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The Operations Room: A Podcast for COO’s artwork

88. Discovering Your Strengths

The Operations Room: A Podcast for COO’s · 2026-01-22 · 52 min

0:00--:--

Key moments - from our scoring

Substance score

50 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality9 / 20
Guest Caliber12 / 20
Specificity & Evidence8 / 20
Conversational Craft10 / 20

This episode tackles the psychological and physical toll of sprinting marathons in executive roles, grounded in Brandon and Bethany's personal reflections on aging, joint pain, and accumulated burnout across their careers. Alicia Diamond, former CEO of Long-Term Stock Exchange, shares her decision to step away from the linear career path after recognizing she'd lost perspective, deprioritized health, and plateaued on her learning curve. The hosts and guest explore how COOs can apply frameworks like EOS and OKRs intelligently - borrowing useful elements rather than implementing them rigidly. A key insight emerges around SMB owners' allergic reaction to accountability-heavy frameworks; the solution is bespoke application. Alicia discusses her fractional CEO model paired with a chief of staff and admin support, bringing tech startup operational intensity to smaller businesses. The conversation also covers quarterly personal reflection (ideally with a business coach), the importance of unstructured leadership conversations, and how Brandon's current company is rewriting the growth playbook by targeting $100M revenue with only 50 people using AI - rejecting the traditional SaaS scaling model. The episode resonates with operators seeking alternatives to burnout-inducing sprint cycles and one-size-fits-all operating systems.

Key takeaways

  • →COOs underestimate how much they sprint marathons despite saying it's a marathon not a sprint, leading to accumulated burnout that only becomes visible after leaving a role - consider structuring 18-month to 2-year breaks between positions to properly recharge.
  • →Frameworks like EOS and OKRs are tools, not dogma; SMB owners specifically resist prescriptive implementations because they started companies to escape rigid accountability structures, so apply frameworks bespokely and abandon them mid-quarter if they stop making sense.
  • →Quarterly check-ins with a business coach create a forcing function for personal reflection and seasonal retro that most executives skip without external accountability - invest in this practice to gain perspective on career trajectory and life priorities.
  • →The fractional CEO plus chief of staff plus admin support model represents an emerging operating structure that brings tech startup operational intensity to smaller businesses without full-time overhead.
  • →Different executives have fundamentally different operating rhythms - some thrive on consistency and pacing (like Brandon's three gym sessions weekly regardless of circumstances), while others burn bright and crash; understand your natural pattern rather than forcing yourself into incompatible modes.

In this episode

  1. 1Personal Health and Aging Reflections
  2. 2Office Culture and Impromptu Leadership Meetings
  3. 3Discovering Your Strengths with Alicia Diamond
  4. 4Burnout, Sprinting Marathons, and Personal Pacing
  5. 5Frameworks, EOS, and Avoiding Rigid Implementation
  6. 6OKRs and Flexible Goal-Setting Approaches
  7. 7Fractional Leadership Teams and Operating Models

Mentioned

Brandon MencingaBethany AyersAlicia DiamondLong-Term Stock ExchangeMatomicEOSOKRsMatthew StonePete Crosby

Guests

Alicia Diamond

Topics in this episode

OKRs (Objectives and Key Results)EOS (Entrepreneurial Operating System)Long-Term Stock ExchangeChief of Staff roleFractional CEO modelBusiness coach quarterly check-insSMB operating modelsAI-driven scalingSaaS scaling playbooksPersonal burnout and recovery

Questions this episode answers

What made Alicia Diamond step off the traditional CEO ladder?

She was tired from sprinting marathons for years, had lost perspective and deprioritized health, and realized she was no longer on a steep enough learning curve - she had run the same marathon course repeatedly and craved change and reset.

Why are SMB owners allergic to EOS even though they know about it?

They started their own businesses specifically to escape rigid accountability environments, so they resist frameworks imposed by-the-book; they need bespoke applications that borrow useful elements rather than full implementations.

How should companies implement OKRs without wasting time on measurement setup?

Use directionally accurate measurements that are readily available rather than spending Q1 building perfect measurement systems; abandon KRs that stop making sense mid-quarter and iterate on initiatives like a puzzle rather than treating them as fixed.

What does the fractional CEO plus team model look like?

A strategic fractional CEO, a whip-smart chief of staff, and admin support work as a tag team deployed into organizations; this brings tech startup operational intensity to SMBs and spreads business development risk across a network of operators.

How can executives recover from burnout without just taking a two-week holiday?

Extended breaks of 18 months to two years between roles allow proper gearing down; two-week holidays don't work because high-velocity minds stay geared toward scheduling and movement, requiring sustained time to shift into a genuinely relaxed state.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

11 / 20

The episode contains some practical advice about career transitions, frameworks for SMB operations, and personal reflection (quarterly check-ins, finding a personal board of directors), but much of the first 20+ minutes is filler - lengthy personal discussion about hand pain, aging anxieties, and office dynamics that add little actionable value. The guest segment offers moderate insight on fractional COO models and framework customization, but lacks depth on implementation or specifics.

we end up sprinting marathons. And you can do amazing work that way. And I guess I'll just speak for my own experience because that's the only one I know, but you can begin to lose yourself
So they're getting some strategic COO with me, they're getting some execution support from a whip smart chief of staff type person coming out of tech. We bring in some admin support as well, but to bring that intensity of operations that I think a lot of us grew up with in the tech world, bringing that over into SMB where it is sorely needed

Originality

9 / 20

The guest's fractional team model is a modest variation on existing fractional consulting and revenue coaching models (Pete Crosby example mentioned in transcript). The frameworks discussed - EOS, OKRs, business model canvas - are well-worn. The career pivot narrative, while personally authentic, follows a recognizable pattern (burnout → soul-searching → new path). Limited contrarian or first-principles thinking.

