Building Influence, Maintaining Growth, And Handling Setbacks With Keith Willis

Maintaining constant career growth requires more than just sheer will. If you want to do this the right way, you must come up with effective strategies aligned with your strengths – and even weaknesses. Sitting down with J.R. Lowry is Keith Willis, founder of Core Management Training. Together, they discuss how middle management professionals can take on bigger roles by learning the right way to influence others (even if they are not in the place of authority) and build relationships that truly matter in their chosen field. Keith also explains how to use setbacks as keys to unlocking profound growth moments instead of simply getting stuck.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/keith-willis

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Building Influence, Maintaining Growth, And Handling Setbacks With Keith Willis

This show is brought to you by PathWise.io. If you want to take control of your career, join the PathWise community. Basic membership is free. My guest is Keith Willis. Keith is the Founder of Core Management Training, a firm that is dedicated to improving leadership team performance and business results. Intrigued by how high achievers succeed, Keith has spent his career studying, applying, and teaching proven strategies that drive results. In our discussion, we’re going to be talking about a few topics that Keith proposed, including how to build influence, mid-career growth, the transition from corporate life to entrepreneurship, and growth moments that feel like setbacks. Let’s get going.

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Keith, welcome. Thanks for joining me. As one veteran to another, after Memorial Day, thank you for your service.

Thank you, J.R. Same to you.

It’s always a good reminder of the fact that a lot of people have given their lives for the freedoms that we enjoy in the United States. It’s more than just barbecues and a day off.

It is a day to commemorate a lot of the sacrifices that men and women have made in this country.

Keith Willis Of Core Management Training

Let’s talk about you. Start with Core. Tell us a little bit about how you got started and what you do.

Core Management Training is a company I started. Like a lot of people, I was transitioned out of my role. I was surprised one day. I came in from vacation, and my boss wanted to speak to me. After thinking about things and doing some interviews and things like that, I didn’t realize that as you get older, there is this thing called ageism. I decided I was going to go out on my own. I always had an entrepreneurial streak. I did the Sprint phone cards, Amway, and some of those things.

I wanted to be able to help managers be more effective in their role. I helped stand up leadership development at one organization. One of the things that stood out is that managers get some training, and the pharmaceuticals do a pretty good job of training generally, but it’s not consistent. There are usually gaps. I felt like managers wanted practical tools, resources, and those types of things to help their teams perform at a higher level. I decided I was going to start Core Management Training. That’s what I’ve been doing for several years.

I would certainly agree with you that management training is something that most people don’t get. Most of what they get is either learned from the experience they have with their own bosses over the years or what they pick up on the job and learn the hard way. In many instances, most companies don’t do much at all in the way of managing training.

I would agree with you. I know you’ve worked mostly in the pharmaceutical industry. In general, that’s an industry that puts a lot of value on training employees, whether it’s about management or hard skills, or whatever. Most Industries are not nearly as good about that. You probably came from one of the better ones in the scheme of things.

I was fortunate that I got a lot of early training and participated in some good programs. That being said, a lot of times there are huge gaps in the industry as the industry has grown with downsizing and things like that. One of the first things that happens is that leadership development seems to disappear for long periods of time in major organizations.

More and more, there’s a need for outsourced L&D in most companies. Even bigger companies decide not to invest in it and have full-time staff on board. They may do a little bit, but then they go outside for more of it, and that creates opportunities for companies like you.

The interesting thing is that training in some cases is a developmental opportunity. You have a huge switch-over of people on a regular basis. Sometimes, a manager may even come in and do leadership development. They’re looking for the next assignment. In some cases, you have people who will stay for a while, but that creates a level of turnover, and then there are always opportunity costs. Where should I spend my time? I’m a tactician. I want to be somebody who focuses on strategy. That does create opportunities for me.

Career Growth: To be a good leader, you have to be a good follower.

Who are your clients? What do you help them with?

Primarily life sciences, pharmaceutical companies, and companies that support pharmaceutical companies. I’ve done work outside of the industry, but because that’s where I spent many years of my career, it’s what I know very well. It could be anywhere from coaching and feedback, skill and competency modeling. I was at a workshop.

I don’t know if you’re familiar with the 14 Peaks documentary. I built a leadership workshop around that, around accountability and followership. Just practical skills. We’ve built case studies out of situations that were happening in managers’ areas where they struggled, so that the opportunity can be role-played and discussed through some of those challenges and issues. At the same time, there was some self-reflection on whether I am the type of leader that people want to follow.

Even when companies are doing training for managers, what do they miss that’s important?

I would say the pull-through. We have a tendency to think that we’re going to do a program, it’s one and done, and people are going to get the skills. I was fortunate that over my career, I worked in different organizations. There are these repetitive themes that go on. For example, things like emotional intelligence. You may pick up one or two things about emotional intelligence, or you can go through a coaching workshop. You learn some different methodologies.

