Podcast: Managing Up, Managing Across, and Retaining Your Best Employees

On the first of our two-part edition of Ask Insight, we take our listeners’ questions to the experts: Carter Cast and Craig Wortmann. Cast is a venture capitalist for Pritzker Group and Wortmann is the founder and director of the Kellogg Sales Institute. Both are clinical professors of innovation and entrepreneurship at Kellogg.

In this episode, we hear how leaders can create more fulfilling workspaces and influence colleagues up, down, and across the org chart.

Podcast Transcript

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Laura PAVIN: Attention The Insightful Leader listeners. Our podcast will be taking a little break for most of July. But we’ll be back in August with something really new and exciting. It’s ​​our first ever podcast miniseries…called: Insight Unpacked: Amazing Brands and How to Build Them. That series will feature many of our favorite Kellogg professors explaining how to build a brand from the ground up. And it’s honestly a lot of fun. You’ll be able to catch that in this same podcast feed when it drops in August. So stay tuned!

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PAVIN: Laura Pavin here…today’s episode of Ask Insight is the first of a two-parter. This one is focused on leadership and management. And the second is about entrepreneurship and entrepreneurial selling. That’s coming next week. So stay tuned!

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Jessica LOVE: Hey there. It’s Jess Love. I’m the editor-in-chief of Kellogg Insight…and I’m your host for today’s episode of Ask Insight — a special feature on The Insightful Leader where YOU ask us YOUR questions about management and business — and we take them to our faculty here at the Kellogg School of Management for answers.

Today, we’re digging into a mailbag of questions you asked us about leadership on social media…so we tracked down some resident experts.

Professor Carter Cast is a clinical professor here and teaches about entrepreneurship and leadership. He’s also a venture capitalist for Pritzker Group..where he invests in early stage tech companies and works with entrepreneurs to help them scale their startups. He is a former CEO of Walmart.com.

Carter, welcome.

Carter CAST: Thank you.

LOVE: And Craig Wortmann is also a clinical professor at Kellogg. He’s the founder and director of the Kellogg Sales Institute…where he helps leaders develop the skills they need to grow themselves and their organizations. He also has more than 25 years of experience in sales and entrepreneurship.

Craig, welcome to you.

Craig WORTMANN: Thanks, Jess. So fun to be here with you and Carter.

LOVE: All right, let’s dive in. We had a specific question about an interesting approach to retention. There’s this idea out there that you can make work itself more interesting or engaging by just stripping out as much of the administrative tasks as possible and letting your star employee focus on what they do best. So if they’re a top designer, if they’re an amazing digital marketer, they just do their digital marketing work. And…and that’s it. Do you see value in rethinking and rebuilding jobs in this way?

WORTMANN: …yes. The reason I’m hesitating is, I also am very much from the school of thought that as long as my manager, leadership, coaches, are clear with me about the expectations for this role—and the expectations include some tough gritty work…that is not the most interesting work—as long as those expectations are there…I should be willing to do that work. I’m skeptical of where some parts of the conversation seem to be going right now. Because I think if we extend it all the way, it can turn into, you know, “you should only be doing fascinating work.” That is not true for any of us. We all have to do some tough work and that’s okay. But again, that lives in a conversation with really clear expectations from managers and leaders to say, you know, “we’re going to architect and design this role so 85% of it is you, just your raw talent lending itself every day, 85% of the time. But let me be clear, 15% of the time it’s going to be the gritty sort of yucky work that has to get done to allow you to leverage your talent.

LOVE: Is there ever actually a value to some of that administrative work, even if it really has nothing to do with designing or digital marketing?

CAST: Oh, I think so. There’s value in the doing. I actually think it’s a good idea, when you begin, to have plenty of administrative tasks that you do so you understand how things get done around here. And then, when you’re going to be training and developing somebody, you can explain to them how things get done. And you’ll have an understanding, if they’re taking time to get something done, what they have to accomplish because you’ve done it yourself.