I'm bringing the tech startup intensity of operations into SMB where it's sorely needed
what I found that resonates is the ability to take a little bit from multiple frameworks and customize it to what they need

Guest Caliber

12 / 20

Alicia Diamond is a former CEO of Long-Term Stock Exchange (founded by Eric Ries, Lean Startup author) and has operating experience in FinTech at scale. However, she is now working fractionally with SMBs rather than leading at scale, which somewhat limits her credibility for a COO audience seeking high-growth operational expertise. She is a practitioner but not an exceptional caliber guest relative to the show's positioning.

I was at a series C FinTech company
I was fortunate working at Long Term Stock Exchange. It was founded by Eric Rees, who wrote The Lean Startup

Specificity & Evidence

8 / 20

The episode is sparse on concrete examples, metrics, and named companies. The guest mentions Long-Term Stock Exchange and references Eric Ries, but provides no specific case studies, numbers, or measurable outcomes from her fractional work. The hosts mention Pete Crosby as an analogy but don't dig into details. Most claims remain abstract or hypothetical.

they're getting some strategic COO with me, they're getting some execution support from a whip smart chief of staff type person
call it like three million in revenue up to about 50 million in Revenue private so it's the owner as the operator

Conversational Craft

10 / 20

The hosts (Brandon and Bethany) demonstrate some self-awareness and reflection, but their questions to the guest are often soft and rhetorical rather than genuinely probing. They ask follow-ups but rarely push back or challenge claims. The early 20 minutes of personal banter on hand pain and aging show poor editorial discipline. When substantive questions arise (e.g., on scarcity vs. abundance), the guest is allowed to deliver lengthy, uninterrupted monologues without tight follow-up.

First question to you, Bethany, what resonated most with you from Alicia's decision to get off the ladder?
So where I am today is...An opportunity to operate as fractional COO SMB

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

team19started14feel14sense14idea13back13terms12different12frameworks12love12conversation11career11interesting10three10alicia10fractional10

Episode notes

In this episode we discuss: Discovering Your Strengths and Living The Life That You Want. We are joined by Alicia Diamond, COO and Transformation Leader. Love The Operations Room? Please support us by rating and reviewing it here . We chat about the following with Alicia Diamond: What happens when you stop waiting for “perfect clarity” and start sharing half-formed ideas with your team? How much operational value is lost because your best thinking happens outside formal meetings? Are your leadership decisions driven by energy and context - or by calendar availability? What if the real bottleneck in your organisation isn’t process, but permission to think out loud? How do you create space for strategic thinking when the operational noise never really stops? References Biography Alicia has been the right-hand, “figure it out” partner to 5 CEOs as a 2x COO and 2x Chief of Staff. She's helped visionary CEOs across diverse industries to get their most transformative ideas unstuck and into action.

Full transcript

52 min

Transcribed and scored by The B2B Podcast Index.

Hello everyone and welcome to another episode of the Operations Room, a podcast for COOs. I am Brandon Mencinga joined by my amazing co-host Bethany Ayers. How are things going, Bethany? As I'm asking this question, I'm trying to prop myself up with energy and I'm sure you are too.

I really am. I'm just, I'm tired. I need a holiday. And for whatever reason, my hand has started to hurt.

Your hand. Hahaha. My right hand is just really sore. Why is that?

To which signature writing or what's happening? Yeah, all those deals I'm signing, and I have no idea. It's just, am I using my phone too much? Am I developing arthritis?

Or am I sleeping on it strangely? I have no idea, but it's just sore, the whole thing. And it's putting me in a bit of a bad mood because it just hurts. Not unbearable pain, like maybe four, but just all the time.

Do you think it's stress-related somehow, it's a manifestation of your inner being? Everything is stress-related, but maybe it's kind of been going on and off for a few weeks, but all of my joints are also a bit more sore than they used to be. So now I'm thinking, do I need to take collagen? What's the thing for joints?

Yeah, yeah, I think it's joint related because like I mentioned before, I have a similar joint. It's not joint. It's my lower back. It's such a traditional old person thing, isn't it?

Oh, my lower-back. But legit, and not because I'm old per se, but I think just combined with the workouts and the deadlifts and the squats and all that, I thing my body is telling me something useful that I should pay attention to. My birthday is next week, so definitely aging and death is sitting on me. And then- Are you turning 50, by the way?

No. Yeah. No. What?

More year. Late 40s. Okay. Yeah, one more year to go.

But yeah, closing in on, again, next week we'll be closing in on my 50th year, which is just a strange because on the inside I don't feel that way, but yet on the outside. And then also dealing with, like I was thinking about this, like when I was at peak, where the bulk of the people were just either side of 30, like kind of marriages happening, babies happening, and I was 40. And so like a 10-year difference, it all felt okay. Now at Matomic, everybody is either side of 30, again, because that's what attracts startups.

But now I'm approaching 50. And so it's like a 20-year difference between me and everybody, rather than a 10-year difference. And it's just a lot. It's interesting because just as an aside, we have our Christmas party coming up at the end of this year.

We're going to some restaurant, as you'd expect, and there's two karaoke rooms afterwards for, I think at 9 p.m., 10 p. M.

, something like that. So then I was thinking about my usual genre of stuff that I would typically do for karaoke. Are any of these songs relevant anymore in terms of people actually knowing them at all? And they will definitely date me as being super old.

