How To Be The Best COO And Build Better Relationships with the CEO

Last Updated on November 9, 2020 by Owen McGab Enaohwo

The Chief Operating Officer or COO is an important thought leader of any company. If you’re looking to be a COO, trying to be a better COO, or you’re new to the job and you want to know the ins and outs, potholes to avoid, and best practices of being one, then this episode of the Process Breakdown Podcast with the host Dr. Jeremy Weisz is for you.

Dr. Jeremy Weisz features Bill Shepard, the founder, and CEO of the Chief Operating Officer Business Forum, a company aimed at creating a safe place where chief operating officers can find peer support, guidance, and collaboration to help them succeed in their jobs.

He speaks about ways COOs can have better and more meaningful relationships with CEOs, as he has been in both positions, and also shares the challenges that come with being a COO and how to overcome them.

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Key Resource List:

COO Forum

COOs in Transition

Show Notes:

0:05 – Podcast introduction

00:47 – Dr. Weisz talks about SweetProcess, an SOP software that makes it drop-dead easy to train and onboard new staff and save time with existing staff. It is used by hospitals, banks, and first responder government agencies that use it in life or death situations to run their operation. He also highlights their 14-day free trial.

1:30 – Dr. Weisz introduces the guest speaker, Mr. Bill Shepard.

2:20 – Mr. Shepard shares some of the ways COOs can create an amazing relationship with CEOs.

8:04 – The guest talks about the COO’s journey; the good and the troubles of every emerging COO.

10:05 – Mr. Shepard gives a list of things and the kind of attitude every COO should bring when having a meeting with the CEO.

11:26 – Mr. Shepard shares the winning way a COO can create a meaningful relationship with a CEO.

13:50 – The guest speaker shares a story on staying in your domain as a COO and showing respect for the CEO’s decision.

18:23 – The guest shares another example of the key things to do when trying to build a strong relationship with the CEO.

20:00 – Mr. Shepard talks about the most challenging thing for COOs and how to overcome the hurdles.

21:43 – Mr. Shepard gives an example of a challenge most COOs face when building a relationship with CEOs and how to get through it.

24:20 – The speaker shares a valuable way his company, Chief Operating Officer Business Forum, is helping COOs who have been or would be furloughed or laid off. He gives another example of the downsides and difficulties in the role as a COO due to these uncertain times and how to resolve them. 

26:58 – Mr. Shepard gives his solid, final advice for COOs and CEOs from his experience as both.

28:30 – Mr. Shepard talks about his journey from CEO to COO.

31:43 – Outro

Guest Profile

Bill Shepard is the founder and CEO of the Chief Operating Officer Business Forum, a company aimed at serving with integrity and creating a safe place where chief operating officers can find support, guidance, and collaboration to help them succeed in their jobs.

For more than 25 years, Bill Shepard has been CEO, divisional president, and COO in various companies and industries throughout the United States, including the health sector, manufacturing, and retailing.

Transcript of the interview

Speaker 1: Welcome to the Process Breakdown Podcast, where we talk about streamlining and scaling operations of your company, getting rid of bottlenecks and giving your employees all the information they need to be successful at their jobs. Now, let’s get started with the show.

Dr. Jeremy Weisz: Dr. Jeremy Weisz here, host of the Process Breakdown Podcast, where we talk about streamlining and scaling operations of your company, getting rid of bottlenecks and giving your staff everything they need to be successful at their job. I’m going to introduce you today, Bill Shepard in a second, of a Before I do, this episode is brought to you by SweetProcess. Bill, I always ask if you’ve had team members ask the same questions over and over, and it’s maybe the 10th time you spent explaining it, there’s probably a better way. SweetProcess is a software that makes it drop dead easy to train and onboard new staff. They help universities, banks, hospitals, but I was talking to Owen, the founder, and I didn’t realize that first responder government agencies actually use them in life or death situations to run their operations, which was cool. SweetProcess documents all the repetitive tasks that eat up your precious time so you can focus on growing your team. You could sign up for a 14-day trial, no credit card required. Sweet like candy. S-W-E-E-T

Dr. Jeremy Weisz: I am excited to introduce you to Bill Shepard. He’s founder and CEO at the Chief Operating Officer Business Forum, which is The COO Forum, what they do is they provide collaborative pure learning and meeting forums to chief operating officers and other second-in-command executives. Prior to… If you… Bill, I think of this. If I want someone behind me, it’s going to be you. You’ve had over 25 years as CEO and COO. You worked at CEO of NordicTrack, Philips Electronics, was a VP at Gap and so much more. So I appreciate you coming here to share your knowledge.