If your manager doesn’t provide follow-up, feedback, or even walk you through in real-life situations when you’re having a challenge with one of the people on your team, and walk you through using that framework, a lot of what’s being trained is lost. It’s the ability to be able to translate what’s trained into real-life scenarios, and then be able to use that on a regular basis.

You suggested some topics for us, like influence when you’re not in charge, mid-career growth, and growth moments when you’re feeling a sense of setback. How did you pick those topics? That’s what we’re going to cover.

Part of it is, in some ways, it’s my path. It’s the path of many people who are in Corporate America. Even if you’re in charge, you’re still trying to influence people. There are people above you. There are people below. You can’t always wear the boss hat to get people to do things that need to be done. There has to be some level of influence. My life experience has been that the more you focus on developing those skills, the more effective you’re going to be as a leader, or even when you work within a matrix organization.

Everybody has setbacks, and they can look like their fatal, which can be difficult, and some of those transitions and growth. We’re always in a growth period, whether we know it or not. Even if you’re a new sales manager and you’ve just gotten this big promotion, it’s like a new sales rep. You’re starting all over again. There’s that constant cycle.

Understanding The Power Of Influence

Start with influence. I had a show guest who has a book out at the moment. In it, she relates a story of having to work on this big project and being stretched. Nobody worked for her. It was all an influence situation. At the end of it, her boss said to her, “You were effective. Spend the rest of your career acting like the people who work for you don’t work for you, and focus more on influence.”

It was a great example of how powerful influence can be. You talked a minute ago about matrix organizations. More and more, organizations’ structures are so bloody complicated that you are very often working with people who don’t work for you, and needing to get things from them, and work collaboratively with them. If you don’t have influence skills, it can get in your way.

I would agree with that. This is one of the things that I think about. There is this formula. I believe it’s by Charles Green, and it’s the influence formula. It talks about credibility plus reliability, plus intimacy, and divide that by self-orientation. If you think about the credibility of the skills and the knowledge that you bring to the table, that background is why you are hired and what your professional expertise is.

It’s how reliable you are. Do you do what you say you’re going to do? Can people rely upon you? You build a storyline within an organization around those elements of it. In most organizations, even in the military, everything is driven by relationships. The better your relationships are going to be, the more effective you’re going to be at getting things done. If you look at those three areas and if you have gaps in any of those three areas, you’re going to struggle in influence.

The last piece is self-orientation. The more focus that you have on self-orientation, the less you’re influence is going to be because it’s all about me versus it being about everybody else. I keep that in mind when I think about, from an influencer standpoint, how I can be better at that. That’s a good formula, whether you’re leading a team or you’re a part of a matrix team. Even when you’re leading a team, you end up on a project where it might be all your peers on the leadership team. You have to get something done or you’re running a meeting. You’re still using those skills on a regular basis.

When you do your training work on this topic, how do you shift people’s mindset from needing to be the boss and needing to be in control to being more focused on cultivating impact and giving up some of that self-orientation that you mentioned?

It’s a challenge because people get wrapped up in the pieces of the job. When you talk to managers, oftentimes, it’s more of, “Do what I tell you to do.” There’s this expectation of that. We know that doesn’t happen in life. I don’t know if you have children or not, but your kids don’t even do what you want them to. What would make you think that would happen at work?

You can get people aligned by looking at the impact and outcomes that they want to have, and start from there. Think about how you want people to see you. When you spend time in an organization, do you run a team where people are looking at you and saying, “I want to work for that person?” That’s influence when you look at it from that perspective.

You mentioned emotional intelligence earlier in the conversation. How does that play when you’re not the boss?

Emotional intelligence is a big tool. Data shows that people who are more emotionally in tune with others and their feelings, as well as how they impact other people, get more promotions and do better. I’m certified of to do emotional intelligence through TRACOM. I know there are a couple of other methodologies. Ultimately, they all say the same thing. The higher level of emotional intelligence, the more effective you’re going to be.

A lot of those skills can be learned. Some people have a more natural tendency around them, but you can be better at that. I like to think about it from this perspective. To be a good leader, you have to be a good follower. You have an opportunity to think about how I am showing up from an emotional intelligence standpoint when I’m following somebody. You don’t always agree with people on your team.

Sometimes, that person is your manager or your boss. How do you interact with them? That plays itself out when you get into a leadership role. You don’t just change overnight. You’re the same person who was in the previous role. When you’ve gotten promoted, hopefully, those skillsets are going to be things that you’re going to contribute and continue to use.

What mistakes do you see people make when they try to influence in the middle?