And then I'm thinking to myself, well, Should I just not do the karaoke now? Like, is it not going to be cool? Am I just, I don't know. I'm doubting myself.

Yeah, well, because our music are now oldies, you know, and so they'll know them, but they'll be like, Oh, yeah, classic. So it is, I'm just kind of coming to terms with like, normally I'm coming to terms with mortality, but this time I'm coming to term with becoming a fuddy duddy. And like, I never thought that would be me, but then I look at like women who are older than me, who are still really cool, and they're like, you can choose. I think so too.

There is a physicality that I can definitely feel now that I did not feel before and it makes me feel old. So I think it impacts my mindset and psyche to some extent in a not positive way. You know, and I, as you know, I'm a gym person. I work out all the time.

I'm in great shape generally speaking, but just the aches and pains that are associated to what's happening now, I just feel, it just makes me feel old and how you counterbalance that in terms of your mindset, I don't know, but I'm right in the midst of it right now. So I am too, because this started with my sore hand, but I've also been doing this dance class and it is clearly not good for my right knee. Not good enough to go to the doctor over, particularly because the appointments with doctors or physios are always very underwhelming.

But my right knee is not in a good place. And so when I stand up, I kind of have to let it warm up a little bit or half limp to get the pain out. And again, these are just these things. I like trying to style out the sore knee before I can take the next step when I'd stand up from my desk.

So what else is happening in the world of Bethany? I'm definitely settling more into the role, have learned a lot, understand the technology, starting to understand the placement of us in the world. But yesterday, yesterday for the first time ever, we actually filled up all of the desks in our office because we had two people who were working remote in and nobody was on, oh no, actually one person was on holiday. Ooh, so we would have maybe been one desk short.

But there's always multiple people on holiday, or out ill, or you're working remote, so we've never filled up the whole desk, all the desks. So it was quite nice. It was like, oh, look, it's a real company with a bit of a vibe, but it was busy day, lots of meetings, even an enforced meeting. And then I was talking to somebody in the kitchen area, like while people are leaving and had one more person come and join us, and we ended up having a really good and go-to-market and general strategy meeting, totally impromptu, to other members of the leadership team.

And it was just a massively valuable hour and a half. And I was like, why did that have to happen between six and half seven and not earlier in the day? And they were actually the people I was in another meeting with for two hours. And that meeting wasn't nearly as good.

And as just like, sometimes you need no agenda and just impromptic conversation and really good things happen. So I was trying to think like, how can we do it where it doesn't have to be after hours? Yeah, you know what's interesting? So I think I mentioned this some time back, but my previous company, Trent, the C-suite team, there's three of us and then four of us, every, was that every week or every other week, we would have a breakfast meetup with Jeff, the CEO, and we would sit there with no agenda.

And this was very specific and explicit on our part to do this outside of the leadership meetings. Sit there, have our breakfast, and whatever riffing that we were doing was purely organic and just to really do what you just said, which is just talk through our thoughts. Sometimes your thoughts are half-formed, and that's actually a good thing because if you put it out there as a half-form thought, where something is tweaked in your mind, somebody can pick up on that, build off of it, riff off of that, and by the time you finish that breakfast, you've actually produced something useful for the company.

We're like, oh yeah, this strand that we just identified makes tremendous sense and therefore we should actually do something. So now I'm thinking, can I fit in a breakfast or how do we do it? One member of the team is remote, which kind of makes it a bit more difficult. But I do think it's important to have that free thought time, particularly when you're handling thorny questions and not everything is.

Yeah, it's a bit like what you said before around OKRs where sometimes your objective as you lay it out all seems very linear and you know exactly what, how to get there and for the most part in OKR you have no idea how to go there and it's very much a puzzle. We have got a great topic for today, which is discovering your strengths and living the life that you want. We have an amazing guest for this, which is Alicia Diamond, the former CEO of Long-Term Stock Exchange. First question to you, Bethany, what resonated most with you from Alicia's decision to get off the ladder?

It's interesting because we're talking about this linear versus curved path and puzzle. It's like you're on a linear path of a career and you have to go to the next step of it. But you don't have to. You can change what you do and how you lead your life and decide that actually this bit of your career is over and it's time to go explore something else.

And it's just a real privilege to be able to do that and have that freedom. But I think oftentimes in a scale up, the journey tells you when in some respects, like either it's force because the company's acquired or some major event occurs or you're being laid off, obviously, that type of thing. But equally with the ebbs and flows of scale ups, you can get a sense of the journey coming to a close. And it's been a little spidey senses that start tingling where you're like, okay, I think I've done my piece here and it's time to look at something else.

And I find that a rather organic process. The other thing that I was just thinking about was the quarterly check in with yourself. And I was having an epiphany slightly in the sense that previously when I used my, with Matthew Stone, my business coach, I would meet him in the latter days on a quarterly basis. When I think about it, what that was, was a retro on where I was at with the company, with myself, a bit of a personal reflection.

And Matthew on a corny basis would help me think that through. And I feel like for any senior executive, that forcing function of having a business coach. That's mapped into your calendar to have a chat with that person about what is going on in your life seems very useful because I think for the most part, most of us don't do this. We're like, yeah, I should do some retro with myself, some personal reflection, and you never do it, right?

But if you have a business coach sitting there waiting for you at 1 p.m. On Thursday calendarized, you're like all right, I'm obviously going to that because I'm paying him 600 pounds for this session. Yeah, that's a really good idea.

