How to Avoid Career Derailment with Carter Cast

Reading Time: 28 Minutes

Carter Cast, author of The Right-and Wrong-Stuff: How Brilliant Careers are Made and Unmade. In this interview, Carter shares the insights and secrets he uncovered.

About Carter Cast

Carter started his career at PepsiCo, where he became Director of Marketing for their Frito Lay subsidiary. He went on to lead as CEO from 2000-2007 and Hayneedle, Inc, from 2007-2011. Today Carter teaches innovation and entrepreneurship at Northwestern University and invests in early stage tech companies through Pritzker Group Venture Capital.

Read the Transcript

Allison Dunn:  Hi. Allison Dunn, owner of Deliberate Directions, your executive business coach.

I am so excited today. We have a fantastic guest here with us. His name is Carter Cast and he is the author of “The Right and The Wrong Stuff,” “How Brilliant Careers Are Made and Unmade,” and was listed as a must-read list for 2018. 

I’m just going to quickly do a quick introduction of your background. Carter started his career at PepsiCo, where he became director of marketing for their Frito-Lay subsidiary. He then went on to lead from 2000 to 2007. During that time, Walmart became the third highest volume E-commerce company, just short of Amazon and eBay which is super impressive. 

He then served as CEO of hayneedle which is an online retailer of home furnishings and decor and today Carter is a clinical professor of innovation and entrepreneurship at the Kellogg School of Management at Northwestern University.  He also invests in early stage tech companies through Pritzker Venture Capital.  Carter, thank you so much for being here with us today.

Carter Cast:  You’re welcome. Thank you,

Allison:  I am a huge fan of this particular book and the reason is because it is so pertinently appropriate for what happens to almost everyone as they grow in their leadership career. From the idea of derailments, what inspired you to write this book?

Carter: From an academic standpoint, I thought the topic was interesting because someone who teaches innovation and entrepreneurship, you look for good books that you can offer to the students and there’s so many books on leadership and how to books on leadership success but there’s very few books that actually take a look at managerial and leadership failure and dissect what happens to good people when they run into career trouble. What about their situation or themselves leads them into choppy waters and I wrote a white paper on the topic of career derailment and as part of my work in academics, and found that a lot of people were using a lot of the material because there’s just not that much out there. I think that’s been written on this. 

I still had a lot to say after I was done. I felt like there was a lot left to say so I decided to write a book on it. 

It’s a topic that I don’t think gets enough attention because it’s an uncomfortable topic and secondly, you and I encounter it. 

I’m sure as a career coach, you do too all the time. You see great people who run into trouble. 

I started wondering, are there certain themes as to why good people run into trouble? And I found that there certainly are themes.

Allison: Can you for our listeners, define what you mean by someone who’s a derailer?

Carter: Yes, the term derailment. The way I defined it is somebody, I didn’t look at people that weren’t talented. I looked at talented people who are assumed to have 1 or two levels of promotion in them at least and then something happened. Either they got fired, demoted, or they were considered non promotable, they flattened out. 

I looked at people with talent, people with game that were expected to go say from a manager to a vice president or from a director to a senior vice president or for an assistant manager to a manager and they didn’t get there.

What happens to people to make them either get demoted or fired or just told they’re non promotable?

Allison: Right. I’d almost joke a little bit when someone gets derailed which I feel like, it should happen to someone could self-identify with that at any point in their career eventually but then they just go start businesses. That was the way that I joke right? 

Could we take a moment to go through the five derailer types and what is the number 1 that affects most people? What’s the most common kind of derailment?

Carter: I did all this research and I interviewed 100 people who got demoted or fired. I looked at all the academic research. 

By the way, there’s a lot in looking at 360s. If you look at patterns and 360s and people that are considered at the top 10% of their company and managerial effectiveness and then look at people who are in the bottom quartile and look at the competency differences. Look at the competency profiles. 

What strong traits or skills do people have that do well? And then what lack of skills or traits do people have, that are not doing? 

Well, there’s a ton of data I found but I found these five things over and over that kept appearing.

To try to make it more palatable and little less scary of a topic, I created these fun personas or characterizations for our types and the number 1 reason that people run into career trouble the most is

lacking interpersonal skills and being considered to be difficult to work with and I call that person, that caricature Captain Fantastic.

Allison: Captain fantastic, which I think is a perfect name for it.

Carter: Yes and that’s somebody that has poor listening skills, is probably overly ambitious, and bruises people with his sharp elbows on his quest for the corner office and what happens is they do well early in their career because they’re ambitious but eventually they get into an assignment that’s nuanced and requires a lot of cross functional collaboration and people don’t want to work with them. 