The second thing I would say is that sometimes there’s gold in the dark. Sometimes when you’re doing those little minutia things, and you think, “oh, why am I doing this?” actually, you’ll uncover things that you wouldn’t uncover if you were skating up at 10,000 feet. When you’re down there, clipping the trees and doing some of these things, sometimes you can find God is in the detail. Sometimes you can find something in the very specific work that you’re doing that you would miss if you were flying too high.

WORTMANN: And you build a different form and more solid credibility as you do those tasks. Last weekend, we had a Kellogg reunion and a former student from a few years ago reached out and wanted to meet. Super talented young person, three years out of Kellogg, and had walked into this very big job out of Kellogg as a newly-minted MBA. And it wasn’t the right role for him. And he happened to interview with the CEO of a company that is a very fast-growing tech company. And in the process of this interview, this CEO convinced him to take a role in the sales organization at the lowest level—what we in sales call SDR: sales development rep. So it’s basically a cold calling lead generation position. It’s the hardest role that you’re gonna do. And here’s this hotshot MBA. Takes this role and he was nothing but smiles last weekend telling me this story about how he, the last couple years, has rocketed through this organization. Is now a leader in the sales organization.

You know, he had to…as a design of that job…do the admin, the hardest work in the organization. And now he can look people in the eye and say with maximum credibility, you know, “I’ve walked in your shoes, I’ve done that, and I can help you do that better.” And it’s just so…he’s so glad as he looks back…only a couple years…he’s so glad he did that.

LOVE: Well, this is a popular question. I’m guessing you guys have got this in some form before, but we had a reader asking about the always challenging process of managing up and managing across. I’m guessing a lot of our listeners have heard of these terms: managing up is about influencing the people that are senior to you in an organization. Influencing across would be folks at your peer level across the organization. What do you guys think? What advice do you have when you’ve been asked this before?

CAST: Can I start with managing up, since I’ve done it so terribly, so frequently, in my career?

WORTMANN: [Laughs] As have I!

CAST: I was notoriously bad at managing up. I really thought that if my boss would just leave me alone and give me room to run, then everything would work out just optimally. I ended up getting demoted for that wonderful attitude that I had with my boss. And I learned something in this kind of painful demotion. I was put on ice for about a year in my company, and I had to work my way out of the penalty box. I realized that it would behoove me to see my boss as a customer…and my job—if I’m an underling—my job is to make my boss as effective as he possibly can be. So instead of…my attitude at the time, which was, you know, “just leave me alone. I know what I’m doing. So you can leave me alone and let me produce…” instead, I should have said, “what are your goals and objectives, and how can I fit into them? What can I do to take work off your plate? Are there any things that, uh, you don’t wanna do that I’m qualified to do, that I can help you with? How do you like to communicate? Do you like to communicate, you know, email, phone, early morning, late night? What modality do you prefer? So I can fit into the way you like to get work done.”

If you look at a hierarchy of the organization, sort of by design, the person above you has a bigger job that probably has more direct impact on the results. So you would do well to help them be effective in their job. I did not get this. Craig. I acted in a way that was really inappropriate for a number of years, and finally realized my job is to try to make my boss effective. Now, I’m not talking about brown nosing and being ingratiating…I’m talking about trying to make them as effective as possible. And once I started realizing that, low and behold, my career went better.

WORTMANN: I…again, I’d add one thought. So, all of what you just said makes total sense. And then, when I think of managing up or across, I think the other key point that I talk with people about is being open to feedback. So now you know those things. You know how your boss communicates, you know the modalities…his or her or their goals, aspirations…what would make them look good with their bosses? You know all that stuff now, in the process of doing that work and delivering for them…and you being open to feedback and being very proactive about asking for feedback—not obnoxiously—but “how am I doing? Give me some coaching, give me something to do differently,” such that you get better and better, faster and faster, in the process of delivering those goals.