Bill Shepard: Thank you. Thank you, Jeremy. I’m delighted to be with you.

Dr. Jeremy Weisz: I figured we’d start with… Because you’ve worked at a CEO, COO, so I figured you would go over some of the winning ways, the top winning ways that COOs can create an amazing relationship with the CEOs.

Bill Shepard: Jeremy, that’s how I got into the COO Forum business. I just had so much passion for the chief operating officer, because I found that when I was one it was far more difficult than CEO or CRO or one of the other, even CFO, because every role is a little bit different and so much of what you’re responsible for, you have to work upwards, you have to work outwards and you have to work downward. The CEO is well-served. We have lots of places for them to get into professional development and so forth. There was very little to no professional development, and that’s what got us going. We have grown fairly modestly but well, and we are always looking to grow our chapters. We’re at about 45 chapters right now all over the country and we have meetings monthly.

Bill Shepard: Of course with this new era that we’re in, we converted all to Zoom so we’re doing virtual and our business is quite good still and we’re very delighted about that. One of the other things that I knew, because I had been a COO, was that the CEO was sometimes a very difficult person to work with. It wasn’t-

Dr. Jeremy Weisz: Because you were one of them or why?

Bill Shepard: Well, I was one of them but I might’ve been a little bit easier. The CEO has to answer to the board, has to answer to shareholders. You have a spectrum of things the CEO has to do that isn’t anything to do with helping the COO be great. Then the second thing is, is that so many CEOs have no idea what a COO does. I had a call from a director-level person from Seattle down and he wanted to know what a COO did because his boss had just become the new COO of the company. He wanted to know what we did at COO activity. By the way, that was Kevin Turner, who was the COO at Microsoft. So I figured-

Dr. Jeremy Weisz: Nice.

Bill Shepard: … if the Microsoft COO is still looking for what do we do, it’s very imaginable to believe that everybody has a little bit of that.

Dr. Jeremy Weisz: Everyone else. Yeah. Totally.

Bill Shepard: So I was one of those people just who was eventually known for I’d walk into an elevator and somebody would turn to me and say, “Oh, you’re the COO guy.” That was affirming that we were doing something right. But the COO-CEO relationship is a difficult relationship in most companies. Most of the time, in my opinion, it’s tied more to the idea that the CEO isn’t paying enough attention and the COO is always waiting for the CEO to tell them what to do. Neither of those things are good. I think that one of the winning ways that COOs can tackle the whole CEO thing is to start at the beginning of trust and chemistry. Find the trust. Find the chemistry. I-

Dr. Jeremy Weisz: How do you do that?

Bill Shepard: I strongly recommend you spend time by scheduling meetings. I hear COOs say, “Well, I just can’t get to my boss.” Schedule a meeting. The CEO is not going to schedule a meeting for you, but you can schedule it for them. Then you’ve got to drop the ego and the control stuff. I mean, if you have real high ego and high passion and high control, you are going to bump into that CEO regularly. Then of course you got to keep the two-in-a-box, is what they call it, but you’ve got to be two-in-a-box. You can’t gossip about the CEO and the CEO can’t gossip about you, but more importantly, you guys have to view yourselves as a team and then just keep the issues between the two of you.

Bill Shepard: There’s a topic called disagree and commit. I don’t know if everybody’s heard it, but I got it from Louis Selincourt who was a phenomenal COO, who was part of our early, early group. He was in the first round of COO people. He’s since retired and gone into consulting. Louis always said, “The key is to be in the room with a COO, with the door closed and be able to say, ‘I disagree with what you want to do, but I’m going to walk out that door and do everything you want to do well.'” The same thing applies that the CEO owes the COO the same kind of respect because at times the CEO will say, “Hey, I’m ambivalent to this. You run with it.” [inaudible 00:07:42] and say, “Look, I’m going to run this, but I need you on my back. I need you to be telling everybody what we’re doing is right.”