One is trying to be in charge. If you go back to the influence formula, have you established any level of credibility? Which makes you the expert? Are you the one who’s trying to bring everybody in on the team? How reliable are you? It’s thinking about it from that standpoint. People are such in a rush to figure out the outcome that they don’t think about what are the relationships that they have.

If you focus more on those things, as well as what you’re trying to get accomplished and making sure that all the voices are heard, from an influencer standpoint, you can be far more effective. Part of it is that the corporate sets it up this way. It’s this very competitive landscape where everybody is trying to get ahead. You spend so much time competing that you forget about what the mission is and what it is that we’re trying to get accomplished.

It comes back to that formula that you mentioned. People often get very transactional because they’re under pressure, they have to get something done, and they have a deadline. It becomes about them. Probably a little bit like networking, you’ve got to build influence when you don’t need the influence. If you build credibility, reliability, and intimacy when you’re not under the pressure of time, and if you build that habit of give and take that comes with being less self-oriented, you’re hitting all those different components of that equation when you don’t need it.

When you do, when you need it, and you’ve got to call in a favor, people know like, “I know this guy doesn’t come out and ask me for favors unless it’s important.” You build that relationship capital over the weeks, months, or years. When you do need those favors and there is an urgency to them, you can draw on them. If you don’t get in front of it, then trying to build influence when you have a deadline ticking is hard.

It is, and people miss that.

What do you do when you’re out there and you’re doing everything in the right way, but you still face resistance from people who don’t see your value? At best, they are apathetic. At worst, they are openly trying to get in the way of you getting your job done.

That’s part of the human condition. Everybody is not going to necessarily like you or see the value in what you do. At that point, it’s a good opportunity for you to ask for feedback. Sometimes, there are behaviors or things that you’re doing that you may not realize are taking away from your influence or from the value that people see. I also think, at times, it’s time for you to take a step back and think about where you are. We’ve all been in organizations where maybe we’re not a cultural fit. Maybe it’s not that you don’t bring value. It’s just that maybe people feel threatened by what you bring to the table.

How it shows up is the apathy and the unwillingness to help. It’s usually not a credibility issue because if you’ve been hired and somebody brought you into the organization, there was a reason they brought you into the organization. In some cases, it may not necessarily be a reliability issue. It might be that they just don’t like the way that you do things. In some organizations, we talk about innovation. I don’t know that everybody always believes in innovation. If you go to any marketing team or any sales team, there’s a tendency to do the same thing over and over again.

Part of it is because of their safety. There’s a lot less risk. As soon as somebody brings in something different, people are threatened by that. What do they do? They respond and react. I do think the last part of that is that you have to look at your relationships. Do you have advocates? Do you have people who can advocate for you, support your cause, and maybe do some of the heavy lifting for you when you’re trying to get something accomplished?

Influencing Your Bosses And Higher Ups

Do you feel like there’s anything that you need to do particularly differently when it comes to influencing your boss, their boss, or somebody in the senior leadership team of your company?

I do think there are very specific things that you can do. Not every manager does a one-on-one. In some organizations, that’s the culture. Everybody does one-on-one, but the reason you do want one-on-one is not necessarily to get an update, but it’s to build a professional relationship. Starting with your boss, your boss is the most important relationship that you have in any organization because they’re the ones who talk to their boss about you.

When I have coached people, the first question I’ll ask is, “Do you do one-on-ones with your boss?” Usually, that’s initiated by the manager who’s in charge, but some managers don’t do that. I’ll make the recommendation to reach out. You don’t necessarily need to call them one-on-one, but you get some time on your manager’s calendar. You do the same thing. You think about skip-level meetings that you can have what your managers, just so they know who you are and have an idea of what you’re doing.

Ultimately, you’ve got to build your own brand. No one is going to do it for you. Your manager has their own challenges and issues. They may have 30 minutes with you weekly, or you may work on some projects and things like that. No manager ever knows completely what you’re doing 100% of the time. That’s one of the challenges or one of the issues around when we talk about remote work. Your manager “can’t see you.” Even though in some cases, they’re in a meeting all day, there are those things that go along.

I do think that’s the number one thing is doing a one-on-one and getting visibility. The other thing is nighttime projects. We call them nighttime projects because they’re outside of your day job. Those are the things that get you exposure within the organization if you’re looking to climb the ladder and you want to get some exposure. Raise your hand for some projects, some initiatives, and things that will give you some visibility that can showcase your skills.

The last part of that is that you have to network within your organization. It can’t always necessarily be within the group that you work in. Expand your horizons. Talk to other people in the organization and get a better understanding of how the organization runs. It may even be as simple as thinking about, “Here are some things I think I might want to do. Let me do a little bit more discovery.” AI, for example, is the big rage. I don’t think there’s anything wrong with that. Maybe there’s a new department that focuses on that.