Those are us the gender, the male gender as I was talking about it. This reason for derailment skews male, more men derail for being ego driven, over bombastic, and defensive than women.

It’s not the biggest reason that women derail.

Allison: That makes sense for a lot of different reasons. I would agree with that. 

Someone to self-identify if they are Captain fantastic, what would be the top two or three things that you’d be like, “Oh, maybe that’s me. Gosh!”

Carter: I’m being told that you need to work on your listening skills.

Allison: I’m listening. OK.

Carter: Not doing a good job of being empathetic and listening to the other person before you speak. 

Not seeking different perspectives on what you should do. Just barreling ahead without listening, especially to the front line, the employees that are closest to the customers. 

That’s what is somebody that has poor listening skills and along with that being defensive. Not being open to criticism and having a knee jerk reaction. 

If you’re like that. If you don’t listen and you’re defensive, you’re not going to learn from your mistakes very effectively and people aren’t going to give you feedback because they know it’s like shouting in a wind tunnel. 

That is that by far the biggest ones, is defensiveness and poor listening skills. 

I think the ego needs to get back in check. This is a problem a lot of times of somebody experiencing some career success and then starting to read their press clippings too much.

Allison: OK. You had that big wakeup call when your boss basically told you that you were un-promotable and it was it because you were Captain fantastic.

Carter: Yes, it was unfortunately. It was a form of Captain fantastic. I didn’t like the heavy hand of authority and I didn’t like to be told what to do when I thought I knew what I was doing and in this case, this person came in above me in the organization and I’d been in the position of 3, 4 years and they were new and I thought, well, he should just leave me alone to let me do my job because I know what I’m doing. 

I think I was difficult to manage and he actually kicked me off his team and I ended up in this desert alone, having to learn a little bit of humility. 

The good news is that guy had the guts to do this and it was a wakeup call that I needed and in hindsight, it was 1 of the best meetings that I’ve ever had because it made me start working on this issue I have which is authority issue with authority figures and learning to be more coachable.

Allison: For sure. I think what a gift he gave you and I think I recall you sharing in the book that decades later, you actually reached out to him. Correct?

Carter: Yes.

Allison: To thank him. I’m sure. 

We, as supervisors and leaders and managers, don’t often give that type of really harsh, honest feedback. How do you how do you get that from your manager when you need to have it and want it?

Carter: That’s a good question. I think a lot of times the problem comes when the only feedback you give is negative feedback.

Allison: True.

Carter: First of all, I would say, if you’re giving a constant flow of feedback to somebody and a lot of it is,  

“He did a great job in that presentation.”

“I love the way you use that case study to explain our value proposition. Great job! Really good job, Emily.”

If you give balanced feedback, then the person trust that you have their best interest in mind.

If all you do is you give them feedback about something that’s negative, then they’re probably going to not take it as well. 

One thing is make sure that if this is a subordinate that’s underperforming, you want to be giving them constant feedback along the way and also encouraging feedback. That’s, I think, the most important thing.  Separately, I have a friend who created what he calls, “The world’s simplest feedback model.”

Allison: Oh, what is it? Give it to us.

Carter: Yes. Let’s say that report to me and you just gave a presentation and I am your boss and I was in the audience. When we walk out, I say,

“Let’s get feedback.”

The feedback model is, I say,

“What’s 1 thing that you think went well in there?”

Then I shut up and I listen and I don’t contradict you even if I don’t agree with you. I listen and when you’re done talking, I said,

“Here’s 1 thing that I think went well on there.”

And then the second thing I say is,

“What’s 1 thing that you would do differently?”

And then I’m quiet. I listen and I say,

“Great. Here’s one thing I think you could have done differently.”

What I’ve done is I lead with a positive and I listen and then I do something that has to do with a developmental area.

One is, it’s fresh, right? The event just occurred. You can see the link between the event and my comments.

The problem comes a lot of times with feedback that we give, we give it like months after the fact in some performance review.

Allison: Right, and it’s confusing then, right?

Carter: It’s confusing. Sometimes I can’t even remember what the circumstances were that you’re explaining or you talking themes and platitudes and you don’t use specific instances.

If I say,

“Allison, I think you did a great job in bringing people along with you. As evidenced, by the way you asked a question to the audience within about 30 seconds that was terrific.”

And then I said,

“What’s 1 thing you do differently?”

And then after you talk, I say,

“One thing I would do differently is, I would probably in the beginning of the presentation set the agenda, tell him what we’re going to do, tell him how much time it’s going to take because I think we got a little bit rushed at the end. Did well, do differently.”

And then you’re done.

Pick 1 thing because if I say to you,

“Time for feedback.”

And, “Oh god, I know Carter. He’s going to go through a list of 10 things.”