Bill Shepard: So there’s a lot of CEO things. I also have a recommendation to any of the COO’s listening is that there’s a Nate Bennett, Stephen Miles HBR, The COO and The CEO. I encourage new COOs to go take that document, sit down with your CEO and talk about it because it’s a fabulous… Talks about the seven or eight different kinds of COO’s. It talks about the kinds of CEOs. It talks about responsibilities and it’s also written by authors, one’s a professor and one’s a search guy. But it’s a very, very, very good [inaudible 00:08:41] for particularly emerging COOs. So that-

Dr. Jeremy Weisz: Yeah, I had a question. It’s like a marriage, right? I mean, it’s like if you have kids and you’re married, you have to go through as one team to the kids. You can’t just disagree in front of each other. They’ll smell blood in the water and they’ll just divide you, right?

Bill Shepard: Yes. Yeah. Yeah. Although as a former parent and as a grandparent today, I can tell you that it’s a lot easier to be a grandparent than it is to be a parent because you don’t have to do anything other than just smile and enjoy the kids. Yes, it has those dynamics. I think the difference is, is that you’re operating essentially the same. You’re driving the same thing. The CEO wants you to succeed. You want the CEO to succeed and all of us want the company to succeed. I think that it is a little bit more collaborative than being sometimes in spouse, because you wind up with different likes and different patterns and so forth.

Dr. Jeremy Weisz: You mentioned, Bill, setting a meeting with a CEO that will just keep increasing the trust, the communication, the chemistry. What are some of the things that you feel the COO should bring to a meeting when they’re scheduling with the CEO?

Bill Shepard: Yeah. I mentioned disagree and commit, but one of them is the EQ. The COO is the emotional quotient in the C-suite and the CEO is the driver so if you cannot maintain your EQ as you navigate through your company, you’re going to find that there is lots of trouble that you can’t get around, and you’re going to bounce into things that you don’t want to do. I think that’s one of the keys. I always say you want to act actively listen. You can’t be defensive. You got to be positive. In some respects, the CEO sometimes gets a little worked up and so forth so you’re also the adult in the room oftentimes, and that’s an important part of understanding that the COO has to own the COO and not delegate it to him or her.

Dr. Jeremy Weisz: So Bill, now that we talked about the trust and chemistry, what’s another winning way that a COO can create a great relationship with their CEO?

Bill Shepard: This is one that may be offensive to CEOs, but it’s one that I really believe in. You want to exploit the CEO’s ego. CEOs have big egos. They are generally very strong and strong-willed and exciting and dynamic. The one thing I learned as a CEO is that it’s also a very quiet place for feedback and recognition. One of the recommendations I make in my Winning Ways to Create a Wonderful Relationship with Your COO is to take the point of being the advocate of great work. When a CEO has a great company meeting and just delivers it, within the half hour after that, you’ve got to get to the CEO and just tell him what a great effort that was and what a terrific… Thank them. If you can keep the ego down a little bit by essentially rewarding and just reinforce your loyalty and respect and be very positive and enthusiastic about the CEO’s work and about the CEO’s ability to get great things done… So often at the C-suite in the CEO position, you hear nothing. Oh, you hear from the board.

Dr. Jeremy Weisz: You hear all the negative things.

Bill Shepard: You hear from the shareholders. You hear from the financial guy. You hear from people, but you don’t hear about the relationship with your own sense of how you’re doing. It’s a lonely job. CEO is a lonelier job than COO.

Dr. Jeremy Weisz: Yeah. Yeah. It’s expressing that appreciation, gratitude, and also just making sure that they know that they’re doing a great job because probably most of the time they hear negative things. What’s the next one?

Bill Shepard: The next one is to take control of your domain. Own the COO position in the company. I have a story, if I can be free to tell it.

Dr. Jeremy Weisz: Yes.