Have a discussion with them. It’s not because you want to do that job, but to get some insights into how you can use AI more effectively in your role or in a unit that you’re working in. What does that look like? What’s coming down the pike? Those are things that somebody can do to build their network within the organization, not only with their manager, but with their boss’s boss and throughout the organization.

You made a couple of points that resonated as they related to bosses who don’t necessarily do one-on-ones. When you get yourself in one of those situations, you have to find a different way to stay close to your boss. As you said, they are the most important relationships for you in that company. They hold the keys to your future with the company, your growth, and employment. First and foremost, that rests with your boss. If you don’t feel like you were in a position of at least some influence with your boss, that’s not a great place to be.

Career Growth: Your boss is the most important relationship you have in any organization. They are the ones who talk to their boss about you.

If you can’t change the way that they’re viewing the relationship, then you’ve got to change the way that you view the relationship and manage the relationship. You’ve got to find ways to stay top of mind for them because if you don’t do that, then the risk you run is that you fall into a negative cycle with them. They don’t see the value you’re adding, and because you’re not there doing a little bit of self-promotion in your one-on-one, if you’re not having them, you’re not finding ways to convince them that you’re bringing value to the organization.

Some people get into those situations with bosses like that, and they give up. At that point, you are giving up because sooner or later, you’re going to get let go. Even if you’re doing a great job. If you’re doing a great job and it’s not visible and not recognized by your boss, the odds are that’s not going to work out well for you. There’s this adage of owning your career. I view that in the strategic sense. You’ve got to own it in the tactical sense. If your relationship with your manager is not working, something needs to change.

It’s interesting because my mentor for American Corporate Partners, we do help people from the military transition into corporate. One of the gentlemen has a different mentoring program, and he’s been working full-time jobs, so his manager did not do one-on-ones with him. He had some level of frustration about getting promoted. Part of the conversation was building in time where he had one-on-ones with his manager. He also began to go out with his manager, but also had conversations with his manager’s boss, and some other people he was interested in getting a better understanding of.

Ultimately, what he wanted to have happen is for him to get promoted. Now, he hasn’t been promoted yet, but he feels a lot better because he’s getting more opportunities, more people know him, and people have conversations about what succession planning might look like for him, and opportunities or experiences that he may want to get.

It has enabled him to take control of his career and, at the same time, to make some practical decisions. I’ve been at this organization for a while. It’s this organization that I want to stay with. Other people are now beginning to show interest, and it has helped him make a decision that he’s going to stay put. To your point around people taking control of their careers, it does start with keeping your manager in the loop with all the things that are going on, but at the same time, building that advocacy outside of your group.

Leading And Growing In Mid-Career

Let’s switch gears and talk about another one of your topics about how to lead and grow in the middle of your career. From your perspective, what does growth even look like for somebody who is mid-career but not quite in the C-suite?

Most people end up in middle management. Everybody can’t be in the C-suite. There’s only a small percentage of people who make it that far. A lot of managers make the mistake that once they get to a role, they think they’re finished, and that there’s no more growth and development. They may say, “I’ve been doing this role for the last 10-15 years.” You always have to focus on your growth and your development, whatever that’s going to be.

I think about the stage of life that I’m at now. A lot of my peers are retiring, but there’s a lot of gas in the tank that they’re allowing at the end, what you want to be able to do, whether it be starting your own business, doing non-profit, or whatever that is. Peter Drucker wrote an article about managing yourself. He talks about being prepared to do another career and focusing on that.

Even if somebody is in middle management, they can look and say, “What am I going to be doing in the next ten years or so?” It’s not too early to be thinking about, “That may look like something different. Are there some other things that I could start focusing on and developing on. Is there a dual track that can help me in my day job and help me transition to something else?” When you look at the amount of content information and things that are available, it’s hard to keep up just to be average in the current job that you’re doing. You always have to be developing yourself in some way.

How To Not Feel Stuck In Your Career

How do you counsel people who are contemplating a lateral move? Under what conditions does making a move from an organizational level perspective or from a corporate title perspective is a sideways move? When is that a good idea, and when is it a bad idea?

Most times, it can be a good idea. It depends on where you’re going. I’ll give you an example within pharma only because that’s the world I live in. Let’s say, as a sales representative, somebody goes in as a sales rep through sales training and a developmental position, and then they become a district manager. There’s a band of district manager positions. They call them promotions, but they’re not really promotions. Somebody who is an AD or associate director, for example, is still considered a district manager position.

In some cases, that might be an individual contributor role, which might be in reimbursement. You might go to market access, where you are doing negotiations and working with contracts. When you’re doing a lateral, while it may not necessarily be a real promotion, you’re building additional skills. When you get to the next level, let’s say you’re going to be a second-line leader, what they’re looking for is those people who have more touchpoints. They have a broader understanding of the business because they’ve been in roles that would be “considered” lateral.

