Sarah Wilson: Most strategic plans don't fail in the boardroom. It's about two layers down on the calendar of a manager that nobody has invested in since the day they got promoted. SHERM or the Society for Human Resource Management surveyed over 129 CHROs for their 2026 priority report. Forty six percent named leadership and management development on their top priority lists. And that's the second year in a row it's landed on their list. Gartner's CHRO survey found the same thing. When that many people agree that something's the problem, it's usually because they've seen it play out in their own organization. You've got a plan. It's a good plan. It's mapped out properly. You've socialized it. You've resourced it. And six months later, about 40% of it's moved. So you go looking for why. What's the reason? It's not the strategy. It's not the market. It's that the layer of people responsible for turning the plan into work were promoted because they were excellent at doing the work and nobody ever really taught them about the second job.
Penny Cook: That layer is where execution lives. Your directors and senior managers are the ones deciding what gets staffed and what gets dropped, and what stays on someone's plate for another quarter without anyone deciding it should. If they're running on instinct and goodwill, your plan is running on instinct and goodwill. This holds in place because it looks like discipline. You've got a tight operating cadence, weekly one-on-ones, clean dashboards. Everyone's calendar is full. It feels rigorous. But an operating cadence measures the work. It doesn't build the person doing it. Those are two different jobs. And one of them tends to get postponed until the person quits or plateaus.
Sarah Wilson: The good news is that Fix isn't a really large formal program. It's three things that you can start inside your business next week with the people you already have. Hi, I'm Sarah Wilson. I'm a fractional COO and operational turnaround partner for SMB. I help businesses struggling within the operational core of their business, and I work with founders to install scalable, repeatable processes. That unlock the ability to grow with the teams and tools they already have.
Penny Cook: And hi, I'm Penny Cook. I'm also a fractional COO and a strategic operations consultant, helping product and consumer brands install, upgrade, and run scalable operations and operational systems that reflect the founders' unique vision and ambition. Let's get into the this because it's such an important topic, Sarah. How do you grow and develop your middle management layer into that functional translator between strategic executive vision and the actual work getting done? This is an essential to every business, and there is not a lot of resources. for people who get promoted or put into these positions to fill that in between spot.
Sarah Wilson: Exactly. And I think Penny that sometimes we forget that within our businesses we actually need to focus very intentionally on the development of our teams because we usually have people like I just mentioned who are really good at doing the work itself. So they're they have a lot a high degree of competence at getting the work done. So sometimes we think, that's not someone I need to worry about, but that's not the case.
Penny Cook: Yeah, that's that's so true, Sarah. And bringing that up, that brings us to our first thing that we want to talk about today. to stay connected, how do you how do you actually turn those people into the people of the future? Thing number one is turn your one-on-ones into a conversation about the future. You obviously have work that you need to do today, but it is just as important in the long run for your organization that you're talking about the future. with the key people in your organization. You almost certainly have a one on one meeting that you could fit this into. So this isn't about adding anything different to the calendar. It's about changing what these meetings are for and how you're treating your and how you're discussing the importance of the business with the people you're having one on ones with. So so most standing one on ones drift into status, right? They're either once a week
Sarah Wilson: Absolutely.
Penny Cook: month, twice a month, that you're talking about blockers and updates and decisions. And those are very important things in an operational organization. It's useful. You need to have these conversations, but you also need to protect some time to pick a cadence and commit whether it's in every meeting once a month, once a quarter, it doesn't really matter what what that time is as long as you're using it well. Name it on the invite, make sure that you're both prepared for it and call it development. Talk about where you're headed. What skills can your manager or your individual contributor develop and show you that allows you to help them be prepared for that next move into that management slot in your organization?
Sarah Wilson: I love that. And Penny, I think you and I've both had experience within our leadership careers is the moment you prioritize someone's development is it's really it usually goes really well. At first some people might be like a bit might not have the confidence to name out loud where they want to go or they're not sure. But the more you make development part of the conversation, the more that those people usually step up. They usually start reflecting, working on themselves. So it's, it's, you know, when you talk about the future with people, they can start seeing the future too. And that's a really exciting development for those really talented people that are already working within your business.