You’re not going to remember it and it’s also a downer but if you pick 1 thing to emphasize on the complimentary side and one thing to emphasize on the developmental side, then it’s much more. You can actually look forward to feedback.

I’ve actually instituted this at Northwestern. We, a group of people, whenever we’re in the room with each other in something that’s meaningful, an event or a presentation or something, we give feedback and it takes five minutes to do.

“Did well.”

“Do differently.”

My biggest piece of advice is a constant stream of feedback, not a onetime event.

Allison: Yes.

Consistency and recency of it. Being in that time. What I particularly like about that feedback loop is that you’re asking. Let’s say, I’m the presenter. You said,

“Alison, what did you think?”

You’re asking me to self-reflect and then you get to add to that and then I self-reflect on what didn’t go well.

I like that the individual gets to go first as opposed to going like,

“Oh yes, I know. I blew that.”

You only mean you don’t affirm on the backside of it. That’s cool.

Carter: That’s right.

Allison: Yes. Fantastic.

We’ve talked about Captain Fantastic and I just want to make sure that we covered the other four you have and then I’m looking for like a 1-minute tip on if you’re this than that.

I think you’ve done a great job of talking through Captain Fantastic as a derailer and that being your own derailment but what would be number 2? The solo flyer.

Carter: The solo flyer is somebody that gets usually have trouble being a effective manager and when I interviewed people and read a lot of research, what typically happened was, you have an individual performer that gets promoted because they’re good into a management job and becoming a manager as a transformation of identity that was literally like Linda hill of Harvard described it.

She wrote a book called “Becoming A Manager,” that was really good where she followed 19 different people after they promoted into management and just observed what they did well and didn’t do well and she came to this conclusion that becoming a manager is like a transformation of identity.

You have to learn from going from me to we, and from being the player to the coach and it’s a hard transition, especially if you’re really effective. You want to dive in and do it yourself.

The problem that the solo flyer has, often is, they micromanage and over-manage, and they don’t teach their subordinates to fish, they try to fish for them.

People get demotivated because they say,

“Oh, Alison’s going to dive in here and tell me how to do this.” And so you lose the feeling of ownership for your projects.

Allison: Shifting the identity from focusing on myself to how do I develop my people to be better?

  1. Awesome. All right.

Carter: One of the things that you really want to do is a lot of Socratic dialogue.

Instead of being directed, be Socratic in your conversations.

“Allison, what are the 2 or 3 options of what you think you could do?”

And then you listen and you say,

“Of those 3 options, are you leaning towards now and why?”

Socratic-ly just keep asking questions and I’d say 9 times out of 10, the person knows what to do. They need a little bit boost.

Allison: Yes.

Sounds like you could be a professional coach, for sure.

Carter: Well, I can’t. I love what you do. I think it’s one of the most important jobs there is, is having a good coach and I didn’t realize how important it is until I finally got to coach myself in later years and thought,

“Oh my God! Why didn’t I do this earlier?”

Allison: Awesome. Thank you for that endorsement.

I think what we do is pretty important too.

All right. Let’s talk about derailer number 3, your version 1.

Carter: Yes, version. 1.0 is somebody who gets comfortable, they get in a groove and the groove turns into a rut and pretty soon they become a fossil.

Allison: I say goes from, it turns into a groove, then it becomes a rut, and then it becomes a grave, which is very unfortunate.

Carter: Oh, yes. That’s exactly. Yes.

This person has trouble with adapting to change and the biggest change they have to adapt to is usually either a new job, a new boss, it could be a promotion, even a new job, a new boss, or a technological change.

Allison: Right.

Carter: Something starts disrupting the way things have been done. Maybe it’s the internet comes along in 2000.

Or maybe it’s everything turns into being staffs, software as a service.

Or maybe you’re starting to use machine learning and you have to understand robotics.

Or you’re going to do something with crypto currency. You’ve got to stay current on what changes are occurring in your industry, technologically.

In this case, this person needs to utilize their network and make sure their network has people that are strong in emerging areas which are becoming more important business.

It’s really one of staying abreast of change by tapping your network and asking for advice.

I ask people,

“Are you on Twitter?”

Allison: Yes.

Carter: Do you have people on Twitter that assist? They’re on there? My Twitter account is of young venture capitalists who are really sharp, I study what they post.

Allison: I mean, it tells you a lot just by being in the know on it from a social standpoint, right?

Carter: Right. That is one of the biggest reasons.

One of the other reasons that version 1.0 gets in trouble is, they don’t do a good job when they have a transition and they have a new boss and that’s what happened to me. I got a new boss and my old boss I did well with now just knock out. 

I say to people,

“Treat your boss like a customer. Your job is to make us successful. What can you take off their plate? What do they need to have you do for them that they’re not really doing themselves? What is their agenda and how can you help them further their agenda?”

