Recognizing When Your CEO Isn't Scaling with Cristina Miller

Intro: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg. I'm the founder and CEO of Bolster, and I'm excited to be here today with Cristina Miller. Cristina is the Chief Operating Officer of GoldBelly, the food e- commerce marketplace, and before that was Chief Commercial Officer at First Dibs, which is an antique marketplace. She has lots of great experience in and around e- commerce and marketplaces. She's also a member of our Board of Directors here at Bolster. Welcome to the Daily Bolster, Cristina.

Cristina Miller: Thanks, Matt. Great to be here.

Matt Blumberg: So our topic today is how do you know if your CEO isn't scaling and what do you do about it? So at Bolster, obviously we spend a lot of time working with founders and CEOs on whether their teams are scaling and how to scale their board, helping them find coaches and mentors so they can scale themselves up. But as a CXO, what are some signs that your boss might not be scaling?

Cristina Miller: Yeah. Well, I think that it's something that can happen, particularly when businesses are scaling quickly, and CEOs, as you said, certainly need to think about if their management team is scaling. And I think the management team should think about if their CEO is scaling and if their counterparts are scaling. I actually think it's healthy for the business. It shouldn't be taboo. It might be. It might not be the easiest thing to talk about. We'll probably talk about that. But I do think it's something people should be aware of. And I think some of the signs are around, well, this is actually stolen, I think from you, Matt, this sort of french fry model where you can always eat another french fry. I certainly can. Apparently you can too. You've probably seen me do it. But I think if you find that the CEO is doing that, and what that means is they're just sort of taking on more and more and more kind of detailed tasks. This is a pretty standard one around scaling. If they're sort of playing it at too close a level to the ground, that's one sign. There's another thing that I've seen though, where I think everybody has their strengths and weaknesses and everybody is drawn to certain things. People are often drawn to the things where they can exhibit their strengths. And when you see that, a CEO, or frankly anyone on the management team, is sort of only working on those things and perhaps working at the French fry level. So just one more thing in that area, those to me are two warning signs that you might want to kind of pay attention to that a little bit or investigate or think about what you should do.

Matt Blumberg: So yeah, that is really interesting. And they're probably other ones too, but those are two really good ones. So the second half of the topic is, okay, so what do you do about it? Right? Are you're a senior executive, you're working at a company, you're concerned that your CEO is not keeping pace with the growth of the business in terms of his or her own growth. What do you do about that?

Cristina Miller: Yeah.

Matt Blumberg: You talk to the board? Do you talk to your peers? Do you talk to the CEO directly? Is there a coach involved? How do you think about it?

Cristina Miller: Yeah. Well, I would say, first of all, I would ask myself if it were me, is the CEO doing the things that only the CEO can do? And that's sort of an umbrella check, kind of on what you said, I think there probably are other signs. But I always like to think about in any role, I think whoever is in that role should be doing the things that only they can do for the most part, particularly as you move up. And if you're doing something, I judge myself on this. If I'm doing something that someone else on my team can do, maybe I shouldn't be doing it. If the CEO is doing something that someone on their team can do or on their team's team, which when they're playing down a couple levels, then that probably is something that I would say the person on the management team, the CXO, would want to talk with a trusted confidant about. For me, I would probably talk to someone outside the company, a mentor, I might call you up, particularly with your expertise in this area and some books that you've written. But I do think it's worth bouncing it off of someone else first because everyone's biased. And I've certainly had situations where I've actually ended up learning. I might have thought that I was in a situation where CEO wasn't scaling or I was worried about how they were spending their time. And I actually learned that it was not only okay, but that there was a reason for it. And I was able to, the management team I should say, was able to sort of adapt and adjust.

Matt Blumberg: And have you ever raised something like that directly with a CEO or with someone on a board or?

Cristina Miller: Yeah, yeah. Actually I have raised twice with two different CEOs. I've raised some concerns now. I think maybe this falls in the advice category, but I probably wouldn't go say, and I didn't, " Hey, I think you're not scaling" or" You're not doing a good job." But I do think that it's important to be honest, be direct voice a concern in a constructive way. We all know be constructive. " Hey, I was thinking, I know you're attending quite a lot of vendor meetings" or whatever it is. But I wouldn't say, I wonder if that, I would be pretty direct, sort of" Is that really the best use of your time? Because we love having you there, but it makes me a little worried that we have 20% of our executive team talent or 50% or whatever it is in every vendor meeting. And maybe we should be rethinking this."

Matt Blumberg: I guess you could always take the inquiry approach also of, " Hey, just curious, how come you're in this? Is there something I'm doing as the executive in charge that you're concerned about?"

Cristina Miller: Yes. Yeah. And actually what I have had, I have done that approach, and in that case, that approach was less helpful because what I found was that person then reassured me, " No, no, no, you're doing everything fine. It's great." And then you're stuck. I agree with that approach and I think it's worth trying, but you might then find yourself in a place where you still have to say, " Oh, okay. Well, then why are you joining us?"

Matt Blumberg: Right. Why are you in there?

Cristina Miller: So maybe I love the inquiry approach. Maybe it works, maybe it doesn't. I would say just be ready to say, " Gosh, do you think that the business would benefit from you doing something else with your time?" And I have had a conversation like that once and it was really a relief to the person because they said, " Oh, do you think I can free up my time to? Yes, I can do that. Great. I will go do something else." So I have had some good outcomes to a conversation like that once or twice.

Matt Blumberg: Have you ever felt like the situation was serious enough that you had to go to the board?

Cristina Miller: Oh, right. No. I'm trying to think of what... I did go to a board once, but it was about a fellow management team member. And it was with, this was a few companies ago. It was with the blessing of the CEO, which I think is important. But I actually think if, if can't get the blessing of the CEO because the CEO is the person you might be concerned about. I think that is one where for sure I would go to a mentor or two and run that by them. And then I think, I imagine boards have seen it all. And I think the most important thing is any action should be very clearly couched in this is because I care a lot about the business and I care a lot about my relationship with this person and with you. And I just want to raise some concerns.

Matt Blumberg: And that is a great note to end on. The business is always the boss. Thank you, Christina, for being with us today.

Cristina Miller: Thanks for having me, Matt.