Penny Cook: Yep, that's true. You want people who want that path forward because those are the people who are going to look to make a difference in the organization and in themselves in the long run. So two things that you really want to understand in these conversations before you dive into talking about the future is where is that person right now? Where do they see themselves? And where do they want to get to? What is their vision? And tell them not to be shy. If they you know, give them the freedom to say, I want to be in your shoes. And then tell them
Sarah Wilson: Mm-hmm, exactly.
Penny Cook: Let me help you get into my shoes. Let me be the person who helps you get here. it buys an immense amount of loyalty and motivation and goodwill in your organization and it unlocks the capability to get more things done with that person. And it also doesn't leave you without a plan the moment you need that person to step up.
Sarah Wilson: Exactly. It really plays both those parts.
Penny Cook: Yep, for sure. So one thing that you can do this week, open your calendar, take the next four one-on-ones with each of the managers or your individual contributors and rename one of them and then hold to it. Have that discussion. Find out what they want their career progression to be, talk to them about what that looks like, and keep that in a cadence on your calendar. Keep talking to them about it. Keep giving them feedback about what you're seeing and let them grow into that role with the company.
Sarah Wilson: I love it, Penny. That is such good advice. And with the calendar open, if you will, that brings us nicely into the second thing that you can do is schedule a work with with that person. So, a work with, of course, if you're in person, walking the plant floor, in the office, working together. Now, it doesn't have to be a full day, it can be as short as half a day. And sit down and just observe, just understand what your What you're looking for is around things, what are the blockers? What are the challenges that come up? And there will be an element of your leaders potentially giving you the best version of their day. They're going to probably going into that work with the knowledge that you're sitting there watching, there will be an element of you're going to get to see the best version of what their day looks like. And perhaps not the one where everything goes wrong. And that's okay. You're going to get enough information from this work with. To answer the questions you want to answer and what are those questions, you want to know how many systems that they touch. I know you probably have a really great familiarity with the majority of the tools. And and when I say tools, be it software or hardware, whatever it may be, you do have a good understanding and handle on what those are in your business. Tools are, however, one of the things that can creep quite Easily and quickly. So since the last time you visited your stack, I almost guarantee you there have been a few more kind of things shoved in there to either fill some holes or smooth some problems. And that's okay. That is a natural, completely natural thing that happens in the business. But having to work with will give you a fresh perspective on the tools that are being used in your business.
Penny Cook: Absolutely. And Sarah, the first time you do this is a very sensitive time. So you have to be really careful how you're received, right? You want to have had the discussion or several discussions with this person that shows them that you're interested in their future and you are you are you are coming to that work with with that in mind. You're not coming there to micromanage them, you're not coming there to criticize how they get their work done or with a suspicion that they're not. You're coming
Sarah Wilson: Yes.
Penny Cook: Really understand how they work to help them be the person who gets to that next level. And one really important thing to be received well is don't give them criticism on the spot. Don't fix anything in the room. Be their partner. Be an observer. Don't act like you're there as a spy. You are really there to partner with them to help make them better. And if there is any misunderstanding about why you are there. It could potentially be counterproductive. So just, you know, be careful about how you're received and how you've teed that up with your team member.
Sarah Wilson: Exactly. And if it feels awkward and it there's a good chance it might, that's just
Penny Cook: It my
Sarah Wilson: yeah, exactly. That's a signal that it's it's it's in good time that this is the right thing to do. So like Penny just said, as long as you're not trying to fix anything, you're you you keep that promise to yourself about just being an observer, that awkwardness will pass. And then that person who's who's you know work you're working with, you you have a real opportunity to observe their day to day and they will trust that that's what you're there for. that awkwardness that's probably gonna be there doesn't last that long.
Penny Cook: Yeah, and I can hear you out there saying, I don't have time for that. I trust my managers. They're getting their work done. I have very important things I need to get done. And we hear you. We hear that that is a concern. And we as managers have the same pushback for ourselves. What
Sarah Wilson: Mm-hmm.
Penny Cook: I want to say to you is try it one time and see what happens. See what happens.
Sarah Wilson: Exactly. Exactly. You're so right.