I did not have that attitude. When I was younger, I just wanted my boss to leave me alone and let me perform and if I would have taken the time with his fellow, Mike, I would have taken the time to say,

“How can I help you be successful? And you’re new at the company. Can I send you some of our strategy decks? Do you want to go on a market tour with me? What time are you the most productive? Well, what can I take off your plate?”

I didn’t treat him like a customer and if I would have treated my boss better, he would have probably had more confidence in me.


Allison: For sure. That is probably one of the most common coaching conversations I have when working with my owners teams is,

“Do you understand what Kevin’s agenda is? And what’s important? And how your role serves that?”

I mean, it has to be mutual.

Carter: You have to be prepared to change your agenda to make sure that they’re successful with their agenda.

Allison: Right.

Carter: If you do that, they’re going to have more confidence in you and realize that you have their back and with that will come more trust and with more trust will come more freedom.

Allison: Yes, that’s so good.

Carter: That’s version 1.0. Scares me as a venture capitalist.

Allison: I bet.

Carter: I’m 56 and I have to stay current to see what all the 30 year olds are using? What software they use? What tools are they using?

Allison: What was so funny, I did get a question. I put it out over the last couple of days that I was speaking to you today and the influx of questions from my younger followers was phenomenal.

They wanted to know,

“What social media platform is the older generation using?”

And I thought that was an interesting question.

Carter: Gosh!

Allison: What’s the answer, Carter? I’m like all of them because you have to.  

Carter: I think that were the folks, it’s the usual suspects but they are using slack. I literally, I have a Slack channel for my class and I was talking to one of my fellow professors and I said,

“You have a Slack channel to stay abreast of what the back and forth is by your students?”

And what do you think he said to me?

Allison: No.

Carter: No, he didn’t. He said,

“What Slack?”

Are you serious? That’s what I’m talking about.

Allison: Yes. That’s funny.

Carter: “Have you ever been on Instagram?”


They don’t understand these platforms and my job as a VC is to watch and understand what people are using that are younger because the chances are really good that we’re going to make an investment in one of these spaces.

Version 1.0 is one that worries me because I have to have learning agility.

Allison: For sure. Especially yes.

Carter: You have to have good discovery skills. What are discovery skills? Things like experimenting. Always running a/b tests and trying things.

Observational skills. Am I watching younger people at the school, how do they use technology?

Questioning skills. Asking,

“How might we?”

“Why do you do it that way?”

Constant stream of questions and those skills, networking, experimenting, questioning, observing, these are the discovery skills that will keep you from becoming a version 1.0

Allison: Sounds interestingly enough, through each of the derailments, it’s a lot about listening and asking good questions to have a better understanding.

Carter: Listening is I think, for whatever reason, it’s the unheralded critical. It’s a critical skill.

Allison: Yes, I guess.

All right. That’s version 1.0.

Tell me about your one-trick pony.

Carter: This was the number one derailleur for women.

Allison: OK.

Carter: Number one derailer for women was a one-trick pony.

One-trick pony is somebody that is considered nonstrategic and they hit a ceiling on their promote stability. It goes something like this.

Let’s say you have Gail and she’s a controller and she does a great job as a controller, she closes the books, she’s good at passing the audit with flying colors and she wants to become the CFO.

She goes to her boss and says,

“Hey, Ron. I want to become a CFO. I want to talk about my path.”

And he said,

“Oh, you’re a great controller. You’re doing exactly what you’re meant to do.”

And she says,

“Well, that’s not what I asked. I asked the path to become a CFO.”

And he said,

“Well, you don’t. You’ve never done forecasting, you’ve never done a long term capital asset management projects. You’ve never worked with the strategic best business units on their annual operating plan. You’ve never dealt with Investor Relations. You don’t have a lot of these skills that you need to be a CFO, Gail.”

And Gail says,

“Well, that’s the first time I knew I needed these skills.”

Whose fault is that? What I just explained?

Allison: Both.

Carter: Absolutely. Both.

Allison: Yes.

Carter:  Ron’s fault for not understanding what her career aspirations were and helping her get experience in areas that weren’t core to what she does and it’s her fault for not seeking it out.

Allison:  Right.

Carter: Because no one’s going to take care of Gail except Gail.

Allison: 100%. Yes.

Carter: Count on that boss being the type of boss that wants to see you develop, if you’ve got a boss that is like that. Good. Fantastic, but you can’t count on him.

Allison: I think what it is an interesting point and I can see why this is more of a female derailment, is I think women are less likely typically, to say,

“This is what I want and this is how to get to see if I like that’s my ideal role.”

Where someone might sit and go. If I do a really good job, maybe they’ll see it in me and give it to me.

