 I was asked recently how you teach strategic thinking. The actual ask went something like this: “You’re a good strategic thinker. How do you do it? And, how do you get others to think like you do?”
To be clear, I’ve taught a lot of things, but never this topic specifically. So, I thought it was a great prompt to think more about my thinking and my practices – which I admittedly don’t always understand. And, I’m sure some of these are solidly based on proper strategic thinking frameworks I don’t know about, or have read about and forgot I read about them. I do know they are all rooted in how I learned to think and work as an artist, an organizer, and an entrepreneur. So, here are my 10 tips for getting more strategic in your thinking: 1. Look two steps ahead and one step behind. - Two steps ahead: Where could this go? What are the possibilities? What are the probabilities? What are the pitfalls? What are the next questions that will arise as a result? What are the next challenges it will expose? - One step behind: How did we get here? To the current state? To the current mindset? To the current decision? What is guiding our thinking today? And, back to two steps ahead: is this what should be guiding our thinking into the future? 2. Define your assumptions (so you can keep testing them). This is our business. This is our ideal customer. This is our value proposition. These are our markets. These are our products and services. These are our points of difference. I’ve worked with hundreds of team members from the executive level to the frontline, and it’s rare they can confidently define these much less do so in full alignment with each other. 3. Be strategic about what your being strategic about. We can think strategically all day about how to solve a problem or seize an opportunity but if that’s not the right strategic problem or opportunity then we are still not being strategic. We must distinguish between presenting problems and latent problems, today problems and not-today problems, opportunities and the right opportunities. 4. Align on “The Why”. If you, your team, and any other stakeholders aren’t aligned on “the why” of whatever it is you are doing, then when it gets hard, things are going to fracture. Back to #2, we must not assume alignment. We should do the work to put “the why” into words so that it can consistently be shared across stakeholders and over time and not morph as a function of memory or interpretation. 5. Align on why. “The Why” is about purpose. Aligning on why is about rationale. Why is this the right move? The right direction? The right investment? The right time? The right team? A good idea is only good in as much as you can provide these answers and convey them to others. 6. Treat everything as a tradeoff. Every choice we make to do something is an implicit choice of what we won’t do. We must discuss and make decisions based on both sides. 7. Assume you are wrong. Assume they are wrong. But, be nice about it. It is the opposite of strategic thinking to assume we have it all figured out, we’ve asked all the right questions, and we have all the right data. Poke holes in everything as a matter of strategic process, not judgment. 8. Stop nodding in agreement at blur words and vague ideas. I mean, strategy…who disagrees we should be strategic? Everyone nods for respect and teamwork and synergy. I don’t know what any of those mean to you and certainly not to your business. Be wary of too much agreement when you haven’t even made sure you agree on what you’re talking about. 9. Focus on the system. What part of the system are we not thinking or talking about? What are we missing? What stakeholders have we not aligned? How does energy, investment, effort, and/or required skill shift within the system if we go this way or that? A system with one underperforming part is an underperforming system. A strategy with one underperforming part is an underperforming strategy. 10. Understand your starting point. Strategy doesn’t matter unless you have the people to execute it. Your teams will determine if your intended strategy becomes your delivered strategy. Be honest about who you have and if they are ready, or what it will take to get them ready. Strategy is useless without execution.
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 I sometimes get asked about the ROI on the work that I do. Whether I am talking about leadership, emotional intelligence, empathy, communication, trust, developing others, conflict management, or decision-making, it’s all a function of building relationships that build teams that connect with customers that build businesses.
So, let me flip it around a bit and pose the presumed, if underlying, question: what is the ROI on a relationship? How much is your spouse worth to you? Your kids? Your friends? Your neighbors? What’s the dollar amount you expect to get back from loving them, caring for them, cultivating them? What are they worth? What’s the return on investment for your time, energy, and effort in these people? Just asking these questions stirs a kind of queasy feeling. It feels almost perverse because we don’t look at these relationships as transactions, as quantifiable. Most of us do, however, look at them as the investments that create the most value in our lives, the most joy, the things that mean the most to us, that motivate us, give us purpose, connection, and belonging - and yet, they have no consistently defined return on investment. When you convert the potentially transformational into the transactional, the relational into the purely functional, you’re destroying value in the name of capturing it. At some point, we have to remember we are just humans working with other humans in human-created systems trying to serve other humans. We just call it a business. If you aren’t actively cultivating relationships because you can’t defend the cost, then good luck defending the cost of not cultivating them. I have not been a CEO, but I have been the #2 guy several times over – in nonprofits, in consulting, and in two tech startups. I like being the #2. I like enabling CEOs to thrive. I like playing up their strengths and helping manage or compensate for their weaknesses. I like bridging the vision of the CEO with the team who needs to execute it and customers who need to buy it. I find it a creative sweet spot for me. I have no interest in being a CEO.