I don't do it. So I'm always kind of like reactive to what's going on and what happens rather than actually planning a retro or like a bit of time to reflect on a season. Kind of like that idea. And also pulling it into the season seems appropriate.

Next question. Do you think COOs underestimate the cost of sprinting marathons? And the quote from Alicia was, as much as we say to ourselves it's a marathon and not a sprint, we end up sprinting Marathons. You can begin to lose yourself and lose your perspective.

I do feel like I've gotten better at this each time. And then while I'm in it, I'm like, yeah, yeah I'm fine. I know I'm conserving energy, I have boundaries. And yet at the end of every role, I am totally burnt out and don't realize it.

I mean, I shouldn't, I probably one of these people who's misusing burnout in that I'm curled up on the floor with adrenal collapse but After leaving a job, I never go from one job to another. I always end up with a 18 month to two year break between jobs while I go and explore other things. But the first month or two of that process is a lot of time with me just properly relaxing and recharging. So I suspect I'm probably sprinting more than I think at the time.

I mean, that seems like your personality. But equally, if you're taking extended breaks in between at this stage in your life, then maybe that's reasonable. I don't quite know. I mean I always find that when you take extended periods to recharge, you kind of need it.

When you take a holiday for two weeks or three weeks, I find that does not recharge me very specifically. Like I need time to gear down because I can feel my body. I wake up in the morning on a holiday on day two or something and I'm like raring to go? What's the schedule?

What are we doing today? My mind is geared towards like velocity and movement. And it takes me a while to like stop doing that to the point where I wake up in the morning, like, I'm just gonna go for breakfast, no plans, you know, it's golden. You also have young children.

So I don't think with a young family, any holiday is actually relaxing. That is a very good point. You know, I had another sort of revelation. I hate both ideas, and I don't think I do either, to be honest, which is I don't sprint and I do not do marathons.

I'm very consistent. My whole personality is geared towards consistency, reliability, step-by-step balance, as it were. I kind of revolt if people are asking me to work in ways that are unnatural for myself, whether it's to work, usually it's work faster obviously, but equally I hate the sense of moving slowly as well. Just the analogy in my head, I go to the gym three days a week and I do it religiously regardless of anything, so whether I'm not feeling well, I'm into it.

Work is bananas, whatever, or there's family issues or what have you. I'm always there, always doing it with a consistent level of zeal and energy that goes into it. So even if I start that session not feeling the greatest, I eventually will kick into gear at some point during that session and it will be usually a great session by the end of it. So that kind of consistency and pacing and drive, I guess, I apply that to the workplace as well.

I don't get burnt out per se. Because i feel like day to day week to week i'm kind of just pacing myself according to what works for brandon if that makes sense. Again, it's just so interesting how different we are in so many different ways. I throw myself into everything, learn everything.

I can't think of the locomotive in just 100 miles an hour, and then I stop. But for me, when I was younger, that pressure was wanting to succeed, wanting to do a good job. Being the best. And I think there's a lot of outside pressure, whereas now it comes from just like an insatiable curiosity and internal drive.

And so maybe that's why I don't perceive it as much as sprinting. Somehow I think of the sprinting as somehow being forced to do it, whereas I'm not forced to it from the outside. I'm compelled to do from the inside, but it still is exhausting. And, I do it with everything.

I don't just do it with work, like. Anything that I decide I'm interested in. I go very, very deep, learn a huge amount, and then I'm done. The third thing that she talked about was talking about SMB owners being allergic to EOS, and what does that say about COs need to show up?

And the quote from her in this case was, the SMB owner are familiar with EOS but they're allergic to accountability. They say, I started my own business because I don't want to be in that kind of environment. So I borrow from multiple frameworks and try to make it as bespoke as possible in respect to Alicia working with these individuals to help them understand that frameworks Arrrrrrrr. Not to be all and all but they're meant to be a tool by which you can actually apply to the company useful ways that the owner appreciates and can kind of get behind when you make about.

I love that. I mean, you know me, I'm not a fan of a framework and I'm really not a fan of an indiscriminately applied framework. And I feel like there's too much of that. You have execs who come with their playbook and they roll out the exact same playbook everywhere they go.

You have people who just are like, oh, Netflix did it that way, so we should do it that and we should follow it religiously or EOS makes sense, So let's just roll it out and we have no ability to take the good bit. Whereas I much prefer figuring out which parts of different frameworks and ways of approaching things exist and apply to this situation because no two businesses are the same, no set of people are the same and some things work and some don't. I used to think I just hated all frameworks and when somebody would talk about a framework and have a reaction to it, but now I realize I don't hate all frameworks, I just hate stupidly applied frameworks.

That is the literal distinction, I think. So I had a fascinating conversation with somebody in my current company around the next step for the organization, which is we're eminent in getting funding for the company, which means we're going to grow. And the way in which we galvanize the company to activate itself against the priorities of the business invokes what you just said, which is, what is our company's strategy? And then how do we activate in terms of applying OKRs in a way that is sensible for the organization?

And the conversation I was having with him was literally this, which is, you know, he's had experiences like we've all had where OKRs were implemented by the rule book effectively, and it was an absolute disaster. And I was heavily in the conversation talking about this in a way of like, yeah, I know what you're saying. I've lived literally everything that you've just described. And let me give you some of my stories to reflect back on your of course.

So this idea that sometimes when you set a KR, in particular for a product team, the KR literally cannot be measured quite yet. So the product team has to figure out how to measure it, put the measurements in place and so on. And then they spend the entire first quarter of the OKR totally focused on the KR itself in terms of establishing it and getting it to actually work in the first place. And that's where all their mind share goes.