Carter: I agree 100%. You’ve got to ask for the sale.

Allison: Yes. Every time.

Carter:  I think, a lot attached to this.

Are men more strategic inherently than women? Of course not. It’s ridiculous, right? It’s ridiculous.

This is a problem of access. Access to opportunities, access and visibility. The good old boy networks alive and thriving and it’s easier for men to get cross trained in different areas than women because the business environment is encouraging of men.

Now, I think it’s getting better.

Allison:  Already great. Yes.

Carter: It’s getting better but nonetheless, you can’t count on somebody else taking care of you. You’ve got to take care of your own career, you have to ask for a job rotation, you have to ask for these opportunities because they just don’t land on your lap.

Allison: In this sense, it’s speaking up and saying what you want over listening?

Carter: Yes.

Allison: And that will be.

Carter: It has to be on a task force in a different area. Raise your hand for new assignments, network effectively with other senior managers because someone might pull you into a new area but there was a real theme here, Allison of someone moving up vertically and then topping out because they didn’t have the breadth of experience to get to that next level.

You definitely have to become an expert in a particular area, right?

You’ve got it. That’s your job security but let’s say you get there for 8 years, you’re really good in an area, you have to start looking for opportunities broad.

Allison: Expand that.

Carter: Expand it. Have you heard the leadership T that holds?

The leadership T is at the vertical part is you moving up and then the horizontal part of the T is you managing and leading and doing broader activities. You have to do both and starts with moving up and having that the bottom of the T be strong and high up, but then the top of the T is you expanding your breadth.

Allison: OK. All right.

We’re down to our last derailer. The whirly dervish which I think is such a great term. Tell us about the whirling dervish.

Carter: This is somebody and by the way, this was the second most common reason for derailment.

Allison: OK. This is somebody who gets overextended and they don’t manage their time. They don’t prioritize well and balls drop and because balls drop, they get a reputation for being somebody who doesn’t deliver on what they promised.

If you unpack this when there’s several things this person does ineffectively.

Number one, they don’t have a system by which they organize. Organizing their work. What system do you use? What method do you use to manage your inbox and manage your meetings? And is it outlook? Do you use Evernote? Do you use HubSpot? What Salesforce? What tools do you use to manage your business and your time?

And if you talk to a whirling dervish, the chances are pretty good that they aren’t very systematic in the way that they manage all that goes on. They don’t have a system.

I refer people to “Getting Things Done” by David Allen, which is a book about time management and process management.

The second thing is they often have trouble prioritizing and doing the things that are most important. First things

The Stephen Covey quadcore?

Allison:  Oh, yes.

Carter:  It’s that. It’s making sure that you don’t just attend to the important urgent things, you also intend to the non-urgent important things and you lay out your week, and your month, and your day, so that you attend not only to the things that are pressing but you keep chipping away at working on the things that are important but they’re not as time bound and you prioritize and reprioritize multiple times a week.

People that were really dervishes had real trouble with identifying what was most important to do. They just treat everything equally as important and they just like checking things off their list, maybe half the checks, maybe half the things on there, you shouldn’t even be doing because they don’t move the needle enough.

Allison: Right. I look at a whirly dervish as someone who just really wants to accomplish a lot but it may not be the right things.

Carter: Yes.

Allison: Best of intentions, like going about it fast but maybe not correctly.

Carter: Exactly.

One of the biggest traits of a whirling dervish is having the disease, “The please.”

Allison: Right. Yes.

Carter: Somebody just can’t say no and they end up getting pulled in too many directions because they have trouble saying no to somebody.

I offer some little practical tips to say no.

One is, and I’m sure you do this a lot as a coach.

One is, buy yourself some time. Instead of automatically saying, “Yes,” if you have a natural urge to please, you say,

“Allison, I’d love to do this podcast but can I get back to you by say, 3pm today? I have to check my calendar and look at my agenda to make sure I can do this.”

Buy yourself some time instead of automatically saying, “Yes.”

And then when you buy yourself some time, it’s easier to say, “No,” When it’s not as sensitive. That’s one.

Another thing is, sometimes you say, “No” but you offer something as a conciliation. You say,

“Allison, I really don’t have time to do that but I know of a couple good people on this topic that you should probably talk to.”

Allison: OK.

Those are both really good ones and yes, I use those all the time and I just want to say thank you for making time to be on this podcast, just to affirm. That’s great.

OK, that was our 5 derailers. Thinking about it from like fixing your employees derailer, you’re the leader and you have a team. What are some of the symptoms that might alert a company that they need to play a more active role in guiding them away from derailment?