Even if you think about the military, a captain may be a company commander, and then they become a staff officer. They have some staff assignments and do some other things. If they’re competing for somebody to become a battalion commander or even a brigade commander, they’re going to look at those touchpoints. Those folks who have a broader range of experience, even though they were theoretically lateral moves, have a broader level of experience. When we talk about looking at the business, whether it be the business of being in the military or the business of, whether it be corporate or pharmaceuticals, a broader understanding of the business grows and helps you from a lateral perspective.

I would go back to what you said at the very outset. I would agree that, in general, lateral moves have the potential to be good moves because you work in a different function or a different team. You’re seeing a different management style. You may be learning a new function that you haven’t worked in before. All of those things build your credibility and your readiness to move up closer to the C-suite. I think about my own career. There were times when there were jobs I thought were going to be great that didn’t turn out to be great. There were jobs I didn’t think were going to turn out to be great.

Career Growth: You have to ask questions to make people become more than willing to work with you.

Things can turn better or worse with one or two people changes or situational changes in a team. You’d never completely know. You have to be open-minded about some of these lateral moves because they get pitched a lot. Somebody above is looking for you to potentially solve a hole that they’ve got. You’ve got to be able to open-minded about them. You also have to be a little bit stooped and not blind, and put blind trust in somebody else necessarily having your interest in mind, but you can learn so much from those situations.

Over the years, I worked in pretty much every function organizationally and did a little bit of enough things that I feel very comfortable across most functions in a lot of different business situations. It comes with the gray hair and what’s left of it. It also comes with the willingness to step into things that were outside my prior experience base, and to be committed to learn in those situations. If you do those things enough, career are long. You and I are roughly the same age, with gas still in the tank. You’re not working till you’re 55 or 57, like my father-in-law did. You’re working potentially well into your 60s, so you’ve got time.

You’ve got time to try some different things. You’ll look back when you get to be further in your career and say, “I’m glad I did all these different things because I learned so much in so many different places.” People feel like they need to climb step by step on that ladder, and there’s no going sideways. That’s a very narrow view.

The other part of that is that people move from organization to organization. Even when you take on roles that are similar to the previous role, sometimes they have more responsibility. I remember going from one role level-wise to another role, but the role that I went to, even though they theoretically had the same title, the role that I went to had more responsibility. I had more budget responsibility. I had more direct reports. You can build upon skills that you learn from your previous role. Even though they are theoretically the same in title, they can be very different.

It’s interesting that you mention that because a lot of times, I’ll talk to people. I’ll talk about my background and everything. They’ll say, “You’ve had a great career.” I’ll be there thinking to myself. It’s like, “There’s so much more I wish I could have done.” This is how we’re wired. You’re ambitious and you’re trying to do the next thing, but I was also always trying to get as much experience as I could.

Time goes by quickly. I started working in the late ‘80s with military experience. We talked about it at the outset. I got to do a few different things, all with an engineering bent. I spend some time consulting. I’ve worked in financial services and a few different places, and 35-plus years went by very quickly. How do you counsel people who are in that mid-career, “I’m feeling stuck?”

It’s an interesting question because I always start with, “What does that even mean when people say they’re stuck?” I think the other question is, “Where do you see yourself? Where do you want to go?” Part of the stuckness is that somebody has been working in an organization for 20-30 years, the proverbial golden handcuffs, where they feel like they don’t have options. At that point, there’s a financial consideration because you’re going to retirement, and you can get full medical. You’ve got two or three years, or maybe you’re young enough. It’s never too early to start thinking about what that transition looks like. “What do I think I want to do?”

I tell people that you never know because sometimes you might not get a chance to raise your hand and say, “I’m going to retire.” The company might say, “It’s been nice. We’re doing a downsizing, and you seem to fit the criteria of what we’re looking for.” All of a sudden, you’re starting over again. I’ve given that some thought earlier. Let’s say you’re going to go out and you’re going to consult. There’s an opportunity to maybe get some certifications or go to some different classes.

It’s helping people take control of where they are and what they’re trying to accomplish. I remember talking to somebody who was in insurance. I was having a conversation with them. There’s a level of fear because you have to spend some time with yourself. You get some paper and a pencil, sit down, write some stuff down, and think about where I want to go and what I want to accomplish. Nothing is going to change unless you change.

The first part of that is sitting down, and even if it’s brainstorming, whether you get a coach, sit down with your spouse, or get some time alone and write out. You still have dreams, ambitions, and things that you may want to accomplish. We put so much of our identity into our work. That can be one of the challenges when people either retire or get laid off. They’re identity is so wrapped up in work that they have no other outside interests or anything like that, so they struggle. When that question gets posed, there’s a level of fear. It’s easy to do nothing. As I said, nothing is going to change unless you begin to take those first steps.