And what I was telling him, and he was kind of relating back to me, that that's what had happened previously. So it was a colossal waste of time. And I was like. Dude, I know exactly what you're saying.

It is a waste of time. We will not be doing that. Whatever ends up happening for the KRs will make them directionally make sense. There's easily available measurements out there that we can and should take.

Let's take those. And if they're not exactly correct, it kind of doesn't matter because at the end of the day, kind of like this puzzle thing that we spoke about before, we need to figure out what we're doing. And the KR can change. Like on day two, Care doesn't make sense.

Toss it. Get another one. Initiatives one, two, and three don't make sense. Punt them.

The whole point of this exercise is not to be obsessive and fascinate ourselves around what the care is and how we measure it specifically in this, that, and the other. Jettison all that thinking because it's a waste of time. We were just going through this back and forth and eventually at the end of the chat, he was like, yeah, Brandon, I like what you're thinking here. Let's give this a crack.

100%. And the other thing I really hate is one is going off and having to work through the KR, and the other one is I really don't like compound key results. It's like a number that's a function of a formula of five different things. I don't care that we're making it really clear of one number.

You're hiding everything, and you can't actually see what's driving it and what is and isn't working. That's another one that people tend to really think they're clever if they come up with these random. Brand new metrics. Literally create a brand new defined metric that constitutes all the the stuff that we actually want to see.

All right, last question. She talked about not just being a fractional, but building a fractonal team. And are we seeing a new operating model emerge? And the quote in this case, they're getting a strategic CEO, which is me, plus a whip smart chief of staff and some admin support.

I'm bringing the tech startup intensity of operations into SMB where it's sorely needed. What do you make of this fractional plus team orientation that you described as a value prop. Bit of a lightweight consultancy. I don't think I have anything profound.

Do you have anything profound? Just in the sense that it just reminded me of Pete Crosby. So for those that don't know, Pete Cresby is a guru for revenue coach, I suppose, for a lot of folks. He's a well-established CRO.

So Pete had a very similar concept that he was kind of talking to me about ages ago, where he's one person and he can only stretch his time so far. So I think his idea was to bring together a bunch of operators with a bunch revenue skills, a mixture of skills effectively as a collective and then deploy them into. Organizations as a bit of a tag team. So it's a bit of a similar concept and I guess conceptually, it seems to make tremendous sense because obviously with any company that has revenue challenges, pulling in different skills is a bit of a SWAT team to get them into a different position seems to make sense to me.

It seems like a good idea. And this time it's on the operations side. But again, if you do have that kind of network that you can bring together. So not thinking about it on the buyer side, but on the creator side, it's a lot of business development or a lot mouths to feed in order to keep people working.

And so it's just like, is there enough demand? And how do you build that demand? Yeah, because it's all bespoke. I mean, it's hard enough to, like, bespoke yourself as this EO into an actual fractional gig, never mind a team of them.

All right, last observation slash thought slash question. Alicia Diamond, the diamond method, we like that. We like that phrasing. She needs to create an EOS equivalent and call it that.

We told her, we came up with it for her on the podcast. I like Alicia's approach and I like the kind of the non-approach approach. So then the question is, how do you have a book of frameworks and explain how and when to apply the frameworks or how to apply the frameworks lightly? There's definitely a challenge to creating the diamond method, but I'm looking forward to Alicia figuring that out.

So on that note, let's wrap it up here. Let's go to our chat with Alicia Diamond, the Diamond Method. What made you decide to come off the ladder? A couple of reasons.

I was tired. I think a lot of us find ourselves sprinting for years on end. And as much as we say to ourselves, it's a marathon, not a sprint, we end up sprinting marathons. And you can do amazing work that way.

And I guess I'll just speak for my own experience because that's the only one I know, but you can begin to lose yourself. And lose perspective. And I recognized that I had lost a bit of perspective, lost a bit of understanding what else was out there, had de-prioritized health and kind of those other life buckets and wanted to create some space to get that back. And then I also realized that I was not on a steep enough learning curve.

So on the one hand, I knew I needed to rest and cover. On the other hand, I felt a bit like I have run this particular marathon course over and over and over. And I'm someone who really values like, put me in a new environment where I don't actually know what's around the corner. So I was craving change and craving just a bit of a reset to understand and kind of appreciate what else is ahead of me.

And that sounds so much like my own journey and also in my own career, like definitely always been the glue, want to keep learning. As I think you know, and obviously our listeners are going to know because I keep mentioning it all the time, just became a CEO. Part of what I've been talking about for the vision of what it feels like to work at the company is that we're not going to scale, we're not going have thousands of people, we are not going do the old SAS model, because been there, done that, have the...

Sticker or whatever. I can't think of what the the badge. Yeah, the Girl Scout badge. Yeah, exactly.

And it's just like, there's just no challenge to it anymore. And so rather than changing industries, what I have challenged the team with is, can we get to 100 million with 50 people? How do we use AI? How Do we write the new playbook?

And so what you're saying, yeah, it just really resonates with me. So you decided instead of Doubling down on AI to actually move out of tech to learn new things. That seems very scary to me. Well, I will share that the number one reflection I got when I told people I was leaving, they came to me with a lot of assumptions.

So I was at a series C FinTech company. So people were like, great, you're gonna go be a COO at a Series D FinTech Company. And I said, no, to your point, Bethany, like FinTech, been there, tried that, want to experience a different playbook. And oh my gosh, the reflections I got back.