CAST: That’s a really good, important addition. To try to answer—at least, approach—the second part in managing across. I think the first thing that I would try to do…meet with the people that are your constituents or that are your peers, and try to find out what are their goals and objectives. What are they trying to accomplish in their jobs? And see where you can help them…see where your goals and objectives are in alignment so you can be of assistance to them. And then, most likely, when you offer your assistance, they will reciprocate and say, how can I help you? And so you establish, “I know what your goals and objectives are, you know what mine are, and we’re gonna try to help each other along the way.”

Second thing is—it’s going back to this empathy—I would ask them that, “where are you having…are you having a difficult time with our function or our group in any way that I can help alleviate? Are you finding it difficult to work with us?” And if they see you trying to make things more efficient and better, they are going to be more open-minded and they’re going to be easier to work with, to you.

LOVE: You guys are giving really great examples of how to do this managing up, managing across. When you’re kind of on the same page as the person that you’re working with—and I think this is especially true when you’re managing across—what do you do if you’re really butting heads with somebody? You just have a really different vision for how the organization should be responding to a challenge.

WORTMANN: I think the move here is to acknowledge that there is a difference and to have a difficult conversation. And in so much of the work that I do at Kellogg, it’s centered around how do we actually establish and understand our differences? And then how do we have a conversation around them? And I just think the step one is acknowledging and going to your peer and saying, “you know, it seems like”—and again, I don’t know the exact words, but—”you know, Carter, it seems like you and I are running down two different paths in two different directions. And I feel the tension and I feel the heat, and I wanna acknowledge my role in this. Can we have a conversation about this?” And I just think if you lead in that way…it doesn’t make it…I don’t know that it makes it easier? It just makes it more real. And it makes it…it puts you and hopefully your counterpart in the mindset of listening to each other, asking the questions and then eventually solving the problem. I don’t know how else to get to that.

CAST: Yeah, I think it’s really good advice. And then, I’m sure as you open up and you find we have common objectives here and here…yes, it seems like we’re diverging over here. And then maybe that gives you the chance then to unpack that area and try to understand, are there any assumptions each one of you are working under that may be erroneous…that is leading to your departure. Or, fundamentally, are the goals and objectives just differing because purchasing wants this and merchandising wants that?

WORTMANN: I think it’s Adam Grant who said, you know, “always make sure to make the most respectful interpretation of the other person’s perspective as you possibly can.” What a skill that is, if you stop and think about it. Cause it’s hard. Cause there’s heat in the moment. I’m emotional, right? I’m, I’m feeling like, “ah, Carter, I’m disagreeing with you.” But then I say, “hey, let me reinterpret what I’m hearing you say.” And I make the most respectful interpretation. Wow. Talk about influence.

LOVE: In your experience, how often, when these kinds of tensions go badly, is it because of some sort of fundamental misunderstanding about everyone’s perspectives and everyone’s goals? And how often is it really just like…that person’s out to get me? [laughs]

CAST: I think plenty of times it is not doing what Craig said right off the bat and not being direct with each other. So there can be misinterpretation and there can be assumptions you each make on this other person’s position. And a lot of times, once you sit down and talk about it, you find out that actually there is more commonalities and shared goals than you think going in…but there’s probably been—I don’t know if it’s animosity—but there’s been enough tension that the issue has become bigger than it really is. And once you sit down and discuss, you can find where the issue is. And it usually—in my experience—the issue isn’t as big as what you’ve made it to be before.

WORTMANN: I’m just smiling and nodding. Embrace healthy conflict, not unhealthy peace, always and forever. That’s the key.

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Hey there, it’s Laura Pavin again. We hope you enjoyed part one of our two-part Q&A with Carter Cast and Craig Wortmann. If you want to hear what they have to say about entrepreneurship and entrepreneurial selling, that episode will drop next week. We hope you take a listen!

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