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Anthony Taylor On Strategic Planning

By Anthony Taylor - February 07, 2024


Strategic planning goes beyond storing binders on shelves; it involves transforming intricate visions into concise one-pagers, harmonizing perspectives, and mastering effective communication strategies. Anthony Taylor, the founder of SME Strategy, is not a typical strategist. He is tough but caring, and he pushes your team to do their best. Today, he sits with us to discuss all about strategic planning. Anthony debunks myths that confine the concept to boardrooms and dusty binders. He explains a five-step method to simplify strategy, emphasizes the importance of celebrating success, guides us through the entire strategic journey, and more. Tune in now and transform your approach to strategy!

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SME Strategy is a management consulting firm that specializes in helping organizations develop and implement their strategic plans. We work with teams to facilitate conversations about strategic direction and business strategy so that our clients can focus their energy on what will move them forward faster.


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Listen to the podcast here


Anthony Taylor On Strategic Planning

Guest Spot From The Your Intended Message Podcast

I'm excited to share a special episode with you. I was interviewed on the Your Intended Message Podcast and there's so much good insight. It's from me but I'm excited to share it with you. With permission from George Torok, I said, “Can I put this on our show because I think our audience is interested in some of the practical things around strategic planning?” You get to tune in to me as your special guest on the Your Intended Message Podcast. I hope you like it and it adds a lot of value to you. Enjoy.


Strategy and Leadership Podcast | Anthony Taylor | Strategic Planning


In this episode, my guest is Anthony Taylor. Here are three facts that you should know about him. 1) He is the CEO of SME Strategy, which was founded in 2011. 2) His strategy blog has 25,000 readers a month. That's a lot of readers. 3) He was born and raised in Vancouver, BC. He has a lifelong goal of receiving the Order of Canada, which I believe is the most prestigious nonmilitary award in Canada. Anthony Taylor, welcome to the show.

Thank you, George. I’m happy to be here. It’s great to chat with everybody and looking forward to it.

I’m delighted to be talking with you. In case people haven't guessed, part of the discussion at least is going to be around strategy and in particular, what you do. You help companies, small, medium, to large enterprises, develop their strategy. You do that through facilitation. Let's take a look at that facilitation process because a lot of business leaders get it wrong. They might think, “I'll facilitate a meeting, ask some questions, and then tell people when they're right and wrong.” Tell us some of the well-intentioned mistakes that you've seen business leaders make when they want to lead a strategy facilitation meeting.

First of all, thank you again for having me. When we look at strategic planning, we focus on alignment, making sure that teams, people, and culture are all on the same page. With this being the Your Intended Message Podcast, it's interesting because people assume that they are aligned but when they're communicating, their message isn't exactly making it across as intended. Largely it's because there's misalignment. There are different priorities, ideas of what success looks like, too many priorities, and different assumptions in terms of information.

As a leader or a facilitator going into a process where you're trying to come out with a clear vision, mission, values, priorities, goals, and actions, alignment is the number one key to making sure that the next part of the process can be successful. It is a scaffolding. It's about testing assumptions with people and moving from implied to explicit so that teams can ultimately make sure that they're working on the same thing.

The last thing I'll say is we call that Escaping the Multiple Destination Trap, where you're stuck. Everybody's spinning around in circles. There's not a lot of progress. Everybody's working on different things to what we call one destination. We use a one-destination model, which is aligned with vision, mission, values, priorities, goals, and actions. Whether a for-profit or not-for-profit mission-based organization can get as much done as they'd like.

Sometimes when you get a group of peers together, they're in the meeting to see what they can get for their department. They’re like, “I don't care what anybody else gets. How do I win?” How do you get them out of that mindset? That's an easy mindset to fall into.

The biggest thing we say is, “What hat are you wearing?” It is the question we'll ask. I'm a sports guy and you asked about my crest. I was a Basketball Hall of Fame. Using a sports metaphor, the name on the front of your jersey is more important than the name on the back. Are you thinking about your company or organization, or are you thinking about your function?


The name on the front of your jersey is more important than the name on the back.


