 I used to be young and ambitious. Now, I guess I’m just ambitious.
Over the last 25 years, I have had the great fortune to work with hundreds of highly ambitious people across all walks of life and work. From fellow athletes to fellow artists, from community organizers to the marginalized young people we worked with, from startup founders to investors, from ministers to gang members, from teachers to doctors to politicians to parents, I have seen ambition in seemingly infinite forms. And yet, it dawned on me recently that despite the many topics in leadership I have studied and lived and taught over these 25 years, I have never put much thought to ambition. So, I tried to categorize people throughout my career to see if any patterns might emerge on ambition and where it comes from and to what end. Through this reflection, I discerned 4 archetypes of ambition that are not mutually exclusive, but the people I have known who I would call ambitious are driven predominantly by one with typically a clear second coming in behind it. Acquisitive People driven by acquisitive ambition look out into the world and seek to acquire what’s in front of them. They are effectively ambitious consumers of opportunity. They want to win, but they also really want others to acknowledge they won. At work, they may look for the promotion with their contribution or value creation a secondary notion. Their ambition is the position. Their purpose and goal are the external reward. Their ambition can serve them well in highly structured career paths. Advancing People driven by advancing ambition are trying to get somewhere and their drive and reward system are deeply rooted within. These are the people who live and work from their values and internal drivers and their work persists whether anyone recognizes them or not. They may be seeking a better life. They may be seeking to create more opportunity than they had. They may just be doing the thing they love. Their ambition can serve them well in creative or entrepreneurial settings where they make their own path. Altruistic People driven by altruistic ambition have something deep within that drives them to do right by the world. They are motivated and rewarded by the success of others which ties fundamentally to their sense of self. These are the people who always step up to help, to give, to mobilize, to engage even when they may not be directly affected by a situation or circumstance. They often sacrifice personal benefit for the sense of contributing to the greater good. They tend to give credit for success more than claiming it. Their ambition can serve them well in purpose-driven communities and organizations. Associative People driven by associative ambition want to help others but they also want to be recognized and known for it. They often do good in the world but can come across at the same time as self-promoters. They want to be seen doing good work and seen and associated with people and organizations that do good work. For them, the good deed is made better by the recognition that they were part of it. Their ambition can serve them well in societal and political settings built on social or economic standing and status. As I mapped out these quadrants, I realized again that we all possess a bit of each of these ambitions. I also recognized that my ambition has changed over time as I have aged, started a family, and changed careers. While my dominant ambition hasn’t changed, the degree to which it drives me has. So, what’s your ambition? Can you guess mine?
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 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.  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.  Life is full of stuff we can’t control, both big stuff and little stuff that can create chaos in our lives, work, and relationships. This reality just makes it that much more imperative that we avoid creating more chaos-inducing stuff for ourselves – that we control what we can control knowing that little choices today can create (or help avoid) big chaos tomorrow.
The goal is not to pretend we can avoid chaos altogether. I don’t think that’s life. The goal is to keep our chaos “resting state” at a level that gives us capacity to manage when the uncontrollable things hit. Managing our resting state then demands daily diligence and discipline around the little, controllable things. So, here are 10 ways you may be creating chaos today for your self tomorrow: 1. Not taking care of your mental health: Whether it’s managing stress, anxiety, Depression, grief, trauma, or otherwise, if you’re not managing it (or at least giving your best effort), it’s managing you and all of your relationships and work. 2. Not taking care of your physical health: Whether it’s exercise or sleep or what you eat, it impacts how you relate and respond to the world - adding chaos or neutralizing it. 3. Avoiding difficult decisions: Decisions that need to get made but don’t only get bigger and more complex in time. And, they don’t get easier or less necessary. 4. Avoiding difficult conversations: Conversations that need to be had but aren’t only get bigger and more complex in time. And, they don’t get easier or less necessary. 5. Not monitoring and managing your relationships: Relationships are dynamic and need tending to. Some relationships need more investment, some need less, and some you probably need to just let go of. 6. Cutting corners: When you sacrifice quality or completeness whether in work, relationships, or otherwise because you think you don’t have time or the energy to do things fully, it will almost always pay you back with a chaos flywheel. 7. Not defining and keeping your boundaries: People who can’t say “no” eventually create chaos for everyone around them. 8. Needing to be a fixer: Helping others is good. Enabling their chaos creation is not. Thinking you can fix their chaos only ensures you are now a part of it. 9. Being vague or ambiguous about your needs: Uncertainty in relationships or expectations breeds behavior, investment, and performance that are uncertain. 10. Failing to relentlessly prioritize: There is never enough time and yet we all have the same amount of it. We don’t find time or create it. We only prioritize it. Image: https://www.freepik.com/premium-vector/chaos-mess-circle-continuous-line-drawing_346070449.htm 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.  It can be hard transitioning to manager. It totally shifts the mindset and value-creation principles that so many new managers developed, delivered, and were recognized for in being promoted to manager. The shift isn’t just one of roles. In many ways, it can feel like one of identity. The people we promote to manager typically value what they do, and value the impact what they do has had on the company.