Penny Cook: It will be valuable. Or it will be a moment for you to reflect on what your relationship is with those team members to be able to readjust so you can be the person who is facilitating their path forward.
Sarah Wilson: Exactly. So think of that as an investment to make. Just maybe frame it if you did to get comfortable with the idea. Is that time that you're going to invest in that person will return to you in many fold, we promise. So one thing to do is again, with that calendar still open, is book that work with again, it just can be half a day with that manager or individual contributor. Do it now, book it in the next two weeks.
Penny Cook: Yes. And while you're thinking about that, let's go on to thing number three, which fits nicely with understanding your managers, seeing how they're facilitating their work and facilitating the the path forward for them. Inventory the tools and the skills in your organization. The first two things will tell you about one person at a time, and it is very important as a leader that you do that for the direct reports in your organization. This thing tells you about the whole operation. And it's one of the most it's one that most of us have cut off the longest because it isn't a conversation, it's an audit, and it will happen on an ongoing basis. So put together two lists. One, what tools are people using to manage their work? And what skills does the work require versus what skills you have today. You want to understand where there are needs and where there are gaps. And I'll bet you have an intuitive sense of what that already looks like for your organization. So test yourself.
Sarah Wilson: And when someone's as familiar as you are with your business, it might take a little bit of pausing and reflecting to truly dig down on what the skills are. Because when we're so busy in the day-to-day of running our businesses, we kind of get stuck on the how this gets done. And the how this gets done isn't necessarily the same thing as the skill behind it and not only behind it, but what does good look like? So just If you need more time and reflection to truly reflect on the what skills, that is completely normal to need to do. Just something to think about when you go through the inventory.
Penny Cook: That's right. You wanna really evaluate based on what the real work looks like, how much data literacy do you need? How much vendor management experience do you need? How much reading a PL. Or understanding unit economics. How much do you really need of each one of those and how much is present on your team? At the same time, Sarah, we want to look at those tools in a really honest way in order to be able to do that skill assessment. And this isn't just an email to procurement saying, hey, send me a list of all the tools we're paying for. You want to suss out like where are the Trello boards that individuals
Sarah Wilson: Mm-hmm.
Penny Cook: are keeping to track their own work or their to-do lists in their notebooks. Or a tracker on someone's Google Sheet or something that someone has set up that they're sharing with a few team members because it's allowing them to manage a process. Suss those things out, figure out what's working. You can you can do a process improvement measure later. You just want to deal with reality here. And what is it really taking to keep your team running right now? And what's it going to take to build them into the future?
Sarah Wilson: Exactly. And I I I love that penny. It's it's such an important inventory to make. And what can tell a lot or tell you a lot about your business is maybe we're using different tools for different things. Like that Trello board is where production lives, but finance is using Google Sheets. And maybe for good reason. but also just that gives you real insight to how the work's getting done and And while you're not focusing on the process improvement piece now, it might help inform really important improvement measures that you do down the line in the future.
Penny Cook: Absolutely. And one thing you can do right now to get this done, commit to yourself that you're going to make one page per team in your organization. Two lists side by side, a list of stool tools and a list of skills. Do each one of those and really assess how well your organization is set for the future and what you might need to fill in those gaps and then how you can go back and work with the managers and your team to either fill those gaps themselves or look to fill out their organizations to run those complete teams as managers to help them get to the next level.
Sarah Wilson: Exactly. So None of this, none of this, none of this is a really large development program. There isn't a huge launch, and that's on purpose. Programs take a budget cycle, sometimes a vendor, a launch date, a Gantt chart. And that's not what this is. This is simply changing and shifting your leadership style and leadership practice to focus on the development of your team. What we're describing and suggesting is lives on your existing calendar and using the existing time you already have and of course the teams and tools that you already have. So three things. Turn one of your standing one-on-ones into a real conversation about your team's development. Go sit with that manager for half a day and see what reality looks like. Add the inventory of the tools and skills your business is actually running on. before you decide w where you need to invest. This is the kind of work that Penny and I do with our clients all the time. Get in touch if you'd like to walk through it with us. If this was useful Subscribe to wherever you get your podcasts. And send it to a colleague who's carrying a middle layer that needs more support than they're actually getting. You can find us at operating-on-purpose.com and on LinkedIn.
