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Episode 88

Sam McAfee - Drive transformation by aligning your leadership

Posted on: 07 Nov 2023

Sam McAfee is a Silicon Valley veteran, founder of the change management consultancy Startup Patterns and author of a book with the same name, Startup Patterns.

In this episode, we talk about the importance of aligning your company's leadership team in order to truly drive change and transformation. We focus on the key role of the CEO as coach and how CEOs can become empowered in that, and we also discuss the importance of mindfulness and of empathy, both for oneself and for others.

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“The most important thing for us as individual humans in an organization is to have as much empathy for each other as possible. And to try to not point fingers and attack each other in meetings, and let our tempers get the best of us.”

Intro:Welcome to the Agile Digital Transformation Podcast, where we explore different aspects of digital transformation and digital experience with your host, Tim Butara, content and community manager at Agiledrop.

Tim Butara: Hello everyone, thank you for tuning in. Our guest today is Sam McAfee, founder of the change management consultancy Startup Patterns, and also author of a book with the same name, Startup Patterns. He’s a Silicon Valley veteran, with 20 years of experience during which he’s helped create a number of digital products and develop a number of successful leaders in the digital space.

In today’s episode, we’ll be taking a deep dive into the key importance of aligning your company’s leadership in order to truly drive change and transformation for your business.

Sam, welcome to the show, thanks so much for joining us today. It’s great having you here. Anything you’d like to add?

Sam McAfee: No, that sounded pretty good. Thanks for having me, I’m excited to talk about this.

Tim Butara: Yeah, I think it’s definitely a great topic, as we just discussed a few minutes before starting recording. It’s the kind of topic that’s really at home here on our podcast. So I suggest we get right down to it. And the first question that I have for you today, Sam, is what would you say, or what have you seen be the biggest obstacles to leadership alignment?

Sam McAfee: So, I think that a good way to think about it is, when we talk about leadership alignment, we have to think a little bit in terms of the structure of organizations and how the leaders of organizations came to be in their positions. So, you could make some differentiation between smaller companies, or startups – some startups aren’t that small, but you could make a differentiation between size.

And in enterprise companies with thousands of employees, lots of departments and divisions, it can feel very different, but I think ultimately the same dynamics are at play. Because leaders are just people, and they have the same egos and the same psychology and the same faults and weaknesses that any person would have.

And so, in an organization, you could think about dividing it into three layers. You’ve got the senior leadership at the top, the executive leadership, with typically the CEO as the most senior executive. Depending on the legal structure and the way that they were formed, the CEO may or may not have people that hold them accountable.

Most companies have boards, most companies have shareholders and investors – not all do, there are plenty of privately held companies where there isn’t someone to hold them accountable. But either way, there’s a CEO with a group of other leaders that they have brought in to run different functional verticals like sales and product management and operations and finance.

And so imagine there’s a circle of executives that all report to the CEO, that’s one layer. Beneath them, there’s typically some kind of management layer; different levels of management to coordinate the efforts between the leadership team. And the third layer of the teams are individual contributors on the ground floor who are actually doing most of the work to make money for the business, whether it’s producing products or delivering services.

And so, when you say misalignment or a lack of alignment, I think it’s important for people to just think for a second of what we mean by alignment. In order for the business to be successful, it needs to produce valuable products and services for customers out there in the world.

And that requires at least two different ways of thinking. It requires looking outward, into the market, and having an understanding of what those customers actually want, what competitors are offering those same customers, and how our products and services need to differentiate. So there’s external thinking, looking out into the world.

And then there’s also internal thinking of how are we in our organization going to deliver those products and services effectively, given the people that we have, where we might be geographically, what markets we have access to, the skills and capabilities of our people, and also our technology. Is our technology new and shiny, or is it older and we have to fix a lot of things? So, being aware of the internal reality is really important.

So, first order of business is to align our external plan, strategic plan, with the capabilities internally and have a way of thinking about how to organize all those people to provide value for the market so that we can grow as a business. So all of that is just to say, here is the landscape of an organization and here is our goal.

Now, lots of organizations recognize those things and yet struggle to find that alignment. And I think that it breaks down in a couple of different ways. One that really jumps out is when different leaders on the executive team have competing ideas about what’s important and start to struggle for attention or resources or priorities.