When we promote them to manager, we recognize them for what they have done, but we change what they do. We change how they are expected to add value and have impact. And yet, we rarely slow down to help reframe what it means to be a manager and how that’s different from the work they’ve done to get there. I was having this exact conversation with a new manager when it dawned on me that she was actually expressing a sense of loss in becoming a manager. She felt less impactful in this role, less valuable for “passing off” work to someone else that she had always done herself. So, in some attempt to hold onto her historic value, she kept doing what she’d always done - and just layered her new management duties on top. She was burning herself out, her team was flailing, and she was even considering leaving the company. This is a person who had recently been promoted because of her indefatigable energy and commitment to the company! They love her. She loves them! For nearly a decade, she has found life-purpose and meaning in her work there. She is proud to have helped build the company, to have been there to grind it out with the founders and just make stuff happen for their customers. In other words, she knows how to deliver value and how to feel valuable as a hard-working, dedicated, individual contributor. Now, she’s a struggling manager. It dawned on me that to reboot this transition to manager, she has to redefine her value creation equation – from an equation where she creates direct value to one in which she also creates value through others. I explained somewhat off-the-cuff that as an individual contributor, she delivered one unit of value with one unit of work. As a manager, when she enables one of her people to execute on that unit of work, she creates one unit of value out of the fact that it was executed and another unit of value out of the fact that someone else did it. In other words, as a manager, she is creating more value, not less, when someone else does the work and does it successfully. She looked at me puzzled for a moment, and then a sort of liberated smile flashed across her face. “That’s it!” She exclaimed. “I never thought of it that way. But, that’s it. I know I can’t keep doing what I’m doing. My supervisor has been pushing me that it’s not just about me delivering the work. It’s about the team. I’ve got a great team. I know they want more from me. They want to grow. I’ve just been thinking about it wrong.” So, here’s the simple math: Individual Contributor Value = Work Execution Manager Value = Work Execution + Capacity Building Work Execution Variable:
Questions for a new manager to ask yourself:
 Having difficult conversations is…well…difficult. This is especially true if you need to have a difficult conversation with a supervisor or someone else at a higher level in your organization.