Penny Cook: Because great businesses don't just happen. They operate on purpose. Thanks so much, Penny. Sarah, that was
Sarah Wilson: Thank you so much, Penny. Thanks everyone for listening.
Penny Cook: a great discussion. Thanks for joining us today. See you
Sarah Wilson: And we'll see you next time.
Penny Cook: next time.
Sarah Wilson: There.
Penny Cook: That layer is where execution lives. Your directors and senior managers are the ones deciding what gets staffed and what gets dropped, and what stays on someone's plate for another quarter without anyone deciding it should. If they're running on instinct and goodwill, your plan is running on instinct and goodwill. This holds in place because it looks like discipline. You've got a tight operating cadence, weekly one-on-ones, clean dashboards. Everyone's calendar is full. It feels rigorous. But an operating cadence measures the work. It doesn't build the person doing it. Those are two different jobs. And one of them tends to get postponed until the person quits or plateaus.
Sarah Wilson: The good news is that Fix isn't a really large formal program. It's three things that you can start inside your business next week with the people you already have. Hi, I'm Sarah Wilson. I'm a fractional COO and operational turnaround partner for SMB. I help businesses struggling within the operational core of their business, and I work with founders to install scalable, repeatable processes. That unlock the ability to grow with the teams and tools they already have.
Penny Cook: And hi, I'm Penny Cook. I'm also a fractional COO and a strategic operations consultant, helping product and consumer brands install, upgrade, and run scalable operations and operational systems that reflect the founders' unique vision and ambition. Let's get into the this because it's such an important topic, Sarah. How do you grow and develop your middle management layer into that functional translator between strategic executive vision and the actual work getting done? This is an essential to every business, and there is not a lot of resources. for people who get promoted or put into these positions to fill that in between spot.
Sarah Wilson: Exactly. And I think Penny that sometimes we forget that within our businesses we actually need to focus very intentionally on the development of our teams because we usually have people like I just mentioned who are really good at doing the work itself. So they're they have a lot a high degree of competence at getting the work done. So sometimes we think, that's not someone I need to worry about, but that's not the case.
Penny Cook: Yeah, that's that's so true, Sarah. And bringing that up, that brings us to our first thing that we want to talk about today. to stay connected, how do you how do you actually turn those people into the people of the future? Thing number one is turn your one-on-ones into a conversation about the future. You obviously have work that you need to do today, but it is just as important in the long run for your organization that you're talking about the future. with the key people in your organization. You almost certainly have a one on one meeting that you could fit this into. So this isn't about adding anything different to the calendar. It's about changing what these meetings are for and how you're treating your and how you're discussing the importance of the business with the people you're having one on ones with. So so most standing one on ones drift into status, right? They're either once a week
Sarah Wilson: Absolutely.
Penny Cook: month, twice a month, that you're talking about blockers and updates and decisions. And those are very important things in an operational organization. It's useful. You need to have these conversations, but you also need to protect some time to pick a cadence and commit whether it's in every meeting once a month, once a quarter, it doesn't really matter what what that time is as long as you're using it well. Name it on the invite, make sure that you're both prepared for it and call it development. Talk about where you're headed. What skills can your manager or your individual contributor develop and show you that allows you to help them be prepared for that next move into that management slot in your organization?
Sarah Wilson: I love that. And Penny, I think you and I've both had experience within our leadership careers is the moment you prioritize someone's development is it's really it usually goes really well. At first some people might be like a bit might not have the confidence to name out loud where they want to go or they're not sure. But the more you make development part of the conversation, the more that those people usually step up. They usually start reflecting, working on themselves. So it's, it's, you know, when you talk about the future with people, they can start seeing the future too. And that's a really exciting development for those really talented people that are already working within your business.
Penny Cook: Yep, that's true. You want people who want that path forward because those are the people who are going to look to make a difference in the organization and in themselves in the long run. So two things that you really want to understand in these conversations before you dive into talking about the future is where is that person right now? Where do they see themselves? And where do they want to get to? What is their vision? And tell them not to be shy. If they you know, give them the freedom to say, I want to be in your shoes. And then tell them
Sarah Wilson: Mm-hmm, exactly.