A classic example in my industry, in tech, would be sales on one side of the table or perhaps product or engineering, or both, on the other side of the table. And there can be a struggle between what sales thinks is important and what product and engineering think is important. That’s one that comes up a lot, right.

And so, typically it’s because the CEO has not taken the time to work with their own circle of leaders to make sure they’re all operating as a team. The question one might ask is, well, how is the leader of the sales team rewarded or punished, based on what kind of performance? What are the incentives in the organization? Is it just to close as many deals as possible? Is it to bring in as many customers as possible? It kind of depends, right? And then, what are the incentives for the product and engineering organization? And are those incentives actually pulling in different directions?

So, I think the main thing that happens at the leadership level is that the CEO’s primary job is to recruit great senior leaders to work alongside, to be able to be responsible for these different functions; to delegate that responsibility to these leaders; to articulate the vision and strategy for the company; and then to make sure that those leaders that are in the executive team are all working really well together.

So, that sounds really obvious when I say it, but when you think about where most CEOs have come from – before they were CEOs, they typically did something else, right, most people didn’t start as a CEO at their first job. So, CEOs have a background; it might be technical, it often is more likely to be sales or business. And so I think that there’s a transition that all senior leaders go through where you have to leave the tactical details of a particular function behind and focus exclusively on leading and coaching and mentoring the people that report to you, right?

And so, I think that a lot of times CEOs will forget that. They’ll be too in the weeds about a particular aspect of the sale or a particular aspect of the product, and forget that their real job is to make sure all of their leaders that they’ve recruited actually get along and function and work like a team.

So it’s a little bit more like a coaching function, right, that level of coaching and support from senior leaders by their CEO is really important. And you can see the companies that have that level of sophistication and competence in their CEOs, because those companies function really well. For me, that’s the real key breakdown in alignment.

Tim Butara: And so, how can CEOs tap more into this coaching aspect of their role? How can they actually play this important role in helping drive this alignment in the leaders around them?

Sam McAfee: Sure. So, the main thing to look at – for a CEO that’s listening, I can express this as advice. But also I think it’s important for those of us who are not CEOs in our organizations to hear it and it will help us evaluate how our CEO is doing. So, to be able to look at them, and think, ok, is there anything that we can do to nudge them in the right direction?

So, the key thing to look at, the key metric, for any senior leader and a CEO above all else, is, how are they spending their time? Because what they’re spending their time on, what they’re putting their attention on, is usually a reflection of their values and their priorities and what they think is important.

And so, if a CEO is spending more time micromanaging aspects of the business that’s not their primary function– you know, there’s a point at which a growing company, the CEO may have to be involved a lot in the day-to-day operations. They may have to help with sales, they may have to bring in clients themselves, they may have to be involved in the product development and the product strategy to some degree. But at a certain point, the company outgrows that. And some CEOs are able to outgrow it, and some aren’t. I mean, I think they all are technically capable of doing it, but whether they’ve been effective varies from person to person.

And so, I think if you see your chief executive, when they’re able to spend a lot of time– there’s really two things that they should really spend time on. One is a fair amount of thinking work. So, like, thinking and reflection, quiet time. Strategizing, designing, writing, sitting in their office with a journal; there’s lots of ways that it might look to us externally, they’re doing these different things.

But the general idea of actually putting time into careful thought and reflection is a really undervalued skill. If you were to go right now to Amazon and look at the top, I don’t know, 20 leadership books, best selling leadership books of all time. Older ones, like Peter Drucker’s stuff, John Maxwell, all the way up to more modern books like David Marquet and Stanley McChrystal.

When we did a survey of what those books say to senior leaders on how to be successful, I guarantee that, if not every single one of them, the vast vast majority will have a section about how important it is for leaders to take time and turn off their phone and close their office door to think and reflect every day if possible, but definitely every week.

So there’s a certain amount of letting the brain do its work time that a CEO who is constantly running around and harried and going from meeting to meeting and never really taking that time to settle down and reflect, their brain just can’t keep up with what’s happening. And they make bad decisions. Because that time to reflect is really important for cognitive health, and to be psychologically resilient, you need time to stop and reflect and strategize and think about how you want to run your business.