One of the breakthroughs that we help teams get is when they can think about the organization first and themselves second, then it breaks down some of those barriers and friction pieces and recognizes that it's more collaborative than competitive. A lot of times, people walk in with a competitive nature, being able to reframe that for everybody to say, “We're on a team. We need to work together. We won't get where we want to go if I'm right, you're right, and we both lose. We need to be able to work together to move towards a common goal.” Reframing what a team means is critical.

I appreciate you calling it a team because some people like to call themselves a family. That's yucky because we work together. We're not family.

I joked that some people don't like their families. I interviewed somebody on my show who said he worked for Netflix and Zappos but in reverse order. Zappos had a culture of family and Netflix was entirely the opposite. They called themselves a professional team. It's so interesting how cultures can be different and certain cultures foster that. If you like that, you'll gravitate to that culture and flourish. If you don't like that, you'll find it yucky to your point and you're better suited in a different organization. That's why culture as part of strategy is so critical. The audience might have heard, “Culture eats strategy for breakfast,” which I believe is firmly true.

I'm wondering, before we can even get into strategy, is it important to clarify what we believe the culture is and is not?

Do we need to clarify it before we do strategy? The way we look at it is that your culture supports the attainment of a vision. Depending on where you want to go, the how will change. There's a point in Alice in Wonderland that I reference often where there are two forks in the road. She asked the Cheshire cat, “Which road should I take?” He says, “Where are you trying to get to?” She says, “I don't know.” He says, “Any road will get you there.”

The way we do it is we focus on first, where we are, and next, where we want to go, making sure that we're all on the same page in terms of where we want to go. We then work backward. If your ideal future is this warm, fuzzy, and nice working environment, then the culture and behaviors that you want to foster are likely some things around friendliness, warmth, compassion, and empathy.

I'll try to create an opposite. If your successful future is super profitable, cutthroat, winning, and a zero-sum game, then you might have values and behaviors like personal development, giving it 110%, and winning at all costs with determination. Those things can coexist in the right environment but looked at separately, they are night and day. Depending on your future, the culture will adapt to that.

Let's say you are called in to work with a medium-sized company to help them develop their strategic plan. Here’s my first question. Do we develop a plan for 1 year, 5 years, or 10 years?

The way we look at it is typically three years. A lot of organizations have done five-year plans in the past. The way we see it is there are two problems with it. One is that there's so much change that by the time you get to 2 or 3 years in your plan, the environment has changed so you're stuck to it. The other challenge that we've seen is that most people don't have five years' worth of strategic foresight. It’s as if they don't have the skill of being able to look that far into the future. It gets too fuzzy. Why we look at three years is it's a nice balance between long-term aspirational and short-term implementation.

If you think of a couple of years back during the pandemic, people could barely plan 1 week or 2 out ahead. How could you look that far? There are certain instances where you want to build a one-year plan. It's more operational than anything else. If you're a small business that has a lot of volatility, the shorter timeline makes sense but for us, three years is a pretty good catch-all for most companies South of even $300 million or $400 million. Even a $1 billion company that we work with, they have a 3-year plan that's stretched out to 4 years to align with their existing planning.

Typically, a startup doesn't have a three-year plan. They've got a next month plan.

What's interesting is I am personally in the middle of a twenty-year plan. Order of Canada is part of my plan. Also, creating this business and doing everything I wanted to do. When I was in high school, I said, “What pays the most amount of money?” A bartender becomes paid the most so I became a bartender. “What gets paid most per hour?” It’s a consultant so I became a consultant. I wanted to travel the world and all of that stuff happened. Small businesses, yes. Even for our company, we're at a two-year plan. It depends on your lens and what's your intention. What's your intended message to yourself? How do you continue moving that along?

Is a strategic plan mainly about direction and values as opposed to steps and procedures?

I'll say it's more of an and, but one of the biggest challenges that I see with entrepreneurial, fast-moving, and ambitious organizations is they ready, fire, and aim, if you ever heard that expression. They're so focused on the actions that they sometimes forget, “Are they the right actions? Are we clear on what the results that we're trying to get?” The other challenge that we see, and this is largely with mission-based organizations or nonprofits, is they have limited resources.