Penny Cook: Let me help you get into my shoes. Let me be the person who helps you get here. it buys an immense amount of loyalty and motivation and goodwill in your organization and it unlocks the capability to get more things done with that person. And it also doesn't leave you without a plan the moment you need that person to step up.
Sarah Wilson: Exactly. It really plays both those parts.
Penny Cook: Yep, for sure. So one thing that you can do this week, open your calendar, take the next four one-on-ones with each of the managers or your individual contributors and rename one of them and then hold to it. Have that discussion. Find out what they want their career progression to be, talk to them about what that looks like, and keep that in a cadence on your calendar. Keep talking to them about it. Keep giving them feedback about what you're seeing and let them grow into that role with the company.
Sarah Wilson: I love it, Penny. That is such good advice. And with the calendar open, if you will, that brings us nicely into the second thing that you can do is schedule a work with with that person. So, a work with, of course, if you're in person, walking the plant floor, in the office, working together. Now, it doesn't have to be a full day, it can be as short as half a day. And sit down and just observe, just understand what your What you're looking for is around things, what are the blockers? What are the challenges that come up? And there will be an element of your leaders potentially giving you the best version of their day. They're going to probably going into that work with the knowledge that you're sitting there watching, there will be an element of you're going to get to see the best version of what their day looks like. And perhaps not the one where everything goes wrong. And that's okay. You're going to get enough information from this work with. To answer the questions you want to answer and what are those questions, you want to know how many systems that they touch. I know you probably have a really great familiarity with the majority of the tools. And and when I say tools, be it software or hardware, whatever it may be, you do have a good understanding and handle on what those are in your business. Tools are, however, one of the things that can creep quite Easily and quickly. So since the last time you visited your stack, I almost guarantee you there have been a few more kind of things shoved in there to either fill some holes or smooth some problems. And that's okay. That is a natural, completely natural thing that happens in the business. But having to work with will give you a fresh perspective on the tools that are being used in your business.
Penny Cook: Absolutely. And Sarah, the first time you do this is a very sensitive time. So you have to be really careful how you're received, right? You want to have had the discussion or several discussions with this person that shows them that you're interested in their future and you are you are you are coming to that work with with that in mind. You're not coming there to micromanage them, you're not coming there to criticize how they get their work done or with a suspicion that they're not. You're coming
Sarah Wilson: Yes.
Penny Cook: Really understand how they work to help them be the person who gets to that next level. And one really important thing to be received well is don't give them criticism on the spot. Don't fix anything in the room. Be their partner. Be an observer. Don't act like you're there as a spy. You are really there to partner with them to help make them better. And if there is any misunderstanding about why you are there. It could potentially be counterproductive. So just, you know, be careful about how you're received and how you've teed that up with your team member.
Sarah Wilson: Exactly. And if it feels awkward and it there's a good chance it might, that's just
Penny Cook: It my
Sarah Wilson: yeah, exactly. That's a signal that it's it's it's in good time that this is the right thing to do. So like Penny just said, as long as you're not trying to fix anything, you're you you keep that promise to yourself about just being an observer, that awkwardness will pass. And then that person who's who's you know work you're working with, you you have a real opportunity to observe their day to day and they will trust that that's what you're there for. that awkwardness that's probably gonna be there doesn't last that long.
Penny Cook: Yeah, and I can hear you out there saying, I don't have time for that. I trust my managers. They're getting their work done. I have very important things I need to get done. And we hear you. We hear that that is a concern. And we as managers have the same pushback for ourselves. What
Sarah Wilson: Mm-hmm.
Penny Cook: I want to say to you is try it one time and see what happens. See what happens.
Sarah Wilson: Exactly. Exactly. You're so right.
Penny Cook: It will be valuable. Or it will be a moment for you to reflect on what your relationship is with those team members to be able to readjust so you can be the person who is facilitating their path forward.
Sarah Wilson: Exactly. So think of that as an investment to make. Just maybe frame it if you did to get comfortable with the idea. Is that time that you're going to invest in that person will return to you in many fold, we promise. So one thing to do is again, with that calendar still open, is book that work with again, it just can be half a day with that manager or individual contributor. Do it now, book it in the next two weeks.