Bill Shepard: It’s a person who passed away, but there was a time in my earlier career that I was in Chicago running The Gap’s division in all of the Midwest. I was asked to go to Kentucky because we were being petitioned by the Teamsters for a union election, which we didn’t want to have. They sent me down there to run the show, so I was brought into on a temporary project. When we were doing the whole setup, Don Fisher, who was the CEO-owner of Gap, wanted to come out and say hello. When he came out, I knew Don. I’d worked with him for years in different situations.

Bill Shepard: He was always great with me yet at the same time, he was always a little bit quirky. I just had to take the quirks out of him and say, “Hey, we’re going to do this. I only need you to do two things. One, tell everybody it’s going to be better and smile, and don’t answer too many questions. Don’t get involved. Let me and the others do the work.” He went for it. There is something about taking control of your own domain. There are things the COO should do and should not let the CEO meddle with that.

Dr. Jeremy Weisz: That’s good.

Bill Shepard: Each company will be different based on how they orchestrate their work charts and so forth.

Dr. Jeremy Weisz: Yeah. Yeah. Yeah. If you didn’t do that, who knows what would have happened? You don’t give that specific direction, who knows what happens after that?

Bill Shepard: We won the election by 80/20.

Dr. Jeremy Weisz: Nice.

Bill Shepard: It worked, but it wasn’t… He was as important. His one day at the shop there, his one day of wandering around and being just a regular folk was wonderful. It was very positive.

Dr. Jeremy Weisz: Nice. So, take control. What’s the next one?

Bill Shepard: Oh, my next one’s sell and market yourself. I mentioned that you have to be great with the CEO, but the CEO isn’t paying attention to you. So it seems like somebody has to tell the COO story and the only person who can say, “Hey, so you’re my new CEO. Here’s what I’ve done and here’s how it’s working and whatever, whatever.” Sell and market yourself and your ideas is the topic, the way I see it. You have to be stelling upward all the time to keep your leadership team in tune with the idea that your work is coming through and you’re doing great work and remembering that the CEO doesn’t pay a lot of attention to a lot of things, because they’re tackling all those other things. You are the only one who probably will walk in and tell them about the great things you’re doing you and I recommend, make sure you’re on your game. You communicate the metrics. You update the progress. You’re just always thinking about making sure the CEO is not blindsided by anything you’re doing.

Dr. Jeremy Weisz: So always make sure you’re advocating for yourself, also?

Bill Shepard: Yes. Advocating for yourself, but also speaking to what you’re doing and why you’re doing it and how is it working. It’s that sense that the CEO can then drive home at night and say, “I heard from my COO. I know what he’s doing. I like what he’s doing.” Or, “I’m going to come back tomorrow and I’m going to talk to him about this, this and this. We’re going to get that straightened out.” Whatever it is. It could be something like that, but it has to be… The COO oftentimes is afraid of the CEO and tends to avoid the CEO. That is the thing you can’t do.

Dr. Jeremy Weisz: What’s another winning way?

Bill Shepard: Oh, okay. Yeah, this is fun. I just want to let you know. I’m having a great time.

Dr. Jeremy Weisz: Good. Me too.

Bill Shepard: Admit your mistakes.

Dr. Jeremy Weisz: By the way, I would love your stories. So yeah, you can be as long-winded as you want, Bill.

Bill Shepard: All right. Fine.

Dr. Jeremy Weisz: [crosstalk 00:18:17] can talk.

Bill Shepard: Unfortunately, I could probably tell stories for a long, long time. Anyway, admit your mistakes and ask for guidance and support. There is not an executive in the universe that hasn’t made something go wrong. I think things go wrong. Stuff happens so I think that the minute you see that something is not right and you’re a part of that whole thing, you have to get to the CEO and say, “Hey, we thought we were going this way. This is what were happening, but now we’re seeing it this way and we’re in trouble and we’re going to have to reboot.” So when you think about how that would work, you are really keeping the CEO on target from the COO’s information and point of view.

Bill Shepard: That’s really, really important because then the CEO knows, “Oh, he doesn’t hide things from me.” Hiding things from the CEO as a COO is also poison. That’s a real troubling area. Then if it works, you can get the CEO engaged with you and to help you figure out how to get out of it. I think there’s some dynamics there. Some CEOs are more difficult than others, but you want to be paying attention because you got to disclose it and then you’ve got to clean it up or fix it or change it or whatever you guys decide to do.