They don't have enough time, money, people, and focus so they can't afford to make mistakes. I don't think anybody can afford to make mistakes but them more so. The strategy piece of it is about making the right choices. When we put in the vision, mission, values, and priorities, those are all filters to help ensure or support the right decisions being made at scale. To build on that, if you look at a small business, it's 1, 2, or 3 people. The locus of control is very short. I make a decision so I'm responsible for it.

As you get to 10 or 20 people, which is the typical growth path, then there are more people that you need to guide and direct. There are people who are doing tasks that aren't necessarily responsible for deciding the tasks or the direction. You get an exponential order of magnitude as you get to 50, 100, 200, 500, and 1,000 people. The strategic plan is put in place so that it supports the right decisions being made on any given day.

With a 30,000-foot vision on the ground execution, yes, there are a lot of tasks but you could do a lot of stuff and make no progress. You need that vision to say, “Are we doing the things that are moving us in the right direction?” It's a balance of both but if your strategic plan is an Excel sheet of 150 tasks, it's not strategic. If all you have is a broad and vague vision and mission, then you don't have an actionable plan. Creating that balance between the two, that's both visionary and ambitious, but executable and practical, is where the fit is. That's what we, as a company, do well.

There are three terms that you've mentioned a few times and I want to highlight them. You mentioned vision, mission, and values. Is that where it starts?

It's all a matter of context, George. It starts where you are. I'll call it pieces of pushback that we get sometimes and not in a negative way. People want to get right into the doing. One of the things that we encourage people to look at is, “How did you get to where you are? What are the successes that led you to that point?” We start every strategy session with a celebrate. People try to jump naturally because of human beings. The way we think is, “What do we fix? What's next?” We never take time to celebrate the successes and look backward.

We also take the time to do a SWOT analysis, which a lot of people are like, “I know this from business school. I've done it.” The point of it is so that you and your team can get on the same page in terms of your strengths, weaknesses, opportunities, and threats so that we all have the same perspective. If we don't have the same perspective, we're going to have different interpretations of different information. Your intended message is not going to make it across.

I hope you don't mind me referencing it. It's just your intended message is such a critical part of all things communication. That is one of the biggest challenges with teams. If you're not on the same page, not talking the same talk, and not seeing the same things, you're going to have a different problem. Does it start with vision, mission, and values? No. That's where it ends but it's part of the process. You're either getting to your vision or you don't. You're either doing your mission or you're not. You're either living your values or you're not. Everything else is building a structure to help you get there.

You said it starts with where you are. Where are we in terms of our development, the market, and the culture we have with our people? Where are we in terms of what we think the future might look like? I can see that map at the mall. You are here.

Maybe I'll explain the five steps we do it. I’m a pretty simple guy. We decided this to be simple. You don't need to be an MBA to understand it. All of the SMEs that we work with are incredibly intelligent but not everybody's got a business school degree. Some people worked up the ranks and became successful in their organizations. We made five steps. I could break them down but here are the five steps. Where are we, which includes the SWOT part, the celebrate part, and what's happening in the world around us? All of those things are critical.

Where are you going? That includes the vision and mission. What's going to get in our way? If we know where we are and where we want to get to, what's that unknown middle that we want to focus on so that we can prioritize? What do we need to do? Where do we need to focus? We look at 3 priority areas instead of 7 or 8. We say, “Where do we need to focus? What do we need to do to bridge the gap between where we are and where we want to get to?”

The last one is how we are going to implement it. We spend a decent amount of time talking, not just about the plan but the structure of driving the plan forward. That means, how are we going to communicate it? How are we going to roll it out? How do we make sure that everybody else gets our intended message in the company? How do we stay on top of it?

How do we hold each other accountable? How do we track and monitor? What is all this stuff? The thing I tell every one of my clients is there are typically two days of planning. We do two-day offsites. It’s 2 days of planning, 3 days of planning, and 1,100 days of implementation. Most people overresource the alignment or strategy and underresource the implementation. I resource them appropriately.

1,100 days of implementation so that's your 3 years. That 2 days of planning and 1,100 days of implementing is doing and continuing to communicate along the way.