So, I thought I’d share 5 things I’ve learned about being #1 by being #2: 1.There is no perfect CEO. Every CEO I’ve worked for has been different. A CEO is only as good as his/her match with the company: with its stage, its product or service, its customers, and/or its growth trajectory. Some CEOs are great in the messy early stages but struggle to operationalize the early creativity into a growing company. Some have great industry knowledge but don’t know what it’s like to build an early team or sell an incomplete or inadequate first product or service. Some are masters of business and process but struggle to adapt in the absence of the ideal. Some thrive on the energy of the business but lose the people in the process. Some thrive on the people and lose the business. So, a CEO’s success is often a function of their match with the business need and opportunity – and the right #2. 2.The glory isn’t worth the pain – unless you really are a CEO. Being a CEO sucks, unless you are really a CEO. It’s in your wiring. The time commitment, the burden, the responsibility, the relentlessness of the business, the personal and family sacrifices: these aren’t for everyone. I’ve seen the wear-and-tear first-hand and, because I was always #2, I often recognized it in my CEO before they fully saw it in themselves. Don’t get me wrong, the #2 has wear-and-tear too, but it’s different. The best CEOs aren’t CEOs because they wanted to be a CEO. They are a CEO because of something deeper. 3.The best CEOs recognize leadership is a team sport. I’ve been fortunate to work exclusively with CEO’s who believe this and believe it deeply. I suppose a CEO who didn’t believe it would never have hired a #2 like me. They welcomed someone who would challenge them. They welcomed someone who could step up and do what it takes in the moment regardless of complexity or audience or function. They welcomed someone who proactively took things off their plates. They welcomed someone who owned the vision with them, but knew how hard it is to be a CEO. They welcomed anyone who made them better and made the team better. 4.The best CEOs know their weaknesses and look out for their blind spots. You have to be supremely confident as a CEO but also know how to check your ego at the door. The CEO sets the tone and the standard for the rest of the company. So, a CEO who wants people to learn has to be willing to openly make mistakes. A CEO who wants his team to own the vision has to be willing to give all the credit for its realization. A CEO who wants a company that treats its customers well has to build a company that treats each other well. It’s far more effective for the CEO to show all the ways he’s not perfect than to create an illusion otherwise. 5.The best CEOs have the best #2’s. I am not saying I was the best #2 or that my CEO’s were necessarily the best. Rather, I believe the proof that you’re up to the task of being the CEO is that you are willing to hire someone as a CFO or COO or CHRO or otherwise who you trust and empower to lead the company with you. The role of the CEO is inherently lonely. Good CEO’s don’t double-down on that by making it about them but rather enlist true partners in the work.  A couple of years ago, I was working with a multi-billion dollar, global financial services company that had (pre-Covid) a vast network of on-location staff as well as remote online and call center staff to provide direct support to their customers. As we talked about growth and change in their company and their market, we explored if and how they were, or could be, learning from these front-line employees spread across the globe. What were these people hearing directly from customers that the company really needed to hear and understand?
We’ve all heard the saying about the importance of having “an ear to the ground” so we can sense imminent changes in our work environments and markets, but how well do we do it? Who has their ears to the ground more than those meeting our customers where they are? Dealing with their problems? Frustrations? Who has the potential to positively or negatively impact our customers minute-to-minute on a daily basis? Too many of the people on the front-lines of our work think they are too “low on the totem pole” to speak up in our companies or don’t have the power to create change in their own work. And, too many companies think the same way. As a result, many of us are really missing the opportunity to become more resilient, adaptable, and creative organizations. When we don’t listen to our customers and the employees who interact directly with them, we run the risk of missing indicators of emergent change in our markets, products, and even broader society that can lead our products and companies toward their next iteration. Through a simple, facilitated reflection process, this company - which thought it did a good job listening to its people because they could reel off some good anecdotes - realized that their listening to front-line employees across the organization was far spottier than they would like. They recognized that their anecdotes were about specific leaders or departments that carried this value of active listening rather than a reflection of a systemic approach or strategy by the firm. The implications from this kind of company self-awareness became pretty vast as they then considered who they needed to train, how they needed to adjust professional roles and expectations, and how a better process of listening could improve their product offerings. To cultivate a powerful culture, people at all levels of our companies need formal and informal outlets to provide feedback, ask questions, and share ideas and solutions. This is just strategically smart. It’s not about being nice to our employees. Not only will listening to our employees make our company more resilient and adaptive, it will also make for happier employees and better products and services for our customers. When they know their ideas and insights are respected (even if not always acted upon), our people will more actively and critically identify customer patterns and frequent issues that we may never see, and solve them in ways we may never have thought of. They will own their work and the whole company will perform better because of it. Powerful cultures don’t happen by accident. They result from powerful leaders, powerful relationships, and organizations that understand and leverage the power of their people at all levels. Also relevant: “Does your organization have a powerful culture or a culture of power?”  I wrapped up 2019 with a reflection on advice, and unwittingly found myself again reflecting on the topic as 2020 thankfully comes to a close. There must be something about this time of year!