Carter: Yes, the problem we get is, by the time you start working on derailment, the hen has come home to roost. It’s already in bad shape and there’s probably already been some either reputational damage or you’re already been typecast as being a problem.

The solution to all of this is self-awareness and how do you improve and increase your self-awareness? By constantly asking for feedback.

If you ask after that presentation,

“What went well? What do you think I could have done differently?”

And if someone’s reticent to say,

“You leave, Allison. I don’t think I started off very strong. That’s one of the things I noticed, what did you notice?”

You show them with a display of honesty that you really do want the feedback.

The number one solution to all this is, if you ask for a lot of feedback, you can make little course corrections in your behavior and not get whacked upside the head with a big old derailment area.

Allison: I think one of the things that our current younger in coming into business generation is they do ask for feedback consistently.

I feel like they are getting hopefully the feedback that they need to be able to prevent that derailment.

In your book, you share a statistic by the management consulting company, Korn ferry, and you said that when managers rate themselves on 67 different managerial skills, they scored worst on developing others because developing others requires the others to be involved.

I’m sure, which is probably why it’s hardest to score.

If a company believes that their staff is going to be leaving in 2 to 3 years that like longevity of an employee is getting shorter and shorter. How do you help them overcome the mindset of not investing in them?

Carter: Don’t bother. This person is going to leave anyway.

Allison: Or they stay forever and become your version 1.0.

Carter: Yes.

Do you remember this is a while ago, Gallup wrote this book, “First Break All The Rules?”

Allison: Yes.

Carter: 2001 and in it, were the Q12.

These are the 12 questions that you ask employees that are the best indication of their level of engagement. How highly engaged they are?

The higher their engagement, the better their performance.

Allison: Absolutely.

Carter: Gallup found these 12 questions and anybody that’s listening, go on Google or your favorite search engine and type in “Gallup Q12” and they will list the 12 questions that they found indicate the degree of employee engagement.

If you look at those questions, a lot of them underneath it is this fundamental question, which is, do you care about me boss?

And if you do a couple of things, their work product will be higher and better.

One, let them know that you care about them as a human being. How is your weekend? How is your dog? I know that your dog was sick? Did your kid win that soccer game? I know you’re going off to the soccer. Show interest in their life because that will make you guys have a bond and it will strengthen performance even by showing interest.

Secondly, you understand their career aspirations. Do you understand where they’re trying to take their career? And then you say,

“How can I help you get there? If this is what you want, maybe I can help you.”

If they believe that you care about them as a human being and you are trying to help them with their career, they will overlook your own foibles and they’ll go through a brick wall for you.

Allison: I completely agree. We have those 12 questions on our website under our employee engagement and we do that employment engagement survey is what I call it with dozens of businesses here locally to have an estimation of where their people fall so that they know what they need to work on it.

Carter: Fantastic.

Allison: Yes.

Carter: It is no. I mean, it’s no secret.

I launched the Q12 with my direct reports and so quarterly, we would see how people were trending on the level of engagement of the employees in the merchandise department or the product supply department or whatever and sure enough, the people that ended up getting the promotions are always the people that have the highest level of employee engagement.

Allison: Absolutely.

Kudos to you for doing that quarterly. That’s great feedback.

Carter: If you would pack those 12 questions and the center of them is do you care about me? Do I have the resources to do my job right? Do I understand how my work fits in with the goals and direction of the corporation?

The second thing I would say is,

“Make sure with the people that report to you that you’re clear on what they do matters and how what they do links to the overall strategy and mission of the company? Because if you see that thread between your work and the company’s mission, you’re more engaged in your work because you realize it matters.”

Allison: Absolutely. I have a fantastic training that I do on this engagement topic and I guess, I’m not here to promote mine specifically.

What training do you recommend around developing employees so there’s no derailment? To increase engagement and all the benefits of that? Do you have something that you go to that you recommend? 

Carter: We’ve had. There’s so many different tools that I’ve seen used and different modules that Walmart and Pepsi and all these places I’ve worked with used.

This is going to sound like, “What?” But one of the ones that I find is really useful, is some form of crucial conversation.

Allison: Awesome.


Carter: Because when you get right down to it, one of the themes of our talk has been the importance of feedback and the importance of listening and many people are afraid to give feedback because they’re worried on how it’s going to be received or they’re afraid to stand up for themselves in their career because they’re afraid of a confrontation and I think one of the best modules that I’ve ever seen. We did this at Walmart was getting trained on Crucial Conversations.

How do you deal with hard topics? How do you show empathy? How do you disagree with tact? How do you make sure a message is heard, received, delivered?

One of my favorite ones is how do you learn to have hard, important conversations and do them with tact and with power?