I challenge most people because we usually deal with senior executives or boards of directors. I say, “How much of your time is spent communicating?” Invariably, when they think, “What do you mean by communicating?” “Assuming you're not in it, how much of your time is it?” I'm talking senior leaders here and they're like, “All of it.” I'm like, “Probably between 80% and 100% of your time is spent communicating. If you want the biggest and highest opportunity for improvement, become a better communicator. Focus on your communication, not just the message but the whole system and structure.”


Strategy and Leadership Podcast | Anthony Taylor | Strategic Planning


You could say, “I sent that person an email.” I'm like, “Did you send them an email or did they get the message?” “I called them.” “Did you need to call them twice? Maybe you needed to knock by their houses or send them a text message.” It's not just the what but the why of communication. Communicating top down, getting communication bottom up, and across is critical for teams to move their plan forward. That's the highway of information.

HBR did a study and they said, “What are the straights that correlate with strong strategy execution?” They surveyed 26,000 people at 30 companies. There was a bunch of them but the top two categories were information flows and decision rights. Do the people get the information they need about the competitive environment or the internal environment when they need it? Do people know what their roles and responsibilities are within the plan? All of that is communication.

Of the top 5, 4 of them fell within those 2 categories and the list goes on. People get so focused on their competitors and everything outside. No, it's in your four walls that you need to make sure that your systems and structures are in place to help your team be successful. Managers jobs are to provide support and direction for all of their employees. When they go through this planning process, they create something that they think looks good. It's all shiny. It's inspirational.

I said, “If your team were to read this, would they understand what it meant? Would they be able to be explicit and clear about what success looks like?” They get so lost in reading this document that they put their heart, time, and marketing speak on it. They say, “Is the intended message making it to them?” They know what they need to do to move the plan forward. If not, don't make it so complex. Keep it simple. That is what a strategic plan is for. It guides people to make sure that they know the right decisions so that as leaders, they can be more effective in terms of how they communicate, where they want to go, and what they need to focus on.

The strategic plan in writing, does it look like a set of 4-inch binders or is it a 2-page document?

If you can get it to a 2-page document, we even have it as a 1-page but not a binder unless there's a good reason for it. We have it as a one-page with vision, mission, values, and strategic priorities. Within the strategic priorities, you need to have measures that would accompany a second page. Does your team know what good looks like? Do they know what the rules are? Do they know what the score is? If you don't have a score, you can't win so you need goals. If you don't know the rules, then you'll get frustrated. That's your values. If you don't know what good looks like, you'll get frustrated. That's vision. Keep it simple. That's all you need.

What good looks like, what the rules are, and what the score is are a whole lot easier to understand than vision, mission, and values, which get thrown around so much and posted on company walls that no one ever understands.

We wanted to make strategy easy. You didn't have to spend money with a Big 4 consultant. You just need a structure in place and we wanted to make it approachable. What’s cool about the work that you and I both do is the impact that we can have on people. It makes the difference between a CEO and their family, community, and all that stuff. I view strategic planning as a way of changing the world. If a company has a good workplace, it means the employees are happy.

If the employees are happy, their families are happy. If their families are happy, the community is happy. If the community is good, then that makes the world better. Strategic planning is my way of changing the world. Let's bring it back to the Order of Canada, which I never talk about. I appreciate you asking that personal question. No one ever knows about that. Most of the time, I tell people that I want to go to 30 major league baseball stadiums and I'm at 17 or something like that.

There is the mission. Now, I know what good looks like.

You need to have it. Otherwise, if you don't know what good looks like, how will you ever get there?


Strategy and Leadership Podcast | Anthony Taylor | Strategic Planning


I'm looking at that and I wrote it down here, “Good rules and score.” That's someone that a team leader probably should look at every day.

I don't know how to make it more simple. There are a couple of speakers that I've heard. They talk about the idea of a one degree shift. I'm not going to attribute it because I've heard it in a couple of different places. One degree shift and improvement over time can send you on a significantly improved trajectory. How I've heard it referenced in the past is let's say you're on an ocean and misaligned one degree. I use a hand analogy. Your fingers look aligned here if you go straight but if you're this, over time, the distance between your fingers gets further and further apart.