Anyway, here are a few more thoughts on advice from 2020: 1. If a person starts with his advisement and not by listening to you, run. Run fast. He probably believes he is a great advisor or mentor because he knows so much and has so much to say. But, the great advisors and mentors are the best listeners and thinkers and question askers. It’s not what they know so much as how well they surface knowledge with you and within you. Advice should be arrived at collaboratively. 2. Listen to all advice in the context of that person’s experience. Advice is rarely directly transferable. You have to peel some layers back to get to the nugget unless that person has experienced the exact problem in the exact industry with the exact people and the exact business model as you. Clearly, you don’t dismiss them because of this discrepancy, otherwise you’d never find yourself a good advisor or mentor. But, you need to know where they are coming from to understand what they are saying - and, of course, understand where you are to know what to do with it. Advice is an act of translation. 3. You have no idea what you are doing, but you know what you are doing. This is a seemingly odd contradiction, but boils down to an obvious translation: you know some things, and you don’t know some things. Good advisors or mentors will never make you feel stupid for what you don’t know, nor will they ever let you feel like you have it all figured about because of what you do know. Their advice should uncover both, and leave you encouraged and humbled, motivated and uncertain. Advice should generate a sense of creative tension. 4. Gather all of the advice you can and throw away as much as you should. Advice is for learning and improvement along your journey. You are not, and should not be, beholden to it - although, you should be accountable nonetheless. So, if you take advice, you should know and be able to communicate exactly why you took it. If you don’t take advice, you should know and be able to communicate exactly why you didn’t. If you can explain and communicate the result in this way then you can show that you’ve listened and learned and gotten clarity out of whatever advice you have received - accepted or denied. A good advisor doesn’t expect you to take them at their word, but they should expect you to demonstrate that you listened, translated, and acted accordingly. Advice is a prompt, not a directive.  My commitment to creating has presented me with many media over the years - some art, some not - each of which has its own tools, challenges, and creative outcomes and brings its own unique joy and value to the world. Drawing. Painting. Printmaking. Sculpture. Digital media. Community organizing. Advocacy. Nonprofit management. Educational consulting. Entrepreneurship. Life itself. Several years ago, I even wrote a book about it. Last night, for the first time, my medium was flowers. Thanks to a company called Poppy, I had a box of fresh-cut, direct-from-the-farmer flowers delivered to my door to create with as I saw fit. I had big aspirations of enjoying the process with my two daughters (6 and 8), but the day kind of slipped away from us. So, as they wound down their somewhat hectic day, I actually had some time alone, some me-time, some "studio time" with this big, bunch of color, height, form, movement, rhythm, and rhyme in the medium of Poppy flowers. Part sculpture, part painting, part meditation - my first experience with flowers-as-medium was a treasured and peaceful and unexpected end to my day. And, this morning, the results met me at breakfast - presenting me again not only with the joy of the diverse beauty, color, form, and pure nature of the flowers - but also a moment of reflection and self-critique, seeing things in the new light of a new day, showing me how I could have done a better job arranging them. This is the creative journey that drives life - no matter your medium. Creating matters. Thanks, Poppy.     I’ve already learned a lot halfway through Techstars, but the clearest and most obvious is: if you want to test your startup, go have a 100 conversations about it. I don’t mean that abstractly. I mean 100 actual, focused conversations.
Go give your pitch 100 times and see if people get it. See what questions they ask. See what questions you start to ask yourself - as you stop focusing on crafting what you are saying so much that you can actually listen to yourself, and listen to them. Describe your product to someone who knows nothing about it. Describe it to someone who knows everything about it. Describe it to someone who is a user, knows a user, can’t imagine what it could possibly be used for. Describe your product 100 times. Describe your market to these same people. Describe your go-to-market. Describe all the things you know about how you are going to be successful 100 times and see at what conversation number you realize you actually don’t know that much. If you don’t get to that point, then there’s a good chance you are still talking more than you are listening. You may need more than 100 conversations. Describe your end user 100 times. See if you can describe the actual pain point that you solve for them. See if you can define why you are a must-have and not just a nice-to-have. See if you can convince others, or yourself, that someone will actually change their behavior to adopt your product. See how many times it takes before you don’t really even believe yourself anymore. At that point, you’re a lot closer to success. These 100 people aren’t “right”. In fact, they will contradict each other a lot. They will make the already difficult process of starting a company temporarily seem that much more difficult. So, why in the world would you do this to yourself? Because you’re not right either. And, the repetitions and iterations and brute force that talking to 100 people generates are your best start to getting there. M.C. Escher: Metamorphoses Image: https://images.app.goo.gl/nSMsrkBFAoniDFsF9  This is a hard lesson learned in the land of early startups and new products, but there are good reasons that it’s both a hard lesson and one that founders keep having to learn for themselves.