Dr. Jeremy Weisz: What it makes me think of, Bill, is that’s not an easy thing to do. Out of these so far, or in general, what do you find is the most challenging for the COO? Sometimes admitting your mistakes is, well, it’s sometimes easier said than done or any of these things are sometimes easier said than done. What do you find is the most challenging for the COO?

Bill Shepard: I think the hardest challenge is adjusting to the CEO as the CEO moves around a lot. That’s one of them. The other one is, is that not every CEO wants to hear your stories of about what you did wrong and will blow up on you and do maybe some bad behavior, things like that that happen. So the concept, I think, that I see is that we want to advocate good quality relationships. That’s where are we right now, is where we need to be is in a quality relationship. The thing about it is if it really isn’t working, it’s time to get out as a COO. That’s another, I guess, statement around this, is that there are times when you just can find that wonderful magic with you and your CEO and you know that you’re right and you know that the company is hurting because of it and the CEO isn’t helping and things like that. It’s probably smart to get to somewhere else, land at a new place.

Dr. Jeremy Weisz: So after admit your mistakes, what would it be another one?

Bill Shepard: All right. This is one that always mystifies people around my table because I say you should work like you own all the shares. Instead of thinking about yourself and thinking about all the linear things that go on in a business world, you really want to know what the perfect CEO-COO relationship should be, and you want to be working towards that. It doesn’t matter what your position is. You want to bring out the best in everyone. You want to deliver. You want to take care of ownership and board. You want to really be an every man. You want to be all things to all people and working very, very, very tightly with everybody. If you work like you own all the shares, that’s… The thinking matter here is, “Wait a second. If you owned everything, the first thing you’d want is a COO that looks like you, who does take care of everything and takes care of it well, and at the same time supports the CEO, supports the teams, supports the customers, supports the stockholders and the board and so forth.”

Dr. Jeremy Weisz: Nice. Yeah. I mean, that’s great advice to live by for anyone, right?

Bill Shepard: Yes.

Dr. Jeremy Weisz: Everyone should work like you own the company. If you work like you’re an owner, it’s just, you get respected.

Bill Shepard: Yes.

Dr. Jeremy Weisz: Right?

Bill Shepard: What is-

Dr. Jeremy Weisz: Yeah.

Bill Shepard: Go ahead. I’m sorry.

Dr. Jeremy Weisz: No, go ahead.

Bill Shepard: I was going to say, I also trademark that, by the way, I just thought I’d let you know that. Someday later in life, I may write a book. If I write a book, it may be around this whole idea of how to make it better in the workplace as COOs and CEOs.

Dr. Jeremy Weisz: What would your book title be? The trademark term or-

Bill Shepard: Yeah. Work like you own all the shares. I don’t know, I just like it.

Dr. Jeremy Weisz: I like it, too.

Bill Shepard: Everybody has their own likes and dislikes.

Dr. Jeremy Weisz: Well, I think it’s words to live by for most anyone, you know what I mean? Whether you’re a COO or doing any job. If you’re mopping the floors, same premise applies, I think. What’s the next one?

Bill Shepard: Well actually, the next one is really a pivot to today’s and the ups and downs. We have been, as the Chief Operating Officer Business Forum, we’ve been doing this for 16 plus years and we have seen the ups and downs. We have seen 9/11. We’ve seen the Great Recession. We’ve seen this awful pandemic and so forth. So one of the things is, is that I think that being a COO in difficult and unusual times adds to the dimension and difficulty of the role. In some cases, you really aren’t sure if what you’re doing is right or wrong, because you can only see what you can see. We don’t know the outcome. So we’re spending a lot of time at the COO Forum on round tables around the topics of what is going to change after this pandemic. During the Great Recession, we of course had a tremendous amount of stock market loss and things like that.