I'm like, that's so scary. What are you going to do? And I felt so confident in myself, which is something I wish for everyone. I said, I don't know yet, but I have this confidence that it will come.

And let me just say that it comes from a place of privilege, and I don t take that lightly. But to have the confidence to say, I will figure it out, and to look at the twists and turns and figuring it as incredibly valuable and that's That's exactly what I did. So as I started having conversations with people, I stopped talking about my career thus far with the easy things, the things I've mentioned on this conversation so far, the title, the here we're our investors, you know, it was FinTech and started talking much more about here's the kind of work that really energizes me, here's kind of the work I love, hear the people I love.

The types of people I love to work with, here are the types challenges I like to solve. And I often describe it as building product, right? It doesn't actually matter what I think it matters, what resonates with the market. And the second I took myself out of this box of COO venture-backed fintech and started talking about the other elements of it, the reflections I got back were, Oh, wow, I could see you being really successful in this environment, or you should talk to someone in this other industry.

And I felt like I was gathering little threads of curiosity, and I just committed to myself like I am going to pull on every single thread because I jumped off the ladder to explore and see what's there. So let me not have any preconceived notions about where any of these particular threads might lead to. And where those threads led to is I did have some conversations with companies that were venture-backed, tech-oriented, who wanted to do the scale thing, you know, the been there, done there, that playbook as you're talking about, Bethany.

I also went down a path of considering buying a business, I think. Most people have seen the headlines. They're in the Wall Street Journal. They are in everywhere right now about we're on the precipice of this massive transfer of wealth, of small businesses, and they're in need of really strong operators.

So I went down that path for a while. I went on a number of different paths. What I kept doing and collected from each of them was really this honest. Assessment of does this resonate me like is this is this a jog I want to take if it's a jog I want To take it might be a marathon course I want to run.

So kind of keep going after what's interesting. You're in your job, doing your work, your title, your salary, you know, your influence in the company. And then at some point, you start thinking about other things. What is it that I want?

What energizes me? Did anything happen to kind of instigate the thinking? When thinking started happening, he went out for reflections. Who was doing the reflections back to you with these like mentors or just walk through the process a little bit.

Yeah, a couple of things instigated me thinking. And I'm a big believer that if we don't proactively pause and listen to ourselves, other elements, namely your body, or hopefully, hopefully not, you know, your family or something else will get louder and louder and louder until you listen. So the quick version of this is I... Woke up one morning with some neck pain.

I'm someone I've always carried tension in my neck and shoulders and I ignored it and I just took some leave and it got worse and worse and worst. I woke up in the middle of the night. I couldn't raise my head and I was actually going in and out of consciousness from the pain and I kind of kicked my husband awake and I'm like, something is seriously wrong. We went to the ER where feel compelled to share this.

They're like, oh, you're a woman in your 30s. Do you ever do yoga? Yes. Well, okay, there is a chance that you might have torn your jugular.

Let's do it. And I'm like, Oh my God, this is terrifying. It turned out to just be a pinched nerve, which is excruciating. But it was a wake up call where all of a sudden I prioritized physical therapy.

And this was like I have to go to PT three, four days a week because I don't want this pain to come back. And I'm not proud to say this, but that was a little bit of a wake-up call to me, like, wow, it took this for me to start to prioritize my health a little but each day. And I was able to use that one step to kind of snowball into where are other areas where I'm kind of not taking care of myself, not having some balance. And that created just enough of a disruption.

In my habits to start to gain this new perspective to say, well, wait a minute, I am sprinting. Look up what is the end. I have to. I am not a runner.

I guess I'm just good at using the running metaphors, but full disclosure, I'm not a runners. So don't take it. Don't ask me running questions, but to kind of look up and say, oh, I've been on this course. Oh, this is a similar problem.

Oh this is actually like a flatter learning curve that I want to be on and so. That's what kind of started the thinking, started some conversations with those closest to me. And then Brandon, to answer your question, the way I approached it, it was advice from a trusted friend, and she's like, think of the people in your life kind of in these trusted circles of the People you can go to first with really messy thinking. And then there's that next tranche of people where they do better if you come to them and say, I'm thinking of.

Making a change. Here's idea one, idea two, idea three, what might I not be thinking of? And then I think we all have people in our network, one click out who are better for hey, I have a very targeted idea. Do you know someone in this industry?

So I started with those who were closest to me, friends, family, trusted. Mentors, I like to call them like my personal board of directors, but people who I could go to and say, Hey, you've seen me over my career, you see what I'm good at what I've not so good at. If you could drop me into doing anything, like where would you want to see me go? Where do you think my talents could be really applicable where that I haven't even explored before.

And although we're really focusing on the journey today, I just really like where have you ended up and then maybe we can so we have where you started we have some of the journey very curious where you finished and then i think we might go back to. Yeah, absolutely don't want to leave everyone hanging. So where I am today is, and I touched on this a little bit briefly, I contemplated buying a business. And I, again, putting my, if I was building product hat on, I'm like, let me go immerse myself into that SMB world, specifically here in New York, see what it is like, try before you buy.

And found my way into... An opportunity to operate as fractional COO SMB, they often call it integrators from the EOS model, but serving as a fractional operator to a number of businesses, but really bringing them not just me, but more of a team approach. So they're getting some strategic COO with me, they're getting some execution support from a whip smart chief of staff type person coming out of tech. We bring in some admin support as well, but to bring that intensity of operations that I think a lot of us grew up with in the tech world, bringing that over into SMB where it is sorely needed and there's a ton of impact.