There are so many ways to do it. It goes back to what we’re talking about a minute ago, lateral moves and moving into a different company. There are so many ways to get yourself out of whatever sense of malaise that you’re feeling. As we talked about, you’ve got time and you can do different things. There’s an adage. In any job, you should be learning or earning. It’s great when you can do both, but if you’re learning, you will be engaged. You will feel a sense of fulfillment. You will be happier, which will ripple out to your personal life.

Part of the reason people get themselves stuck is that they either set overly lofty ambitions or overly aggressive timelines for themselves that aren’t realistic in most situations. As you say, only a few people get to be in the C-suite in any given company. Also, more often, it’s because they think too narrowly. They aren’t willing to get out of their comfort zone and commit to doing something new. They keep going to work, doing what they’ve been doing, and they get into such a flat line routine that they lose that sense of enthusiasm. That’s when you get mid-career people who are not trending in the way that they ought to be.

There are so many companies, depending on their size, that there are other business units. You can go and do other things. In some cases, you have companies that have a company within a company. You can raise your hand and say, “I’d be interested in going over there and see if I can help out do some different things. I’m looking for some different experiences.” At a minimum, you’ve got to ask the question. If you ask the question, people are more than willing to work with you. If you don’t ask the question, no one is going to know what you’re thinking and what you want to do.

Being clear and being communicative about it is a prerequisite. If you don’t know what you want to do and you’re not telling other people what you want to do, odds are they’re not mind readers, and you’re not going to get to do what you want to do. You have to have that perspective. I’m sure you work with your share of mid-level managers.

They go from not even knowing how to be a manager to getting the managerial basics, to then learning how to lead. Management and leadership are like a Venn diagram in a way, but clearly, when you move into bigger roles, the management probably gets a little bit less important because you’ve got very capable people underneath you, but the leadership matters more. How do you help people begin to make that transition in the work that you do with them?

Part of it is skillset because it’s more about vision and leading people versus managing things. We manage things in processes and things, but we lead people. It’s easy for people to forget that. It’s being able to get them other experiences and those types of things. I did Toastmasters for many years. I took over our club. At the time I was in the club, it was 50 years old, and we were struggling because we had moved locations and membership had dropped off.

We talked about influence earlier. No one worked for you, even though you’re the president of the club. The only thing you have going for you is influence and building out a vision of what the future might look like. It was one of the best developmental lessons I learned outside of Corporate America because I wouldn’t have had the opportunity to learn that skill. Usually, you’re thrust into a role, especially if you’re a second-line manager, all of a sudden, you’ve got a team of direct reports who have direct reports, and you’re setting the ball forward.

If you can figure out how to get those experiences also outside of your day job, it will help you be more effective as a leader because you can learn some lessons. The risks are different. You’re not looking at P&L and some of those things. It’s not that nonprofits and other organizations are not important. They’re going to be a little bit more forgiving. There are some valuable lessons to be learned there, and in whatever classes.

We talked about the lack of leadership development and leadership training. Finding good mentors is so important, and being able to talk to peers who have been where you have been and who can give you advice, suggestions, and things that you could be doing, as well as using some of the tools that are available within the organization.

A lot of companies do 360s with the leadership team and those types of things. Be open to feedback and improving, and being better. We have conversations. Sometimes, you have different relationships with people on your team. Ask people, “What would you like to see differently? What are some things that I could do that will make things more effective?” If you approach them in the right spirit, people will give you the feedback to help you do the things that you need to do to be successful.

How To Handle Setbacks And Grief

Let’s talk a little bit about setbacks. It’s another topic on your list. How do you help someone recognize that what feels like failure or the worst thing that ever happened to them might not be such a bad thing?

You can start with personal stories. I’ve had my fair share of setbacks. It’s how you get to where you are. It’s having those stories. I used to always joke with people. I would say that I never wanted to work for a sales manager who had never struggled as a sales representative. They have no insight into what it means not to do well. I remember when I was interviewing for a job, and I decided not to take the role because the manager had never struggled.

It was a district manager position in the Philadelphia area. You either do well or you don’t do well, and she was a new regional director. I was thinking, “This has a chance of going south very quickly.” I hope people ground them and focus on what the lessons are. What are you learning here? Help them see that it’s not the end of the world, and do share some of those lessons. I remember being a new trainer and getting some feedback from the class that I didn’t do the role play well, and I was too difficult.

My manager made a decision that I was going to be retrained. I was going to retrain with one of my peers who we had come into the sales training at the same time. I was crushed. One of the guys in HR was my mentor. I remember he had a conversation with me. He was telling me, “It’s going to be alright. You’re in this position. You’ve got a great future. You need to suck it up.” He gave me a pat on the back and a kick in the behind at the same time.