Bill Shepard: So we were very focused at that point on also getting people back to work. We have launched, this month, we have launched the COOs in Transition, which is a sidebar of our COO Forum that enables us to help COOs who are going to be furloughed or laid off and/or who are already furloughed or laid off to find the next opportunity, hopefully as a COO, but maybe in some other positions. So all these things we’ve talked about are absolutely wonderful and great, but the other thing is, is we’re in such unusual times, and it’s also amazing to me around our Zoom calls, how many companies are doing very well, very, very well, and how many companies are doing very poorly and very, very poorly. So we have also this situation where, when we gather and talk, not everybody is able to talk at the same plane because each company is facing different issues and uncertainties and concerns.

Dr. Jeremy Weisz: Bill, first of all, I want to thank you. I have one last question, but I just want to thank you for sharing your expertise. You’ve been in the trenches for so long, so your advice is really valuable. I want to encourage everyone to go to and check out everything that you’re doing over there. The last question is just any final advice, any final advice for COO’s or COOs and CEOs from your wisdom?

Bill Shepard: Yeah. I would say that for COOs, this is a wonderful position and it’s also a wonderful position to launch yourself into CEO. It’s a wonderful time because business is changing, new demands are going to be made on all sorts of dimensions. I would say for COO’s, this is a really good time to be a COO and to stay as a COO. From the CEOs perspective, I think it’s even more challenging and so forth. But I like to talk, the COOs oftentimes don’t ever want to be a CEO and some of them want to be a CEO the next minute. They’re really ready to go. There’s also a relationship of people who were like me, who were both CEOs and CEOs. There are a lot of people who are COOs that just don’t have a reason to be anything but a COO and don’t want to be the CEO, don’t want the pressure, don’t want the politics or the board or any of that other thing. So that’s another dimension of this.

Dr. Jeremy Weisz: You were CEO first and then went from CEO to COO?

Bill Shepard: Well, eclectic and size of companies. I was a zero to Vice President at Gap in over an eight year period, and then founded a business with my wife and we had a small business of paper stores all over the Midwest, and that was a small operation. Then I went on to Call National, and that was a conglomerate and I was a divisional president. Then I went on to Phillips and I was the president and COO. I had a CEO boss who was just a financial guy, so I was the head person in that company. Then I went to Pacific Linen as a CEO.

Bill Shepard: But I also, after that, I did COO work in Cleveland. I worked for a company called Our House Furniture as the COO. We grew the business very nicely. It was a very nice run. Then I went to NordicTrack where we were mostly moving it from the portfolio, so I was not the ultimate driver of that business. I was the ultimate let’s wrap it up and figure out what we’re going to do with it. I was on the board of CML. That was what… I don’t know if you know CML? Do you know CML?

Dr. Jeremy Weisz: No.

Bill Shepard: Anyway, they had Smith & Hawken, NordicTrack, Her Music and some other properties.

Dr. Jeremy Weisz: Nice.

Bill Shepard: It was based in Boston. I was the designated retailer on the on the board. They asked me to go out to Minnesota and figure out what we’re going to do with this property. So that was what I did. So I also have some eclectic things that I have done, business-

Dr. Jeremy Weisz: Yeah. Sounds like a tough job.

Bill Shepard: Well, it was the way the board wanted to run. The board was in power and owned the company. It was what they wanted me to do. I was a loyal Lieutenant to what they wanted done, because I was a board member with them so I was also part of it. But it needed to be sold. We did. We sold it to ICON Health & Fitness and Sears. They wound up in Utah, where ICON Health & Fitness was, where they settled for their headquarters. I was invited to join and I said no. I have nothing against Utah or Logan, Utah, but I just didn’t think that I… I thought I’d be better off going into consulting and that’s when I did the pivot to consulting.

Dr. Jeremy Weisz: Nice. Well, Bill, I appreciate you sharing all of your knowledge, stories. Everyone check out Check it out and thanks again, Bill. Appreciate it.

Bill Shepard: Hey, thank you. Enjoyed the time and always love to talk about my world. Thank you. Thanks for having me.

Speaker 1: Thanks for listening to the Process Breakdown Podcast. Before you go, quick question. Do you want a tool that makes it easy to document processes, procedures, and/or policies for your company so that your employees have all the information they need to be successful at their job? If yes, sign up for a free 14-day trial of SweetProcess. No credit card is required to sign up. Go to, sweet like candy and process like Go now to and sign up for your risk-free 14-day trial.

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