So that’s one big chunk that I see a lot of leaders don’t take enough adequate time to really think about, what happened today? What’s going on? How can I reflect on that and improve for tomorrow? Or, what are the key things that I need to get done? Just that level of self organization and protecting some of their time. Then there’s only one other thing that they should be doing besides that, and that’s meeting with all their other senior leaders and having constant feedback and dialog about how each of them are doing in their job.

And that could be regular one-on-ones, it can be staff meetings, but a surprising number of companies that I encounter don’t have a basic healthy structure of leadership conversations that have to happen regularly, where the CEO can sit down and say, ok, you’re the VP of Sales. I brought you in to run the sales department. We check in once a week and we talk about organizational goals, we talk about your goals in particular; how are you doing as VP of Sales? What can I as the CEO help you with, how can I support you? Let me give you some feedback, do you have any feedback for me, that sort of thing.

Instead, what leaders tend to do is they just talk about the work. They’re like, how’s that account going? Are we going to make the such and such sale? How are our numbers looking? That’s not actually what they should be talking about. We have other meetings for that sort of thing. A healthy organization will have meetings where we talk numbers and we talk about sales and we talk about engineering tasks. But those aren’t the one-on-ones between leaders. The one-on-ones between leaders really need to be about the health and performance of that leader, and how they can really help each other.

So, really, a good CEO, frankly, would be spending a bunch of their time, typically alone or in some sort of quiet area, an hour a day or some amount of time a week, where they’re really just strategizing and planning and reflecting, and prioritizing their own mind. And then the rest of the time, basically going from one leader to another in a circle and making sure everybody is ok and making sure that those leaders have the CEO’s full attention and support for whatever they’re trying to accomplish. So that’s, I think, the best way that they can fix it.

Tim Butara: It’s kind of like a workout, right? You have to have the days when you do it, when you’re committed to it, you’re dedicated to it; and then intertwined with that, you have periods of rest – in this case, rest and reflection. Because obviously, the more people you talk to, the more stuff you have to mull over then once you’re in that meditation. It’s almost like, either you have to consciously mull it over, or you have to do it in a meditative setting where you subconsciously filter everything and analyze everything subconsciously.

Sam McAfee: Yeah. Or you can wake up at 3 o’clock in the morning thinking about it and not get a healthy night’s sleep, that’s the right option, right?

Tim Butara: I mean, but if you do it spontaneously, if you do it naturally, then I guess you’re still in that state of flow. So, yeah, it’s annoying, it can suck, but sometimes, the best work gets done at 3 am when you can’t sleep, so, it’s that tradeoff.

Sam McAfee: I’m glad that you brought up that point about the volume of things to think about, too. Because if you think about typical executive teams, six, eight people, depending on how many departments, functions there are. And if you’re having a one-hour long or longer one-on-one with each of those people once a week, there’s a lot of material that gets generated in that discussion. And a lot of things that have to be thought about. You can’t decide everything in that conversation. You might say, hey Bob, or Sally, that’s a great thing, let me think about this for a week, let’s talk about it in our next one-on-one. And then you’re carrying that around in your brain and have to do something with it.

So, I think just the sheer cognitive load of being a leader is something that folks who haven’t had that experience yet in their career, let’s say like engineers or engineering managers who’ve never been a CEO – they can’t quite appreciate how much brainwork is required to run an organization. It’s an extraordinarily difficult task.

And so, I think we all could do with having a little more empathy for our leaders who are under a lot of pressure from the market, from the board, from down sales numbers – especially right now, we’re in a particularly tricky spot in the tech sector. Everybody’s feeling under a lot of pressure.

The most important thing for us as individual humans in an organization is to have as much empathy for each other as possible. And to try to not point fingers and attack each other in meetings, and let our tempers get the best of us. But really try to move forward with some degree of empathy and put our problem-solving brains together and try to figure out how to pull the company through a difficult time like this.

Tim Butara: So, empathy is definitely one priority for leaders, basically on any– you spoke about the three different layers initially, basically on any of these three layers empathy should be a priority because of the looming recession. We’re recording this on the heels of some banks collapsing and whatnot.