And I could go on and on and talk about this, but that is where I'm focused today and I'm really bullish on SMB overall, especially with this tsunami of AI. Are you starting a company then? Cause you're talking about other people in your team. It's not just you going out and being a fractional, which so many people have either opted to, or had to do in the last few years.

I know the answer isn't you went out to start a company, but at what point did you realize, Oh, what I'm doing is starting a, I'm not just being a fractional myself, or I'm looking for a new career. I had a couple, trust. People say to me, don't just build yourself a job, build something. I am a builder.

I'm not a good maintainer. I networked my way into meeting a couple of super connectors and so started getting a lot of inbound interest from different owners and I want to help them all and I personally can't, and I'm someone that I love building a team. I love having a team, I know a lot of fractionals want to be solo because they're like, I never want to responsible for building a team or performance management or anything that goes along with that. I get a lot out of that.

So once I saw the traction and once I saw that the owners I was pitching, they were very open to this team model versus just having a person. I said, okay, let's pull the trigger and evolve and see how I can scale this. That's cool. So then from an EOS standpoint, you go into these organizations and say, look, we're going to help you transform your business.

This is not just me as a fractional, but in fact, I'm going to bring in a couple of different people custom built to solve a particular set of problems that you have. Correct. Yeah. So is there going to be an Alicia Diamond way of doing things?

Like are you creating your own new playbooks and new methods? Is that part of your long-term vision? Love that question, because I think there is a part of me that has never admitted that maybe I would love to be one of those people that comes up with a new framework. I love, I love frameworks.

And so maybe coming soon, I should trademark something in advance maybe what I'm finding quite effective now is most owners and to contextualize it for the for the listeners we're talking about at the smallest scale call it like three million in revenue up to about 50 million in Revenue private so it's the owner as the operator rarely do they call themselves the CEO they call themselves the owner they have done an extraordinary job of scaling the business to where it is based on their passion for the product or service, but they are not a typical business person or have the kind of that operator bend to them.

What I find is most of them are familiar with EOS. I'm sorry, Gina Wickman and team, but many of them allergic to EOS, they say, oh, I'm familiar, but ooh, accountability. Ooh, that sounds heavy handed. That's why I started my own business.

I don't wanna be in that environment. And so what I found that resonates is the ability to take a little bit from multiple frameworks and customize it to what. They need. So they might not like EOS, but they do like this idea of delegating more to their team, elevating what they do, understanding proactively how their business is performing versus waiting until they get a financial statements.

They like concepts of it. They just don't like the kind of rigid we're implementing EOS. So sometimes I pull in from OKRs, or sometimes I pull in even for strategic planning, like business model canvas, I'm able to pull from across my toolbox and have it feel bespoke. And it is to some degree, but at the end of the day, it's the same.

It's the fundamentals are the same across all the frameworks. What I get stuck doing is one of two things, either fear of like, this is the only bus that's coming, so I better get on this bus and then get myself really distracted doing a project or something that sounds interesting but doesn't move me forward for the rest. That's happened like two career breaks ago, the most recent career break. I had more of a plan of what I wanted to do, but I just wanted to so many things.

You know, I did pottery classes and writing classes and started a podcast and like ended up filling my time with things that I loved exploring but didn't necessarily move me in a direction. So my question is, how do you know when to say yes and how do you know what to say no while you're in that exploratory phase? Yeah, I think it's somewhere in the middle of what you're describing. I think there is an extraordinary amount of value in all of the things that you rattled off that might seem totally out of left field like the pottery class.

Being able to tap into, you know, why are you taking a pottery class? Because you want to create something, presumably, I don't know. Like, you know, it's very tactile, it got out of my head deeply into my body and a totally different skill. It was quite meditative.

So one of the things I realized, not from a pottery class, was that I missed quiet, creative space that my day-to-day had turned into meeting, meeting, meeting, chasing things down, facilitating, making impossible decisions that found their way to the top and I missed that sense of accomplishment, frankly, that comes from sitting down and creating something. So much so, I'm one of those people where sometimes I'm like, I'll take a first crack at building the financial model because it's just discrete and fun.

You're speaking to Bethany's heart here. Yeah, I just, you know, I save the Excel as my dessert. Love that. It makes other people so people are like, Excel is my vegetables.

I'm like, no, Excel, is my dessert. So I think there is wisdom in everything. And I cannot take credit for this myself very fortuitously. If folks are familiar with this book, the Silicon Valley companies have their leadership teams read it and organize around it.

And I was fortunate to be able to join a Conscious Leadership Forum, which is a small group of people, there are eight or 10 of us, and we meet once a month for an entire year and really internalize those commitments. And, and what that process is all about is really integrating and waking up and Discovering being aware of your experience. You're doing something and you're not even aware that you dislike it or it's draining or just being a little bit more impeccable in terms of how you're showing up as a human being, being honest, going in and having a clearing conversation with someone rather than letting emotions fester.

And so I think what you're hearing in me is a lot of my journey since I left my full-time role. Is this integration and self-development as well. And so I viewed everything as wisdom. And there were lots of, at the beginning of my break, I was not as productive as you, Bethany.

There were lots walks, lots of - I did have my hot girl summer - but lots of time outside, lots of times with friends, and then just pursuing these conversations and opportunities. As they popped up and being okay with trying that just because I said yes to this one opportunity and I got into the project and I'm like oh gosh I don't want to do this that's okay I'm better for it I learned from it I made a contact I have a little case study about my ability to do this but to not get stuck and that version one is my version forever it's just it's just version one and learn and pivot into version two.