Why a strategic plan is not a binder or something that gets looked at once every three years or once a year is because the opportunity and likelihood that you and your team are going to get out of alignment increases significantly if you're not having the conversations for real alignment. That's why our clients both have us facilitate their strategic plans to start it. We then come back in monthly, quarterly, and yearly to keep them focused and accountable to the plan so that it gets done versus a binder that sits on a shelf.


The opportunity and likelihood that you and your team are going to get out of alignment increases significantly if you're not having the conversations for realignment.


I've seen many strategic plans sitting in a binder on a shelf that even the manager who gestures over at that binder every once in a while doesn't know what's in there anymore. How can the team know it?

It's one of those funny things in addition to the binder. When you have CEOs whose job it is to be 2 or 3 steps ahead, which is fine, they forget that their teams can't read their minds so they'll communicate something and be like, “How did you get from here to there? Walk me back,” but they never do. They do the opposite. They keep pushing forward and sometimes leave the people behind.

The other thing I see is that a person will make a decision and that same person will forget that that was the decision they made. They'll go back on it. It brings teams swirling around. Documenting it and putting everything in a process, system, or structure helps everybody stay on the same page and aligned. It allows the CEO to move forward and be visionary but also supports the people whose job it is to implement the plan and take action to bridge that gap. To help teams work together and communicate, make sure they know what's up.

Part of the CEO’s role and responsibility is to be thinking 2 or 3 steps ahead, which means that the rest of the team is not necessarily thinking the same way. How does the CEO check in with the team to see if what they're seeing 2 or 3 steps ahead makes sense?

I believe that part of every senior manager or leadership team member's role is to look forward. The issue that happens is that I'm looking forward at a thing and you're looking forward at a thing. If you're a marketing leader and I'm a finance leader, sales leader, and operations leader, our forward-looking is we all have different vantages. The CEO's job is to let those people lead their respective vantage but has to take into consider all of those perspectives to create one cohesive picture.

That's why we use the analogy of a puzzle. If you're building a puzzle, you need to know the picture on the front of the boxes. If you don't have that picture on the front of the box, then A) You're not going to know where the pieces go, and B) You're going to have a lot more of a frustrating experience where everybody is fighting for their pieces and saying, “No, mine goes there.” That's stuck in that multiple destination trap because there's no one clear picture versus being aligned towards one destination.


If you're building a puzzle, you need to know what the picture on the front of the box is. If you don’t, then you're not going to know where the piece is going.


The CEO's job is to hear everyone's perspectives, bring his, her, or their perspective into the issue, and then say, “Where do we all go?” It's not about agreement because you're never going to agree on everything. That's why having a facilitator like myself or the folks on my team helps because we can pull out those various perspectives so that people can hear each other and make sure that their messages are landing and that we can get aligned. You'll never agree on everything but as long as you can get aligned as a team and we're all going to the same place, it helps everything downstream move forward.

When you come in as a facilitator, is part of your role to ask the questions that no one else is willing to ask?

A hundred percent. I consider myself a loving jerk because I do care about the people that I work with and I wouldn't say too much. I'm just an empathetic feeling person but I also will ask questions to challenge, probe, poke, and irritate because a lot of teams are too nice. Distinct from kind, they don't want to have conflict because in North American cultures, typically, conflict is viewed as bad. Whereas in Middle Eastern or European cultures, conflict is good.

Sometimes we avoid tough conversations because it is uncomfortable or they might be seen as not nice or full of conflict. My job is to create productive and effective conflict versus starting problems. The benefit of being an outsider is that I have not only the opportunity but I'm requested to challenge assumptions, test beliefs, test knowns, and help reframe what people think differently about certain issues. What's most important is not 1 senior executive or 2 being right. We've got thousands of employees that depend on us.

What's more important, you or their perspective, the thousand employees that count on us for their financial well-being, or the tens of thousands of people that we serve in our community because we're a mental health organization? I'm sure you can put your ego aside because we have something way bigger than us. What's neat about the work that we do is the broad-reaching and cross-sectoral impact of changing the world.