Sam McAfee: Yeah, it’s been an exciting weekend.

Tim Butara: I mean, I’m not even following everything, because I feel like, if I follow stuff too much, I’ll just get stressed out and nervous about stuff that I can’t do anything about. But, to tie things back to our discussion; so, empathy is key here. Are there any other important changes that leaders should make here to navigate through all this more successfully?

Sam McAfee: Yeah, definitely. The work that we do at Startup Patterns is really rooted around the concept of mindful leadership. And mindfulness is becoming more of a popular concept these days. It doesn’t have to mean sitting on a mountain in an ashram in a monk’s robe. It doesn’t have to mean very esoteric, spiritual concepts – although, there are those as well.

I think what it really means is being psychically or cognitively present with what you’re doing in the moment at any given time. So, being aware of your thoughts, being aware of your feelings, being aware of your body and how your body is responding to those feelings.

So, if you think about it, maybe there’s two different conversations going on in your brain. You know, the running monologue we all have in our minds as we’re thinking about, listening to someone having a conversation, thinking about what they’re saying, thinking about what you’re going to say next, remembering that you had an appointment, remembering what you had for breakfast that morning. There’s that stream of consciousness, all humans have it. It’s called the default mode network, for those neuroscience buffs.

And then there’s a second layer, where we have the ability to actually observe that train of thought at the same time. So, there’s sort of a second layer where you can literally – I shouldn’t say literally; you can, in your mind, take a step back and observe your own thought and emotional patterns.

And it takes practice, but what ends up happening is, when you’re doing that, you become really present to what’s going on. And it allows you to slow things down and to respond to your colleagues or to a difficult situation with a lot more thoughtfulness and care. You know, most of the time, people are running around on autopilot, just reacting to things that are coming at them. And I think that, to the extent that we can practice a little more mindfulness, of slowing things down– one of my colleagues likes to say, create a space between stimulus and response. Just one breath between those two can make a huge difference.

Somebody in a meeting says something that sounds really bad or makes you upset, instead of responding right away from the first thing that comes to mind – taking a deep breath, takes maybe like four seconds, that can make a huge difference, because it gives your brain, your prefrontal cortex a chance to catch up with what was just said and process it a little bit and be aware of your own elevated heart rate or emotional response, and think a little bit more carefully about how you’re going to respond.

So, I think that that level of mindfulness is really important. And we’ve got to break it down into three different categories. The first one is really about being aware of yourself – and that’s all the stuff I’ve just been describing, just taking time to think about, just observe your own thought process and your own emotional responses to things.

The second is being aware of others. So, when you’re in a dialog with someone, if you’re in a difficult meeting, or in a difficult conversation, not only should you be aware of your own internal thought process, but also really actively listening and carefully observing how the other person is responding.

And that’s where the empathy part comes in, right. It’s really trying to see them as a person, and assume the best intent. Unless you have clear evidence that they’re trying to get you. But usually, it’s a misunderstanding. You know, nine times out of ten, people aren’t running around with malicious intent, we just happen to be paranoid creatures and we assume that trying to screw up our day.

But if you actually approach them with empathy and curiosity and say, hey, this thing that you said, that really threw me off. I’m sure you didn’t intend to make me upset. But could you explain a little bit more about what you meant there? Because I’m not sure I’m on the same page. And that kind of dialog can really bring more solutions into the situation, and it can also create a lot more better relationships and bonding between people who are at work.

And then the third category, if you think of these as nodes in the graph, the first node, yourself, is like one dot. And then thinking about others is like the connection between two nodes. Now you’re going to think about the whole graph, the whole organization, all the different relationships in an organization.

That’s the third category, is thinking about the company as a group of people that all have different relationships with each other. There’s certainly the org chart that tends to be hierarchical, but that’s not the only way of looking at the graph of people in an organization. There are lots of non-hierarchical relationships, people who have different levels of influence over others.

And so you want to look at the whole organization. Because what we think about is leading with influence, is thinking about how can you build relationships one on one with all these people so that you can start to build consensus and alignment about what’s going to be important and healthy for the organization.