Penny Cook: Yes. And while you're thinking about that, let's go on to thing number three, which fits nicely with understanding your managers, seeing how they're facilitating their work and facilitating the the path forward for them. Inventory the tools and the skills in your organization. The first two things will tell you about one person at a time, and it is very important as a leader that you do that for the direct reports in your organization. This thing tells you about the whole operation. And it's one of the most it's one that most of us have cut off the longest because it isn't a conversation, it's an audit, and it will happen on an ongoing basis. So put together two lists. One, what tools are people using to manage their work? And what skills does the work require versus what skills you have today. You want to understand where there are needs and where there are gaps. And I'll bet you have an intuitive sense of what that already looks like for your organization. So test yourself.
Sarah Wilson: And when someone's as familiar as you are with your business, it might take a little bit of pausing and reflecting to truly dig down on what the skills are. Because when we're so busy in the day-to-day of running our businesses, we kind of get stuck on the how this gets done. And the how this gets done isn't necessarily the same thing as the skill behind it and not only behind it, but what does good look like? So just If you need more time and reflection to truly reflect on the what skills, that is completely normal to need to do. Just something to think about when you go through the inventory.
Penny Cook: That's right. You wanna really evaluate based on what the real work looks like, how much data literacy do you need? How much vendor management experience do you need? How much reading a PL. Or understanding unit economics. How much do you really need of each one of those and how much is present on your team? At the same time, Sarah, we want to look at those tools in a really honest way in order to be able to do that skill assessment. And this isn't just an email to procurement saying, hey, send me a list of all the tools we're paying for. You want to suss out like where are the Trello boards that individuals
Sarah Wilson: Mm-hmm.
Penny Cook: are keeping to track their own work or their to-do lists in their notebooks. Or a tracker on someone's Google Sheet or something that someone has set up that they're sharing with a few team members because it's allowing them to manage a process. Suss those things out, figure out what's working. You can you can do a process improvement measure later. You just want to deal with reality here. And what is it really taking to keep your team running right now? And what's it going to take to build them into the future?
Sarah Wilson: Exactly. And I I I love that penny. It's it's such an important inventory to make. And what can tell a lot or tell you a lot about your business is maybe we're using different tools for different things. Like that Trello board is where production lives, but finance is using Google Sheets. And maybe for good reason. but also just that gives you real insight to how the work's getting done and And while you're not focusing on the process improvement piece now, it might help inform really important improvement measures that you do down the line in the future.
Penny Cook: Absolutely. And one thing you can do right now to get this done, commit to yourself that you're going to make one page per team in your organization. Two lists side by side, a list of stool tools and a list of skills. Do each one of those and really assess how well your organization is set for the future and what you might need to fill in those gaps and then how you can go back and work with the managers and your team to either fill those gaps themselves or look to fill out their organizations to run those complete teams as managers to help them get to the next level.
Sarah Wilson: Exactly. So None of this, none of this, none of this is a really large development program. There isn't a huge launch, and that's on purpose. Programs take a budget cycle, sometimes a vendor, a launch date, a Gantt chart. And that's not what this is. This is simply changing and shifting your leadership style and leadership practice to focus on the development of your team. What we're describing and suggesting is lives on your existing calendar and using the existing time you already have and of course the teams and tools that you already have. So three things. Turn one of your standing one-on-ones into a real conversation about your team's development. Go sit with that manager for half a day and see what reality looks like. Add the inventory of the tools and skills your business is actually running on. before you decide w where you need to invest. This is the kind of work that Penny and I do with our clients all the time. Get in touch if you'd like to walk through it with us. If this was useful Subscribe to wherever you get your podcasts. And send it to a colleague who's carrying a middle layer that needs more support than they're actually getting. You can find us at operating-on-purpose.com and on LinkedIn.
Penny Cook: Because great businesses don't just happen. They operate on purpose. Thanks so much, Penny. Sarah, that was
Sarah Wilson: Thank you so much, Penny. Thanks everyone for listening.
Penny Cook: a great discussion. Thanks for joining us today. See you
Sarah Wilson: And we'll see you next time.
Penny Cook: next time.
Sarah Wilson: There.