Allison: Absolutely. Crucial Conversations is obviously a key topic when coaching and sometimes it’s almost you need to give permission to have a different shift around what it is that they’re doing and I’ve been able to have like a mental shift with people by calling it instead giving graceful honesty.

Carter:  Oh, good.

Allison: Yes. As opposed to a crucial conversation or brutal honesty or like all the other.

Carter: [Inaudible 00:42:40].

Allison: Wait.

Carter: It’s great but boy, you’re right, you immediately you’re [Inaudible 00:42:48] scared.

Allison: Yes, I mean, even suggesting, well, you need to tell them that and they go,

“Oh, no, I can’t.”

And I’m like,

“Well, let’s find a way to say it gracefully so it can be heard and received.”

Carter: Yes, that’s right.

I think that topic is just right up there at the top for me because if you get people who are actually get more and more comfortable with being honest, I mean, both ways, being honest about great stuff.

Just being direct and these relationships are stronger then the performance goes up because the communication’s better.

Allison: Absolutely.

Carter: These companies don’t perform well as generally. I mean, sure it can be strategies. The wrong strategy, of course, but let’s say that the strategy is sound. It’s usually the interaction between departments isn’t strong enough.

That is about communicating between, especially these natural areas of tension you have between finance and marketing or but between operations and customer service are these areas where there’s natural friction, you have to learn, you have to have a vocabulary, and a method by which to communicate sometimes.

Allison: For sure.

I always beat the drum that every employee wants to show up, do a great job, feel like they’re being productive and contributing to the bigger picture and without feedback on how to do it better, they’ll continue to do what they think is succeeding. Right?

Carter: And what you said is really important because almost everybody wants to do a good job.

Allison: Everyone wants to do a good job.

Carter: They’re not coming and they’re thinking, I wonder what I can get away with today.

They’re coming in, they’re saying,

“I want to do good work.”

And if you let them know that their good work will be seen and heard and is valued and they will get the resources to do good work. You’re going to have an engaged employee.

Allison: Absolutely.

I’m going to shift the conversation slightly to how to advance your career?

I’m a coach and I’m a mentor but in your book, you give some really good, straightforward, and practical advice about collecting mentors.

I have a vast level hierarchy, employees, leaders, executives, C-suites, business owners. We all need more mentors in our life in some way. What could you share with our listeners that has worked for you successfully to collect those around you?

Carter: Well, I’ve even gotten to the point where I don’t like to call them mentors because it’s a scary word for people.

You said the word mentor. Mentor means commitment. Like marriage, another M word that scares people.

Allison: What do you call it instead?

Carter: Seeking counsel.

Allison: Counsel. Yes. OK.

Carter: Counselors. Everyone loves to say they provide counsel.

Instead of saying,

“Would you be my mentor?”

You say to somebody,

“Allison, I saw that module you did on deliberate conversations and I thought it was fabulous, I learned a ton. Could I grab a cup of coffee with you some time and seek your counsel on an interpersonal issue and just helping you understand how I might approach it?”

Though, I flattered you by letting you know that you did a great job and then I’m flattering you by saying that I would love your words of wisdom on a very specific topic.

You’re going to say,

“Sure,” and I make it low impact, quick cup of coffee.

Then after we have our cup of coffee, you say,

“Thank you so much.“

By the way, when you have a cup of coffee, bring a notepad and take notes. Let them know that you’re totally listening and engaged in what they’re sharing. When we’re done, I say,

“Allison, this has been such a wonderful experience. Thank you so much. Do you mind if I give you an update when this is all done?”

And you’ll say,

“Sure, I’d love to know what happened.”

That’s your natural.

Step 2, you don’t do it right away. After you do that, you send a note and say,

“This happened and I wonder if your time in the future, it’s OK if we chats again. A time in the future.”

You say,

“Sure, I’d be happy to.”

I’m slowly reeling you in. I wait a few weeks. I say,

“Well, another thing came up, I wonder if you could give me your words of wisdom.”

You do this in a way that isn’t scary. You also allow for natural chemistry or a natural connection to occur.

Allison: For sure.

Carter: And if it doesn’t occur and it’s awkward, well, then that’s probably or you don’t receive a lot of feedback that’s useful, well, then, you don’t take it any further.

I think of this as not having mentors. I think of like, it’s a collage of experts who are good in different areas.

I talked to somebody about merchandising assortment planning, I talked to somebody about interpersonal issues around getting feedback. I talked to somebody else about business strategy.

I think of like that with my background of having a second mosaic of people that helped me in very specific areas and I don’t put too much burden on any one of them. I don’t think there’s like 1 or 2 or 3 mentors. I think it’s like 15 people that I can turn to on different topics now and again,

Allison: For sure.

I think one of the things I’m recognizing is I counsel a lot of people but I don’t get the feedback on what they’ve done with it and it feels like I’ve maybe wasted my time, right?