Later on, at the end of that year, I remember the director of sales training saying that was one of her greatest accomplishments because things could have gone either way. Things could have gone south, or they could have been very successful. Ultimately, I ended up as a district manager. It’s a huge opportunity for growth for me. It’s frankly what it was, and being open to accepting the feedback, me getting help, and having a broader understanding because she had gone to the same HR person. It was an HR professional who handled this, knowing that she had taken it seriously to figure out how to coach this person on your team to be better.

I use that as an example to say all is not lost. There are times in your career when you’re going to have setbacks. If you’re not having setbacks, you’re probably not growing. There are going to be times that you’re going to be put in positions where you don’t have the skillset and the ability to do what’s being asked to be done. There’s a huge growth opportunity for you.

When you’re working with somebody in one of those situations, how do you balance being empathetic but at the same time, providing enough challenge to them to work through it?

You have to help them get through the stages of grief as quickly as possible, and then have the conversation about what we are trying to accomplish here, and what the results are that we’re looking for. Get them to agree that there is an issue, a problem, or something that needs to be solved. If you can’t get them to read that there’s an issue or a problem that needs to be solved, you can talk until you’re blue in the face, and no action is going to be taken. Once you can get to that agreement that there’s something that needs to be solved, then I’ll have the conversation about how we do that, what that looks like, and what that development looks like to get you to the next level. What does that end result look like?

Do you feel like people try to rush themselves through the stages of grief or through getting past the setback? Do you counsel them to be more patient?

My experience is that people usually stay in the grief stage too long. One of the things that I’ve seen in a lot of organizations is that we don’t do a lot around change management. A lot of organizations don’t teach managers. Change management can be anything from a new role to coaching and providing people with the skills to be able to get out of that grief cycle. What happens is that the grief cycle keeps going on. Ideally, what you’re trying to do is get people out of that grief cycle as quickly as possible. They’re still focused on the past when there’s an opportunity in the future ahead of them. Part of it is human nature. How do you coach that? My experience has been that most people stay there too long. I don’t know if you’ve seen something different.

Especially if it’s a layoff, there’s an economic dagger hanging over people’s heads. They’re thinking, “I’ve got to find employment because I need to provide for my family or myself.” They don’t feel like they’ve got the luxury of time. They end up jumping right into the first thing that comes by, and it ends up being a bad move for them. There are no easy answers in those situations. The wisdom of having a security blanket in the form of savings that you can tap into for just one of those situations, people used to call it “F you” money.

When you get laid off, it could be more “F me” money. In the scheme of things, having that gives you a little bit of latitude to not feel so much pressure to jump right back into something new, but not everybody has the luxury of having bank savings. Those are situations where people do feel like they’re rushed.

When I worked with people who have felt that, the best advice I tried to give them was to think through what’s important to them in a job. It comes down to, “How do I feel about my skills and the job market? Do I take this one, knowing that it may not work out because it doesn’t feel completely right to me, but I need income, or do I wait a bit longer?

Everybody has to form their own judgment. Other than that situation, people tend to linger in the grief cycle longer than they should. They get stuck in the bitterness or the disbelief that something has happened to them. You’ve got to push them out of those situations because at some point, they’ve got to get on with their lives, like any other setback. The more they happen to you, the more you accept them as a fact of life, and you know what to do.

It’s like being a salesperson. When you lose your first deal, your heart breaks. You think it’s the worst thing that’s ever happened to you. Though you never want to lose a sales deal or whatever is a win in your particular job, you do come to accept that you’re not going to win every deal. Your job is to learn from them, so you increase your winning percentage. You’ve got to move on and not let it completely erode your confidence that makes you not a good salesperson or not a good whatever.

That makes perfect sense, especially with so many companies downsizing and the economy. It’s interesting, too, because part of the grief cycle is that people jump into the first thing that they get, and there’s a level of resentment that can occur. Instead of moving to the next thing and saying, “This isn’t a fit. It did what it needed to do. Give me another two or three months to polish up my resume. It would help me prepare for whatever that next role is going to be.” Sometimes people get stuck, and then turn around ten years past, they are in a job below their skillset. There’s a level of resentment from the situation and things that have occurred in their careers.

People talk about one-way doors and two-way doors. Most things are two-way doors. You can reverse the decision you’ve made. Some things are legitimately one-way doors, but when you get in those situations, it comes back a little bit to what we were talking about earlier in the conversation about people feeling stuck or questioning a lateral move or whatever. These are not life-ending decisions. If it doesn’t work out, you accept that. You prepare and you move on. If it does work out, then that’s fantastic.

Looking Back To Keith’s Career Transition

Sometimes, people either fear making the leap into something, or they get into it, and then they fear making the leap out of it. It comes back to what we talked about. People start putting themselves on autopilot in their careers, which isn’t great. Maybe spend a few minutes talking about your own transition. What surprised you the most when you left the corporate world and started your own business?