So, it’s this three-layered– we call them the three pillars of mindful leadership, is that self, the relationship with others, or having good communication skills, and then leading with influence, being able to take the organization to a tipping point, where everyone’s on the same page or enough people are on the same page that they can act with one purpose and make the kind of changes that you want to make in an organization.

Tim Butara: And they all tie together and intertwine, right? I mean, you can’t really communicate effectively without empathy, and you can’t really influence effectively without effective communication. So, by consequence, you can’t influence effectively without empathy.

And that includes empathy– because, empathy, that kind of includes, if we expand it a bit to what you said, it’s having a keen understanding and a keen awareness of both yourself and others. Empathy is usually not something that we think about when we think about in the intrapersonal context, right, it’s more something interpersonal. So, that’s really interesting. We’ve kind of gone full circle, uncovering the true, the key tenets and the key factors that drive leadership alignment in organizations – and, I guess, alignment in society and in interpersonal non-business relationships as well, right?

Sam McAfee: Yeah, I think you raised a really important point about having empathy also for yourself. I coach leaders, I do a lot of coaching work, so I have a lot of conversations with folks who are in positions of responsibility and authority, and have a lot of weight on their shoulders.

And there’s often a lot of giving themselves a hard time. Really beating themselves up for mistakes and feeling inadequate. Sometimes we talk about the idea of impostor syndrome, which is a concept that’s been going around. The antidote to impostor syndrome really is having empathy for yourself.

There’s a way in which you can give yourself a break, forgive yourself for past experiences that you feel bad about. And the reason why that’s so important is that anyone who’s in a leadership position that is running around with a negative self image is often going to be fairly unconscious about it, they’re going to be not really mindful. And they’re going to end up taking it out on other people. It’s going to come out in their activity. Because, you know, that’s how it gets you. Having that low self esteem or negative self image ends up backfiring in our personal relationships.

So, it really is important to also have empathy for yourself as well as other people. And I find that leaders often are on a continuum of, some of them are extremely confident and feel really good about themselves, but they lack the skills of being empathetic with others. And just like that’s sort of the way their personality type is. And it’s not a lost cause. There are ways that they can develop those empathetic skills. It’s a little bit more mechanical for them; they have to practice tactics to sort of express empathy.

And then, on the other side of the spectrum, you’ll have people who are extremely empathetic to others, but don’t have as much of a strong internal sense of self. And their problems are sort of the opposite. Typically, they don’t have very strong boundaries. And so they will end up being taken advantage of, because in their empathy, they’re trying to help make everyone else feel better, but then they don’t really protect themselves, they don’t protect their own time, their calendar. They’re doing too many favors for too many people. And what ends up happening is they get burnt out and they feel resentful, and then they lash out, right.

So there can be lashing out if you’re on either end of the spectrum. And really the best thing is to find your way to the middle, right. You want to both be empathetic for yourself and take enough time to take vacations, take breaks, take time in your day for yourself, nutrition and exercise and sleep and all that. But also, be available for others as needed, so that you have both sides of the spectrum.

Tim Butara: I think, Sam, this was the perfect way to end the conversation. I think we just went full circle. I love that we ended up in very much psychological, not just advice, not just for leaders, but for any kind of person, right. Just be more mindful, be more empathetic, work on your relationships. I love it, Sam. If people listening right now would like to learn more about you or learn more about your book, where can they do that?

Sam McAfee: Sure. There’s two main places on the internet where I hang out. I’m a big LinkedIn user. And so people can find me very easily on LinkedIn, you just search for Sam McAfee or Startup Patterns. And I encourage LinkedIn connections, I like to chat with people there and help share content and solve problems. And I’m often writing and posting things there. So, finding me on LinkedIn is number one.

And then we do have a great website,, that talks about the work that we do and also has a really great blog with our articles of our different approaches to these problems; a lot of the stuff that I talked about, if you want to read more about it. It’s all over our blog. You can sign up for our newsletter and get an email from us about once a month with a new article. So those are kind of the two best ways for people to get in touch.

Tim Butara: Awesome. Sam, well, thanks again, thanks for a great discussion, and have an awesome day.

Sam McAfee: Thank you for having me, it was real fun.

Tim Butara: Well, to our listeners, that’s all for this episode. Have a great day, everyone, and stay safe.

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