I definitely have that as well, like permission to say no as much as permission to say yes, or you say yes and then you go, Oh, change my mind. That wasn't as much fun as I thought. And that's okay. You don't have to always stick with it.

Stick with it when even if it's horrible, there's something in you that wants you to do it, don't stick with that because you're afraid of failure. It's really hard to get into this abundance mindset that there is infinite opportunity and to not have this scarcity mindset gripping on to whatever's in front of me, I have to do it, I have hold on to it, and that requires this leap of faith. It's very much a mental and emotional shift, but I think as you're designing your career, It is not just your career.

Most of us wrap up our identity in our careers. So to the extent folks are considering making some kind of pivot, just be prepared that this is an emotional spiritual journey as well. And if you try to ignore that, it will get louder and louder and outer, but to approach it in a very integrated. So much of what you say resonates with my experience, definitely around abundance versus scarcity in the mindset, and also privilege and the ability to be in a situation where we can explore.

But it's just hard right now. There's not the money swashing around that there used to be. The economy isn't as good. People who maybe aren't ready for these emotional journeys and just want a job.

But are struggling to find a job, or feel like all I need to do is there's abundance, so I'm just gonna talk to people, but then it doesn't work. What do you say to those who are listening that's maybe had more of this experience of like, where's all this abundance you're talking about? I don't see any of it. I need pay my school fees.

Need a job. Yeah, so I was fortunate working at Long Term Stock Exchange. It was founded by Eric Rees, who wrote The Lean Startup. So my time there very formative and getting me to think about what is the hypothesis?

What are we testing? What is the data telling us in terms of how to proceed? So I think for my advice for anyone out there where maybe they are just having conversations. If no opportunities are being created from that, if you're going into a conversation saying, I am a out of work COO and I'm going into this conversation and I am positioning myself as that, and opportunities for anything, even just project work, or let me introduce you to someone, or look up this company, it might resonate.

You have to be honest with yourself. Like, okay, something about your, how you're showing up or your pitch or your value proposition is not resonating. And you have to open to continually iterating on how you are showing up in the world. And I think I benefited from dropping into this totally different world.

It's still business, but dropping in and talking with SMB owners, you can't use the acronyms. They don't care. They don't know who a 16 Z is. They don't care that I worked in a company that they're like, okay, whatever.

If anything, they're actually turned off by some of that. And it was a really valuable opportunity for me to hone how I talk about my skill sets, which I believe as operators, our skill sets are universally applicable. So if I were looking for full-time job right now. First of all, I would probably reframe it and say I'm looking for work.

I think we're in this golden age of fractional right now, which is just a rebrand of consulting. But there's a lot of talent available. Companies post-COVID hiring sprees are open to this because it's a heck of a lot easier to get rid of a fractional than to say you have to do a layoff. And so I would reframe from it has to be full-time to I have to find work.

And I would also broaden the aperture in terms of it doesn't have to be this specific title. Here is the impact I want to make on a company. So as a COO, I'm obsessed with margin. I'm obsessed with building the scalable operations that allow as revenue keeps growing to keep more and more of that because you're improving your margin along the way.

As you mentioned at the beginning, Bethany, what if we build a hundred million dollar company with 50 people? I love that as a thought exercise in terms of how to build the company. So I think getting crystal clear on the type of impact you want to make because that's what will resonate with. Whoever you're approaching for work.

But that requires a level of self-reflection and humility and getting clear about what impact you can make and then going, having the conversation, having someone you admire, they might look at you and say, what are you talking about? That doesn't make any sense, but you learn from that conversation and you go onto the next one, onto the one. And I often remind myself, there are what, eight billion people on this planet. I can afford to have 10 or 20 awkward conversations that I'm kind of mumbling my way through in service of finding something that resonates.

It's interesting. I have a friend of mine, it's not in the operations field, but in the talent sphere. So, a phenomenal guy, very talented. He's had three years of consistent layoffs, contracting for three or four months, you know, another job, another layoff.

And throughout that entire time period, which lasted almost three years, you definitely had a lot of low points. And I did my best to shift his mindset, you don't think about how to optimize his pitch, things to think about in terms of the way to look for work. Do you have any words of wisdom in this space? I vividly remember during that job search, I just kept having to remind myself like, it is a numbers game.

And the more people you talk to and the more sports analogy, like at bats that you have, right? As long as you are serious about receiving the feedback and constantly improving, like doing your own little retro after each conversation. It is a numbers game, so just keep going. I think also candidly the world has changed dramatically since the last time I was looking for a full-time job.

So you look at roles on LinkedIn today and they like stop accepting applications within the first couple of hours because they're getting inundated. I would really creative and if you're not feeling creative, this is what our favorite chat GPT colleagues are for. And find a way to stand out. And the way I've always done that is I find businesses that I think are really interesting.

I find the email address for the CEO or the owner and I say, hey, I think what you're doing is really interesting, I say what is actually interesting to me, here's my background, here's what I like to do, if I can ever be helpful, reach out. But putting yourself out there in a differentiated way, don't just keep doing the same thing, it will yield the same result. Delicious If our listeners can only take one thing away from today's episode, what is it? Approach building your career as a smart product person.

Define hypotheses, test them, listen to the data, and be comfortable following the data. If product doesn't rise, be a scientist. Just be rigorous in terms of experimenting and paying attention to the date that comes back to you. I'm gonna add one more piece of advice, which is don't take it personally.

Look at yourself as a product. Nice. On that note, thank you Alicia Diamond for joining us on the Operations Room. If you like what you hear, please comment or subscribe and we will see you next week.

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