I was recently coaching a young executive who had been struggling with a direct report, who had a history of creating challenges among the team even back to a previous manager. But, this person was also highly valuable because of their skills and experience, and no one wanted to lose them. The young executive with whom I was speaking had sought advice and support from his superior to deal with the issue. In an attempt to help, his boss said that the problem employee could just report directly to him and he would deal with it. Even with the best intentions and that positive sense of collective required in the hustle of a startup, this attempt to help created far bigger problems for the young executive. Now, the rest of his direct reports believed that if they disagreed with him or if they didn’t like what he said then they too could go around him and directly to his superior. The workaround intended to relieve this young executive had accidentally neutered his ability to lead the rest of his team and as a result multiplied his stress. We were talking through how he might have this conversation with his boss. Sparing additional detail, here were some key principles we landed on: Approach with gratitude: We talked about how he could acknowledge the good intent of his supervisor’s move and open the conversation with that appreciation. This would ensure that nothing came across as complaining or personal or ungrateful, which were things he was really worried about. He valued and wanted to protect his positive relationship with his boss. Appeal to common interests: This young executive was hired because of his own skills and the belief that he could lead this team and the company to a new phase of growth and maturity. He knew that he and his boss could agree on this premise. With that out in the open, he needed to describe the unintended consequences of changing the reporting structure. Clearly, neither of them wanted this young executive to not be able to perform the job he was hired to do. Focus on outcomes, not people: We talked about making sure the conversation with his boss never became about the valuable, but problem employee. It couldn’t become personal. It had to be about process and performance. So, this young executive needed to show with examples how his leadership was being undermined with other direct reports and how that was impacting performance. Define an agreeable path forward: This was not a situation that could linger. This young executive was losing authority and credibility by the day and as a result was also developing a lot of frustration and anxiety about his role and the work and so forth. So, he needed to use steps 1-3 to make sure the conversation was primed for: so what do we do now? Within a few hours of our conversation, I got an email back. The young executive and his boss had agreed that an announcement would be made to the team about the change in reporting structure, so it no longer looked like a workaround that others could also take. They also defined specifically when that announcement would be made. This path forward not only would help solve the authority problem but would also relieve the stress valve for the young executive who now knew something would happen. This wouldn’t linger. Perhaps most importantly in the long run, I suspect that this young executive’s approach and willingness to have a difficult conversation with his boss only reinforced why he was hired in the first place. I have a feeling his opportunity and authority will only grow as a result of the experience.  A leadership team I support was struggling with a particular employee and the issues had been lingering for several months. This employee had been a positive team member and quality contributor until recently. But lately, the employee’s performance simply hadn’t been good enough. The quality wasn’t there. Her work was often incomplete. It lacked depth and insight. And, it was starting to impact the team as the other members had picked up the slack and, as a result, was feeling the tension with management.
The management team had already let the employee know improvement was necessary. They had started to meet more frequently and to dial up the necessary feedback and micromanagement. But, the more time they spent together, the more the employee seemed to pull back. In other words, as they ratcheted up their formal communication to try to course correct, the informal and discretionary communication all but stopped. The managers didn’t want to fire her, but they didn’t know what else to do. They felt stuck. In a session with one of the managers, we discussed the simple-but-powerful 5 Whys process created decades ago by Toyota to help them drill down to root causes of problems in their manufacturing. The process is so simple, however, that it really works with any problem. Just ask “why” five times, each time asking “why” of the previous answer such that you create a sort of cascade of deeper and deeper problem statements. If nothing else, it can deepen your understanding of the variance and dynamics of a problem to know what part you have the time, energy, and resources to address. In other words, you may not always have the capacity to address the root cause but at least understand that you aren’t addressing the root cause. In this case, the manager took the 5 Whys back to her colleague and they agreed to use it as a structured conversation guide in a meeting with their struggling employee. They introduced the process and the three of them worked together to dig deeper into what was behind the employee’s poor performance. This was the manager’s message back to me: “I tried the 5 Whys in my conversation with this person. My boss was with me as well. So, I just introduced the process and put {the performance problem} up on a whiteboard and started asking why. It was so helpful keeping the conversation focused and not so emotional. And after all of this time where we thought the employee was the problem, we discovered she actually didn’t have all the information she needed to do what we had been asking her to do. It was us! It was our problem! And here we were thinking we were going to have to fire her! Anyway, we left the conversation so much clearer and in a much better place. It was great! Thank you!”  I was on a recent coaching call where a mid-level leader of an independent business unit within a rapidly growing company was dealing with the following realities:
1. Her team was entirely remote. 2. She was entirely remote from her supervisor and company leadership. 3. Her team was acquired over two years prior but still felt little connection with the acquiring company. She and her team were performing and performing well, but without much distinction from how they worked prior to the acquisition. The autonomy was good on some levels, but the challenge for this leader was that she was being asked questions about the larger organization, its vision and direction, and even what would happen when it exited. She didn’t have any of the answers. She felt as disconnected and uninformed as they did. There was a slow but growing sense of fear and uncertainty within her team and a developing anxiety within her as their leader. So, what should she do about it? How should she present her concerns? Here are some things we came up with: 1. Start with you. We talked about her just having some open conversations with her manager and/or peers at similar levels or situations within the organization as a way of asking how others were managing this better than her. Instead of looking up at the organization and starting with “you need to fix this”, this approach takes ownership and starts with “how can I do better”. No one is going to shut you down, marginalize your concerns, or get defensive when you start with “how can I do my job better?” 2. Speak on behalf of your team. As you explore how you can do better, frame it with what you are hearing from your people. Share their stories. Share the questions they are asking you that you can’t answer. Give a sense of their fear and frustration. Paint that picture. Then, frame your needs as it relates to your ability to effectively lead them. If you don’t feel informed and connected, you can’t help them feel informed and connected. So again, you are asking to be better equipped to do your job well – which everyone should be pretty well in favor of. 3. Show you are thinking big picture. Provide your supervisor the strategic context for your concern. Talk about the health of the team and the related health of the company. Talk about company growth and the challenges of retaining and attracting talent. Talk about the cost of losing some of the specific people who are asking you the questions you can’t answer. Talk about how this problem only gets bigger the more the company grows if it’s not addressed. 4. Listen for how others see, understand, and prioritize the issue. You don’t have to jump straight to solutions. In this case, the first goal is to raise the issue and get a conversation started. So, in alignment with #1, stay focused on tactical next steps and where they can start with you, but involve others where necessary. Rapidly growing companies have innumerable competing priorities. Raise your issue and better understand where it fits in the mix. This will help align expectations for action or lack thereof. Working with remote teams requires an entirely different level of intentionality when it comes to communication and culture. Problems like the one this leader was presenting don’t naturally get seen by company leadership and don’t organically surface in their day-to-day. Leaders in these situations must recognize this reality and find ways and forums for bringing these issues to light. They can’t just let them stay quiet. That’s clearly not in anyone’s best interest. Sometimes it’s hard to find the words or the process where none seem to exist. But, that doesn’t make conversations like these any less imperative. In order to effectively lead through others, you often have to manage up to get what you need.  I spend a lot of time with individuals and teams working on two big concepts: trust and communication. I always tell them: if trust is the foundation of leadership then communication is the medium.
And yet, I have had several occasions recently where more senior leaders have heard about these topics and figure the discussions and trainings must be for junior leaders. They are so basic! I would caution here not to confuse basic with foundational. As every architect knows, you can’t build anything without investing in, improving, and innovating at the foundation. Every foundation must be designed based on the needs of the structure, the current standards, the environment, new technologies and materials. No single foundation suits all buildings – or all relationships. PWC recently published their Trust Survey results for 2023 and they suggest that leaders across industries are underinvesting in their trust foundation – and their people feel it. Here are a few highlights from their research:
It’s also worth noting that 91% of business executives say that their ability to build and maintain trust improves the bottom line. Every human being who has ever had a relationship with another human being knows that trust is far easier to break than to build, much less rebuild. And, it’s hard to build a relationship much less a scalable company without due attention to its foundation. Here are a few tips for checking your foundation: 1. Emphasize the Why: Make sure everyone understands why the company exists and help them find meaning in working there. Help them find their personal "why" in the work regardless of their age, role, or level in the company. Meaning helps us keep a bigger perspective on our work and our relationships and keeps the little things from being trust breakers. 2. Share Values Stories: Trust is built over time and the more you build the more grace you get when a trust-breaking event happens. Your company stories are your “grace bank” that help you build a track record of living your values so that when it appears you had a miss, people see and understand that as the outlier not the norm. 3. Communicate Constantly: Another one of my refrains is that “silence is never silence” in a company. In the absence of your voice, the voice of the company, your people will make up their own stories about you and it – and they are likely to be worse than reality. 4. Own Your Mistakes: Making mistakes does far less damage to trust than not owning those mistakes. You make mistakes. Companies make mistakes. The trust impact comes down to how you handle that reality rather than deny it. |
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