That’s a loaded question. The first thing is that everybody says, “I’m going to work with you.” I’m like, “That’s not true.” The other thing is that I spent time on the wrong things. It’s a learning process. I would joke with people and say, “You have to get the corporate beat out of you because you’re the decision maker. You get to make all the decisions, and you get to do all of the stuff.” You’ve got to figure out, “What am I good at? What can I afford to offload to give to other people?”

At the end of the day, it’s understanding that I’m the number one problem with everything that’s not going well. It is a journey of self-development in a lot of ways. My experience has been that the more time I’ve focused on myself, building myself, and making myself better, there’s a direct correlation to that and growing the business. Those are some things that were surprising.

Career Growth: Learn how to not focus on the past when there is an opportunity and future ahead of you.

The other part of it is that there’s a level of disbelief. I focus my business on life sciences. I would go to conferences and things like that. People would still see me as “the training lead.” People would say, “How are you doing?” There’s this level of concern they have about you. I would get sucked into that because you end up in this conversation. It’s understanding I’m growing a business. I need to present myself in a different way for people to understand that I’m growing a business, and I’m no longer doing this. I’m now doing that.

There’s a piece of that in a transition, where you transition from being this corporate person. It’s a part of my identity and who I am. It helps me in my business because I was a manager. I did a lot of things for the clients and people that I’m serving, but there’s that whole piece of understanding that. The other part of this is that there are some lessons you’re not ready for, or you focus on the wrong lessons. I remember I was trying to figure out how to run an event. I don’t need to learn how to run an event. I run a couple of national leadership meetings. I knew how to do that. What I needed to learn how to do was build an email list. A lot of people will sell you a lot of things, and sometimes, they’re not the right things.

Email lists are probably one of those things.

One of those things is trying to figure out how to do that early. In business development, selling in pharma, where you have a list of physicians that you see on a regular basis, is a lot different than doing regular business development. There are a lot of skills that have to be learned, and getting used to not getting a regular paycheck. My wife, at times, I’m amazed that she went along with this whole thing because it is a leap of faith.

I’d say the last thing. I don’t know if you’ve ever seen it this way. People would talk about how brave I was to go out on my own. It took me a while to understand that. It gets back to some of the conversation we were having earlier about people getting stuck, and not willing to take a risk and do something different. I took some chances. Part of me was, “If this doesn’t work out, I can always go back and find a job.” I didn’t want to look back over my career and know that being an entrepreneur was something that I had always wanted to do. I didn’t want to look back and say that I didn’t try it. At least, if it didn’t work out, I could say I tried and it didn’t work, then I went and did something else.

For me, that was something that was important. Essentially, you’re leading away in a different way because people see you, and it gives them hope. It helps them to be able to step out on faith in whatever it is that they want to do, whether to go get another job or whatever. They admire that. I’m not sure I still see it as a big deal. It’s me and who I am and what I want to do. I do understand it’s important to work with people and have conversations about what’s next and transition.

In that spirit, what’s next for you?

Keep building the business and keep doing this until I decide that I want to take a step back, speak, pick, and choose what I want to do. My kids are out of the house. I’m having a ball doing this, and helping as many people as I can, like managers, to have an impact on so many lives. If we can build better leaders and better managers, we can build a better world.

Thanks for doing this with me. We covered all of your topics at least a little bit. We’ll give ourselves a check on that. It was good to get to know you, Keith.

It was good chatting with you, J.R. Thanks for inviting me on. I’m looking forward to this episode.

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Thanks to Keith for joining me to discuss influence mid-career growth, dealing with adversity, and his transition into entrepreneurship. As a reminder, this discussion was brought to you by PathWise.io. If you’re ready to take control of your career, join the PathWise community. Basic membership is free. You can also sign up on the website for our newsletter and follow us on LinkedIn, Facebook, YouTube, Instagram, and TikTok. Thanks, and have a great day.

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About Keith Willis

Keith Willis is the Founder of Core Management Training, a firm dedicated to improving leadership, team performance, and business results. Intrigued by how high achievers succeed, Keith has spent his career studying, applying, and teaching proven strategies that drive results.

He began his leadership journey in the U.S. Army, where he built and led high-performing teams under pressure. He later transitioned to Corporate America, bringing a sharp focus on performance improvement across sales, operations, and training functions. In the pharmaceutical industry, Keith held roles as a top-performing Sales Representative, an award-winning Sales Manager, and a respected Training Leader at companies such as Johnson & Johnson, Pfizer, and Bristol Myers Squibb.

Today, Keith works with organizations and individual leaders to uncover practical solutions that elevate performance and build stronger teams. He lives in the Philadelphia area with his wife, Lorre.