I just want to encourage that if you’re seeking counsel from someone and you get permission to follow up or let them know what they did, that it actually is more rewarding for the person who’s given you counsel to know that you’ve taken the advice and you’ve had feedback or that you’ve moved forward.

I think we always get worried that we’re going to waste someone’s time or that they’re not as invested but if they’ve invested the time to sit with you, give them being thoughtful enough to give them the feedback about what they did. Super important to activating that long term counsel, I think.

Carter: Great point.

Allison: Yes, that was an aha moment for me right there. Thank you.

Carter: That is such a good point. You want to hope that it was useful and when someone lets you know ex post facto, you feel good?

Allison: Absolutely. Yes.

Carter: By the way, after I’ve said Alison, that helped me so much. I just wanted to thank you. You usually respond with,

“I am happy.”

“I was happy to do it and I’m happy to help in the future.”

You usually provide a comment of,

“I’m happy to do it. Let me know if I can help you any other time.”

And then you sit on it and wait a bit and then if another opportunity presents itself, you approach them again.




That’s the way you develop that rapport. People come up to you and they say,

“Would you be my mentor?”

It’s scary. Just thinking,

“Oh, my Gosh! How much time is this going to require?”

Allison: All right.

Last month, Bob Iger shared the top 3 keys to his success and leadership.

He listed hardworking mentors and luck.

If you had to list 2 or 3 of your key successes and leadership, what would you choose?

Carter: Focus.

Morton Hanson wrote a book called “Great At Work” last year and he talked to huge quantitative survey 5,000 professionals and he found that the ones that were in the top tier of performance had an ability to focus and maniacally on a few things and do them exceedingly well.

I would agree. Well, when I read that I was nodding because I believe that by focusing and trying to do something exceptionally well and not trying to boil the ocean.

You get into all kinds of trouble when you try to do too many things, you just can’t do it all well and you’d rather do 1 or 2 or 5 things very well in the course of the quarter of the year and trying to do a whole bunch of things, it gets spread too thin.

The one is focus, without a doubt.

The second thing is, I would say being able to bring others along with me.

Realizing the business is like a team sport and that you can’t do anything alone in business. It’s so inner woven and interdisciplinary and business decisions are all integrated into decisions that are made by groups of people and so if you’re effective in listening to people, letting them know they’re valued.

Reciprocity, helping them when you can help them. If you’re someone that is a integrator and a uniter, I think you can go really far because people want you to be on the team with them.

I would say working well with others and bringing others along.

Focus and I think you’ve got to say luck, too.

Allison: Yes.

Carter: I believe that’s right. I mean, sometimes you’re in the right place at the right time and sometimes luck helps you a lot.

Sometimes bad luck hurts too but people say,

“Well, you can make your own luck.”

To some extent and you do your homework and you pick assignments and you pick companies and either pick bosses. By being diligent, you can make your own luck too.

Allison: For sure.

I truly do believe that the hardest working people usually have the best luck.

Carter: There you go.

Allison: For sure.

Carter, we’re coming to the end of our time together and first, it’s been such an honor to be able to speak with you so candidly this afternoon. Thank you so much.

I am a big promoter of your book, it is on our top list of recommendations that we make on our website.

Do you have any new books coming out that you would like to share or pre promote?

Carter: I don’t. I have a topic that I’m getting increasingly interested in.

Allison: What’s that?

Carter: Around transitions and how people can make good transitions in their lives. It’s just very interesting transition.

I think back in the old days, we could count on the tribe to help us with a transition and so you go out in the woods and there are these rites of passage that we used to have.

I think a lot of times now, our society is so individualistic. Sometimes you feel alone when you’re trying to go through a transition and you need help and so I’ve just got increasingly interested in this topic of how can we have help in making transitions.

The last book that I remember reading that was really good on this topic was by William bridges in 79.

Allison: Well, that it’s due for a revamp.

Carter: It’s due for a facelift.

Allison: The word transition comes up a lot in when working with humans and it’s funny people are very resistant to transitions and so we recorded as transformations that they’re going through so just to share that it’s a brilliant topic. I can’t wait to read about whatever it is that you create is.

What is the best way for people to connect with you if they would like to?

Carter: Well, I have a website. My name dot com.

It’s and if you just enter my name and Kellogg. This Kellogg School of Management, it has my email address there too.

Allison: Fantastic. Excellent.

Carter, thank you so much for your time today. I wish you a very happy Thanksgiving.

Carter: Thank you.

Allison: This coming week and we will share this as it gets posted. OK?

Carter: Thank you. It’s been a real pleasure.

I'm Allison Dunn,

Your Business Executive Coach

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