Entrepreneurs are typically driven by a vision, one that they hold dear, perhaps for many years, of how they can and will solve a pain that they’ve experienced and that they believe a lot of others experience - and will pay to fix. That vision is powerful. It wakes the entrepreneur up every morning. It inspires those first people willing to have coffee with you to bounce your idea off of. They validate it, making the vision that much more powerful. It excites friends and family who feel your passion and may even be willing to invest in it. They believe, which adds more fuel. It draws those first people who want to join your team and help build your vision. They want in. That vision is fundamental. It’s foundational. So, it’s hard to accept when in the face of business reality the vision loses its potency and immediacy. The vision is still important and deeply rooted, but it becomes increasingly marginal in the face of here-and-now questions about adoption, what you’ve learned from the market, and how you have used or will use investment to turn the early product into a viable business. In other words, unless and until people are using your product (people who aren’t your coffee-going friends or family) and you are building and iterating based on that feedback, your vision is in a state of diminishing value to your business. I’ve stumped even seasoned founders - after hearing their thoughtful and thorough business strategies, clear visions for the necessary features and functionalities of their products, and go-to-market plans showing how users will be downloading their app by the thousands - with a simple question (scaled to the business/conversation): Who are your first 10 (or 20 or 100) users? Followed by: why will they use it and why will they keep using it? And then, why will they tell someone about it? It seems obvious after I ask the question that you can’t get to 1000 users, much less 100,000, if you can’t get, and keep, your first 10. If you’re doing it right, the product will evolve rapidly as those numbers grow, so it’s ok to think about a small but as-representative-as-you-know first set of users who you want and need to learn from to prove your value. In fact, you must. One critical part of securing those early users is articulating the value you are going to deliver and then delivering it. It’s not necessarily about the magnitude of value for an early adopter. It’s about trust and belief that you and your product can deliver what you say you are going to deliver. Unfortunately, founders often fall into a self-created chasm between their vision and what they have had the time and investment to deliver successfully as a working product to date. Imagine a circle on a white board - let’s say 4 feet in diameter. This is the founder’s vision. Now, imagine a circle inside that circle that is say 6 inches in diameter. If you promise the big circle and deliver the small one, you’ve lost. It’s a major disappointment to the people who thought they were getting the big circle. You’ve not just over-promised and under-delivered; you’ve breached some level of trust. You’ve created even more doubters. Alternately, if you promise the little circle and deliver it, you win - even if it’s with a smaller user base and only delivering on a fraction of your vision. They may not yet be blown away, but they are that much closer to lining up behind your vision. In either scenario, you’ve delivered the exact same (small circle) value with dramatically different outcomes for your business. It’s important to understand that this value scoping is not compromising your vision. In fact, it’s the opposite. It’s building the product and the users and the business that are required to achieve the vision, which always takes longer and requires more money than you think.  As good as it may feel and as validating as it may seem for your early product, confirmation that the market has a problem and that your product seems like a good solution should not be confused with finding product/market fit.
Particularly in a B2B context and especially at the enterprise level, new product sales and adoption encounter a world of organizational dynamics, dysfunctions, disparate priorities, funding streams, and basic inertia that often are what actually create the need for your product but also undercut demand. My first startup created a mobile communication tool for both the education and the healthcare sectors at different times. In both, there was a clear and acknowledged communication problem - in education among schools and students, and in healthcare among administration and physicians. In each sector, we found a solid early interest in our solution. Both sectors, however, are also highly regulated and compliance driven. Both sectors are risk averse and bureaucratic. Both sectors have complex decision-making structures and resource allocation processes. And, both sectors are notorious for culture problems among administration, front-line staff, and the people they actually serve. This is why both sectors have severe communication problems (need), and also why both sectors have not been able to commit to solving (demand) their communication problems. Needing a communication solution and demanding one are two different things. Our startup got a lot of head nodding and early interest and affirmation, but was never able to scale our sales to match. In hindsight, we had achieved problem/solution fit (need oriented), but a couple of years later we were still searching for product/market fit (demand oriented). Image: https://forum.brickset.com/discussion/21293/requesting-information-regarding-2-top-vs-top-fit-together-1x1-round-bricks%EF%BB%BF |
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