Sage manager says, hey, as an individual contributor, you're either putting work on my desk or you're taking work off my desk.

And so what I was doing in all of my activity and all of the work that I was doing was putting a lot of work on the desk of my manager. I was making a lot of impact in places that didn't align with the priorities of my manager. And I mistook that for impact, the right type of impact that would actually move the needle and make my manager either more effective or remove things from the plate of my manager. But the things that I was doing was all secondary and tertiary to the work that my manager thought was paramount to our organization. Whereas my colleague...

Discovery as a lifestyle. He knew exactly what our manager needed. He knew exactly how our manager wanted it delivered. He had asked the right questions to understand, hey, here are the things that I want out of my career. What might I do in this organization, in your eyes, to actually move the needle toward that?

What are the things that I can do to help you as I understand what it is that you're going for and your objectives as a leader? What are the things that our organization needs? What part of that are you held responsible for? And where can I be helpful?

And so he might have done four, five, six, seven things versus my 100, but they were the right things because he had done discovery as a lifestyle with our manager and understood clearly what it would take to actually move the needle. Now, was this gentleman a suck up? No, he managed up really, really effectively. And I did not. And so he got the role and I did not. And I was a little bit salty.

I was a lot salty. That was years ago. I'm still talking about it today. I was a lot salty. Yeah, yeah. I'll stop. Okay. So the direction is also being moved along by the desires, the needs, the objectives, the goals, the proclivities, right, of your leader, right?

Managing up is just really managing that relationship in such a way that you're being intentional about understanding, like, who is this person, right? And what are the things? And then making slight adjustments, making slight customizations to your approach, making slight customizations to the way that you communicate, making slight adjustments to your own styles, right? Whatever that style may be for the benefit of the whole, right? All right. So let's see.

Let's see if I can get this going. There we go. Anybody know who this is? Aristotle. I heard it. This is Aristotle. And a couple of things that Aristotle said, the greatest virtues are those which are most useful to other persons.

And this is the selflessness that I'm talking about. And I think this is a common thread throughout all of this is just managing up is, again, if you take the paradigm of your leader or leaders as your biggest customer, your biggest prospect, or you take the idea that your leaders are human as you are. Right. And there are some things that that that differ from leader to leader.

Then if you are taking some of these principles that we're talking about here, this again, just borrowing from Katie, this discovery as a lifestyle, then there's a lot that you're going to be taken from the work that you're already doing. Like y'all are phenomenal at doing this work as it relates to your customers and prospects. That's why you're here. Right. That's why you've been on a podcast. You're phenomenal at doing that. But because I think managing up is not widely taught on a regular basis.

then maybe when it comes to our boss, we kind of drop all that we've learned as it relates to customers and prospects. The greatest virtues are those which are most useful to other persons and pleasure in the job puts perfection in the work.

Now, you tell me if you're aligned and this is, you know, we all we know that there are bad bosses. Right. We know that there are people who this this alignment will never be perfect. But if you're aligned with the priorities and the goals and objectives of your boss and you're adjusting your communication style and the ways that you approach and your behaviors and your actions just slightly accordingly, then you're going to have a lot less stress at work.

You're going to waste a lot less time because you won't be like DeJuan doing a hundred things which take time in cycles when you could be from an understanding and clarity perspective doing two or three things that actually drive the results that you're looking for and that your boss is looking for and that your organization is looking for. It's very much akin to doing a demo of a thousand different things that your product can do when really

two or three things shown after good discovery as a lifestyle would have done it. And so then we have lastly, oh, I went, sorry, went one too much. I'll end with this.

You have a decision to make. We all have a decision to make. Heraclitus said, no man ever steps in the same river twice for it's not the same river and he's not the same man. He also said it is not too late to seek a newer world. And he also said, let us not make random conjectures about the greatest matters. Don't do guesswork.

Recognize that you are changing, your bosses are changing. And in summation, I want to say this. Anticipate problems and actively work to prevent them. Be proactive at making your manager's job easier. Be reliable. Be productive. Customize your communication and work style to better align with your leader's preferences. Be willing and flexible.

Sometimes that means taking on projects that aren't front and center or sexy, but advance the ball on behalf of your leader and your organization. And then lastly, speak truth to power when necessary. Managing up does not mean being a pansy or being unwilling for conflict to happen. Conflict is necessary in order for advancement. That's it.

If you weren't in sales, you could just be up on stage talking all the time. We got to figure out how to get you a stone bus of yourself. No, no, no, no, no, no, no. Don't want that. You know, as a salesperson, you know, I have an ego. So when you said my boss is my biggest customer, I went,

"Screw that, I'm my boss's biggest customer." But how do you balance between bending over backwards for their needs, their communication style versus this is what I need and this is how you need to communicate with me? Yeah. I love the question and I love the assumption behind it because really that's where I come from as well. Just thinking the fact that when you think about your biggest customers,

or your biggest prospects who you want to become your biggest customers, the reason that they do is because they give you something in return for your service to them. That's usually a contract or something like that. And in most sales trainings, what do they say about having to make the ask, having to ask like, well, are you going to move forward? What do they say about the necessity of that if you've done the discovery really well and you've done the process really well? Right.

Or you don't, right? Like it's assumed that because we've gone through this process and I deeply understand your problems, I can prove that I understand the problems you're trying to solve. I can prove that we're able to solve them. I can prove that we've solved them for people who look like you. And I'm doing that actively and I'm being reliable at every step of the way. Then it's like a natural, almost foregone conclusion that there's something that I'm going to ask for and it's going to be a yes.

in that case. And so I think, again, if we're following the same paradigm, if you are dispositioned such that we've just been discussing towards your leader, often your asks are

They're not unreasonable in any way. And so if you're thinking about like, well, there's some things that I absolutely want to help you with. I want to serve you in this way. I would love to take this off your plate. In order to do it, here's some tools and some things that I might need in order to make that happen. Are we able to do that? Should we shave off what the ask is or should we ramp up what the ask is because you're going to over deliver on this side? It's the same sort of process that you have with your largest customers or your largest clients.

or your largest prospects to some degree, right? And so again, the shortest distance to getting what you want and need is just making sure that you're rabid about helping other people, in this case your boss, get what they want and need, not indiscriminately, but on the basis of the relationship that you're managing and building. Does that help? That does.

What happened? Oh. We're going to call it. Oh, okay. We're going to call it. Oh, that's a lie. All right. We're going to take a break. The Swiss train. Okay. Sorry about that. I'm sorry, everybody. DeJuan Brown. Ask me in the corner.

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