Part of your role is wielding and mastering conflict as a productive tool. You get to leave so it's not like you have to say, “He's never going to buy me a coffee again.”

I'm giving away all my good facilitation tricks here. Sometimes, I'll leave the room and say, “I don't care what you guys do. It's your plan. It's not mine but I'm here for it.” One of the things that is distinct from causing problems and leaving is the output is greater trust. If we can work through a strategic planning process, team development, management, and leadership training, and work on the building blocks that create a strong environment for the team, and typically, that's trust and psychological safety, then the team is equipped to have those more challenging questions down the road.

We want to teach them to fish versus just fish for them. That's why we're not consultants. We don't tell them what to do. A critical piece for us is to be able to build that trust in a team and help them be successful ongoingly. Part of doing that is being able to walk into a room where sometimes people are feeling like, “Them and I are so far on the other end of the spectrum. We see things night and day.” Often, those are assumptions, thoughts, or beliefs.

When we go through the process of what success looks like, and I get this all the time when we do a survey through our conversations, they say, “We're more aligned than we thought we were.” I don't know if crazy is the right word but it is how powerful the human brain is to trick us into the negative, whereas when a facilitator can come in and check for realignment, test the assumptions, and challenge the beliefs, people leave the room being like, “We're way more on a team.”

I was viewing it from this perspective and it looked a 6, and you were viewing it from the other perspective and it looked a 9. Once we can see each other's perspective, we realize that we're both right. Both of us can coexist in being right at the same time. It's a lot of strategy work but also a lot of behavioral psychology and organizational behavior, which doesn't exactly show up on the name plaque but that's what makes us different.

For those who would like to know more about Anthony and the services of his company, you can find his website. It is SMEStrategy.net. Anthony, as we prepare to wrap up, say you could sit down with a business leader who's planning to have a “How Are We Doing” type of meeting. We put together the strategy and it's time for him or her to get together with their team. If you could give them 1, 2, or 3 pieces of advice going into this meeting to make it more effective, checking in, “How are we doing,” what pieces of advice would you offer?

Before I do, I want to say thank you for having me on your show. It's been super fun. I love this conversation. This is for leaders who are about to get into a “How We're Doing” meeting and a couple of best practices. 1) Focus on creating a safe space with your team. When we say safe, we can't say necessarily psychologically safe. We try to talk about accountability but have the intention clear. We're trying to focus on the process versus the people.

If you can separate the individuals from the outcomes and say, “The purpose is to look at the outcome. I'll give you the agenda. What did we do well and what didn't we do well?” Focus not on who did it or who didn't do it. Look as a company. You'll have everybody more willing to discuss criticism, challenges, and that kind of thing. Focus on process versus people.


As a company, you'll have everybody more willing to discuss criticism and challenges, so focus on the process versus people.


2) Create the framework for, “Why are we doing this?” “We're doing this review so that we can move forward to that next level.” If everybody is clear about what the next level is, then they'll recognize what's at stake for doing the review. A different way to reframe it is the work that we put in is a function of our goals. If we have small goals. We have to do less work for it. It's less challenging. If we have big, ambitious goals, then we need to do big, ambitious work to get there. It helps you overcome those challenges. 1) Process and people. 2) Have something big at stake.

If there's a third one, make it fun. The team has got to be out. Sometimes, it's stressful to be out of work. It's psychologically heavy work. Make it enjoyable. Say, “We love our jobs. We like the work we do.” Hopefully, you like your job. Say, “Let's enjoy.” It doesn't need to be doom and gloom. We'll take the opportunity to celebrate all of the good things that happened in the year. You'll say, “We accomplished more than we thought.”

Most people focus on the negative versus looking at, “The only reason we have this much negative bad stuff or as much stuff we didn't do is because we did so much to build the next level that's more challenging.” That's just levels. If you can get your team to do that and focus on continual improvement, focus on the process, and have something big at stake, you'll have a great meeting and your team will be even more aligned than before.

My guest is Anthony Taylor, reminding you that the name on the front of the jersey is more important than the name on the back of your jersey.


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